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Preparation and polymerization of certain diunsaturated silanes.

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Preparation and polymerization of certain diunsaturated silanes.
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Preparation and polymerization of certain diunsaturated silanes.
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Stackman, Robert William,
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Gainesville FL
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University of Florida
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Free radicals ( jstor )
Infrared spectrum ( jstor )
Molecular chains ( jstor )
Monomers ( jstor )
Peroxides ( jstor )
Polymerization ( jstor )
Polymers ( jstor )
Reagents ( jstor )
Silicon ( jstor )
Spectral bands ( jstor )

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University of Florida
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University of Florida
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Copyright Robert William Stackman. Permission granted to the University of Florida to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
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Full Text












PREPARATION AND


POLYMERIZATION OF


CERTAIN DIUNSATURATED SILANES













By

ROBERT WILLIAM STACKMAN


A DISSERTATION PRESENTED TO THE GRADUATE COUNCIL OF
THE UNIVERSITY OF FLORIDA
IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE
DEGREE OF DOCTOR OF PHILOSOPHY










UNIVERSITY OF FLORIDA
January, 1961














ACDKcXW LED GEMENT$


The author wishes to express his gratitude to Dr. George B. Butler forhise guidance and encouragement during this vork, and to Dro 1, D,. Berlin and the members of his Suprvisory Committee for their advice and suggestions, He wishes to express his appreciation to the many graduate students, vho through their assistance,. suggestions, and encouragement, contributed much to this work, and Mrs. Geraldine Houck who typed the manuscript.

The work described in this dissertation was performed under the sponsorship of the United States Air Force through the Materials Central of the Wright Air Development Division,


LL



























TALE OF CONTENTS


ACKNOWLEDWE NENTS. .. LIST OF' TABLES. ** ****



Chapte r

to INTRODUCTION 0 ***


A. Literature Review o Be statement 'of Problem



its PREPARATION OF MONMERS



A* Materials ..**



B. Equipment and D)ata


Pase



a 0 o o 0 0 0 0 * L



S0 ' s... 060 0 0 0 v


0



0



0



0


* 9 0 0 *


0 00


*00 000


000 050


C. Preparation of Intermediates



1, Allyl Grignard reagent'*


2. ?lethaI3.y1 Grignard reagent 1). Preparation of Monomers **


00



* 0



* 0


* .



* S



* *0



* 0 5.


S.



*0



* 0



* 0 S.


0


000oi *00


000



*00



* 0*


00000



*0000 00000


*0


000


000 So. 000


S



0


0


0



0


S


0



0


6



7





8



8



8


9


9


*000 00*0


00000 00000


0000050*0000


1. Dial lyldiinethyisilane f CU2-'CcH2) 2Si(Cu3)2. 2. Diallyldiphenylsilans F~"2-=M"2) 2S (C6E5)j


3. Diallylmethylphanylsilane

PM H.c~)2LO3) C6eli **,e.

4. Diallylcyclotetramethylenesilane

P5jduOud-CH2)2si(Cu 2)41 0 . e .

5. Diallyleyclopentamethylenesilane

CR2=CE=2)2SL(CE2)1.

6. Dimethallyldimthyluilane

CHY C(CH3)C2)2Si(CR3)j.* 0 0 * 0 a *

7. Dimethallyldiphonylailane




8. DimethallylwsthylphanylSilane


JkCHa.!C(cUt3)CH2)j8i(cU3)C6HuI 0 0 00 0



iii


0


0


*0


0


S


0


9

,t0 10














12 12 13


* *0




*0* 050 000 0*0 000














9. Dtmetballylcyclopentaxnethylenestlane
[(MCzy(c3)CH2)0ss(cu2). .. ..
10. Allyldimethylvinylsilauo02u88 (e)2uw]


IMI P0LYNRUZATI0NS bsb...

A* Materials a. o o o o o i


Cob COO Ct C C. CO****~


B. Equipment and Data .. .. ., . . .. 0 4. * . o1


Co General Polymerization Proceduares

1. Ziegler catalyst polymerization
2, Free radical polymerization. Do Polymerization of Monomers . . 0'..


1.
2.
3,
4.
5.
6, 7.
8.
9.
10.


Diallyldimethylailane ....C
Diallyldiphonyluilazi n.. Diallyluiethylpbanylsilane . .. . .. Diallylcyclotetramethylenesilane
Diallylcyelopentamethylenesilane Dimethallyldimethylailana , Ditethallyldiphenyleilane .. . Dtmethallyloethylphenylsilane . Dimethallylcyclopentamothyleeilano Allyldimethylvinylsilane o". * * *


C ~ SCSC COt

* U C C C * CC C
* CO OCOCO C

* 'C C C C 'CCCC


0
C


*'Cbb Ob
* COCCC


* 0 o o o 0 0 0 0CC C C 0 0 0 0 0


tv. Discussion ****CC 000 0 C0C C000CCC

V, SUKMARY . . . . C** e.



BIOGRAPHICAL ITEM


13
14 16 18

18 19

19
20 20 20 21 21
22
22 23 23
24 24 24 35

42 44

48













LIST OF TABLES


Table Page

1. Ziegler Catalyst polymerization of 3)iallyldimethyleilane . 26

2. Effect of catalyst AgingUpon the Polymerization of
DiallyldiiaethylsilsA6 .~ *~ *** **.

3, Free Radical Polymerzation~ Of 'Diallyldimlethylsilane IS .2

4. 'Ziegler Catalyst 'Polymierization of'Diallyldiphemylailane *. 10 5. Free Radical Polymerization of Diallyldiphenylsilane .. 30

61 Polymerization o f fiallylmethylpheuylsilane ..*.3

7. Polymerization of Diallyleyclotetramethyleneeilano * # 32

a, Polymerization of Diallylcyclopentamethyleneeilane . # 33

71 Polymerization of Dimethallylsilanes ,. ,. . ..... .*. 34


v















CHAPTER I

INTRODUCTION


A, Literature Reviewy


Previous work in these and i~n other laboratories has shown that many non-conjugated diene systems may be polymerized to linearp,soluble,. saturated polymers containing a cyclic repeating unit,

Butler and Ingley, and Butler and Angelo reported that diallyl quaternary ammonium salts polymerized to yield water soluble, linear polymers which contained little or no residual unsaturation.. An alternating Intramolecular-intermolecular chain propagation mechanism wnas proposed to account for the polymers produced. 2According to this mechanism, diene monomers capable of forming si-mbered ring systems by an intramolecular attack on the terminal mnethylene of the second double bond within the same molecule can result in linear saturated polymers, as indicated below:

ZCC2 on.fl2 2l C

ai2l 2 II knZC 1 H

2 H2 11 2

The process consumes two double bonds per molecule,. each molecule being converted to a six~-membered ring.

Considerable evidence for such a mechanism can be found in the literature. Walling 3has commented on the fact that observed gel-points


1









2


in polymerizing systems, capable of crosslinking, should occur slightly later than calculated by use of the gel-point equation of Stockmayer cldue to the occasional formation of cyclic structures, Studies were made on systems of methyl methacrylate and ethylene dimethacrylate, and vinyl acetate and divinyl adipate. The observed gel-point to calculated gel-point ratio was often as high as 15-20. Simpson, Ilolt, and Zeite5 studied the polymer of diallyl phthalate at that gel-point and found that about 40 per cent of the reacted monomier had been used up in the formation of cyclic structures, Haward calculated from probability considerations that 31 per cent of the reacted monomer in polymerizing, diallyl phthalate should be used up in cyclization of some kind. The experimental results obtained by Simpson a. 5are in good agreement with this calculation, Simpson and Hlolt 7and llavard and Simpson have extended their vork along these lines. More recently Qivra and Osata 9 have shovn that as high as 81 per cent cyclization occurs when diallyl phthalate is polymerized in solution.

Butler, Cratshaws and Mle10degraded representative polymers of diallyl quaternary ammonium salts and proved the presence of piperidinium rings in the polymer chain.

Polymerization by this mechanism has been extended by Marvel and Vast 11who polymerized apcz -dimethylene pimelate derivatives to essentially saturated linear polymers. Marvel and Stille1 described essentially saturated linear polymers from 1,5-hexadiene and 1,6-heptadione by use of the trialkyl aluminum-titanium tetrachloride catalyst, although some crosslinking occurred in the case of 1,5-hexadiene. Polymerization of 1,6-heptadiene gave no crosslinking although the soluble polymer









3


contained 4-10 per cent of monomer- units which had not cyclized' and each 13 14,15
contained one double bond* Crawshaw and Butler and Jones independently described polymerization of acrylic anhydride, under a variety of conditions, to a soluble polymer., In an attempt to synthesize diacrylylmethane by a Claisen condensation of methyl vinyl ketone with ethyl acrylate, Jones6 isolated'poly-(diacrylylmethane) uhic-h he attributed to AniLonic poly merization of the monomer as it formed. Jon-as17 has also prepared a cyclic 'polymer from allooccimene., Marvel, Kiener, and Vessels,1 however, have described a linear, unsaturated polymer from this monomer by Ziegler catalysis. Marvel and Vest 19 have described soluble polymers by polymerization of czpca'-dimothiylencpim clonitrile as well 'As &op olymer' of this, monomer with other well-knobwn tonomers., Marvel I and 'Gall described the preparation of 2,6-diphenyl-6l,6.hapiadibee and Field 21has described the polyuiarication of this monomer by all the known general types of initiation, free radical, Ziegler type, cationic and aniouic, to give a polymer having cyclic units. Marvel and
22
Gall polymerized this muonomer, and also Z#5-diphonyl-1p5-hoxadieneL and

2.7 -diphenyl-lThoctadiene to yield polymers with cyclic recurring units. They found'that the five- and seven-membered rings form less readily than does the six-membered ring in such polymerization reactions.
IPrice 23has described soluble copolymers of diallylalkylamine oxides with acrylonitrile and other monomers. These copolymers were assumed to possess one double bond for each molecule of diallylaniine oxide entering the chain, however, in view of the polymerization mechanism under consideration, copolymerization has probably occurred according to this mechanism to produce saturated copolymers. Schuller, Price,










4


Iloore, and Thomas 24have described a number of soluble copolymers involving several diallyl monomers and several conventional monomers, and have postulated that these copolymerizations follow the mechanism~ under discussion. Friedlander reported the cyclization of allyl ether and allyl sulfide to substituted tetrahydropyrans and tetrahydrothiopyrans

respectively when attempts were made to add various reagents under free radical conditions.

.Berlin and Butler 26 have described soluble polymers from diallylphanyiphosphine oxide and dimethallylphenylphosphinc oxide, and Skinner 27 has described soluble polymers from diallylalkylarylphosphonium salts.

Harel nd oolord28and Butler and Stackman 29have reported linear polymers from diallyldimethylsilane.

lNarve]. and Garrison obtained varying ratios of soluble polymers from higher diolefins in uhich the terminal double bonds were separated by from four to eighteen meithylene groups. Cyclization in these polymecrizations can give rise to rings of from seven to twenty-one members.

stuble31 has described polymerization of l,6-diyncs, by use of the Ziegler catalyst, to linear, cyclic polymers in which the polymer backbone consists of a continuous conjugated system of double bonds.

Barnett, Crawshaw, and Butler 32studied the polymerization of unsaturated esters of rmaleic and fumaric acid and obtained soluble polymers which contained cyclic units.

Butler 33 has shown that 1,4-dienes will undergo copolymerization with certain olefins to produce polymers containing a six-membered ring formed during the process. Other copolymerizations were studied which









5

involved 1,5-diencs and molecules which are capable of inserting one atom Into the propagating chain, such as sulfur dioxide.

-Delmonte and Hays 3 have described the cyclization of a diolefinic monomer which is accompanied by chain transfer. They studied copolymerizations with vinyl acrylate as one of the monomers,. and cyclization of the vinyl acrylate followed by chain transfer stopped the reaction.

There are many references in the literature to certain dienes in which cyclization may have occurred during polymerization. lBlout and Ostberg 35and Cohen, Ostbarg, Sparrow, and fllout 36studied the polymerization of allylmethacrylate at both low and high temperatures# At elevated temperatures gelation occured at 6 per cent conversion while at

1 0 gelation did not occur until 39 per cent conversion. Evidence was presented indicating that cyclizati on may have occurred but the results were not attributed to this.

In an attempt to evplaiLn the strong polymerization tendencies of 1,6-dienes relative to their monoolefinic counterparts, it has been suggested that there exists some kind of intramolecular electronic inter33
action between the two double bonds. A simple, well-known example of this type of interaction is found in the case of the Claisen rearrangemient, in which 1,6-dienes rearrange through an intramolecular mechanism. 37 The proposed interaction is also supported by the work of IHarvel and
12, 24 2333
stillep Schuller, eta~ Price,2 Miller$ and Milculasova and
Hvirik. 39 Miller studied the shifts in the infrared spectra band for the in-the-plane*.deformation vibration of the terminal methylene group for a series of diallyl compounds, Mikulasova and U1virik 39have shown that









6

the total activation energy of radical polymerization for diallyldirnethylsilanc is about 9 hilocalories per mole double bond less than that for allyltrimethyloilane. All of this evidence along vith ranny other published articles strongly supports this idea of an interaction betvaen the double bonds in 1.6-dienes.


B. Statement of Problem


The purpose of this research is to investigate the scope of the intramolecular-intermolecular polymerization mechanism by:

a. preparing a series of diunsaturated silanesp %Ihich are

functionally capable of undergoing a cyclizationg as a

part of the polymerization reaction, to give linear,

saturated polymers,

b. polymerizing these monomeric silanes, and

c. studying the resulting polymers.
















CHAP PTMt II

PI'MPAr.ATIo1N OF 1U011llEflS


In order to study the polymerzation of diunsaturated silanes it was decided to prepare a series of diallyl- and dimethallylsilanes* The other groups attached to the central silicon atom were varied to study any effect that they might have upon the polymierization* It was thought that the polymers of compounds, in which the central silicon atom was contained in a ring, might give polymers possessing interesting properties. Cyclic organosilicon compounds have been prepared by West.,40 Tamborski and Rosenberg 41have reported a series of dialkylcyclopentamethylenesilanes. In addition to the diallyl- and dixnethallylsilanes allyldimethylvinyloilane was prepared in which the ti,- unsaturated groups were of different lengths,

Several diallyl- and dimethallyl siuance have been prepared. 42'43'44 Nasiak and Post~ prepared a series of these compounds by the action of allyl or methallyl Grignard,,reagents.,upon the appropriate chlorosilane, This method was used for the preparations in this investigation.


A. llaterials


The chlorosilanes, vinyldimethylethoxysilane, allyl bromide and methallyl chloride were purchased from Peninsular ChemResearch Inc., Gainesville, Florida# and were distilled before using. The vinyl Grignard reagent was also purchased from this company and was used as


7









a


received, The other ins obtained from stock and we dried over sodium ribbon before use.

As . Entapmsnt and Ratea

Temperatures reported In this Vork are u44orrectedo Distillation pressures we've read an a ZiomerlU pug**
;.Infrared data veto determined with either a Perkdin-91inr Model 21 spectrophotometer or a Perkin-Elmaer Infracord speotrophotoineter.The gas-liquid chromatographic analyse VOre performd with a Wilkins Aezogaph Model A-13.OC Pas chomatographic inetuisnt, USing helium as the carrier Sas and a five foot column packed with 0. Z., Mra96 silicon* on C-22 fire brick,

Refractive indices were determined with a Sausch and Lomb Abbe 34 regractometer fitted with an achromatic 'coumpenatiug plism.

Densities were determined on approximately 5 mt. samples and all weighings were made on an analytic balance,

Kicroanalyses were performed by Clark Microanalytical Laboratory,.



U.Pr faaticrn of lit emedats



to a five-liter, threemneck*4 flask$ equipped with a reflwxe on-. dens, addition funnel and mechanical stirrer,. were added 03 s,. (3*5 a.-atoms) of agnesium turaiup and 1,75 1, of absolute ether, The flask wo flushed with dry nitraon. 2*o hundred and twelve grams (1.75 =*I*s) of allyl bromide were weighed and a few milliliters were added to









9l


the flask, wiith stirring. When the other began to refiw:, the mnixture was cooled with an ice bath) and the remainder of the allyl bromide# diluted with an equal volume of ether, was added dropwise over a period of nine hours. Throughout this time the flask was cooled in the ice bath. When the addition wans complete the mixture was stirred for an additional hour and then two 1 ml. aliquots were titrated with standard base. The solution was found to contain 1.65 equivalents of the allyl Grignard reagent; yield; 94 per cent.


2. Methallyl Grignard reagent

Into a two-liter, three-necked flask, equipped as above, were

added 36 g. (1.5 g.-atoms) of magnesium turnings and 500 ml. of absolute ether. The reaction was started by the addition of c- fCei milliliters of allyl bromide, The flask was cooled with an ice bath and 91 g. (1.0 mole) of methallyl chloride tere added dropwise over a period of three hours. After the addition was completed the mixture was stirred for an additional three hours. The Grignard reagent was a smooth suspension in the ether and was too thick to analyze by titration.


D.- Preparation of Monomers


1. Diallyldimethylsilane FCU2mlCH2) 2Si(CH3)

To 2.3 1. (2.3 equivalents) of allyl Grignard reagent were added 129 g. (1.0 mole) of dimethyldichlorosilane over a period of four hours. The mixture was stirred for twenty hours at room temperature. Hydrolysis was accomplished by pouring the contents of the reaction flask into a chilled, 10 per cent hydrochloric acid solution. The ether layer and









10


one 100 ml.ether extract of the aqueous phase were dried over'calcium chloride; removal of the solvent by distillation left an oil vwhich, when fractionated, gave 106 S. (76.5 per cent) of diallyldimathylsilanep b.'p. 135", nD 1.4405 fjreportedt b.p. 135-1360, I'D 1,4402_] . Gasliquid chromatography indicated that the compound vas pure. An infrared spectrum of the compound exhibited the following bands (cm.- 1): 3050, 2950,:2900 (C-11); 1635 (CII 2=C'--); 1423, 1390, 1298, 992, 894 (CHI and CH 2 deformations); 1255, 830 (.Si(C13) .)


