US2619419A - Production of color photographic images - Google Patents

Production of color photographic images Download PDF

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Publication number
US2619419A
US2619419A US66837A US6683748A US2619419A US 2619419 A US2619419 A US 2619419A US 66837 A US66837 A US 66837A US 6683748 A US6683748 A US 6683748A US 2619419 A US2619419 A US 2619419A
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Prior art keywords
amino
pyrazolone
color
developing
heterocyclic
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US66837A
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English (en)
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Jacob J Jennen
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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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
    • 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
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F27—FURNACES; KILNS; OVENS; RETORTS
    • F27D—DETAILS OR ACCESSORIES OF FURNACES, KILNS, OVENS OR RETORTS, IN SO FAR AS THEY ARE OF KINDS OCCURRING IN MORE THAN ONE KIND OF FURNACE
    • F27D3/00—Charging; Discharging; Manipulation of charge
    • F27D3/12—Travelling or movable supports or containers for the charge
    • F27D3/123—Furnace cars

Definitions

  • This invention relates to a process for the production of color photographic images by color development in the presence of a color coupler, to photographic developers, photographic material containing color couplers, and to photographic images obtained by such a process.
  • a colored image may be formed by developing a reducible silver salt image in the presence of a compound which couples during the development with the oxidation product of the developing agent and forms a dyestuff which deposits on the developed silver grains.
  • heterocyclo-subtituted pyrazolones As color couplers for producing magenta images, heterocyclo-subtituted pyrazolones have been proposed (British Patent 478,990, accepted January 24, 1938). Said pyrazolones, as well as the likewise formerly proposed pyrazolones without a heterocyclic substituent, produce during color development dyestuffs which absorb blue light, for their absorption curve has a secondary maximum at about 440 mp.
  • X is aryl
  • Y is acyl
  • (Pat. 2,369,489) or X is hydrogen, alkyl or acyl
  • Y is alkyl or aryl
  • Couplers produce dyestuffs which have an absorption maximum at 520 m and which have practically no secondary maximum in the blue region of the spectrum.
  • the most desirable position of he absorption maximum should be, however, at 550 mp.
  • These objects are accomplished by developing 2 a reducible silver salt image with a primary aromatic amino developing agent in the presence. of a color coupler corresponding to the followin formula:
  • Z represents the non-metallic atoms required to complete the heterocyclic ring Y; L represents a methine group or a substituted methine group, and n represents 0 or 1.
  • the dyestuifs produced during color development according to my process have a light-absorption with a maximum which in comparison to the maximum of the prior dyestuffs is shifted toward 550 m and have a superior blue light transmission.
  • the heterocyclic radical Y may contain one or more hetero-atoms, such as N, O, S and Se, as, for example, in Z-pyridyl, 2-quinolyl, Z-benzothiazolyl, 2-benzoxazolyl, 4-quinolyl, 4-chloro-2- quinolyl, 2-chloro-4-quinolyl, 6-meth0xy-2-lepidyl, 4-anilino-2-quinolyl, 4,6-dichloro2-triazinyl, 4-chl0ro-6-p-anisidine-2-triazinyl, 2 thiazolyl, 4,6-dimethylpyrimidyl, benzoselenazolyl, the divalent radical being derived from quinoline by eliminating the hydrogen atoms in the 2 and 4 position, and the trivalent radical being derived from triazine.
  • hetero-atoms such as N, O, S and Se
  • the heterocyclic ring contains a nitrogen atom and is linked to the NH-substituent in the 3 position of the pyrazolone nucleus by its alpha or gamma position.
  • the corresponding heterocyclic compounds having a mercapto group in the alpha or gamma position as to the nitrogen for instance, 4,6-dihydroxy-Z-methylmercapto-pyridine (J. Chem. Soc. (1947) 730) may be condensed with a 3- amino-fi-pyrazolone to give the 3-heterocyclicamino-fi-pyrazolones desired.
  • the corresponding heterocyclic compounds having an alpha or gamma-amino group do not condense with a 3- amino--pyrazolone (compare Curd and Rose, J. Chem. Soc. (1946) 345).
  • aromatic amines may be condensed with a 3-amino-5-pyrazolone, and this reaction is used to prepare the compounds claimed in Patent 2,343,703.
