Patent GB-587929-A (GB)
Title: Compositions containing diazotizable amines or diazonium salts thereof
IPC: D06P1/12
Filed: 1943-03-10
Abstract: Azo dyes, forming on the material; printing.-A diazotizable amine free from water-solubilizing groups or a water-soluble diazonium salt derived therefrom is incorporated with at least one ester derived from an organic di- or tri-basic carboxylic, sulphonic or sulphocarboxylic acid free from olefinic double or acetylenic triple bonds and an alcohol containing at least one olefinic double bond or acetylenic triple bond or with a water-soluble salt of such an ester still containing an acidic group, other than a salt with a nitrogenous base having one or more olefinic or acetylenic bonds, to provide a composition for use in textile printing, the ester or its salt being in sufficient amount to inhibit thinning of a printing paste containing a carbohydrate thickener.  The ester must be free from constituents capable of azoic coupling or of catalytically decomposing diazonium salts at room temperature, and when added to the amine before diazotization it must be free from diazotizable amino groups.  A large number of diazotizable amines is specified. Specified esters are those derived, on the one hand, from oxalic, malonic, succinic, chlorosuccinic, malic, tartaric, tricarballylic, citric, mesoxalic, mucic, thiodiglycollic, sulphoacetic, sulphosuccinic, hexahydrophthalic, phthalic, trimesic, benzenedisulphonic, m-sulphobenzoic, sulphonaphthoic and quinolinic acids and, on the other hand, from vinyl or allyl alcohol, 2-methyl-2-propenol, 2 - butenol, 1 : 1 - dimethyl - 2 - propenol, 3 : 3 - diethyl - 2 - propenol - 1, 9 - octadecenol, 1 : 6 - heptadienol-4 3 : 7-dimethyl-2 : 6-octadienol-1, propargyl alcohol, terpineols, isopulegol and cinnamyl alcohol, and such esters are exemplified by diallyl oxalate, monoallyl succinate, monoallyl tartrate, a -allyl tricarballylate, monoallyl citrate, diallyl mucate, allyl sulphoacetate, sulphodiallyl and sulphodimethallyl succinates, allyl hexahydrophthalate, allyl m - sulpho - benzoate and allyl quinolinate.  The esters containing an acidic group may be in the form of their sodium, potassium, zinc, calcium or ammonium salts or their salts with organic bases such as amines, amidines or guanidines.  In examples: (1) a paste for printing on cloth impregnated with ice colour coupling components such as 2 : 3-hydroxynaphthoic arylides contains the zinc chloride double salt of the diazonium chloride from p  2-nitro-4-methoxyaniline, aluminium sulphate, monoallyl succinate and Carob bean gum; (2) the aluminium sulphate in (1) is omitted and the Carob bean gum is replaced by gum tragacanth or methyl cellulose; (3) pastes yielding yellowish scarlet, reddish scarlet and navy blue prints respectively on cotton cloth impregnated with 2 : 3-hydroxynaphthoic anilide contain monoallyl succinate, Carob bean gum and the zinc chloride double salts of the diazonium (or tetrazonium) chlorides from 2 : 5-dichloraniline, 2-methoxy-5-nitroaniline or o-dianisidine; (4) pastes yielding Bordeaux, yellowish scarlet and reddish scarlet prints respectively on cloth impregnated with 2 : 3-hydroxynaphthoic anilide contain diallyl sodium sulphosuccinate, Carob bean gum and the zinc chloride double salts of the diazonium chlorides from 2-nitro-4-methoxyaniline, 2 : 5 - dichloraniline or 2 - methoxy-5-nitroaniline.  Specification 446,568 is referred to. Monoallyl succinate is obtainable by refluxing equimolecular proportions of succinic anhydride and allyl alcohol in the presence of pyridine.  Diallyl and dimethallyl sodium sulphosuccinates are obtainable by the action of sodium bisulphite on diallyl and dimethallyl maleates, themselves prepared by refluxing maleic anhydride with excess of allyl or a - or b -methallyl alcohol in the presence of sulphuric acid.  Monoallyl tartrate is obtainable in the form of its potassium salt by refluxing diallyl tartrate with a solution of potassium hydroxide in allyl alcohol.  a -Allyl tricarballylate is obtainable by heating the a  : b -anhydro-acid with allyl alcohol.  Monoallyl citrate is obtainable by heating together equimolecular proportions of citric acid and allyl alcohol in an autoclave.  Diallyl mucate is obtainable by refluxing mucic acid with excess of allyl alcohol in the presence of hydrogen chloride.  Monoallyl sulphoacetate is obtainable by warming together equimolecular proportions of allyl chloracetate and potassium sulphite in aqueous allyl alcohol.  Monoallyl hexahydrophthalate is obtainable by heating hexahydrophthalic anhydride with an equimolecular proportion of allyl alcohol.  Monoallyl m-sulphobenzoate is obtainable by heating the acid with allyl alcohol in the presence of hydrogen chloride.  Monoallyl quinolinate is obtainable by refluxing quinolinic anhydride with allyl alcohol.