Patent GB-983369-A (GB)
Title: Phthalocyanine dyestuffs
Inventor: POOLE VICTOR DAVID
IPC: C09B62/036
Filed: 1962-05-15
Abstract: The invention comprises dyes which, in the form of their free acids, have the formula <FORM:0983369/C4-C5/1> where Pc is a phthalocyanine radical, D1 and D2 are each hydrogen, alkyl or hydroxyalkyl of 1 to 4 carbon atoms or sulphoethyl, R1 and R2 are each methyl and R3 and R4 are each hydrogen, R1 and R2 are joined together to form a tetramethylene or pentamethylene radical, or R1 and R3 and R2 and R4 are joined to form in each case a trimethylene radical, X is a divalent monochloropyrimidine, dichloropyrimidine radical or a divalent 1 : 3 : 5-triazine radical substituted in the 6-position by hydrogen, an alkyl or alkoxy group of 1 to 4 carbon atoms phenyl, phenoxy, amino or a substituted amino group, L is a group of the formula <FORM:0983369/C4-C5/2> or <FORM:0983369/C4-C5/3> where R is hydrogen or alkyl of 1 to 4 carbon atoms, A is a sulphonated or unsulphonated 1 : 3- or 1 : 4-phenylene radical or an alkylene radical of 2 to 6 carbon atoms, a has a value of from 1 to 3, b has a value of from 1 to 2 and c has a value of from 0 to 2 provided that a+b+c does not exceed 4. Each of the sulphonic acid and sulphonamide groups in the above formula is directly attached to a carbon atom in the 3- or 4-position of the benz rings of the phthalocyanine.  The dyes are mixtures and a, b and c are statistical values. The dyes are made by reacting a compound of the formula <FORM:0983369/C4-C5/4> with a hydrazine of the formula <FORM:0983369/C4-C5/5> or, when the substituent in the 6-position of the triazine ring is amino or substituted amino, by condensing a compound of the formula <FORM:0983369/C4-C5/6> with cyanuric chloride and replacing one of the two remaining chlorine atoms by reaction with ammonia or a primary or secondary amine.  The dyes dye and print cellulose textile material preferably in conjunction with an acid-binding agent or a substance which yields such an agent on heating or steaming.  The Provisional Specification also relates to dyes of the above general formula wherein D1 and D2 may be hydrogen, a substituted or unsubstituted hydrocarbon radical including aryl or may be joined together to form a heterocyclic ring, wherein L may also be a group -NH-A-O- or -NH-A-S- and A may be a substituted or unsubstituted alkylene or arylene radial, wherein the triazine or pyrimidine ring may carry a hydrogen, chlorine, bromine, alkyl, aryl or substituted or unsubstituted hydroxy, mercapto or amino substituent, wherein the hydrazinium group in the above general formula may be replaced by a group of the formula <FORM:0983369/C4-C5/7> wherein X is direct link or a <FORM:0983369/C4-C5/8> or <FORM:0983369/C4-C5/9> group, where Y is O, S or NR7, W is a divalent bridging group such as alkylene, arylene, diacyl or alkylene-carbonyl or arylenecarbonyl, R1 and R2 are each substituted or unsubstituted hydrocarbon radicals, R3 and R4 are each hydrogen, substituted or unsubstituted hydrocarbon radicals, acyl radicals or sulphonic acid or dithiocarboxylic acid groups or R3 and R4 together are substituted or unsubstituted alkylidene or arylidene groups or at least two of R1, R2, R3 and R4 form with one or both nitrogen atoms one or more heterocyclic rings and R5, R6 and R7 are each hydrogen or substituted or unsubstituted hydrocarbon radicals and wherein a has a value from 0 to 3, b has a value from 1 to 3 and c has a value from 0 to 2, provided that a+b+c does not exceed 4 and that when a is less than 0.5 at least one of D1 and D2 is hydrogen or at least one of D1, D2 and A contains a sulphonic acid or sulphate ester group.  The dyes may also be made by reacting an appropriate intermediate with a phthalocyanine sulphonic acid sulphochloride. Lists of starting materials for making these dyes are given. Specifications 805,562, 822,047, 836,647 and 866,513 are referred to.