GB975930A - Improvements in or relating to the production of coloured photographic images - Google Patents

Improvements in or relating to the production of coloured photographic images

Info

Publication number
GB975930A
GB975930A GB23203/61A GB2320361A GB975930A GB 975930 A GB975930 A GB 975930A GB 23203/61 A GB23203/61 A GB 23203/61A GB 2320361 A GB2320361 A GB 2320361A GB 975930 A GB975930 A GB 975930A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
pentadecyl
give
methyl
prepared
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB23203/61A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB3960856A external-priority patent/GB880862A/en
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Publication of GB975930A publication Critical patent/GB975930A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/50—Acylated on said nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • 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
    • G03C7/18—Processes for the correction of the colour image in subtractive colour photography
    • 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
    • G03C7/34—Couplers containing phenols
    • G03C7/344—Naphtholic couplers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

1, 2-Dimethyl-4-amino-5-tridecyl-pyrazolone-3 is prepared by refluxing myristoyl acetic acid methyl ester with symmetrical dimethyl hydrazine dihydrochloride to give 1, 2-dimethyl-5-tridecyl-pyrazolone-3-hydrochloride, treating this with aqueous sodium nitrite to give the 4-nitrosoderivative, and reducing this with hydrogen under pressure and a nickel catalyst. The corresponding 5-nonyl, 5-undecyl, and 5-pentadecyl-pyrazolones are prepared similarly. 1-Methyl-2-(21-chloro-51-carbomethoxyphenyl) -4-amino-5-pentadecyl-pyrazolone-3 is prepared by diazotizing 3-amino-4-chloro-benzoic acid methyl ester and reducing the diazonium salt with sulphur dioxide to give 2-chloro-5-carbomethoxy-phenylhydrazine hydrochloride, freeing the hydrazine base with sodium acetate and reacting this with palmitoyl acetic acid methyl ester to give 2-(21-chloro-51-carbomethoxyphenyl) -5-pentadecyl-pyrazolone-3. The 1-methyl derivative of this pyrazolone is them made by fusing with methyl p-toluene sulphonate followed by treatment with aqueous sodium acetate and then the 4-nitroso derivative is formed and reduced to the amine as described above. 1 - Methyl - 2 - (p - carbethoxyphenyl) - 4 - amino-5-pentadecyl-pyrazolone-3 is similarly prepared from p-carbethoxyphenylhydrazine and palmitoyl acetic acid methyl ester followed by fusing with methyl p-toluene sulphonate and treatment with sodium acetate to give 1-methyl-2-(p-carbethoxyphenyl)-5-pentadecyl-pyrazolone-3, but then the 4-nitro-derivative is prepared by nitration with nitric acid and this is then reduced with hydrogen and a nickel catalyst. Specifications 975,928, 975,939 and 975,940 also are referred to.
GB23203/61A 1956-12-31 1961-06-27 Improvements in or relating to the production of coloured photographic images Expired GB975930A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3960856A GB880862A (en) 1960-09-27 1956-12-31 Improvements in or relating to the production of coloured photographic images
DEG30580A DE1119666B (en) 1960-09-27 1960-09-27 Process for the preparation of color masked photographic color images by color development

Publications (1)

Publication Number Publication Date
GB975930A true GB975930A (en) 1964-11-25

Family

ID=32394821

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23203/61A Expired GB975930A (en) 1956-12-31 1961-06-27 Improvements in or relating to the production of coloured photographic images

Country Status (5)

Country Link
US (2) US3012884A (en)
BE (1) BE563474A (en)
DE (1) DE1063900B (en)
FR (2) FR1207422A (en)
GB (1) GB975930A (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR79706E (en) * 1959-11-13 1963-04-17
BE587525A (en) * 1960-02-12
BE601938A (en) * 1960-03-29
BE631903A (en) * 1962-05-04
DE2524134A1 (en) * 1975-05-30 1976-12-16 Brill Bernhard Dr VARIO PRESSEUR FOR A Rotogravure PRINTING MACHINE
US4128425A (en) * 1977-05-06 1978-12-05 Polaroid Corporation Photographic developers
EP1764082B1 (en) * 2003-12-01 2011-06-29 L'Oréal 4-5-diamino-N,N-dihydro-pyrazol-3-one derivatives for use in composition for dyeing keratin fibres
FR2866338B1 (en) * 2004-02-18 2006-06-02 Oreal COMPOSITION FOR DYING KERATIN FIBERS COMPRISING AT LEAST ONE DIAMINO-N, N-DIHYDRO-PYRAZOLONE DERIVATIVE
FR2902323B1 (en) * 2006-06-20 2008-08-08 Oreal PROCESS FOR THE PREDICTIBLE DYING OF KERATIN FIBERS BY APPLYING A COMPOSITION CONTAINING A DIAMINO-N, N-DIHYDRO-PYRAZOLONE DERIVATIVE AND A CORE OR DUST-COATED COMPOSITION
FR2902328B1 (en) * 2006-06-20 2008-08-08 Oreal KERATIN FIBER COLORING COMPOSITION COMPRISING 2,3-DIAMINO-6,7-DIHYDRO-1H, 5H-PYRAZOLO 1,2-A PYRAZOL-1-ONE, 6-CHLORO 2-METHYL 5-AMINO PHENOL AND A META -AMINOPHENOL SUBSTITUTE
FR2902327B1 (en) * 2006-06-20 2008-08-08 Oreal KERATIN FIBER COLORING COMPOSITION COMPRISING 2,3-DIAMINO-6,7-DIHYDRO-1H, 5H-PYRAZOLO-1,2-A PYRAZOL-1-ONE, PARA-PHENYLENEDIAMINE OR PARA-TOLUENEDIAMINE AND META-AMINOPHENOL SUBSTITUTES
FR2909281B1 (en) * 2006-11-30 2009-01-16 Oreal ACID PH-COLORING COMPOSITION COMPRISING 2,3-DIAMINO-6,7-DIHYDRO-1H, 5H-PYRAZOLO [1,2-A] PYRAZOL-1-ONE, A COUPLER, A PARTICULAR SURFACTANT AND AN AGENT OXYDANT
FR2909282B1 (en) * 2006-11-30 2009-01-16 Oreal ACID PH-COLORING COMPOSITION COMPRISING 2,3-DIAMINO-6,7-DIHYDRO-1H, 5H-PYRAZOLO [1,2-A] PYRAZOL-1-ONE, PARA-PHENYLENEDIAMINE, META-AMINOPHENOL AND AGENT OXYDANT

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE415830A (en) * 1935-06-07
BE476358A (en) * 1944-05-03
US2428054A (en) * 1945-08-30 1947-09-30 Eastman Kodak Co Photographic color correction using colored couplers
GB652953A (en) * 1948-08-20 1951-05-02 Karl Otto Ganguin Colour photography
NL80125C (en) * 1948-09-15
GB661211A (en) * 1949-02-09 1951-11-21 Ilford Ltd Improvements in or relating to colour photography
BE499957A (en) * 1949-12-13
DE955025C (en) * 1954-03-15 1956-12-27 Agfa Aktiengesellschft Fuer Ph Photographic developer

Also Published As

Publication number Publication date
US3013879A (en) 1961-12-19
DE1063900B (en) 1959-08-20
FR1207422A (en) 1960-02-16
US3012884A (en) 1961-12-12
FR81106E (en) 1967-08-09
BE563474A (en) 1960-06-17

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