GB1183515A - Pyrazolone-containing Colour Couplers and Image Forming Layers Containing Them - Google Patents

Pyrazolone-containing Colour Couplers and Image Forming Layers Containing Them

Info

Publication number
GB1183515A
GB1183515A GB22360/67A GB2236067A GB1183515A GB 1183515 A GB1183515 A GB 1183515A GB 22360/67 A GB22360/67 A GB 22360/67A GB 2236067 A GB2236067 A GB 2236067A GB 1183515 A GB1183515 A GB 1183515A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
resulting
butyl
dichloroanilino
acetoxy
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
GB22360/67A
Inventor
Gregory James Lestina
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB1183515A publication Critical patent/GB1183515A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation 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
    • C09B43/132—Preparation 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 having the carboxylic group directly attached to an aromatic carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/28—Two oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • 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
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

1,183,515. 5-Pyrazolone derivatives. EASTMAN KODAK CO. 15 May, 1967 [16 May, 1966], No. 22360/67. Heading C2C. [Also in Division G2] Non-diffusing colour couplers contain one or two 5-pyrazolone nuclei at least one of which nuclei contains in the 1-, 3-, or 4-position a substituent consisting of or containing a non-coupling phenolic group. The couplers may be of the general formula where R is a radical containing a non-coupling phenolic group, R<SP>1</SP> is a radical containing a 5- pyrazolone nucleus, n is 1-4, m is 1 or 2, and various preferred types of compound are disclosed. 1 - { 4 - [α - (3 - t - Butyl - 4 - hydroxyphenoxy) - n - tetradecanamido] - 2,6 - dichlorophenyl} - 3 - (2,4 - dichloroanilino) - 5 - pyrazolone is prepared by reacting t-butyl hydroquinone with ethyl α - bromo - n - tetradecanoate, treating the resulting 2 - t - butyl - 4 - (α - carbethoxy - ntridecyloxy) - phenol with kOH in methyl alcohol, treating the resulting 2 - t - butyl - 4 - (α - carboxy - n - tetradecyloxy)-phenol with conc. H 2 SO 4 in acetic anhydride, reacting the resulting α-(4-acetoxy-3- t - butyl - phenoxy} - n - tetradecanoic acid with phosphorus pentachloride, reacting the resulting α - (4 - acetoxy - 3 - t - butylphenoxy) - n - tetra - decanoyl chloride with 1 - (4 - amino - 2,6 - dichlorophenyl) - 3 - (2,4 - dichloroanilino) - 5 - pyrazolone, and treating the resulting 1-{4-[α- (4 - acetoxy - 3 - t - butylphenoxy) - n - tetradecanamido] - 2,6 - dichlorophenyl} - 3 - (2,4 - dichloroanilino) - 5 - pyrazolone with NaOH in methyl alcohol. Other specified products are prepared in similar manner.
GB22360/67A 1966-05-16 1967-05-15 Pyrazolone-containing Colour Couplers and Image Forming Layers Containing Them Expired GB1183515A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US55015666A 1966-05-16 1966-05-16

Publications (1)

Publication Number Publication Date
GB1183515A true GB1183515A (en) 1970-03-11

Family

ID=24195977

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22360/67A Expired GB1183515A (en) 1966-05-16 1967-05-15 Pyrazolone-containing Colour Couplers and Image Forming Layers Containing Them

Country Status (6)

Country Link
US (1) US3519429A (en)
JP (1) JPS5145990B1 (en)
BE (1) BE698354A (en)
CH (1) CH478425A (en)
DE (1) DE1547803C3 (en)
GB (1) GB1183515A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2374704A1 (en) * 1976-12-17 1978-07-13 Konishiroku Photo Indust Co Lt
EP2100924A2 (en) 2008-03-14 2009-09-16 Konica Minolta Business Technologies, INC. Pyrazolotriazole compound and electrophotographic toner
EP2101222A1 (en) 2008-03-14 2009-09-16 Konica Minolta Business Technologies, INC. Electrophotographic toner
WO2012035876A1 (en) 2010-09-14 2012-03-22 コニカミノルタビジネステクノロジーズ株式会社 Toner for electrophotography and image-forming method

