Patent GB-822047-A (GB)
Title: New dyestuffs containing a pyrimidine group and process for dyeing therewith
Inventor: HESLOP ROBERT NORMAN
IPC: C09B62/20
Filed: 1956-09-04
Abstract: The invention comprises as dyestuffs the 2:6 - dihalogeno - 4 - pyrimidylamino - or the 4:6 - dihalogeno - 2 - pyrimidylamino - derivatives of water-soluble coloured compounds, such as dyestuffs of the azo, anthraquinone, phthalocyanine or nitro series containing one or more water-solubilizing groups.  The dyestuffs are made by interacting 2:4:6-trihalogenopyrimidines with water-soluble coloured compounds containing at least one monosubstituted or unsubstituted amino group in such amounts as correspond to at least one molecular proportion of the 2:4:6-trihalogenopyrimidine for each mono-substituted or unsubstituted amino group and isolating the dihalogenopyrimidyl derivatives, or, when the dyestuffs contain one or more azo groups also by a coupling reaction wherein either the diazonium compound or the coupling component contains at last one 2:6-dihalogeno-4 - pyrimidylamino or 4:6-dihalogeno-2-pyrimidyl amino group.  The amino-containing water-soluble azo dyestuffs are made by coupling a diazotized aromatic mono- or diamine with 1 mol. of a coupling component or a tetrazotized aromatic diamine with 2 mols. of a coupling component or 1 mol. of each of two coupling components, at least one of the reactants containing at least one water-solubilizing group and the reactants being so selected that the product contains at least one monosubstituted or unsubstituted amino group.  The aromatic amines may also contain azo groups. The azo dyes are also made by hydrolysis of azo or polyazo compounds containing acylamino groups, which may be made by coupling aromatic amines and coupling components one or both of which contain acylamino groups, or by reduction of azo or polyazo compounds containing nitro groups.  The watersoluble anthraquinone dyestuffs described contain an unsubstituted or mono-substituted amino group in an alkylamino or arylamino group attached to an alpha-position of the anthraquinone nucleus and also contain at least one water-solubilizing group, and are made by reacting an alpha-halo or nitro-anthraquinone or the leuco derivative of a 1:4-dihydroxy-, -diamino- or -amino-hydroxy-anthraquinone with an aliphatic or aromatic diamine, or by sulphonating an amino-anthraquinone compound.  The water-soluble amino-phthalocyanine dyestuffs may contain the amino or mono-substituted amino group attached directly to the benz-ring of the phthalocyanine nucleus or through a divalent bridging group many of which are specified.  Those phthalocyanines containing sulphonic acid groups are made by sulphonating amino-phthalocyanines such as those described in Specifications 529,847, 569,200, 589,118, [all in Group IV], 717,137 and 724,212, or by synthesis from mixtures of sulphonated phthalic acids and substituted phthalic acid derivatives such as those described in Specifications 529,847, 569,200 and 589,118 and reducing nitro groups where necessary.  Those phthalocyamines containing a -CH2NRphenylene- or a -CH2NR-alkylene linkage where R is hydrogen, alkyl or cycloalkyl are made by reacting a phthalocyanine containing chlormethyl and sulphonic acid or carboxylic acid groups, made by chlormethylation of a phthalocyamine sulphonic or carboxylic acid, with respectively (i) a primary or secondary N-alkylor cycloalkylnitro-aniline and reducing the nitro groups, or (ii) a monoacetyl alkylene diamine and hydrolysing the acetylamino group; those containing -SO2NR-alkylene- or -SO2NR-phenylene-CH2-linkages are made by reacting phthalocyamines containing -SO2Cl groups with respectively monoacetyl alkylene diamines or amino-N-benzyl acetamides and hydrolysing the acetylamino groups; those containing -CONR-phenylene- or -CONRphenylene-CH2- linkages are made by reacting a phthalocyamine containing carboxylic acid chloride groups with, respectively, (i) diaminobenzene sulphonic or carboxylic acids or nitro-amino-benzene sulphonic or carboxylic acids and reducing the nitro group, or (ii) an N - (aminobenzyl) - acetamide and hydrolysing the acetylamino group.  The water-soluble nitro dyestuffs described are of the formula <FORM:0822047/IV(c)/1> where D is a naphthalene or benzene nucleus which may be further substituted and where N is ortho to the nitro group, X is hydrogen or a hydrocarbon radical which may be substituted, R is hydrogen or an organic radical attached to the nitrogen through a carbon atom, and where R may be connected to X when X is a hydrocarbon radical or to D, in the ortho position to N, to form a heterocyclic ring, the dyestuff containing at least one amino or monosubstituted amino group and at least one watersolubilizing group, and they are made by reacting an o-nitrochlorobenzene or naphthalene with the appropriate diamine.  The dyestuffs colour silk, wool, regenerated protein and cellulosic textile material such as cotton, linen and viscose rayon by treating the material with an aqueous solution or a thickened printing paste of the dyestuff in conjunction with a treatment with an acid-binding agent such as sodium hydroxide, sodium carbonate or potassium phosphate which may be carried out prior to, simultaneously with or after the dyestuff treatment.  The acid-binding agent may be replaced by a substance which on heating or steaming generates an acid-binding agent such as an alkali-metal bicarbonate or sodium trichloracetate.  The dyestuff solution may also contain sodium chloride, sulphate or alginate, urea and water-soluble alkyl ethers of cellulose.  The printing paste may also contain urea, methyl cellulose, starch, locust bean gum or sodium alginate.  The dyestuffs may also be applied to silk, wool, regenerated protein, polyamide and modified polyacrylonitrile textile materials by conventional dyeing methods.  Dyestuff pastes comprising dyestuffs of the invention and buffers suitable for maintaining a pH of about 6.5 such as mixtures of sodium dihydrogen phosphate and disodium hydrogen phosphate or of disodium hydrogen phosphate and potassium dihydrogen phosphate are described.  Examples are given. Specifications 307,947, [Class 2 (iii)], 467,815, 503,609 and 515,637, [all in Group IV], also are referred to.