US3360372A - Bis(beta-acyloxyethyl)ketones as gelatin hardeners - Google Patents

Bis(beta-acyloxyethyl)ketones as gelatin hardeners Download PDF

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US3360372A
US3360372A US379018A US37901864A US3360372A US 3360372 A US3360372 A US 3360372A US 379018 A US379018 A US 379018A US 37901864 A US37901864 A US 37901864A US 3360372 A US3360372 A US 3360372A
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gelatin
bis
beta
hardeners
ketones
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US379018A
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Donald M Burness
Burton D Wilson
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US379018A priority Critical patent/US3360372A/en
Priority to DEE29714A priority patent/DE1300012B/en
Priority to DE19651472847 priority patent/DE1472847A1/en
Priority to FR30319A priority patent/FR1446163A/en
Priority to GB41889/65A priority patent/GB1128818A/en
Priority to BE677147A priority patent/BE677147A/xx
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/30—Hardeners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

Definitions

  • One object of our invention is to provide gelatin compositions containing compounds having a good hardening effect thereon especially useful in the preparation of photographic products. Another object of our invention is to provide for the hardening of gelatin with compounds relatively free of undesirable photographic effects. A further object of our invention is to provide gelatin hardeners without undesirable physiological properties. A further object of our invention is to provide gelatin compositions containing ketone type hardeners therein. Other objects of our invention will appear herein.
  • compositions comprising gelatin and certain ketone type compounds are useful for obtaining coatings or layers which are resistant to the effect of hot water and to swelling,
  • the compounds of interest as gelatin hardeners are largely of the following general structure:
  • gelatin hardeners have been found to exhibit strong activity as gelatin hardeners substantially free from detrimental photographic effects and toxicity.
  • the use of these hardeners involves incorporating a hardening amount in an aqueous solution of gelatin such as a composition to be used in making photographic products or in a gelatin-silver halide emulsion.
  • the hardener is preferably incorporated in the gelatin composition in a proportion of 05-10 percent based on the weight of the gelatin in the composition.
  • the requisite bis(beta-chloroethyl)ketones are conveniently prepared by a Friedel-Crafts reaction from a dibasic acid halide and ethylene, using aluminum halide as the catalyst.
  • acid halides such as suc cinoyl chloride
  • the reaction referred to does not occur and a more devious route must be used.
  • the intermediates themselves show a slight hardening action in gelatin emulsions.
  • the bis(beta-acyloxyethyl) ketones containing two carbonyl groups in the alkylene or arylene-alkylene chain are new compounds as are compositions thereof with gelatin.
  • the mixture was hydrolyzed on cracked ice drenched with concentrated hydrochloric acid.
  • the layers were separated and the organic layer was washed once with water and dried. The mass must be kept cold throughout the process.
  • the solvent was removd in vacuo, and the dark residue obtained was placed on a column of acid-washed alumina and eluted with benzene.
  • the yellow eluant obtained was concentrated to about one-fifth vol ume in vacuo, and the residual oil was diluted with 23 volumes of ether and cooled.
  • the precipitate was collected and recrystallized, giving colorless crystals which represented a 50-60 percent yield of the 1,10-dichloro- 3,8-decanedione intermediate.
  • This material was employed in gelatin-silver halide photographic emulsions in concentrations of 1, 3 and 6 percent, based on the weight of the gelatin, and swelling in water of layers formed therefrom was found to be materially less than that of a layer of the emulsion without hardener.
  • the material prepared in Example 1 was also incorporated in photographic emulsions in proportions of 1, 3 and 6 percent, and improved resistance to swelling by water of coatings made therewith was obtained. No derogatory effect on the photographic emulsion was noted in either case.
  • EXAMPLE 3 1,10-bis(chl0roacetoxy -3,8-deczmedi0ne
