Patent GB-983362-A (GB)
Title: ª-cyano-2-alkoxy naphthyl-acrylamides and their use as ultra-violet absorbers
IPC: C09K15/22
Filed: 1961-04-04
Abstract: The invention relates in part to compounds of the formula <FORM:0983362/C2/1> in which R1 is an alkyl group of 1-9 carbon atoms or an alkenyl group of 3-18 carbon atoms and n is 1 or 2; when n is 1, R2 and R3 may be hydrogen atoms, alkyl groups of 1-18 carbon atoms, or hydroxyalkyl, hydroxyalkoxyalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl, aryl, substituted aryl or heterocyclic groups or R2 and R3, together with the nitrogen atom, may form a heterocyclic ring, e.g. a morpholino ring; when n is 2, R2 is a hydrogen atom and R3 may be an alkylene, arylene or divalent heterocyclic group.  Many radicals which R2 and R3 may denote are specified.  The compounds are obtainable by condensing an appropriately substituted naphthaldehyde with an appropriately substituted cyanoacetamide in the presence of a basic catalyst.  In typical examples: (1) 2-ethoxy-1-naphthaldehyde and cyanacetamide yield a product of the formula <FORM:0983362/C2/2> (2) 2 - ethoxy - 1 - naphthaldehyde and a  -cyano - N,N - dimethylacetamide yield a product of the formula <FORM:0983362/C2/3> (3) 2 - methoxy - 1 - naphthaldehyde and a  -cyano - N - phenylacetamide yield a product of the formula <FORM:0983362/C2/4> (4) 2 - ethoxy - 1 - naphthaldehyde and N,N1 -bis(cyanoacetyl)-ethylene diamine yield a product of the formula <FORM:0983362/C2/5> (5) 2 - ethoxy - 1 - naphthaldehyde and N,N1 -p-phenylene bis(cyanoacetamide) yield a product of the formula <FORM:0983362/C2/6> (6) 2 - allyloxy - 1 - naphthaldehyde and N,N1-bis(cyanoacetyl)-pentamethylenediamine yield a product of the formula <FORM:0983362/C2/7> The invention includes also polyoxyalkylated products obtained by treating compounds of the first formula above 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. In typical examples: (7) the product of Example 1 above is treated with 4 mols. of ethylene oxide or (8) successively with 4 mols. of ethylene oxide and 10 mols. of propylene oxide, and (9) the product of Example 3 above is treated with 40 mols. of ethylene oxide.  The products are useful as absorbers for ultra-violet light.  N,N1 - p - phenylene bis(cyanoacetamide), used in Example 5 above, is prepared from p-phenylenediamine and cyanoacetic acid in the presence of a mixed alkane sulphonic acid catalyst.  Specification 980,092 is referred to.ALSO:As ultra-violet light absorbers in synthetic polymers, use is made of compounds of the formula <FORM:0983362/C3/1> in which R1 is an alkyl group of 1-9 carbon atoms or an alkenyl group of 3-18 carbon atoms and n is 1 or 2; when n is 1, R2 and R3 may be hydrogen atoms, alkyl groups of 1-18 carbon atoms, or hydroxyalkyl, hydroxyalkoxyalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl, aryl, substituted aryl or heterocyclic groups or R2 and R3 together with the nitrogen atom, may form a heterocyclic ring, e.g. a morpholino ring; when n is 2, R2 is a hydrogen atom and R3 may be an alkylene, arylene or divalent heterocyclic group (see Division C2).  Many radicals which R2 and R3 may denote are specified. Use may be made also of polyoxyalkylated products obtained by treating compounds of the formula above 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. Thus, the compound of the formula <FORM:0983362/C3/2> is oxyalkylated with 15 and 40 moles of ethylene oxide in Examples (8) and (9) and with 10 moles of propylene oxide followed by 15 moles of ethylene oxide in Example 11. The compounds may be used in the treatment of polyethylene, ester polymers and formaldehyde polymers, and comparative examples are given of the use of the compounds in a polyethylene and a polyester resin comprising styrene and glycerol phthalatemaleate. Specification 980,092 is referred