GB467983A - Manufacture of methine and polymethine dyestuffs - Google Patents

Manufacture of methine and polymethine dyestuffs

Info

Publication number
GB467983A
GB467983A GB3557235A GB3557235A GB467983A GB 467983 A GB467983 A GB 467983A GB 3557235 A GB3557235 A GB 3557235A GB 3557235 A GB3557235 A GB 3557235A GB 467983 A GB467983 A GB 467983A
Authority
GB
United Kingdom
Prior art keywords
sulphoacetate
aniline
product
condensed
diphenylpyrylium
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
GB3557235A
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
Publication of GB467983A publication Critical patent/GB467983A/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
    • C09B23/0091—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
    • 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
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Abstract

Unsymmetrical methine and polymethine dyes of the pyridine series are made by causing an unsymmetrical methine or polymethine dye of the pyrylium series to react with ammonia or a primary amine. Suitable parent materials are compounds of the probable general formula <FORM:0467983/IV/1> in which R = alkyl or aryl which may be substituted, e.g. by nitro, halogen, alkyl, aryl, aralkyl, alkoxy, oxy, amino or substituted amino groups, R1 = aryl which may be substituted as above, R2 = H or an aromatic residue which may also be substituted as above, n = 0 or 1, X = an anion, e.g. halogen, ClO4, NO3, sulphoacetate or toluenesulphonate; R1 and R2 may also together form a ring, e.g. an indoline, quinoline or thiazole ring. Amines specified are methylamine, ethylamine, ethanolamine, aniline, phenetidines, toluidines, naphthylamines, p-dimethylaminoaniline, p-nitroaniline, halogen anilines. They dye silk and tannin-mordanted viscose artificial silk and mixed fabrics. In the examples: (1)--(3) 2 - b - (p : p<1> - tetramethyldiaminodiphenyl)-vinylene-4 : 6-diphenylpyrylium perchlorate is condensed with aniline, methylamine or p-nitroaniline and the corresponding sulphoacetate with methylamine; (4) 2-methyl-4 : 6-diphenylpyrylium sulphoacetate is condensed with cinnamic aldehyde in acetic anhydride and the perchlorate of the product is heated with aniline; (5) the sulphoacetate in (4) is condensed with the addition product of nitrosyl chloride to trimethylmethyleneindoline (Fischer's methylene base) in acetic anhydride and the product (sulphoacetate) heated with aniline; the perchlorate of the first condensation product is also described; (6) 2-methyl-4 : 6 - dianisylpyrylium sulphoacetate and o-or p-diethylaminobenzaldehyde are condensed in acetic anhydride and the perchlorate of the product is heated with aniline; (7) 2-methyl-4 : 6-diphenylpyrylium sulphoacetate is condensed as in (6) and the product heated with methylamine or aniline. The 2-b -(p : p<1>-tetramethyldiaminodiphenyl)-vinylene - 4 : 6 - diphenylpyrylium perchlorate used in example (1) is made by heating 2-methyl-4 : 6 - diphenylpyrylium sulphoacetate with Michler's ketone in presence of phosphorus oxychloride and treating a neutral solution of the product obtained with perchloric acid.
GB3557235A 1935-11-14 1935-12-23 Manufacture of methine and polymethine dyestuffs Expired GB467983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI53631D DE679986C (en) 1935-11-14 1935-11-14 Process for the preparation of asymmetrical methine dyes of the pyridine series containing one or three methine groups

Publications (1)

Publication Number Publication Date
GB467983A true GB467983A (en) 1937-06-23

Family

ID=10379217

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3557235A Expired GB467983A (en) 1935-11-14 1935-12-23 Manufacture of methine and polymethine dyestuffs

Country Status (3)

Country Link
DE (1) DE679986C (en)
FR (1) FR813442A (en)
GB (1) GB467983A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE959668C (en) * 1953-08-26 1957-03-07 Bayer Ag Process for the production of dyes

Also Published As

Publication number Publication date
DE679986C (en) 1939-08-21
FR813442A (en) 1937-06-01

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