US2675314A - Antistain agents for photographic color materials - Google Patents

Antistain agents for photographic color materials Download PDF

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Publication number
US2675314A
US2675314A US220336A US22033651A US2675314A US 2675314 A US2675314 A US 2675314A US 220336 A US220336 A US 220336A US 22033651 A US22033651 A US 22033651A US 2675314 A US2675314 A US 2675314A
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Prior art keywords
color
compound
emulsion
stain
developing
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Expired - Lifetime
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US220336A
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Paul W Vittum
John R Thirtle
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Priority to BE510592D priority Critical patent/BE510592A/xx
Priority to BE530383D priority patent/BE530383A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US220336A priority patent/US2675314A/en
Priority to FR1053636D priority patent/FR1053636A/en
Priority to GB9246/52A priority patent/GB720500A/en
Priority claimed from US370598A external-priority patent/US2704713A/en
Application granted granted Critical
Publication of US2675314A publication Critical patent/US2675314A/en
Priority to GB20685/54A priority patent/GB751912A/en
Priority to FR70307D priority patent/FR70307E/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • G—PHYSICS
    • G07—CHECKING-DEVICES
    • G07F—COIN-FREED OR LIKE APPARATUS
    • G07F7/00—Mechanisms actuated by objects other than coins to free or to actuate vending, hiring, coin or paper currency dispensing or refunding apparatus
    • G07F7/08—Mechanisms actuated by objects other than coins to free or to actuate vending, hiring, coin or paper currency dispensing or refunding apparatus by coded identity card or credit card or other personal identification means
    • G07F7/10—Mechanisms actuated by objects other than coins to free or to actuate vending, hiring, coin or paper currency dispensing or refunding apparatus by coded identity card or credit card or other personal identification means together with a coded signal, e.g. in the form of personal identification information, like personal identification number [PIN] or biometric data
    • G07F7/1008—Active credit-cards provided with means to personalise their use, e.g. with PIN-introduction/comparison system
    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups

Definitions

  • the color R is an alkyl group Such as methyL ethyl lauryl C p s y be added directly to the emulsion hexadecyl, etc, or a substituted alkyl group such as hydroxyethyl, which may contain from 1 to 16 granted 1m 4 Or they may be or more carbon atoms, depending upon the use porated in a sep rate medium w c i to which the anti-stain agent is placed; soluble in the carrier for the sensitive silver B is or and halide as described in the Mannes and Godowsky n is 1 or U. S. Patent granted December 15, Where We refer in t claims" t an group, and Jeney and Patent 2,322,027 20 it is to be understood that we intend to include granted June 15, 1943. substituted alkyl groups.
  • 2,fi-dihydroxyacetophenone oxime however, have interfered with color development by decreasing the amount of dye formed or have yielded developer solutions which are unstable.
  • an object of the presentinvention to provide novel and useful anti-stain agents 40 3 0H for incorporation in silver halide emulsions containing color couplers.
  • a further object is to -c provide suitable anti-stain agents for use in solu- ⁇ CHH" tions used to process such emulsions.
  • a still further object is to provide anti-stain agents H which may be incorporated in photographic developer solutions for developing emulsions containing color couplers and which do not reduce the stability of such solutions.
  • Other objects will 2,5-dihydroxylaurophenone oxime GentlIamlde vention.
  • N-(n-heziadecyl)-2,5-dihydroxy phenylpropionamide Compounds 1, 2, 4, 5, 6, 9, 10, 12 and 14 are designed for use as anti-stain agents to be applied during processing, that is, for treating the emulsion'at any stage not later than development. They may be incorporated'in the developing solution itself or in a pre-bath. Compounds 3, '7, 8, 11, 13 and 15 are suitable for incorporation in the emulsion layer during manufacture; In either case, the anti-stain agent will be present in the emulsion layer during color-forming developmentand'it is essential that the development of the emulsion'layer with the color'developing agent takesplace'inthepresenee of the'antistain agent. When the anti-stain agent isincorporated in the developer or in apre-bath; it diffuses into' the emulsion layer and is present in the'emulsion layer at the timezofdevelopment of the colored image.
  • the following example illustrates a developer solution useful for processing a multi-layer mate rial containing color couplers.
  • Example 1 2-amino-5-diethylaminotoluene hydrochloride g 3 Sodium sulfite (anhydix) g 4 Sodium carbonate (anhydn) g 20. Potassium bromide g 1 Gentisaldoxime g 0.5. 6-nitrobenzimidazole nitrate g 003 'Water cc 1000
  • the following example illustrates a pre-bath which may be used for two minutes immediately preceding color forming development to. secure the advantages of our invention.
  • Example 2 Sodium sulfite (anhydn) g f5 Potassium bromide g' '5 Gentisamide -1 g 1 Water 1 cc-.. 1000
  • the following example illustrates the incorporation of the anti-stain agent in an emulsion layer.
  • Example 3 One gram of the coupler. N-l4-(benzoy1acetamino) -benzene-sulfonyll -N (y-phenylpropyl) p-toluidine and 0.1 gram of the'anti stain agent N-(n-liexadecyl) gentisamide were dissolved at C. in 3 cc. of di-n-butylphthalate. 'This hot' solution was poured with stirring into a solution" containing 18 cc. of10-% gelatin, 21c. of water, and 2 cc. of 10% Alkanol B (sodium triisopropylnaphthalene sulfonate).
  • Compound 7 can be synthesized as follows:
  • Compound 12 can be prepared as follows: on OH -CH:CH2C O OH 02116011 CHzCHaC O O C2H Catalyst
  • Compound 3 can b prepared like compound 12 by using dodecyl alcohol for the esterification.
  • c .t V 7 R cinema 01H WCH'HHH omorno OizH25-Il Catalyst on a I we 1
  • Compound 14 can be prepared from compound 12 by reaction ofthe latter with ammonia.
  • Our agents are particularly useful with sensitive materials coatedon papei' s'upports', where it is especially important to reduce the minimum or fog densities. This applies both to negativedeveloped paper and to reversal paper and transparency materials.
  • A represents an alkyl radical- 2;
  • A represents an alkylamino group
  • the meth- 06. of preventing color stainson color images produced in a silver halide emulsion containing a color coupler, by development of saidemulsion with a primary aromatic amino developing agent, and treating said emulsion at a stage not later than development, with a solution of a compound having the formula:
  • the method of preventing the formation of stain in a photographic silver halide emulsion having a non-difiusing coupler compound there in which comprises developing said emulsion after exposure, with a solution of a primary aromatic amino developing agent containing gentisamide.
  • a color-forming photographic silver halide emulsion having a non-diffusing color coupler incorporated therein, and containing 2,5-dihydroxylaurophenone oxime as an anti-stain agent.
  • a color-forming photographic silver halide emulsion having a, non-difiusing color coupler incorporated therein, and containing N-n-hexadecylgentisamide as an anti-stain agent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Coloring (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Description