2. Diallyldiphenylsilane IEtC1CII2 2SL(C6115 2 ]

To a solution of 1.5 equivalents of allyl Grignard reagent were added 126 S. (0.5 mole) of dichlorodiphenylsilane, over a period of two hours. The mixture was stirred for twenty-four hours and was then treated in the same manner as was the above preparation to give 91 g. (71 per cent) of diallyldiphe .nysilauiep b.p. 1340 (I =...n 1.5738 reported 44 b.p. 140.50 (2 =,.), n 20 1.5750j *I The infrared spectrum of D
this compound exhibited the following bands (cm. ): 3050, 2970, 2950, 2900 (C-H); 1960, 1880, 1800 (phenyl> l63 C.Cl~;12,15,90 900 (CH and CH 2 deformations); 1428, 1111 (Si-phenyl); 1190 (Si-C)s


3. Diallylmethylpheflylsilane FSc1u2clo'i2) 2Si(CH3)CO15]

To a solution of 1.2 equivalents of allyl Grignard reagent were added 100 g. (0.52 mole) of dichloromethylphenylsilane. The mixture was stirred for twenty-four hours and was then treated in the same manner as was the previous preparation to give 80.3 g. (75 per cent) of diallylmethylphenylsilane, b.p. 1240 (15 mm) 20 1.5200 Lreported--











20
b.p. 123.5-124.4o (20.5 um.), nD l.52a2j An infrared spectruma of this compound exhibited the following bands (cm. 1)- 3060, 2970, 2950,. 2875 (C-1l); 1960, 1880, 1800 (phenyl); 1635 (C112=C-); 1435, 1390, 1300, 987, 893 (ciand C0U2 deformations); 1426,. 1112 (Si-phenyl); 1250, 030




4. Diallylcyclotetramethylenesilane L(d112=dn..du2) 2Si(Cu2Q4~

'To a solution of 1.05,equivalents of allyl Grignard reagent were added 67 S. (0.43 mole) of dichlorocyclotetramethylenesilane over a period of two hours. The mixture ias stirred for an additional eight hours and was then treated in the same manner as were the previous preparations: to~ give 56 g. (79 per cent) of diallylcyclotetraxnethylenesilano,
98 0~(5m 24 24 r
b.p. 9811,(5m pn D 1.4857p dZ 0.8325, MD 54.3 calcd. 54.9.4

Gaswliquid chromatography indicated that tho compound was pure, An infra_1 01
red spectrum of this compound exhibited the follouing bands (cm. ): 3050,

2930, 21850 (C-1H); 1635 0111-0d-); 1450, 1415, 1400, 1380,. 1290,1 990, 894 (CII and MI 2 deformations); 1245, 855 (Si-fl).
IAnal.' Calcd, for C 10U18si:, C, 72.20; 11, 10.90; Si, 16.88. Found: C, 69.80; H, 11.64; Sip,17.33.


5. Diallylcyclopentamethylenesilane L(C1l2=cn1C,) 2Si(cn12)5]

To a solution of 1.48 equivalents of allyl Grignard reagent'were added 100 g. (0j59 mole) of dichlorocyclopentamethylenesilane, over a period of three hours. The mixture wma stirred for an additional eight hours and was then treated in the same manner as w-as the previous preparation to give 72 S. (68 per cent) of diallylcyclopentamethylenesilane$









12
24 88 4d45
b.p. 1049 (24 mrn.)j nD- 1.488 ,Z 0.8779, 11D 59.9 calcd. .6.6 Gasliquid chromatography indicated that this compound was pure, An infrared Bpectrum-of this compound exhibited the following bands (c7): 3030, 3030, 2900, 2850, 2800 (C-11); 1635,(Gfl12=C11.); 1.450, 1.4201 1400, 1300, 990, 900 (C11 and CU 2 deformations); 915 (cyclopentamethylene silicon ring). 46

Anal. Calcd. for C 11120Si: C, 73.28; I, 11.18; Si, 15,54. Found: C, 72.07; 11p 10.82; Si, 15.06.


6. Dimethallyldimethylsilane [(Cn2'C(Ccu3 )CH2)2Si(Cu3 2

To a suspension of the methallyl Grignard reagent, prepared wi~th 1.0 mole of methallyl chloride, were added 25 S. (0.2 mole) of dimethyldichlorosilane over a period of one hour, After the mixture waes stirred for twelve hours at room temperature, the mixture was treated in, the same manner as wevre the previous preparations to give 24,&g,,' 71. per cent) of dimethallyldimethylsilane, b.p. 75-79O (25 zm.), nD0 1,.4525 [reported 44 b*PO 71-71.60 (22 mm.), n 2 1.453811. Gas-liquid chromatography indicated that this compound twas pure. An Infrared spectrum of this compound exhiLbited the following bands (cm.- ):, 3030,2850, 2770 (C-11);- 1640 (CII=dil-); 1450, 1440p, 1370,. 1276, 997, 870 (CHI and CH2 deformations); 1247,. 830 (-Si(CH 3)2'.)'


7. Dimethallyldiphenylsilane [(CU7tzC(CH3)CH2)2 2S(CO15) 2]

To a suspension of the methallyl Grignard reagent, prepared from 1.0 mole of tncthallyl chloride, were added 63 g.(0.25 mole).of dichlorodiphenyloilane over a period of one hour. The mixture was stirred for an additional timenty-four hours and vas then treated in the same manner as









13

vere the previous preparations to give 41, g. (55 per cent)-of dinotha11yl022 44
diphenylsilane, b.p. 148S (0.5 m-.), n,) 1.5650 reportedd .b.p. 193.8020
194.10 (14.5 rnm.), nD 1.5693j]. An infrared spectrum of this compound
-11
exhibited the following bands (cm. ):' 3050, 2930, 2910, 2720 (C-11); 1960,,1880, 1800, (phenyl); 1635 (dCI1-); 1450, 1370,130,j 1280, 975, 875 (CII and:MC2 deformations); 1430, 1110 (Si-phenyl); 1190 (Sir.).


8. Dimethallylmethylphenylsilane E(C1fC(C 3)Cn2 2Si (CH 3)C65]

To the suspension of the methallyl Grignard reagent, prepared from 1.5 mroles of methallyl chloride$ ,,are added 70. g, (0.37 mole) of dichloromethylphanylsilane over a period of onc hour. The mixture %''sT stirred for an additional twenty-four hours and was then treated in the, same manner as were the previous preparations to give 43 g. (51 per cent)
0 22
of din-othallylmethylphenylsilane, b.p. 1330 (12 rm.), nD 1.5180 reported' ' b.p. 14243 (20 m ),nD 1.5221l An infrared spectrum of this compound exhibited the following bands (cm.'I): 3050, 2980,,2910, 2850, 2720 (C-11); 1960,9 1880, 1800 (phenyl); 1635 (C212f=CII-); 1450, 1400, 1370p 1305, 1280, 980, 875 (CIU and CH 2 deformations); 1430, 1120 (Si-phenyl); 1255, 835 (Si-R).


9. Dimethallylcyclopentamrethyleneilale' jD(dU27C(Cil3 Gi2) 2Si(C12)5]

To the suspension of the methallyl Grignard reagent, prepared from 1.8 moles of mcthallyl chloride, were added 82 g. (0.45 mole) of dichlorocyclopentamc-thylenesilane over a period of one hour. The mixture w,.as stirred for an additional twenty-four hours and then tas treated in the same manner as were the previous preparations, to give 58 g.









14

(59.5 per cent) of dimiethallylcyclopentame-thylenesilane, b.p. 95 0 (2 rni.)p n 2 1.4907p d 24 0.770, M1RJ 66.8 calcd. 68.9. 45Gas-liquid chromatography indicated that this compound was pure. An infrared spectrum of this comnpound exhibited the following bands (cm. ): 3100, 2970,2900, 2300,(0C71); 1640 (C112=Gfl-) ; 1450, 1400, 1380, 1345, 1280, 993, 875, (CH and C112 deformationG); 915 (cyclopentariethylene silicon ring). 461

Anal. Calcd. for CO3UP'S: C, 74.94; 11, 1.61; Si, 13.45. Found: C, 74.01; lip 11.36; Si, 13.77. 10. A3lyldimethylvinylsilane E12ddxsdI)2nc2

a. To a solution of 1.8 equivalents of vinyl Grignard reagent in tetrahydrofuran vere added 134 g. (1.0 role) of allylditiethyichioroDilana, dropise over a period of five hours. The mixture vas stirred for an additional ttwenty hours and vas then treated in the same manner as were the previous preparations to give 64 g. (51 per cent) of allyldLtathylvinylsilane, b.p. 1110 (760 =..)p 22) 0.35 d4 07540, HD 43.39 calcd. 44.23. G as-lquid chromatography indicated that this compound

-,as pure.

b. To a solution of 1.0 equivalent of allyl Grignard reagent

%ere added 130 g. (1.0 role) of vinyldimethylethoxysLiane over a period of one hour. The mixture was then stirred at reflux, temperature (400) for forty-eight hours, At the end of this period no reaction had occurred. To the reaction flask was then added 500 ml. of benzene$ and 500 ml. of ether were removed by distillation. The mixture was stirred at 700 for twenty-four hours. At the end of this period a large amount of salts had formed in the mixture, The mixture was then treated in the same









15

manner as were the previous preparations to yield 35 S. (28 per cent) of allyldimethylvinylsilane, b.p., iii, (760 =n.). The refractive inden: and gas-liquid chromatography retention tire for this compound were the same as those for the product in the first preparation of this compound above.

Both products also possessed identical infrared spectra. The spectrum exhibited the following bands (cru1i): 3030p 3000, 2950 (C-fl); 1635, 1600 (CH2-C-); 1450p 1425, 1390, 1300, 1010, 990, 950, 895 (CHI and CU2 deformations); 1255, 850 (-Si(CH 3)2-)

Anal. Calcd. for C7I4i C,6.7UI,1.7 Si, 22.24.

Found: C, 66.61; Up, 10.95; Si, not determined.















CHAPTER III

POLYMERIZATIONS


It was expected that the silanes, described previously, would undergo homopolymerisation by the intra-intermolecular polymerization mechanism. The work of Marvelpet al. 12.18..22 has shown that six-membored cyclic units form more readily than do five-membered rings and therefore some difficulty might be encountered in the polymerization of allyldimethylvinyleilane. Also in view of the larger size of silicon compared to carbon and the known tendency of silicon to form eight-membered rings in the siloxane series, 47one is led to the conclusion that

the five-membered ring may be difficult to form.

Attempts have been made previously to polymerize a few diallyl,

and dimothallylsilanes with free radical initiators at high pressures.4'49 These attempts have led to low molecular weight oils and cross-linked, infusible solids. A k~netic study of the free radical initiated polymerization of diallyldimethylsilane and allyltirmethylsilane has been made 39and low molecular weight polymers were reported. Polymerization of diallyldimethylsilane and diallyldiethylsilane by use of a triethyl aluminum-titanium tetrachloride complex catalyst has been reported 50in which both liquid and solid polymers were obtained. From the liquids could be isolated trimers, tetramers, and pentamers, however, the solid polymers were insoluble in benzene, ether, and carbon tetrachloride but swelled in heptane. These solids were obviously cross-linked.


16










17

Marvel and Woolford obtained soluble polymers containing cyclic units from diallyldimethylsilane with Ziegler-type catalysts. Butler and Stackman 29polymerized diallyldimethylsilane and diallyldiphienylsilane with Ziegler catalysts to yield soluble, saturated polymers.

It was decided to attempt the polymerization of the diunsaturated silanes with both Ziegler catalysts and with free radical initiators,. Due to 'degradative chain transfer" most frce radical initiated allylic poly51
merizations tend to give relatively low degrees of polymerization. The

Ziegler catalysts might be expected to give higher molecular igiht polymers. A great deal of vork has been published concerning polymerications by use of these complex metal catalysts in the past fiveyer,5o3 With these catalyst systems it is possible to obtain high molecular weight polymers of a-olefins which could not be polymerized with free radical initiators. There are, however, some types of a-olefins which cannot be polymerized with conventional Ziegler catalysts. It has been
52
reported that a-olefins with branching closer than the 3- or 4-position to the double bond cannot be polymerized by this method. In view of this evidence it would be unlikely that the diumthallylsilanes and possibly the vinylsilanes would polymerize with the Ziegler catalysts. if these findings hold true for these compounds it will be necessary to polymerize them by means of free radical initiators.

The Ziegler catalyst system chosen for the polymerizations was triethyl aluminum-titanium tetrachloride, This is a common catalyst system and both of these materials are readily obtainable. The free radical initiator chosen was di-t-butyl peroxide. This initiator was










13


chosen because it is readily obtainable and is soluble in the non-polar systems whAich will be used in the polymerizations.

Intrinsic viscosity measuremxents will be made on samples of the

polymers obtained in order to get an approxitoation to the relative degree of polymerization.


A. Materials


The triethyl aluminum was obtained from the Hercules Powder Co. Inc., Wilmington, Delaware, as a 25 per cent by weight solution in heptane. Titanium tetrachloride was purchased from the Fisher Chemical Co., Fairlawn) Nlew Jersey. Di-t-butyl peroxide was obtained from the Shell Chemical Corp., New York, New York. The dicyclopentadienyltitaniuln dichloride was provided by the National Lead Co,, New York, New York.. Benzoyl peroxide vas purchased from the Cadel Chemical Corp., Burt, New York, and the x,al-azobisisobutrronitrile was purchased from the Eastman Organic Chemicals Division of Eastman IKodalt Co., Rochester: New York, The heptane used in the polymerizations was obtained from stock and was distilled from sodium cubes and stored over sodium wire. Benzene, used

for intrinsic viscosity measurements was reagent grade obtained from Fisher Chemical Co,j New York, New. York. The benzene, methanol, and other solvents used in this work were obtained from stock and were used as received.


B. Equipment and Data


Intrinsic viscosity determinations were performed using either a

Cannon-Fenske-Ostwald or Cannon-Feneke Se,.i-Micro Dilution type viscometer,










19

Melting points were determined in open capillary tubes in a meltin& point block.

Infrared data were determined with either a Perkin-Elmer Model 21 spectrophotometer or a Perkin-Elmer Infracord spectrophotolmeter.

NUlcroanalyses wcre performed by Clark lMicroanalytical Laboratory, Urbana, Illinois,


,C. General Polymerization Procedures


1. Ziegler catalyst polymerization

Into a 50 or 100 ml, reaction flask, equipped with a reflux condenser, mechanical stirrer, gas addition tube, and rubber injection gasket, wras injected a measured amount of dry heptane. The flask ras swept with dry nitrogen. 1-Ieasured amounts of triethyl aluininuin and titanium tetrachloride were then injected into the flask. The dark brown catalyst suspension was heated and stirred for a definite period to age the catalyst. After this period the m;nom~r was added and the mixture was allowed to react for various periods of tire. At the end of the polymerization period the mixture wias hydrolyzed by pouring it into methanol. The polyiner was removed from the mixture by filtration, washed with a 10 per cent hydrochloric acid solution, and dissolved in benzene, The solution was filtered to remove any insoluble polymer and then the soluble polymer was reprecipitated by adding the solution to rapidly stirred methanol. The polymers were further purified by repeated reprecipitations from benzene solution, The solvent was then removed by storing the polymers in a vacuum desiccator.










20


2.t Free radical polymerization

In a 20 tm*test tube, equipped wirth a ref lux condenser, iMas

placed a solution of the monomer and the free radical initiator (di-t-butyl peroxide). The solution was heated by placing the tube in a bath maintained at 135 0by re fluxing xylene. At the end of the polymerization period the

heat was reirioved. The polytmers were removed from the tube and purified in the same manner as were the Polymers obtained with the Ziegler catalyst.


D. Polymerization of Monomers


1. Diallyldimethylsi lane

This monomer was polymerized by both free radical and Ziegler

catalyst initiation. The results of these polymerizations are sunnnarized in Tables 1, '2, and 3. From the Ziegler catalyst initiated polymerizations were obtained heavy; viscous liquids, gurny, semi-solids, and 1wh1ite solids. All these fractions were soluble in benzene, heptane, and chloroform, A small amount of insoluble material was also found among the products. A series of experiments was performed in vhich the catalyst mixture, made up of various mole ratios of the co-catalyst compounds, was aged for short period, The results of this study are listed in Table 2. The products of the free radical initiated polymerizations were either heavy, viscous oils or gunny, semi-solids. Upon standing in closed bottles for about two months, the soluble, radical initiated polymers cross-linked to give insoluble, infusible solids.

The infrared spectra for these polymers were all very similar,

The free radical initiated polymers showed an appreciable absorption for unsaturational The infrared spectrum of a typical, Ziegler catalyst










21


initiated polymer exhibited the following bands (cm.- ): 2980, 2900 (C-U1); 1440, 1400 (CHU2 and CHU3 deformations); 1285, 830 (Si-(Cd113)-).

Anl (Ziegler catalyzed polymer) calcd. for (C 010Si)n: C' 68,52; H, 11.50; Si,, 19.98. Found: C, 65.84; 11, 10,91; Si, 19.73.


2.- Diallyldiphenylsilane

This monomer was polymerized with both initiator systems. The results of the polymerizations are summarized in Tables 4 and 5. The polymers were all white solids and there was no apparent difference in the polymers obtained with different initiators, Polymerization was also attempted with a soluble Zieg-ler type catalyst using dicyclopentadienyltitanium dichloride in place of the titanium tetrachloride. In the several polymerization attempts made, only trace amounts of solid polymer

were obtained.

The infrared spectra of the polymers were identical and exhibited the following bands (cm. ): 3020, 2970, 8880 (C-il); 1960, 1880, 1800 (phenyl,),; 1485, 1443, 1400 (CU 2 deformations); 1428, 1111 (Si-phenyl); 1190 (Si-It).

Anal. Calcd. for (C 1020S')n: C, 81.78; H, 7,63; Si, 10,60, Found: C, 80.74; U, 7.60; Si, 10.40.


3. Diallylmethylp~henylsilane

Polymerization of this monomer was accomplished by use of the

Ziegler catalyst to give heavy oils, gummy solids, and white solids. The results of the polymerizations are shown in Table 6. The infrared spectrum of one of the solid polymers exhibited the following bands









22

(cm. ):3000, 2950,' 2875 (C-H); 1960, 1880, 1800 (phenyl); 1485, 1440, 1395 (CU2 and CH3 deformations); 1426, 1112 (Si-phenyl); 1250, 830

(Si-CUI3.

Anal,. Calcd. for (C 1Pf18Si)n: C, 77.15; Hi, 8.96; Si, 13.88. round: C, 71.60; Hi, 8.72; Si: 13.79.


4. Diallylcyclotetramethylenesilane

This monomer was polymerized with the Ziegler catalyst to give a white, solid polymer as well as some lower molecular weight material. The results of the polymerizations are shown in Table 7. The infrared spectra of polymers exhibited the following bands (cm.- ): 2950, 2900,. 2830 (C-H); 1635 weak (CH2jt-); 1455, 1400 (CH 2 deformation); 1250, 860



Anl Calcd, for (C lH20Si)n: C, 72,20; H2, 10,90; Si, 16.88. Found: C, 69.80; Il, 11.64; Si, 17,41.


5., Diallylcyclopentam~ethylenesilane

Polymerization of this monomer was accomplished by use of the

Ziegler catalyst to give vohite, solid polymers in addition to other lower molecular weight compounds. The results of these polymerizations are shown in Table 8. The infrared spectra of the polymers exhibit the following bands (cm.- ): 3030, 2800, 2800 (C-11); 1635 weak~ (CU12!C'I-); 1460, 1450, 1400 (CH 2 deformations; 915 (cyclopentamethylene silicon ring).
Anal. Calcd. for (C lH2Si)n: C, 73.23; 112 11.18; Si, 15.54. Found: C., 69.07; 11I, 10.58; Si, 15.95.









23


6. Dimethallyldiniethylsilane

Attempts to polymerize this monomer with the Ziegler catalyst gave no polymer.

Polymerization of this monomer vwns accomplished ith di-t-butyl peroxide as the initiator* The results of the polymerizations are shown in Table 9. The polymers obtained were soft, sticky semi-solids, soluble in benzene and heptane. The infrared spectra of the polymers exhibit the following bands (cm." ): 3100, 3030, 2960, 2850 (C-U1); 1640 very weak (CHI2=CH-); 1460, 1425, 1380, 1280, 980 weak, 880 weak (CU2 and CU3 deformations); 1255, 825 (-Si(CU 3)2-).

Anl Calcd, for (C 10H20Si) : C, 71.34; U, 11.97; Si, 16,68, round: C, 71.04; Up, 11.31; Si, 16.75.


