Patent GB-843644-A (GB)
Title: Improvements in or relating to new water-insoluble styryl dyestuffs
IPC: C08K5/00
Filed: 1957-07-17
Abstract: Cellulose esters and synthetic polymers are spun-dyed with a water-insoluble dyestuff of the formula:  <FORM:0843644/IV(a)/1> where A is cyano, carbalkoxy, carbalkoxyalkoxy or a phenyl-diphenylyl, naphthyl- or tetrahydronaphthyl-monosulphonyl radical, the sulphonyl group being attached to the aromatic ring thereof, or a 1 : 3 :3-trimethylindoleninium radical linked in the 2-position when n is 1, or a diphenylene - or naphthylene-disulphonyl radical when n is 2, x is hydrogen, methyl, ethyl, methoxy or ethoxy, y is hydrogen, methyl, ethyl, methoxy, or ethoxy, or when A is 1 : 3 :3-trimethylindoleninium also halogen or trifluoromethyl, R1 and R2 are alkylene radicals of 1 to 4 and 2 to 4 carbon atoms respectively, R3 is an aliphatic, cycloaliphatic or aromatic radical free from water-solubilizing groups, one V is oxygen and the other V is -NH-, M is hydrogen, alkyl of not more than 5 carbon atoms, cyanomethyl, tri- or bi-fluoromethyl, carboalkoxy or the R3-V-CO-V- radical when A is a 1 : 3 : 3-trimethylindoleniuium radical, or, when A has another meaning, hydrogen, alkyl or alkoxy of not more than 5 carbon atoms or R3-V-CO-V-, T is hydrogen when A is 1 : 3 : 3-trimethylindoleninium or cyano when A has another meaning, and n is 1 or 2.  In examples, solutions of (2) and (164) cellulose acetate in acetone-methanol, (153) cellulose triacetate in methylene chloride-ethanol, (154) polyethylene in xylene, (155) polyvinyl chloride in cyclohexanone-ethylhexanone, (156) postchlorinated polyvinylchloride in acetone and diethyl sulphide, (157) a copolymer of vinyl chloride and acrylontrile in acetone, and (158) and (159) polyacrylonitrile in dimethylformanide are mixed with dyestuff solutions and spun; in other examples (160) Rilson, (161) nylon, and (162) the condensate of terephthalic acid and glycol or of the dimethyl ester and glycol are mixed with the dyestuff and melted and spun: example 163 also illustrates the spin-dyeing of polyethylene and polystyrene. Specification 843,645 is referred to.ALSO:1 - [N-ethyl-N-beta-(phenylcarbamyloxy) -ethyl]-amino-3-methyl-4-benzaldehyde is made by heating 1-[N-ethyl-N-beta-(phenylcarbamyloxy) -ethyl]-amino-3-methyl-benzene with phosphorous oxychloride and N:N-dimethylformamide and the reaction mass poured into water. Specification 843,645 is referred to.ALSO:The invention comprises water-insoluble styryl dyestuffs of the formula:  <FORM:0843644/IV (c)/1> where A is cyano, carbalkoxy, carbalkoxyalkoxy, or a phenyl-, diphenylyl-, naphthyl- or tetrahydronaphthyl - monosulphonyl radical which may be substituted by halogen or alkyl groups of less than 6 carbon atoms, the sulphonyl group being attached to the aromatic ring of the tetrahydronaphthyl radical, or a 1 : 3 : 3-trimethylindoleninium radical linked in the 2-position and further substituted if desired, when n is 1, or a diphenylene- or naphthylene-disulphonyl radical which may be substituted, when n is 2, x is hydrogen, methyl, ethyl, methoxy or ethoxy, y is hydrogen, methyl, ethyl, methoxy or ethoxy or, when A is 1 : 3 : 3-trimethylindoleninium, also halogen or trifluoromethyl, R1 is an alkylene radical of 1 to 4 carbon atoms, R2 is an alkylene radical of 2 to 4 carbon atoms, R3 is an aliphatic, cycloaliphatic or aromatic radical which is free from water-solubilizing groups and may be further substituted, one V is oxygen and the other V is the -NH- group, M is hydrogen, alkyl or alkoxy of not more than 5 carbon atoms, cyanomethyl, difluoromethyl, trifluoromethyl, carbalkoxy, or the R3-V-CO-V- radical, when A is a 1 : 3 : 3-trimethylindoleninium radical, or, when A has another meaning, hydrogen, alkyl or alkoxy of not more than 5 carbon atoms or R3-V-CO-V-, T is hydrogen when A is 1 : 3 : 3-trimethylindoleninium or cyano when A has another meaning, and n is 1 or 2.  The dyestuffs are made by reacting 1 mole of an appropriate aldehyde of the formula:  <FORM:0843644/IV (c)/2> with one mole of malonic acid dinitrile or of an alkyl ester or alkoxyalkyl ester of cyanoacetic acid or a phenylsulphonyl or diphenylylsulphonyl or tetrahydronaphthylmonosulphonyl or naphthylmonosulphonyl acetonitrile or a 1 : 3 : 3 -trimethyl-2-methylene-indolenine, or 2 moles of the above aldehyde with one mole of a naphthylenedisulphonyl or diphenylenedisulphonyl acetonitrile.  Many examples are given. The dyestuffs dye or spin-dye cellulose esters, synthetic polymers, oils and lacquer media. Specification 843,645 is referred to.