US2846307A - Isoxazolone couplers in color photography - Google Patents

Isoxazolone couplers in color photography Download PDF

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Publication number
US2846307A
US2846307A US541097A US54109755A US2846307A US 2846307 A US2846307 A US 2846307A US 541097 A US541097 A US 541097A US 54109755 A US54109755 A US 54109755A US 2846307 A US2846307 A US 2846307A
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United States
Prior art keywords
parts
benzisoxazolone
colour
acid
solution
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Expired - Lifetime
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US541097A
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English (en)
Inventor
Woolley John Mathers
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • 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

  • This invention relates to colour photographic, images and more particularly to a novel process for the production of colour photographic images by colour development in the presence of a colour coupler, to photographic developers and to photographic material containing such a coupler, and to photographic materials containing coloured'images of the kind obtainable from such a colour coupler.
  • Z represents the atoms required to complete a vh-omocyclic, heterocyclic or polycyclic nucleus and R represents hydrogen or an acyl group.
  • the nucleus represented by Z may carry substituents for example halogeno, sulphonic acid, carboxylic acid, 'carboxylic ester or amide substituents.
  • Z may represent .for example the atoms required to complete a benzene .nucleus, unsubstituted or substituted, that is to :say the compounds may be B-y-benzisoxazolones which may carry substituents on the l-, 4-, 5-, 6- or 7-positions.
  • the .system of numbering used in this specification for fi-y-benzisoxazolones is that given in the The Ring Index by Patterson and Capell published by Reinhold Publishing Corporation (1940) (No. 729).
  • As an example of a vheterocyclic (and polycyclic) nucleus there may be mentioned the quinoline nucleus.
  • the colour coupler used in the process of our invention may be used in the developing solution or it may be included in a light-sensitive layer of .a'multilayer photographic material or in a non-light sensitive layer ad- 2, jacent to a sensitive layer or separated therefrom by a water-permeable colloid layer.
  • an insoluble colour coupler may be used, or a soluble colour coupler enclosed in particles of water-insoluble, water-permeable material but ,it is preferred to use colour couplers which contain a substituent rendering them fast to diffusion, for example an alkyl chain of at least 5 carbon atoms and, if desired, a solubilising group.
  • the colour couplers used in the process of our'inyention may be made by the general processes known for use.in the synthesis of flzy-benzisoxazolones for example by reducing the appropriate .o-nitrocarboxylic acid ,or an ester thereof.
  • an alcohol such as octadecanol
  • an amine such as octadecylamine or '1
  • the colour photographic developers which may be used in the present'invention include the mono-, diand tri-amino-aryl compounds.
  • monoamino developers there may be mentionedtaminwphenols and amino-cresols and their ,halogen .derivatives and amino .naphthols.
  • the ,developerspreferably used and givingthe best results in connection with thepresent .invention are the aromatic 01'IhO-.:and para-diamineszsllch as para-.phenylene -.diamine. and its substitution products.
  • the .colour coupling which occurs in the process of our invention when an exposed .gelatino-s'ilyer halide emulsion is treated with a primary aromatic amino developing ⁇ agent in the presenceof one of the colourcouplers as herein- :befotedefined, proceeds by .a surprising and wholly-unexpected reaction in'which the isoxazolone ringgis split and an azo...dyes tuif,is formed in which the residue of the .oxidationproduct of the developing agent is attached to the nitrogen atom which previously formed the tl-nitrogen atom .of the isoxazolone, ring.
  • a colour photographic element which contains in at least one emulsion layer, a colour image comprising a dyestufi of the formula:
  • Z has the significance indicated above and X represents the group of atoms which together with the group -NH forms a primary aromatic amine which is capable of developing exposed silver halide emulsions.
  • the dyestufi images formed by the process of our invention are superior to the known azamethine images in ,their chemical stability and their fastness to light and the process of our invention provides a simple method of obtaining colour photographic images of good fastness properties by direct development of an exposed gelatinosilver halide emulsion with a colour photographic developer.
  • Example 1 A developer solution is made up according to the following formula:
  • N:N-diethyl-p-phenylene-diamine sulphate used in the developer solution in the above example there may be used 4-amino-3-methyl-N:N-diethylaniline, 4-amino-3-ethoxy-N:N-diethylaniline or p-phenylene diamine.
  • Example 2 In place of the 0.5 part of firy-benzisoxazolone used in Example 1 there is used 0.5 part of 4-carboxy-flz'y-benzisoxazolone which may be prepared as follows:
