Patent GB-1025568-A (GB)
Title: Aryl hetero methylene malonitriles
IPC: C07D333/24
Filed: 1963-05-30
Abstract: A liquid detergent composition contains as a novel ultra-violet light proofing ingredient an oxyethylated para-hydroxyphenyl 5-methyl-2-thienylmethylene malonitrile having 30 oxyethylene units, in admixture with tetrapotassium pyrophosphate, a nonylphenyl ethylene oxide condensate, sodium silicate, carboxymethyl cellulose, potassium hydroxide and water.ALSO:The invention comprises compounds of the formula <FORM:1025568/C2/1> wherein (Ar1) is a heterocyclic nucleus containing at least one pair of conjugated double bonds and (Ar2) is an aromatic carbocyclic nucleus, the said nuclei being devoid of nitro and nuclear-bonded amino groups.  The above compounds are prepared by condensing an aryl hetero ketone of the formula (Ar1)-CO-(Ar2) with malononitrile or with cyanoacetamide, followed by dehydration of the resulting nitrile amide to the dinitrile. Specified heterocyclic rings are those of thiophene, furan, pyrrole, a -pyran, a -pyrone, pyridine, 1,2-dihydropyridine, oxazole, thiazole, isoxazole, isothiazole, pyrazole, 3-isopyrazole, imidazole, 2-isoimidazole, 1,2,3-triazole, 1,2,4 - triazole, tetrazole, 1,3,4 - oxadiazole, 1,2,5 - oxadiazole, 1,2,3 - thiadiazole, 1,2,3 - oxathiazole, pyridazine, pyrimidine, pyrazine, 1,3,5 - triazine, benzothiophene, benzofuran, cinnoline, phthalazine, benzimidazole, 1,3,5 - benztriazole and benzoxazole, each of which may be substituted by alkyl, alkenyl, cyanoalkyl, hydroxyalkyl, carbalkoxy, chloroalkyl, bromoalkyl, alkoxyalkyl, hydroxyalkoxyalkyl, halogens, acyl, alkylsulphonyl, arylsulphonyl, hydroxy, alkoxy or aminocarbonyl. Specified aromatic carbocyclic rings are benzene, naphthalene, anthracene and phenanthrene, each of which may be substituted by keto, alkyl, aryl, alkoxy, hydroxyalkyl, halogen, carboxyl, carbalkoxy, acyl, acylamino or sulphamyl.  The products may also contain polyoxyalkyl groups derived by treating either the products or starting materials with alkylene oxides.ALSO:Aryl heteromethylene malonitriles of the formula:-<FORM:1025568/C3/1> wherein (Ar1) is a heterocyclic nucleus containing at least one pair of conjugated double bonds and (Ar2) is an aromatic carbocyclic nucleus, the said nuclei being devoid of nitro-and nuclear-bonded amino groups but containing optional hydroxy, amide or carboxyl groups or groups containing such substituents, their oxyalkylated derivatives may be incorporated as ultra-violet light proofing agents in nitrocellulose lacquers also containing alkyd resins, dibutyl phthalate, butyl acetate, butanol and toluene; in films formed from such lacquers; in polyethylene and films formed therefrom; in an acrylonitrile-butadiene latex; and in a granular high molecular weight formaldehyde polymer.  Polyoxyalkylated compounds are obtained by reacting the above compounds containing hydroxy, amide or carboxyl groups with up to 200 mols of alkylene or styrene oxides, butadiene oxide, glycidol or epichlorhydrin.ALSO:Films resistant to ultra-violet light are formed on leather by spraying same with an acrylonitrile-butadiene latex to which has been added 4, 5-dimethyl-3-pyroyl phenyl methylene malononitrile dispersed with formaldehyde-naphthalene-2-sodium sulphonate.  A sponge of polyvinyl chloride is rendered stable to ultra-violet light by impregnating it with a petroleum ether solution of 2, 5-dimethyl-3-thienyl phenyl methylene malononitrile, squeezing it free of solvent and drying it.ALSO:Paper, cotton and gelled regenerated cullulose are proofed against ultra-violet radiation by treatment with aqueous dispersions of aryl hetero methylene maloronitriles of the formula:- <FORM:1025568/D1-D2/1> wherein (Ar1) is a heterocyclic nucleus containing at least one pair of conjugated double bands and (Ar2) is an aromatic carbocyclic nucleus, said nuclei being devoid of nitro and nuclear-bonded amino groups.