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Publication numberUS3232763 A
Publication typeGrant
Publication dateFeb 1, 1966
Filing dateMar 14, 1963
Priority dateMar 14, 1963
Publication numberUS 3232763 A, US 3232763A, US-A-3232763, US3232763 A, US3232763A
InventorsBurness Donald M, Wilson Burton D
Original AssigneeEastman Kodak Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Gelatin compositions containing a bisisomaleimide hardener
US 3232763 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent C) M 3 232 763 GELATIN coMPosmoNs CONTAINING A BISISOMALEIMIDE HARDENER Donald M. Burness and Burton D. Wilson, Rochester,

3,232,763 Patented Feb. 1, 1966 Example 1 The procedure described by Cotter, Sauers and Whelan, Journal of Organic Chemistry, volume 26, page 10 (1961), was followed using commercial dicyclohexyl- N.Y. assignors to Eastman Kodak Compan Roches- 5 carbodiimide. The product obtained was in the form of 9 ter, N.Y., a corporation of New Jersey colorless crystals in 52% yield which product had a meltl\o Drawing. Filed Mar- 14, 1 ing point of 96.597.5 C. Samples of this product, Claims? hexamethylene bisisomaleimide, were added to separate portions of a high speed gelatin-silver bromoiodide emul- Thls lnvemlon relates to gelatm coatmg compqsltlons 10 sion, which had been panchromatical-ly sensitized with a d layers prepared therefrom composed of ge af and cyanine dye, in the proportions indicated inthe table. as a hardener therein an alkylene 'bislsomaleirmde, the AS a comparison Samples of the emulsion Without illkylelflfi e 0f 10carb0n atoms" hardener added and with hexamethylene bismaleimide in VaTlOllS blsmalefmldes a been Proposed as gelatm corresponding proportion were taken. Each of these hardeners as for 1113mm? 111 Patent 2,992,109 of emulsion samples was coated out onto cellulose acetate C. F. H. Allen and Belgian Patent 579,914 of G evaert fil Support at a coverage f 432 f Silver and 930 Photo-Products. It has been noted that incorporation of mg of gelatin er square foot. A sample of each film heXamethylene bisfnilleimide gelatin flompositifm coating was exposed on an Eastman 1B sensitometer, roduces only a slight increase, if at all, in the melting rocessed for 5 minutes in Kodak DK-SO developer, points of the gelatin layers obtained therefrom. fixed, washed and dried with the following results:

Cone, Rel. Percent Ret. M. Compound Name g./10O Speed 7 Fog Swell F? F.

g. of gel 1 Control N,N-Hexamethylene-bis 100 1 32 0 14 716 84 88 mgt imideu 23 1.37 0.12 477 82 91 2 N,N-Hexamethylenebis- 1 46 0 l 469 77 92 isomaleimide 0.6 74 1.33 0.11 433 94 123 Do 1.2 54 1.30 0.10 329 None 212 1 Vertical swell 2 Reticulation, 3 Melting Point, F.

ll 0 monanN o-mr where n is an integer of 4 to 10.

We have found that these compounds of our invention when incorporated in gelatin layers at a concentration as little as 0.5% of the gelatin will effectively harden the gelatin so as to increase the melting point and resistance to swelling by Water of layers prepared therefrom. We have found that these hardeners have no detrimental eifect on the photographic properties of products in whose preparation they are used.

The following examples illustrate the use of compounds in accordance with the invention for gelatin hardening comparing same with the eifectiveness of bismaleimide hardeners.

in? water without processing.

perature at this point designated the melting point of the gelatin containing layer.

Example 2 A slurry of 51.2 grams of N,N-tetramethylene-bismaleamic acid in 500 ml. of dichloromethane was stirred vigorously while a solution of 82.5 grams of commercial dicyclohexylcarbodiimide in ml. of dichloromethane Was added dropwise over a period of 50 minutes. The mixture was stirred for 24 hours, then cooled and the solids were removed by filtration. The crude residue was extracted with hot benzene, filtered and evaporated to dryness. The residue was slurried with cold ether and filtered. The crude, colorless crystalline solid was recrystallized With benzene-ether to give N,N'-tetramethylenebisisomaleimide having a melting point of 146.5 to 148.5 C.

The tetramethylene bisisomaleimide prepared in Example 2 was added to separate portions of high-speed silver bromoiodide emulsion which had been panchromatically sensitized with a cyanine dye, in the proportions indicated in the table. A sample of the emulsion without hardener was also taken. Each emulsion sample was coated onto a cellulose acetate film support at a coverage of 459 mg. of silver and 1040 mg. of gelatin per square foot. A sample of each film coating was exposed on an Eastman 1B sensitometer, processed for five mine; utes in Kodak DK-SO developer, fixed, Washed and dried with the following results:

2. A composition comprising gelatin containing therein hexamethylene bisisomaleimide.

Cone., Rel. Bet, M.PI, Compound Name gJlOll Speed 1 Fog Swell 1 F. F.

g. of gel Control- 100 l. 02 17 730 74 85 N,N'-Tetramethylenebisiso- I maleimide 3 76 l. 22 12 320 None 212 D0 6 59 1. l7 10 280 None 212 1 Taken after developing, fixing and washing.

