US2108602A - Photographic color-forming compounds - Google Patents

Photographic color-forming compounds Download PDF

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Publication number
US2108602A
US2108602A US115972A US11597236A US2108602A US 2108602 A US2108602 A US 2108602A US 115972 A US115972 A US 115972A US 11597236 A US11597236 A US 11597236A US 2108602 A US2108602 A US 2108602A
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Prior art keywords
compounds
compound
color
photographic
development
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US115972A
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Leopold D Mannes
Jr Leopold Godowsky
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to GB8918/35A priority Critical patent/GB458664A/en
Priority to GB14350/37A priority patent/GB478989A/en
Priority to GB11551/36A priority patent/GB478942A/en
Priority to US105616A priority patent/US2126337A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US115972A priority patent/US2108602A/en
Priority to FR836144D priority patent/FR836144A/en
Application granted granted Critical
Publication of US2108602A publication Critical patent/US2108602A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32Colour coupling substances
    • G03C7/36Couplers containing compounds with active methylene groups
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32Colour coupling substances
    • G03C7/34Couplers containing phenols
    • G03C7/346Phenolic couplers

Definitions

  • This invention relates to photographic colorforming. compounds, and more particularly-to compounds which react with the oxidation product ofa photographic developer to form a colored compound in a photographic layer.
  • colored photographic images may be formed by using a developer which forms a colored compound on development.
  • the colored 1 compound thus formed is deposited adjacent the silver image during the development.
  • a colored image may be formed byadding to the developer solution a compound which combines with the oxidation product of the developer and forms a coloring substance.
  • Fischer in U. 3. Patent No. 1,102,028, June 30, 1914. Many of the coupler compounds described by Fischer were, however,
  • a further object is'to provide novel coupler compounds forcolor-forming development.
  • the silver halide is reduced to metallic silver and the de-- veloping agent is oxidized.
  • the aromatic diamine tion or incorporated. in the emulsion layer a dye is formed by the coupling' of thiscompound with the oxidationproduct of the aromatic diamino compound and is deposited in the'gelatin or other silver halide carrier adjacent to the metallic silver grain.
  • the dyes thus formed do not readily Application December 15, 1936, 86ml N0. 115,972 I wander from the place of formation.
  • the couplers may be soluble or insoluble in water, but the water or alkali-soluble couplers are preferably used.
  • the dyes are not physically. attached to the silver grain, so that the silver may be sub- 5 sequently washed out of the carrier layer leav-- ing a pure dye image.
  • the aromatic amino compounds which may be used as developers in our process include the mono-, di-, and triamino aryl compounds-and compounds formed therefrom by substitution in the amino group as well as in the ring, such as alkyl phenylene diamines and alkyl toluylene diamines.. These compounds are usually used in the salt form, such as the hydrochloride or the 16 sulphate which aremore stable than the amines themselves. Examples are diethylparaphenylene diamine hydrochloride, monomethylparaphenylene diamine hydrochloride, and dimethylparaphenylene diamine sulphate. These compounds 20 have an unsubstituted amino group which enables the oxidation product of the developer to couplewith the color-forming compounds.
  • the coupling or color-forming compounds which we contemplate using are acetoacetamides or cyanoacetamides containing areactive methylene group.
  • the colored compounds formed on development result, we believe, from a coupling of the yoxidation" product of the developer to the color-forming compound at its reactive methylene group.
  • our invention is not to be taken as restricted by this explanation of the chemical reaction involved, our present knowledge indicates that the colored compounds are formed in this way.
  • the color-forming compounds which we have found to be useful include compounds having the general formula where Y is an aceto CH3CO) or an cyano (CN,-') group and R. is organic radical such as an' aryl or an azole group.