  • Example 3 In place of the 05 part of ,Bzy-benzisoxazolone used in Example 1, there is used 0.5 part of 6-carboxy-flz'y-benzisoxazolone which may be prepared as follows:
  • the product is purified by stirring it with 20 parts of cold methanol for 15 minutes filtering off and recrystallising from methanol.
  • the 6-carboxyflw-benzisoxazolone so formed does not melt below 300 C.
  • the yellow azo dyestutf produced in the exposed parts of the photographic silver halide emulsion layer is 2:5-dicarboxy 4 diethylamino-azobenzene.
  • Example 4 In place of the 0.5 part of flzy-benzisoxazo1one used in Example 1 there is used 0.5 part of l-phenylcarbamyl- 4-carboxy-fiw-benzisoxazolone which may be made as follows:
  • Example 5 In place of the 0.5 part of fiz'y-benzisoxazolone used in Example 1 there is used 0.5 part of l-carbethoxy-4-carboxy-flry-benzisoxazolone which may be prepared as follows:
  • Example 6 In place of the 0.5 part of fiz'y-benzisoxazolone used in Example 1, there is used 0.5 part of l-p-toluene-sulphonyl-4-carboxy- ⁇ iz'y-benzisoxazolone which may be prepared as follows:
  • Example 7 1 part of the octadecyl ester of -1-acetyl-4-carboxyphenylene diamine as developing agent.
  • the developed silver is bleached and the silver salts-removed by'a' fixing *bath.
  • a yellow azo dyestufi image-corresponding in v --gradation of density to the intensity of the-incident light is- -obtained.
  • the octadecyl ester of 1-acetyl-4-carboxyfivy-benzisoxazolone may be prepared as follows:
  • the solution is'boiled for 5 minutesand-thebenzene and excess pyridine are then removed by vacuum distillation.
  • the residue is dissolved in 10 parts of methanol and the solution is poured into a mixture of 100 parts of water and 10 parts of hydrochloric acid.
  • the white precipitate so formed is filtered olf, washed with water, then with methanol, and finally with ether and then dried.
  • the product is recrystallised from methanol and then melts at 98l00 C.
  • aqueous caustic soda solution aqueous caustic soda solution
  • the solution is'then added to 100 parts of a molten gelatino-silver halide
  • the emulsion is coated as a layer on a substrate and the layer is dried.
  • the layer is exposed to light, developed with 'a solution of NzN-diethyl-p-phenylenediamine, the developed silver is bleached and the silver salts fixed.
  • the layer is washer with water.
  • the p:' -benzisoxazolone-4-carboxy-(2-N-methyl-N- octadecylamino-S-sulpho-benz)-amide used in this example may be prepared as follows:
  • the gummy precipitate so-formed is allowed to settle, and the supernatant liquid is decanted.
  • the gummyresidue is washed with water and thenboiled with parts of methanol.
  • the solution so formed is cooledandthe 1 wpale grey solid whichis precipitated is filtered .ofhand recrystallised from glacialacetic acid.
  • the product :melts at 212 C.
  • -'2 nitrotoluene-4 sulphonic acid is loxidised in -the usual manner with alkaline permanganate solution to give 2- nitro-Lsulphobenzoic acid.
  • the benzisoxazolone-6-sulphonic acid-content ofthe filtrate is estimated by titration with N/-2 sodium 'nitrite-solution'and water is then added to the filtrate to adjust the concentration of 3:'y-benzisoxazolone-fi-sulphonic acid to 10% by weight.
  • a photographic silver halide emulsion layer which has been exposed to light is developed in the solution at 20 C. and. the silver and silver halide inthe exposed parts of the'layer are removed.
  • the yelowishbrown azo dyestuff in the exposed parts of the layer is changed to a bright magenta colour on treatment .With Y hydrochloric acid.
  • hydro-quinoline-isoxazolone used in this example may be prepared as follows:
  • Example 13 In place of the 1 part of 8:y-benzisoxazolone-4-carboxy (2' N methyl N octadecylamino 5' sulphobenz)-arnide used in Example 9, 1 part of 4:6-dicarboxy- 7-octadecyloxy benzisoxazolone prepared as described below, is used. A yellow azo dyestufi image is obtained.
  • the 4:6-dicarboxy-7-octadecyloxybenzisoxazolone used in this example may be prepared as follows:
  • S-hydroxytrimellitic acid is converted to the trimethyl ester by heating it under a reflux condenser for 6 hours with methanol containing 5% by weight of-anhydrous hydrochloric acid.
  • Z represents the atoms required to complete a nucleus selected from the class consisting of benzene and quinoline nuclei and R represents a member of the class consisting of hydrogen and an acyl group.
  • Z represents the atoms required to complete a nucleus selected from the class consisting of benzene and quinoline nuclei and R represents a member of the class consisting of hydrogen and an acyl group.
  • said color coupler is a hydroxyquinoline-isoxazolone.
  • a light sensitive, silver halide emulsion layer containing 4:6-dicarboxy-7-octadecyloxy benzisoxazolone References Cited in the file of this Patent 12.
  • said color coupler is 4:6-dicarboxy-7-octadecyloxy benzisoxazolone.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US541097A 1954-10-22 1955-10-17 Isoxazolone couplers in color photography Expired - Lifetime US2846307A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB30445/54A GB778089A (en) 1954-10-22 1954-10-22 Colour photographic images
GB3044555 1955-10-07

