Patent GB-1023384-A (GB)
Title: Improvements in or relating to nitrile compounds
IPC: C08K5/16
Filed: 1963-12-30
Abstract: As ultra-violet absorbers for waxes, use is made of compounds of the formula <FORM:1023384/C4-C5/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2).  Many radicals which R, R1, R2 and R3 may denote are specified. The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.  An example is given of the use of one of the products in a furniture polish based on carnauba wax.ALSO:As ultra-violet absorbers for polymeric materials, use is made of compounds of the formula <FORM:1023384/C3/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2).  Many radicals which R, R1, R2 and R3 may denote are specified The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexene oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.  Specified polymeric materials which may be treated include natural or regenerated cellulose, cellulose acetate, nitrocellulose, cellulose ethers, epoxy resins, polyethylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymers, polystyrene, acrylate and methacrylate polymers, polyvinyl ethers and ketones, polytetrafluoroethylene, polyoxymethylene and ester polymers. Comparative examples are given of the use of one of the products in nitrocellulose lacquer, a polyester resin comprising styrene and glyceryl phthalate-maleate.ALSO:The invention comprises compounds of the formula <FORM:1023384/C2/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2. Many radicals which R, R1, R2 and R3 may denote are specified.  The compounds may be prepared by condensing an appropriate aromatic ketone with malononitrile under dehydrating conditions, preferably in a solvent. Alternatively, the ketone may be condensed with cyanoacetamide and the amido group then converted into a nitrile group by dehydration, preferably with phosphorus oxychloride.  Many ketones which may be used in the reaction are specified.  Typical examples describe the manufacture of products from (a) 4-hydroxy-3,5-dimethylacetophenone, (b) 3-butyl-4-ethoxy-acetophenone, (c) 3-methyl-4-phenoxybutyrophenone, (d) 3 - ethyl - 4 - (p - chlorobenzyloxy) butyrophenone, (e) 3-methyl-4-allyloxybutyrophenone and 3 - allyl - 4 - methoxyacetophenone. The invention includes also polyoxalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexene oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof, and examples of such reactions are given.  The products are useful as absorbers for ultra-violet light (see Divisions A5, B2, B5, C3, C5, D1 and D2).ALSO:As ultra-violet absorbers in the treatment of dyed textile materials and opaque papers, use is made of compounds of the formula <FORM:1023384/D1-D2/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2).  Many radicals which R, R1, R2 and R3 may denote are specified.  The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.ALSO:As ultra-violet absorbers for incorporation into transparent coatings or backings e.g. of pressure-sensitive tapes, use is made of compounds of the formula <FORM:1023384/B1-B2/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2).  Many radicals which R, R1, R3 and R2 may denote are specified. Specified backings are regenerated cellulose films which may contain the absorber or may be coated with a nitrocellulose lacquer containing the absorber.  The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.ALSO:As ultra-violet absorbers in sun-tan preparations, use is made of compounds of the formula <FORM:1023384/A5-A6/1> in which R, R2 and R3 are alkyl groups of 1-30 carbon atoms or alkenyl groups of 3-30 carbon atoms, R1 is hydrogen or an organic radical, m and n are 0 or 1 and the sum of m and n is 1 or 2 (see Division C2).  Many radicals which R, R1, R2 and R3 may denote are specified.  The invention includes also polyoxyalkylated products obtained by treating compounds of the formula above which contain a reactive hydrogen atom with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexene oxide, glycidol, epichlorohydrin, butadiene dioxide or isobutylene oxide or mixtures thereof.