  • acetoacetanilide i its chain-substituted derivatives, such as. a-bromoacetoacctan'ilide; and its ring-substituted derivatives, such as acetoacet-p-bromanilide, acetoacet-2-chloroanilide, acetoacet-2,4-dichloroani-.-
  • cyanoacetanilides of which cyanoacetanilide itself is an example:
  • Example I Diethyl p.phenylenediamine HCl g 4 2 Sodium sulfite g 5 Sodium carbonate g 30 Water to cc 1,000 B. p-bromoacetoacetanilide g 2 Acetone cc 50 Add 13 to A.
  • Example II A. Dimethyl p.phenylenediamine sulphate g 1 Sodium sulflte g 2 Sodium carbonate g 30 Water to cc 1,000
  • Iso-propyl alcohol cc 100 Add B to A Our process may be employed for the production of colored photographic images in layers of gelatin or other carrier, such as collodion or an organic ester of cellulose.
  • the carrier may be supported by glass or a flexible film, such as cellulose nitrate, cellulose acetate, or other cellulose ester.
  • Theemulsion may be coated as a single layer on the support, or as superposed layers on one or both sides of the support.
  • the superposed layers may be difierentially sensitized, and dyes formed therein may be bleached by an oxidizing agent, such as chromic acid, to colorless, soluble compounds.
  • a color-forming photographic developer comprising an. aromatic amino developing compound and a coupler compound having the general formula 0 Y-CHr-il-NHR where Y is selected from the class consisting of aceto and cyano groups and R. is selected from the class consisting oi aryl and azole groups,
  • a color-forming photographic developer comprising an aromatic amino-developing compound and an acetoacetamide coupler compound with which the developing compound is capable of reacting on development.
  • a color-forming photographic developer comprising an aromatic amino developing compound and a eyanoacetamide coupler compound with which the developing compound is capable of reacting on development.
  • a color-forming photographic developer comprising an aromatic amino developing comcomprising an aromatic amino developing compound and an acetoacetamino azole coupler compound with which the developing compound is capable of reacting on development.
  • a color-forming photographic developer comprising an aromatic amino developing compound and para-bromo-acetoacetanilide.
  • a color-forming photographic developer comprising a pa'raphenylenediamine developing compound and angacetoacetanilide.
  • the method of developing a colored image in a gelatino-silver halide photographic layer which comprises coupling the development product of an aromatic amino developing compound with an acetoacetamide coupler compound simultaneously with the development 0! a silver image inthe layer.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented Feb. 15, 1938 Q PATENT OFFICE PHOTOGRAPHIO COLOR-FORMING CQM- POUND Leopold D. Mannes and Leopold Godowsky, Jr., Rochester, N.- Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No llrawlns.
, 11 Claims. This invention relates to photographic colorforming. compounds, and more particularly-to compounds which react with the oxidation product ofa photographic developer to form a colored compound in a photographic layer This applicationis' a continuation-in-part of our application Serial No. 8519, filed February 27, 1935.
It is known that colored photographic images may be formed by using a developer which forms a colored compound on development. The colored 1 compound thus formed is deposited adjacent the silver image during the development. It is also known that a colored image may be formed byadding to the developer solution a compound which combines with the oxidation product of the developer and forms a coloring substance. The production of colored photographic images in this way was described by Fischer in U. 3. Patent No. 1,102,028, June 30, 1914. Many of the coupler compounds described by Fischer were, however,
' sensitive to sulfite in the developer, and for this reason, Fischer recommended using them in developers containing no sulflte. It is a recognized fact that sodium sulfite, or other sulflte, is a highly desirable constituent of photographic developers, since it tends to prevent oxidation of the developing agent by air. The color-forming developers suggested by Fischer were, therefore, unstable, and were found to oxidize readily on use.
