GB804974A - Improvements relating to process for preparing dye developers - Google Patents

Improvements relating to process for preparing dye developers

Info

Publication number
GB804974A
GB804974A GB2850557A GB2850557A GB804974A GB 804974 A GB804974 A GB 804974A GB 2850557 A GB2850557 A GB 2850557A GB 2850557 A GB2850557 A GB 2850557A GB 804974 A GB804974 A GB 804974A
Authority
GB
United Kingdom
Prior art keywords
amino
hydroxy
dye
anthraquinone
developer
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
Application number
GB2850557A
Inventor
Elkan Rogers Blout
Richard Stancliffe Corley
Saul Gerald Cohen
Milton Green
Howard Gardner Rogers
Myron Sydney Simon
Robert Burns Woodward
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Polaroid Corp
International Polaroid Corp
Original Assignee
Polaroid Corp
International Polaroid Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Polaroid Corp, International Polaroid Corp filed Critical Polaroid Corp
Publication of GB804974A publication Critical patent/GB804974A/en
Expired legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02Photosensitive materials characterised by the image-forming section
    • G03C8/08Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B6/00Anthracene dyes not provided for above
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02Photosensitive materials characterised by the image-forming section
    • G03C8/08Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds
    • G03C8/10Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors
    • G03C8/12Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of organic compounds of dyes or their precursors characterised by the releasing mechanism
    • G03C8/14Oxidation of the chromogenic substances
    • G03C8/16Oxidation of the chromogenic substances initially diffusible in alkaline environment
    • G03C8/18Dye developers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C8/00Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/42Structural details

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Structural Engineering (AREA)
  • Architecture (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Color Printing (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Coloring (AREA)
  • Developing Agents For Electrophotography (AREA)

Abstract

The invention comprises dye developers and a process of making them by the combination of a dye containing a hydroxyl, primary amino, secondary amino, carboxyl, or sulpho group with a developer compound containing an aryl nucleus substituted by at least two substituents selected from hydroxyl, amino, and substituted amino groups so that the resulting compound is capable of developing exposed silver halide and having a further substituent, which process comprises forming, between said dye and said developer compound, a bond through which the colour characteristics of the dye unit are maintained substantially free from the influence of the developer unit by the reaction of said hydroxyl, primary or secondary amino, carboxyl or sulpho group of the dye with the further substituent of the developer compound. In particular, dyes containing hydroxy or primary or secondary amino with compounds of the formul : <FORM:0804974/IV (c)/1> or <FORM:0804974/IV (c)/2> or <FORM:0804974/IV (c)/3> where D1 is a group containing an aryl nucleus substituted by at least two substituents selected from hydroxy, amino, and/or substituted amino so that the resulting compound is capable of developing exposed silver halide, R4 is hydrogen or alkyl, R5 is chlorine, a group of the formula: <FORM:0804974/IV (c)/4> hydroxy, amino, aryloxy, alkoxy, alkylamino, or alkyl. Other methods of building up these molecules are referred to generally. One of the hydroxy, amino, or substituted amino groups of D1 may be acylated, and said acyl group removed by hydrolysis subsequently. Examples of suitable bonds joining dye and developer units are a covalent bond, and the groups -CO-, -CH2.CONH-, -CJ2-(where J is hydrogen, alkyl, or aryl), -SO2-, -B-, (where B is a bivalent hydrocarbon residue, e.g. alkylene or arylene), -NJ-B-, -SO2-B-SO2-, -CO-B-, -CO-B-CO-, -alkylene -NH-NH-alkylene-, -B-O-, -O-P(OH)-O-, -O-B-O-, -SO3-B-NH-, or the bivalent residue of a hydroaromatic or heterocyclic ring. In examples: (1) O - monobenzoyl - hydroquinonylamino - dichloro - s - triazine is reacted with p - aminoazobenzene, giving after hydrolysis of a chlorine atom, 2 - hydroquinonylamino - 4 - (p - phenylazo - anilino) - 6 - hydroxy - s - triazine, or with dimethoxy - diphenyl - disazo - bis - 8 - amino - 1 - naphthol - 5,7 - disodium sulphonate, 1 - amino-4 - (p - aminophenylamino) - anthraquinone - 2 - sodium sulphonate; 4 - amino - 41 - sulphoazobenzene, or 4,8 - diamino - 1,5 - dihydroxyanthraquinone; (2) gentisic acid chloride, homogentisic acid chloride or homogentisic acid lactone is reacted with 1,4-bis-(beta-aminoethylamino) - anthraquinone, or with 1 - amino - 4 - (p - aminoanilino) - anthraquinone-2-sulphonic acid; (3) homogentisic acid chloride dibenzoate is reacted with 1-phenyl-3-amino-4-phenylazo - 5 - pyrazolone, followed by hydrolysis; (4) chloroacetamido-hydroquinonone monobenzoate is reacted with 1,4-bis-(beta-aminoethylamino)- or 1,4-bis-(beta-hydroxyethylamino)-anthraquinone or with 1-amino-4-(p - aminoanilino) - anthraquinone - 2 - sodium sulphonate. Other examples of developer unit D1 are 3,4 - dihydroxyphenyl, 1 - hydroxy - 4 - aminophenyl, 1 - hydroxy - 4 - methylaminophenyl, 1,2,3 - trihydroxyphenyl, and 1 - hydroxy - 2 - aminonaphthyl. Specifications 804,973 and 804,975 are referred to.
GB2850557A 1954-03-09 1955-03-09 Improvements relating to process for preparing dye developers Expired GB804974A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US41507354A 1954-03-09 1954-03-09

Publications (1)

