Azo dyestuffs containing a cinnamonitrile residue

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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106308Q, 208 12, 260 37R, 260 38, 260 39P, 260 40R, 260 4221, 260152, 260154, 260155, 260159, 260162, 260163, 260176, 260184, 260193, 260197, 260205, 260206, 260207, 2602071, 2602075, 260465E, 260465G, 260465K, C09B 2908, C09B 2910, C09B 2926, C09B 2928

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040082130

ABSTRACT:
Dyestuffs of the general formula: ##STR1## in which the radical --CH=CH--CN is fixed in the 4- or 5- position, X represents a hydrogen or chlorine atom, the benzene nucleus A is unsubstituted or substituted by at least one chlorine atom or alkyl, alkoxy or acylamino group, m is the number 0 or 1, and B represents the residue of a coupling compound containing no sulphonic or carboxylic acid group.
The dyestuffs in which m represents zero may be prepared by diazotizing a base of the formula: ##STR2## and coupling the diazo derivative with a coupling compound BH wherein X and B have the same significance as set out above.
The dyestuffs in which m is equal to 1 may be prepared by coupling the diazo derivative of a base of the formula: ##STR3## with an amine of the formula: ##STR4## diazotizing the amino-monoazo dyestuff thus obtained and coupling with a coupling compound BH wherein ##STR5## have the same significance as set out above. The dyestuffs may be used for the coloration of synthetic fibers such as fibers based on cellulose diacetate, cellulose triacetate and, more particularly aromatic polyesters and polyamides.
3-amino-cinnamonitrile or 3-amino-4-chloro-cinnamonitrile or 4-amino-3-chloro-cinnamonitrile. These may be prepared by Meerwein's reaction between acrylonitrile and a diazonium chloride of m- or p-nitraniline, dehydrohalogenation by means of an alkali and then reduction of the nitro group.

REFERENCES:
patent: 3090780 (1963-05-01), Gaetani
patent: 3222355 (1965-12-01), Gaetani
patent: 3578654 (1971-05-01), Favre

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