layers as described in Fischer U. S[ Patent Most of the compounds available for this purpose. 35
appear from the iollowing descriptionof our ina the development of a silver halide emulsion conone. or more color couplers. witha primary 55 Patented Apr. 13, 1954 ANTISTAIN AGENTS .FOR. rno'roenarmc COLOR MATERIALS Paul W. Vittum, Arnold Weissberger, and John R. Thirtle, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation' of New Jersey No Drawing. Application April 10, 1951,- o l Serial No. 220,336
9 Claims. (Cl. 95-6) 1 p 2 This inventionrelates to color photography and aromatic amino developing agent in the presence particularly to the prevention of color staining or of a compound having the formula fog in photographic emulsions containing color OH couplers. n The incorporation of color-forming components 5 (cmbvl c or couplers in silver halide emulsion layers is well known. These couplers are compounds such as phenolic hydroxyl compounds or compounds with reactive methylene groups which are capable OH of reacting with the oxidation products of priin which A is hydrogen. an alkyl group mary aromatic amino developing agents to proor duce indoaniline or azomethine dyes. The color R is an alkyl group Such as methyL ethyl lauryl C p s y be added directly to the emulsion hexadecyl, etc, or a substituted alkyl group such as hydroxyethyl, which may contain from 1 to 16 granted 1m 4 Or they may be or more carbon atoms, depending upon the use porated in a sep rate medium w c i to which the anti-stain agent is placed; soluble in the carrier for the sensitive silver B is or and halide as described in the Mannes and Godowsky n is 1 or U. S. Patent granted December 15, Where We refer in t claims" t an group, and Jeney and Patent 2,322,027 20 it is to be understood that we intend to include granted June 15, 1943. substituted alkyl groups.
In these p ss s in which e color upl rs The following examples illustrate the general are incorporated in the emulsion layers, the addiclass of compounds which w may tion oi -effective anti stainagents to the emul- L OH sion layers has-been found to confer instability to light upon some of the dye images formed in 0 the emulsion layers. Hydroquinone derivatives and other reducing agents such as ascorbic acid I have been used for this purpose. Because of the 1 instability conferred upon the dye images, it has 011 been found desirable to omit the anti-stain agent eenfi'ilaldmime from the emulsion and this necessitates the use N-oH of an anti-stain agent in the processing solutions.
2,fi-dihydroxyacetophenone oxime however, have interfered with color development by decreasing the amount of dye formed or have yielded developer solutions which are unstable.
It is, therefore, an object of the presentinvention to provide novel and useful anti-stain agents 40 3 0H for incorporation in silver halide emulsions containing color couplers. A further object is to -c provide suitable anti-stain agents for use in solu- \CHH" tions used to process such emulsions. A still further object is to provide anti-stain agents H which may be incorporated in photographic developer solutions for developing emulsions containing color couplers and which do not reduce the stability of such solutions. Other objects will 2,5-dihydroxylaurophenone oxime GentlIamlde vention.
These objects are accomplished by conducting NHCH:
N-methylgentisamide N- (B-hydroxyethyl)-gentisamide- NHCHaCHn OG 010mm;
N- (B-lauroyloxyethyl) -gentisamide N- (n-hexadecyl) -gentisamide N,N-dimethylgentisamide- Methyl gentisate Lauryl gentisate Ethyl [3- (2,5-dihydroiryphenyl) -propionate Lauryl B- (2,5-diliydroxyphenyl) -propionate CH2OHO B-(2,5-dihydroxyphenyl)-propionamide -oH;oH2o
NHCmHa:
N-(n-heziadecyl)-2,5-dihydroxy phenylpropionamide Compounds 1, 2, 4, 5, 6, 9, 10, 12 and 14 are designed for use as anti-stain agents to be applied during processing, that is, for treating the emulsion'at any stage not later than development. They may be incorporated'in the developing solution itself or in a pre-bath. Compounds 3, '7, 8, 11, 13 and 15 are suitable for incorporation in the emulsion layer during manufacture; In either case, the anti-stain agent will be present in the emulsion layer during color-forming developmentand'it is essential that the development of the emulsion'layer with the color'developing agent takesplace'inthepresenee of the'antistain agent. When the anti-stain agent isincorporated in the developer or in apre-bath; it diffuses into' the emulsion layer and is present in the'emulsion layer at the timezofdevelopment of the colored image.
The following example illustrates a developer solution useful for processing a multi-layer mate rial containing color couplers.
Example 1 2-amino-5-diethylaminotoluene hydrochloride g 3 Sodium sulfite (anhydix) g 4 Sodium carbonate (anhydn) g 20. Potassium bromide g 1 Gentisaldoxime g 0.5. 6-nitrobenzimidazole nitrate g 003 'Water cc 1000 The following example illustrates a pre-bath which may be used for two minutes immediately preceding color forming development to. secure the advantages of our invention.
Example 2 Sodium sulfite (anhydn) g f5 Potassium bromide g' '5 Gentisamide -1 g 1 Water 1 cc-.. 1000 The following example illustrates the incorporation of the anti-stain agent in an emulsion layer. I
