GB990627A - Method of preparing non-migratory colour couplers for yellow - Google Patents

Method of preparing non-migratory colour couplers for yellow

Info

Publication number
GB990627A
GB990627A GB16622/61A GB1662261A GB990627A GB 990627 A GB990627 A GB 990627A GB 16622/61 A GB16622/61 A GB 16622/61A GB 1662261 A GB1662261 A GB 1662261A GB 990627 A GB990627 A GB 990627A
Authority
GB
United Kingdom
Prior art keywords
acetanilide
fluorosulphonyl
cetylmercapto
yield
saponified
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
GB16622/61A
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
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Publication of GB990627A publication Critical patent/GB990627A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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

Compounds of the formula R-CO-CH2-CO-NH-Ar(SO3Me)ZD wherein R is a methyl radical, an aryl or substituted aryl radical, or a heterocyclic radical, Ar is a nucleus of the benzene series, Me is hydrogen, an alkali metal or ammonium, Z is oxygen, sulphur, a sulphonyl group or an >N(alkyl) group, and D is an aliphatic radical of 5-20 carbon atoms, are prepared by condensing diketene or a compound of the formula R1-CO-CH2-CO-OR2 where R1 is an aryl or substituted aryl ardical or a heterocyclic radical and R2 is a lower alkyl radical, with an amine of the formula H2NAr(SO2F)ZD wherein Ar, Z and D are as above; the sulphofluoride group in the products may then be saponified. In the examples: (1) 2-cetylmercapto - 5 - fluorosulphonylaniline (c.f. Specification 983,648) and a -furoylacetic acid ethyl ester yield a -furoyl-(2-cetylmercapto-5-fluorosulphonyl) - acetanilide, which may be saponified to yield a - furoyl - (2 - cetylmercapto - 5-sulpho) - acetanilide (2) 2 - cetylsulphonyl - 5-fluorosulphonyl - aniline (cf. German Specification 1,109,522) and a - furoylacetic acid ethyl ester yield a -furoyl-(2-cetylsulphonyl-5-fluorosulphonyl) - acetanilide, which may be saponified to yield a -furoyl-(2-cetylsulphonyl-5 - sulpho) - acetanilide; (3) 3 - fluorosulphonyl - 4 - cetylmercaptoanilino (cf. Specification 983,648) and isonicotinoylacetic acid ethyl ester yield isonicotinoyl - (3 - fluorosulphonyl - 4 - cetylmercapto) - acetanilide, which may be saponified to yield isonicotinoyl-(3-sulpho - 4 - cetylmercapto) - acetanilide; (4) 2-cetylmercapto - 5 - fluorosulphonyl - aniline and p-methoxybenzoylacetic acid ethyl ester yield p - methoxybenzoyl - (2 - cetylmercapto - 5-fluorosulphonyl) - acetanilide, which may be saponified to yield p-methoxybenzoyl-(2-cetylmercapto - 5 - sulpho) - acetanilide; (5) 2-cetylmercapto - 5 - fluorosulphonyl - aniline and benzoylacetic acid ethyl ester yield benzoyl-(2 - cetylmercapto - 5 - fluorosulphonyl)-acetanilide, which may be saponified to yield benzoyl - (2 - cetylmercapto - 5 - sulpho) - acetanilide; (6) 2 - cetylsulphonyl - 5 - fluorosulphonyl - aniline and diketene yield acetyl - (2-cetylsulphonyl - 5 - fluorosulphonyl) - acetanilide, which may be saponified to yield acetyl-(2 - cetylsulphonyl - 5 - sulpho) - acetanilide; (7) 2 - cetylsulphonyl - 5 - fluorosulphonylaniline and benzoylacetic acid ethyl ester yield benzoyl - (2 - cetylsulphonyl - 5 - fluorosulphonyl)-acetanilide, which may be saponified to yield benzoyl - (2 - cetylsulphonyl - 5-sulpho) - acetanilide; (8) 2 - cetyloxy - 5-fluorosulphonyl - aniline (cf. Specification 983,648) and benzoylacetic acid ethyl ester yield benzoyl - (2 - cetyloxy - 5 - fluorosulphonyl)-acetanilide, which may be saponified to yield benzoyl - (2 - cetyloxy - 5 - sulpho)-acetanilide; (9) 2 - (N - methylcetyl) amino-5 - fluorosulphonyl - aniline (cf. Belgian Specification 590,934) and benzoylacetic acid ethyl ester yield benzoyl-[2-(N-methylcetyl) amino - 5 - fluorosulphonyl] - acetanilide, which may be saponified to yield benzoyl-[2-(N - methylcetyl) amino - 5 - sulpho] - acetanilide; (10) 3 - fluorosulphonyl - 4 - cetylmercaptoaniline and benzoylacetic acid ethyl ester yield 3-fluorosulphonyl-4-cetylmercapto-acetanilide, which may be saponified to yield benzoyl - (3 - sulpho - 4 - cetylmercapto) - acetanilide; (11) 2 - cetylmercapto - 5 - fluorosulphonyl - aniline and a - thienoylacetic acid ethyl ester yield a -thienoyl-(2-cetylmercapto-5-fluorosulphonyl)-acetanilide, which may be saponified to a -thienoyl-(2-cetylmercapto-5-sulpho) - acetanilide; (12) 2 - cetylmercapto - 5-fluorosulphonylaniline and mesitoylacetic acid ethyl ester yield mesitoyl - (2 - cetylmercapto-5 - fluorosulphonyl) - acetanilide, which may be saponified to yield mesitoyl-(2-cetylmercapto - 5 - sulpho) - acetanilide. The saponified products are useful in colour photography as non-migratory couplers for yellow. Specification 808,276 also is referred to.
GB16622/61A 1960-05-19 1961-05-08 Method of preparing non-migratory colour couplers for yellow Expired GB990627A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEG29711A DE1126400B (en) 1960-05-19 1960-05-19 Process for the preparation of yellow dye formers

Publications (1)

Publication Number Publication Date
GB990627A true GB990627A (en) 1965-04-28

Family

ID=7123807

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16622/61A Expired GB990627A (en) 1960-05-19 1961-05-08 Method of preparing non-migratory colour couplers for yellow

Country Status (4)

Country Link
US (1) US3138604A (en)
BE (1) BE603995A (en)
DE (1) DE1126400B (en)
GB (1) GB990627A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9513108D0 (en) * 1995-06-28 1995-08-30 Kodak Ltd Image-dye-forming couplers and photographic elements containing them

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2714117A (en) * 1955-07-26 Production of acetoacetic acid amides

Also Published As

Publication number Publication date
US3138604A (en) 1964-06-23
DE1126400B (en) 1962-03-29
BE603995A (en) 1961-09-18

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