Patent GB-530883-A (GB)
Abstract: 530,883. Dyeing textiles. SOC. OF CHEMICAL INDUSTRY IN BASLE. June 22, 1939, Nos. 18201 and 18202. Convention dates, June 22, 1938 and June 13, 1939. [Classes 2 (iii) and 15 (ii)] Printing textiles, e.g. direct or discharge printing of fabrics or yarns of cotton, regenerated cellulose. wool or silk, with water-soluble acyl derivatives of sparingly soluble dyestuffs, wherein the acyl residue carries the group imparting water solubility (cf. Specifications 480,358, 482,184, 505,504 and 512,664) is effected with the use as assistant in the printing paste of a water-soluble hydantoin of the general formula wherein R 1 , R 2  represent H or aliphatic hydrocarbon residues, substituted or not, R 3 , R 4  represent H, acyl groups containing not more than 4 carbon atoms or substituted cr unsubstituted aliphatic hydrocarbon residues. Specified assistants are hydantoin and its 5-methyl, 5-ethyl, 5:5-dimethyl, 5-propyl, 5- isopropyl, 5:5-methyl, ethyl, 5:5-methyl, propyl, 1- or 3-methyl, 3-ethyl, 3-allyl, 1- or 3-hydroxymethyl, 3-hydroxyethyl, 1-acetyl, 3-methyl-1- acetyl, 3-hydroxymethyl-5:5-dimethyl, 3:5:5:- trimethyl, 1-acetyl-5:5-dimethyl and 3- hydroxyethyl-5:5-dimethyl derivatives and hydantoin acetamid e-3. The hydantoin assistant may be incorporated in the printing paste directly or after preliminary admixture with the pulverulent dyestuff; another hydrotropic agent may be added, e.g. urea, thiourea, alkylthioglycollic acid amides, water-soluble salts of benzylanilinesulphonic acids, of cymenesulphonic acid or of substituted aromatic carboxylic acids or dicarboxylic acid semiesters or a water-soluble alcohol, e.g. glycol, glycerol or thiodiglycol. In examples, (1) a fabric made of cotton, regenerated cellulose, wool or silk, alone or in admixture, is printed with an aqueous paste containing the product of the action of benzoyl chloride-m-sulphonic acid on the dyestuff, 3-chloroaniline # the 2<SP>1</SP>- anisidide of 2:3-hyoroxyanaphthoic acid, 5:5- dimethylhydantoin or its 3-hydroxymethyl derivative and starch tragacanth thickening and the printed goods are dried, steamed, treated for 4-6 minutes in an aqueous solution at room temperature containing sodium hydroxide, barium chloride and sodium chloride, rinsed, soured, rinsed and soaped to obtain a fast orange print; (2) the dyestuff in (1) is replaced by the product of reaction of benzoic acid-m-sulphochloride or benzoic acid-3:5-disulphochloride or 4-chloromethylbenzoyl chloride in pyridine on the dyestuff, 2:5-dichloroaniline # the 2-anisidide of 2:3-hydroxynaphthoic acid, and the hydantoin derivative, which may be replaced by the 5:5-methyl, ethyl derivative, is used in conjunction with urea ; (3) the dyestuff in (2) is replaced by the product of reaction of benzoyl chloride-m-sulphonic acid on the condensation product from cyanoic chloride (1 mol.), 2-aminoanthraquinone (2 mols.) and aniline (1 mol. and the hydantoin derivative by 3:5:5-trimethylhydantoin; (4) the dyestuff in (2) is replaced by the product of reaction of benzoyl chloride-3-sulphonic acid on the dyestuff, 5-chloro-2-aminotoluene # the 2<SP>1</SP>-methyl-4<SP>1</SP>-chloroanilide or the 1<SP>1</SP>- or 21- naphthylamide of 2:3-hydroxynaphthoic acid, and the hydantoin derivative by 1-acetyl-5:5- dimethylhydantoin; (5) the dyestuff in (2) is replaced by the product of reaction of benzoyl chloride-3-sulphonic acid on the dyestuff, 2:5-diethoxy-4-benzoylaminoaniline # the anilide of 2:3-hydroxynaphthoic acid, and the hydantoin derivative by a mixture of the 5:5-methyl, propyl-, 5:5-methyl, ethyl- and 5:5-dimethyl-hydantoins ; the 5:5-methyl, propyl derivative may be replaced by the 3-hydroxyethyl-5:5-dimethyl derivative ; (6) the dyestuff in (2) is replaced by the product of reaction of benzoic acid-3:5-disulphochloride on the dyestuff, 1:naphthylamine # 2-naphthol, or on 4:4<SP>1</SP>-diaminodiphenyl ## 2-naphthol (2 mols.); (7) the dyestuff in (2) is replaced by the product of reaction of 4-chloromethylbenzoyl chloride in pyridine on the dyestuff, 2-nitraniline # 2- naphthol. 3- Hydroxymethyl hydantoin and its 5:5- dimethylhydantoin derivative are obtained by heating hydantoin and 5:5-dimethylhydantoin respectively with feebly alkaline aqueous formaldehyde at 60‹C. 3-Hydroxyethylhydantoin and its 5:5-dimethylhydantoin derivative are obtained by reaction of the mono-sodium salts of hydantoin and 5:5-dimethylhydantoin respectively with ethylenechlorhydrin in aqueous solution at 80-100‹C. Hydantoin-acetamide-3 is obtained by reaction of hydantoin with chloracetamide.