Example 3' One gram of the coupler. N-l4-(benzoy1acetamino) -benzene-sulfonyll -N (y-phenylpropyl) p-toluidine and 0.1 gram of the'anti stain agent N-(n-liexadecyl) gentisamide were dissolved at C. in 3 cc. of di-n-butylphthalate. 'This hot' solution was poured with stirring into a solution" containing 18 cc. of10-% gelatin, 21c. of water, and 2 cc. of 10% Alkanol B (sodium triisopropylnaphthalene sulfonate). The whole mixture wasthen passed several'timesthrough a colloidmill and the resulting finedispersion wasadded. at 40 C. to 50 cc. of amelt'ed positire-type emulsion. The mixture was then coated on a support in the normal manner and Compound 4 was prepared as follows J. A. C. S.,
on DB (3-0 0,011, N113 Q'oorm,
OH OH Compound 5 can be prepared by the reaction of methyl gentisate (compound 10) with methylamine:
OH OH colon, GENE, CONH;
] H OH Compound 6 was prepared according to U. S. Patent 2,463,462 (1949). 7
Compound 7 can be synthesized as follows:
CONHOH'OH'OH 01111230 0o com CHzCH2C O OH K2520 connomcmooocun Compound 8 was prepared as follows:
- ocolclm on n O n a I Q oicolclm 041051 Pot --r OCOzCzHu OCOzCaHs 000202115 @42001 mcuHuNHi @CONHCuHas-n KOH OCOzCaHi OCOzCzHs 0 ON H C mHn-n Compound 9 can be prepared by the reaction of methyl gentlsate with dimethylamine:
OH OH I OH OH Compound 10 was prepared according to Ann.,
1 Compound ll'was prepared as follows:
Compound 12 can be prepared as follows: on OH -CH:CH2C O OH 02116011 CHzCHaC O O C2H Catalyst Compound 3 can b prepared like compound 12 by using dodecyl alcohol for the esterification. c .t V 7 R cinema 01H WCH'HHH omorno OizH25-Il Catalyst on a I we 1 Compound 14 can be prepared from compound 12 by reaction ofthe latter with ammonia.
on OH Oil?) 1110 0101315 NH cmomocnm OH OH compound l'dcanbe prepared from compound 12 by reaction of the latter with n-hexadecylifiine"or by aseries of 'reacticns such" as those described for compound 8.
CHzCHaCOaCzHt mOuHuNH *developed by reversal to form a colored image.
Our agents are particularly useful with sensitive materials coatedon papei' s'upports', where it is especially important to reduce the minimum or fog densities. This applies both to negativedeveloped paper and to reversal paper and transparency materials.
It will be understood that the examples and modifications 'disclosed 'herein are by way of example only and that our invention is to be taken as limited only by the scope of the appended claims.
I; In aprocess of'color photo'graphyfthemeth- 0d of preventing color stain in a photographic silver halide emulsion having a non-diffusing color coupler therein, which comprises exposing said'emulsion and developing it with a'p'rimary aromatic amino developing agent in the presence of a compound having the formula:
I OH
where A represents an alkyl radical- 2; In a process of color pho'togralphyfthe meth- "od "bf preventing-color photog'ra'p'hlc silver halideemulsion" having a non-diffusing ""cmor coupler-' therein; which comprises exposing -"said emulsion' and' developing it with a primary aromatic amino developing agent in the presence of a 'com'pound haiving the formula:
CHzCHzC ONHCit u-n n- C IOHSSNHB then K OH CHaCHzCO C1 OCOzCzHs aromatic "amino' developing agent inthe presence of acom'pound having the formula:
where A represents an alkylamino group.
4. In a process of color photography, the meth- 06. of preventing color stainson color images produced in a silver halide emulsion containing a color coupler, by development of saidemulsion with a primary aromatic amino developing agent, and treating said emulsion at a stage not later than development, with a solution of a compound having the formula:
where A is selected from the class consisting of hydrogen, R, --NI-I2, -NHR, NR2 and OR; B. is an alkyl group of less than 11 carbon atoms; B is selected from the class consisting of =NOH and =0; and n is a positive integer from 1 to 2.
5. The method of preventing the formation of stain in a photographic silver halide emulsion having a non-diffusing coupler compound therein, which comprises developing said emulsion after exposure, with a solution of a primary aromatic amino developing agent containing gentlsaldoxl'mc,
6. The method of preventing the formation of stain in a photographic silver halide emulsion having a non-difiusing coupler compound there in, which comprises developing said emulsion after exposure, with a solution of a primary aromatic amino developing agent containing gentisamide.
7. The method of preventing the formation of stain in a photographic silver halide emulsion having a non-diffusing coupler compound therein, which comprises developing said emulsion after exposure, with a solution of a primary aromatic amino developing agent containing N-(B- hydroxyethyl) -gentisamide.
8. A color-forming photographic silver halide emulsion having a non-diffusing color coupler incorporated therein, and containing 2,5-dihydroxylaurophenone oxime as an anti-stain agent.
10 9. A color-forming photographic silver halide emulsion having a, non-difiusing color coupler incorporated therein, and containing N-n-hexadecylgentisamide as an anti-stain agent.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date U 2,301,387 Evans et a1 Nov. 10., 1942 2,360,290 Vittum et a1 Oct. 10, 1944 2,384,658 Vittum Sept. 11, 1945 2,403,721 Jelley et a1. July 9, 19 6 FOREIGN PATENTS 15 Number Country Date 501,040 Great Britain May 10, 1937 545,732 Great Britain June 10, 1942

