Patent GB-927404-A (GB)
Title: Water-soluble dyestuffs containing hydroxy alkyl groups
Inventor: HESLOP ROBERT NORMAN
IPC: D06P1/00
Filed: 1959-11-20
Abstract: 4-Amino-o -[N- (2:3:4:5:6-pentahydroxy-n-hexyl) -N- methylamino]- acetophenone is made by reacting acetanilide with chloracetyl chloride, condensing the 4-acetylamino-o -chloroacetophenone obtained with N-methyl glucamine and hydrolysing the acetyl group with dilute aqueous hydrochloric acid.  4-Aminobenzene sulphone-N- methyl-N-b -[N1-(2:3:4:5:6- pentahydroxyn -hexyl)-N1-methylamino]ethylamide is made by chlorosulphonating acetanilide, treating with N-methyl glucamine and hydrolysing the acetyl group.  4-Amino-o -[N1- (2:3:4:5:6-pentahydroxy-n-hexyl) -N1-methylamino]- N-ethyl-acetanilide is made by reacting 4-nitro-N-ethylaniline with chloracetyl chloride, treating the product with N-methyl-glucamine and reducing the nitro group with iron filings.ALSO:The invention comprises water-soluble dyes which contain at least one sulphonic acid or carboxylic acid group and at least one group of the formula <FORM:0927404/IV(a)/1> wherein A is a substituted or unsubstituted alkylene radical, R11 is hydrogen or a substituted or unsubstituted alkyl radical and Y is an alkyl radical containing at least two hydroxy groups, in which the group of Formula I is attached to a carbon atom of an aryl ring through one of the linking groups <FORM:0927404/IV(a)/2> and <FORM:0927404/IV(a)/3> where R is hydrogen or substituted or unsubstituted alkyl.  The dyes specified are of the monoazo, polyazo, metallized azo, nitro, anthraquinone and phthalocyanine series.  Alkyl radicals specified for group Y include dihydroxypropyl and -butyl, trihydroxy-butyl and -pentyl and pentahydroxyhexyl.  The dyes are made by reacting an amine of the formula <FORM:0927404/IV(a)/4> with a water-soluble dye containing at least one sulphonic or carboxylic acid group and at least one group -A-Z attached via <FORM:0927404/IV(a)/5> or <FORM:0927404/IV(a)/6> or at least one group -CH2CH2OW attached via <FORM:0927404/IV(a)/7> or at least one vinyl group attached via <FORM:0927404/IV(a)/8> where A, R, R11 and Y are as above, Z is chlorine or bromine and W is the residue of a mono- or polybasic organic or inorganic acid.  Azo dyes are also made by coupling a diazotized aromatic amine with a coupling component, at least one of the reactants containing a sulphonic or carboxylic acid group and at least one containing a group of Formula I above.  Examples are given.  The dyes dye cellulose textile materials in a variety of shades, if desired in conjunction with a treatment with formaldehyde and/or a resin-forming intermediate and an acid-liberating catalyst and a subsequent heat treatment at above 100 DEG C.  Resin-forming intermediates mentioned are methylol-melamine, methylolurea, acetals, isocyanates, dimethylol cyclic ethylene urea, dimethylolglyoxal urea, dimethylol cyclic propylene urea, tetramethylol acetylene diurea and methyloltriazines. Acid-liberating catalysts mentioned are ammonium dihydrogen phosphate, ammonium thiocyanate, zinc chloride, magnesium chloride, zinc nitrate and 2-methyl-2-aminopropanol hydrochloride.  The Provisional Specification refers to watersoluble dyes containing at least one group of the formula <FORM:0927404/IV(a)/9> where X is <FORM:0927404/IV(a)/100> A is a substituted or unsubstituted alkylene radical, R, R1 and R11 are each hydrogen or substituted or unsubstituted alkyl, Y is an alkyl or cycloalkyl radical containing at least two hydroxy groups and n and m are each 1 or 2.  Di-(b -chloroethylsulphamyl) -1:4 - bis-(211 - methoxy-41-phenoxyanilino)anthraquinone-disulphonic acid is made by reacting b -chloroethylamine hydrochloride with sulphochlorinated 1:4-bis-(211-methoxy-41-phenoxyanilino)anthraquinone.  3-[31-(b -sulphatoethylsulphonyl)phenylsulpamyl]copper phthalocyanine sulphonic acid and 3-(31-b -sulphatoethylsulphonylmethyl-41 -methylphenylaminosulphonyl)-copper phthalocyanine sulphonic acid are made by reacting sulphochlorinated copper phthalocyanine with 3-aminophenylb -hydroxyethyl sulphone hydrochloride and 5-amino-2-methylbenzyl-p-hydroxyethylsulphone respectively and esterifying the products with sulphuric acid.  Copper phthalocyanine-3-sulphonic acid sulphonamide sulphon-b -chlorethylamide is made by reacting sulphochlorinated copper phthalocyanine with b -chloroethylamine and ammonia.  Copper phthalocyanine-4-sulphonic acid-sulphon-N-methyl-N-pentahydroxyhexyl amide-sulphon-b -chloroethylamide and copper phthalocyanine-4-sulphonic acid sulphon-b -hydroxyethylamide sulphon-b -chloroethylamide are made by treating copper phthalocyanine tetra-4-sulphonic acid with chlorosulphonic acid and reacting the sulphochloride obtained with b -chloroethylamino and respectively N-methyl-glucamine or monoethanolamine.  Copper phthalocyanine-4-sulphonic acid-sulphonamide-sulphon-b :g -dichloropropyl amide and the corresponding -g -chloro-b -hydroxypropylamide are made by reacting the sulphochloride obtained from copper phthalocyanine tetra-4-sulphonic acid and chlorosulphonic acid with ammonia and respectively b :g -dichloropropylamine or g -chloro-b -hydroxypropylamine.  Specifications 587,467, 712,037, 733,471, 7490,533, 768,241, 774,819, 776,265, 779,781, 779,818, 787,986, 826,689, 830,847, 837,750, 852,960, 858,183, 868,492, 870,047, 881,737, 882,750, 885,814, 885,681, 886,379, 887,870 and 891,248 are referred to.