  • Said thiourea derivatives may also be converted by treatment with dimethyl sulphate into an isothiourea derivative which may be reacted with an amino thiophenol so as to form a 3-heterocyclic substituted amino pyrazolone. This method is described in the J. Am. Chem. Soc. 55 (1933) 4989. i
  • 3-amino-pyrazolones the following may be used: 3-amino-5-pyrazolone, l-methyl-S-amino- 5-pyrazclone, 1-phenyl-3-amino-5-pyrazolone, 1- m tolyl S amino 5-pyrazolone, l-m-chlorophenyl 3 amino 5-pyrazolone, l-p-methoxyphenyl 3-amino-5-pyrazolone, l-p-nitrophenyl- 3-amino-5-pyrazolone, 1-(3-pyridyl)-3-amino-5- pyrazolone, 1-( 4-pyridyl) -3-amino-5-pyrazolone, 1-(2-pyridyl) -3-amino-5-pyrazolone, 1-(2-benzothiazolyl) 3-amino-5-pyrazolone, 1-(2-benzoxazolyl)-3-amino-5-pyrazolone.
  • the heterocyclic nucleus is a pyrazolone
  • the 3-heterocyclic amino pyrazolone may be obtained by condensing a hydrazine with a malonate imino ether, as described in the J. Am. Chem. Soc. 66 (1944) 1852. By this method an amino pyrazolone and an imino-bis-pyrazolone are simultaneously formed.
  • the couplers according to my present invention may be used in the developing solution or in a colloid layer, in the latter case either in a light-sensitive layer or in a non-light-sensitive layer adjacent to a sensitive layer or separated therefrom by a water-permeable colloid layer.
  • the couplers When used in a colloid layer of a color photographic material, the couplers generally have to be fast to diffusion. This fastness to diffusion is, for instance, obtained by using in the preparation of the couplers compounds, such as 2- chloro-4-cetylamino-quinoline (which may be prepared by a method analogous to that described in the J. Chem. Soc. (1947) 904), which have a substituent known to have the property of rendering fast to diffusion.
  • Couplers which are fast to diffusion contain advantageously groupings rendering them watersoluble.
  • groupings may also be introduced in my heterocyclic substituted amino pyrazolones, for example, 3-amino-5-pyrazolone is condensed with the di-primary condensation product from the reaction of one equivalent of 4,4'-diamino- 2,2'-stilbene disulphonic acid and two equivalents of a heterocyclic compound containing at least two halogen atoms. Any replaceable halogen atom still remaining may be removed by reaction with a primary amine (British Patent No. 578,014, date of acceptance June 12, 1946; Chem. Abstracts 41 (1947) 6055).
  • a reducible silver salt image may r sult from ad ing to the phot graphic material or developer a compound capable of generating such couplers, for instance, a compound diflering from one of formula II only in that one or both of the hydrogen atoms of the reactive CH2 group of the pyrazolone ring are substituted in a known manner by a substituent split off during development.
  • the aromatic amino compounds which may be used as developing agents in accordance to my present invention include the mono-, diand triamino aryl compounds.
  • mono-amino developing agents may be mentioned amino phenols and amino cresols and their halogen derivatives and amino naphthols.
  • the developing agents which I prefer to use and which give the best results in connection with my present invention are the aromatic orthoand paradlamines, such as paraphenylenediamine and its substitution products.
  • a color developer which may be used to develop an exposed light-sensitive silver halide emulsion layer may have the following composition:
  • color coupler When the color coupler is added to the lightsensitive silver halide emulsion, development may be effected with a mixture of A+B.
  • Example 1 A transparent magenta image is obtained by developing an exposed light-sensitive silver halide emulsion layer with the developer formula:
  • Example 3 --A bluish magenta image (absorption maximum at 542 m is obtained by developing an exposed light-sensitive silver halide emulsion layer with the developer mentioned above and containing a color coupler prepared as follows: 26.5 g. 1-phenyl-3-amino-5-pyrazolone, cc. pyridine and 24 cc. phenyl-isothiocyanate are refluxed for one hour. The reaction mixture is cooled down to 50 C., poured in one litre HCl 2N whilst stirring. The precipitate formed is filtered 01f, washed with water and boiled with ethyl alcohol. A product melting at 227 C. is obtained. 4.2 g.
  • N calculated 18.18, found 18.45 and 18.35; S calculated 10.39, found 10.20 and 10.26.