  • the procedure of Example 2 was repeated but modified by using acetone as the solvent and chloracetic acid and sodium chloracetate as the carboxylic acid and the alkali metal salt thereof, respectively.
  • the designated compound was obtained in 99 percent crude yield. Recrystallization from benzene-ligroin gave colorless crystals of 1,10-bis (chloroacetoxy)-3,8-decanedione.
  • This material was incorporated in gelatin-silver halide emulsions in proportions of 1 and 3 percent, based on the weight of the gelatin. It was found that this compound materially reduced the swelling in water of emulsion layers containing it as compared with emulsion layers having no hardener therein and that the hardener was compatible with the photographic characteristics of the gelatin.
  • EXAMPLE 4 1,14-dichlor-3,IZ-Zetradecanedione This intermediate was prepared in a manner similar to that used in Example 1 except that sebacoyl chloride was used in place of adipoyl chloride. Pale yellow crystals were obtained in a yield of about 70 percent.
  • EXAMPLE 5 1,14-diacet0xy-3,1Z-tetradecanedione This compound was prepared in essentially quantitative yield from the product in the preceding example, using a procedure as described in Example 2. This material was incorporated in gelatin-silver halide photographic emulsions in proportions of 1, 3 and 6 percent, based on the weight of the gelatin. The emulsion coated out in the form of layers had a much improved resistance to swelling by water as compared with layers of the emulsion containing no hardener. It was also found that this hardener was compatible with the photographic characteristics of the emulsion.
  • EXAMPLE 6 1,5-dichloro-3-pentanone This intermediate was prepared by the procedure described by Baddeley and co-workers in the Journal of the Chemical Society, page 124 (1953). The resulting compound was a liquid having a boiling point of 64-68" C./ 0.60.8 mm.
  • EXAMPLE 7 1,S-diacetoxy-3-pentanone This compound was prepared by the procedure of Example 2, using as the intermediate the product of the preceding example. This product was incorporated into portions of a gelatin-silver halide photographic emulsion in proportions of 1 and 5 percent, based on the weight of the gelatin, and the layers thereof were compared with layers of the emulsion without hardener. It was found that the resistance to swelling by water of such layers was materially reduced by the presence of the diacetoxy pentanone. It was also found that the hardener was compatible with the photographic properties of the emulsion with which it had been incorporated.
  • the swelling characteristics of the various layers was determined after the layers had been held for three days at 100 F. and 50 percent relative humidity.
  • the swell of the layers was measured by determining the percentage of vertical swelling of the layer after it had been immersed for 5 minutes in water at 68 F. as compared with the depth of the layer prior to contact with the water.
  • EXAMPLE 8 Silver halide photographic emulsions in which the solid portion of the vehicle was composed of 25% gelatin and 75% of the sodium salt of ethyl acrylate-acrylic acid copolymer (80:20 acrylate to acid) were coated out on clear cellulose acetate film base at the rate of 750 mg./sq. ft. In two cases no hardener was used (controls) and in the other cases the hardeners designated were used in the proportions shown. The swell properties of the coatings are also indicated:
  • a composition of matter comprising gelatin and a compound having the formula XCH CH CO (ACO CH CH X X is selected from the group of acyloxy radicals consisting of acetoxy and chloroacetoxy,
  • A is a divalent linkage selected from the group consistg 2)1-10 CH CI-I OCH CH -CH CH SCH CH phenylene and cyclohexylene radicals.
  • a gelatin-silver halide photographic emulsion containing a compound having the formula XCH CH CO(ACO) CH CH X X is selected from the group of acyloxy radicals consisting of acetoxy and chloroacetoxy,
  • A is a divalent linkage selected from the group consistg 2)1-10 -CH CH OCH CH CH CH SCH CH phenylene and cyclohexylene radicals.
  • composition of matter comprising gelatin and 1,10-bis(chloroacetoxy)-3,8-decanedione.
  • composition of matter comprising gelatin and 1,10-bis(chloroacetoxy) -3, S-decanedione.
  • composition of matter comprising gelatin and bis(beta-acetoxyethyl)ketone.
  • decanedione should read l,l0-diacetoxy-3,8-decanedione Signed and sealed this 4th day of November 1969.