It is therefore an object of the present invention to provide a photographic developer which produces a colored compound simultaneously and in situ with-photographic development, and which is not readily oxidized by air on development. A further object is'to provide novel coupler compounds forcolor-forming development.
These objects are accomplished by the present.
inventionby the use of aromatic diamino developers together with certain specific coupling comv I pounds hereinafter described.
When a silver halide emulsion containing a.
latent photographic image is developed, the silver halide is reduced to metallic silver and the de-- veloping agent is oxidized. The aromatic diamine tion or incorporated. in the emulsion layer, a dye is formed by the coupling' of thiscompound with the oxidationproduct of the aromatic diamino compound and is deposited in the'gelatin or other silver halide carrier adjacent to the metallic silver grain. The dyes thus formed do not readily Application December 15, 1936, 86ml N0. 115,972 I wander from the place of formation. The couplers may be soluble or insoluble in water, but the water or alkali-soluble couplers are preferably used. The dyes are not physically. attached to the silver grain, so that the silver may be sub- 5 sequently washed out of the carrier layer leav-- ing a pure dye image. I
The aromatic amino compounds which may be used as developers in our process include the mono-, di-, and triamino aryl compounds-and compounds formed therefrom by substitution in the amino group as well as in the ring, such as alkyl phenylene diamines and alkyl toluylene diamines.. These compounds are usually used in the salt form, such as the hydrochloride or the 16 sulphate which aremore stable than the amines themselves. Examples are diethylparaphenylene diamine hydrochloride, monomethylparaphenylene diamine hydrochloride, and dimethylparaphenylene diamine sulphate. These compounds 20 have an unsubstituted amino group which enables the oxidation product of the developer to couplewith the color-forming compounds.
The coupling or color-forming compounds which we contemplate using are acetoacetamides or cyanoacetamides containing areactive methylene group. The colored compounds formed on development result, we believe, from a coupling of the yoxidation" product of the developer to the color-forming compound at its reactive methylene group. Although our invention is not to be taken as restricted by this explanation of the chemical reaction involved, our present knowledge indicates that the colored compounds are formed in this way.
The color-forming compounds which we have found to be useful include compounds having the general formula where Y is an aceto CH3CO) or an cyano (CN,-') group and R. is organic radical such as an' aryl or an azole group.
Among the compounds 'which we may use, where Y: aceto and R=an aryl group, are acetoacetanilide i its chain-substituted derivatives, such as. a-bromoacetoacctan'ilide; and its ring-substituted derivatives, such as acetoacet-p-bromanilide, acetoacet-2-chloroanilide, acetoacet-2,4-dichloroani-.-
2 v lide, acetoaoet-2,5-dichloroanilide, acetoacet-mnitroanilide, o-methoxy acetoacetanilide, p-hydroxy acetoacetanilide, acetoacet-p-anisidide,
acetoacetyl-fl-naphthylamine:
and its sulfonate, sodium acetoacet-2-naphthylamine-'l-sulfonate. Also p-phenylazo acetoacetanilide:
and 2-acetoac'etamino anthraquinone:
Where Y =aceto and R=an azole group, we may use l-acetoacetamlno benzothiazole:
and the corresponding phenyl thiazole. Also 2- aceto-acetaminol-methyl carbethoxy. thiazole:
and 2-acetoacetamino-4-(1 coumaronyl) -thiazole:
Where Y=cyano and R=aryl, we may use cyanoacetanilides, of which cyanoacetanilide itself is an example:
o GN-CE-(LNHQ Where the aryl group comprises more than one ring, we may use compounds such as cyanoacetp-naphthalide o err-om--mr The following examples, which are illustrative only, indicate typical developer solutions made according to our invention:
Example I A. Diethyl p.phenylenediamine HCl g 4 2 Sodium sulfite g 5 Sodium carbonate g 30 Water to cc 1,000 B. p-bromoacetoacetanilide g 2 Acetone cc 50 Add 13 to A.
Example II A. Dimethyl p.phenylenediamine sulphate g 1 Sodium sulflte g 2 Sodium carbonate g 30 Water to cc 1,000
B. 4-nitroacetoacetanilide l g 2.5
