Derivatives of N-hals-substituted amic acid hydrazides

A process of stabilizing a synthetic or natural polymer subject to degradative effects of heat or light comprising mixing with the polymer composition an amount effective to stabilize the polymer composition against the degradative effects of heat or light of a compound having the formula:

• ##STR73## wherein R is hydrogen, oxyl, hydroxy, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, substituted or unsubstituted aliphatic acyl of 2-20 carbons, substituted or unsubstituted alicyclic acyl of 7-16 carbons, substituted or unsubstituted aryl acyl of 7-11 carbons, substituted or unsubstituted araliphatic acyl of 8-22 carbons, --C(.dbd.O)N(R.sup.6) (R.sup.7), --(C(.dbd.O)).sub.a O--R.sup.8, --(CH.sub.2).sub.a C(.dbd.O)O--R.sup.9 or
• --(CH.sub.2 --CH(R.sup.1)--O).sub.b --R.sup.10 ;
• n is 1 or 2;
• a is 1 or 2;
• b is an integer of 2-50;
• R.sup.2 is hydrogen or lower alkyl of 1-4 carbons;
• R.sup.2 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, 2-cyanoethyl or a radical of the formula:
• ##STR74## where R and R.sup.1 are a previously defined;
• R.sup.3 is a direct bond, a substituted or unsubstituted aliphatic diradical of 1-20 carbons, a substituted or unsubstituted aryl diradical of 6-12 carbons, a substituted or unsubstituted alicyclic diradical of 5-12 carbons or a substituted or unsubstituted araliphatic diradical of 7-22 carbons, where the diradical may contain 1-6 --O--, --S-- or --NH-- heteratoms with the proviso that multiple heteroatoms must be separated from each other and the diradical ends by at least one carbon atom;
• R.sup.2 and R.sup.3 may be linked together to form a 5-membered lactam ring;
• R.sup.4 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons or substituted or unsubstituted araliphatic of 7-22 carbons;
• when n is 1, R.sup.5 is --N.dbd.C(R.sup.11)(R.sup.12), --N (R.sup.13 )(R.sup.14) or --N(R.sup.6) --Q--R.sup.15,
• when n is 2, R.sup.5 is --N(R.sup.6)--Q--R.sup.17 --Q--N(R.sup.6)--;
• Q is --C(.dbd.O)--, --C(.dbd.O) --O--, --C(.dbd.O)--N(R.sup.4)--, --C(.dbd.S)--N(R.sup.4)-- or --S(.dbd.O).sub.2 --, in which R.sup.4 is as previously defined;
• R.sup.6 and R.sup.7 are independently hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons or substituted or unsubstituted araliphatic of 7-22 carbons;
• R.sup.8 is substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons or substituted or unsubstituted araliphatic of 7-22 carbons;
• R.sup.9 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons or substituted or unsubstituted araliphatic of 7-22 carbons;
• R.sup.10 is hydrogen or aliphatic of 1-4 carbons;
• R.sup.11 and R.sup.12 are independently hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons or substituted or unsubstituted araliphatic of 7-22 carbons;
• R.sup.11 and R.sup.12 may be linked together to form a substituted or unsubstituted alicyclic ring of 5-12 carbons or may be linked together through an --O--, --S-- or --NH-- heteratom to form a heterocyclic ring of 5-12 atoms wherein the --NH-- may be substituted by lower alkyl of 1-4 carbons;
• R.sup.13 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons or substituted or unsubstituted araliphatic of 7-22 carbons, substituted or unsubstituted aryl of 6-14 carbons, where the R.sup.13 substituents are chloro, bromo, cyano, hydroxy, epoxy, alkyl of 1-20 carbons, cycloalkyl of 5-12 carbons, aryl of 6-14 carbons, aralkyl of 7-22 carbons, alkoxy of 1-20 carbons, cycloalkoxy of 5-12 carbons, aryloxy of 6-14 carbons, aralkoxy of 7-15 carbons, aliphatic acyloxy of 2-20 carbons, alicyclic acyloxy of 6-13 carbons, aryl acyloxy of 7-15 carbons, alkylthio of 1-12 carbons, trialkoxysilyl of 3-12 carbons or araliphatic acyloxy of 8-16 carbons, wherein any alkyl or cycloalkyl substituent group may contain isolated double bonds;
