Patent GB-587928-A (GB)
Title: Compositions containing diazotizable amines or diazonium salts thereof
IPC: D06P1/62
Filed: 1943-03-10
Abstract: Azo dyes, forming on the material; printing.-A diazotisable amine free from water-solubilizing groups or a water-soluble diazonium salt derived therefrom is incorporated with at least one water-soluble organic sulphonic acid containing not more than 15 carbon atoms and at least one olefinic double bond or acetylenic triple bond, otherwise than as part of an ester group, or with a water-soluble salt thereof, other than a salt with a base having one or more olefinic or acetylenic bonds, to provide a composition for use in textile printing, the acid or its salt being in sufficient amount to inhibit thinning of a printing paste containing a carbohydrate thickener.  The acid or salt must be free from constituents capable of azoic coupling or of catalytically decomposing diazonium salts at room temperature, and if incorporated before diazotization it must be free from diazotizable amino groups.  A large number of diazotizable amines is specified.  Specified sulphonic acids are ethylenesulphonic, 2-propene-1-sulphonic, 2-methyl-2-propene-1-sulphonic, 2-butene-1-sulphonic, 1 : 1-dimethyl-2-propene-1-sulphonic, 3 : 3-diethyl-2-propene-1-sulphonic, 1 : 6-heptadiene-4-sulphonic, 3 : 7-dimethyl-2 : 6-octadiene-1-sulphonic, 2-propine-1 - sulphonic, cyclohexene - 3 - sulphonic, 1 - p - menthene-4- or 8-sulphonic, styrene-b -sulphonic and a -methylstyrene-p-sulphonic acids, the allyl ethers of phenol-p-sulphonic, 1 : 4-naphthol-sulphonic 2 : 6 : 8-naphtholdisulphonic, 4-nitrophenol-2-sulphonic, 4-chlorophenol-2-sulphonic and 4-aminophenol-2-sulphonic acids, and N-allyl-raurine.  In examples: (1) the zinc chloride double salt with 2-nitro-4-methoxybenzenediazonium chloride is incorporated with sodium 2 - propene - 1 - sulphonate, magnesium sulphate, carob bean gum and water to provide a paste for printing on cotton fabric impregnated with the anilide of 2 : 3-hydroxynaphthoic acid or the o-tolidide of acetoacetic acid; (2) the sodium 2-propene-1-sulphonate in (1) is replaced by sodium 2-methyl-2-propene-1-sulphonate, while the diazonium chloride may be replaced by that derived from 5-nitro-2-methoxyaniline, 2 : 5-dichloroaniline or dianisidine, the magnesium sulphate may be omitted and the carob bean gum may be replaced by methylcellulose; (3) 2 - nitro - 4 - methoxyaniline, 4 - nitro - 2 - methoxyaniline or 4-chloro-2-nitroaniline is incorporated with sodium 2-methyl-2-propene-1-sulphonate and sodium chloride and the mixture is treated with hydrochloric acid and sodium nitrite to prepare a diazo solution to which are added sodium acetate and carob bean gum to provide a paste for printing on a textile material impregnated with an arylide of 2 : 3-hydroxynaphthoic acid; (4) the zinc chloride double salt with the tetrazonium chloride from dianisidine is incorporated with potassium 2-methyl-2-propene-1-sulphonate, carob bean gum and water to provide a paste for printing on cellulosic material impregnated with an arylide of 2 : 3-hydroxynaphthoic acid; (5) and (6), the zinc chloride double salt with 2-nitro-4-methoxybenzenediazonium chloride is incorporated with (5) the allyl ether sodium phenol-p-sulphonate; (6) ammonium styrene-b -sulphonate and hydrochloric acid, and with carob bean gum and water to provide a printing paste.  2 - Propene - 1 - sulphonic acid, 2 - methyl - 2 - propene-1-sulphonic acid, 2-butene-1-sulphonic acid, 1 : 1-dimethyl-2-propene-1-sulphonic acid, 3 : 3-diethyl-2-propene-1-sulphonic acid, 1 : 6-heptadiene-4-sulphonic acid, 3 : 7-dimethyl-2 : 6-octadiene-1-sulphonic acid, 2-propine-1-sulphonic acid and 1-p-menthene-4- and 8-sulphonic acids are obtained by the action of sodium sulphite on the corresponding chloride or bromide.  The allyl ethers of phenol-p-sulphonic, 1 : 4-naphtholsulphonic and 2 : 6 : 8-naphtholdisulphonic acids are obtained by the action of allyl bromide on the acids in an alkaline medium.  The allyl ethers of 4-nitrophenol-2-sulphonic, 4-chlorophenol-2-sulphonic and 4-aminophenol-2-sulphonic acids are obtained by treating the sodium phenolate salts with an allyl halide.  4-Aminophenol-2-sulphonic acid is obtained by reduction of 4-nitrophenol-2-sulphonic acid.  The Specification as open to inspection under Sect. 91 comprises also the use of 9-octadecene-1-sulphonic acid, diallyl and dimethallyl sulphosuccinates (obtainable from the corresponding maleic esters by the action of sodium bisulphite) and phenylacetylene-p-sulphonic acid.  This subject-matter does not appear in the Specification as accepted.