Melamine-based light stabilizers for plastics

C - Chemistry – Metallurgy – 07 – D

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400/7080, 260/24

C07D 401/14 (2006.01) C07D 405/14 (2006.01) C08K 5/3477 (2006.01) C08K 5/3492 (2006.01)

Patent

CA 2005233

Melamine-based compounds having a multiplicity of 2,2,6,6-tetraalkyl piperidine moieties are useful as light stabilizers for organic polymers. The compounds have the formula: (see fig. I) wherein: R is the group: (see fig. II) R1 is selected from hydrogen and an alkyl group having 1-5 carbon atoms, R2 is selected from the group consisting of hydrogen, oxyl, hydroxyl, a straight or branched chain methylene-linked alkyl group having 1-18 carbon atoms, an alkanoyl group having 2-18 carbon atoms, an alkenyl group having 3-4 carbon atoms, an alkenoyl group having 3-6 carbon atoms, an alkynyl group having 3-6 carbon atoms, a cyanomethyl group, a 2,3-epoxypropyl group, a benzyl or alkylbenzyl group having 7-15 carbon atoms, a group having the formula -CH2CH(OR3)-R4, and a group having the formula -(CH2)m-C(O)-Z wherein Z is selected from OR5 and -N(R6)(R7) when m is 1 or 0 and when m is 0, Z can be the group -C(O)-OR8, R3 is selected from the group consisting of hydrogen, an aliphatic group having 1-18 carbon atoms, an araliphatic group having 7-15 and an alkanoyl group having from 2-18 carbon atoms, R4 is selected from the group consisting of hydrogen, an alkyl group having 1-16 carbon atoms and phenyl, R5 is selected from the group consisting of an alkyl group having 1-18 carbon atoms, a cycloalkyl group having 5-12 carbon atoms, allyl, benzyl, phenyl and a group of R, R6 and R7, may be the same or different, and each is selected from the group consisting of hydrogen, an alkyl group having 1-8 carbon atoms, a cycloalkyl group having 5-12 carbon atoms, an alkaryl group having 6-10 carbon atoms, an aralkyl group having 7-15 carbon atoms, and additionally R6 and R7, together with the N-atom to which they are attached, can form a 5-7 membered ring consisting of pyrrolidine, piperidine and homopiperidine, R8 is selected from the group consisting of an alkyl group having 1-18 carbon atoms, phenyl and benzyl, and B is a divalent alkylene group having 1-10 carbon atoms, and Y is selected from -O- and -NH-.

Composés à base de mélamine renfermant plusieurs fractions de 2,2,6,6-tétraalkylpipéridine, utiles comme photostabilisateurs dans les polymères organiques. Les composés sont de formule (voir fig. I), où : R est le groupe (voir fig. II); R1 est choisi parmi un hydrogène et un groupe alkyle de 1-5 atomes de carbon; R2 est choisi parmi un hydrogène, un groupe oxy, hydroxyle, alkyle lié à un méthylène, à chaîne droite ou ramifiée, de 1-18 atomes de carbone, alcanoyle de 2-18 atomes de carbone, alcényle de 3-4 atomes de carbone, alcénoyle de 3-6 atomes de carbone, alcynyle de 3-6 atomes de carbone, cyanométhyle, 2,3-époxypropyle, benzyle ou alkylbenzyle de 7-15 atomes de carbone, un groupe de formule -CH2CH(OR3)-R4, et un groupe de formule -(CH2)m-C(O)-Z, où Z est choisi parmi OR5 et -N(R6)(R7) lorsque m est 1 ou 0, et, lorsque m est 0, Z peut être le groupe -C(O)-OR8; R3 est choisi parmi un hydrogène, un groupe aliphatique de 1-18 atomes de carbone, un groupe araliphatique de 7-15 atomes de carbone et un groupe alcanoyle de 2-18 atomes de carbone; R4 est choisi parmi un hydrogène, un alkyle de 1-16 atomes de carbone et un phényle; R5 est choisi parmi un groupe alkyle de 1-18 atomes de carbone, cycloalkyle de 5-12 atomes de carbone, allyle, benzyle, phényle et un groupe de R; R6 et R7 peuvent être identiques ou différents, chacun étant choisi parmi un hydrogène, un groupe alkyle de 1-8 atomes de carbone, cycloalkyle de 5-12 atomes de carbone, alkaryle de 6-10 atomes de carbone et aralkyle de 7-15 atomes de carbone; de plus, R6 et R7 peuvent former ensemble, avec l'atome de N auquel ils sont liés, un cycle à 5-7 chaînons, soit une pyrrolidine, une pipéridine ou une homopipéridine; R8 est choisi parmi un groupe alkyle de 1-18 atomes de carbone, phényle ou benzyle; enfin, B est un groupe alkylène divalent de 1-10 atomes de carbone, et Y est choisi parmi -O- et -NH-.

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