• R.sup.14 is substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted araliphatic of 7-22 carbons or substituted or unsubstituted aryl of 6-14 carbons, where the R.sup.14 substituents are chloro, bromo, cyano, hydroxy, epoxy, alkyl of 1-20 carbons, cycloalkyl of 5-12 carbons, aryl of 6-14 carbons, aralkyl of 7-22 carbons, alkoxy of 1-20 carbons, cycloalkoxy of 5-12 carbons, aryloxy of 6-14 carbons, aralkoxy of 7-15 carbons, aliphatic acyloxy of 2-20 carbons, alicyclic acyloxy of 6-13 carbons, aryl acyloxy of 7-15 carbons, alkylthio of 1-12 carbons, trialkoxysilyl of 3-12 carbons or araliphatic acyloxy of 8-16 carbons, wherein any alkyl or cycloalkyl substituent group may contain isolated double bonds;
• R.sup.15 is hydrogen, substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons or substituted or unsubstituted araliphatic of 7-22 carbons;
• when Q is --C(.dbd.O)--, R.sup.15 is also selected from 2-(3,5-dialkyl-4-hydroxyphenyl)ethyl of 13-21 carbons, 3,5-dialkyl-4-hydroxyphenyl of 11-19 carbons in which the alkyl groups are branched or unbranched alkyl of 1-8 carbons, 4-benzoyl-3-hydroxyphenoxymethyl, 2-alkylthioethyl of 3-20 carbons, alkylthiomethyl of 2-20 carbons, 2-(dialkylaminoalkylthio)ethyl of 5-30 carbons or R.sup.16 --NH--C(.dbd.O)--R.sup.3 --;
• when Q is --C(.dbd.O)--O--, R.sup.15 is also selected from 2,2,6,6-tetramethyl-4-piperidinyl, in which the piperidinyl nitrogen is unsubstituted or substituted with methyl, ethyl, allyl, oxyl, hydroxyl, benzyl, benzoyl or acetyl;
• 2-(3-hydroxy-4-benzoylphenoxy) ethyl;
• 2-acryloyloxyethyl;
• 2-methacryloyloxyethyl;
• 2-(3-hydroxy-4-benzotriazol-2-ylphenoxy) ethyl;
• 3-(3-benzotriazol-2-yl-4-hydroxyphenyl)propyl, in which the benzotriazolyl group may be substituted in the 5 position with chlorine, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl and the phenyl group may be substituted ortho to the hydroxy group with an alkyl group of 1-12 carbons or an aralkyl group of 9-12 carbons;
• 3-(3,5-dialkyl-4-hydroxyphenyl)ethyl of 13-21 carbons, 2-(3,5-dialkyl-4-hydroxyphenyl)propyl of 14-22 carbons or 2-[3-(3,5-dialkyl-4-hydroxyphenyl)propionyloxy]thyl of 16-24 carbons, in which the alkyl groups are branched or unbranched alkyl of 1-8 carbons;
• with the proviso that when Q is --(C.dbd.O)--O--, R.sup.15 is not hydrogen;
• R.sup.16 is substituted or unsubstituted aliphatic of 1-20 carbons, substituted or unsubstituted alicyclic of 5-12 carbons, substituted or unsubstituted aryl of 6-14 carbons, substituted or unsubstituted araliphatic of 7-22 carbons, 3,5-dialkyl-4-hydroxyphenyl of 11-19 carbons in which the alkyl groups are independently branched or unbranched alkyl of 1-8 carbons or 2,2,6,6-tetramethyl-4-piperidinyl, in which the nitrogen may be substituted with methyl, ethyl, allyl, oxyl, hydroxyl, benzyl, benzoyl or acetyl;
• and
• R.sup.17 is a substituted or unsubstituted aliphatic diradical of 1-20 carbons, substituted or unsubstituted aryl diradical of 6-12 carbons, substituted or unsubstituted alicyclic diradical or 5-12 carbons or substituted or unsubstituted araliphatic diradical of 7-22 carbons, where the diradicals may contain 1-6 --O--, --S-- or --NH-- heteroatoms, with the proviso that multiple heteroatoms must be separated from each other and the diradical end by at least one carbon atom;
• substituents for any of R, R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.11, R.sup.12, R.sup.15, R.sup.16 or R.sup.17 are independently selected from one or more of chloro, bromo, alkyl of 1-8 carbons, alkoxy of 1-8 carbons, phenoxy, cyano, hydroxy, epoxy, carboxy, alkoxycarbonyl of 2-6 carbons, alkanoyloxy of 1-4 carbons, alkanoyl of 1-4 carbons, acryloyl, acryloyloxy, methacryloyl, methacryloyloxy, hydroxymethyl, 2-hydroxyethyl, alkylthio of 1-4 carbons or trialkoxysilyl of 3-12 carbons, with the proviso that when Q is --C(.dbd.O)--, R.sup.15 may not be substituted with a carboxy group;
• and
• where R is 2-hydroxy substituted aliphatic or 2-hydroxy substituted alicyclic, substituents for R are also selected from aliphatic of 1-20 carbons, alicyclic of 5-12 carbons, aryl of 6-14 carbons, araliphatic of 7-22 carbons, alkoxy of 1-20 carbons, cycloalkoxy of 5-12 carbons, aryloxy of 6-14 carbons, aralkoxy of 7-15 carbons, aliphatic acyloxy of 2-20 carbons, alicyclic acyloxy of 6-13 carbons, aryl acyloxy of 7-15 carbons or araliphatic acyloxy of 8-16 carbons, where any alkyl or cycloalkyl substituent group of the 2-hydroxy substituted group may contain isolated double bonds.