US3645742A - Color photography - Google Patents

Color photography Download PDF

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Publication number
US3645742A
US3645742A US779627A US3645742DA US3645742A US 3645742 A US3645742 A US 3645742A US 779627 A US779627 A US 779627A US 3645742D A US3645742D A US 3645742DA US 3645742 A US3645742 A US 3645742A
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United States
Prior art keywords
group
color
light
silver halide
thiazole
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Expired - Lifetime
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US779627A
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Inventor
Marcel Hendrik Verbrugghe
Arthur Henri De Cat
Marcel Karel Van Doorselaer
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Agfa Gevaert NV
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Agfa Gevaert NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • C07D277/40—Unsubstituted amino or imino radicals
    • 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen 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

Definitions

  • a light-sensitive photographic color material containing a red-sensitized, a green-sensitized and a blue-sensitive silver halide emulsion layer wherein on color development, by use of appropriate color couplers, a cyan, magenta and yellow dyestuff image are formed respectively.
  • novel photographic coupler compounds of the benzoylacetamide type yielding yellow dyes upon coupling with the oxidized aromatic primary amino developing agent are provided corresponding to the following general formula:
  • X represents a hydrogen atom or a group which splits off on color development, e.g., a halogen 'atom, an S-R group wherein R is alkyl including substituted alkyl, aryl including substituted aryl, etc.
  • D represents a residue rendering the molecule fast to diffusion e.g., an acyclic aliphatic hydrocarbon residue with from five to 20 carbon atoms,
  • R 1 stands for hydrogen, alkyl such as methyl, alkoxy such as methoxy, decyloxy, halogen such as chlorine, dialkylamino such as dimethylamino or sulphamoyl such as diethylsulphamoyl, and
  • Z represents the atoms necessary to close a nucleus of the thiazole series such a thiazole, 4-methyl-thiazole, 4- tert.butyl thiazole, 4-benzyltiazole, 4-phenylthiazole, 5-
  • phenylthiazole 4-( p-methoxyphenyU-thiazole, 4-(pchlorophenyl )-thiazole, 4-phenyl-5-fluorosulphonylthiazole, 4-methyl-5-sulphothiazole, 4-(m-
  • these yellow color formers also have a high coupling activity, i.e., they furnish dye images with high color density, irrespective of the presence of the displaceable group.
  • the preparation of the yellow-forming color couplers corresponding to the above general formula can be represented by the following reaction scheme CHgClg lCOCHa COOHCOOR -oo-cmcoon NaO CH CHaOH wherein R R R and D have the same significance as above and R represents a lower alkyl group such as methyl and ethyl.
  • Benzoylacetamide color couplers falling within the ambit of the above general formula I are illustrated as follows HC o-Nncoomco- CHO 1o 33
  • the following preparation of some specific compounds corresponding to the above general formula illustrate in detail how the yellow color formers can be prepared.
  • This compound was prepared in an analogous way as described in preparation In. starting from 0.5 mole of o-hexadecyloxybenzoic acid which in its turn was prepared according to the method of Stanton et a]. in JACS 64 (1942) 1,961.
  • the o-hexadecyloxybenzoyl-acetic acid methyl ester formed has a melting point of 53-54 C.
  • This compound was prepared in an analogous way as the compound described in preparation 1 starting from 0.1 mole o-hexadecyloxybenzoyl-acetic acid methyl ester (see preparation and 0.1 of 2-amino-4-(m-fluorosulphonyl-phenyl)- thiazole prepared as described below. A white crystalline product having a melting point of 108 C. was obtained.
  • m-fluorosulphonyl-benzoyl chloride was converted to the corresponding acetophenone, essentially according to the procedure developed by Long and Troutman, JACS, 71, 2,473 (1949) for the synthesis of p-nitroacetophenone.
  • the crude product obtained after hydrolysis of diethyl-mfluorosulphonyl benzoyl malonate was washed with a saturated solution of sodium bicarbonate to remove about 5 percent of m-fluorosulphonyl-benzoic acid formed during hydrolysis.
  • From 52.5 g. (0.24 moles) of m-fluorosulphonyl-benzoyl chloride were obtained after recrystallization from about 350 ml. of methanol, 36.8 g. (76 percent) of m-fluorosulphonylacetophenone with melting point 92 C. c. m-fluorosulphonyl-phenacyl bromide.
  • the yellow color formers according to the present invention are of the nondiifusible type, i. e., theyv comprise in their molecule an organic radical sufiiciently large for preventing the color coupler of wandering from the colloid layer in which the coupler is incorporated to another colloid layer.
  • the nondiffusing color couplers for each color separation image are usually incorporated into the coating compositions of the differently sensitized silver halide emulsion layers.
  • the nondiffusing color couplers may also be added to the coating compositions of non-light-sensitive colloid layers which are in water-permeable relationship with the light-sensitive silver halide emulsion layers, e.g., in layers which are in direct contact with the light-sensitive layers or which are separated from said light-sensitive layers by waterpermeable non-light-sensitive layers.
  • the nonmigratory yellow-forming color couplers can be incorporated in the coating composition of the silver halide emulsion layers or other colloid layers in water-permeable relationship therewith according to any technique known by those skilled in the art for incorporating photographic ingredients, more particularly color couplers, into colloid compositions.