Description

United States Patent 3,360,372 BIS(BETA-ACYLOXYETHYL)KETONES AS GELATIN HARDENERS Donald M. Burness and Burton D. Wilson, Rochester,
N.Y., assignors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed June 29, 1964, Ser. No. 379,018 12 Claims. (Cl. 96-111) ABSTRACT OF THE DISCLOSURE Bis(beta-acyloxyethyl)ketones, such as bis( beta-ace- This invention relates to gelatin coating compositions containing bis (beta-acyloxyethyl) ketones or the like therein as hardeners.
Various compounds have been suggested as hardeners for gelatin. In many cases the hardeners which have been used for gelatin have exhibited undesirable photographic effects or have been prone to wander from the layers in which they have been placed. Some compounds suggested as hardening agents for gelatin have been objectionable because of adverse physiological properties.
One object of our invention is to provide gelatin compositions containing compounds having a good hardening effect thereon especially useful in the preparation of photographic products. Another object of our invention is to provide for the hardening of gelatin with compounds relatively free of undesirable photographic effects. A further object of our invention is to provide gelatin hardeners without undesirable physiological properties. A further object of our invention is to provide gelatin compositions containing ketone type hardeners therein. Other objects of our invention will appear herein.
We have found that compositions comprising gelatin and certain ketone type compounds are useful for obtaining coatings or layers which are resistant to the effect of hot water and to swelling, The compounds of interest as gelatin hardeners are largely of the following general structure:
in which X is an acyloxy radical of 2-5 carbon atoms which may or may not be halogen containing, m =0 or 1. A is a divalent linkage selected from the group consisting of (CR per se and (CR in which at least one CR unit is replaced by a replacement selected from the group consisting of CR=CR, O, S, arylene and cycloalkylene radicals, R being selected from the group consisting of H and alkyl groups of 1-4 carbon atoms.
These compounds have been found to exhibit strong activity as gelatin hardeners substantially free from detrimental photographic effects and toxicity. Ordinarily the use of these hardeners involves incorporating a hardening amount in an aqueous solution of gelatin such as a composition to be used in making photographic products or in a gelatin-silver halide emulsion. The hardener is preferably incorporated in the gelatin composition in a proportion of 05-10 percent based on the weight of the gelatin in the composition.
These compounds are conveniently prepared from the corresponding bis (beta-chloroethyl) ketones by the com- 3,360,372 Patented Dec. 26, 1967 bined action thereon of a carboxylic acid and its alkali metal salt using acetone as a solvent if necessary. In the case of liquid carboxylic acids an excess thereof functions well as the solvent when carrying out the reaction at normal temperatures.
The requisite bis(beta-chloroethyl)ketones are conveniently prepared by a Friedel-Crafts reaction from a dibasic acid halide and ethylene, using aluminum halide as the catalyst. In the case of certain acid halides such as suc cinoyl chloride, the reaction referred to does not occur and a more devious route must be used. The intermediates themselves show a slight hardening action in gelatin emulsions. The bis(beta-acyloxyethyl) ketones containing two carbonyl groups in the alkylene or arylene-alkylene chain (for instance, where mw=1 in the general formula) are new compounds as are compositions thereof with gelatin.
The following examples illustrate the preparation of various intermediates, gelatin hardeners and their use as gelatin hardeners in accordance with our invention.
EXAMPLE 1 1,1O-dichl0r0-3,8-decanedione 107 grams of anhydrous aluminum chloride and 450 ml. of dichloromethane were placed in a dry flask. The mass was cooled to 15 C., and then added dropwise was a solution of 73.2 grams of adipoyl chloride in 50 ml. of dichloromethane over a period of 10 minutes, the temperature being kept below 20 C. Ethylene was bubbled in, but no significant absorption occurred until the temperature had risen above 25 C. Fairly rapid absorption occurred at about 30 C.; the temperature was kept below 32 by intermittent cooling. At the termination of the reaction ethylene was no longer absorbed and the solids were in solution. The mixture was hydrolyzed on cracked ice drenched with concentrated hydrochloric acid. The layers were separated and the organic layer was washed once with water and dried. The mass must be kept cold throughout the process. The solvent was removd in vacuo, and the dark residue obtained was placed on a column of acid-washed alumina and eluted with benzene. The yellow eluant obtained was concentrated to about one-fifth vol ume in vacuo, and the residual oil was diluted with 23 volumes of ether and cooled. The precipitate was collected and recrystallized, giving colorless crystals which represented a 50-60 percent yield of the 1,10-dichloro- 3,8-decanedione intermediate.
EXAMPLE 2 1,10-diacetoxy-3,8-decanedi0ne This compound was prepared from the 1,10-dichloro- 3,8-decanedione of the preceding example by the procedure of Arbuzov and Volkov described in J. Gen. Chem. U.S.S.R. (Eng. transl.) 29, 3242 (1959). The crude yield was 93 percent. Repeated recrystallization from cyclohexane gave colorless crystals of 1,10-diacetoxy-3,8-decanedione. This material was employed in gelatin-silver halide photographic emulsions in concentrations of 1, 3 and 6 percent, based on the weight of the gelatin, and swelling in water of layers formed therefrom was found to be materially less than that of a layer of the emulsion without hardener. The material prepared in Example 1 was also incorporated in photographic emulsions in proportions of 1, 3 and 6 percent, and improved resistance to swelling by water of coatings made therewith was obtained. No derogatory effect on the photographic emulsion was noted in either case.
