Patent GB-1111895-A (GB)
Title: Process for the mass coloration of polyesters
Inventor: COOPER ALBERT CHARLES
IPC: C09B5/00
Filed: 1966-03-17
Abstract: Linear polyesters are dyed with a dyestuff of the formula D-(NHCO-X-COOR)n where D represents a polycyclic dyestuff radical containing at least 3 condensed rings and free from sulphonic acid groups, X represents an ethylene or 1:3- or 1:4-phenylene group, R represents H or an alkyl, hydroxyalkyl, dihydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl group. Preferred values of D are 11:91-anthrapyridone, 11:91-anthrapyrimidine, isothiazolanthrone, pyrazolanthrone, 31:41-phthaloylacridone, phthaloylperinone and, particularly, anthraquinone dyestuff radicals.  Suitable polyesters contain residues of terephthalic acid and a C2- 10 n-alkylene glycol or dimethylolcyclohexane, of which a part may be replaced by other dicarboxylic or hydroxycarboxylic acid or different glycol residues. The dye may be incorporated by addition to the starting materials or to the partly polymerized reaction mixture, or by mixing in finely divided form or as a dispersion in a volatile liquid, e.g. water or alcohol with the solid polymer (e.g. as chips) then melting and spinning or shaping the mixture.  In examples polyethylene terephthalate chips or granules are tumbled with the following dyes in powder form or in suspension in b -ethoxyethanol, then dried if necessary, and melt spun: 1:5-bis(p-carboxybenzoylamino) anthraquinone, 1 - (p-carboxybenzoylamino)anthraquinone, 6 - (p-carboxybenzoylamino) - 31:41 - phthaloylacridone, 1 - (p - carboxybenzoylamino) - 4-anilinoanthraquinone, 1 - (m - carboxybenzoylamino) - 4 - anilinoanthraquinone, 1 - (p-carboxybenzoylamino) - 4 - (21:41:61 - trimethylanilino)anthraquinone, 1 - (m - carboxybenzoylamino) - 5 - amino - 4:8 - dihydroxyanthraquinone, 1 - [p - (b  - carboxypropionylamino)anilino] - 4 - hydroxyanthraquinone, 1:5 - bis[41 - (p - carboxybenzoylamino) anilino]-anthraquinone, bis - (b - ethoxyethyl) ester and bis - (b  - hydroxyethyl) ester of 1:5 - bis - (p-carboxybenzoylamino)anthraquinone, b :g  - dihydroxypropyl ester of 1-(p-carboxybenzoylamino) - 4 - mesidinoanthraquinone, b  - hydroxyethyl ester of 1-(p-carboxybenzoylamino)-4 - anilinoanthraquinone, b  - (b 1 - hydroxyethoxy) - ethyl ester of 1 - (p - carboxybenzoylamino)anthraquinone and 1-[41-(p-carboxybenzoylamino) - anilino] - 4 - hydroxyanthraquinone. In Example 18 1:5-bis(p-carbomethoxybenzoylamino)anthraquinone is added to the transesterification product of dimethyl terephthalate and ethylene glycol before this is polycondensed.ALSO:Anthraquinone and acridone dyestuffs containing 1 or 2 groups -NHCO-C6H4-COOR or -NHCO-C2H4-COOR, where R represents H or a b -hydroxy-ethyl, b -ethoxy-ethyl, b (b 1 - hydroxyethoxy)ethyl, or b ,g  - dihydroxypropyl group, may be prepared by reacting 1:5 - or 1:8 - diaminoanthraquinone, 1-aminoanthraquinone, 6 - amino - 31:41-phthaloylacridone, 1 - amino - 4 - anilinoanthraquinone, 1 - amino - 4 - (21:41:61 - trimethylanilino) anthraquinone, 1:5 - diamino-4:8 - dihydroxyanthraquinone or 1 - hydroxy-4 - (p - aminoanilino) anthraquinone with isophthaloyl chloride, terephthaloyl chloride or succinic anhydride i.p.o. pyridine and hydrolysing the product or treating it with ethylene glycol, ethoxyethanol, diethylene glycol or glycerol.