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US2846307A true US2846307A (en) 1958-08-05

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US (1) US2846307A (enrdf_load_stackoverflow)
BE (1) BE542229A (enrdf_load_stackoverflow)
DE (1) DE963296C (enrdf_load_stackoverflow)
FR (1) FR1137702A (enrdf_load_stackoverflow)
GB (1) GB778089A (enrdf_load_stackoverflow)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013018A (en) * 1959-04-24 1961-12-12 Du Pont 5-cyanomethylene-2-pyrrolidones
US4059447A (en) * 1974-12-31 1977-11-22 Agfa-Gevaert Aktiengesellschaft Photographic material containing oxazolinone-2 couplers
US4139389A (en) * 1977-03-07 1979-02-13 Eastman Kodak Company Cleavable aromatic nitro compounds
US4139379A (en) * 1977-03-07 1979-02-13 Eastman Kodak Company Photographic elements containing ballasted electron-accepting nucleophilic displacement compounds
US4192679A (en) * 1978-11-15 1980-03-11 Eastman Kodak Company Bifunctional benzisoxazolone compounds
US4192678A (en) * 1978-11-15 1980-03-11 Eastman Kodak Company N-alkyl- or N-aryl-benzisoxazolone scavenger compounds
US4199354A (en) * 1973-01-26 1980-04-22 Eastman Kodak Company Positive-working immobile photographic compounds and photographic elements containing same
US4199355A (en) * 1975-06-24 1980-04-22 Eastman Kodak Company Positive-working immobile photographic compounds and photographic elements containing same
US4218368A (en) * 1977-03-07 1980-08-19 Eastman Kodak Company Aromatic nitro compounds containing diffusible groups cleavable by intramolecular nucleophilic displacement
US4278598A (en) * 1974-12-20 1981-07-14 Eastman Kodak Company Positive-working immobile intramolecular nucleophilic displacement compounds and photographic elements containing same
US4481268A (en) * 1981-02-09 1984-11-06 Eastman Kodak Company Method of forming a photographic dye image
US5554493A (en) * 1995-03-15 1996-09-10 Eastman Kodak Company Use of 2,1-benzisoxazol-3(1H)-ones as antioxidants in color photographic processing methods

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3720932B2 (ja) * 1996-09-18 2005-11-30 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2124612A (en) * 1935-07-13 1938-07-26 Agfa Ansco Corp Color photography
US2331326A (en) * 1939-07-22 1943-10-12 Ilford Ltd Production of colored photographic images

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2124612A (en) * 1935-07-13 1938-07-26 Agfa Ansco Corp Color photography
US2331326A (en) * 1939-07-22 1943-10-12 Ilford Ltd Production of colored photographic images

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3013018A (en) * 1959-04-24 1961-12-12 Du Pont 5-cyanomethylene-2-pyrrolidones
US4199354A (en) * 1973-01-26 1980-04-22 Eastman Kodak Company Positive-working immobile photographic compounds and photographic elements containing same
US4278598A (en) * 1974-12-20 1981-07-14 Eastman Kodak Company Positive-working immobile intramolecular nucleophilic displacement compounds and photographic elements containing same
US4059447A (en) * 1974-12-31 1977-11-22 Agfa-Gevaert Aktiengesellschaft Photographic material containing oxazolinone-2 couplers
US4199355A (en) * 1975-06-24 1980-04-22 Eastman Kodak Company Positive-working immobile photographic compounds and photographic elements containing same
US4139389A (en) * 1977-03-07 1979-02-13 Eastman Kodak Company Cleavable aromatic nitro compounds
US4139379A (en) * 1977-03-07 1979-02-13 Eastman Kodak Company Photographic elements containing ballasted electron-accepting nucleophilic displacement compounds
US4218368A (en) * 1977-03-07 1980-08-19 Eastman Kodak Company Aromatic nitro compounds containing diffusible groups cleavable by intramolecular nucleophilic displacement
US4192679A (en) * 1978-11-15 1980-03-11 Eastman Kodak Company Bifunctional benzisoxazolone compounds
US4192678A (en) * 1978-11-15 1980-03-11 Eastman Kodak Company N-alkyl- or N-aryl-benzisoxazolone scavenger compounds
US4481268A (en) * 1981-02-09 1984-11-06 Eastman Kodak Company Method of forming a photographic dye image
US5554493A (en) * 1995-03-15 1996-09-10 Eastman Kodak Company Use of 2,1-benzisoxazol-3(1H)-ones as antioxidants in color photographic processing methods

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DE963296C (de) 1957-05-02
GB778089A (en) 1957-07-03
BE542229A (enrdf_load_stackoverflow)
FR1137702A (fr) 1957-06-03

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