Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07K—PEPTIDES
  • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
  • C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
  • C07D277/38—Nitrogen atoms
  • C07D277/44—Acylated amino or imino radicals
  • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
  • C07D277/54—Nitrogen and either oxygen or sulfur atoms
• • 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
  • G03C7/362—Benzoyl-acetanilide couplers

Definitions

• the color couplers needed for this purpose are preferably incorporated in the photographic emulsion layers or in colloid layers located in the vicinity thereof.
• a substituent such as a chain of several carbon atoms.
• substituents which render the coupler water-soluble are usually introduced. Sulpho groups in particular are efiective in this respect.
• acylacetarylides As couplers for yellow, the acylacetarylides have been used in practice. As acylacetarylides sulphonated in their arylide part, only the acetyl acetarylides have been obtained by allowing diketene to react with sulphonated aniline derivatives. Corresponding sulphonated aroylacetarylides have not been obtained, due to the lack of a suitable method.
• An object of the present invention is a method for preparing aroyl-acetarylides sulphonated in the arylide part.
• a further object is a class of new sulphonated aroyl-acetarylides.
• Another object is a process for the production of a colored photographic image by the use of these aroyl-acetarylides.
• Still a further object is a light-sensitive photographic material containing such aroylacetarylides.
• a reducible silver salt image is developed with a primary amino aromatic developing agent in the presence of an aroyl-acetarylide sulphonated in its arylide part wherein the hydrogen atoms of the metehylene group may be replaced by substituents which readily split oil on color development.
• such compounds are prepared by condensing an aroylacetic ester with a compound of the formula NH -aryl-SO F, and by hydrolyzing the rsulting sulphofluoride into the corresponding sulphonic acid or ester.
• the aryl group of the ester or of the sulphofluoride may contain a group able to render the coupler fast to difiusion.
• the aryl group of the ester may contain a nitro group which after condensation may be reduced to an amino group, wherein a group rendering fast to diffusion may be introduced Without difliculty.
• Aromatic compounds may be treated with fluorosulphonic acid.
• Steinkopf I. prakt. Chem. (2) 117 (1927) 1-82
• Steinkopf has nitrated two sulphofluorides, obtained in this way, into m-Nitro-benzene sulphofluoride, and p-Methyl-m-nitro-benzene sulphofiuon'de.
• nitro-sulphofluorides have been converted into the corresponding amino compounds by reducing a 25% alcoholic solution of the nitro-sulphofluoride by means of Raney nickel at 40-400 C. and under a hydrogen pressure of 10-100 atm. After elimination of the Raney nickel, the filtrate is either distilled or evaporated until the amine crystallizes. In this way we have prepared.
• Potassium fluoride may also be allowed to react with acetyl-amino arylene sulphochlorides.
• the resulting acetylamino-arylene-sulphofiuorides may be de-acylated by means of HCl in alcohol. In this way we have prepared:
• CH CH (CH COCl (myristoyl-chloride), p-myristoyl-amino-m-nitro-benzenesulphofluoride, M.P. 64 C. (from acetonitrile), is obtained. Reducing the latter with Raney nickel in dioxane at 40-50 C. and under a hydrogen pressure ofi 10-50 atm., eliminating the nickel and evaporating the filtrate until the product crystallizes by cooling, yields p-myristoyl-amino-m-amino-benzene-sulphofluoride, M.P. 122 C.
• Condensation of these sulphofluorides with beta-keto esters may be done in the usual way by refluxing the two compounds in toluene or xylene, evaporating the latter after condensation, and recrystallizing the product.
• the sulphofluorides In order to convert the sulphofluorides into the correspending sulphonic acids, they are first dissolved in acetone or aqueous dioxane and treated at 60 C. with an aqueous solution of sodium hydroxide. After cooling, the sodium salt of the coupler crystallizes out, or is precipitated by the addition of salt. These sodium salts are recrystallized and may easily be. dissolved in water or in a mixture of water and alcohol for addition to a silver halide emulsion or to a colloid which will form a layer adjacent to a silver halide emulsion layer or separated therefrom by a water-permeable colloid layer.
• primary aromatic amino developing agents may be used mono-, diand tri-amino compounds; as monoamino developers may be mentioned amino phenols and amino cresols, their halogen derivatives, and also amino naphthols.
• R represents an aryl radical selected from the group consisting of alkoxyphenyl, alkoXy naphthyl, dialkoxy phenyl, dichloro alkoxy phenyl, isooctyl phenoxy ethoxy phenyl, nitrophenyl, and acylamino phenyl
• R" represents a monocyclic arylene radical of the.
• benzene series selected from the group consisting of phenylene, chlorophenylene, dialkyl amino phenylene, alkyl phenylene, alkoxy phenylene, dialkoxyphenylene, and acylaminophenylene, and Me represents an alkali metal atom, comprising condensing an 'aroyl acetic ester of the following formula:
• R represents a lower alkyl group, with a compound of the formula H N-R'SO F, and hydrolyzing V the resulting compound in the presence of an alkali metal hydroxide.
• R represents an aryl radical selected from the group consisting of alkoxyphenyl, alkoXy naphthyl, dialkoxy phenyl, dichloro alkoxy phenyl, isooctyl phenoxy ethoxy phenyl, nitrophenyl, and acylamino phenyl
• R represents a monocyclic arylene radical of the benzene series, selected from the group consisting of phenylene, chlorophenylene, dialkyl amino phenylene, alkyl phenylene, alkoxy phenylene, dialkoxyphenylene, and acylaminophenylene
• Me represents an alkali metal atom, said sulphonated aroyl acetarylide being prepared by condensing an aroyl acetic ester of the following formula:
• RCO'CH -COOR wherein R" represents a lower alkyl group, with a compound of the formula H NR'-SO F, and hydrolyzing the resulting compound in the presence of an alkali metal hydroxide.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• General Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Biochemistry (AREA)
• Biophysics (AREA)
• Health & Medical Sciences (AREA)
• Genetics & Genomics (AREA)
• Medicinal Chemistry (AREA)
• Molecular Biology (AREA)
• Proteomics, Peptides & Aminoacids (AREA)
• Analytical Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (5)

• 0
  • BE BE546753D patent/BE546753A/xx unknown
• 1955
  • 1955-04-05 GB GB9900/55A patent/GB808276A/en not_active Expired
• 1956
  • 1956-04-03 US US575718A patent/US2950314A/en not_active Expired - Lifetime
  • 1956-04-05 FR FR1145045D patent/FR1145045A/fr not_active Expired
• 1963
  • 1963-10-24 US US318487A patent/US3287381A/en not_active Expired - Lifetime

Patent Citations (5)

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