Families Citing this family (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3880661A (en) * 1971-12-29 1975-04-29 Eastman Kodak Co Silver halide emulsion containing acylamidophenol photographic couplers
JPS5333846B2 (en) * 1973-02-22 1978-09-18
US4021428A (en) * 1973-03-27 1977-05-03 Fuji Photo Film Co., Ltd. 4-Piperidino-5-oxo-2-pyrazolines
JPS566540B2 (en) * 1973-03-31 1981-02-12
JPS51105820A (en) * 1975-02-28 1976-09-20 Konishiroku Photo Ind HAROGENKAGINKARAASHINKANKOZAIRYO
JPS52152224A (en) * 1976-06-11 1977-12-17 Fuji Photo Film Co Ltd Color photographic light sensitive material
JPS5382411A (en) * 1976-12-28 1978-07-20 Konishiroku Photo Ind Co Ltd Silver halide color photographic material
US4228235A (en) * 1979-01-08 1980-10-14 Konishiroku Photo Industry Co., Ltd. Color photographic material
JPS56114946A (en) * 1980-02-15 1981-09-09 Konishiroku Photo Ind Co Ltd Silver halide photographic sensitive material
AU568488B2 (en) 1982-02-24 1988-01-07 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide colour photographic material
JPS5945442A (en) * 1982-09-08 1984-03-14 Fuji Photo Film Co Ltd Color photographic sensitive material
JPS59116647A (en) 1982-12-13 1984-07-05 Konishiroku Photo Ind Co Ltd Silver halide photosensitive material
JPS59188641A (en) 1983-04-11 1984-10-26 Fuji Photo Film Co Ltd Silver halide photographic emulsion
JPS60143331A (en) 1983-12-29 1985-07-29 Fuji Photo Film Co Ltd Silver halide photosensitive material
JPS6165248A (en) 1984-09-07 1986-04-03 Fuji Photo Film Co Ltd Silver halide color photograhc sensitive material
DE3435443A1 (en) * 1984-09-27 1986-04-03 Agfa-Gevaert Ag, 5090 Leverkusen PHOTOGRAPHIC RECORDING MATERIAL
JPS61251852A (en) 1985-04-30 1986-11-08 Konishiroku Photo Ind Co Ltd Method for processing silver halide color photographic sensitive material
US4725529A (en) 1985-04-30 1988-02-16 Konishiroku Photo Industry Co., Ltd. Developing inhibitor arrangment in light-sensitive silver halide color photographic materials
JPS61255342A (en) 1985-05-09 1986-11-13 Fuji Photo Film Co Ltd Silver halide color photographic sensitive material
CA1267557A (en) 1985-05-16 1990-04-10 Shigeharu Koboshi Method for color-developing a silver halide photographic light-sensitive material
AU588878B2 (en) 1985-05-31 1989-09-28 Konishiroku Photo Industry Co., Ltd. Method for forming direct positive color image
DE3682128D1 (en) 1985-07-17 1991-11-28 Konishiroku Photo Ind PHOTOGRAPHIC SILVER HALOGENID MATERIAL.
AU591540B2 (en) 1985-12-28 1989-12-07 Konishiroku Photo Industry Co., Ltd. Method of processing light-sensitive silver halide color photographic material
US5354646A (en) * 1986-03-26 1994-10-11 Konishiroku Photo Industry Co., Ltd. Method capable of rapidly processing a silver halide color photographic light-sensitive material
GB8614213D0 (en) * 1986-06-11 1986-07-16 Kodak Ltd Photographic acetanilide couplers
US4957855A (en) * 1989-09-21 1990-09-18 Eastman Kodak Company Photographic recording material with improved raw stock keeping
US5262292A (en) * 1991-04-23 1993-11-16 Eastman Kodak Company Photographic elements containing pyrazolone couplers and process
JP2877579B2 (en) * 1991-08-26 1999-03-31 コニカ株式会社 Silver halide color photographic materials
EP0536889A1 (en) * 1991-10-11 1993-04-14 Konica Corporation Silver halide color photographic light sensitive material
DE4136965A1 (en) * 1991-11-11 1993-05-13 Agfa Gevaert Ag PHOTOGRAPHIC RECORDING MATERIAL
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
JPH06214365A (en) * 1992-12-14 1994-08-05 Eastman Kodak Co Bleaching accelerator, bleaching composition and photographic element
US6365334B1 (en) 1993-10-22 2002-04-02 Eastman Kodak Company Photographic elements containing aryloxypyrazolone couplers and sulfur containing stabilizers
JPH07159955A (en) * 1993-12-01 1995-06-23 Konica Corp Silver halide color photographic sensitive material
JP3248036B2 (en) * 1993-12-20 2002-01-21 コニカ株式会社 Silver halide color photographic light-sensitive material
EP0684515A1 (en) 1994-05-27 1995-11-29 Eastman Kodak Company Photographic element and process incorporating a high dye-yield image coupler providing improved granularity
EP0686873B1 (en) 1994-06-08 2000-04-19 Eastman Kodak Company Color photographic element containing new epoxy scavengers for residual magenta coupler
JP3240342B2 (en) * 1994-06-09 2001-12-17 コニカ株式会社 Silver halide color photographic materials
JPH08101477A (en) 1994-08-01 1996-04-16 Eastman Kodak Co Coating composition for aqueous photograph
US5576152A (en) 1994-08-26 1996-11-19 Eastman Kodak Company Photographic paper formed with low molecular weight polyvinyl alcohol having low oxygen permeability
EP0711804A3 (en) 1994-11-14 1999-09-22 Ciba SC Holding AG Latent light stabilizers
DE69530198T2 (en) * 1995-09-18 2004-01-29 Ferrania Spa Process for the preparation of 4-arylthio-5-pyrazolone 2-equivalent magnetic couplers
EP0779536B1 (en) 1995-12-04 2005-10-19 Konica Corporation Light-and heat-sensitive recording material and recording method by use thereof
US5681691A (en) 1995-12-11 1997-10-28 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
US5985532A (en) 1995-12-11 1999-11-16 Eastman Kodak Company Photographic element containing an improved pyrozolotriazole coupler
US6494942B1 (en) 2000-09-15 2002-12-17 Larrie A Deardurff Dye-based ink jet compositions having improved stability and light fastness
US20130052594A1 (en) 2011-08-31 2013-02-28 Diane M. Carroll-Yacoby Motion picture films to provide archival images

