GB880862A - 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
GB880862A
GB880862A GB3960856A GB3960856A GB880862A GB 880862 A GB880862 A GB 880862A GB 3960856 A GB3960856 A GB 3960856A GB 3960856 A GB3960856 A GB 3960856A GB 880862 A GB880862 A GB 880862A
Authority
GB
United Kingdom
Prior art keywords
phenyl
methyl
pyrazolone
pentadecyl
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
GB3960856A
Inventor
Maurice Antoine De Ramaix
Jan Jaeken
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
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Priority to BE563474D priority Critical patent/BE563474A/xx
Priority to US705508A priority patent/US3012884A/en
Priority to FR1207422D priority patent/FR1207422A/en
Priority to DEG23643A priority patent/DE1063900B/en
Priority to US70914A priority patent/US3013879A/en
Priority to GB23203/61A priority patent/GB975930A/en
Priority to FR874185A priority patent/FR81106E/fr
Publication of GB880862A publication Critical patent/GB880862A/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
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • 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
    • C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
    • C07D231/50—Acylated on said nitrogen atom
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

2 - Phenyl - 3 - methyl - 4 - amino - pyrazolone - 5 is prepared by reducing the corresponding 4-phenylazo derivative with hydrogen and a nickel catalyst. Similarly, 1-benzoyl-2-phenyl-3-methyl- and 1-phenylsulphonyl-2-phenyl-3-methyl-, 4-phenylazo-5-pyrazolones are reduced to the corresponding 4-amino compounds. 2 - p (a - hexadecenyl - succinylamido) phenyl - 3-methyl-4-amino-pyrazolone-5 is similarly prepared from the 4-phenylazo compound using palladium as catalyst. Reduction of 1-phenyl-3 pentadecyl-4-phenylazo-5-pyrazolone with zinc in acetic acid and acetic anhydride gives the 4-diacetylamino derivative. 1 - phenyl - 2 - hexadecyl - 3 - methyl - 4 - amino-5-pyrazolone is prepared by treating 1-phenyl-2-hexadecyl-3-methyl-5-parazolone with sodium nitrite and concentrated hydrochloric acid to give the 4-nitroso compound and reducing this with hydrogen and nickel catalyst. Similarly, 1 - phenyl - 2 - methyl - 3 - pentadecyl -, 1 - phenyl - 2 - methyl - 3 - [m - (a - hexadecenyl - succinyl - amido) phenyl]-, and the methyl ester of 1-[ - p (succinylamido) phenyl] - 2 - methyl - 3 - pentadecyl-, 5-pyrazolones are converted to the 4-nitroso compounds which are then reduced to the 4-amino compounds (in the latter mentioned case with zinc and hydrochloric acid). 1-Benzoyl-(or 1-phenylsulphonyl) 2-phenyl-3-methyl-4-phenylazo-5-pyrazolone is prepared by adding benzoyl chloride (or benzene sulphonyl chloride) to 2-phenyl-3-methyl-4-phenylazo-5-pyrazolone in the presence of aqueous sodium hydroxide. 1- Phenyl - 2 - hexadecyl - 3 - methyl - 5 - pyrazolone is prepared by fusing 1-phenyl-3-methyl-5-pyrazolone with cetyl-p-toluene sulphonate. Similarly, 1-phenyl-3-pentadecyl-(or 3-p-nitrophenyl) and in 1-p-nitrophenyl-3-pentadecyl-4-pyrazolones are fused with methyl-p-toluene sulphonate to give the 2-methyl derivatives. 1-Phenyl-2-methyl-3-p-nitrobenzoylamino-5 - pyrazolone is prepared by adding p-nitrobenzoyl chloride and aqueous sodium hydroxide to 1 - phenyl - 2 - methyl - 3 - amino - 5 - pyrazolone. The product is reduced to the 3-p-aminobenzoylamino derivative with H2 and nickel catalyst and then reacted with a -hexadecenyl succinic anhydride to give the 3-[p-(a -hexadecenylsuccinylamido) benzoylamino]-5-pyrazolone. By reacting this with the diazonium sulphate from p-chloroaniline and reducing with zinc and hydrochloric acid, 1 - phenyl - 2 - methyl - 3 - [p - (a - hexa - decenylsuccinylamido) benzoylamino] - 4 - amino - 5-pyrazolone is formed. 