7. Dimethallyldiphenyloilane

Polymerization of this monomer w~as accomplished with di-t-butyl

peroxide as the initiator. The polymers obtained were white solids which were soluble in benzene. The results of the polymerizations are shown in Table 9. The infrared spectra of the polymers exhibited the following absorption bands (cm. -1): 31 00, 3000, 2920 (C-11); 1960, 1880, 1800 (phenyl); 1460, 1380, 1300 (CU2 and al 3 deformations); 1425, 1120 (Si-phenyl); 1190 (Si-R).

Anl Calcd. for (C 2024Si)n: C, 82.12; U, 8.27; Si, 9,60. Found: C$ 80.88; Si, 8.72; Si, 9.43.









24


80. Dimethallylmethylphenylsilane

Polymerization of this monomer w-ith di-t-butyl peroxide gave a

white, benzene soluble, solid. The polymerization conditions and properties of the polymer obtained are listed in Table 9. An infrared spectrum of this polymer exhibited the following absorption bands (cm," ): 3100, 3000, 2920 (C-H; 1960$ 1880, 1800 (phenyl); 1640 very weak(C2 H) 1450, 1375, 1300 (CRU2 and.CCU3 deformations); 1425, 1120 (Si-phenyl); 1200 (Si-fl).

Anal. Calcd. for (Cl15H 24 Si) n CQ 78.18; H, 9.62; Si, 12.18. Found: Cy 76.31; HI, 9.38; Si, 12.76,


9 Dimethallylcyclopentamethylenesilane

This monomer was polymierized with the free radical initiator, di-t-butyl peroxide. A white solid was obtained which vas soluble in benzene. The results of the polymerization are shown in Table 9. The

infrared spectrum of the polymer exhibited the following bands (cm.- ): 3010, 2900, 2820 (C-H); 1640 very weak (OR 2-CH-); 1450, 1400, 130,o 1350, 46
1290 (CH 2 and CH 3 deformations); 915 (cyclopentamethylene silicon ring) .

Anl Calcd, for (C 13 R24 Si n: C, 75.64; U0, 10.74; Si, 13.60. Found: C, 73.68; H, 10.84; Si, 14.77. 10, Allyldimethylvinylsilane

Polymerization of this monom~er was attempted with both Ziegler catalysts and free radical initiators,

Ziegler catalyst polymerization gave heavy, brown oils which

could not be purified. The oils were non-volatile and would not solidify at -700, The infrared spectra exhibited the following bands (cm." ):









25

3080, 2900, 2850 (C-il0; 1635 veak, 1595 (C1I2r=CI-); 1450, 1380, 1350, 1010, 990, 950, 890 (CHI, CII 2) and CUI3 deformations); 1255, 850 (-Si(C11 3)2-)*

Polymerization was also attempted by the same method used to polymerize the ditnothallyl monomers. With 2 per cent di-t-butyl per. oxide, an oil, similar to that obtained with the Ziegler catalyst, wais isolated after two days. After four days an insoluble solid was obtained. The infrared spectra of these products vere similar to those of the oils described above*

other polymerization attempts were made using benzoyl peroxide and aja' -azobisisobutyronitrile. With benzoyl peroxide a heavy, brown oil was obtained using 5 per cent of the initiator at 700 for one week. The infrared spectrum of this oil was similar to that of the Ziegler catalyst initiated polymer except that the bands for the allyl double bond were much stronger, Attempted polymerization with 5 per cent czpal-azobisisobutyronitrile at 70 0 for one week gave no appreciable polymer. only a very small amount of heavy, non-volatile oil 'Was obtained.,

None of the products obtained could be purified to a sufficient degree for analysis.










TABLE 1

ZIEGLER CATALYST POLYMERIZATION OF DIALLYLDIMSTHYLSIIANE


Retn l~ il Moles Ast 3 Mnmr Reaction Temp. Polymer Yield Meltng Intrisicy
Hetn ~ 3 li4 Moles TiC4 MeltiRng ,nricsity

go go go g. hrs, OC. go % OCO

10 0.07 0.,08 2.1 3.0 24-96a 30-60 0 -- ---- -10 0.11 0.10 2.5 2.0 30 60 0,3 15 110-123

10 0.11 0.10 2.5 2.0 48 60 0.5 25 115-140 0,11

50 0.45 0.40 2,7 10.0 48 60 0.7 7 110-130 0.13

5o 0.52 0.50 2.5 10.0 24 85 1.0 10 110-118 0,10

apolymrzatiofls run at several temperatures and for various periods.-


N









TABLE 2

EMfCT OF C&TALYST AGING UPON THE POLYMERIZATION OF


DIALLYLDIETHYLSILANK


A t ilMoles AlEt 3 1Aging Time ile Noivoid Soidome
AE3 T~4 Moles Ti~l4 ie Liquli SoiePlyme

89. 90 hre. 90 %. go.

0.39 0.65 1.0 1 1.10 31 2.01 59

0.39 0.65, 1.0 2 0.7, 20 1.1 37

0,39 0.65, 1.0 3 1.4 40 1.5 43

0.39 0165 1.0 4 1.4 40 0.9 26

0.39 0.32 2.0 1 0.2 6 0,6 17

0.39 0.,32 2.0 2 0.3 9 0.5 14

0.39 0,16 4.0 1 0.3 9 0.9 26

o.39 0,16 4.0 2 0.4 11 0.8 23


All experiments Polymerizations


performed using 50 ml. heptane solvent and run at 8? for 24 hours.


3.5 S. diallyldimethylsilane.,










TABU. 3

FREE RADICAL POLYHERIZATION OF DIAMULYWTH~YLSILANB


Initiator Rato cier Polymer Yield o oye

%. hrs. %. o.7 ce

10 24 2 1.23 62 85-103 soft, gwumy solid

5 48 2 insoluble solid

1.2 65 3 0.3 10 804100 'white solid

2.5 60 2 0.95 47 gumm~y solid

Polymerizations performed at 1350.


Go3









TABLE 4


ZIEMLER CATALYST POLYMERIMAION OF DIALLYLDIPIENYLSILANS


Heptan. A1Et3 T1C4 Holes Ail4 Monomer Recin Polymer Yiel d Melting Intrinsic
3 4 Hols LCI4 TmeRange Viscosity

ml, 8. 8. 96 hro. 8. OC.

5 0,07 0.08 2.1 3 201.5 50 135-152
10 0.11 0.10 2,.5 48 b 1.5 30 130-140 0.06
10 0.11 0.10 2.5- 3 4,a 0.5 15
50 0.45 0.40 2.7 8 46c 2.0 25 120-135 0.065
50 0.60 0.30 4.8 10 24d 5.6 56 142-180 0.08
50 0.30 0.30 2.4 10 6Sd 1.0 10
100 0.30 0,65 111 25 45dje 13.5 54 120-140 --


*Re action
bReactioa


temperature 600.

temperature 650.


'Retio temperature 76


dae action


temperature 850.


*Catalyst aged one hour at 85o before addition of monomer.


N '0










TABLE, 5

FREE RADICAL POLY flIZAT1011 OF DIALLYWIPHENYLILANE


Reacatz ~tioe melting; Intrinuic
Intitr ie monome Polymer Yield Range Viscosity

%rs %.g 0C.

10 24 2.9 1,0 35 105-115 0.04

1.28 2.9 1.4 48 115-140 0.06

167. 6.16 3.1 50. 110-122 0.05

Polymerizations performed at 135P.


w
C










TABUZ 6


POLYwKUZATioN op I)IALLYmayLPKNYLILA


Metn oles AlZtI Reaction P1 Yld Melting Intrins icetae AM t3 Hii oles TiC4 Monomr Time Poye il, Range Viscosity

MI., 94 g. g hra. gv.%0.

50 0,60 0,33 4.5 5.0 24 trace
50 0.68 0.40 3.7 10.0 24 0.4 4 90-110 0.12
50 0.60 0.33 4.5 10.0 48 1.0 t0 95-120 -50 0.60 0.33 4.5 10.0 24 0.4 4
50 0.60 0.33 4.5 10.0 24 0.6 6 90-115 0.,07
50 0.,60 0.30 4.9 9.0 48 0.5 56 87- 95
25 0.60 0.33 4,5 10.0 48 2.6 26 98-112 0.09

Polymerizations performed- at 850.


I.'









TABJ* 7


POLYMERIZATION OF DI1LhYM0TTRAM3ffM=LE~S1LAN


Hepane A~tMoles AI~t3 Raction Yed Melting Intinsic
Retn lt3 TI11 Moles i T14 mner Time Plmr Yed Range Viscosity

Mi. g. So g hrs., go Z. OC.

50 0.45 0.20 .5.4 6.0 24 0.3 15 110-130
50 0.30 0.15 4.5 3.0 24 0.8 27 1204140 0.11
50 0.60 0.33 4,4 5.0 24 0.5 10 100-115
50 0.60 0.33 4.4 10.0 24 0,
25 0.30 Q.16 4,3 -6.0 72 A.9 48 80-100 0.05

Polymerizations performed at 8S .


N









TAB=B 8


POLYMESRIZATION* OF D1ALLYLCYGLPNTTHL9SILA=1


Repane Alt Tcl Moles Alit3 Mnmr Reaction Hli
Htae lt3 4il Moles T 014 Time Polymer Yield 'el Sn Intrinsic

Ml. g. s. gw hros. 0C,

50 0.30 0.15 4.5 4.0 48 0.5 13 80-105
50 0.07 0.40 0.5 5.0 24 trace
50 0.60 0. 30 4.8 6.0 24 0. ~ ~ -.-~
50 0.60 0.50 4.8 10,0 24 0.7 7 518 0.04
25 0.60 0.38 4.4 4.0 48 3.0 75 954110 0*04

Polymerizations performed at 850,









TABLE 9

POLYM&RIZATIONq OF DIMTHALLYLSILANES


ReactionMelting Intrinsic monomer Initiator Teo lionoiuer Polyvmer Yield Range Viscosity

%. go. go %. 0CO

Dime-thallyldimethyltilane 5 48 565 1.9 35 -o~'- .04
2.45 48 40 1.5 38
5 24 3o0' 0.35 17

Dimethallyldiphanylsilane- 5 48 4.0 3.0 75 110425 00'016
3.5 66 11.0 760 64 115-120 0.03

Dimethallylphenylmethyloilane 3 48 5.0 2.'0 40 65- 75 0.-03

Dimethallylcyclopentamthy~eneua.Lne 4 48 5,00 2.3 50 75- 90 0.04

Polymerizations performed at 1350.-














CHAPTER IV

DI$CtiSSION


Diallyl- and dimethallylsilanes were prepared by reaction of allyl or methallyl Grigiiard'reagen ts- with the appropriate dichiorosilane4 All but the cyclic silanes had been reported previously.M The reaction of ally I and rnethallyl Grigoard reagents with cyclotetramethylenedichiorosilane and cyclopentamethylenedichlorosilane gave com,pounds which could be identified as the expected products by ana).yseep molar refraction,. and infrared spectral, All of these methods gave results which are consistent with the proposed structure* The preparation method has been used previously'to yield analogous compounds* 40'41

Allyldimethylvinylsilane was prepared both by the reaction of

vinyl Grignard reagent with allyldimethylchlorosilane and by the reaction of allyl Grignard reagent with vinyldiu'ethyletboxiysilaue., The products of the two reactions were identical in their physical properties and infrared spectra, providing a definite structure proof for this compound in addition to the analysis and molar refractions The infrared spectrum

of this compound exhibits tWo41sfinctipeake for the two carbon-carbon double bonds at 1635 and 1595 cm.", he peak at 1595 cmo appears in the spectra of other vinylsilanes and can'be attributed to the vinyl group attached to silicon. 'The peak at 1635 cm., appears in all of the spectra of the allylsilanes and is assigned to the allyl double bond, This shift indicated that the carbon- carbon double bond of the vinyl group









36


is of lower energy than in that of the allyl group. This suggests a polarization of the vinyl double bond due to the presence of the silicon atom,

The polymerization of the diallyl- and dima-thallylsilanes was

accomplished by two different methods. The Ziegler catalyst twas effective for thc polymerization of the diallylsilanes uhile free radical initiators were effective for the polymerization of the dimeothallylsilanes.

All of the diallylsilanes gave solid, benzene soluble polymers

when treated ith the Ziegler catalyst. A wide variety of conditions were used in some of the polymerizations in order to obtain the best conversion of the monomer to polymer. The factors varied were: mole ratio of the co-catalyst components, reaction time, temperature, and aging time of the catalyst.

It is reported, that the aluminum triethyl-titanium tetrachloride mole ratio should be 2 or 3 to I in order to obtain the most active catalyst. it was found$ in the polymerization of diallylditnethylsilane (Table 1), that when the catalyst was not aged, the best conversion was obtained with a mole ratio of 2.5 to 1. It was found, as expected, that the conversion was increased by raising the reaction temperature from 30 to 850. The reaction time seemed to have only a small effect upon the yield of polymer obtained,

The effect of aging of the catalyst upon the conversion to polymer vas studied for the polymerization of diallyldimethylsilane (Table 2). It is reported 54that the aging of the catalyst decreases its activity. It vras found that the aging of the catalyst actually increased the conversion of this vonomer to solid) linear polymer. The best conversion









37

was obtained with a co-catalyst mole ratio of I. to I and a one hour aging time for the catalyst. The conversion dropped off slowly as the catalyst was aged for a longer period.

In the polymerization of diallyldiphenylsilane it vas found that the mole ratio of the co-catalyst components had a smaller effect upon the conversion, between mole ratios of 2.2 and 4.4 to I. (Table 4). With this monomer the temperature and reaction time seem to have only a small effect upon the conversion.

In some polymerizations of diallyldiphenylsilane, titanium tetrachloride was replaced in the catalyst by dicyclopentadienyltitanium dichloride, to give a soluble Ziegler type catalyst. Diallyldiphonylsilane vas chosen for these experiments due to the fact that good yields of solid polymer had been obtained in previous polymerizations of this monomer with the conventional Ziegler catalyst. only small amounts of solid polymer were obtained with the soluble catalyst mixture, Natta 5 has reported that this soluble catalyst is less active than is the conventional catalyst.

Polymerization of the remaining diallylsilanes was accomplished with the conventional Ziegler catalyst. Conditions for these polymerizations wore not significantly varied and no attempts were made to obtain optimum conditions for the polymerizations.

Attempts were made to polymerize dime thal lyldimethyls ilane with

the Ziegler catalyst but no polymer was isolated, This was not surprising in view of previously published reports of attempts to polymerize olefins with branching close to the double bond. 52









38


rree radical polymerization of the ditnethallylvilanes led to

soluble polymers (Table 9). Di-t-butyl peroxide was used as the initiator for these polymerizations, Diallyldirnethylsilane (Table 3) and diallyldiphenylsilane (Table 5) were also polymerized trith this initiator,,

Lower melting points and lower intrinsic viscosity values for

these free radical initiated polymers indicate that the polymers are of lower molecular weight than are those obtained with the Ziegler catalyst. The dimethallylsilanes all have very low intrinsic viscosities which indicate that they have a low degree of polymerization. The low degree of polymerization is probably due to I"degradative chain transfer" involving the allylic hydrogen atoms. In the dimethallyloilanes, this effect should be more important due to the greater number of allylic hydrogens. Diallylsilanes have four allylic hydrogens while the dimethallylsilanes have ten. Comparison of the results of the free radical polymerization of diallyldiphenylcilane (Table 5) and of dimethiallyldiphenylsilane (Table 9) shows that although both have low intrinsic viscosity values, those for the diallyl polymers are about twice those for the dirnethallyl polymers, Since these compounds are very similar it seems likely that the molecular weights for these two polymers would be in about the same ratio as are their intrinsic viscosities.

All of the diallyl- and dixuethallylsilanes gave polymers which were soluble in benzene although small fractions of a few polymers were insoluble. These soluble polymers exhibited little or no residual unsaturation in the infrared spectra, In most cases the absorption bands








39


for carbon-carbon double bond stretch and for terminal methylene deformations could be removed from the spectra by further purification of the polymer.

The analytical results of the polymers are in many cases rather

far from the theoretical value for carbon. It is reported,.* that in the analysis of silicon polymers, combustion of the sample may lead to the formation of some silicon carbide which to not completely oxidized. The formation of this compound would account for the low per cant of carbon found in the analyses of these polymers. The per cent silicon would not be affected by this due to the fact that the silicon analyses are performed on a separate sample using wet oxidation methods. The silicon and hydrogen analyses of these polymers are fairly cloe* to the theoretical values and it seem certain that the formulae assigned to the polymers are correct.

Since these polymers are soluble and contain no residual unhaturarton, it is fairly certain that they contain cyclic recurring units as represented below,







111

a'ff - ft3 Cfl








40


Diinethallyloilanee







QICH
2
2
I -C c3," c6i5

R c3~~Ce3i

in view of the properties of these polymer$ and the previous work reported211'1 on the polymerization of 1,6-dienes, these structures

are the most likely ones for. these polymes

The polymerization of allyldimethylvinylailane was attempted with several catalysts but no solid,. soluble polymer was obtained, The polymertzation with free radical initiators gave varying results. With di-t-butyl peroxide both an insoluble solid and a heavy oil were, obtained. The infrared spectra were very similar and showed absorption for both ally). and vinyl groups, The allyl double bond absorption was decreased a great deal in the two polymers however. Benzoyl peroxide gave a low yield of heavy oil which had an infrared spectrum similar to thatt of the polymersabove. Use of ,ci'l-azobisisobutytonitrile gave no polymerizeit has been reported that vinylsilanes do not polymerize with bensoyl peroxide.57 The reason for this lack of polymerization can be explained by consideration of the radical which would be formed by a free radical attack on a vinylsilane.










Z + CHz-ce2 T


Xt has been mentioned earlier in this section that there is a polarization of the vinyl group attached to silicon. This polarization is due to the "electron sink" effect of silicon. This "electron sinVI effect would stabilize the free radical formed above, This radical stability i's apparent in the free radical chlorination of tetraalkylsilenes.5 Th chlorination of tetraethylsilane gives the z-chloro, compound exclusively, This indicates that the radical on a carbon atom adjacent to a silicon atom of a tetraalkylsilane is very stable* The stability of this radical may account for lack of polymerization of allyldimethylvinylsilane. Thel low molecular weight polymers, which did result from this monomer were probably formed by polymerization through the allylic double bonds, This type of polymerization leaves a vinyl group on the chain which may, under proper conditions# react to form a crosslink leading to insoluble polyMert*

Attempts to polymerize this monomer by use of Ziegler catalysts Save results similar to those obtained with free radical initiators. In this case the vinyl double bond does not take part in the polymerization due to eteric factors. The allyl double bond undergoes polymerization, however, to give low molecular weight oils, It was not possible to purify the polymers obtained with this monomer to Any large extent due to the fact that the polymers were non-volatile and liquid at even very low

temperatures. infrared spectra, however, indicate that the only major changes from the monomer ts the decreaseof allyl double bond content in the polymer,


41















CHAPTER V

SUMMARY


A series of diallyl- and dimethallylsilanes were prepared by the reaction of allyl or methallyl Grignard reagents Iwith the appropriate dichlorosilanes, Three of these monomers had not been previously reported. Allyldimethylvinylailane was prepared by two different routes.

The diallylsilanes were converted to polymers by use of Ziegler

catalysts. The polymers were soluble in benzene,'and showed little or no unsaturation in the infrared .spectra. A study was made of the effect of aging time of the catalyst upon'the polymerization of diallyldimethylsilane. it was found that increased yields of polymer were obtained when the catalyst was aged for short periods before the addition of the m~imer.

