Patent GB-580641-A (GB)
Title: Manufacture of new derivatives of sulphonated amines or sulphonated aryl-hydrazines
IPC: C07C309/47
Filed: 1943-03-19
Abstract: Derivatives of sulphonated amines or arylhydrazines for use either alone or with, for example, inorganic salts as textile assistants such as wetting, dispersing, washing, softening, levelling or foaming agents, are prepared by reaction of a sulphonated amine or sulphonated aryl-hydrazine with a chlormethyl-, especially 2-chlormethyl-cymene at a raised temperature and/or in presence of an acid-binding agent. Sulphonated amines include sulphuric acid esters of hydroxyamines. Suitable amino-sulphonic acids are taurine and methylaminoethane sulphonic acid and, preferably, aromatic amino-sulphonic acids, e.g. sulphanilic acid, N-monoethylsulphanilic acid, metanilic acid, 1-amino-benzene-disulphonic acid-(2.4), halogenated aniline sulphonic acids, sulphonic acids of toluidine and xylidine, 1.2-diamino-benzene sulphonic acid-(4), aminocymene sulphonic acids, sulphonic acids of naphthylamine such as naphthionic acid, 1.6- or 2.6-naphthylamine sulphonic acid, 2.6.8-naphthylamine disulphonic or 2.3.6.8-naphthylamine trisulphonic acid, 1 - amino - tetrahydronaphthalene - 4 - sulphonic or 2.4-disulphonic acid, aminosulphonic acids of diphenyl, sulphonic acids of benzidine or dianisidine, and aminosulphonic acids of anthracene, phenanthrene or acenaphthene.  These may contain such substituents as halogen or hydroxy groups.  Carbazole sulphonic acids are examples of heterocyclic aminosulphonic acids.  Sulphonated aryl-hydrazines include phenyl-hydrazine-parasulphonic acid and 2-hydrazino-naphthalene-disulphonic acid-(6.8).  The amino or hydrazine groups may be primary or secondary.  Ethanolamine sulphuric acid ester is an example of an ester of a hydroxy-amine. The chlormethyl-cymene may be reacted with an aqueous solution of the neutralized aminosulphonic acid at 60-70 DEG  C., sodium carbonate being added to maintain the solution alkaline.  When b -aminoethane sulphonic acid is used, it is advantageous to work in presence of a mixture of water and a water-soluble solvent, e.g. aqueous methanol. In examples: (1) 2-chlormethyl-cymene is slowly added to N-methylsulphanilic acid at 65-70 DEG  C., alkalinity being maintained by addition of sodium carbonate.  Sodium N-methyl - N - cymyl - methylsulphanilate is obtained.  Sodium N-cymyl-methyl-metanilate is produced in analogous manner; (2) the monopotassium salt of 2.6.8-naphthylamine disulphonic acid is similarly converted to sodium 2-di-(or mono-) cymyl-methyl-naphthylamine disulphonate; (3) and (4) sodium phenyl-hydrazine sulphonate similarly yields sodium N-cymylmethyl- (or di-cymylmethyl-) phenyl-hydrazine sulphonate. Nuclear halogenated acids, and naphthyl-hydrazine sulphonic acids give similar products; (5) sodium-b -amino-ethane sulphonate is refluxed with aqueous methanol or dioxane and 2-chlormethyl-cymene to yield sodium-b -mono- (or di) cymyl-methylamino-ethane sulphonate.  The Specification as open to inspection under Sect. 91 comprises also the treatment of the reaction products with alkylating or acylating agents.  An unsulphonated amine may be reacted with the chlormethyl-cymene and the product sulphonated, if desired before or after treatment with an alkylating or acylating agent. Products containing a secondary amino group may be further substituted by the action of alkylating agents such as ethylene oxide, glycide or epichlorhydrin or acylating agents such as acetic anhydride or butyric, caproic, lauric or stearic acid chloride.  Excess of 1.2-alkylene oxide may introduce polyglycol ether residues.  This subject-matter does not appear in the Specification as accepted.