Patent ES-247862-A1 (ES)
Title: New monomeric, polymerisable, ultra-violet light-screening esters and amides, their polymerisation and use
IPC: D06M13/203
Filed: 1959-03-12
Abstract: Ultra-violet light-screening polymers are obtained by the polymerization of a monomeric U.V.-absorbing ester or amide which has been prepared by reacting an acid halide of a polymerizable aliphatic mono- or dicarboxylic acid with a U.V.-absorbing compound containing at least one benzene ring and a grouping attached thereto which together form a conjugated system the said compound containing at least one hydroxyl or amino group capable of reacting with an acid halide without losing its U.V.-absorbing properties said compound, and said monomeric ester or amide, having a molecular extinction coefficient (measured in ethanol) of at least 10,000 in the range 240-400 mm . Specified polymerizable acids for the preparation of the monomers are acrylic, crotonic, methacrylic, chloroacrylic, itaconic, fumaric and maleic acids specified U.V.-absorbing hydroxy- and amino-compounds are those of the formul <FORM:0898065/IV (a)/1> where R8 is a benzene, diphenyl or pyridine residue <FORM:0898065/IV (a)/2> where A is an aliphatic hydrocarbon radical R9-R10-NH2, where R9 is a benzthiazole, benzoxazole or benzimidazole residue bound in 2-position to R10, which is a benzene residue bound in 4-position to the amino group A-O-COR10NH2, where A is an alkyl group and R10 is a benzene residue bound in 1-position to the -OCO- group and in 4-position to the amino group and 7-aminocoumarins (see Group IV(b)). The monomers may be homopolymerized or copolymerized, in bulk, in organic solution or in emulsion. Suitable monomers for copolymerization contain the group CH2=C<, such as vinyl esters of organic acids (e.g. the acetate, formate, butyrate or benzoate) vinyl alkyl ketones vinyl halides such as vinyl and vinylidene chloride styrene and substituted styrenes acrylic acid esters acrylonitrile acrylamide substituted amides of acrylic, methacrylic, chloroacrylic, maleic and fumaric acids olefines, such as isobutylene, butadiene 2-chlorobutadiene heterocyclic compounds such as N-vinylcarbazole, N-vinylimidazole, vinylpyrrolidone and vinylpyridine unsaturated ethers such as vinyl and isobutylvinyl ethers acids such as acrylic and methacrylic acids. One or more such polymerizable compounds may be used to prepare copolymers with the U.V.-absorbing ester or amide. The polymers are used for impregnating or coating, e.g. coating wood surfaces, paper, textiles and laminates. Specifications 880,549 and 893,236 are referred to.ALSO:The invention comprises monomeric polymerizable ultra-violet light-screening esters or amides which retain their light-screening properties on polymerization, and which have been obtained by reacting an acid halide of a polymerizable aliphatic mono- or dicarboxylic acid with an ultra-violet light-absorbing compound containing at least one benzene ring and a grouping attached thereto which together form a conjugated system, the said compound containing at least one hydroxyl or amino group capable of reacting with an acid halide without losing its ultra-violet light-screening properties said compound, and also the ester or amide derived therefrom by reaction with the polymerizable acid halide, having a molecular extinction coefficient (measured in ethanol) of at least 10,000 in the range 240-400 mm . Specified polymerizable acids are acrylic, crotonic, methacrylic, chloroacrylic, itaconic, fumaric and maleic acids. Specified types of ultra-violet screening hydroxy-and amino-compounds are those of the formulae <FORM:0898065/IV (b)/1> where R8 is a benzene, diphenyl or pyridine residue <FORM:0898065/IV (b)/2> where A is an aliphatic hydrocarbon residue R9-R10-NH2, where R9 is a benzthiazole, benzoxazole or benzimidazole residue bound in 2-position to R10 and R10 is a benzene residue bound in 4-position to the amino group A-O-CO-R10-NH2, where A is an alkyl group and R10 is a benzene residue bound in 1-position to the -OCO-group and in 4-position to the amino group and 7-aminocoumarins. Examples prepare the compounds of the formulae <FORM:0898065/IV (b)/3> Specifications 880,549 and 893,236 are referred to.ALSO:Textiles are protected against ultra-violet light by treatment with a polymerisable u.v.-absorbing ester or amide (see Group IV (b)) or with a homopolymer or copolymer thereof (see Group IV (a) or dyed textiles can be similarly protected by a screen of such a polymer. In Examples (33) a polyamide fabric is treated with the ester <FORM:0898065/IV (c)/1> in ethanol in the presence of a reaction product from octadecyl alcohol and ethylene oxide (34) as in (33) in the presence of formic acid also (35) polyamide fibre yarn is similarly treated (36) wool gaberdine dyed with a commercial acid wool dye is protected against u.v-light by an acetylcellulose film containing the ester <FORM:0898065/IV (c)/2> (38) bleached jute is coated with an emulsion obtained by polymerising the ester <FORM:0898065/IV (c)/3> and dried (41) a polyamide fabric dyed with the dyestuff <FORM:0898065/IV (c)/4> is coated with the emulsion used in (38) and dried (42) wool serge dyed with the above dyestuff is protected against u.v. light by a glass plate coated with the emulsion used in (38). Specifications 880,549 and 893,236 are referred to.