Patent GB-929394-A (GB)
Title: Process for dyeing or printing synthetic polymers
IPC: C07D403/06
Filed: 1959-08-21
Abstract: Materials of synthetic polyamides, polyurethanes and aromatic polyesters are spun dyed using dyestuffs of the general formula <FORM:0929394/IV(a)/1> in which R is H, Cl or Br or a lower alkyl, lower alkoxy, b -hydroxy-ethoxy, amino, acetylamino, benzoylamino, nitro, cyano, sulphonamido, lower alkyl substituted sulphonamido, lower alkyl sulphonyl, lower alkyl sulphonylamino, phenyl sulphonylamino, phenyl, a carboxylic acid lower alkyl ester group or -CH=CH-CH=CH-which is linked to adjacent C-atoms of the carbocyclic nucleus, R2 is a hydrogen atom or a lower alkyl radical, R3 is H or lower alkyl, R4 is H or a cyano, acyl or carboxylic acid lower alkyl ester radical and R5 is a radical of the 5-pyrazolone series linked to the 4-position or a radical of cyanoacetic acid, cyanoacetic acid lower alkyl ester, cyanoacetic acid substituted lower alkyl ester such as a cyanoor hydroxy lower alkyl ester, cyanoacetic acid amide optionally substituted in the amide group bound in b -position to the >C=O group or malonic acid dinitrile, the radical R5 being free of sulphonic acid groups and the lower alkyl and lower alkoxy radicals containing 1-5 Catoms.  Specification 929,395 is referred to.ALSO:Materials of synthetic polyamides, polyurethanes and aromatic polyesters are dyed and printed using dyestuffs of the general formula <FORM:0929394/IV(a)/1> in which R is H, Cl or Br or a lower alkyl, lower alkoxy, b -hydroxy-ethoxy, amino, acetylamino, benzoylamino, nitro, cyano, sulphonamido, lower alkyl substituted sulphonamido, lower alkyl sulphonyl, lower alkyl sulphonylamino, phenyl sulphonylamino, phenyl, a carboxylic acid lower alkyl ester group or -CH=CH-CH=CH- which is linked to adjacent C-atoms of the carbocyclic nucleus, R2 is a hydrogen atom or a lower alkyl radical, R3 is H or lower alkyl, R4 is H or a cyano, acyl or carboxylic acid lower alkyl ester radical and R5 is a radical of the 5-pyrazolone series linked to the 4-position or a radical of cyanoacetic acid, cyanoacetic acid lower alkyl ester, cyanoacetic acid substituted lower alkyl ester such as a cyano- or hydroxy lower alkyl ester, cyanoacetic acid amide optionally substituted in the amide group bound in the a -position to the > C=O group or malonic acid dinitrile, the radical R5 being free of sulphonic acid groups and the lower alkyl and lower alkoxy radicals containing 1-5 C-atoms.  The dyestuffs may be applied from a fine aqueous dispersion using a formaldehyde-naphthalene sulphonic acid condensate as dispersing agent at temperatures of 60 DEG -100 DEG C. and are obtained as described in Specifications 929,393 and 929,395, by reacting the appropriate 2-methylene-indoline-o -aldehyde with a compound R5H2 or by reacting a 4-aldehyde-, 4-formyl- or 4-dimethylamino-5-pyrazolone with the appropriate 2-methylene-indoline.  The 5-pyrazolone may be substituted by 3-carboxylic acid ethyl ester or Na salt groups, 1-(31-chlorophenyl), 1-(31-nitrophenyl), 3-carboethoxy or 3-(p-methoxyphenyl) groups.  In the examples a large number of dyestuffs are employed to dye fibres of S -caprolactum, the reaction product of hexamethylene diisocyanate and 1,4-dibutylene glycol and, in the presence of o-cresotic acid methyl ester, fibres of polyethylene terephthalate.