Family Cites Families (9)

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Publication number Priority date Publication date Assignee Title
US2691659A (en) * 1954-10-12 Process for preparation of
BE442410A (en) * 1940-08-08
US2369489A (en) * 1941-09-25 1945-02-13 Eastman Kodak Co Acylated amino pyrazolone couplers
US2455170A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2511231A (en) * 1949-03-26 1950-06-13 Eastman Kodak Co 1-cyanophenyl-3-acylamino-5-pyrazolone couplers for color photography
BE496132A (en) * 1949-06-11
US2672417A (en) * 1949-12-31 1954-03-16 Gevaert Photo Prod Nv Production of color photographic images
US2618641A (en) * 1951-12-15 1952-11-18 Eastman Kodak Co Arylidene-bis-pyrazolones
BE619301A (en) * 1959-04-06

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2374704A1 (en) * 1976-12-17 1978-07-13 Konishiroku Photo Indust Co Lt
EP2100924A2 (en) 2008-03-14 2009-09-16 Konica Minolta Business Technologies, INC. Pyrazolotriazole compound and electrophotographic toner
EP2101222A1 (en) 2008-03-14 2009-09-16 Konica Minolta Business Technologies, INC. Electrophotographic toner
WO2012035876A1 (en) 2010-09-14 2012-03-22 コニカミノルタビジネステクノロジーズ株式会社 Toner for electrophotography and image-forming method

Also Published As

Publication number Publication date
CH478425A (en) 1969-09-15
DE1547803B2 (en) 1973-03-01
DE1547803A1 (en) 1970-12-23
JPS5145990B1 (en) 1976-12-06
US3519429A (en) 1970-07-07
DE1547803C3 (en) 1979-09-27
BE698354A (en) 1967-10-16

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE Patent expired