GB886091A - Process for the production of methine dyestuffs - Google Patents

Process for the production of methine dyestuffs

Info

Publication number
GB886091A
GB886091A GB4157659A GB4157659A GB886091A GB 886091 A GB886091 A GB 886091A GB 4157659 A GB4157659 A GB 4157659A GB 4157659 A GB4157659 A GB 4157659A GB 886091 A GB886091 A GB 886091A
Authority
GB
United Kingdom
Prior art keywords
methyl
alkyl
group
substituted
acid
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
GB4157659A
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.)
Bayer AG
Original Assignee
Bayer 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
Application filed by Bayer AG filed Critical Bayer AG
Publication of GB886091A publication Critical patent/GB886091A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • 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
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/832—Methine or polymethine dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Coloring (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Monomethine dyes are prepared by reacting a 5-pyrazolone of one of the formulae <FORM:0886091/IV (c)/1> wherein R1 is hydrogen or an alkyl, aralkyl, substituted or unsubstituted aryl carboxylic acid or carbalkoxy group, R2 is hydrogen or an alkyl, aralkyl, substituted or unsubstituted aryl or amidinyl group, R3 is an alkyl or aryl group and R4 is an alkyl group, with a phenol, naphthol, N-alkyl or N-aryl aromatic amine, heterocyclic ketomethylene compound or an indole of the formula <FORM:0886091/IV (c)/2> wherein R5 is hydrogen or an alkyl, aralkyl or aryl group and R6 is an alkyl or aryl group, in the presence of an acidic or basic condensing agent. The N-substituted aromatic amino may be N,N-dimethyl aniline, N,N-diethylaniline, N-(b -cyanethyl)-N-ethyl aniline, N-(b -hydroxyethyl)-N-butyl aniline, N-methyl-diphenylamine or 4-methoxy-N-methyl-diphenylamine. The heterocyclic ketomethylene compound may be barbituric acid, hydantoin, 3,6-dihydroxypyridazine or a 5-pyrazolone which may be substituted in the 1-position by a phenyl group which may contain methyl, chloro, nitro, amino, carboxy, methoxy, sulphamino, methylsulphonylamino, benzene-sulphonylamino or ethylsulphonyl substituents. and in the 3-position by a methyl, carboxy, carboxyethyl, carbamide or methoxyphenyl group. In formulae I and II, R1 may be methyl, carbethoxy, carboxy or p-methoxyphenyl, R2 may be phenyl, tolyl, chlorophenyl or nitrophenyl, and R3 and R4 may be methyl or ethyl. The compound of formula III may be 2-methyl indole or 1-methyl 2-phenyl indole. The acid condensing agent may be acetic anhydride, acetyl chloride, phosphorus oxychloride, thionyl chloride, syrupy phosphoric acid or acetic acid, and the basic condensing agent may be piperidine or triethylamine.
GB4157659A 1958-12-09 1959-12-07 Process for the production of methine dyestuffs Expired GB886091A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF29767A DE1157582B (en) 1958-12-09 1958-12-09 Process for dyeing and printing structures made of aromatic polyesters, polyamides and polyurethanes

Publications (1)

Publication Number Publication Date
GB886091A true GB886091A (en) 1962-01-03

Family

ID=7093453

Family Applications (2)

Application Number Title Priority Date Filing Date
GB4157659A Expired GB886091A (en) 1958-12-09 1959-12-07 Process for the production of methine dyestuffs
GB4178659A Expired GB888547A (en) 1958-12-09 1959-12-08 Dyeing and printing process

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB4178659A Expired GB888547A (en) 1958-12-09 1959-12-08 Dyeing and printing process

Country Status (6)

Country Link
BE (1) BE584028A (en)
CH (2) CH8093959D (en)
DE (1) DE1157582B (en)
FR (3) FR1244583A (en)
GB (2) GB886091A (en)
NL (1) NL246136A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3441563A (en) * 1958-08-22 1969-04-29 Bayer Ag Process for the production of substituted pyrazolones and of monomethine dyestuffs thereof
US4234677A (en) * 1978-01-26 1980-11-18 Ciba-Geigy Ag Pyrazolone dyestuffs and their use in photographic materials
CA1130130A (en) * 1979-03-02 1982-08-24 Raymond G. Lemahieu Photographic silver halide materials comprising a 2-pyrazolin-5-one pentamethine oxonol dye

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2840443A (en) * 1954-08-05 1958-06-24 Gen Aniline & Film Corp Use of methylidyne bis pyrazolones for dyeing

Also Published As

Publication number Publication date
FR1244583A (en) 1960-10-28
BE584028A (en)
CH8094059D (en)
FR1240930A (en) 1960-09-09
CH8093959D (en)
DE1157582B (en) 1963-11-21
NL246136A (en)
FR1242601A (en) 1960-09-30
GB888547A (en) 1962-01-31

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