Iso-propyl alcohol cc 100 Add B to A Our process may be employed for the production of colored photographic images in layers of gelatin or other carrier, such as collodion or an organic ester of cellulose. The carrier may be supported by glass or a flexible film, such as cellulose nitrate, cellulose acetate, or other cellulose ester. Theemulsion may be coated as a single layer on the support, or as superposed layers on one or both sides of the support. The superposed layers may be difierentially sensitized, and dyes formed therein may be bleached by an oxidizing agent, such as chromic acid, to colorless, soluble compounds. The destruction of the dye in this way does not destroy the silver image, and a silver image may be colored, bleached, and recolored a number of times, thus permitting the formation of natural-colored images in superposed layers, as described in ourv prior application, Serial No. 8516.
Although we have referred in the specific examples to the use of our coupler compounds in the developing solution, it is also possible to incorporate them in the sensitive emulsion layer. The silver salt may be combined with the colorformer to form a silver salt of the color-former, the color-former may be absorbed or adsorbed to the sensitive salt, or the color-former may in certain cases, merely be dispersed in the gelatin of 2. A color-forming photographic developer comprising an. aromatic amino developing compound and a coupler compound having the general formula 0 Y-CHr-il-NHR where Y is selected from the class consisting of aceto and cyano groups and R. is selected from the class consisting oi aryl and azole groups,
3. A color-forming photographic developer comprising an aromatic amino-developing compound and an acetoacetamide coupler compound with which the developing compound is capable of reacting on development. a
- 4.- A color-forming photographic developer comprising an aromatic amino developing compound and a eyanoacetamide coupler compound with which the developing compound is capable of reacting on development.
5. A color-forming photographic developer comprising an aromatic amino developing comcomprising an aromatic amino developing compound and an acetoacetamino azole coupler compound with which the developing compound is capable of reacting on development.
7. A color-forming photographic developer comprising an aromatic amino developing compound and para-bromo-acetoacetanilide.
8. A color-forming photographic developer comprising a pa'raphenylenediamine developing compound and angacetoacetanilide.
9. The method of developing a colored image in a gelatino-silver halide photographic layer, which comprises coupling the development product of an aromatic amino developing compound with an acetoacetamide coupler compound simultaneously with the development 0! a silver image inthe layer.
10. The method of developing a colored image in a gelatino-silver halide photographic layer,
which comprises coupling the development prodnot of an aromatic amino developing compound with a cyanoacetamide coupler compound simultaneously with the development of a silver image in the layer. Y i
11. The method of developing a colored image in a geiatino-silver halide photographic layer.
, which comprises coupling the development product or an aromatic amino developing compound with an acetoacetanilide simultaneously with the development 01' a silver image in the layer;
LEOPOLD D. MANNES. LEOPOLD GODOWSKY. Jli.
US115972A 1935-03-21 1936-12-15 Photographic color-forming compounds Expired - Lifetime US2108602A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB8918/35A GB458664A (en) 1935-03-21 1935-03-21 Improvements in and relating to colour forming developers and processes of colour development
GB14350/37A GB478989A (en) 1935-03-21 1936-04-23 Improvements in and relating to colour forming developers and processes of colour development
GB11551/36A GB478942A (en) 1935-03-21 1936-04-23 Improvements in and relating to colour forming developers and processes of colour development
US105616A US2126337A (en) 1935-03-21 1936-10-14 Photographic color-forming compounds
US115972A US2108602A (en) 1935-03-21 1936-12-15 Photographic color-forming compounds
FR836144D FR836144A (en) 1935-03-21 1937-04-23 Improvements to color photography processes and in particular to chromogenic developers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8918/35A GB458664A (en) 1935-03-21 1935-03-21 Improvements in and relating to colour forming developers and processes of colour development
GB11551/36A GB478942A (en) 1935-03-21 1936-04-23 Improvements in and relating to colour forming developers and processes of colour development
US105616A US2126337A (en) 1935-03-21 1936-10-14 Photographic color-forming compounds
US115972A US2108602A (en) 1935-03-21 1936-12-15 Photographic color-forming compounds