EXAMPLE 3 1,10-bis(chl0roacetoxy -3,8-deczmedi0ne The procedure of Example 2 was repeated but modified by using acetone as the solvent and chloracetic acid and sodium chloracetate as the carboxylic acid and the alkali metal salt thereof, respectively. The designated compound was obtained in 99 percent crude yield. Recrystallization from benzene-ligroin gave colorless crystals of 1,10-bis (chloroacetoxy)-3,8-decanedione. This material was incorporated in gelatin-silver halide emulsions in proportions of 1 and 3 percent, based on the weight of the gelatin. It was found that this compound materially reduced the swelling in water of emulsion layers containing it as compared with emulsion layers having no hardener therein and that the hardener was compatible with the photographic characteristics of the gelatin.
EXAMPLE 4 1,14-dichlor-3,IZ-Zetradecanedione This intermediate was prepared in a manner similar to that used in Example 1 except that sebacoyl chloride was used in place of adipoyl chloride. Pale yellow crystals were obtained in a yield of about 70 percent.
EXAMPLE 5 1,14-diacet0xy-3,1Z-tetradecanedione This compound was prepared in essentially quantitative yield from the product in the preceding example, using a procedure as described in Example 2. This material was incorporated in gelatin-silver halide photographic emulsions in proportions of 1, 3 and 6 percent, based on the weight of the gelatin. The emulsion coated out in the form of layers had a much improved resistance to swelling by water as compared with layers of the emulsion containing no hardener. It was also found that this hardener was compatible with the photographic characteristics of the emulsion.
EXAMPLE 6 1,5-dichloro-3-pentanone This intermediate was prepared by the procedure described by Baddeley and co-workers in the Journal of the Chemical Society, page 124 (1953). The resulting compound was a liquid having a boiling point of 64-68" C./ 0.60.8 mm.
EXAMPLE 7 1,S-diacetoxy-3-pentanone This compound was prepared by the procedure of Example 2, using as the intermediate the product of the preceding example. This product was incorporated into portions of a gelatin-silver halide photographic emulsion in proportions of 1 and 5 percent, based on the weight of the gelatin, and the layers thereof were compared with layers of the emulsion without hardener. It was found that the resistance to swelling by water of such layers was materially reduced by the presence of the diacetoxy pentanone. It was also found that the hardener was compatible with the photographic properties of the emulsion with which it had been incorporated.
The swelling characteristics of the various layers was determined after the layers had been held for three days at 100 F. and 50 percent relative humidity. The swell of the layers was measured by determining the percentage of vertical swelling of the layer after it had been immersed for 5 minutes in water at 68 F. as compared with the depth of the layer prior to contact with the water.
EXAMPLE 8 Silver halide photographic emulsions in which the solid portion of the vehicle was composed of 25% gelatin and 75% of the sodium salt of ethyl acrylate-acrylic acid copolymer (80:20 acrylate to acid) were coated out on clear cellulose acetate film base at the rate of 750 mg./sq. ft. In two cases no hardener was used (controls) and in the other cases the hardeners designated were used in the proportions shown. The swell properties of the coatings are also indicated:
Concentration Hardener Percent of Percent 0! Percent Gelatin Total Swell 1n Vehicle Water Control. 440 20 5 230 20 5 350 60D 20 5 8-200: 1,10-dichloro-3,8-dioxodecane. 8-201: 1,10-diacet0xy-3,B-decanedione. 8-202 bis(b et a-acetoxyethyl) ketone.
In the formula XCH CH CO (ACO CH CI-I X representative compounds which are useful as hardeners in accordance with the invention are as follows:
The invention has been described in considerable detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention as described hereinabove, and as defined in the appended claims.
We claim:
1. A composition of matter comprising gelatin and a compound having the formula XCH CH CO (ACO CH CH X X is selected from the group of acyloxy radicals consisting of acetoxy and chloroacetoxy,
A is a divalent linkage selected from the group consistg 2)1-10 CH CI-I OCH CH -CH CH SCH CH phenylene and cyclohexylene radicals.
2. A gelatin-silver halide photographic emulsion containing a compound having the formula XCH CH CO(ACO) CH CH X X is selected from the group of acyloxy radicals consisting of acetoxy and chloroacetoxy,
A is a divalent linkage selected from the group consistg 2)1-10 -CH CH OCH CH CH CH SCH CH phenylene and cyclohexylene radicals.
3. A composition of matter comprising gelatin and 1,10-bis(chloroacetoxy)-3,8-decanedione.
4. A gelatin-silver halide photographic emulsion containing 1,10-diacetoxy-3,8-decanedione.
5. A composition of matter comprising gelatin and 1,10-bis(chloroacetoxy) -3, S-decanedione.
11. A composition of matter comprising gelatin and bis(beta-acetoxyethyl)ketone.
12. A gelatin-silver halide photographic emulsion containing bis (beta-acetoxyethyl) ketone.
No references cited.
NORMAN G. TORCHIN, Primary Examiner. I. H. RAUBITSCHEK, Assistant Examiner.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,360,372 December 26, 1967 Donald M. Burness et a1.
It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:
Column 4, lines 46 and 60, cancel "of acyloxy radiclas", each occurrence; line 71, "1,lO-bis(chloroacetoxy)3,8-
decanedione" should read l,l0-diacetoxy-3,8-decanedione Signed and sealed this 4th day of November 1969.
(SEAL) Attest:
Edward M. Fletcher, Jr. WILLIAM E. SCHUYLER, JR- Attesting Officer Commissioner of Patents

