Patent GB-914074-A (GB)
Title: The colouration of textile materials of polymers and co-polymers of acrylonitrile and dicyanoethylenes
Inventor: HICKMOTT PETER WILLIAM
IPC: C09B44/02
Filed: 1960-05-12
Abstract: Textile materials of homopolymers of acrylonitrile or dicyanoethylenes, or of copolymers of these with one another or with other polymerizable vinyl compounds, are dyed with water-soluble dyestuffs of the monoazo series devoid of sulphonic and carboxylic acid groups and which do not contain a nitro group in ortho position to the azo group and which contain a group of the formula <FORM:0914074/IV (b)/1> wherein Y is an anion, R1 is a saturated chain of 2-6 C-atoms which may carry substituents, X is -O-, -NH- or -N(alkyl)- linked to an aromatic ring of the dyestuff directly or through -N(R)-R2-or -O-R2-, wherein R2 is a saturated chain of 2 or 3 C-atoms which may carry substituents and R is an alkyl group of up to 4 C-atoms, an aralkyl group or a group of the formula <FORM:0914074/IV (b)/2> Specified Y are sulphate, nitrate, methosulphate, methylsulphonate, chloride, bromide and iodide, specified R1 are -(CH2)2-, -(CH2)3-, -(CH2)5-, -CH2CH(CH3)-and -CH(CH3)CH2-, specified R2 are -(CH2)2-, -(CH2)3- and -CH2-CH (CH2CN) and specified R are methyl, ethyl, butyl, b -cyanoethyl and b -phenylethyl.  Dyeing may be carried out in a bath of pH 3-8 at a temperature of 85-100 DEG C or in a closed vessel up to 150 DEG C. Alternatively a printing paste thickened normally may be used, followed by steaming.  Common adjuvants may also be added.  Where X is -O-, R1 is -(CH2)2-, -CH2CH(CH3)- or -CH(CH3) CH2- and Y is halide the dyestuff is suitable for union dyeing acrylic and aromatic polyester textile materials, the acrylic material being dyed with the water-soluble dyestuffs of the invention and the polyester material being dyed with the insoluble dyestuff formed by splitting off the pyrimidium group.  The dyes wherein X is -O-, Y is a halide and R1 has 2 C-atoms, which may carry substituents, may be prepared by treating the appropriate hydroxy compound of the monoazo series with pyridine and an a -b -unsaturated carboxy halide at room temperature. When Y is a halide the dyestuff may also be prepared by reacting a compound of the monoazo series containing a group -X-CO-R1-Hal, where Hal is a halogen atom, with pyridine, which compound may be obtained by acylation with a halide of the formula Hal1-X-CO-R1-Hal.  Examples are given of dyeing, printing and the preparation of a number of dyestuffs typical of which are the reaction products of 4-nitro-41(N- methyl-N- b -hydroxyethylamino)-azo-benzene, acryloyl chloride and pyridine, 2 : 4-bis-methylsulphonyl-41- [N-methyl-N- b -(b 1 -chloropropionylamino) ethylamino] azobenzene and pyridine, 2-chloro-4-nitro-41[N-b -cyano-ethyl- N-b 1-(g  -bromobutyryloxy) ethyl-amino]-21-methylazobenzene and pyridine, 4-sulphamoyl- 41-[N-b -(N1-methyl- N1-o -bromo -caproylamino) ethyl-N-methylamino] azobenzene and pyridine, 1-(31-o -bromocaproylaminophenyl) - 3-methyl-4-(311- chlorophenylazo)-5-pyrazolone and pyridine, 1-phenyl-3-methyl- 4-(41-b - hydroxyethoxyphenylazo) -5-pyrazolone, acryloyl chloride and pyridine and 6-thiocyano-2- [41-(N-b -cyanoethyl- N-b -hydroxyethylamino) phenylazo] benzthiazole, acryloyl chloride and pyridine. Specification 789,263 and U.S.A. Specification 2,359,862 are referred to.