GB469748A - Improvements in the manufacture and production of polymethine dyestuffs - Google Patents

Improvements in the manufacture and production of polymethine dyestuffs

Info

Publication number
GB469748A
GB469748A GB284536A GB284536A GB469748A GB 469748 A GB469748 A GB 469748A GB 284536 A GB284536 A GB 284536A GB 284536 A GB284536 A GB 284536A GB 469748 A GB469748 A GB 469748A
Authority
GB
United Kingdom
Prior art keywords
aldehyde
methyl
condensed
ethyl
methylindoline
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
GB284536A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB284536A priority Critical patent/GB469748A/en
Priority to FR815168D priority patent/FR815168A/en
Publication of GB469748A publication Critical patent/GB469748A/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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
    • 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
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • 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
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Polymethine dyes are made by causing polynuclear heterocyclic nitrogen compounds containing an aldehyde group in p-position to the nitrogen atom in an aryl nucleus to react with compounds containing reactive methyl or methylene groups, e.g. 3-methyl-5-pyrazolones, quinaldine, 2-methyleneindolines, rhodanic acid, hydroxythionaphthenes, benzyl cyanide, cyanoacetic acid esters, omega-cyanoacetophenone, barbituric acid and malonic acid nitrile. They dye tannin-mordanted cotton and acetate artificial silk and the sulphonated products dye wool. Some may also be used to modify the sensitivity of photographic emulsions. In examples: (1), (2) 1 : 3 : 3-trimethyl-2-methyleneindoline is condensed with 2-methylindoline-5-aldehyde, 1 : 2 : 3 : 4-tetrahydroquinoline - 6 - aldehyde, N - b - cyanoethyl - 2 - methylindoline-5-aldehyde or N-b -cyanoethyl-1 : 2 : 3 : 4-tetrahydroquinoline-6-aldehyde; (3) 5 - methoxy - 1 : 3 : 3 - trimethyl - 2 - methyleneindoline is condensed with 1 : 2-dimethylindoline-5-aldehyde; (4), (5) 1-phenyl-3-methyl-5-pyrazolone is condensed with N-methyl or N - b - cyanoethyltetrahydroquinoline - 6 - aldehyde; (6) benzyl cyanide is condensed with 1 : 2 - dimethylindoline - 5 - aldehyde or 1-n-butyl - 2 - methylindoline - 5 - aldehyde; (7) quinaldine iodoethylate is condensed with N - ethyltetrahydroquinoline - 6 - aldehyde or 1-ethyl - 2 - methylindoline - 5 - aldehyde; (8) cyanoacetic acid ethyl ester is condensed with 2 - methylindoline - 5 - aldehyde, tetrahydroquinoline-6-aldehyde, 1 : 2-dimethyl, 1-ethyl-2-methyl-, 1-n-butyl-2-methyl-, 1-benzyl-2-methyl-, 1 - b - cyanoethyl - 2 - methyl-, and 1-b -chlorethyl-2-methyl-indoline-5-aldehyde, 1 : 2 : 3 : 3-tetramethylindoline-5-aldehyde, N-methyl-, N-ethyl-, N-n-butyl-, N-b -cyanoethyl-, and N - b - chlorethyl - tetrahydroquinoline - 6 aldehyde, and 1 : 2 : 3 : 4 : 10 : 11-hexahydrocarbazole-6-aldehyde; (9) omega-cyanoacetophenone is condensed with tetrahydroquinoline-6-aldehyde, 2-methyl-, 1 : 2-dimethyl- and 1-ethyl-2-methyl-indoline-5-aldehyde, and N-methyl-, N-ethyl-, N-n-butyl- and N-benzyltetrahydroquinoline - 6 - aldehyde; (10) 6-ethoxy-3-hydroxythionaphthene is condensed with 1 : 2-dimethylindoline-5-aldehyde; (11) rhodanic acid is condensed with N-b -cyanoethyl- or N-ethyl-tetrahydroquinoline-6-aldehyde and N-ethyl-2-methylindoline-5-aldehyde. Specifications 369,721, 378,239, 396,893, 399,387, and 466,723 are referred to. 5 - Methoxy - I : 3 : 3 - trimethyl - 2 - methyleneindoline is made by ring-closure of the p-methoxyphenylhydrazone of acetone and exhaustive methylation. Aldehydes.--N - n - butyltetrahydro - quinoline-6-aldehyde is made from N-n-butyltetrahydroquinoline and methylformylaniline in presence of phosphorus oxychloride. N-b -chlorethyl - tetrahydroquinoline - 6 - aldehyde are obtained similarly from N-b -chlorethyl-2-methylindoline and N-b -chlorethyltetrahydroquinoline. N - benzyltetrahydroquinoline - 6 - aldehyde is made similarly from N-benzyltetrahydroquinoline.
GB284536A 1936-01-30 1936-01-30 Improvements in the manufacture and production of polymethine dyestuffs Expired GB469748A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB284536A GB469748A (en) 1936-01-30 1936-01-30 Improvements in the manufacture and production of polymethine dyestuffs
FR815168D FR815168A (en) 1936-01-30 1936-12-18 Process for preparing polymethine dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB284536A GB469748A (en) 1936-01-30 1936-01-30 Improvements in the manufacture and production of polymethine dyestuffs

Publications (1)

Publication Number Publication Date
GB469748A true GB469748A (en) 1937-07-30

Family

ID=9747046

Family Applications (1)

Application Number Title Priority Date Filing Date
GB284536A Expired GB469748A (en) 1936-01-30 1936-01-30 Improvements in the manufacture and production of polymethine dyestuffs

Country Status (2)

Country Link
FR (1) FR815168A (en)
GB (1) GB469748A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2695289A (en) * 1950-03-09 1954-11-23 Bayer Ag Basic polymethine dyestuffs

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2695289A (en) * 1950-03-09 1954-11-23 Bayer Ag Basic polymethine dyestuffs

Also Published As

Publication number Publication date
FR815168A (en) 1937-07-07

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