GB1069533A - 1-fluoroalkyl-2-pyrazoline-5- one colour couplers - Google Patents

1-fluoroalkyl-2-pyrazoline-5- one colour couplers

Info

Publication number
GB1069533A
GB1069533A GB29740/64A GB2974064A GB1069533A GB 1069533 A GB1069533 A GB 1069533A GB 29740/64 A GB29740/64 A GB 29740/64A GB 2974064 A GB2974064 A GB 2974064A GB 1069533 A GB1069533 A GB 1069533A
Authority
GB
United Kingdom
Prior art keywords
acid
prepared
pyrazoline
aryl
alkyl
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
GB29740/64A
Inventor
Hector Alfons Van Den Eynde
Robert Joseph Pollet
Arthur Henri De Cat
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 NV
Original Assignee
Agfa Gevaert NV
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 Agfa Gevaert NV filed Critical Agfa Gevaert NV
Priority to GB29740/64A priority Critical patent/GB1069533A/en
Priority to US472017A priority patent/US3462270A/en
Priority to FR25698A priority patent/FR1441166A/en
Priority to NL6509593A priority patent/NL6509593A/xx
Priority to DE19651547891 priority patent/DE1547891C3/en
Priority to CH1033465A priority patent/CH456344A/en
Priority to BE667370D priority patent/BE667370A/xx
Publication of GB1069533A publication Critical patent/GB1069533A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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

Abstract

The invention comprises 2-pyrazoline-5-one compounds of the following general formula or bis (2-pyrazoline-5-one therefrom by linking the 2-pyrazoline-5-one nuclei in the 4-position by means of a -CH2-group <FORM:1069533/C2/1> wherein X represents a hydrogen or fluorine atom, R represents a hydrogen atom, an alkyl radical or an aryl radical, n is a positive integer from 1 to 10 inclusive and R1 represents an alkyl, aryl, -NH- aryl, -NHCO- aryl, -NHCO- alkyl, -NHCONH- alkyl or -NHCONH- aryl radical, which radicals may be further substituted and may contain a radical rendering the molecule fast to diffusion in an hydrophilic colloid medium. The compounds wherein R1 is alkyl or aryl are prepared by condensation of the appropriate hydrazine with an appropriate keto compound of the acetoacetic acid type. The compounds wherein R1 has the other meanings are prepared by condensation of the appropriate 1-fluoralkyl-3-amino - 2 - pyrazoline - 5 - one with an appropriate acid chloride, acid anhydride or isocyanate. The 1-fluoralkyl-3-amino-2-pyrazoline-5-one is prepared by condensation of a fluoroalkyl hydrazine with ethyl b -ethoxy-b -imino-propionate. o - Hexadecyloxy - benzoic acid is prepared by reacting hexadecyl bromide with salicylaldehyde to give o-hexadecyloxy-benzaldehyde which is oxidized with KMnO4. 3-Sulpho-6-hexadecyloxybenzoi acid, 3 - chlorosulphonyl - 6-hexadecyloxybenzoic acid, 3 - fluorosulphonyl-6 - hexadecyloxybenzoic acid and 3 - fluorosulphonyl - 6 - hexadecyloxybenzoyl chloride are prepared by method analogous to those described in Specification 1,039,965. p - Hexadecylthio - benzoic acid is prepared by reacting hexadecyl bromide with p-mer-captobenzoic acid. On oxidation with H2O2 p-hexadecylsulphonyl-benzoic acid is formed which is reacted with thionyl chloride to give p-hexadecylsulphonyl-benzoyl chloride. p-Hexadecylsulphonylphenyl isocyanate is prepared by reacting p-hexadecylsulphonyl-aniline with phosgene.
GB29740/64A 1964-07-24 1964-07-24 1-fluoroalkyl-2-pyrazoline-5- one colour couplers Expired GB1069533A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB29740/64A GB1069533A (en) 1964-07-24 1964-07-24 1-fluoroalkyl-2-pyrazoline-5- one colour couplers
US472017A US3462270A (en) 1964-07-24 1965-07-14 Color photography utilizing 1-fluoroalkyl - 2 - pyrazoline - 5 - one colour couplers
FR25698A FR1441166A (en) 1964-07-24 1965-07-21 Chromogenic couplers 1-fluoroalkyl-2-pyrazolin-5-one
NL6509593A NL6509593A (en) 1964-07-24 1965-07-23
DE19651547891 DE1547891C3 (en) 1964-07-24 1965-07-23 Color photographic recording material
CH1033465A CH456344A (en) 1964-07-24 1965-07-23 Photographic material
BE667370D BE667370A (en) 1964-07-24 1965-07-26

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB29740/64A GB1069533A (en) 1964-07-24 1964-07-24 1-fluoroalkyl-2-pyrazoline-5- one colour couplers

Publications (1)

Publication Number Publication Date
GB1069533A true GB1069533A (en) 1967-05-17

Family

ID=10296403

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29740/64A Expired GB1069533A (en) 1964-07-24 1964-07-24 1-fluoroalkyl-2-pyrazoline-5- one colour couplers

Country Status (5)

Country Link
US (1) US3462270A (en)
BE (1) BE667370A (en)
CH (1) CH456344A (en)
GB (1) GB1069533A (en)
NL (1) NL6509593A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4056533A (en) 1973-04-17 1977-11-01 Bayer Aktiengesellschaft Pyrazol-5-ones
US4081596A (en) 1973-04-17 1978-03-28 Bayer Aktiengesellschaft Pyrazol-5-ones

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1458364A (en) * 1973-04-06 1976-12-15 Agfa Gevaert 2-pyrazolin-5-one derivatives as colour couplers for magenta
JPS532728B2 (en) * 1974-01-25 1978-01-31
JPS5412220B2 (en) * 1974-04-12 1979-05-21

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2895826A (en) * 1956-10-08 1959-07-21 Eastman Kodak Co Photographic color couplers containing fluoroalkylcarbonamido groups

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4056533A (en) 1973-04-17 1977-11-01 Bayer Aktiengesellschaft Pyrazol-5-ones
US4081596A (en) 1973-04-17 1978-03-28 Bayer Aktiengesellschaft Pyrazol-5-ones

Also Published As

Publication number Publication date
BE667370A (en) 1966-01-26
DE1547891B2 (en) 1975-12-04
NL6509593A (en) 1965-12-27
DE1547891A1 (en) 1969-07-31
CH456344A (en) 1968-07-15
US3462270A (en) 1969-08-19

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