GB463042A - Improvements in the manufacture and production of dyestuffs - Google Patents

Improvements in the manufacture and production of dyestuffs

Info

Publication number
GB463042A
GB463042A GB2562535A GB2562535A GB463042A GB 463042 A GB463042 A GB 463042A GB 2562535 A GB2562535 A GB 2562535A GB 2562535 A GB2562535 A GB 2562535A GB 463042 A GB463042 A GB 463042A
Authority
GB
United Kingdom
Prior art keywords
aldehyde
methyleneindoline
trimethyl
condensing
group
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
GB2562535A
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 GB2562535A priority Critical patent/GB463042A/en
Publication of GB463042A publication Critical patent/GB463042A/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
    • C09B23/14—Styryl dyes
    • 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

Abstract

Polymethine dyes are prepared by condensing nitriles of the general formula <FORM:0463042/IV/1> or substitution or saponification products thereof (wherein R is hydrogen or an alkyl, oxyalkyl or aralkyl radicle) which are free from further primary or secondary amino groups with 2-methyleneindoline-w-aldehydes, or by condensing a nitrile of the general formula above or a substitution or saponification product thereof which is substituted by the aldehyde group in p-position with reference to the amino group with a compound containing a reactive methylene group which is capable of condensing with one aldehyde group with splitting off of one molecular proportion of water and formation of a carbon-carbon double linkage. The dyes derived from an indoline are generally water-soluble and suitable for dyeing tannin-mordanted cotton and acetate artificial silk; the dyes derived from compounds having a reactive methylene group such as cyanacetic esters or anilides, malonic acid dinitrile or acetoacetic arylides are water-insoluble dyes suitable for dyeing acetate artificial silk. In examples: (a) N-ethyl-N-phenyl - b - aminopropionitrile is treated in benzene in presence of phosphorus oxychloride with 1.3.3-trimethyl-2-methyleneindoline-w-aldehyde (the nitrile group in the dye may be subsequently saponified) and with 5-methoxy-1.3.3-trimethyl-2-methyleneindoline-w-aldehyde; (b) N-benzyl-N-phenyl-b -aminopropionitrile is treated in benzene in presence of phosphorus oxychloride with 5-methoxy - 1.3.3 - trimethyl - 2 - methyleneindolene - w - aldehyde: (c) N - methyl - N-b -propionitrile-p-aminobenzaldehyde (prepared by condensing N-methyl-N-phenyl-b -aminopropionitrile with methylformanilide and phosphorus oxychloride) is condensed with 5-methoxy-1.3.3-trimethyl-2-methyleneindoline in glacial acetic acid, and with cyanoacetic acid ethyl ester in ethyl alcohol in presence of piperidine: (d) N-ethyl-N-b -propionitrile-p-aminobenzaldehyde is condensed with cyanoacetic acid ethyl ester in alcohol in presence of piperidine. Specification 441,389 is referred to.
GB2562535A 1935-09-16 1935-09-16 Improvements in the manufacture and production of dyestuffs Expired GB463042A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2562535A GB463042A (en) 1935-09-16 1935-09-16 Improvements in the manufacture and production of dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2562535A GB463042A (en) 1935-09-16 1935-09-16 Improvements in the manufacture and production of dyestuffs

Publications (1)

Publication Number Publication Date
GB463042A true GB463042A (en) 1937-03-16

Family

ID=10230683

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2562535A Expired GB463042A (en) 1935-09-16 1935-09-16 Improvements in the manufacture and production of dyestuffs

Country Status (1)

Country Link
GB (1) GB463042A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE742039C (en) * 1938-07-29 1943-12-10 Ig Farbenindustrie Ag Process for the production of water-soluble basic dyes
DE744019C (en) * 1939-11-27 1944-01-11 Ig Farbenindustrie Ag Process for the production of violet to blue water-soluble basic dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE742039C (en) * 1938-07-29 1943-12-10 Ig Farbenindustrie Ag Process for the production of water-soluble basic dyes
DE744019C (en) * 1939-11-27 1944-01-11 Ig Farbenindustrie Ag Process for the production of violet to blue water-soluble basic dyes

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