GB1469696A - Diffusionfast couplers for colour photographic materials with light stability - Google Patents

Diffusionfast couplers for colour photographic materials with light stability

Info

Publication number
GB1469696A
GB1469696A GB2173874A GB2173874A GB1469696A GB 1469696 A GB1469696 A GB 1469696A GB 2173874 A GB2173874 A GB 2173874A GB 2173874 A GB2173874 A GB 2173874A GB 1469696 A GB1469696 A GB 1469696A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
group
couplers
preparation
reacted
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
GB2173874A
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.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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
Priority claimed from DE2325461A external-priority patent/DE2325461A1/en
Priority claimed from DE19732349562 external-priority patent/DE2349562A1/en
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of GB1469696A publication Critical patent/GB1469696A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl 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
    • 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
    • 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
    • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific

Landscapes

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

Abstract

1469696 Substituted hydroquinone ethers AGFA GEVAERT AG 16 May 1974 [19 May 1973 3 Oct 1973] 21738/74 Heading C2C [Also in Division G2] The preparation is described of colour couplers of the formula in which A represents a colour coupler group of the alkoylacetamide, aroylacetamide, phenol, naphthol, tetrahydronaphthol, indazolone or pyrazolone series which is attached to the connecting member X in a non-coupling position either directly or through a substituent; X represents -O-, -CONH-, -NHCO-, -NHCONH-, -COO or -OCONH-; R 2 represents an alkylene group in which one hydrogen atom may be substituted by an alkyl group and in the cases where R2 is attached to a magenta coupler group of the pyrazolone series through the connecting member -OCONH- the number of carbon atoms in the alkylene group is even and in the case where R 2 is attached through X to the alkoyl or aroyl moiety of a yellow alkoyl- or aroylacetamide coupler the alkylene group has the formula -CH 2 CH 2 -; R represents an alkyl or cycloalkyl group and R 1 represents hydrogen or an alkyl group. In typical examples of the preparation of magenta couplers hydroquinone and dodecyl bromide are reacted in alcohol in the presence of KOH to give 4-dodecyloxyphenol reaction of which with ethyl chloroacetate gives 4-dodecyloxyphenoxyacetic acid. The latter is converted to the acid chloride and reacted with the appropriate pyrazolone derivative to give 1 - (2,4,6 - trichlorophenyl) - 3 - [3 - (4 - dodecyloxy - phenoxyacetamido) - anilino - pyrazolone- (5). α - (4 - Methoxyphenoxy)myristic acid (from 4-methoxyphenol and α-bromomyristic acid ethyl ester) is converted to the acid chloride and reacted with the corresponding pyrazolone derivative to give 1-(2,4,6-trichlorophenyl)-3-(2- chloro - 5 - [α - (4 - methoxyphenoxy)myristoylamido]-anilino)-pyrazolone-(5). The preparation is described of analogous methods for the preparation of couplers containing pyrazolone groups and also those containing phenolic and aroylacetamido colour coupler groups at A in Formula I.
GB2173874A 1973-05-19 1974-05-16 Diffusionfast couplers for colour photographic materials with light stability Expired GB1469696A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2325461A DE2325461A1 (en) 1973-05-19 1973-05-19 DIFFUSION-RESISTANT PYRAZOLONE COUPLERS FOR COLOR PHOTOGRAPHIC MATERIALS
DE19732349562 DE2349562A1 (en) 1973-10-03 1973-10-03 Colour-formers of hydroquinone diether series - for photographic matls., stable to light, heat, moisture, oxidn. and redn.

Publications (1)

Publication Number Publication Date
GB1469696A true GB1469696A (en) 1977-04-06

Family

ID=25765178

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2173874A Expired GB1469696A (en) 1973-05-19 1974-05-16 Diffusionfast couplers for colour photographic materials with light stability

Country Status (6)

Country Link
JP (1) JPS5020723A (en)
CA (1) CA1033979A (en)
CH (1) CH600387A5 (en)
FR (1) FR2229998B1 (en)
GB (1) GB1469696A (en)
IT (1) IT1013190B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS557702A (en) * 1978-06-01 1980-01-19 Konishiroku Photo Ind Co Ltd Silver halide color photographic material
DE3272352D1 (en) * 1981-11-12 1986-09-04 Agfa Gevaert Nv Photographic elements containing ballasted compounds

Also Published As

Publication number Publication date
CH600387A5 (en) 1978-06-15
CA1033979A (en) 1978-07-04
JPS5020723A (en) 1975-03-05
FR2229998A1 (en) 1974-12-13
IT1013190B (en) 1977-03-30
FR2229998B1 (en) 1978-09-29

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Legal Events

Date Code Title Description
PS Patent sealed
746 Register noted 'licences of right' (sect. 46/1977)
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19920516