US3615606A - Colorphotographic material - Google Patents

Colorphotographic material Download PDF

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Publication number
US3615606A
US3615606A US741880A US3615606DA US3615606A US 3615606 A US3615606 A US 3615606A US 741880 A US741880 A US 741880A US 3615606D A US3615606D A US 3615606DA US 3615606 A US3615606 A US 3615606A
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US
United States
Prior art keywords
light
photographic material
alkyl
sensitive photographic
radical
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 - Lifetime
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US741880A
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English (en)
Inventor
Walter Schulte
Helmut Mader
Willibald Pelz
Fritz Nittel
Erich Reckziegel
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Agfa Gevaert AG
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Agfa Gevaert AG
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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

Definitions

  • R represents an alkoxy radical, an alkylthio radical, a secondary or tertiary alkylamino group, a halogen, an alkyl radical, arylthio;
  • R represents a substituent in the 4- or 5-position, which is: sulfonamide, carbamoyl, acylamino, an alkylsulfonyl;
  • R represents hydrogen, an alkyl or alkoxy radical, halogen, sulfonamide or carbamoyl alkyl or alkylsulfonyl.
  • the resulting dye should, as far as possible, absorb only the desired spectral region since every side absorption in other spectral regions is disadvantageous. Furthermore, the resulting dyes should be light stable and stable even under the extreme conditions such as relatively high temperature and atmospheric moisture, found in the tropics.
  • the color couplers themselves which are incorporated in the light-sensitive layer should, also, of course possess sufficient stability under tropical conditions. The yellow couplers hitherto known do not meet requirements in practice in particular with regard to the last mentioned property. Furthermore, for economical reasons, only those color couplers which can be prepared by a simple method are of interest.
  • An object of this invention is to provide couplers which, are stable under tropical conditions and to light, and which can be produced in high yields and in pure form.
  • compounds of benzoyl acetanilide type of the following formula are especially suitable for use as yellow couplers in photographic silver halide emulsion layers:
  • R2 A-NH-C ooH,-o o O-R1 l L 5 6 soar in which R represents an alkyl radical preferably containing one to 18 carbon atoms;
  • R represents 1. an alkoxy radical preferably containing up to 18 carbon atoms
  • alkylthio radical preferably containing up to 18 carbon atoms
  • a secondary or tertiary alkylamino group preferably containing up to 18 carbon atoms or a preferably saturated fiveor six-membered nitrogen-containing heterocyclic ring such as pyrrolidine or piperidine linked to the benzene nucleus through the nitrogen atom;
  • halogen atom such as chlorine or bromine or an alkyl radical
  • the alkyl groups of the above substituents may contain further substituents, e.g. halogen atoms, to form in particular, a trifluoromethyl group, or phenyl radicals;
  • Arylthio preferably phenylthio particularly alkyl substituted phenyl, halogensubstituted phenyl;
  • Aroxy preferably phenoxy particularly alkyl substituted phenyl, halogen substituted phenyl 8.
  • Aralkoxy preferably benzyloxy or substituted benzyloxy such as halogen substituted or alkyl sub stituted benzyloxy;
  • R represents a substituent in the fouror five-position
  • carbamoyl in which the amide group may be substituted by alkyl radicals which have preferably one to 18 carbon atoms;
  • R represents hydrogen, an alkyl or alkoxy radical preferably containing up to five carbon atoms, halogen such as chlorine or bromine, sulfonamide or carbamoyl in which the amide groups may be substituted by alkyl radicals which preferably contain up to 18 carbon atoms or alkylsulfonyl, preferably containing up to l8 carbon atoms.
  • the benzene rings especially the benzene ring present in the amide part of the color coupler molecule, may contain any other substituents in addition to those already mentioned, e.g., alkyl or alkoxy groups, or halogen atoms.
  • 3-Amino-4-methoxybenzenesulfonic acid-N-stearyl amide 130 g. of the above nitro compound are hydrogenated in 1,600 ml. of methanol at '50 atmospheres and 50 C. with Raney nickel. The product is filtered while hot and cooled to C. The precipitated amine is suction filtered, washed with methanol and dried in air. Yield: 100 g., m.p. 89 C.
  • REDUCTION 180 g. of the above compound in 2 l. of ethanol are hydrogenated in the presence of Raney nickel at 50 C. and 50 atmospheres pressure.
  • the catalyst is removed by filtration under suction, the solution is cooled to 0 C. and the precipitated product is suction filtered and washed with ethanol.
  • a mixture of 33 g. or 4-methoxybenzoyl acetic acid ethyl ester and 200 ml. of chlorobenzene are added dropwise to a solution of 56 g. of the above product and 30 ml. of triethylamine in 300 ml. of chlorobenzene at C.
  • the reactions mixture is then heated for 4 hours at 140 C. with stirring, during which time a small amount of chlorobenzene and alcohol distil off.
  • the mixture is then concentrated by evaporation under vacuum and the residue is recrystallized from ethanol.
  • the other couplers may be prepared in analogous manner.
  • the color couplers to be used in accordance with the present invention are incorporated in the silver halide emulsion by known methods. They are preferably added before casting in the form of a solution, e.g. in the form of a solution, e.g. in the form of a solution of their alkali metal salts, to the blue-sensitive silver halide emulsion.
  • solutions of the color couplers which are hydrophobic may be emulsified if desired in the presence of so-called oil formers, in gelatin, after which the resulting emulsion is dried, and allowed to swell again in water and is then mixed with the silver halide gelatin emulsion.
  • Other processes are known according to which the solution of the color coupler in an organic solvent is mixed directly with the silver halide emulsion, and the silvent is evaporated off.
  • the color couplers according to the invention may be used in any of these processes.
  • the binders which may be used for the layers are the known hydrophilic film-forming agents such as proteins, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxyalkyl-cellulose, especially carboxamethylcellulose, derivatives of alginic acid and their alkali metal salts or esters.
  • hydrophilic film-forming agents such as proteins, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxyalkyl-cellulose, especially carboxamethylcellulose, derivatives of alginic acid and their alkali metal salts or esters.
  • the layers may in addition be stabilized by known additives, in particular the azaindene derivatives described in the publication by Birr in Z. wiss. Phot. 47 [952), pages 2-28.
  • the layer support is transparent or opaque depending on the purpose for which the light-sensitive material is to be used and maybe made of paper, glass, cellulose esters such as cellulose nitrate or cellulose triacetate, polyesters, polystyrene or other high molecular weight natural or synthetic materials.
  • the yellow couplers according to the invention are usually incorporated with the light-sensitive layer itself.
  • they may also be added to a layer which is not light sensitive and which is in contact with the blue-sensitized layer, or with a layer of colloid which is separated from the blue-sensitized layer by a water-permeable layer of colloid.
  • the yellow couplers of the present invention can be applied for colorphotographic materials to be used for a negative-positive process as well as for a colorphotographic reversal process.
  • Any color-forming developers which contain a primary amino group may be used for the development step.
  • Those of the p-phenylenediamine type e.g. N,N-diethyl-p-phenylenediamine, monomethyl-p-phenylenediamine, N,N'- dimethyl-p-phenylenediamine, Z-amino-S- diethylaminotoluene and N-butyl-Nw-sulfobutyl-p-phenylenediamine are preferred.
  • EXAMPLE 1 4 mols of coupler 8 are dissolved in water containing a small amount of alcohol and sodium hydroxide solution. The total volume of the solution is about 100 ml. and the pH should range between 7 and 9.
  • the coupler solution prepared in this way is added to 50 ml. of a photographic silver bromide gelatine emulsion which contains 7 percent of gelatin and 0.5 mol of silver bromide per kg. of emulsion. ml. of 7.5 percent gelatin solution, 5 ml.
  • the fixing bath consists of a solution of 200 g. of sodium thiosulfate in 1 1. ofwaten 7.
  • Light-sensitive photographic material as defined in claim The processing times after development are as follows: 3 in which the color coupler has the 8 formula: 15 minutes washing 5 minutes bleaching bath v "Has 5 minutes washing 5 minutes fixing bath NH C CHT C O 0H, 10 minutes washing. I I] I] A yellow image of the step wedge is obtained. 0 0 g 11 If the yellow image is exposed to 96 percent relative humidity for one day at 60 C., no reduction is found at a density of I 0.5 and 1.5.
  • Light-sensitive photographic material comprising at least I one silver halide emulsion layer which contains a yellow cou- CH3 pler of the following formula:

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Photoreceptors In Electrophotography (AREA)
US741880A 1967-07-10 1968-07-02 Colorphotographic material Expired - Lifetime US3615606A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA0056235 1967-07-10

Publications (1)

Publication Number Publication Date
US3615606A true US3615606A (en) 1971-10-26

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Country Status (6)

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US (1) US3615606A (en:Method)
BE (1) BE717841A (en:Method)
CH (1) CH496969A (en:Method)
FR (1) FR1573578A (en:Method)
GB (1) GB1248924A (en:Method)
NL (1) NL6809746A (en:Method)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001083434A3 (en) * 2000-04-28 2002-03-28 Hoffmann La Roche P-(sulfonyl)-aryl and heteroaryls amines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001083434A3 (en) * 2000-04-28 2002-03-28 Hoffmann La Roche P-(sulfonyl)-aryl and heteroaryls amines
US7071177B2 (en) 2000-04-28 2006-07-04 Syntex (U.S.A.) Llc P-(sulfonyl) aryl and heteroarylamines as anti-inflammatory agents
US20060173075A1 (en) * 2000-04-28 2006-08-03 Krauss Nancy E P-(sulfonyl) aryl and heteroarylamines-as anti-inflammatory agents
CN100374416C (zh) * 2000-04-28 2008-03-12 霍夫曼-拉罗奇有限公司 对(磺酰基)芳基和杂芳基类化合物

Also Published As

Publication number Publication date
DE1597464B2 (de) 1975-09-25
GB1248924A (en) 1971-10-06
FR1573578A (en:Method) 1969-07-04
NL6809746A (en:Method) 1968-12-27
DE1597464A1 (de) 1970-05-14
CH496969A (de) 1970-09-30
BE717841A (en:Method) 1969-01-10

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