Publication Number Publication Date
GB804974A true GB804974A (en) 1958-11-26

Family

ID=23644267

Family Applications (6)

Application Number Title Priority Date Filing Date
GB690455A Expired GB804971A (en) 1954-03-09 1955-03-09 Improvements in or relating to photography
GB2850457A Expired GB804973A (en) 1954-03-09 1955-03-09 Improvements relating to process for preparing dye developers
GB2850557A Expired GB804974A (en) 1954-03-09 1955-03-09 Improvements relating to process for preparing dye developers
GB2850657A Expired GB804975A (en) 1954-03-09 1955-03-09 Improvements relating to process for preparing dye developers
GB3880457A Expired GB804976A (en) 1954-03-09 1955-03-09 Improvements relating to color photography
GB690555A Expired GB804972A (en) 1954-03-09 1955-03-09 Improvements in or relating to photography

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB690455A Expired GB804971A (en) 1954-03-09 1955-03-09 Improvements in or relating to photography
GB2850457A Expired GB804973A (en) 1954-03-09 1955-03-09 Improvements relating to process for preparing dye developers

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB2850657A Expired GB804975A (en) 1954-03-09 1955-03-09 Improvements relating to process for preparing dye developers
GB3880457A Expired GB804976A (en) 1954-03-09 1955-03-09 Improvements relating to color photography
GB690555A Expired GB804972A (en) 1954-03-09 1955-03-09 Improvements in or relating to photography

Country Status (6)

Country Link
BE (1) BE554213A (en)
CH (7) CH363560A (en)
DE (5) DE1419842A1 (en)
FR (2) FR1178429A (en)
GB (6) GB804971A (en)
NL (2) NL103503C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3135605A (en) * 1962-02-15 1964-06-02 Polaroid Corp Novel photographic products, processes, and compositions employing novel anthraquinone dye developers
US3239339A (en) * 1961-05-05 1966-03-08 Polaroid Corp Novel photographic products, compositions and processes
US3241963A (en) * 1962-02-19 1966-03-22 Polaroid Corp Novel photographic products, processes and compositions

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3053656A (en) * 1954-07-01 1962-09-11 Polaroid Corp Photographic silver halide developers containing triazine rings
NL132776C (en) * 1959-01-26
NL247650A (en) * 1959-01-26
US3230083A (en) * 1959-04-02 1966-01-18 Polaroid Corp Photographic processes and products
DE1422849B1 (en) * 1960-08-22 1970-07-09 Eastman Kodak Co Multilayer photographic recording material for the dye developer diffusion process
NL268155A (en) * 1960-08-22
DE1157484B (en) * 1960-08-22 1963-11-14 Eastman Kodak Co Process for rendering colored positive images produced by diffusion transfer processes using a dye developer to lightfast
DE1422850B1 (en) * 1960-08-22 1970-06-04 Eastman Kodak Co Dye developer diffusion process for the production of multicolored images
NL268156A (en) * 1960-08-22
FR83752E (en) * 1960-11-23 1965-01-15
BE607371A (en) * 1960-11-25
US3255002A (en) * 1961-03-09 1966-06-07 Polaroid Corp Color photographic process and product
BE614794A (en) * 1961-03-09
US3265505A (en) * 1962-04-02 1966-08-09 Eastman Kodak Co Photographic products
US3077400A (en) * 1962-04-26 1963-02-12 Polaroid Corp Color diffusion transfer using gelatinsilver halide emulsions containing cellulose ethers
US3287133A (en) * 1963-03-01 1966-11-22 Eastman Kodak Co Photographic dye developer dispersions utilizing water-soluble sulfites
US3837852A (en) * 1972-10-02 1974-09-24 Gaf Corp Color diffusion transfer process utilizing azo coupling to actuate diffusion of color providing species
JPS5421255B2 (en) * 1974-10-08 1979-07-28

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2543691A (en) * 1946-06-07 1951-02-27 Gen Aniline & Film Corp Azo dyes as silver halide photographic developing agents
US2661293A (en) * 1946-10-08 1953-12-01 Polaroid Corp Process of producing a colored photographic image by means of exhaustion of developer
US2559643A (en) * 1948-02-19 1951-07-10 Polaroid Corp Photographic product and process
US2647649A (en) * 1951-06-28 1953-08-04 Onno L Maynard Trash moving fork for tractors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3239339A (en) * 1961-05-05 1966-03-08 Polaroid Corp Novel photographic products, compositions and processes
US3135605A (en) * 1962-02-15 1964-06-02 Polaroid Corp Novel photographic products, processes, and compositions employing novel anthraquinone dye developers
US3241963A (en) * 1962-02-19 1966-03-22 Polaroid Corp Novel photographic products, processes and compositions

Also Published As

Publication number Publication date
NL103503C (en) 1963-01-15
GB804976A (en) 1958-11-26
CH386444A (en) 1965-01-15
NL195422A (en) 1962-08-15
CH404832A (en) 1965-12-31
CH363560A (en) 1962-07-31
NL195421A (en) 1962-08-15
CH358327A (en) 1961-11-15
GB804972A (en) 1958-11-26
CH386245A (en) 1964-12-31
DE1419842A1 (en) 1968-12-19
GB804973A (en) 1958-11-26
FR1178429A (en) 1959-05-11
GB804975A (en) 1958-11-26
DE1035660B (en) 1958-08-07
DE1066092B (en)
CH391931A (en) 1965-05-15
DE1196075B (en) 1965-07-01
DE1172386B (en) 1964-06-18
FR1168292A (en) 1958-12-05
GB804971A (en) 1958-11-26
BE554213A (en) 1957-07-16
NL103504C (en) 1963-01-15
CH356356A (en) 1961-08-15

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