Patent GB-843643-A (GB)
Title: Improvements in or relating to water-insoluble styryl dyestuffs
IPC: C08K5/42
Filed: 1957-07-17
Abstract: Secondary celulose acetate, cellulose triaceltate, nylon, rilsan, polyglycol terephthalate, polyethylene, polyacrylonitrile, polyvinyl-chloride and copolymers of vinyl chloride and acrylonitrile are spun-dyed into coloured filaments from a solution or melt with a dyestuff of the formula:  <FORM:0843643/IV(a)/1> wherein R1 is chlorine, bromine, or the R3-CO-O- radical in which R3 is methyl, chlormethyl, ethyl, chloroethyl, n-propyl, isopropyl, methoxymethyl or ethoxyethyl, R2 is alkyl of 1-4 carbon atoms or, when R1 is R3-CO-O-, also the R3-CO-O-CHCH2- radical, X is <FORM:0843643/IV(a)/2> methyl or ethyl, Y is hydrogen, methyl, ethyl, methoxy or ethoxy, Z is hydrogen or methyl, m is 1 or 2 and aryl denotes an unsubstituted or substituted benzene, naphthalene, tetrahydronaphthelene or diphenyl residue, the aromatic residues being directly connected in a nuclear position to the sulphone linkage, the tetrahydro-naphthalene being connected in the aromatic ring and, when m = 2, the diphenyl residue having one sulphone linkage attached to each benzene ring.  Examples are given. Specification 843,645 is referred to.ALSO:1 - (N, N - Dipropionyloxyethyl)-amino-3-methyl-4-benzaldehyde is made by reacting 1 - (N, N-dipropionyloxyethyl)-amino-3-methyl-benzene with phosphorous oxychloride and N, N-dimethylformamide.  (3 : 4 - Dichlorophenyl-1-sulphonyl)-acetonitrile is made by reacting sodium 3:4-dichlorobenzene-1 sulphinate with chlorocetamide and then heating the product obtained with phosphorous oxychloride.  A mixture of 1- (N-ethyl-N-chloroethyl)-amino-3-methyl-4-benzaldehyde and 1 - (N : N-diethyl)-amino-3-methyl-4-benzaldehyde is made by treating a mixture of 1-(N-ethyl-N-hydroxyethyl)-amino-3-methylbenzene and 1-(N : N - diethyl)-amino-3-methylbenzene with phosphorous oxychloride and N-methyl-N-formyl-aminobenzene.  Specification 843,645 is referred to.ALSO:The invention comprises water-insoluble styryl dyestuffs of the formula:  <FORM:0843643/IV (c)/1> wherein R1 is chlorine, bromine or the R3-CO-O-radical in which R3 is methyl, chloromethyl, ethyl, chloroethyl, n-propyl, isopropyl, methoxymethyl or ethoxyethyl, R2 is an alkyl radical of 1-4 carbon atoms or, when R1 is R3-CO-O-, also the <FORM:0843643/IV (c)/2> , X is methyl or ethyl, Y is hydrogen, methyl, ethyl, methoxy or ethoxy, Z is hydrogen or methyl, m is the number 1 or 2, and in which aryl denotes an unsubstituted or substituted benzene, naphthalene, tetrahydronaphthalene or diphenyl residue being directly connected in a nuclear position to the sulphone linkage, the tetrahydronaphthalene being connected in the aromatic ring and, when m is 2, the diphenyl residue having one sulphone linkage attached to each benzene ring.  The invention further comprises a method for making the dyestuffs by condensing m mols of the aldehyde of the formula:  <FORM:0843643/IV (c)/3> with 1 mol of an active methylene compound of the formula: aryl-(SO2-CH2-CN)m The condensation is effected by reaction at elevated temperature in an inert organic solvent in the presence of a small quantity of a basic substance such as ammonia, dimethylamine, diethylamine or piperidine, or by heating the reactants in the presence of glacial acetic or another organic acid and a base such as those mentioned above in benzene, toluene, xylene, chloroform or carbon tetrachloride with continuous removal of water of reaction. The condensation may also be effected by saturating a solution of the reactants in an inert organic solvent with dry hydrogen chloride and distilling or heating the addition product with tertiary amines such as dimethyl- or diethylaniline, or by melting the reactants in absence of a solvent with a base such as ammonia, dimethylamine, diethylamine, piperidine or its acetate or ammonium acetate.  A very large number of examples is given.  The dyestuffs are used for the mass pigmentation of oils, lacquer media, moulding resins and textile fibres prior to extrusion or spinning.  Specification 843,645 is referred to.