  • Example 4 A bluish magenta image (absorption maximum at 556 m is obtained by developing an exposed light-sensitive silver halide emulsion layer with the developer mentioned above and containing a color coupler prepared as follows: 3.5 g. 1-phenyl-3-amino-5-pyrazolone and 4.3 g. 2-chloro-benzoselenazole are melted together at C. for 3 minutes. The product obtained is dissolved in ethyl alcohol. The solution is filtered. The filtrate is poured in water. The precipitate formed is dissolved in a solution of NaOl-I. The solution is filtered and acidified. The precipitate is separated by vacuum filtration, dried, dissolved in a little alcohol. The solution is treated with ether and filtered. The filtrate is treated with benzine. A product melting at 190- 193 C. is obtained. Probable formula:
  • Example 5 A magenta image (absorption maximum at 541 m is obtained by developing an exposed light-sensitive silver halide emulsion layer with the developer mentioned above and containing a color coupler prepared as follows: 4-hydroxy-3-amino-diphenyl is boiled with caustic potash and carbon sulphide in ethyl alcohol. The 2-mercapto-5ephenyl benzoxaaole obtained after recrystallization from ethyl alcohol 50% melts at 2l0-212 C. This benzoxazole is heated with phosphorus pentachloride and phosphorus oxychloride on the water bath for 3 hours.
  • the phosphorus oxychloride is distilled under reduced pressure and the residue is washed with petroleum ether and recrystallised from water-alcohol 1'/ l).
  • 2.3 g. of the 5-phenyl-2-chloro-benzoxazole thus obtained and 1.75 g. 1-phenyl-3- amino-5-pyrazolone are refluxed for one hour in cc. acetic acid containing 1 g. sodium acetate.
  • the reaction mixture is poured in water.
  • the precipitate formed is filtered off and recrystallised from ethyl alcohol.
  • Example 7 -A bluish magenta image (absorption maximum at 557 mm) is obtained by developing an exposed light-sensitive silver halide emulsion layer with the developer mentioned above and containing a color coupler prepared as follows: 2.72 g. ammonium salt of l-p-sulfophenyl-3-amino-5-pyrazolone, 2 g. 2.4-dichloroquinazoline and 30 cc. of a mixture of ethyl alcohol and water (l/ 1) are heated on the water bath for 2 hours. The reaction mixture is filtered with suction whilst yet warm, and the filtrate is cooled. The crystals formed in the filtrate are separated by filtering with suction. 1.1 g.
  • X represents a member selected from the group consisting of hydrogen, alkyl, aryl, acyl and a heterocyclic radical
  • Y represents a radical resulting from the subtraction of a hydrogen atom from a carbon atom of a heterocyclic compound containing a nitrogen atom in the ring, said carbon atom being selected from the group consisting of the carbon atoms of the alpha and gamma position to the nitrogen atom.
  • X' represents a member selected from the group consisting of hydrogen, alkyl, aryl, acyl and a heterocyclic radical
  • Y represents a radical resulting from the subtraction of a hydrogen atom from a carbon atom of a heterocyclic compound containing a nitrogen atom in the ring, said carbon atom being selected from the group consisting of the carbon atoms of the alpha and gamma position to the nitrogen atom.
  • X represents a member selected from the group consisting of hydrogen, alkyl, aryl, acyl and a heterocyclic radical
  • Y represents a radical resulting from the subtraction of a hydrogen atom from a carbon atom of a heterocyclic compound containing a nitrogen atom in the ring, said carbon atom being selected from the group consisting of the carbon atoms of the alpha and gamma position to the nitrogen atom
  • said coupler being incorporated in a layer selected fromthe group consisting of said emulsion layer, a layer adjacent thereto, and a layer separated therefrom by a water-permeable colloid layer.
  • X represents a member selected from the group consisting of hydrogen, alkyl, aryl, acyl and a heterocyclic radical
  • Y represents a radical resulting from the subtraction of a hydrogen atom from a carbon atom of a heterocyclic compound containing a nitrogen atom in the ring, said carbon atom being selected from the group consisting of the carbon atoms of the alpha and gamma position to the nitrogen atom.
  • a color photographic developer containing a primary amino aromatic developing agent and l-phenyl -3 -(2-benzothiazo1yl)- amino-5-pyrazclone.
  • a color photographic developer containing a primary amino aromatic developing agent and l-p-sulfo-phenyl 3 -(2- chloro-4- quinazolyl) amino-E-pyrazolone.
  • a color photographic developer containing a primary amino aromatic developing agent and 3-imino-bis-1- (3-chlor0) -phenyl-5-pyrazclone.