Claims (1)

  1. 2. A GELATIN-SILVER HALIDE PHOTOGRAPHIC EMULSION CONTAINING A COMPOUND HAVING THE FORMULA
US379018A 1964-06-29 1964-06-29 Bis(beta-acyloxyethyl)ketones as gelatin hardeners Expired - Lifetime US3360372A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US379018A US3360372A (en) 1964-06-29 1964-06-29 Bis(beta-acyloxyethyl)ketones as gelatin hardeners
DEE29714A DE1300012B (en) 1964-06-29 1965-07-15 Use of bis (beta-acyloxyaethyl) ketones for hardening gelatin, photographically gelatin-silver halide emulsions
DE19651472847 DE1472847A1 (en) 1964-06-29 1965-08-27 Use of bis (beta-acyloxyaethyl) ketones for hardening the gelatin of photographic gelatin-silver halide emulsions containing color couplers
FR30319A FR1446163A (en) 1964-06-29 1965-09-03 New gelatin tanning agents and new photographic agents containing these tanning agents
GB41889/65A GB1128818A (en) 1964-06-29 1965-10-02 Gelatin compositions containing hardeners
BE677147A BE677147A (en) 1964-06-29 1966-02-28

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US379018A US3360372A (en) 1964-06-29 1964-06-29 Bis(beta-acyloxyethyl)ketones as gelatin hardeners
DEE29714A DE1300012B (en) 1964-06-29 1965-07-15 Use of bis (beta-acyloxyaethyl) ketones for hardening gelatin, photographically gelatin-silver halide emulsions
DEE0029985 1965-08-27
GB41889/65A GB1128818A (en) 1964-06-29 1965-10-02 Gelatin compositions containing hardeners
BE677147A BE677147A (en) 1964-06-29 1966-02-28

