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
  • G03C7/362—Benzoyl-acetanilide couplers
• • 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

Definitions

• a colored compound thus formed is deposited adjacent to the silver grains of the silverimage during the development.
• a colored image may be formed by adding to certain developer solutions or by incorporating in the gelatino-silver-halideemulsion before or after exposure a compound which couples during development with the oxidation productof the developing agent and forms a coloring substance which is likewise-deposited adjacent to the silver grains of the silver image during deve1opment.
• a compound, which is employed in conjunction with a developins'agent for the silver and which couples with the oxidag component or The present invention concerns newer im-.- proved color forming developers comprising a primary aromatic compound, serving as the developing ageniuand a coupler as herein:
• the aromatic amino developing agents used with the coupler compounds of our invention include the mono-, di and tri-amlnoaryl compounds and their derivatives formed by substitue tion in the amino group as well as in the ring, such as alkylphenylenediamines and alkyltoluylenediamines. These compounds are usually used in the salt form, such as the hydrochloride or the sulphate, which are more stable than the amines themselves. Suitable compounds are diethyL-p-phenylenediamine hydrochloride, monomethyl-p-phenylenediaminehydrochloride, dimethyl-p-pheny1enediaminehydrochloride and dimethyl-p-phenylenediamine sulphate.
• the aromatic amino developing agents used with the coupler compounds of our invention include the mono-, di and tri-amlnoaryl compounds and their derivatives formed by substitue tion in the amino group as well as in the ring, such as alkylphenylenediamines and alkylto
• p-aminophenols and their substitution products may also be used where the amino group is unsubstituted. All of these compounds have an unsubstituted amino group which enables the oxidation products of the developer to couple NHC O CHaC O op-00H" din 2,4-diamylphenyl p (benzoylaoetamino)-benzsnesulphonate with the color forming compounds to form a dye image.
• the coupler must contain a coupling function, which in this case is a reactive methylene group.
• coupling function we mean a functionor.al or reactive group common to coupler compounds which-react with primary aromatic amino developing agents.
• reactive methylene we v mean a CH2 group which is reactive in the coupling process.
• the CH2 group is usually present between two ne ative centers as in the groups -COCH2--CO or -CO-CH2CN, in the case of the present
• One of the hydrogen atoms of the methylenegroup may, in general, be substituted without destroying the chemical activity of the group.
• the coupling compounds used according to our invention may contain other substituents which do not affect the coupling properties of the compound.
• the general formula parent medium such as glass, a cellulose ester, or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
• the emulsion may be coated as a single layer on the support or as superposed layers on one or both sides of the support.
• the superposed layers may be differentially sensitized to form natural color photographic images in the well known manner.
• the couplers which we propose to, use are pre- I pared, in general, by the interaction of the sulphonyl chloride of the coupler with the appropriate alcohol in the presence of one equivalent of pyridine.
• a p-(benzoylacetamino) -ben zenesulphonate one equivalent weight of p-(benzoylacetamino)- benzene-sulphonyl chloride is reacted with an excess methyl alcohol in the presence of one equivalent weight of pyridine.
• the sulphonyl chloride is reacted with the sodium salt of the phenol in xylene solution.
• the coupler was obtained by the reaction of p-(benzoylacetamino)- benzene sulphonyl chloride on the sodium salt of 2,4-diamylphenol in xylene solution.
• the sulphonyl chlorides of thecouplers are prepared as described in our copending applica- I tion Serial No. 358.494, filed September 26, 1940, by treating the appropriate acetanilide with chlorosulphonic acid at' a temperature below about 10 C. and permittingthe reaction to proceed fora, short time, that is, of the order of a few days.
• p-benzoylacetamino benzenesulphonyl chloride is prepared as follows:
• ExAmrLn- -p-Benzoylacetaminobeneenesulphonyl chloride One part of benzoylacetanilide is added to 2 volumes ofchlorosulphonic acid while keeping the temperature below 10 C. Thereaction mixture is allowed to warm slowly to room temperature, and, after standing overnight, is decomposed by pouring onto ice. The product. is filtered, washed with water, dried in ether solution, and recrystallized 149-151" C.
• a color forming photographic develope comprising a primary aromatic amino developing agent formula R-SOe-O-Y where R is an aroyl acetaminobenzene and Y is selected from the group consisting of alkyl,
• alkyl is selected from the; group consisting of alkyl, aryl, alkoxyalkyl and aryloxyalkyl radicals.
• R is a p-benzoyl acetamino benzene and Yis selected from the group consisting of alkyl
• R is a p-benzoylacetaminobenzene and Y is an alkyl radical.
• a color forming photographic developer comprising a primary aromatic aminodeveloping agent and a coupler compound having the formula; V
• R SOr--O--Y where R is a p-benzoylacetaminobenzene and Y i is an alkoxyethyl radical.
• a color forming photographic developer 8 The method ofproducing a colored photo graphic image in a gelatino silver halide emulsion layer which comprises exposing the layer and developing it with a primary aromatic amino developing agent in the presence of a coupler compound having the formula:
• sion layer which comprises exposing the layer and developing it with a primary aromatic amino developing agent in the presence of I a coupler compound having the formula:
• R is a p-benzoylacetaminobenzene and Y -is an alkoxyethyl radical.
• O 0 ocmcoNHGsor-d-Y where Y is selected from the group consisting of alkyl, aryl, valkoxyalkyl, and aryloxyalkyl radicals.
• a photographic emulsion for forming colored images comprising acarrier containing a sensitive silver halide and a having the formula:
• coupler compound I where- R. is an aroyl acetaminobenzene andY is selected from the group consisting of alkyl, aryl, alkexyaikyl and aryloxyalkyl radicals.
• a photographic emulsion for forming colored images comprising a gelatino silver halide emulsion having incorporated therein a coupler compound of the general formula:
• R is a p-benzoylacetaminobenzene and Y 'is selected from the group consisting of alkyl,
• a photographic emulsion for forming col-' ored images comprising'a gelatino silver halide emulsion having incorporated therein a coupler compound of the general formula:
• a photographic emulsion for forming colored images comprising a gelatino silver halide emulsion having incorporated therein a coupler compound of the general formula:
• R is a p-benzoylacetami'nobenzene and Y where Y is selected from the. group consisting of is an alkoxyethyl radical. alkyl, aryl, alkoxyalkyl, and aryloxyalkyl rad- 15.
• a photographic emulsion for forming oolicals. ored images comprising a gelatino silver halide HENRY DUDLEY PORTER.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (1)

Publications (1)

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ID=32095157

Family Applications (1)

Country Status (3)

Cited By (4)

Families Citing this family (1)

• 1940
  • 1940-01-03 GB GB183/40A patent/GB537921A/en not_active Expired
  • 1940-09-26 US US358493A patent/US2289805A/en not_active Expired - Lifetime
• 1945
  • 1945-08-02 FR FR928785D patent/FR928785A/fr not_active Expired

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