Patent GB-900764-A (GB)
Title: Water-soluble dyestuffs containing sulphonic acid and methylol groups and the production of the same
Inventor: LANGE GUENTER
IPC: C09B1/34
Filed: 1960-06-10
Abstract: The preparation of compounds containing glyoxaldiureine radicals of formula:-  <FORM:0900764/IV (b)/1> by the reaction of ureido-substituted compounds with glyoxal monoureine or diethers thereof is described.  They are used in the preparation of dyestuffs (see Group IV(c)).  In Examples: (1) 4-acetylaminophenylurea is reacted with glyoxal monoureine dimethyl ether in a mixture of aqueous acetic and hydrochloric acids to give N-(4-acetylamino-phenyl)-glyoxaldiurein which is hydrolysed with aqueous sodium hydroxide to N-(4-aminophenyl)-glyoxaldiureine; (2) 4-hydroxy-phenylurea and 8-hydroxy-6-sulphonaphthyl-(2)-urea are reacted with glyoxal monoureine dimethyl ether with the addition of hydrochloric acid in aqueous ethanol and water respectively to give N-(4-hydroxyphenyl)- and N - (8-hydroxy-6-sulphonaphthyl-(2))-glyoxaldi-ureines.  Further compounds specified are N-(3-aminophenyl)- or -(3-chloro- or -sulpho- or -methoxy - 4 - aminophenyl) - glyoxaldiureines. Specification 842,802 is referred to.ALSO:The invention comprises water-soluble dyestuffs of formula:-<FORM:0900764/IV (b)/1> wherein D is an azo, metallised azo or anthraquinone dyestuff radical, m is 1 or 2 and n is 1, 2 or 3.  They are prepared by treating a suitable dyestuff containing 1 or 2 glyoxal-diureine radicals of formula:- <FORM:0900764/IV (b)/2> with aqueous formaldehyde in weak acid to alkaline medium.  They are used to dye or print textile materials of wool, polyamides, polyurethane and particularly cellulose, and also leather in various shades.  Textile materials are treated with the dyestuffs in the presence of acids or acid donors and the dyeings fixed by heating at 100 DEG -160 DEG C.  Reaction between the dyestuff and the fibre is assumed to occur.  Specified acids and acid donors are boric, phosphoric, formic, acetic, glycollic, tartaric, chloracetic, chlorpropionic, citric and malic acids and ammonium nitrate or chloride, monoammonium phosphate, zinc or magnesium chloride and diethanolammonium chloride.  The usual dyeing auxiliaries may also be used.  In examples: (1) the dye N-(4-aminophenyl)-glyoxaldiureine --> 2-naphthol-5-sulphonic acid is prepared and treated with formaldehyde, an aqueous solution of the dye obtained and ammonium nitrate is padded on to a cotton fabric, the fabric is squeezed off, dried, heated at 150 DEG C. for 5 minutes, soaped and dried to give a red dyeing; in similar examples further components specified include N-(3-aminophenyl)-glyoxaldiureine, N(3-chloro- or -sulpho- or -methoxy-4-aminophenyl)-glyoxaldiureine, 1-(21-cholor-51-sulphophenyl)-3-methyl-5-pyrazolone, 1-naphthol-3or -4-sulphonic acid, 1-acetylamino-8-naphthol-3:6-disulphonic acid and N-(8-hydroxy-6sulphonaphthyl-(2))-glyoxaldiureine; (2) the following dyes are prepared and treated with formaldehyde 4-aminobenzene-sulphonic acid --> N-(4-hydroxyphenyl)-glyoxaldiureine, 2aminobenzoic acid --> N-(8-hydroxy-6-sulphonaphthyl-(2))-glyoxaldiureine; 4-nitroaniline --> 1-amino-8-naphthol-3:6-disulphonic acid \sM N-(4-amino-3-sulphophenyl)-glyoxaldiureine and the chromium complex of 5nitro-2-aminophenol --> N-(4-hydroxyphenyl)glyoxaldiureine; (3) 1-amino-4- (41-ureidophenylamino)-anthraquinone-2-sulphonic acid is reacted with glyoxalmonoureine dimethyl ether to give 1-amino-4-(41-glyoxal-diureinylphenylamino) -anthraquinone-2-sulphonic acid which is reacted with formaldehyde. The corresponding 21-sulpho-compound is also specified as starting material.  Specification 842,802 is referred to.