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5187259A (en) * 1990-11-14 1993-02-16 Eastman Kodak Company Chain extended gelatin
US6020398A (en) * 1998-05-22 2000-02-01 Eastman Kodak Company Pigmented ink jet inks for poly (vinylalcohol) receivers
US6045219A (en) * 1998-05-22 2000-04-04 Eastman Kodak Company Pigmented ink jet prints on gelatin overcoated with hardeners
US6074057A (en) * 1998-05-22 2000-06-13 Eastman Kodak Company Pigmented ink jet inks and recording elements containing hardening agents
US6082853A (en) * 1998-05-22 2000-07-04 Eastman Kodak Company Printing apparatus with processing tank
US6161929A (en) * 1998-05-22 2000-12-19 Eastman Kodak Company Inkjet images on PVA overcoated with hardener solution
US6176574B1 (en) 1998-05-22 2001-01-23 Eastman Kodak Company Printing apparatus with spray bar for improved durability
US6254230B1 (en) 1998-05-22 2001-07-03 Eastman Kodak Company Ink jet printing apparatus with print head for improved image durability
US6435678B1 (en) 1998-05-22 2002-08-20 Eastman Kodak Company Waterfast ink jet images treated with hardeners
US20060181658A1 (en) * 2005-02-16 2006-08-17 Eastman Kodak Company Conductive absorption layer for flexible displays
US20060215077A1 (en) * 2005-03-22 2006-09-28 Eastman Kodak Company High performance flexible display with improved mechanical properties
US7507449B2 (en) 2006-05-30 2009-03-24 Industrial Technology Research Institute Displays with low driving voltage and anisotropic particles
DE112007001129T5 (en) 2006-06-29 2009-07-09 Industrial Technology Research Institute Guest host polymer liquid crystal displays on a single substrate

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3359111A (en) * 1965-08-27 1967-12-19 Eastman Kodak Co Hardening compositions with pyrazolone couplers

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DE720930C (en) * 1936-07-28 1942-05-19 Ig Farbenindustrie Ag Process for hardening proteins
US2732301A (en) * 1952-10-15 1956-01-24 Chxcxch

Non-Patent Citations (1)

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5187259A (en) * 1990-11-14 1993-02-16 Eastman Kodak Company Chain extended gelatin
US6176574B1 (en) 1998-05-22 2001-01-23 Eastman Kodak Company Printing apparatus with spray bar for improved durability
US6435678B1 (en) 1998-05-22 2002-08-20 Eastman Kodak Company Waterfast ink jet images treated with hardeners
US6074057A (en) * 1998-05-22 2000-06-13 Eastman Kodak Company Pigmented ink jet inks and recording elements containing hardening agents
US6082853A (en) * 1998-05-22 2000-07-04 Eastman Kodak Company Printing apparatus with processing tank
US6161929A (en) * 1998-05-22 2000-12-19 Eastman Kodak Company Inkjet images on PVA overcoated with hardener solution
US6020398A (en) * 1998-05-22 2000-02-01 Eastman Kodak Company Pigmented ink jet inks for poly (vinylalcohol) receivers
US6254230B1 (en) 1998-05-22 2001-07-03 Eastman Kodak Company Ink jet printing apparatus with print head for improved image durability
US6045219A (en) * 1998-05-22 2000-04-04 Eastman Kodak Company Pigmented ink jet prints on gelatin overcoated with hardeners
US20060181658A1 (en) * 2005-02-16 2006-08-17 Eastman Kodak Company Conductive absorption layer for flexible displays
US7630029B2 (en) 2005-02-16 2009-12-08 Industrial Technology Research Institute Conductive absorption layer for flexible displays
US20060215077A1 (en) * 2005-03-22 2006-09-28 Eastman Kodak Company High performance flexible display with improved mechanical properties
US7557875B2 (en) 2005-03-22 2009-07-07 Industrial Technology Research Institute High 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
US7507449B2 (en) 2006-05-30 2009-03-24 Industrial Technology Research Institute Displays with low driving voltage and anisotropic particles
DE112007001129T5 (en) 2006-06-29 2009-07-09 Industrial Technology Research Institute Guest host polymer liquid crystal displays on a single substrate

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DE1300012B (en) 1969-07-24
DE1472847A1 (en) 1969-05-08
BE677147A (en) 1966-07-18
GB1128818A (en) 1968-10-02

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