Patent GB-919179-A (GB)
Title: New phthalocyanine dyes
Inventor: TARTTER ARNOLD
IPC: C09B62/457
Filed: 1960-10-14
Abstract: 1-Amino-4-chloro- or -bromo-butine-(2), 1-amino - 4 - chlorobutene - (2), 1-amino-3 : 4-dichlorobutene-(2) and 1-amino-2 : 3-dimethyl-4-bromobutene-(2) hydrochlorides are made by treating methanolic hydrogen chloride the reaction product of the appropriate dihalobutene or butine with hexamethylene tetramine. The hydrochlorides of 1-(4-aminophenoxy)-3 : 4-dichlorobutene-(2), 1-(4-aminophenoxy)-4-chlorobutine - (2), 1-aminobenzene-3-sulphonic acid-(3 : 4-dichlorobuten-(2)-ylamide) and of 1-aminobenzene-4-sulphonamide substituted in the amide group by 3 : 4-dichlorobuten-(2)-yl, 4-chlorobuten-(2)-yl and 4-chlorobutin-(2)-yl radicals are made by hydrolysis of the corresponding acetylamino compounds.  2-(4-chlorobutin - (2) - ylamino - (1))-4 : 6-dichloro-1 : 3 : 5-triazine is made by reacting cyanuric chloride with 1-amino-4-chlorobutine.  Benzene-1-sulphonic acid-(4-chlorobutin-(2)-ylamide)-3- and -4-carboxylic acid chlorides are made from the corresponding carboxylic acids prepared by reacting the corresponding benzoic acid sulphochloride with 1-amino-4- chlorobutine-(2). Specification 827,569 is referred to.ALSO:The invention comprises dyes of the formula:-(HO3S)n-(-Pc-)-(A-E-F)m where Pc is the radical of a metal-free or metalliferous phthalocyanine, or of a chlorphthalocyanine, phenylphahalocyanine, phenylmercaptophthalocyanine or phenylsulphonylphthalocyanine containing 1 to 4 chloro, phenyl, phenylmercapto or phenylsulphonyl radicals in the molecule and wherein the metal of the metalliferous derivatives is not lost by treatment with concentrated sulphuric acid at room temperature, A is one of the radicals -SO2-NH- <FORM:0919179/IV (b)/1> E is -CH2C=C-CH2 or CH2-C=C-CH2-, R1 and R2 are each hydrogen, chlorine, bromine or methyl, X is hydrogen or sulphonic acid, F is chlorine or bromine or one of the radicals -O-SO3H, <FORM:0919179/IV (b)/2> Q is a chlorine or bromine ion, n is 0-4 and m is 1-4.  The dyes are made by reacting a phthalocyanine amine of the formula:-(HO3S)n-(Pc)-(D)m with m mols of a compound Y-E-Z where Pc, E, n and m are as above, Z is chlorine, bromine or -OSO3H, D is -NH2, -CH2NH2, <FORM:0919179/IV (b)/3> or <FORM:0919179/IV (b)/4> and Y is chlorine or bromine or when D is <FORM:0919179/IV (b)/5> Y may also be <FORM:0919179/IV (b)/6> or <FORM:0919179/IV (b)/7> or by reacting a phthalocyanine sulphonchloride of the formula (Pc)-(SO2T)m + n with m mols of H2N-G-E-Z and hydrolysing the remaining sulphonchloride groups, where Pc, E, Z, m and n are as above, T is chlorine or bromine and G is a covalent linkage or <FORM:0919179/IV (b)/8> or <FORM:0919179/IV (b)/9> or by reacting a derivative of the formula (HO3S)n-(Pc)-(L-T)m with m mols of H2N-E-Z where Pc, T, E, Z, m and n are as above and L is <FORM:0919179/IV (b)/100> or <FORM:0919179/IV (b)/111> When Z in the above products is chlorine or bromine they may optionally be reacted with pyridine or tetramethylthiourea. Examples are given. The dyes dye and print textile materials of wool, silk, synthetic linear polyamides and leather, and dye and print natural or regenerated cellulose textile materials in conjunction with an alkali and heat treatment.  Specification 827,569 is referred to.