Claims (1)

1. IN A PROCESS OF COLOR PHOTOGRAPHY, THE METHOD OF PREVENTING COLOR STAIN IN A PHOTOGRAPHIC SILVER HALIDE EMULSION HAVING A NON-DIFFUSING COLOR COUPLER THEREIN, WHICH COMPRISES EXPOSING SAID EMULSION AND DEVELOPING IT WITH A PRIMARY AROMATIC AMINO DEVELOPING AGENT IN THE PRESENCE OF A COMPOUND HAVING THE FORMULA:
US220336A 1951-04-10 1951-04-10 Antistain agents for photographic color materials Expired - Lifetime US2675314A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE510592D BE510592A (en) 1951-04-10
BE530383D BE530383A (en) 1951-04-10
US220336A US2675314A (en) 1951-04-10 1951-04-10 Antistain agents for photographic color materials
FR1053636D FR1053636A (en) 1951-04-10 1952-04-09 Improvements in color photography
GB9246/52A GB720500A (en) 1951-04-10 1952-04-10 Improvements in colour photographic processes and materials
GB20685/54A GB751912A (en) 1951-04-10 1954-07-15 Improvements in colour photographic processes and materials
FR70307D FR70307E (en) 1951-04-10 1954-07-19 Improvements in color photography

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US220336A US2675314A (en) 1951-04-10 1951-04-10 Antistain agents for photographic color materials
US370598A US2704713A (en) 1953-07-27 1953-07-27 Nu-alkylhomogentisamide antistain agents for photographic materials

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944899A (en) * 1956-10-04 1960-07-12 Eastman Kodak Co Stabilization of photographic silver halide emulsions
US2956876A (en) * 1957-09-09 1960-10-18 Eastman Kodak Co Mercapto heterocyclic addenda for reversal color development
US3141771A (en) * 1961-02-01 1964-07-21 Eastman Kodak Co Aldehyde scavengers for photographic silver halide developers
US3168400A (en) * 1961-05-22 1965-02-02 Eastman Kodak Co Rapid processing of photographic color materials
US3174862A (en) * 1959-09-11 1965-03-23 Agfa Ag Process for improving the color reproduction in color photographic material
US3459548A (en) * 1967-07-24 1969-08-05 Polaroid Corp Scavengers for oxidized developing agent
US4198239A (en) * 1976-09-04 1980-04-15 Agfa-Gevaert, A.G. Color photographic materials containing an antistain agent
US4277553A (en) * 1978-09-20 1981-07-07 Konishiroku Photo Industry Co., Ltd. Light-sensitive color photographic material
US4357419A (en) * 1981-04-02 1982-11-02 Minnesota Mining And Manufacturing Company Covering power in films
US4430426A (en) 1982-06-04 1984-02-07 Minnesota Mining And Manufacturing Company Stabilization of silver halide emulsions
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US4741980A (en) * 1985-09-19 1988-05-03 Konishiroku Photo Industry Co., Ltd. Method for increasing color-fastness of organic coloring matter
US5264332A (en) * 1990-10-08 1993-11-23 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5561036A (en) * 1995-03-30 1996-10-01 Eastman Kodak Company Photographic elements containing scavengers for oxidized developing agent

