GB994346A - Ultraviolet absorbing compositions containing 2-alkoxy-ª‡-cyano-1-naphthalene acrylic esters - Google Patents

Abstract

Compounds used as ultra-violet radiation absorbers have the formula <FORM:0994346/C2/1> wherein R1 is C1- 9-alkyl or -alkenyl and n is 1 or 2; where n is 1, R2 is hydroxy-, halo-, cyano-, alkoxy-, hydroxyalkoxy-, carbalkoxy - or unsubstituted alkyl, aryl (optionally substitutes), alkenyl or hetero and when n is 2, R2 is optionally substituted alkylene or arylene, or a bivalent heterocyclic radical; they are prepared by condensing a 2-alkoxy, (or alkenoxy)-1-naphthaldehyde with a cyanoacetic ester in presence of an amine as described in Specifications 978,722 and 980,092. The following compounds are described: (1) n = 1, R1 = R2 = Me or Et; (2) n = 1, R1 = 2-nonenyl-1, R2 = Et; (3) n = 2, R1 = Et, R2 = 1,2-diphenylethylene; (4) n = 2, R1 = Me, R2 = the radical derived from 2,5-dihydroxypyridine; (5) n = 2, R1 = n-Pr, R2 = acenaphthylene; (6) the polyoxypropylated and/or polyoxyethylated product of n = 1, R1 = Me, R2 = hydroxyethyl.ALSO:Compounds of formula <FORM:0994346/C3/1> wherein n = 1, R1 is C1- 9-alkyl or alkenyl and R2 is hydroxyalkyl, may be polyoxyalkylated with up to 100 oxyalkyl groups using e.g. epichlorohydrin or oxides of ethylene, propylene, butylene, cyclohexene, isobutylene, butadiene or styrene. In Examples 36-39, the compound wherein R1 = Me and R2 = hydroxyethyl is polyoxyalkylated with ethylene oxide (5 or 35 moles) or with propylene oxide (10 moles) optionally followed by ethylene oxide (10 moles). A polyethylene wax contains as ultra-violet absorber a compound of the above formula wherein n = 1 and (a) R1 = Et, R2 = tetrahydrofuryl or nonyl, (b) R1 = 2-nonenyl-1, R2 = Et, or (c) R1 = n - Pr, R2 = acenaphthylene (Examples 6, 22, 32 and 35). A nitrocellulose lacquer contains as ultraviolet absorber a compound of the above formula, wherein n = 1 and (a) R1 = R2 = Et or (b) R1 = Et, R2 = p-methoxyphenyl (Examples 11 and 26). A styrene/glyceryl phthalate maleate resin cured with benzoyl-peroxide/tricresyl phosphate contains as ultra-violet absorber a compound of the above formula wherein n = 2 and (a) R1 = Me, R2 = ethylene, (b) R1 = Et, R2 = trimethylen or 1,2-diphenylethylene, or (c) R1 = n - Pr, R2 = o-xylylene (Examples 12, 29, 30 and 33).ALSO:A carnauba wax furniture polish incorporates an ultra-violet absorber of formula <FORM:0994346/C4-C5/1> wherein (a) R1=R2=Et, (b) R1=nonyl, R2=Et or (c) R1=methyl, R2=hydroxymethyl, turpentine, water and soap also being present (Examples 10, 19 and 20).ALSO:An ultra-violet absorber of formula <FORM:0994346/D1-D2/1> wherein R1 = allyl and R2 = Et is used to impregnate polyester fibre, a phenol-ethylene oxide (1:12) emulsifier also being present (Example 8). In Examples 18, 21, 27 and 28 the absorbers are (a) R1 = Et, R2 = allyl; (b) R1 = crotyl, R2 = ethyl; (c) R1 = allyl, R2 = hydroxyethyl and (d) R1 = methallyl, R2 = ethoxyethyl.