  • the watersoluble color couplers i.e., those containing one or more water-solubilizing groups such as sulpho or carboxyl groups (in acid or salt form) can be incorporated into the coating composition of the layer in question from an aqueous solution and the water-insoluble or insufiiciently water-soluble color couplers from a solution in the appropriate water-miscible or water-immiscible high-boiling or low-boiling organic solvents or mixtures thereof whereupon the solution obtained is dispersed, occasionally in the presence of a wetting or dispersing agent, in a hydrophilic colloid composition forming or forming part of the binding agent of the colloid layer.
  • water-solubilizing groups such as sulpho or carboxyl groups
  • the hydrophilic colloid composition may of course comprise in addition to the colloid carrier all other sorts of ingredients.
  • the water-insoluble color couplers carrying fluorosulphonyl groups or carboxylic acid ester groups such as ethoxycarbonyl groups can also be converted by alkaline hydrolysis in the corresponding sulphonic acids or carboxylic acids respectively which in their turn can be incorporated in hydrophilic colloid compositions in the form of their alkali salts from aqueous solutions.
  • the solution of said color coupler need not necessarily be dispersed or dissolved directly in the coating composition of the silver halide emulsion layer or other water-permeable layer.
  • Said solution may advantageously be first dispersed or dissolved in an aqueous non-light-sensitive hydrophilic colloid solution whereupon the resultant mixture, after the occasional removal of the organic solvents employed, is intimately mixed with the said coating composition of the light-sensitive silver halide emulsion layer or other water-permeable layer just before coating.
  • the couplers according to the invention may be used in conjunction with various kinds of photographic emulsions.
  • Various silver salts may be used as the sensitive salt such as silver bromide, silver iodide, silver chloride or mixed silver halides such as silver chlorobromide, silver bromoiodide and silver chlorobromoiodide.
  • the couplers can be used in emulsions of the mixed packet type as described in U.S. Pat. No. 2,698,794 of Leopold Godowsky, issued Jan. 4, 1955, or emulsions of the mixed grain type as described in U.S. Pat. No. 2,592,243 of Burt l-l. Carroll and Wesley T. Manson, Jr., issued Apr. 8, 1952.
  • the color couplers can be used with emulsions wherein latent images are formed predominantly on the surface of the silver halide crystal, or with emulsions wherein latent images are formed predominantly inside the silver halide crystal.
  • the hydrophiliccolloid used as the vehicle for the silver halide may be, for example, gelatin, colloidal albumin, zein, casein, a cellulose derivative, a synthetic hydrophilic colloid such as polyvinyl alcohol, poly-N-vinyl pyrrolidone, etc. If
  • compatible mixtures of two or more of these colloids may be employed for dispersing the silver halide.
  • the light-sensitive silver halide emulsions of use in the preparation of a photographic material according to the present invention may be chemically as well as optically sensitized. They may be chemically sensitized by effecting the ripening in the presence of small amounts of sulphur-containing compounds such as allyl thiocyanate, allyl thiourea, sodium thiosulphate, etc.
  • the emulsions may also be sensitized by means of reductors, for instance tin compounds as described in French Pat. No. 1,146,955 filed Apr. 1 l, 1956 by Gevaert Photo-Producten N.V. and in Belgian Pat. No.
  • the said emulsions may also comprise compounds which sensitize the emulsions by development acceleration, for example compounds of the polyoxyalkylene type such as alkylene oxide condensation products as described among others in U.S. Pat. No. 2,531,832 of William Alexander Stanton, issued Nov. 28, 1950, and 2,533,990 of Ralph Kingsley Blake, issued Dec. 12, 1950, in UK. Pat. Nos. 920,637 filed May 7, 1959, 940,051 filed Nov. 1, 1961, 945,340 filed Oct. 23, 1961, all by Gevaert Photo-Producten N.V. and 991,608 filed June 14, 1961 by Kodak and in Belgian Pat. No. 648,70 filed June 2, 1964 by Gevaert Photo-Production N.V. and onium derivatives of amino-N-oxides as described in UK. Pat. No. 1,121,696 filed Oct. 7, 1965 by Gevaert-Agfa N.V.
  • compounds of the polyoxyalkylene type such as alkylene oxide condensation products as
  • the emulsions may comprise stabilizers e.g., heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-Z-thione and l-phenyl-2-tetrazoline-5-thione and compounds of the hydroxytriazolopyrimidine type. They can also be stabilized with mercury compounds such as the mercury compounds described in Belgian Pat. Nos. 524,121 filed Nov. 7, 1953 by Kodak 677,337 filed Mar. 4, 1966 by Gevaert-Agfa N.V., 707,386 filed Dec. 1, 1967 by Gevaert- Agfa N.V. and in U.S. Pat. No. 3,179,520 of Yoshio Miura, Akasi Kumi and Yosuke Nadajima, issued Apr. 20, 1965.
  • stabilizers e.g., heterocyclic nitrogen-containing thioxo compounds such as benzothiazoline-Z-thione and l-phenyl-2-tetrazoline-5-thi
  • the light-sensitive emulsions may also comprise all other kinds of ingredients such as plasticizers, hardening agents, wetting agents, etc. Kodak, Kumai.
  • the nondifi'using yellow color formers described in the present invention are usually incorporated into a blue-sensitive silver halide emulsion.
  • this silver halide emulsion is coated as the topmost color-couplercontaining layer of a photographic multilayer color material.