2-p-nitrophenyl-3-methyl-5-pyrazolone is prepared by adding phosphorus trichloride to a -acetyl-b -(p-nitrophenyl)-hydrazine and acetoacetic acid ethyl ester. The product is reduced to the 2-p-aminophenyl derivative with H2 and nickel catalyst and then reacted with a -hexadecenyl succinic anhydride to give the 2-[p-(a -hexadecenylsuccinylamido) phenyl]-5 - pyrazolone. By reacting this with the diazonium sulphate from dichloroaniline, 2-[p-(a -hexadecenylsuccinylamido) phenyl] - 3 - methyl - 4 - dichlorophenylazo - 5-pyrazolone is obtained. Similarly, 1-phenyl-2-methyl - 3 - p - nitrophenyl - 5 - pyrazolone is reduced with hydrogen and nickel and reacted with a -hexadecenyl succinic anhydride to give 1- phenyl - 2 - methyl - 3 - [p - (a - hexadecenyl - succinylamido) phenyl] - 5 - pyrazolone; and 1 - p - nitrophenyl-2-methyl-3-pentadecyl-5-pyrazolone is similarly reduced and treated with b -carbomethoxy-propionyl chloride to give 1-[p-(b -carbomethoxy-propionylamino) phenyl]-2-methyl-3-pentadeceyl-5-pyrazolone. 1 - Phenyl - 2 - methyl - 3 - pentadecyl - 4 - carbethoxyamino-5-pyrazolone is prepared by reacting the 4-amino derivative with chloroformic acid ethyl ester. 1- p - nitrophenyl - 3 - pentadecyl - 5 - pyrazolone is prepared by refluxing p-nitrophenyl hydrazine with palmitoyl acetic acid methyl ester in iso propanol. 1 - Phenyl - 3 - pentadecyl - 4 - phenylazo - 5 - pyrazolone is prepared from 1-phenyl-3-pentadecyl-5-pyrazolone and a diazinium salt of aniline. 1 - Phenyl - 2 - (a - sulphopropyl) - 3 - penta - decyl-4-amino-5-pyrozolone is prepared by treating 1 - phenyl - 3 - pentadecyl - 4 - diacetylamino - 5 - pyrazolone with n-propane sultone and then hydrolysing the acetyl groups.
GB3960856A 1956-12-31 1956-12-31 Improvements in or relating to the production of coloured photographic images Expired GB880862A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE563474D BE563474A (en) 1956-12-31 1957-12-24
US705508A US3012884A (en) 1956-12-31 1957-12-27 Production of colored photographic images
FR1207422D FR1207422A (en) 1956-12-31 1957-12-30 Process for the production of color photographic images
DEG23643A DE1063900B (en) 1956-12-31 1957-12-31 Process for the preparation of color masked photographic color images by color development
US70914A US3013879A (en) 1956-12-31 1960-11-22 Production of color photographic images
GB23203/61A GB975930A (en) 1956-12-31 1961-06-27 Improvements in or relating to the production of coloured photographic images
FR874185A FR81106E (en) 1956-12-31 1961-09-26

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
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
GB880862A true GB880862A (en) 1961-10-25

Family

ID=7124049

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3960856A Expired GB880862A (en) 1956-12-31 1956-12-31 Improvements in or relating to the production of coloured photographic images

Country Status (2)

Country Link
DE (1) DE1119666B (en)
GB (1) GB880862A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113058529A (en) * 2021-03-30 2021-07-02 河北冀衡药业股份有限公司 Continuous preparation method of 4-nitrosoantipyrine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1282458B (en) * 1964-10-03 1968-11-07 Wolfen Filmfab Veb Process for producing color corrected color photographic images

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113058529A (en) * 2021-03-30 2021-07-02 河北冀衡药业股份有限公司 Continuous preparation method of 4-nitrosoantipyrine
CN113058529B (en) * 2021-03-30 2023-01-31 河北冀衡药业股份有限公司 Continuous preparation method of 4-nitrosoantipyrine

Also Published As

Publication number Publication date
DE1119666B (en) 1961-12-14

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