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  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Coloring (AREA)
  • Developing Agents For Electrophotography (AREA)
US66837A 1947-12-24 1948-12-22 Production of color photographic images Expired - Lifetime US2619419A (en)

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GB34274/47A GB636988A (en) 1947-12-24 1947-12-24 Improvements in and relating to the production of colour photographic images

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2803544A (en) * 1953-02-13 1957-08-20 Ici Ltd Colour couplers for use in colour photography
US3441414A (en) * 1964-01-30 1969-04-29 Gevaert Photo Prod Nv Production of photographic color images utilizing pyrazolone color couplers
US3952008A (en) * 1973-04-17 1976-04-20 Bayer Aktiengesellschaft Pyrazol-5-ones
US3957814A (en) * 1973-04-17 1976-05-18 Bayer Aktiengesellschaft Pyrazol-5-ones
US3992404A (en) * 1973-04-17 1976-11-16 Bayer Aktiengesellschaft Pyrazol-5-ones
US4000294A (en) * 1973-04-17 1976-12-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4002641A (en) * 1973-12-20 1977-01-11 Bayer Aktiengesellschaft Pyrazole derivatives
US4005215A (en) * 1973-04-17 1977-01-25 Bayer Aktiengesellschaft Pyrazol-5-ones
US4032646A (en) * 1973-04-17 1977-06-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4045571A (en) * 1973-04-17 1977-08-30 Bayer Aktiengesellschaft Pyrazol-5-ones
US4053621A (en) * 1974-06-06 1977-10-11 Bayer Aktiengesellschaft 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them
US4056533A (en) * 1973-04-17 1977-11-01 Bayer Aktiengesellschaft Pyrazol-5-ones
US4061653A (en) * 1972-06-23 1977-12-06 Bayer Aktiengesellschaft 1-Substituted-3-amino-pyrazol-5-ones
US4069334A (en) * 1973-12-20 1978-01-17 Bayer Aktiengesellschaft Pyrazole derivatives
US4081596A (en) * 1973-04-17 1978-03-28 Bayer Aktiengesellschaft Pyrazol-5-ones
USRE30420E (en) * 1973-04-17 1980-10-21 Bayer Aktiengesellschaft Pyrazol-5-ones
US4268592A (en) * 1978-09-07 1981-05-19 Ciba-Geigy Ag Material for color photography
US4288446A (en) * 1973-04-17 1981-09-08 Bayer Aktiengesellschaft Pyrazol-5-ones
US20060040982A1 (en) * 2004-06-29 2006-02-23 Rigel Pharmaceuticals, Inc. 2-Substituted quinoline compounds and their uses
WO2010039186A3 (fr) * 2008-09-23 2010-11-18 Renovis, Inc. Composés utiles en tant que modulateurs de la faah et leurs utilisations