HC-O o n being an integer of 4 to 10.

3. A composition comprising gelatin containing therein tetrarnethylene bisisomaleimide. V

4. A gelatin-silver halide photographic emulsion containing hexamethylene bisisomaleimide.

5. A gelatin-silver halide photographic emulsion containing therein tetramethylene bisisomaleimide.

References Cited by the Examiner UNITED STATES PATENTS 2,726,162 12/1955 Allen et al. 106125 2,899,327 8/ 1959 Christopher et al. 106125 2,992,109 7/1961 Allen 96sl11 2,994,611 8/1961 Heyna et al. 96-111 OTHER REFERENCES Chemical Abstracts, v01. 55 (1961), pp. 19782 to NORMAN G. TORCHIN, Primary Examiner.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2726162 *Dec 1, 1951Dec 6, 1955Eastman Kodak CoHardening of gelatin
US2899327 *Dec 5, 1955Aug 11, 1959 Glue setting accelerators
US2992109 *Jun 17, 1960Jul 11, 1961Eastman Kodak CoHardening of photographic emulsions
US2994611 *Mar 13, 1959Aug 1, 1961Hoechst AgHardening of protein
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3462273 *Jul 11, 1966Aug 19, 1969Agfa Gevaert Nv2-dioxolanones (carboxylic acid esters) protein hardeners
US5744574 *Dec 5, 1995Apr 28, 1998Minnesota Mining And Manufacturing CompanyIsomaleimides and polymers derived therefrom
US6020398 *May 22, 1998Feb 1, 2000Eastman Kodak CompanyPigmented ink jet inks for poly (vinylalcohol) receivers
US6045219 *May 22, 1998Apr 4, 2000Eastman Kodak CompanyPigmented ink jet prints on gelatin overcoated with hardeners
US6074057 *May 22, 1998Jun 13, 2000Eastman Kodak CompanyPigmented ink jet inks and recording elements containing hardening agents
US6082853 *May 22, 1998Jul 4, 2000Eastman Kodak CompanyPrinting apparatus with processing tank
US6161929 *May 22, 1998Dec 19, 2000Eastman Kodak CompanyProviding ink jet ink receiving layer containing acetoacetylated polyvinyl alcohol, depositing pigment-based ink jet ink to form image on polyvinyl alcohol-containing ink receiving layer, applying hardener; improved durability
US6176574May 22, 1998Jan 23, 2001Eastman Kodak CompanyPrinting apparatus with spray bar for improved durability
US6254230May 22, 1998Jul 3, 2001Eastman Kodak CompanyInk jet printing apparatus with print head for improved image durability
US6435678May 22, 1998Aug 20, 2002Eastman Kodak CompanyDepositing pigment based ink then hardener solution on glossy paper coated with acetoacetylated polyvinyl alcohol and additional hardener; wet adhesion; waterfast images
US7507449May 30, 2006Mar 24, 2009Industrial Technology Research InstituteHigh contrast reflective display comprising substrate, imaging layer comprising uniformly thick, close-packed, ordered monolayer of domains of electrically modulated material in fixed polymer matrix, barrier layer conductive in direction perpendicular to substrate, electroconductive layer; low cost
US7557875Mar 22, 2005Jul 7, 2009Industrial Technology Research InstituteHigh performance flexible display with improved mechanical properties having electrically modulated material mixed with binder material in a ratio between 6:1 and 0.5:1
US7630029Feb 16, 2005Dec 8, 2009Industrial Technology Research InstituteBistable, reflective
DE112007001129T5Jun 22, 2007Jul 9, 2009Industrial Technology Research InstituteGast-Wirt-Polymer-Flüssigkristallanzeigen auf einem einzigen Substrat
EP0124795A2Apr 11, 1984Nov 14, 1984Fuji Photo Film Co., Ltd.Silver halide photographic emulsion
EP2385425A1May 2, 2011Nov 9, 2011Fujifilm CorporationSilver halide photographic light-sensitive material for movie
WO2008038764A1Sep 28, 2007Apr 3, 2008Fujifilm CorpSpontaneous emission display, spontaneous emission display manufacturing method, transparent conductive film, electroluminescence device, solar cell transparent electrode, and electronic paper transparent electrode
WO2012035314A1Sep 7, 2011Mar 22, 2012Fujifilm Imaging Colorants LimitedPhotographic paper
Classifications
U.S. Classification430/623