The dimethallylsilanes were polymerized by use of thelfree radical initiator di-t-butyl peroxide to give benzene soluble polymers containing little residual unsaturation. Intrinsic viscosity measurements indicate that the Ziegler catalyst initiated polymers have a higher degree of polymerization than do the free radical initiated polymers.

in view of the physical properties of these polymers it weas concluded that the monomers were polymerized by the intramolecular-intermolecular chain propagation mechanism to give polymers containing cyclic recurring units.

Polymerization of allyldimethylvinylsilaie gave low molecular weight polymers with both Ziegler catalyst'and f ree radical initiators.


42








43

The infrared spectra indicate that polymerization occurred through the carbon-carbon double bond of the allyl group only leaving the unreacted vinyl groups an the polymer chain,












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BIOGRAPHICAL ITEMS


Robert W, Stackman was born in Dayton, Ohio, on June 29, 1935. He entered-the University of Dayton, Dayton, Ohio, in September 1953 and received the degree of Bachelor of Science, 'with a major in Chemistry in June 1957.

in September of 1957 he entered the Graduate School of the University of Florida, He has been employed by the Chemistry Department of the University of Florida as a graduate assistant, .and as a research assistant,

SIIHe is a member of Alpha Chi'Sigma fraternity and the American, ChemicalSociety.


48












This dissertation was prepared under the direction of the chairman of the candidate's supervisory committee and has beeu approved by all. members of that committee, It was submitted to the Dean of the College of Arts and sciences and'to the Graduate Counil, and was approved as partial fulfillment of the requirements for the degree of Doctor of Philosophy.



January 28,. 1961



Dean, College of Arts a~d flciences




Dean, Graduate School Sup.rqsr Committee:



Chairman











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describe
'1410' 'info:fdaE20090811_AAABGAfileF20090811_AABVZD' 'sip-files00006.txt'
144e0574b2471e653de33dc7d5f61583
1639060f3a9c0b17322ed1383b42b7de8d38592a
describe
'6188' 'info:fdaE20090811_AAABGAfileF20090811_AABVZE' 'sip-files00006thm.jpg'
9eba63d3993becbd0d25496587e8ba0e
68777ed8d2d20db7ac4b48a85d6a1f4d6c320835
'2012-03-13T08:09:06-04:00'
describe
'150837' 'info:fdaE20090811_AAABGAfileF20090811_AABVZF' 'sip-files00007.jp2'
8d6cec2f7384aeab3c7acd0486e6c040
1d857ab11725761e4e23de7cbc6da6d1247f5b94
describe
'93986' 'info:fdaE20090811_AAABGAfileF20090811_AABVZG' 'sip-files00007.jpg'
48a575e9c18f2efd936b5fa33e77a40e
8e403cd7da4353e4e9a5706c82c13f81a52d57f4
describe
'46913' 'info:fdaE20090811_AAABGAfileF20090811_AABVZH' 'sip-files00007.pro'
04377d2485fda00463c558eeef3323c0
36c309f4c2758578a732fef1a96c17d515cc520e
'2012-03-13T08:10:24-04:00'
describe
'32657' 'info:fdaE20090811_AAABGAfileF20090811_AABVZI' 'sip-files00007.QC.jpg'
62bf90365c396ec2ae43b6782cda030b
0625cd6ff6a96799115169164e38cc7e06d425a1
'2012-03-13T08:09:33-04:00'
describe
'999852' 'info:fdaE20090811_AAABGAfileF20090811_AABVZJ' 'sip-files00007.tif'
005abefc6f9c93fadd2ac043aac0fe86
edfd0604fc2585b7415adb12a8cfae853324abaf
'2012-03-13T08:11:29-04:00'
describe
'1866' 'info:fdaE20090811_AAABGAfileF20090811_AABVZK' 'sip-files00007.txt'
294c715ec734022aa916c7289e70bc0d
7e5c5b3f0313c91c09078f731bca1899ff504edc
'2012-03-13T08:11:20-04:00'
describe
'9091' 'info:fdaE20090811_AAABGAfileF20090811_AABVZL' 'sip-files00007thm.jpg'
aa5fe38e804dcca2f2e4cc945173f9fa
f53a4712d15622a3e0f8bd143b279965a8d4a530
'2012-03-13T08:09:02-04:00'
describe
'984545' 'info:fdaE20090811_AAABGAfileF20090811_AABVZM' 'sip-files00008.jp2'
4058b777c21ccc61c8c3e7de0f1976a1
f9b5d35f1014f57520bb59f8fd7edfb6365a9681
'2012-03-13T08:09:31-04:00'
describe
'99925' 'info:fdaE20090811_AAABGAfileF20090811_AABVZN' 'sip-files00008.jpg'
b3f3ea53f71940c6b43f0cd5171aa4b5
dcce179a917fdc6845bc5418becf128ae5849e76
'2012-03-13T08:09:08-04:00'
describe
'49366' 'info:fdaE20090811_AAABGAfileF20090811_AABVZO' 'sip-files00008.pro'
97c9e5d65018b566190dca85f556a371
55785db074c4c19179312c130cf078d657ca5082
'2012-03-13T08:10:14-04:00'
describe
'33302' 'info:fdaE20090811_AAABGAfileF20090811_AABVZP' 'sip-files00008.QC.jpg'
c1cfdef399a70f7524f6870c08721cae
eede793eab23cacfa25c64129391d0c991e639fd
'2012-03-13T08:10:57-04:00'
describe
'7899004' 'info:fdaE20090811_AAABGAfileF20090811_AABVZQ' 'sip-files00008.tif'
1d11cca4db245f93a98fe03031dbbcc4
3008e3fdd4f3f7684b94104926efe87a44d7507e
'2012-03-13T08:11:46-04:00'
describe
'2025' 'info:fdaE20090811_AAABGAfileF20090811_AABVZR' 'sip-files00008.txt'
11441c444e0ae610412559e07cf465c0
abc0d83adc86c84f1150b26d4d5bcbb51995c0fa
'2012-03-13T08:10:18-04:00'
describe
'8602' 'info:fdaE20090811_AAABGAfileF20090811_AABVZS' 'sip-files00008thm.jpg'
4904d3ed77b641f3dcdb9841c8c286fb
960d899e55e222cab428e6a15d9b53e47f3bb656
'2012-03-13T08:10:32-04:00'
describe
'123928' 'info:fdaE20090811_AAABGAfileF20090811_AABVZT' 'sip-files00009.jp2'
5b4f0111a52716329e2efa7d7eab30a1
cf81402419a89e17a01de2168cc21257fd349cbd
'2012-03-13T08:09:23-04:00'
describe
'84198' 'info:fdaE20090811_AAABGAfileF20090811_AABVZU' 'sip-files00009.jpg'
1aa27581a34ac9fe7c59fd79fab5781d
78da0e76b02478aac2197e7295b08a18209e4f27
'2012-03-13T08:10:37-04:00'
describe
'43269' 'info:fdaE20090811_AAABGAfileF20090811_AABVZV' 'sip-files00009.pro'
024d87851e9e153479947422c97de643
6c9f2ce7c1e690ee9714bd13cc726b9c8bdc8dc8
describe
'28711' 'info:fdaE20090811_AAABGAfileF20090811_AABVZW' 'sip-files00009.QC.jpg'
1a56c6aa3dc140c9cec135904877367d
67ca96a4ba5d1889ecb652e80481506689bbbc44
'2012-03-13T08:10:39-04:00'
describe
'972415' 'info:fdaE20090811_AAABGAfileF20090811_AABVZX' 'sip-files00009.tif'
7346c92847596292ef11483e3a3a8b69
f1d151fd680c1db31fab8af16e58f686d30c108d
'2012-03-13T08:09:32-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1769' 'info:fdaE20090811_AAABGAfileF20090811_AABVZY' 'sip-files00009.txt'
9e404b4f78163b86e3453d8ac5d2f299
8678ab64ad79965c728dfd8eeab188896f6eb07a
describe
'8145' 'info:fdaE20090811_AAABGAfileF20090811_AABVZZ' 'sip-files00009thm.jpg'
b787ff0f2028e39e5fdd53c15e060d07
7a3277dc30f75a936a625a2e246bb3688ba4fe68
'2012-03-13T08:09:07-04:00'
describe
'133433' 'info:fdaE20090811_AAABGAfileF20090811_AABWAA' 'sip-files00010.jp2'
4b24e691989fadc94b8672a2d559564a
78316b86d426d43c797efdc8b5acab526a3fa1d7
'2012-03-13T08:09:18-04:00'
describe
'90524' 'info:fdaE20090811_AAABGAfileF20090811_AABWAB' 'sip-files00010.jpg'
708dd862c0120dc3e8a55381482fefde
2f61ad7bf1703a5a2cf9e994d7a53d6cbdcdeea3
describe
'45712' 'info:fdaE20090811_AAABGAfileF20090811_AABWAC' 'sip-files00010.pro'
7187dec4699f535395c27968cd873c4d
5e7129d070db434172d2bae76b92b363d0902069
'2012-03-13T08:11:35-04:00'
describe
'31463' 'info:fdaE20090811_AAABGAfileF20090811_AABWAD' 'sip-files00010.QC.jpg'
2afd6368744c713723d8c0133b957c0b
0ab59aab44d7ddeb7bea07f0a08983ad63fdcaa3
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWAE' 'sip-files00010.tif'
1aee4add5191a66bec0c7f701f5508b3
66e1531caabd3dd3de77b381af63c42d547351ec
'2012-03-13T08:10:19-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1942' 'info:fdaE20090811_AAABGAfileF20090811_AABWAF' 'sip-files00010.txt'
8dec372cb75598ecc8a1340eb866f61a
d68b274b2b677a4004517f6a213fde33b2f64c86
'2012-03-13T08:10:49-04:00'
describe
'8792' 'info:fdaE20090811_AAABGAfileF20090811_AABWAG' 'sip-files00010thm.jpg'
67752bcb92f21f07172a7a362d270513
8c462dd1c56204f21df04bce1cd07bd4397a8cfa
'2012-03-13T08:10:48-04:00'
describe
'63730' 'info:fdaE20090811_AAABGAfileF20090811_AABWAH' 'sip-files00011.jp2'
8441219a3319768311fc91d306c187c0
112d6fe457a8d0901bda83e82c79fec89375a646
'2012-03-13T08:11:36-04:00'
describe
'43933' 'info:fdaE20090811_AAABGAfileF20090811_AABWAI' 'sip-files00011.jpg'
0149b66ef25f31885af687ecbd815971
2f90a1be1a18040b2174f8a185b9f496840d6154
'2012-03-13T08:09:20-04:00'
describe
'19671' 'info:fdaE20090811_AAABGAfileF20090811_AABWAJ' 'sip-files00011.pro'
c50449f4254ad798137abe5235158e5f
3433d84bc6ac342a90a58914a27adad54cfd5445
'2012-03-13T08:09:03-04:00'
describe
'14733' 'info:fdaE20090811_AAABGAfileF20090811_AABWAK' 'sip-files00011.QC.jpg'
07b4b963462690a4385edce1ec85b23f
6c053d0d94b5e6b215ad2354166ea3426684a262
'2012-03-13T08:11:05-04:00'
describe
'997736' 'info:fdaE20090811_AAABGAfileF20090811_AABWAL' 'sip-files00011.tif'
a6f4d85bd8ff942b4c6f4d66fb7cc5e2
4e20d94f678e8eaaa2f7e01cade5fd3d876b5d68
'2012-03-13T08:11:49-04:00'
describe
'962' 'info:fdaE20090811_AAABGAfileF20090811_AABWAM' 'sip-files00011.txt'
7d4de4f81fc78a1f8d80df4fe2eb62ee
707be96aa8659357746c91da3be489f790d422b3
'2012-03-13T08:11:13-04:00'
describe
'4490' 'info:fdaE20090811_AAABGAfileF20090811_AABWAN' 'sip-files00011thm.jpg'
df5faa69a6089c5b602b6497b741c4aa
4ac775366e6cc4fca3fe88672285deee1f9b04a3
describe
'986359' 'info:fdaE20090811_AAABGAfileF20090811_AABWAO' 'sip-files00012.jp2'
0afb04296855c34b98f3dd2efa646201
37b05a4667b2ac8e8eb9d73c33eda9ad82cb83c1
'2012-03-13T08:09:39-04:00'
describe
'73922' 'info:fdaE20090811_AAABGAfileF20090811_AABWAP' 'sip-files00012.jpg'
e36e0e80c3d7f4270987eeab7fe363f8
fc32f0232d2e0a030ea881287d92eb8a31548b45
describe
'35611' 'info:fdaE20090811_AAABGAfileF20090811_AABWAQ' 'sip-files00012.pro'
54592986018fb08e8e3257278404fba9
920de23451c4c3f4ccf195b587b5c8c59403a8d8
'2012-03-13T08:09:28-04:00'
describe
'24030' 'info:fdaE20090811_AAABGAfileF20090811_AABWAR' 'sip-files00012.QC.jpg'
4f0001a7b21d0c615e3f5fa3d6868aa6
2937190620ea1e8effc4857ce1e9a92e5cd4ecbf
'2012-03-13T08:10:26-04:00'
describe
'7908756' 'info:fdaE20090811_AAABGAfileF20090811_AABWAS' 'sip-files00012.tif'
d4babda1a086639ddb710eb34f04b166
8bbb4ee8ec0439949e2a18b2171f0ca325c975f5
'2012-03-13T08:11:25-04:00'
describe
'1554' 'info:fdaE20090811_AAABGAfileF20090811_AABWAT' 'sip-files00012.txt'
6c3f82154516ef6f77497339851e4a2e
e0b166dfb7e2c42e22d03a1ae03c03102a802005
'2012-03-13T08:08:52-04:00'
describe
'6721' 'info:fdaE20090811_AAABGAfileF20090811_AABWAU' 'sip-files00012thm.jpg'
592a0b48222283e4a98d188c91c53a07
39829bb445fd8f108d2fd374df23d5800f21a874
'2012-03-13T08:09:14-04:00'
describe
'994525' 'info:fdaE20090811_AAABGAfileF20090811_AABWAV' 'sip-files00013.jp2'
f828e56ea2fb3ba246b3ce2a9a805764
b7e138ce46b47bb92d6607168401e97a069c3d4c
'2012-03-13T08:08:57-04:00'
describe
'76317' 'info:fdaE20090811_AAABGAfileF20090811_AABWAW' 'sip-files00013.jpg'
55a6049f5a9c52443a0100f1c76693e2
2e7bebc17667c7bb3e642ee47df680557339a181
'2012-03-13T08:10:33-04:00'
describe
'34505' 'info:fdaE20090811_AAABGAfileF20090811_AABWAX' 'sip-files00013.pro'
eff37204473ed13140b2811794695eb0
b081409e6cf5f27b7eff491126c66729beafba44
'2012-03-13T08:10:25-04:00'
describe
'26012' 'info:fdaE20090811_AAABGAfileF20090811_AABWAY' 'sip-files00013.QC.jpg'
a481669654aa6d65ea3845f5d9bb8602
ef7f65b5877b472036467473594ae5829b35665c
describe
'7977284' 'info:fdaE20090811_AAABGAfileF20090811_AABWAZ' 'sip-files00013.tif'
29725aa3bf1012b1989c1adf6dadd645
2ae5344fc5c74dcefd705168a3d30ad2e99d3a99
'2012-03-13T08:09:41-04:00'
describe
'1457' 'info:fdaE20090811_AAABGAfileF20090811_AABWBA' 'sip-files00013.txt'
dc5137e04e9f09e9dffccaf2089a0bf0
9c0fa9a24f9584884bc6e1639faf7dc2f8bb808e
'2012-03-13T08:10:06-04:00'
describe
'7571' 'info:fdaE20090811_AAABGAfileF20090811_AABWBB' 'sip-files00013thm.jpg'
ceac3f59633d9dae749cbd215e73af8a
dc1a073b73a0fa71ff8d616b1f82957de8729682
'2012-03-13T08:11:07-04:00'
describe
'118462' 'info:fdaE20090811_AAABGAfileF20090811_AABWBC' 'sip-files00014.jp2'
bb273d98526ce5e9c44aa44a30b75069
080126b6bfbce8e8eb0a65d969b60694235659e1
'2012-03-13T08:11:24-04:00'
describe
'81940' 'info:fdaE20090811_AAABGAfileF20090811_AABWBD' 'sip-files00014.jpg'
9fb65371c7d89a6b710708d1a8c44fbe
a62926d738acafc98e098c19aaf9036a36f850bf
describe
'41038' 'info:fdaE20090811_AAABGAfileF20090811_AABWBE' 'sip-files00014.pro'
a4c23a3f815ba6fb75d30c8268e4c8ac
7c0d2b41de5665d9b5b6706df6441f352540a21c
'2012-03-13T08:09:44-04:00'
describe
'29595' 'info:fdaE20090811_AAABGAfileF20090811_AABWBF' 'sip-files00014.QC.jpg'
87ff6e464def654e36dfc03ada50bcba
eded5f58a7102ce016ddbfb102b71540471dba5c
'2012-03-13T08:09:22-04:00'
describe
'969186' 'info:fdaE20090811_AAABGAfileF20090811_AABWBG' 'sip-files00014.tif'
8732a578a0a02e209798f58f651be3af
6b2a6fa6f690c96b8e9d9357b4cf9cba9706beb7
'2012-03-13T08:11:01-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1668' 'info:fdaE20090811_AAABGAfileF20090811_AABWBH' 'sip-files00014.txt'
ba0cb133694ea016d3aff648ceeb8439
1dd6cff6b8999d56701729bbce2f4ad7ab5f19b5
'2012-03-13T08:09:54-04:00'
describe
'8152' 'info:fdaE20090811_AAABGAfileF20090811_AABWBI' 'sip-files00014thm.jpg'
bc87c8724bfa62025cb0ddd238070805
9544a3d56adfa69f81cb4f0523f95ab96890d1d9
describe
'133775' 'info:fdaE20090811_AAABGAfileF20090811_AABWBJ' 'sip-files00015.jp2'
4def4ac60aea92b16b69265e4dcb21ef
60909244259dd5d78778200a56e2851af661505d
'2012-03-13T08:09:15-04:00'
describe
'90641' 'info:fdaE20090811_AAABGAfileF20090811_AABWBK' 'sip-files00015.jpg'
2ca5fc761e4425b31806a666b52f8192
233639a6979ad7ea2788f91fba4b2426173794ba
'2012-03-13T08:11:31-04:00'
describe
'43002' 'info:fdaE20090811_AAABGAfileF20090811_AABWBL' 'sip-files00015.pro'
2f72adddc10f342e51e51fdf6748c223
3a923a6e5d05f71a4969fa9d8f16fd8c249ffcbb
'2012-03-13T08:10:10-04:00'
describe
'32351' 'info:fdaE20090811_AAABGAfileF20090811_AABWBM' 'sip-files00015.QC.jpg'
a7df97323425e443aa4efc73dde0b3f0
ae667c9bf6a1f608bc0279c9628cd9a18fbb0c9a
'2012-03-13T08:10:00-04:00'
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWBN' 'sip-files00015.tif'
a3669499e5ed3d76c40fb52fe8e4ac08
e1602041b147d4083586ec10950ecb3efd5144c1
'2012-03-13T08:11:22-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1694' 'info:fdaE20090811_AAABGAfileF20090811_AABWBO' 'sip-files00015.txt'
397a78b2135fc3cc1a1fe6948f0454b4
242682056db3d9318a31b9c4625841d8617d0f25
'2012-03-13T08:10:44-04:00'
describe
Invalid character
'8652' 'info:fdaE20090811_AAABGAfileF20090811_AABWBP' 'sip-files00015thm.jpg'
43d087bcef498f98926385be59e709e6
a156e149fbc0b0bfc060004773d9ac2c97fe760c
describe
'988818' 'info:fdaE20090811_AAABGAfileF20090811_AABWBQ' 'sip-files00016.jp2'
48a22655d64af51b3d596c177971e8bf
ea9a46c3012b5c78a6e9987e9ce578d59cd99de0
describe
'91904' 'info:fdaE20090811_AAABGAfileF20090811_AABWBR' 'sip-files00016.jpg'
0217ddcb7d5c2f8d9cc86108b1fc8c16
5901e590e18ded677c686db334c6c024d43d23e3
'2012-03-13T08:11:04-04:00'
describe
'41239' 'info:fdaE20090811_AAABGAfileF20090811_AABWBS' 'sip-files00016.pro'
fa929ba0a28475035b6426c1f08b732e
3f5b7e48bd7cdbb4c9a8295e2c91dec28195a7af
'2012-03-13T08:11:47-04:00'
describe
'29678' 'info:fdaE20090811_AAABGAfileF20090811_AABWBT' 'sip-files00016.QC.jpg'
8a1ea3170f2c2a6986e303cc7908ac25
bc5c9a537269ec52de7b31f8097f2a7d1cd6205d
describe
'7931432' 'info:fdaE20090811_AAABGAfileF20090811_AABWBU' 'sip-files00016.tif'
61af6d743f41647c22cb4710a98631f3
079dc46c960227dd4550f95ba393be4c8023ba63
describe
'1653' 'info:fdaE20090811_AAABGAfileF20090811_AABWBV' 'sip-files00016.txt'
c40b79213122c71ec55bffc21dd2162b
47dfdd7a3cc684e5903527fabf91178d8c35605e
describe
Invalid character
'7802' 'info:fdaE20090811_AAABGAfileF20090811_AABWBW' 'sip-files00016thm.jpg'
4c45441bead5d93f7d35e6db8de5e68c
1d4608eee9c08cfc9e4d20eb90d5ade1586cde96
'2012-03-13T08:09:30-04:00'
describe
'134382' 'info:fdaE20090811_AAABGAfileF20090811_AABWBX' 'sip-files00017.jp2'
d6ab59e1375ce6e47a01a35a2fe5250c
8e0d82e4fc8b876679960f2bcebd03829dd11d2c
'2012-03-13T08:10:59-04:00'
describe
'88510' 'info:fdaE20090811_AAABGAfileF20090811_AABWBY' 'sip-files00017.jpg'
453ecf18575c1d203fcb3ef14543f0b9
dc44379e5cfc044cb72b3949544ce9d4c96ceb53
describe
'42775' 'info:fdaE20090811_AAABGAfileF20090811_AABWBZ' 'sip-files00017.pro'
42df021c5c178592753961c588fd44dd
2362504a6dc9328ec7977086061edce8d688a8ef
'2012-03-13T08:10:54-04:00'
describe
'30816' 'info:fdaE20090811_AAABGAfileF20090811_AABWCA' 'sip-files00017.QC.jpg'
7658c3346963cff6c7118601bf72e846
3028279036f4d00738d5975a129c2988513ddcdf
'2012-03-13T08:10:53-04:00'
describe
'968586' 'info:fdaE20090811_AAABGAfileF20090811_AABWCB' 'sip-files00017.tif'
739ef2b6de3c93b519d09e29fc36d8df
8051df65cf68ec9a6d105620187760471d9ef49f
'2012-03-13T08:10:55-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1776' 'info:fdaE20090811_AAABGAfileF20090811_AABWCC' 'sip-files00017.txt'
3996d16e0e015cc23d7eed77876ab6e9
ba7d6de2c68c01c593be5cec816c75033c5e137b
'2012-03-13T08:09:00-04:00'
describe
Invalid character
'8276' 'info:fdaE20090811_AAABGAfileF20090811_AABWCD' 'sip-files00017thm.jpg'
4fe0816e283e76d895ec557f9f0ecad5
2860ad863febe7c2afe24c85ad1b7515e7eb1130
'2012-03-13T08:11:27-04:00'
describe
'131931' 'info:fdaE20090811_AAABGAfileF20090811_AABWCE' 'sip-files00018.jp2'
f7f9e33a772f4929170aebd9c79fae80
41162271e31225025da9513e90bd8e2fcdfaf81d
'2012-03-13T08:10:13-04:00'
describe
'91733' 'info:fdaE20090811_AAABGAfileF20090811_AABWCF' 'sip-files00018.jpg'
f957e763be81a0ba8d9823c8e922782d
a10a43326dbee6a0d02c26bff5973836685a14e9
'2012-03-13T08:10:31-04:00'
describe
'44515' 'info:fdaE20090811_AAABGAfileF20090811_AABWCG' 'sip-files00018.pro'
99105aa1c0fa843b591b9265416bf5a9
32ac89329ab227c51976bbe8aa8e86ec0f8d951b
'2012-03-13T08:11:42-04:00'
describe
'32754' 'info:fdaE20090811_AAABGAfileF20090811_AABWCH' 'sip-files00018.QC.jpg'
69f587ed027e1aa8be1207321d3af12c
ed4e482459ed8802e5ed3aefaefae0792d800585
'2012-03-13T08:09:11-04:00'
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWCI' 'sip-files00018.tif'
2a5be8e71d478b2f855335427b25897a
c07915b80f3994e7345da82506ebed77ce2eb5f9
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1917' 'info:fdaE20090811_AAABGAfileF20090811_AABWCJ' 'sip-files00018.txt'
aa0cc17e5c5d8422a913685dd8ad83b7
e20bb29839f28e700c706fdb889b0e9c03b6773a
'2012-03-13T08:09:24-04:00'
describe
Invalid character
'8374' 'info:fdaE20090811_AAABGAfileF20090811_AABWCK' 'sip-files00018thm.jpg'
bcd678f97ab4d99fd7969a3164243278