  • Such photographic multilayer color material usually consists in the given sequence of a support, a red-sensitized silver halide emulsion layer with a cyan color former, a green-sensitized silver halide emulsion layer with a magenta color former and a blue-sensitive silver halide emulsion layer with a yellow color former.
  • a yellow filter layer generally comprising colloidal silver dispersed in gelatin, is provided usually between the blue-sensitive silver halide emulsion layer containing a yellow color former and the green-sensitized silver halide emulsion layer.
  • the emulsions can be coated on a wide variety of photographic emulsion supports.
  • Typical supports include cellulose ester film, polyvinylacetal film, polystyrene film, polyethylene terephthalate film and related films or resinous materials, as well as paper and glass.
  • an exposed silver halide emulsion layer is developed with an aromatic primary amino developing substance in the presence of a color coupler according to the present invention.
  • All color-developing agents capable of forming azomethine dyes can be utilized as developers.
  • Suitable developing agents are aromatic compounds such as pphenylene diamine and derivatives for example N,N-dialkyl-pphenylene diamines such as N,N-diethyl-p-phenylene, diamine, N,N-dialkyl-N'-sulphomethyl-p-phenylene diamines, and N,Ndialkyl-N'-carboxymethyl-p-phenylene diamines.
  • EXAMPLE 1 To a 300 g. of a blue-sensitive silver bromoidide emulsion (2.3 mole percent of iodide) comprising 23 g. of gelatin and an amount of silver halide equivalent to 20 g. of silver nitrate, is added 0.006 mole of color coupler no. 3 of the above list of color couplers. After neutralization and addition of the common additives such as stabilizers, wetting agents, and hardeners the necessary amount of distilled water to obtain 575 g. of emulsion is added whereupon the emulsion is coated on a cellulose triacetate support pro rats of 150 g. per sq.m. The emulsion layer is dried and overcoated with a gelatin antistress layer.
  • the material formed is exposed for 1/20 sec. Through a continuous wedge with constant 0.30 and then developed for 8 min. at 20 C. in a developing bath of the following composition:
  • N,N-diethyl-p-phenylene diamine 2.75 g.
  • the material is rinsed for 15 min. with water and treated in a bleach bath of the following composition:
  • a yellow-colored wedge image is obtained having an absorption maximum of 452 nm.
  • EXAMPLES 2-4 In three similar silver bromoiodide emulsions as described in Example 1 the color couplers no. 3 is replaced by 0.006 mole of color couplets no. 4, 5 and 7 respectively. After neutralization and addition of the usual ingredients the emulsions are coated, exposed through a continuous wedge and processed as described in example 1.
  • Yellow-colored wedge images are obtained having absorption maxima of 450 nm. 456 nm. and 456 nm. respectively.
  • EXAMPLE 5 400 g. of blue-sensitive silver homo-iodide emulsion (5 mole percent of iodide) containing 30 g. of gelatin and an amount of silver halide equivalent to 27.5 of silver nitrate are melted'and diluted with 50 ml. of distilled water.
  • the emulsion is acidified with 72 ccs. of 0.016 N acetic acid whereupon 5 g. of the color coupler no. 2 of the above list of examples of color couplers according to the present invention, dissolved in 25 cc. of ethanol, 5 cc. of 2N sodium hydroxide and 20 cc. of distilled water, are added. Then 5 g. of the color coupler no. 8
  • a clear transparent yellow-colored wedge image is obtained having an absorption maximum of 439 nm.
  • the yellow color formers according to the invention form on color development with aromatic primary amines such as p-phenylenediamine yellow dyes which excel by their favorable light absorption in the blue region of the spectrum and little absorption in the other regions. Furthermore, the dyes formed on color development show good resistance to heat, humidity and light and manifest a high activity during development, i.e., they furnish color images having high color density.
  • a color coupler B having the formula incorporated from a solution of 0.01 mole of color coupler in 24 ml. of distilled water, 12 ml. of ethanol and 4.5 ml. of 2N sodium hydroxide.
  • the resistance to moisture and heat of the dyestuffs formed on development by reaction with the oxidation product of pphenylene-diamine sulphate with the above color couplers is determined from the decrease in density of a developed wedge print after having stored said print for 24 hours at 60 C. and percent of relative humidity while being protected from light.
  • D represents a residue rendering the molecule fast to diffusion and comprising from five to 20 carbon atoms
  • R stands for hydrogen, alkyl, alkoxy, halogen, a dialkylamino group or a sulphamoyl group
  • Z represents the atoms necessary to close a nucleus of the thiazole series.
  • X is hydrogen or a group which splits off on color development
  • D is a residue rendering the molecule fast to diffusion and comprising from five to carbon atoms
  • R is hydrogen, alkyl, alkoxy, halogen, a dialkylamino group or a sulphamoyl group, and
  • Z represents the atoms necessary to close a nucleus of the thiazolc series
  • the Z group represents a thiazole nucleus substituted by an alkyl group, an aryl group, an aralkyl group, a heterocycle, a dialkylamino group, a sulphamoyl group, an alkoxycarbonyl group, a fluorosulphonyl group or a sulpho or carboxyl group in acid or salt form.
  • R is lower alkyl or lower alkoxy.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
US779627A 1968-01-05 1968-11-27 Color photography Expired - Lifetime US3645742A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB854/68A GB1246114A (en) 1968-01-05 1968-01-05 Benzoylacetamide derivatives and their use as colour couplers