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2179239A (en) * 1935-04-10 1939-11-07 Agfa Ansco Corp Color photography
US2213986A (en) * 1938-04-08 1940-09-10 Ilford Ltd Production of colored photographic images
US2294909A (en) * 1939-02-13 1942-09-08 Du Pont Chemical process and composition
US2311082A (en) * 1941-11-14 1943-02-16 Eastman Kodak Co Pyrazolone coupler for color photography
US2343704A (en) * 1941-11-20 1944-03-07 Eastman Kodak Co Heterocyclic substituted iminopyrazolone coupler
US2343703A (en) * 1942-09-04 1944-03-07 Eastman Kodak Co Pyrazolone coupler for color photography
US2376380A (en) * 1945-05-22 Preparation of amino pyrazolones

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2376380A (en) * 1945-05-22 Preparation of amino pyrazolones
US2179239A (en) * 1935-04-10 1939-11-07 Agfa Ansco Corp Color photography
US2213986A (en) * 1938-04-08 1940-09-10 Ilford Ltd Production of colored photographic images
US2294909A (en) * 1939-02-13 1942-09-08 Du Pont Chemical process and composition
US2311082A (en) * 1941-11-14 1943-02-16 Eastman Kodak Co Pyrazolone coupler for color photography
US2343704A (en) * 1941-11-20 1944-03-07 Eastman Kodak Co Heterocyclic substituted iminopyrazolone coupler
US2343703A (en) * 1942-09-04 1944-03-07 Eastman Kodak Co Pyrazolone coupler for color photography

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2803544A (en) * 1953-02-13 1957-08-20 Ici Ltd Colour couplers for use in colour photography
US3441414A (en) * 1964-01-30 1969-04-29 Gevaert Photo Prod Nv Production of photographic color images utilizing pyrazolone color couplers
US4061653A (en) * 1972-06-23 1977-12-06 Bayer Aktiengesellschaft 1-Substituted-3-amino-pyrazol-5-ones
USRE30420E (en) * 1973-04-17 1980-10-21 Bayer Aktiengesellschaft Pyrazol-5-ones
US3957814A (en) * 1973-04-17 1976-05-18 Bayer Aktiengesellschaft Pyrazol-5-ones
US4000294A (en) * 1973-04-17 1976-12-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4288446A (en) * 1973-04-17 1981-09-08 Bayer Aktiengesellschaft Pyrazol-5-ones
US4005215A (en) * 1973-04-17 1977-01-25 Bayer Aktiengesellschaft Pyrazol-5-ones
US4032646A (en) * 1973-04-17 1977-06-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4045571A (en) * 1973-04-17 1977-08-30 Bayer Aktiengesellschaft Pyrazol-5-ones
US3952008A (en) * 1973-04-17 1976-04-20 Bayer Aktiengesellschaft Pyrazol-5-ones
US4056533A (en) * 1973-04-17 1977-11-01 Bayer Aktiengesellschaft Pyrazol-5-ones
US3992404A (en) * 1973-04-17 1976-11-16 Bayer Aktiengesellschaft Pyrazol-5-ones
US4081596A (en) * 1973-04-17 1978-03-28 Bayer Aktiengesellschaft Pyrazol-5-ones
US4069334A (en) * 1973-12-20 1978-01-17 Bayer Aktiengesellschaft Pyrazole derivatives
US4002641A (en) * 1973-12-20 1977-01-11 Bayer Aktiengesellschaft Pyrazole derivatives
US4053621A (en) * 1974-06-06 1977-10-11 Bayer Aktiengesellschaft 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them
US4268592A (en) * 1978-09-07 1981-05-19 Ciba-Geigy Ag Material for color photography
US20060040982A1 (en) * 2004-06-29 2006-02-23 Rigel Pharmaceuticals, Inc. 2-Substituted quinoline compounds and their uses
US7521560B2 (en) * 2004-06-29 2009-04-21 Rigel Pharmaceuticals, Inc. 2-substituted quinoline compounds and their uses
WO2010039186A3 (fr) * 2008-09-23 2010-11-18 Renovis, Inc. Composés utiles en tant que modulateurs de la faah et leurs utilisations

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FR62605E (fr) 1955-06-15
GB636988A (en) 1950-05-10
FR978214A (fr) 1951-04-11
DE812874C (de) 1951-09-06
DE848011C (de) 1952-09-18

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