6208d7fb71fedc0706b15e6c9c7bae88b5230a64
describe
'126263' 'info:fdaE20090811_AAABGAfileF20090811_AABWCL' 'sip-files00019.jp2'
a9b6497b88ffbc465ad5b91dd4986e33
a021ea5d4fa42d767f97cbf6e271aa067c30e7f6
'2012-03-13T08:11:23-04:00'
describe
'88462' 'info:fdaE20090811_AAABGAfileF20090811_AABWCM' 'sip-files00019.jpg'
1b7836ff1cc9b21114c68b89376c26ec
3f0f482eaf1fb341900620c09aeb3e01bb45d70a
'2012-03-13T08:11:37-04:00'
describe
'44183' 'info:fdaE20090811_AAABGAfileF20090811_AABWCN' 'sip-files00019.pro'
fd6094429e15d2f091d3575b9d3cae7f
93447d1740f104aca0b14a191944a0c49006909f
'2012-03-13T08:09:37-04:00'
describe
'31484' 'info:fdaE20090811_AAABGAfileF20090811_AABWCO' 'sip-files00019.QC.jpg'
e0e607bc118a18ed0bc25dd0bcd50721
5a31309214d094842796a198cc072401e9bd7a46
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWCP' 'sip-files00019.tif'
18e06127d3f0a2f97c601ed4b6e3f532
790d32f97b93ca9988e58e6cfd4c394540b795c2
'2012-03-13T08:11:18-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1840' 'info:fdaE20090811_AAABGAfileF20090811_AABWCQ' 'sip-files00019.txt'
da5a5c7000456215e1a22b6d1532c3d7
6d4292be1ecf9d997e153f0fda42896243e26ce4
describe
'8200' 'info:fdaE20090811_AAABGAfileF20090811_AABWCR' 'sip-files00019thm.jpg'
c2712f42915e2c491080b67150ee9c74
451c3f1a0a65d5887a96deae7e4b26259a5fe3f4
describe
'57108' 'info:fdaE20090811_AAABGAfileF20090811_AABWCS' 'sip-files00020.jp2'
57cbef5a91ee74ba71beb2a2085e822e
27f057583537050f26ef5358c86628fce60988ef
'2012-03-13T08:10:02-04:00'
describe
'40746' 'info:fdaE20090811_AAABGAfileF20090811_AABWCT' 'sip-files00020.jpg'
0c2e36db6ad0cb3f9cb3d6a4da3ccc23
2cf2b97c831046a8a55af507b5b9a81576b589f1
describe
'17280' 'info:fdaE20090811_AAABGAfileF20090811_AABWCU' 'sip-files00020.pro'
4a06a52754ff350d5ada23e945fc8ee2
7d554bbf1025a5c14843463b9bb8727d75d8964e
describe
'14241' 'info:fdaE20090811_AAABGAfileF20090811_AABWCV' 'sip-files00020.QC.jpg'
bcef1884a6cbf76b11442e80517da955
970b3d9abc4efe326ff9360b80c531b933ff0dec
'2012-03-13T08:09:55-04:00'
describe
'982516' 'info:fdaE20090811_AAABGAfileF20090811_AABWCW' 'sip-files00020.tif'
c5f4d1965c97787d07401d57b247af90
56e61beda1f3b250e74373f44444f9efc27ab21e
describe
'782' 'info:fdaE20090811_AAABGAfileF20090811_AABWCX' 'sip-files00020.txt'
64b90f03d8eb0ead3ea9a865edeb556b
d013cf223cc73f51415843169fde889e41ac4289
describe
'4179' 'info:fdaE20090811_AAABGAfileF20090811_AABWCY' 'sip-files00020thm.jpg'
b4fc48ad7826cba037582f58fbe06caa
58480ee18d210bda6605a45f8ced7f3a8ee3691d
'2012-03-13T08:08:40-04:00'
describe
'978859' 'info:fdaE20090811_AAABGAfileF20090811_AABWCZ' 'sip-files00021.jp2'
baa1d23a81207115fe3388b11c63d1f9
5f45a8ac58ced8cfe64b9d6d2463d56581ceff53
describe
'83264' 'info:fdaE20090811_AAABGAfileF20090811_AABWDA' 'sip-files00021.jpg'
a922b6a2362b59baba5b21bad69a1ff0
ec0050612f3394ac3ae8ee77c103169f8ce03f86
describe
'39418' 'info:fdaE20090811_AAABGAfileF20090811_AABWDB' 'sip-files00021.pro'
bf9c4aa40b3a277c75a08e5661ce0aa0
77154005755e8834079ed3df4696a8f70fc5c91d
'2012-03-13T08:11:44-04:00'
describe
'28797' 'info:fdaE20090811_AAABGAfileF20090811_AABWDC' 'sip-files00021.QC.jpg'
882027a884adfd318dbac9a112fc439d
abba506fbbcf38501add7088935f8d8e4f761966
'2012-03-13T08:08:43-04:00'
describe
'7850864' 'info:fdaE20090811_AAABGAfileF20090811_AABWDD' 'sip-files00021.tif'
f6335f90df7725e7b994c0eb77ac2cce
b6235e5264b774ebf27421e62480b9057c4e2906
'2012-03-13T08:11:17-04:00'
describe
'1675' 'info:fdaE20090811_AAABGAfileF20090811_AABWDE' 'sip-files00021.txt'
797dae967e1afaa69f6966df52412b84
3b0e04831fd66244e9516a7b900705e3a3f67cb8
'2012-03-13T08:10:22-04:00'
describe
'7689' 'info:fdaE20090811_AAABGAfileF20090811_AABWDF' 'sip-files00021thm.jpg'
12185f107669a30a0e46faff26529ddc
03333fe266fca9085907fd928fdf7dceda9a3852
'2012-03-13T08:08:48-04:00'
describe
'978781' 'info:fdaE20090811_AAABGAfileF20090811_AABWDG' 'sip-files00022.jp2'
c307d2fd0a093b47b7aee786f096fb62
2459a4c1592a49bee9719a77b58b0adc56d615c9
describe
'94169' 'info:fdaE20090811_AAABGAfileF20090811_AABWDH' 'sip-files00022.jpg'
7388d2a013309b6c547a3578ef9b57c9
5ec24a967ef57f72aaf4df4f367c3c8e15d70536
'2012-03-13T08:10:52-04:00'
describe
'46110' 'info:fdaE20090811_AAABGAfileF20090811_AABWDI' 'sip-files00022.pro'
04fc59be1351e8a6a67647fa58f1002a
7ca28b81945d8d27261b33db25bb57fcd7b85c63
'2012-03-13T08:08:47-04:00'
describe
'32153' 'info:fdaE20090811_AAABGAfileF20090811_AABWDJ' 'sip-files00022.QC.jpg'
fd7500ab9170d10a2afd9af9e58ccdef
721c8ca592c4f2e895eba057eff89376287ecb96
'2012-03-13T08:11:48-04:00'
describe
'7851972' 'info:fdaE20090811_AAABGAfileF20090811_AABWDK' 'sip-files00022.tif'
a924d035c6d68875c340e3615397308e
de1c276d8830c2d31379fbd8b1740bd0e48b9250
'2012-03-13T08:10:29-04:00'
describe
'1914' 'info:fdaE20090811_AAABGAfileF20090811_AABWDL' 'sip-files00022.txt'
25d015281ccff98202f6ecac7bd4325d
b9fdead1871a8a1e1dccd53283fd0f2c638c49c7
'2012-03-13T08:10:09-04:00'
describe
'8408' 'info:fdaE20090811_AAABGAfileF20090811_AABWDM' 'sip-files00022thm.jpg'
7986ae53922fa254d518957fd2faed4e
782c085f967ca6bb4049b0bdb1f9f0cfc65419bb
describe
'985670' 'info:fdaE20090811_AAABGAfileF20090811_AABWDN' 'sip-files00023.jp2'
aed7bf14df7bcb6e56e057fda6324fab
b351a81e458eb8b7cd4e2643b2b71e3c750a043a
'2012-03-13T08:09:46-04:00'
describe
'76974' 'info:fdaE20090811_AAABGAfileF20090811_AABWDO' 'sip-files00023.jpg'
d3af5d7d530f19fab8c3ca1d67ab86b8
880c5a132b6327cfe229e9a3ad64a99c94e70cf6
'2012-03-13T08:10:23-04:00'
describe
'38694' 'info:fdaE20090811_AAABGAfileF20090811_AABWDP' 'sip-files00023.pro'
009080ff4d30412612101aadd04a2cb3
9f78295f4c3383d0df6b48f79a26a30cbde7174f
'2012-03-13T08:10:07-04:00'
describe
'25080' 'info:fdaE20090811_AAABGAfileF20090811_AABWDQ' 'sip-files00023.QC.jpg'
62380e42653ea1b92ae0c069d254f6e0
b0e457cb6b9b1f6681325918859cc1dbbb9f850b
describe
'7903820' 'info:fdaE20090811_AAABGAfileF20090811_AABWDR' 'sip-files00023.tif'
373ba1abbb67b69ea7913802d959998b
f7172b491d4ec3f445309c23904502fb731f3d61
'2012-03-13T08:09:45-04:00'
describe
'1629' 'info:fdaE20090811_AAABGAfileF20090811_AABWDS' 'sip-files00023.txt'
df44956abce1c3de023550afa5823643
28dcced5fcf20f99d5e063f3324438ad7874e6b7
describe
'6908' 'info:fdaE20090811_AAABGAfileF20090811_AABWDT' 'sip-files00023thm.jpg'
3a05c5493f18d762b6d7a7c73a793080
557d612c7f66bcb50fd5abc2c5a2042c2ee8f107
'2012-03-13T08:09:47-04:00'
describe
'110983' 'info:fdaE20090811_AAABGAfileF20090811_AABWDU' 'sip-files00024.jp2'
f1b3d67a68dfc8c794e00b0884283b0d
6ee5cafa44b93540877dbb3074abe8402cc4e5d0
describe
'76578' 'info:fdaE20090811_AAABGAfileF20090811_AABWDV' 'sip-files00024.jpg'
a777b69966bf2ccc09aa798459ab46ea
98bad3cef5786087fcec8edd3991eeb6af5c0879
'2012-03-13T08:09:10-04:00'
describe
'39271' 'info:fdaE20090811_AAABGAfileF20090811_AABWDW' 'sip-files00024.pro'
97760564d56dc1969e56c05dbda6c2ea
d3f43dcba3cb537dbad8edfdd813eed8cdb9639f
describe
'26601' 'info:fdaE20090811_AAABGAfileF20090811_AABWDX' 'sip-files00024.QC.jpg'
f32fa51a5769db38fdade8c9dde365fb
b4da5a0127f379bbaa6745cc5ac8e5719fb55e4b
describe
'976386' 'info:fdaE20090811_AAABGAfileF20090811_AABWDY' 'sip-files00024.tif'
fc51d1f5a31f8f906c4c3393a416cd91
24ecfb1af89b5dfa38a5cba3daf37602e64992ec
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1684' 'info:fdaE20090811_AAABGAfileF20090811_AABWDZ' 'sip-files00024.txt'
844899d38c707c9f9cf8b674f6893ec9
9e35d9f6ccc20ff4d23fdad8e6fa3aaf3b419176
'2012-03-13T08:11:19-04:00'
describe
'7368' 'info:fdaE20090811_AAABGAfileF20090811_AABWEA' 'sip-files00024thm.jpg'
b8f4dd1b2529d75f028d3f3ef6ab6218
5954100f32899885008efb5f414fdda9549a4c4b
describe
'989004' 'info:fdaE20090811_AAABGAfileF20090811_AABWEB' 'sip-files00025.jp2'
a2efaa3cb3af835b8369371bd5a916a5
e22a5a865fbe33cb5691aacc2121e58a2dab8783
'2012-03-13T08:10:12-04:00'
describe
'83777' 'info:fdaE20090811_AAABGAfileF20090811_AABWEC' 'sip-files00025.jpg'
10f1f009a2abcaa524b7e8a1781bc42a
5e16032e242f5eaa7eb2d133dcfb2c43c0525292
describe
'43503' 'info:fdaE20090811_AAABGAfileF20090811_AABWED' 'sip-files00025.pro'
cafc72768db9ac6bc4da28da214e2159
a8f29c007ed1d0bbb8f1d6b4e96ef3582f8f3145
describe
'28545' 'info:fdaE20090811_AAABGAfileF20090811_AABWEE' 'sip-files00025.QC.jpg'
b2c96903c530593dc99678fa0e001d8c
6a7ed46fec3e06314251d47a2bb03024a3751b23
'2012-03-13T08:10:28-04:00'
describe
'7931920' 'info:fdaE20090811_AAABGAfileF20090811_AABWEF' 'sip-files00025.tif'
8013ad279f9f8324dbad53262a53d103
1d2b944f75806e4a09adc79da8cccbf3763e877e
'2012-03-13T08:09:53-04:00'
describe
'1765' 'info:fdaE20090811_AAABGAfileF20090811_AABWEG' 'sip-files00025.txt'
b31a349bed2b894f190a7a88d189610c
01992637a9a21298c3cb2264bf4ca96f40a300e7
describe
'7445' 'info:fdaE20090811_AAABGAfileF20090811_AABWEH' 'sip-files00025thm.jpg'
f0b0419c1604486a2984dd317296929e
0119aa41329424d1874d9d9536044ce3f7112b29
'2012-03-13T08:08:41-04:00'
describe
'986387' 'info:fdaE20090811_AAABGAfileF20090811_AABWEI' 'sip-files00026.jp2'
5159a5df46843646401a37f274497574
ef827baa9ed799fe3fd13fd414687c1a23a4e520
'2012-03-13T08:09:42-04:00'
describe
'79709' 'info:fdaE20090811_AAABGAfileF20090811_AABWEJ' 'sip-files00026.jpg'
4176276db203dadae0ed7875f81d9251
88d7b63b916f3856f45a487fca6ff859bb0c8a14
describe
'37918' 'info:fdaE20090811_AAABGAfileF20090811_AABWEK' 'sip-files00026.pro'
5b4135b9ce8f5b8fb3a58ca1d7d508f5
c78d853b8b79da7392fae3814d217cc3d0803d60
describe
'27178' 'info:fdaE20090811_AAABGAfileF20090811_AABWEL' 'sip-files00026.QC.jpg'
80f94cf4e6414b566f6ed9a353bcdb55
46bc463deb7081d1897b248f234eb08bf1cc1824
describe
'7909848' 'info:fdaE20090811_AAABGAfileF20090811_AABWEM' 'sip-files00026.tif'
e32484aa45eaca73ab9a2f11e57a4222
11190aa75342ec523b73a7c02ed30a33ab4cd321
'2012-03-13T08:09:51-04:00'
describe
'1569' 'info:fdaE20090811_AAABGAfileF20090811_AABWEN' 'sip-files00026.txt'
5bbb2a219b484ce9a40bae4ea0387387
32e8b17d724c781c39b421d4cf9a5a8864ddc641
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWEO' 'sip-files00026thm.jpg'
53132c6aed21e9647ce60514bc44e8ea
8821860767b1887159a16a03b3911f14691830e6
describe
'100932' 'info:fdaE20090811_AAABGAfileF20090811_AABWEP' 'sip-files00027.jp2'
c4f1879d0307ac519f0b4dd11de692b1
b5fd9507755e0f75f8aa7770c749abf324ab5127
describe
'73249' 'info:fdaE20090811_AAABGAfileF20090811_AABWEQ' 'sip-files00027.jpg'
45304f972088712c75dff69ad413396c
a39fca4848d7544c5ada95a94c0259b11e7d0b04
describe
'34869' 'info:fdaE20090811_AAABGAfileF20090811_AABWER' 'sip-files00027.pro'
98d0a47a22ca05e316bdd79dec826359
c845f5a2e613569b1f0d1f0db57f72bd8470017a
describe
'25559' 'info:fdaE20090811_AAABGAfileF20090811_AABWES' 'sip-files00027.QC.jpg'
113bbc58bd0eb8898bbff80480e4a3b2
b4becf56f7d5b5f80d154b79c7acee59b6d19be0
describe
'967986' 'info:fdaE20090811_AAABGAfileF20090811_AABWET' 'sip-files00027.tif'
4e16a3cbb8821a08569b3d8ac4664586
79e52b0e9d398760d92fe3604c867ee5b7d8a138
'2012-03-13T08:10:58-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1575' 'info:fdaE20090811_AAABGAfileF20090811_AABWEU' 'sip-files00027.txt'
6d2d938cd121d54073f342cf86a4f8da
15da5b6458c04f3c0bcb62596ba5c1c7ffcddcc9
describe
'7304' 'info:fdaE20090811_AAABGAfileF20090811_AABWEV' 'sip-files00027thm.jpg'
c5ba4853d188d4e008920cc18b7a8abb
58a2515ee83d679773599ed410f72bfbd68bab8c
describe
'97455' 'info:fdaE20090811_AAABGAfileF20090811_AABWEW' 'sip-files00028.jp2'
c64fa47dbb28d1b11e53f4aa88e9b113
05da5ab92d22fda0dfa7f2913eafa239a39e10a1
'2012-03-13T08:10:45-04:00'
describe
'69371' 'info:fdaE20090811_AAABGAfileF20090811_AABWEX' 'sip-files00028.jpg'
82e7543b3673e8397a466f1e91b65021
632726a5e8dde3dc1968b619e986afcfff236aea
describe
'32787' 'info:fdaE20090811_AAABGAfileF20090811_AABWEY' 'sip-files00028.pro'
b2a986e8abc872c4577e916cae08fdf9
86134b6ba22b6c7c0dc0fcb90650c047533f6477
'2012-03-13T08:09:57-04:00'
describe
'24691' 'info:fdaE20090811_AAABGAfileF20090811_AABWEZ' 'sip-files00028.QC.jpg'
417bedc48775aede775289b2d82c6f64
1598063b06e0c234684bb877f52a0f86a7635866
describe
'969786' 'info:fdaE20090811_AAABGAfileF20090811_AABWFA' 'sip-files00028.tif'
1902d2e456ea821e3dad5f79f3c18f33
f44dd4badb426f8dcda59123d52dd5aedfe4a201
'2012-03-13T08:09:56-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1357' 'info:fdaE20090811_AAABGAfileF20090811_AABWFB' 'sip-files00028.txt'
0f1c4e23086349b478dcc8f5a3a1bfc5
3e646f613e98ef1ba6a178a0df2933e9aef61fe2
describe
'7135' 'info:fdaE20090811_AAABGAfileF20090811_AABWFC' 'sip-files00028thm.jpg'
4701ef36d5699188633f3d70b8b1c06d
c1c74122f399f54e2636e62ce1be02acfba9198d
describe
'113999' 'info:fdaE20090811_AAABGAfileF20090811_AABWFD' 'sip-files00029.jp2'
67973b69c0358d78fa88e556a32f53d7
1bf8c9c0ee3123cc612b212629a4e679c353d32a
'2012-03-13T08:09:16-04:00'
describe
'79109' 'info:fdaE20090811_AAABGAfileF20090811_AABWFE' 'sip-files00029.jpg'
6a091907d864123db074b5fdf206f575
6300ffef303542a4d4f4e216e6ce9d6fc3b66024
describe
'39242' 'info:fdaE20090811_AAABGAfileF20090811_AABWFF' 'sip-files00029.pro'
1d732d5c703a32a7745a4b553a564c87
fa7a27c7b3ee6a4b1ab5df790d00d7ada8d86350
describe
'28236' 'info:fdaE20090811_AAABGAfileF20090811_AABWFG' 'sip-files00029.QC.jpg'
3c19b1de264b16a4b74a9d93864120d5
3fa1e56279ec5a9feaffe9a842353586024a74b7
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWFH' 'sip-files00029.tif'
ba69ec1aad240e2d5d3600b07c8487a2
a108d9bc21d5cc4e33d9a29e8f4136e534d930fd
'2012-03-13T08:10:04-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1676' 'info:fdaE20090811_AAABGAfileF20090811_AABWFI' 'sip-files00029.txt'
6320b60deb026d47ef56816a16d51405
f6b6175c202a43722a0ac610ac2d674d8912a266
'2012-03-13T08:10:15-04:00'
describe
Invalid character
'7924' 'info:fdaE20090811_AAABGAfileF20090811_AABWFJ' 'sip-files00029thm.jpg'
4ce0fd42dfda0157a31f15db8e01d527
da3641bf9a032026498b327869d704e4b0346e4a
describe
'90030' 'info:fdaE20090811_AAABGAfileF20090811_AABWFK' 'sip-files00030.jp2'
9a5a7f1dab66950befa7503ba653cce3
08a52d119a5e70f5dd1892194690f8713f630214
'2012-03-13T08:11:08-04:00'
describe
'63688' 'info:fdaE20090811_AAABGAfileF20090811_AABWFL' 'sip-files00030.jpg'
5f8dd79e947c0a3d81bcc1169b0885ea
8713d2e5fd3aba3d0be4a2d4100bd1e0c58a6028
'2012-03-13T08:10:03-04:00'
describe
'30649' 'info:fdaE20090811_AAABGAfileF20090811_AABWFM' 'sip-files00030.pro'
47fc8f7490815182267e1ccd2c7fc413
5113351cb7b7321eb0cb95df67da6bec1ab91304
'2012-03-13T08:09:21-04:00'
describe
'23137' 'info:fdaE20090811_AAABGAfileF20090811_AABWFN' 'sip-files00030.QC.jpg'
5a773d463593065a709d556b30874fe9
e4915fe9593661d63205e1cb21964ba44d167929
'2012-03-13T08:10:17-04:00'
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWFO' 'sip-files00030.tif'
61c9e40037321b46c756eb27f3973ce8
80264af0eeafb3e61846762f36a4e9cbb35a8c8d
'2012-03-13T08:09:48-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1326' 'info:fdaE20090811_AAABGAfileF20090811_AABWFP' 'sip-files00030.txt'
5f404ff9397ea1c94721791489e762ce
8077ad071332706c318d3a9b0ca5d10f29b38868
'2012-03-13T08:08:42-04:00'
describe
'6591' 'info:fdaE20090811_AAABGAfileF20090811_AABWFQ' 'sip-files00030thm.jpg'
25a64c7ed641e3a0662deae4e75f15ca
fb1d50954bf174cac3095bbfc6f107f4865e6f22
describe
'57886' 'info:fdaE20090811_AAABGAfileF20090811_AABWFR' 'sip-files00031.jp2'
4c6b72ab7c2d62675f871405de6cc417
9d27b1a319fcce987319046801582d4ee951ac19
describe
'25647' 'info:fdaE20090811_AAABGAfileF20090811_AABWFS' 'sip-files00031.jpg'
1612c2c9a0c3cbdcfaba044f5c444b7a
f8c9ad8519f0dcc749019b6173506f1fa64b9b24
describe
'19548' 'info:fdaE20090811_AAABGAfileF20090811_AABWFT' 'sip-files00031.pro'
a3141ff290bb10df193932fcb39785e4
a1b57ffcc4b83b044d1e709c13375a9e7646aaa4
describe
'9593' 'info:fdaE20090811_AAABGAfileF20090811_AABWFU' 'sip-files00031.QC.jpg'
d59c8569a31e9dac92ca11c47d906651
fda4e9cf2d69e731d877ac2b78caca62918057f6
describe
'999088' 'info:fdaE20090811_AAABGAfileF20090811_AABWFV' 'sip-files00031.tif'
65bdf5312269d1ac0c94af59f02a0919
c719a52a4550709725b3dd5ddfbe6094c35ba5df
'2012-03-13T08:11:00-04:00'
describe
'865' 'info:fdaE20090811_AAABGAfileF20090811_AABWFW' 'sip-files00031.txt'
327ec4b27e0c277cca1eb5130a810a26
1c1a4518d5e816e977644514374671b8ae693510
describe
'3276' 'info:fdaE20090811_AAABGAfileF20090811_AABWFX' 'sip-files00031thm.jpg'