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US3645742A true US3645742A (en) 1972-02-29

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US (1) US3645742A (en(2012))
BE (1) BE725904A (en(2012))
DE (1) DE1816899C3 (en(2012))
FR (1) FR1601789A (en(2012))
GB (1) GB1246114A (en(2012))

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1915334A (en) * 1930-10-16 1933-06-27 Du Pont Fluosilicate of organic heterocyclic bases and process of making it
US2075359A (en) * 1930-10-16 1937-03-30 Du Pont Insecticide
US2449244A (en) * 1945-01-25 1948-09-14 Gen Aniline & Film Corp Thioindoxyl couplers for color photography
US2668112A (en) * 1950-12-20 1954-02-02 Gevaert Photo Prod Nv Manufacture of photographic color images
US2992920A (en) * 1957-03-15 1961-07-18 Gevaert Photo Prod Nv Production of colored photographic images
US3245787A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images
US3369899A (en) * 1963-07-09 1968-02-20 Gevaert Photo Prod Nv Photographic materials containing aroylacetanilide type color couplers
US3393040A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
US3393041A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Multilayer silver halide elements containing thiazole color couplers for yellow

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1915334A (en) * 1930-10-16 1933-06-27 Du Pont Fluosilicate of organic heterocyclic bases and process of making it
US2075359A (en) * 1930-10-16 1937-03-30 Du Pont Insecticide
US2449244A (en) * 1945-01-25 1948-09-14 Gen Aniline & Film Corp Thioindoxyl couplers for color photography
US2668112A (en) * 1950-12-20 1954-02-02 Gevaert Photo Prod Nv Manufacture of photographic color images
US2992920A (en) * 1957-03-15 1961-07-18 Gevaert Photo Prod Nv Production of colored photographic images
US3245787A (en) * 1959-11-13 1966-04-12 Gevaert Photo Prod Nv Production of color photographic images
US3369899A (en) * 1963-07-09 1968-02-20 Gevaert Photo Prod Nv Photographic materials containing aroylacetanilide type color couplers
US3393040A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
US3393041A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Multilayer silver halide elements containing thiazole color couplers for yellow

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FR1601789A (en(2012)) 1970-09-14
DE1816899B2 (de) 1980-10-16
DE1816899C3 (de) 1981-07-23
GB1246114A (en) 1971-09-15
BE725904A (en(2012)) 1969-06-23
DE1816899A1 (de) 1969-07-31

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