Patent GB-1114936-A (GB)
Title: Process for mass coloring polyesters
Inventor: BOWMAN FRANCIS
IPC: C08L67/02
Filed: 1965-07-19
Abstract: Linear polyesters are mass-coloured by incorporating therein one or more dyes of the formula <FORM:1114936/C3/1> wherein D represents a di- or poly-cyclic dye-stuff radical free from sulphonic acid groups; Y represents a direct link or -NH-, -S- or -NHCO-; X represents a direct link or -O-, -S-, -NH-, -NR-, -CONH-, -CONR-, -SO2NH-, -SO2NR-, -CH2O-, -CH2NH- or -CH2NR-; A represents a hydroxy C1- 4 alkyl, dihydroxy C1- 4 alkyl, or hydroxy C1- 4 alkoxy C1- 4 alkyl group; and R represents C1- 4 alkyl or hydroxyalkyl group; m and n are each 1-4.  Preferred values for D are 11:91 - anthrapyridone, 11:91 - anthrapyrimidine, isothiazolanthrone, pyrazolanthrone, 31:41 - phthaloylacridone, phthaloyl perinone and, particularly, anthraquinone. The dye may be added before, during or after polymerization, e.g. to chips of the polyester, as a powder or in suspension in a volatile liquid, e.g. water or alcohol.  Suitable polyesters contain residues of terephtalic acid and a C2- 10 n-alkylene glycol or dimethylolcyclohexane, alone or with residues of other dicarboxylic acids or glycols or hydroxycarboxylic acids.  In examples the use of many dyes is illustrated, including dyes based on anthraquinone (Examples 1-81) and 31:41-phthaloylacridone, 11:91(N) - anthrapyridazone, 31:41 phthaloyl - thioxanthrone, indanthrone, pyranthrone, 11(N):91 - anthrapyridone, 11(N): 91-anthrapyridine, 11:91 - anthrapyrimidone, 11:21 - pyrazino - anthraquinone, 1 : 5 - di-anilino - anthraquinone, 2 - (anthraquinon - 11-ylamino) - 1:3:5 - triazine and phthaloperinone, and triphendioxazine (Examples 82-97).ALSO:Dyestuffs for mass coloration of polyesters have the general formula <FORM:1114936/C4-C5/1> wherein D represents a polycyclic dyestuff residue free of -SO3H groups; Y represents a direct link, or -NH-, -S- or -NHCO-; X represents a direct link or -O-, -S-, <FORM:1114936/C4-C5/2> or <FORM:1114936/C4-C5/3> R represents a C1-4 alkyl or hydroxyalkyl group; A represents a C1-4 hydroxyalkyl or dihydroxyalkyl or C1-4 hydroxyalkoxy C1-4 alkyl group; m and n each represent an integer of 1-4.  They may be prepared (a) by reacting a compound D(Hal)m (i) (where Hal = halogen) with the corresponding compound (ii) containing a group HY-; (b) by reacting a compound D(YH)m with the corresponding compound (ii) having halogen in place of HY-; (c) by treating with an amine A-NH2 or A-NHR a compound according to the general formula (A) above having -SO2Cl or -COCl in place of -X-A; (d) by reacting leuco-quinazarin with the corresponding compound (ii) having H2N- for HY-; (e) by reacting an aminoanthraquinone with a compound (ii) having -COCl for -YH; (f) by reacting with a compound A.Cl the compound of Formula (A) above having -NH2 in place of -X-A.  Of the many dyes illustrated, those in Examples 1-81 are based on anthraquinone, those in Examples 82-96 are based on 31:41-phthaloylacridone, 11:91(N) - anthrapyridazone, 31:41 - phthaloylthioxanthrone, indanthrone, pyranthrone, 11(N):91-anthrapyridone, 11(N):91-anthrapyridine, 11:91 - anthrapyrimidone, 11:21 - pyrazinoanthraquinone, 1:5-dianilinoanthraquinone, 2 - (anthraquinon - 11 -ylamino) - 1:3:5 - triazine, phthalopiperinone and triphendioxazine.