08c2e41c74b0fbfc655502669e51f2d9
9eb3d1ad13a21fbe108198e231d420d6fa7c2819
'2012-03-13T08:11:15-04:00'
describe
'62580' 'info:fdaE20090811_AAABGAfileF20090811_AABWFY' 'sip-files00032.jp2'
7d1574b3ba439ce39ec797165899b418
70ed30f7ee0a18fcdca466284bdd3cf8823e93b9
describe
'26737' 'info:fdaE20090811_AAABGAfileF20090811_AABWFZ' 'sip-files00032.jpg'
b6eb153818990d741a71bf119e4dee80
fe90e95a3282ed192bcd3e27724e01cb95b741ec
'2012-03-13T08:09:34-04:00'
describe
'26683' 'info:fdaE20090811_AAABGAfileF20090811_AABWGA' 'sip-files00032.pro'
b390f25d7039d5507f22aafdaef0cf78
5ae95364e0ff832fe7d9a665023dbc04d6dd9a7a
describe
'10295' 'info:fdaE20090811_AAABGAfileF20090811_AABWGB' 'sip-files00032.QC.jpg'
7c75645578cd44bf140a7241c166e55e
c19463b69f8f9e1c5243db8add1b3ff0391871f1
'2012-03-13T08:10:01-04:00'
describe
'1011672' 'info:fdaE20090811_AAABGAfileF20090811_AABWGC' 'sip-files00032.tif'
6e87ce1bf7e671de65e1140c3ce894a1
9ef6aa848cc65707032ee02a3f407b3f4447a881
'2012-03-13T08:11:06-04:00'
describe
'1484' 'info:fdaE20090811_AAABGAfileF20090811_AABWGD' 'sip-files00032.txt'
cb9e75c913ad3254e0fd2a78ae7f9ab6
bc6125540c36a958dfbb2488bc515a735b0857ee
'2012-03-13T08:11:50-04:00'
describe
Invalid character
'3424' 'info:fdaE20090811_AAABGAfileF20090811_AABWGE' 'sip-files00032thm.jpg'
990b2bb9abb3761125e99a31a95b5bdd
11fd19d7767061fe3b9b2a59572e03a9731296e7
describe
'50657' 'info:fdaE20090811_AAABGAfileF20090811_AABWGF' 'sip-files00033.jp2'
20c154c878af7b37a1724875e15cbf75
3c3edf8d3c79346ae2056a2714ebacfb83ba8e66
'2012-03-13T08:08:59-04:00'
describe
'23492' 'info:fdaE20090811_AAABGAfileF20090811_AABWGG' 'sip-files00033.jpg'
2298b499f0ce4b8a8c4abdad26d1d575
140ad331ead5a66bce71c20a3437c89bebe397a2
'2012-03-13T08:09:52-04:00'
describe
'15713' 'info:fdaE20090811_AAABGAfileF20090811_AABWGH' 'sip-files00033.pro'
39cc5dab139f2d16bef0531fc235410e
d2d36f40e4b8d16aae8b322bb4ed38cd8db99b39
describe
'8135' 'info:fdaE20090811_AAABGAfileF20090811_AABWGI' 'sip-files00033.QC.jpg'
edc31a86ca247010aa3f0773f40b1196
8695376567da0feb4b29fe5479c754236bcb8590
describe
'967854' 'info:fdaE20090811_AAABGAfileF20090811_AABWGJ' 'sip-files00033.tif'
f5cec0b845ac9a3774a0921591b2b4b4
55f0846771e9b6ec8978fc04c3826f92facff1d1
'2012-03-13T08:10:47-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'779' 'info:fdaE20090811_AAABGAfileF20090811_AABWGK' 'sip-files00033.txt'
c16641e9d485b321b43624f691cbc793
3c32311c1832ca364d4e37f94e15056611aa3cca
'2012-03-13T08:10:38-04:00'
describe
'2723' 'info:fdaE20090811_AAABGAfileF20090811_AABWGL' 'sip-files00033thm.jpg'
aebbd30aee607e61930ad3872b57c0a3
b9ec263904bd0900d84a6337dd7ee71119860ed0
describe
'73240' 'info:fdaE20090811_AAABGAfileF20090811_AABWGM' 'sip-files00034.jp2'
c3599408fb7c4502941f0ebb6dc4bb9b
53addc8c1f6eba827107660944e6cb554a7ea74a
describe
'32582' 'info:fdaE20090811_AAABGAfileF20090811_AABWGN' 'sip-files00034.jpg'
05f638fe689582cacb0d8c6f583a58c2
ee1eb32f9b2254fe42350924487b4f8970e3a751
'2012-03-13T08:10:50-04:00'
describe
'27177' 'info:fdaE20090811_AAABGAfileF20090811_AABWGO' 'sip-files00034.pro'
b71164737d7d17f275fdfcf28d2f95bc
0fa5d4ab2ae0c8d838e980bd6bccf33d9e27a4a6
describe
'11551' 'info:fdaE20090811_AAABGAfileF20090811_AABWGP' 'sip-files00034.QC.jpg'
0dd39a6d9ddfb1c5d2e0ee428cc8fd4e
871217ea6083274355d398c6c2cb6d7ab8a0527e
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWGQ' 'sip-files00034.tif'
021403fe10168774959b2b3a2d63bd8c
9950fdf3a3431d2e394727242cd2e95572ad4933
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1315' 'info:fdaE20090811_AAABGAfileF20090811_AABWGR' 'sip-files00034.txt'
f9fa7757d2af203daa8cc365dcd37564
aefc71532583f4686af9da085d7c570dbb50fd6d
'2012-03-13T08:09:05-04:00'
describe
Invalid character
'3765' 'info:fdaE20090811_AAABGAfileF20090811_AABWGS' 'sip-files00034thm.jpg'
5509f1979f2f595a603df651e8234a72
0e841fab86c385ddf51c7269f82b4f888eb2a457
describe
'42434' 'info:fdaE20090811_AAABGAfileF20090811_AABWGT' 'sip-files00035.jp2'
834df50e7372ae3c1806ee612baaca8d
5726696831445b2876c1c5f06b19d77517b4ebcf
'2012-03-13T08:09:50-04:00'
describe
'20476' 'info:fdaE20090811_AAABGAfileF20090811_AABWGU' 'sip-files00035.jpg'
38615ad014833d5be782acd65957c504
b894b27cb29dbb39b3de75cf8ab562dc11d3a021
describe
'13069' 'info:fdaE20090811_AAABGAfileF20090811_AABWGV' 'sip-files00035.pro'
d9f41346481967543251e3d5078009a1
bc842500dd8347f0709922a65d17214a2bfc975c
describe
'7166' 'info:fdaE20090811_AAABGAfileF20090811_AABWGW' 'sip-files00035.QC.jpg'
69f5fc25c5efb18aa6ce5f67b74167f1
9bb71ea2633568245b00696986444de5a5474831
'2012-03-13T08:08:44-04:00'
describe
'979460' 'info:fdaE20090811_AAABGAfileF20090811_AABWGX' 'sip-files00035.tif'
bef98dfade2d9fa53e6b9208f23887b0
584c7294589ae839a765df8e3d0e88b4bc29a607
describe
'770' 'info:fdaE20090811_AAABGAfileF20090811_AABWGY' 'sip-files00035.txt'
f882b88a489c6926350d0e853063ec90
a3a65fcaec3f1a9f7b1dd7b470b8d76b21a8cc2a
describe
'2487' 'info:fdaE20090811_AAABGAfileF20090811_AABWGZ' 'sip-files00035thm.jpg'
b4df427dd020978a9fff5d8d569d9e49
4af44a2238da82d3ae1bc802383784f190f233e0
'2012-03-13T08:08:38-04:00'
describe
'63909' 'info:fdaE20090811_AAABGAfileF20090811_AABWHA' 'sip-files00036.jp2'
5e908f3db1e1708ecb4a978961829175
e4896129ca8b36a11a28852af2088d02c1e973e3
'2012-03-13T08:09:13-04:00'
describe
'28133' 'info:fdaE20090811_AAABGAfileF20090811_AABWHB' 'sip-files00036.jpg'
7210f779f8fc7ddcb6311ce6bd356ad3
7035bb739cf9da3c3e6c16cb2a1a439d512096ec
describe
'22730' 'info:fdaE20090811_AAABGAfileF20090811_AABWHC' 'sip-files00036.pro'
24bef38a82cec7147cf51235ff038bbd
da18100c89a1953ccda20d3111357a2cee24d9f2
describe
'9768' 'info:fdaE20090811_AAABGAfileF20090811_AABWHD' 'sip-files00036.QC.jpg'
dc4b8d2bbf6666b13d1161302eec77a7
10ed0b73e56df82225e09b7236c28f99de9e86e1
describe
'975794' 'info:fdaE20090811_AAABGAfileF20090811_AABWHE' 'sip-files00036.tif'
a4d1a14f35b1eb158dc55655780e1c25
d6fe8e914e698ca10461745d019d47fbce6ad417
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1028' 'info:fdaE20090811_AAABGAfileF20090811_AABWHF' 'sip-files00036.txt'
b8a5031ef01aa9ca9a825b8c5b954bcc
6a80fdaaabf7620d8c7ef0b2caa857ad1d57ed80
describe
Invalid character
'3270' 'info:fdaE20090811_AAABGAfileF20090811_AABWHG' 'sip-files00036thm.jpg'
d586004096caf09f3eb6f7a0afe2735a
3d45d485c03678a5cf12be6746bd6368564fd37a
describe
'55007' 'info:fdaE20090811_AAABGAfileF20090811_AABWHH' 'sip-files00037.jp2'
ffcafebd9dc520e71b314ff4bcb9e5e9
f769b00d907be4adba41dd70ec84a16768ad14d1
describe
'26220' 'info:fdaE20090811_AAABGAfileF20090811_AABWHI' 'sip-files00037.jpg'
364abb2618c11bdf8dc7e6a5486f4a70
200c3bad9069527db097508154111562b10b791f
'2012-03-13T08:09:29-04:00'
describe
'18914' 'info:fdaE20090811_AAABGAfileF20090811_AABWHJ' 'sip-files00037.pro'
643c3f95eaf0c18219ea4e59e4807cd2
1f525eddd6f257edf178fd2d817512202fa598f3
describe
'8776' 'info:fdaE20090811_AAABGAfileF20090811_AABWHK' 'sip-files00037.QC.jpg'
3aac87723e2495058c49306d473c4d57
4633b1c0b519da606fa94b44c5f914612ffb8e74
describe
'967046' 'info:fdaE20090811_AAABGAfileF20090811_AABWHL' 'sip-files00037.tif'
61f5886d633719a20c354dfcdfe5ef26
1e0cc2d07250ba792ec66e7b9d91b91703c8c63c
'2012-03-13T08:11:43-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1023' 'info:fdaE20090811_AAABGAfileF20090811_AABWHM' 'sip-files00037.txt'
d1f09eacc0bd4bf8625f93f2c1052e66
7a75094a185fc2afaa6190f17ad161cbcbd78d7c
describe
'3094' 'info:fdaE20090811_AAABGAfileF20090811_AABWHN' 'sip-files00037thm.jpg'
2733ea6efcd9634b01e49d863ebbcc9a
2760d96ec626d8b6418108eecfa36faedaf7e140
'2012-03-13T08:11:26-04:00'
describe
'65188' 'info:fdaE20090811_AAABGAfileF20090811_AABWHO' 'sip-files00038.jp2'
13547dad725499e63f91da849a44e19c
b838abccdc566743095b331667344b3713ea361f
'2012-03-13T08:08:39-04:00'
describe
'27213' 'info:fdaE20090811_AAABGAfileF20090811_AABWHP' 'sip-files00038.jpg'
ea2f9ddf9b6d70913e8d36c9e561b525
7ef41990cfccde61214396f70566412684c8719c
describe
'18317' 'info:fdaE20090811_AAABGAfileF20090811_AABWHQ' 'sip-files00038.pro'
3b2a2857035b763c887318cd53a26166
592df9e1bc0f9d5ec26911d68fa68d4ffb3ea792
describe
'8887' 'info:fdaE20090811_AAABGAfileF20090811_AABWHR' 'sip-files00038.QC.jpg'
6174cfaa3f53779a97c144aeadbf5dfc
ca778469093a1b12e6ab874542c7b9d45b9fa80f
describe
'966238' 'info:fdaE20090811_AAABGAfileF20090811_AABWHS' 'sip-files00038.tif'
67312f3115184e969bf38bf0a6f146b8
4fc10cd2db0f2cf2d4475d2235552c3c23ecc57a
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'836' 'info:fdaE20090811_AAABGAfileF20090811_AABWHT' 'sip-files00038.txt'
430e233daa8c71f55cfe3463ce9cb30f
57ea4c594ddf854bd51e89c69ae36fe6665e141c
describe
Invalid character
'3098' 'info:fdaE20090811_AAABGAfileF20090811_AABWHU' 'sip-files00038thm.jpg'
42b5f1d4a49309720f06ca2495278ad4
4e1bf2a54b9a74218477af682ee8779d63dd856b
describe
'60184' 'info:fdaE20090811_AAABGAfileF20090811_AABWHV' 'sip-files00039.jp2'
96ce4b28c3931f1e93575266abfcda44
aa2a425a1e3d6b89b036c4ae5cbfbf28d58766f4
describe
'28734' 'info:fdaE20090811_AAABGAfileF20090811_AABWHW' 'sip-files00039.jpg'
c2f6875a1df947a2e710da357ee53717
4ba41109fba1f421a04102cba98f881556ac30da
describe
'18602' 'info:fdaE20090811_AAABGAfileF20090811_AABWHX' 'sip-files00039.pro'
68549121cc9555ba69d2acdd84527a09
b4d4b512cb1b4ec1d20c19068409f07f407fef1e
describe
'9578' 'info:fdaE20090811_AAABGAfileF20090811_AABWHY' 'sip-files00039.QC.jpg'
ac2a1069f29c8556f2ac358d3c244888
8dd39bb2944bb5094422c89cd59f9518fbd2d99d
'2012-03-13T08:09:59-04:00'
describe
'980464' 'info:fdaE20090811_AAABGAfileF20090811_AABWHZ' 'sip-files00039.tif'
305e80745e0c6223712aa72bf8c60a97
0f4f8bd7a897cf55618bccbae5534eb04eb2ef00
describe
'1146' 'info:fdaE20090811_AAABGAfileF20090811_AABWIA' 'sip-files00039.txt'
3afb0113a7696de4f1a902c60015b3cb
82c6fd280f053b113dec4145cf18051e6043f6aa
describe
Invalid character
'3338' 'info:fdaE20090811_AAABGAfileF20090811_AABWIB' 'sip-files00039thm.jpg'
3b9a884761e9849868539f8b26afc583
7fba9f682ee147b1eda65bb4c4174f542d5e5a36
describe
'967064' 'info:fdaE20090811_AAABGAfileF20090811_AABWIC' 'sip-files00040.jp2'
d34e6aa6704eba795dc2f2337ddb3470
d926535385bd4d172fdbb0a3289d14df45153c17
describe
'87317' 'info:fdaE20090811_AAABGAfileF20090811_AABWID' 'sip-files00040.jpg'
34e6332ddd706b1b9741ad9ac8abf746
0d9e70638acfd6edfa1c07e8ad019d1382295e05
'2012-03-13T08:10:43-04:00'
describe
'40156' 'info:fdaE20090811_AAABGAfileF20090811_AABWIE' 'sip-files00040.pro'
16bf4ce3db457ab55d2df5659288caba
038f372dc14e74f49c6c0f07c33d3b99d935b47f
describe
'29065' 'info:fdaE20090811_AAABGAfileF20090811_AABWIF' 'sip-files00040.QC.jpg'
941628ca749654c0be814da5ee59e640
daa372427e6ebdeb738a02cfd140ee9a2e78f356
describe
'7757296' 'info:fdaE20090811_AAABGAfileF20090811_AABWIG' 'sip-files00040.tif'
5db4ccde6b77a2dc774f4f5d03528288
cc2b903c2146b0e245672ff77660a7fa53acd52c
describe
'1709' 'info:fdaE20090811_AAABGAfileF20090811_AABWIH' 'sip-files00040.txt'
81f3e6d7be1f92ce9eef75660f4852ce
7191058675a610c6860ec7fd5099c26bf3e1be4c
describe
'7863' 'info:fdaE20090811_AAABGAfileF20090811_AABWII' 'sip-files00040thm.jpg'
818f3f7e51c16b8f7ecbfaf7fed0657c
1284d1acf9fa4ec6940718650e4e6a8adb7b9ae1
'2012-03-13T08:10:08-04:00'
describe
'131821' 'info:fdaE20090811_AAABGAfileF20090811_AABWIJ' 'sip-files00041.jp2'
b1411e895c05cfeba197a810a179a85b
a6b2a75c0ba7836884cac3e1a9a450ff8ec84071
describe
'87301' 'info:fdaE20090811_AAABGAfileF20090811_AABWIK' 'sip-files00041.jpg'
d87fd083ad9214b99f0301016fe94011
81056e7cc41380823c6877a5b7af27708d475aa2
'2012-03-13T08:09:25-04:00'
describe
'44657' 'info:fdaE20090811_AAABGAfileF20090811_AABWIL' 'sip-files00041.pro'
d6d8c8cf497486cab7b1b7eadf29d2a2
4239bef94aa259f181262c1a7a8124fe0054dedf
describe
'30668' 'info:fdaE20090811_AAABGAfileF20090811_AABWIM' 'sip-files00041.QC.jpg'
c21b73f1a3af371cb0e8a493336a3149
b35f33b39dbbf146feedaefc40e551248f1d99f8
describe
'1014052' 'info:fdaE20090811_AAABGAfileF20090811_AABWIN' 'sip-files00041.tif'
5cd6c1009c900e960b316ae084d2dd7a
2dcd1ff4547795c1c2171b76a5ee405f5f4c6f86
describe
'1795' 'info:fdaE20090811_AAABGAfileF20090811_AABWIO' 'sip-files00041.txt'
ff637dbe7852997b18c046c953814214
6e6406837facd600ba9351ee34fe87a241fb23d4
describe
Invalid character
'982936' 'info:fdaE20090811_AAABGAfileF20090811_AABWIP' 'sip-files00041a0001.jp2'
34328387f2b5ffb94499d30bbf433fe8
0057b17b74a28d02cbd665855ca5d7f255beba9c
describe
'83639' 'info:fdaE20090811_AAABGAfileF20090811_AABWIQ' 'sip-files00041a0001.jpg'
5052ccb3427e93c41e5d3764cd9076b7
94313e1c2539f33e4a8a2760aa40db1cb1dfff02
describe
'42184' 'info:fdaE20090811_AAABGAfileF20090811_AABWIR' 'sip-files00041a0001.pro'
4a64ca0275978e74488e4d45f6a7a9fb
1076f262031b296b7bf755940c49e7ad52984e32
describe
'28955' 'info:fdaE20090811_AAABGAfileF20090811_AABWIS' 'sip-files00041a0001.QC.jpg'
ed7862f9362df40c5789d35e41c30d23
ee978d7a3ecfeb1cabab0769321d83f206ef06ec
describe
'7883276' 'info:fdaE20090811_AAABGAfileF20090811_AABWIT' 'sip-files00041a0001.tif'
0a5bf94ded47e3838241cc4197c2a17a
dade02fb6d3de4f5e34ad049b8cddab71aeb26ba
describe
'1813' 'info:fdaE20090811_AAABGAfileF20090811_AABWIU' 'sip-files00041a0001.txt'
dfb82f5a8567dd8c89ec801a35adafd7
ba18b59761ddcd616a4441e188926386cfbca895
'2012-03-13T08:08:54-04:00'
describe
'8024' 'info:fdaE20090811_AAABGAfileF20090811_AABWIV' 'sip-files00041a0001thm.jpg'
3d7024cda15f0cf5235dd9a580287efa
bdb8a6d7dae3318542e859f7e587809b69952526
describe
'990730' 'info:fdaE20090811_AAABGAfileF20090811_AABWIW' 'sip-files00041a0002.jp2'
4905301c2657c4afb2142a43d3a3d965
b6b7ed8cc11f3919857bf5917302d5114fd2bbf5
describe
'88242' 'info:fdaE20090811_AAABGAfileF20090811_AABWIX' 'sip-files00041a0002.jpg'
88d524e910cf7d01b758d6e52f768838
9d78095751945fd7a52ddfe9ce399eda275cc496
describe
'44344' 'info:fdaE20090811_AAABGAfileF20090811_AABWIY' 'sip-files00041a0002.pro'
97615a410bce190d2beab34a93d42e0a
18a885890585c17aa02e41d450ef6e33559be6e3
describe
'29810' 'info:fdaE20090811_AAABGAfileF20090811_AABWIZ' 'sip-files00041a0002.QC.jpg'
490d8b646d4d568d97228fb6acc37b04
e33e96f566e883a6a3da5da6cd41957f5b7fab7a
describe
'7946452' 'info:fdaE20090811_AAABGAfileF20090811_AABWJA' 'sip-files00041a0002.tif'
687d39ff514169a94fef899780a6c237
ebfd6c519b4bd693506edadaf9c31036b4462a38
'2012-03-13T08:08:55-04:00'
describe
'1777' 'info:fdaE20090811_AAABGAfileF20090811_AABWJB' 'sip-files00041a0002.txt'
b0033b0377ab79c7992a55964ffe9320
53de74019daf246efdbc4b74b6f9bdd2e0e515b3
'2012-03-13T08:10:41-04:00'
describe
'7767' 'info:fdaE20090811_AAABGAfileF20090811_AABWJC' 'sip-files00041a0002thm.jpg'
d493c8fff9a7f9e0634173319a12db5b
2b246e6d11a053bb772ec7b3e8cf2d3462000152
describe
'8818' 'info:fdaE20090811_AAABGAfileF20090811_AABWJD' 'sip-files00041thm.jpg'
4bae7a586256a6acad361811f76142b4
ac212f0369f10ad2c7ecc22d37609490d7a2e3a1
'2012-03-13T08:09:43-04:00'
describe
'982423' 'info:fdaE20090811_AAABGAfileF20090811_AABWJE' 'sip-files00042.jp2'
acb43723ca3dc600ab575e253957af25
85dc07d288f5bd9df09f3e2d6e8ee8b105d8f5ef
describe
'76965' 'info:fdaE20090811_AAABGAfileF20090811_AABWJF' 'sip-files00042.jpg'
6f10d15f5f3c4db11da8a8bcc7486b34
0c5e70241556134c2a84a1092fd977581cd3bc6d
'2012-03-13T08:10:56-04:00'
describe
'32182' 'info:fdaE20090811_AAABGAfileF20090811_AABWJG' 'sip-files00042.pro'
1854d97a34615e1d000fce7b77e6e29e
15767f35d6a9df5e8236e90193fabd6f147e6e7b
describe
'24575' 'info:fdaE20090811_AAABGAfileF20090811_AABWJH' 'sip-files00042.QC.jpg'
5f765a79c9e87f5db3be5fc2fd37e931
a3d1d2fcd042791cc02aba291e22bd8fc8a0ada5
describe
'7878852' 'info:fdaE20090811_AAABGAfileF20090811_AABWJI' 'sip-files00042.tif'
f10e36aea6c9e5f90a46a9c7da0ba1ae
321b435623586809ce439555bc88f7c61d810679
'2012-03-13T08:10:35-04:00'
describe
'1423' 'info:fdaE20090811_AAABGAfileF20090811_AABWJJ' 'sip-files00042.txt'
263d68826cc2e1899851935c9fbe31f5
9f4cb568453ad3617346b97ec7392aca3bf7578f
'2012-03-13T08:11:03-04:00'
describe
Invalid character
'6855' 'info:fdaE20090811_AAABGAfileF20090811_AABWJK' 'sip-files00042thm.jpg'
1cb080c685f52f4d61cbf15ede609387
356e8873bbb881495624b94e757d11df3b1cbfb1
describe
'113396' 'info:fdaE20090811_AAABGAfileF20090811_AABWJL' 'sip-files00043.jp2'