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1247632A (en) * 1981-06-19 1988-12-28 Frederick H. Howell Hydroquinones
CA1178838A (en) * 1981-06-19 1984-12-04 David G. Leppard Photographic material including a colour coupler- containing silver halide layer and an associated hydroquinone compound

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB501040A (en) * 1936-05-09 1939-02-20 Kodak Ltd Improvements in colour photographic development
GB545732A (en) * 1936-05-09 1942-06-10 Kodak Ltd Improvements in and relating to photographic colour developers
US2301387A (en) * 1939-12-09 1942-11-10 Eastman Kodak Co Reducing aerial oxidation of photographic developers
US2360290A (en) * 1941-07-31 1944-10-10 Eastman Kodak Co Preventing formation of color fog in emulsions
US2384658A (en) * 1943-07-10 1945-09-11 Eastman Kodak Co Color photography
US2403721A (en) * 1943-09-23 1946-07-09 Eastman Kodak Co Preventing color fog in photographic material

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB501040A (en) * 1936-05-09 1939-02-20 Kodak Ltd Improvements in colour photographic development
GB545732A (en) * 1936-05-09 1942-06-10 Kodak Ltd Improvements in and relating to photographic colour developers
US2301387A (en) * 1939-12-09 1942-11-10 Eastman Kodak Co Reducing aerial oxidation of photographic developers
US2360290A (en) * 1941-07-31 1944-10-10 Eastman Kodak Co Preventing formation of color fog in emulsions
US2384658A (en) * 1943-07-10 1945-09-11 Eastman Kodak Co Color photography
US2403721A (en) * 1943-09-23 1946-07-09 Eastman Kodak Co Preventing color fog in photographic material

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944899A (en) * 1956-10-04 1960-07-12 Eastman Kodak Co Stabilization of photographic silver halide emulsions
US2956876A (en) * 1957-09-09 1960-10-18 Eastman Kodak Co Mercapto heterocyclic addenda for reversal color development
US3174862A (en) * 1959-09-11 1965-03-23 Agfa Ag Process for improving the color reproduction in color photographic material
US3141771A (en) * 1961-02-01 1964-07-21 Eastman Kodak Co Aldehyde scavengers for photographic silver halide developers
US3168400A (en) * 1961-05-22 1965-02-02 Eastman Kodak Co Rapid processing of photographic color materials
US3459548A (en) * 1967-07-24 1969-08-05 Polaroid Corp Scavengers for oxidized developing agent
US4198239A (en) * 1976-09-04 1980-04-15 Agfa-Gevaert, A.G. Color photographic materials containing an antistain agent
US4277553A (en) * 1978-09-20 1981-07-07 Konishiroku Photo Industry Co., Ltd. Light-sensitive color photographic material
US4357419A (en) * 1981-04-02 1982-11-02 Minnesota Mining And Manufacturing Company Covering power in films
US4430426A (en) 1982-06-04 1984-02-07 Minnesota Mining And Manufacturing Company Stabilization of silver halide emulsions
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
US4741980A (en) * 1985-09-19 1988-05-03 Konishiroku Photo Industry Co., Ltd. Method for increasing color-fastness of organic coloring matter
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US5264332A (en) * 1990-10-08 1993-11-23 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5561036A (en) * 1995-03-30 1996-10-01 Eastman Kodak Company Photographic elements containing scavengers for oxidized developing agent
EP0735418A1 (en) * 1995-03-30 1996-10-02 Eastman Kodak Company Photographic elements containing scavengers for oxidized developing agent

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BE530383A (en)
GB751912A (en) 1956-07-04
FR1053636A (en) 1954-02-03
FR70307E (en) 1959-04-06
GB720500A (en) 1954-12-22
BE510592A (en)

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