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2441491A (en) * 1944-05-12 1948-05-11 Ilford Ltd Cyanacetylamino phenol color formers for color photography
US2455169A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2507180A (en) * 1947-02-08 1950-05-09 Eastman Kodak Co Cyano acetamino color couplers
US2527476A (en) * 1941-03-17 1950-10-24 Gevaert Photo Prod Nv Cyanoacetylhydrazones as photographic color couplers
US2531004A (en) * 1947-11-26 1950-11-21 Gen Aniline & Film Corp Acetonitriles as azo components in diazotypes
US2537001A (en) * 1947-08-06 1951-01-02 Gen Aniline & Film Corp Diazotype layers having cyan acetyl amides as azo components
US2617798A (en) * 1949-02-25 1952-11-11 Ciba Ltd Azo dyestuffs
US2776983A (en) * 1951-08-21 1957-01-08 Durand & Huguenin Ag Acetoacetylamino compounds and a process of making same

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE749975C (en) * 1939-01-13 1945-01-09 Process for the preparation of N-acetoacetyl derivatives of amino compounds
BE442410A (en) * 1940-08-08
US2463838A (en) * 1943-02-18 1949-03-08 Du Pont Polymeric color couplers
US2436007A (en) * 1944-05-12 1948-02-17 Ilford Ltd Dye intermediates for colour photography
US2435173A (en) * 1944-06-07 1948-01-27 Gen Aniline & Film Corp Acetyl n-heterocyclic couplers for color photography
BE459542A (en) * 1945-08-03
US2440954A (en) * 1945-08-23 1948-05-04 Du Pont Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group
US2476008A (en) * 1945-09-28 1949-07-12 Eastman Kodak Co p-hydroxy benzyl alcohol couplers for color photography
US2486440A (en) * 1946-01-10 1949-11-01 Gen Aniline & Film Corp Production of phenazonium dyestuff images
US2532573A (en) * 1946-06-19 1950-12-05 Du Pont Process for preparing vinylthiazoles
US2558777A (en) * 1946-10-15 1951-07-03 Schering Corp Halogenated hydroxystilbazoles and derivatives thereof
BE482021A (en) * 1947-04-30
US2596755A (en) * 1948-01-13 1952-05-13 Eastman Kodak Co Aromatic color couplers containing mercaptan and hydroxyl groups
NL72166C (en) * 1948-01-20
US2600788A (en) * 1949-06-07 1952-06-17 Eastman Kodak Co Halogen-substituted pyrazolone couplers for color photography
DE2705974A1 (en) * 1977-02-12 1978-08-17 Agfa Gevaert Ag METHOD FOR PRODUCING COLOR PHOTOGRAPHIC IMAGES USING NOVEL WHITE COUPLER SUBSTANCES
JPS589938B2 (en) * 1977-04-27 1983-02-23 コニカ株式会社 Photosensitive silver halide multilayer color photographic material
US4126461A (en) * 1977-06-13 1978-11-21 Eastman Kodak Company Black-and-white photographic elements and processes
EP0071570A1 (en) * 1981-06-19 1983-02-09 Ciba-Geigy Ag Process for the production of a photographic black dye image
EP0071569A1 (en) * 1981-06-19 1983-02-09 Ciba-Geigy Ag Photographic silver halide material comprising resorcinol compounds as colour couplers
JPS59172640A (en) * 1983-03-22 1984-09-29 Fuji Photo Film Co Ltd Silver halide photosensitive material
DE3313721A1 (en) * 1983-04-15 1984-10-18 Agfa-Gevaert Ag, 5090 Leverkusen COLOR PHOTOGRAPHIC COLOR COUPLING RECORD MATERIAL

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2527476A (en) * 1941-03-17 1950-10-24 Gevaert Photo Prod Nv Cyanoacetylhydrazones as photographic color couplers
US2455169A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2441491A (en) * 1944-05-12 1948-05-11 Ilford Ltd Cyanacetylamino phenol color formers for color photography
US2507180A (en) * 1947-02-08 1950-05-09 Eastman Kodak Co Cyano acetamino color couplers
US2537001A (en) * 1947-08-06 1951-01-02 Gen Aniline & Film Corp Diazotype layers having cyan acetyl amides as azo components
US2531004A (en) * 1947-11-26 1950-11-21 Gen Aniline & Film Corp Acetonitriles as azo components in diazotypes
US2617798A (en) * 1949-02-25 1952-11-11 Ciba Ltd Azo dyestuffs
US2776983A (en) * 1951-08-21 1957-01-08 Durand & Huguenin Ag Acetoacetylamino compounds and a process of making same

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Publication number Publication date
GB478989A (en) 1938-01-24
GB458664A (en) 1936-12-21
GB478942A (en) 1938-01-24
US2126337A (en) 1938-08-09
FR836144A (en) 1939-01-11

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