8f747b9756f11859cde161aae864336b
e1fe26adba4d221a9a2271d6db01cbb8b73c143b
describe
'80592' 'info:fdaE20090811_AAABGAfileF20090811_AABWJM' 'sip-files00043.jpg'
c712a2b79e8cf4e7934bbb42a234fcf3
d4bff8bf468e9cbb2ad37928de9eb91c1a55ccec
describe
'32133' 'info:fdaE20090811_AAABGAfileF20090811_AABWJN' 'sip-files00043.pro'
e95758d3f3d0bfe85f3cfa8205546d82
58262421431825e5ac1fca11f1ba8f8f41c1b4f0
describe
'28077' 'info:fdaE20090811_AAABGAfileF20090811_AABWJO' 'sip-files00043.QC.jpg'
d58f62846597b74621d070e03caf896b
c84abcf9d16ee04dc7e8bd667c682b4efb2cddbc
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWJP' 'sip-files00043.tif'
6e0a59fe8e40e5320f1cb3c3624172b7
15f0ee502e62fb2d949d84baac0c78a6aae19ea8
'2012-03-13T08:08:50-04:00'
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1409' 'info:fdaE20090811_AAABGAfileF20090811_AABWJQ' 'sip-files00043.txt'
43c13dc03c8047dc761343c5837f1133
39ff3af9874618419c34e3a982f2bbf5fd2179d6
describe
Invalid character
'8164' 'info:fdaE20090811_AAABGAfileF20090811_AABWJR' 'sip-files00043thm.jpg'
31b4f6ec30c2f1c4abb5348fc25dcf47
49c26085b15498c9c9dbe1480c39b40394143fe0
'2012-03-13T08:11:32-04:00'
describe
'157321' 'info:fdaE20090811_AAABGAfileF20090811_AABWJS' 'sip-files00044.jp2'
837e27f7c67f9ca1ecaba156b46deab5
4604c9558d2854b939a47fb8fec303339a8b6e5d
describe
'104503' 'info:fdaE20090811_AAABGAfileF20090811_AABWJT' 'sip-files00044.jpg'
786e0856b22624a63485e4b3498a93c4
9d9441e35eda86400256b232881ffcdafdf07194
describe
'43757' 'info:fdaE20090811_AAABGAfileF20090811_AABWJU' 'sip-files00044.pro'
bfa640fda666fdffb013a70253eb1213
0fa65dbf62b14ed25aa7e0213757bb396f27d8fd
describe
'33435' 'info:fdaE20090811_AAABGAfileF20090811_AABWJV' 'sip-files00044.QC.jpg'
1c4e42842ba9717e5efeb5bd2dd2f60c
638dd0723e48975b718cdaee412b57fb1f96c3b3
describe
'964163' 'info:fdaE20090811_AAABGAfileF20090811_AABWJW' 'sip-files00044.tif'
458ca5755cd36a8e452ac54dc0be623f
8b385f7d5c9a7c4c81333386f4a8b52cd2a78c04
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1789' 'info:fdaE20090811_AAABGAfileF20090811_AABWJX' 'sip-files00044.txt'
dc909b4c428094db488140f0a1e2ceff
84bd2cd0cc6730e0d968c041df7c5cc1c2277f58
describe
'9244' 'info:fdaE20090811_AAABGAfileF20090811_AABWJY' 'sip-files00044thm.jpg'
9757e693df9dc9e594506d23c0235fce
9940df3903eae9a3e7c5bd05e0f511c86eeabdc7
describe
'971980' 'info:fdaE20090811_AAABGAfileF20090811_AABWJZ' 'sip-files00045.jp2'
fc741d86e243827f1386a74f0e788e5e
1cab4bc4ef2de104617a345a6653a55982bb5b6a
describe
'85172' 'info:fdaE20090811_AAABGAfileF20090811_AABWKA' 'sip-files00045.jpg'
0b81dcb8533fe037b5392f3189a164fa
ffb5812f404d94a0f611a0f300dec964a9bc662f
describe
'38294' 'info:fdaE20090811_AAABGAfileF20090811_AABWKB' 'sip-files00045.pro'
59141b2c3ff9d75c7ef56e0c9f2cf3a5
39b71461f00bab6ba82d6c94d0bb0a3c6715f9ed
describe
'27995' 'info:fdaE20090811_AAABGAfileF20090811_AABWKC' 'sip-files00045.QC.jpg'
1d28199f1316c43a4fb4d5130d242595
67bad8c78ac1da072b46ef1af5a712ed7e655a15
describe
'7795892' 'info:fdaE20090811_AAABGAfileF20090811_AABWKD' 'sip-files00045.tif'
a7dd9cfc4c01a3c6335bf59898fcadc0
0e0bc56be20e8fdf2e76fcc0743ca3382d0e8b63
'2012-03-13T08:11:33-04:00'
describe
'1660' 'info:fdaE20090811_AAABGAfileF20090811_AABWKE' 'sip-files00045.txt'
433fcfdfdf2354f746a98110e2e3881a
74095289f658e794d35e98a523c77d2bfa909526
describe
'7858' 'info:fdaE20090811_AAABGAfileF20090811_AABWKF' 'sip-files00045thm.jpg'
4a45baa782b3148727b5d226cbdb94db
1c2c9a978ec15d49adb47f734a581ba76625e250
describe
'18610' 'info:fdaE20090811_AAABGAfileF20090811_AABWKG' 'sip-files00046.jp2'
77a69f03051b20df6454d5667288ae62
9589e776fad36c27926f97f8dbb3f1d0fcd4b707
describe
'18081' 'info:fdaE20090811_AAABGAfileF20090811_AABWKH' 'sip-files00046.jpg'
87e0fd88ebc9ca291269c641d7b60496
688155a96b424956f5afb831cfecdb97cc6e27a4
describe
'4994' 'info:fdaE20090811_AAABGAfileF20090811_AABWKI' 'sip-files00046.pro'
b0eb7e16bcf858ca2f55e9933b5befdb
2f467f3ca6f133363863c5d0efd825b7bffba096
describe
'6255' 'info:fdaE20090811_AAABGAfileF20090811_AABWKJ' 'sip-files00046.QC.jpg'
eaf34226d46cdb7794d9fe1e2a30c4db
237126275ba67d7fe7288441844f148dd2bd2f1b
describe
'974524' 'info:fdaE20090811_AAABGAfileF20090811_AABWKK' 'sip-files00046.tif'
10e3caa9f17b1cb10df0193216aed14b
224514455a2b455b9b8c06adb021bab86595a33d
'2012-03-13T08:09:49-04:00'
describe
'276' 'info:fdaE20090811_AAABGAfileF20090811_AABWKL' 'sip-files00046.txt'
770f79045fe0093dffe28a0b0ddd0cda
2e0d2007e6a2face99be80b2029b3e3b748fe565
describe
'2037' 'info:fdaE20090811_AAABGAfileF20090811_AABWKM' 'sip-files00046thm.jpg'
1bc35ce7320450839f1f73c8af1ad2e5
bf6ca40770fb3ca7a7c3946ea4e3805632d92fdb
describe
'120685' 'info:fdaE20090811_AAABGAfileF20090811_AABWKN' 'sip-files00047.jp2'
a7f718349cf0b43bf15b941ba4e83b0e
b51196b3128b664f9250a2b45a358800bbc91ccd
describe
'83962' 'info:fdaE20090811_AAABGAfileF20090811_AABWKO' 'sip-files00047.jpg'
1975aeea688c2171690f6251b7272ca6
d2a962eeaf64dfdf026d71dd9ef4def4a008bc4b
describe
'38126' 'info:fdaE20090811_AAABGAfileF20090811_AABWKP' 'sip-files00047.pro'
c27db297750fba52810fc76294b99cc5
d2e5cc6dd33bde254a4f1265a86ed566e6866931
describe
'30325' 'info:fdaE20090811_AAABGAfileF20090811_AABWKQ' 'sip-files00047.QC.jpg'
718329785b032b2c443288df774177d8
cc8b4306be993a685be7d1c7ad9fded894e4adc7
describe
'988508' 'info:fdaE20090811_AAABGAfileF20090811_AABWKR' 'sip-files00047.tif'
b1d9fe1c105a8fa1ee2ea4d6dccf0219
849b9a60443d72ae1b622ce75fb03f2b30492ecd
'2012-03-13T08:08:46-04:00'
describe
'1543' 'info:fdaE20090811_AAABGAfileF20090811_AABWKS' 'sip-files00047.txt'
1b414dc194438567fb66ccef383ba089
bec88399fa34f559c8a09867342c45c635374875
describe
Invalid character
'8710' 'info:fdaE20090811_AAABGAfileF20090811_AABWKT' 'sip-files00047thm.jpg'
f34a7460b554ed433eceb6ea32ebfcca
709e1d0209e41f95db08f83072cc07e5450d1009
describe
'141955' 'info:fdaE20090811_AAABGAfileF20090811_AABWKU' 'sip-files00048.jp2'
df86c1cbbd21ef2cc7f88dc63cf58c5c
b9e8fc17294eb7577cce721ec72daab4d33d5b9a
describe
'100158' 'info:fdaE20090811_AAABGAfileF20090811_AABWKV' 'sip-files00048.jpg'
48bd1b03990e676e1d137f85edb98640
228104710ae997a1a8f79dba65ac20b68574e18a
describe
'45625' 'info:fdaE20090811_AAABGAfileF20090811_AABWKW' 'sip-files00048.pro'
44dcb6a1ac75cbcfd25e4a82491c1fe3
a2aa0ae6125ec99a3ee3b3995bc0bdfb33dba75e
describe
'34645' 'info:fdaE20090811_AAABGAfileF20090811_AABWKX' 'sip-files00048.QC.jpg'
60b3d4139d67362468857625529e7171
30ff99e899050e2b5fc7b7da907f7654ad7d1f47
describe
'964761' 'info:fdaE20090811_AAABGAfileF20090811_AABWKY' 'sip-files00048.tif'
efb6e5749e9fcf4aa32f79cf9a970e61
35ff48474fad0bccc845af811f74094d312094f7
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'1858' 'info:fdaE20090811_AAABGAfileF20090811_AABWKZ' 'sip-files00048.txt'
202336b10c031694c4c87c489db35d7e
a3cc46d55d2e3984f31b66cdaa8a4906acbdd7b3
describe
Invalid character
'9657' 'info:fdaE20090811_AAABGAfileF20090811_AABWLA' 'sip-files00048thm.jpg'
be7d71710bfa504076db26d983e2992b
80e6cc85f85286271a8a9b74fb5973311ad659ad
describe
'162462' 'info:fdaE20090811_AAABGAfileF20090811_AABWLB' 'sip-files00049.jp2'
502560e901372dcc423990d8b9f2c13f
22619a9b47600eeefa189045c805d2a264b13a80
describe
'108563' 'info:fdaE20090811_AAABGAfileF20090811_AABWLC' 'sip-files00049.jpg'
898701fd63583e52dabc9a7ad6209050
c61fd48e76767746042b8e6902f74a07c31697df
describe
'49679' 'info:fdaE20090811_AAABGAfileF20090811_AABWLD' 'sip-files00049.pro'
7d8f0420f156bcd9f0b1f17fe09bac55
865e1ac3661affe77414b06799cab4bfb5994eb9
describe
'34683' 'info:fdaE20090811_AAABGAfileF20090811_AABWLE' 'sip-files00049.QC.jpg'
441115553eb1bb656ab3cfe01d19d391
19c51ddf68a8b7531940caae6e720b6ece3f6f18
describe
'info:fdaE20090811_AAABGAfileF20090811_AABWLF' 'sip-files00049.tif'
89846ab14317e61f70770f2cba91e12b
685d459df92ce5108ef2f402bd729eeb39a9783a
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'2052' 'info:fdaE20090811_AAABGAfileF20090811_AABWLG' 'sip-files00049.txt'
0f20b049f30a442784fd4510b3513527
82f72dd867b8c5f07962013d695b4c29dff2017d
describe
Invalid character
'9870' 'info:fdaE20090811_AAABGAfileF20090811_AABWLH' 'sip-files00049thm.jpg'
b96222b209cc42eb03fb288c09d77e87
bb094da6980d846d925a7df033ec5756e477c1e5
'2012-03-13T08:11:45-04:00'
describe
'23687' 'info:fdaE20090811_AAABGAfileF20090811_AABWLI' 'sip-files00050.jp2'
d65817b415213b6a15f4b829a97449b3
03b76fd7e9315976d3a5804a60d40c7904264e4e
describe
'20892' 'info:fdaE20090811_AAABGAfileF20090811_AABWLJ' 'sip-files00050.jpg'
fb42d79576f573dcef912bff0bd329e8
39fdd454d79cdd337ae1d4e0fe2f03714b88ce6a
describe
'5971' 'info:fdaE20090811_AAABGAfileF20090811_AABWLK' 'sip-files00050.pro'
9396e26bfd7006a555ca6d2f31265e95
fbbcb9774edf3e33028aa543fe4bed2a0b4a6cb2
describe
'6665' 'info:fdaE20090811_AAABGAfileF20090811_AABWLL' 'sip-files00050.QC.jpg'
7477014ce6d8df87140f2418dbc5b683
abb82138bdb3041d346f3481fecdc3afd3c1fc1e
describe
'974532' 'info:fdaE20090811_AAABGAfileF20090811_AABWLM' 'sip-files00050.tif'
35c680c104e9ebc2411fcb3f0bbe2eb8
7436a107a1344b4a67c914cbe1508a94999a3883
describe
'326' 'info:fdaE20090811_AAABGAfileF20090811_AABWLN' 'sip-files00050.txt'
a684e4a9a1f23539a1b66ae6791b54a4
addd98ac64342c4cc0d3fc9ac6b9fcf4305faa32
describe
'2368' 'info:fdaE20090811_AAABGAfileF20090811_AABWLO' 'sip-files00050thm.jpg'
e3396eca8ab67bb6fb78d8355220c64f
02fb998559612d1b67dddb32654ec0c2692b9fc7
'2012-03-13T08:11:38-04:00'
describe
'46439' 'info:fdaE20090811_AAABGAfileF20090811_AABWLP' 'sip-files00051.jp2'
9aac073b0ae1b8c226f272c02b9776fa
a863522c0255ece10e1989efafffda9871bd1169
describe
'35482' 'info:fdaE20090811_AAABGAfileF20090811_AABWLQ' 'sip-files00051.jpg'
2a30d714a3fa4b7e177db9a7b2aaab33
d807ced6931abdbe2051e1ceeaf54e3103ad38d5
'2012-03-13T08:11:12-04:00'
describe
'14367' 'info:fdaE20090811_AAABGAfileF20090811_AABWLR' 'sip-files00051.pro'
8fe4219359053bc38f02c8a3f7143444
31dc03db2bb022c0b11b871aead1c347abd7497b
describe
'12319' 'info:fdaE20090811_AAABGAfileF20090811_AABWLS' 'sip-files00051.QC.jpg'
30e5fa6b3e1a1450a4311fb06fa23958
296526183ac5f8c6727bc5e4dc421edd6095e34b
describe
'977524' 'info:fdaE20090811_AAABGAfileF20090811_AABWLT' 'sip-files00051.tif'
5a810e19fcd8c239931daa63006b82ae
82261b98c150aacbcc6427e9d93efde62cc8fc40
describe
'617' 'info:fdaE20090811_AAABGAfileF20090811_AABWLU' 'sip-files00051.txt'
4f04fdd81c27371faf2540bc650a97fa
42e66226960352da8e93d02e294c5d571fc88398
describe
'4264' 'info:fdaE20090811_AAABGAfileF20090811_AABWLV' 'sip-files00051thm.jpg'
b2c122d087823c7fcce5ade308ef17df
5f18199b2dd8ef4f42d5051760fdca6b5d34bbfc
describe
'64052' 'info:fdaE20090811_AAABGAfileF20090811_AABWLW' 'sip-files00052.jp2'
b16b4314049c92bd433bde0ff9e7b7ee
d3955b6e132e6fecaedc8da50344af3a460caff7
describe
'45764' 'info:fdaE20090811_AAABGAfileF20090811_AABWLX' 'sip-files00052.jpg'
6973039ece4f1ba75b8221359aeb850a
cf79216934dd6974fcaae31f7d1716f7b4d30168
describe
'13244' 'info:fdaE20090811_AAABGAfileF20090811_AABWLY' 'sip-files00052.pro'
2f08e341839846f8dca1417f55b491ce
b5fae532c0883e596aa13738a01cb2fc9bea7521
describe
'15231' 'info:fdaE20090811_AAABGAfileF20090811_AABWLZ' 'sip-files00052.QC.jpg'
17d4a753e9514718b39cfdf455977d51
6fbc9bd743716eb7efce94726eb9068766f74364
describe
'980404' 'info:fdaE20090811_AAABGAfileF20090811_AABWMA' 'sip-files00052.tif'
b3cb633b149b20c13c7d159ec7b1cb08
3e205e1686118d9cf7a0242660d49411ffc488a9
'2012-03-13T08:09:26-04:00'
describe
'647' 'info:fdaE20090811_AAABGAfileF20090811_AABWMB' 'sip-files00052.txt'
107620c2904501dca3046c164c5eb46d
4fb23aaf4daeff2bbe605a6cd93b0003ce6bf25b
describe
Invalid character
'4942' 'info:fdaE20090811_AAABGAfileF20090811_AABWMC' 'sip-files00052thm.jpg'
8731b785bb4247c49b787a28f516d0fe
3333b76955af79a24c98d4bc8af5536d1367c7c2
describe
'8765493' 'info:fdaE20090811_AAABGAfileF20090811_AABWMD' 'sip-filesBinder1.pdf'
12d929eca576470c050b57d7b7bcaaef
3bea767cbce806bb99e5f499641449712f62537f
'2012-03-13T08:11:10-04:00'
describe
Malformed outline dictionary
Improperly constructed page tree
Malformed outline dictionary
Malformed outline dictionary
'4113054' 'info:fdaE20090811_AAABGAfileF20090811_AABWMD-norm-0' 'ARCHIVE' 'aip-filesF20090811_AABWMD-norm-0.pdf'
247797d6a35b6a8fc7de8167fd8aeb9d
0adcdb0fb1439efcb1de11f33bde84cf47aa2c02
'2016-05-19T11:55:35-04:00'
describe
'2016-05-19T11:55:21-04:00'
normalize
'1039794' 'info:fdaE20090811_AAABGAfileF20090811_AABWME' 'sip-filesCopyright.jp2'
d815345e48a040534170f6c51e474dd8
9fb7269f72c5541da54ee29d9bd2fcd3c6f451db
describe
'77332' 'info:fdaE20090811_AAABGAfileF20090811_AABWMF' 'sip-filesCopyright.jpg'
2b0c10f2d31ab6889d5c42b4aea76b34
aa744907e2cdf80c49a1464d0fe3afec459048a1
describe
'41595' 'info:fdaE20090811_AAABGAfileF20090811_AABWMG' 'sip-filesCopyright.pro'
b453e9f7561a9313315f12749e1d2052
272f610d30c71b0de8d65f5a6cec691927997bbb
describe
'21025' 'info:fdaE20090811_AAABGAfileF20090811_AABWMH' 'sip-filesCopyright.QC.jpg'
49fdec5d27558f3823c4903a5edadeb8
a5174229426f15c26b851b5fa24854f99300e442
describe
'8334400' 'info:fdaE20090811_AAABGAfileF20090811_AABWMI' 'sip-filesCopyright.tif'
eaca36f95da94faa48ba660eaf610058
111520870f1fef74bb5d969854cea89cb261ae32
'2012-03-13T08:08:58-04:00'
describe
'1929' 'info:fdaE20090811_AAABGAfileF20090811_AABWMJ' 'sip-filesCopyright.txt'
42c64d414ba4478e4a1954526ef923bc
231a1eb17ec5579bc271ce80932284214066e859
describe
'5741' 'info:fdaE20090811_AAABGAfileF20090811_AABWMK' 'sip-filesCopyrightthm.jpg'
a5aa8008cc972ffd28de766ec42b2f2a
b2074b5fa647540c2ba52cb930f7518a935abb5a
describe
'47455' 'info:fdaE20090811_AAABGAfileF20090811_AABWML' 'sip-filesCopyright_archive.pro'
c803988acc9f3a9e1219a2fa80f3a9c4
0216610ecc9c604c7c7f9b0ce316f95d66cfc540
describe
'1040585' 'info:fdaE20090811_AAABGAfileF20090811_AABWMM' 'sip-filesCopyright_archive.tif'
3c4864a086213f44f6d5f8e9e45f1efa
ffa70ccbcf6cb895142dfdd61f6291283cc58604
describe
Invalid DateTime length:
Invalid DateTime length
Invalid DateTime length
'2242' 'info:fdaE20090811_AAABGAfileF20090811_AABWMN' 'sip-filesCopyright_archive.txt'
add8b008791a7d4504a125c1618447df
2192d17ce0e53924025462824b4d87e85355e949
describe
'84774' 'info:fdaE20090811_AAABGAfileF20090811_AABWMO' 'sip-filesUF00091621_00001.mets'
93750105b841935b6601abf9a38b6849
c25f9226e743ffdf27a4b0e03fbbda3b0594d843
'2012-03-13T08:08:45-04:00'
describe
TargetNamespace.1: Expecting namespace 'http://www.uflib.ufl.edu/digital/metadata/ufdc2/', but the target namespace of the schema document is 'http://digital.uflib.ufl.edu/metadata/ufdc2/'.
'2016-05-19T11:55:40-04:00'
xml resolution
TargetNamespace.1: Expecting namespace 'http://www.uflib.ufl.edu/digital/metadata/ufdc2/', but the target namespace of the schema document is 'http://digital.uflib.ufl.edu/metadata/ufdc2/'.
TargetNamespace.1: Expecting namespace 'http://www.uflib.ufl.edu/digital/metadata/ufdc2/', but the target namespace of the schema document is 'http://digital.uflib.ufl.edu/metadata/ufdc2/'.
'111104' 'info:fdaE20090811_AAABGAfileF20090811_AABWMR' 'sip-filesUF00091621_00001.xml'
e0fddfe12de0e0500f9dcf1c29ab6534
8e21fe6a992f237e6fba3221216ba76a22668cf6
'2012-03-13T08:11:57-04:00'
describe
TargetNamespace.1: Expecting namespace 'http://www.uflib.ufl.edu/digital/metadata/ufdc2/', but the target namespace of the schema document is 'http://digital.uflib.ufl.edu/metadata/ufdc2/'.
'2016-05-19T11:55:41-04:00'
xml resolution
TargetNamespace.1: Expecting namespace 'http://www.uflib.ufl.edu/digital/metadata/ufdc2/', but the target namespace of the schema document is 'http://digital.uflib.ufl.edu/metadata/ufdc2/'.
TargetNamespace.1: Expecting namespace 'http://www.uflib.ufl.edu/digital/metadata/ufdc2/', but the target namespace of the schema document is 'http://digital.uflib.ufl.edu/metadata/ufdc2/'.




xml version 1.0 encoding UTF-8
REPORT xmlns http:www.fcla.edudlsmddaitss xmlns:xsi http:www.w3.org2001XMLSchema-instance xsi:schemaLocation http:www.fcla.edudlsmddaitssdaitssReport.xsd
INGEST IEID E6SKO0MYG_NMFBAN INGEST_TIME 2016-06-08T20:32:40Z PACKAGE UF00091621_00001
AGREEMENT_INFO ACCOUNT UF PROJECT UFDC
FILES