Patent GB-942569-A (GB)
Title: New water-soluble dyes of the phthalocyanine series which contain methylene ether radicals
Inventor: TARTTER ARNOLD
IPC: D06P3/60
Filed: 1960-10-14
Abstract: The invention comprises water-soluble dyes of the formula (HO3S)n-(Pc)-(SO2-NH-Z)m wherein Pc is a metalliferous or metal-free phthalocyanine radical, Z is one of the radicals <FORM:0942569/C3/1> <FORM:0942569/C3/2> <FORM:0942569/C3/3> and -L-M in which X is hydrogen, halogen, alkyl, alkoxy or sulphonic acid, Y is hydrogen or sulphonic acid, A is a covalent linkage, -NH- or -SO2NH-, L is a covalent linkage or a radical of the formula <FORM:0942569/C3/4> M is hydrogen, <FORM:0942569/C3/5> or <FORM:0942569/C3/6> and Q is hydrogen or sulphonic acid, and in the radical Z all the hydrogen atoms reactable with formaldehyde have been replaced by groups of the formula -CH2OR where R is an aliphatic or araliphatic radical and n and m are each 1, 2, 3 or 4 and their sum is 3, 4, 5 or 6.  The dyes are made by treating with an alcohol in the presence of a mineral acid or an acid-reacting substance a dye of the above formula wherein the hydrogen atoms reactable with formaldehyde have been replaced by the groups -CH2OH, or by transetherifying a dye of the above formula where R is a low molecular weight such as methyl with alcohols of higher molecular weight such as butyl, benzyl or nonyl alcohols in the presence of catalytic amounts of hydrochloric acid. Examples are given.  The dyes dye and print textile materials of wool, silk, synthetic linear polyamides and polyurethanes, polyvinyl alcohol, cellulose esters and cellulose. Specifications 895,029, 908,301 and 942,555 are referred to.ALSO:Textile materials of wool, silk, synthetic linear polyamides or polyurethanes, polyvinyl alcohol, cellulose esters and cellulose are dyed or printed, if desired in conjunction with a resin finishing treatment, with water-soluble dyes of the formula:  (HO3S)n-(Pc)-(SO2-NH-Z)m where Pc is a metalliferous or metal-free phthalocyanine radical, Z is one of the radicals:- <FORM:0942569/D1-D2/1> and <FORM:0942569/D1-D2/2> and -L-M, in which X is hydrogen, halogen, alkyl, alkoxy or sulphonic acid, Y is hydrogen or sulphonic acid, A is a covalent linkage, -NH- or -SO2NH-,L is a covalent linkage or a radical of the formula: <FORM:0942569/D1-D2/3> M is hydrogen,-CONH2, <FORM:0942569/D1-D2/4> or <FORM:0942569/D1-D2/5> and Q is hydrogen or sulphonic acid, and in the radical Z all the hydrogen atoms reactable with formaldehyde have been replaced by groups of the formula: -CH2OR where R is an aliphatic or araliphatic radical and n and m are each 1, 2, 3 or 4 and their sum is 3, 4, 5 or 6.  The dyes may be applied to cellulose material in conjunction with a treatment with acid-reacting substances and an optional heat treatment.  The dyes may also be applied to textile materials together with acid-reacting substances and hardenable aminoplasts and, if desired, aldehydes, and the material then heat-treated to effect simultaneous dyeing and resin-finishing.  Amino-plasts specified are dimethylol-urea, dimethyldimethylol-urea, dimethylol-dicyandiamide, methylol-thiourea, dimethylol-guanidine, trimethylol melamine, diphenyl-dimethylol-urea, butane-diol diurethane and N:N1-dimethylol-glyoxal monoureine. Acid-reacting substances mentioned are boric phosphoric, formic, acetic, glycolic, maleic, chloracetic, chlorproprionic, citric and malic acids, ammonium nitrate and chloride, monoammonium phosphate, zinc and magnesium chloride and diethanolamine hydrochloride. Aldehydes which may be used are acetaldehyde, glyoxal and formaldehyde which may be in the form of paraformaldehyde or hexamethylene tetramine.  In examples, cotton fabric is padded with an aqueous dyestuff solution containing (1) and (7) ammonium nitrate, or (2) and (6) N:N1-dimethylol-glyoxalmonoureine and zinc chloride, or (3) N:N1-dimethylol-glyoxalmonoureine and ammonium nitrate and the fabric is then heat treated. Specifications 895,029, 908,301 and 942,555 are referred to.