to.ALSO:As ultra-violet light absorbers in paints varnishes, lacquers and waxes, use is made of compounds of the formula <FORM:0983362/C4-C5/1> in which R1 is an alkyl group of 1-9 carbon atoms or an alkenyl group of 3-18 carbon atoms and n is 1 or 2; when n is 1, R2 and R3 may be hydrogen atoms, alkyl groups of 1-18 carbon atoms, or hydroxyalkyl, hydroxyalkoxyalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl, aryl, substituted aryl or heterocyclic groups or R2 and R3, together with the nitrogen atom, may form a heterocyclic ring, e.g. a morpholino ring; when n is 2, R2 is a hydrogen atom and R3 may be an alkylene, arylene or divalent heterocyclic group (see Division C2). Many radicals which R2 and R3 may denote are specified.  Use may be made also of polyoxyalkylated products obtained by treating compounds of the formula above 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.  Specification 980,092 is referred to.ALSO:As ultra-violet light-absorbers in sun-tan preparations, use is made of compounds of the formula <FORM:0983362/A5-A6/1> in which R1 is an alkyl group of 1-9 carbon atoms or an alkenyl group of 3-18 carbon atoms and n is 1 or 2; when n is 1, R2 and R3 may be hydrogen atoms, alkyl groups of 1-18 carbon atoms, or hydroxyalkyl, hydroxyalkoxyalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl, aryl, substituted aryl or heterocyclic groups or R2 and R3, together with the nitrogen atom, may form a heterocyclic ring, e.g. a morpholino ring; when n is 2, R2 is a hydrogen atom and R3 may be an alkylene, arylene or divalent heterocyclic group (see Division C2).  Many radicals which R2 and R3 may denote are specified. Use may be made also of polyoxyalkylated products obtained by treating compounds of the formula above 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. Specification 980,092 is referred to.ALSO:Transparent backing of pressure-sensitive adhesive tapes contains, as ultra-violet light absorbers, compounds of the formula: <FORM:0983362/B1-B2/1> in which R1 is an alkyl group of 1-9 carbon atoms or an alkenyl group of 3-18 carbon atoms and n is 1 or 2; when n is 1, R2 and R3 may be hydrogen atoms, alkyl groups of 1-18 carbon atoms, or hydroxyalkyl, hydroxyalkoxyalkyl, akoxyalkyl, cyanoalkyl, haloalkyl, aryl, substituted aryl or heterocyclic groups or R2 and R3 together with the nitrogen atom, may form a heterocyclic ring, e.g. a morpholino ring; when n is 2, R2 is a hydrogen atom and R3 may be an alkylene, arylene or divalent heterocyclic group (see Division C2). Many radicals which R2 and R3 may denote are specified. Use may be made also of polyoxyalkylated products obtained by treating compounds of the formula above with a polyoxyalkylating agent, e.g. ethylene oxide, propylene oxide, butylene oxide, butylene dioxide, cyclohexane oxide, glycidol, epichlorhydrin, butadiene dioxide or isobutylene oxide or mixtures thereof. Specification 980,092 is referred to.ALSO:As ultra-violet light absorbers in dyed textile materials or for opaque papers, use is made of compounds of the formula <FORM:0983362/D1-D2/1> in which R1 is an alkyl group of 1-9 carbon atoms or an alkenyl group of 3-18 carbon atoms and n is 1 or 2; when n is 1, R2 and R3 may be hydrogen atoms, alkyl groups of 1-18 carbon atoms, or hydroxyalkyl, hydroxyalkoxyalkyl, alkoxyalkyl, cyanoalkyl, haloalkyl, aryl, substituted aryl or heterocyclic groups or R2 and R3, together with the nitrogen atom, may form a heterocyclic ring, e.g. a morpholino ring; when n is 2, R2 is a hydrogen atom and R3 may be an alkylene, arylene or divalent heterocyclic group (see Division C2).  Many radicals which R2 and R3 may denote are specified. Use may be made also of polyoxyalkylated products obtained by treating compounds of the formula above 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. Specification 980,092 is referred to.