US 4,396,735 A · Synergistic light stabilizer compositions for synthetic resins and resin compositions containing the same

Abstract

Light stabilizers for synthetic resin compositions and synthetic resin compositions containing such stabilizers are provided, comprising (1) at least one hindered heterocyclic amine having the formula: ##STR1## wherein: X is a bivalent linking radical forming with the ring structure ##STR2## a nitrogen-containing heterocyclic ring having from five to seven ring atoms, preferably piperidine; R.sub.1 and R.sub.2 are each selected from the group consisting of lower alkyl, preferably methyl, and R.sub.1 and R.sub.2 taken together as pentylene (CH.sub.2).sub.5 ; R.sub.3 and R.sub.4 are each selected from the group consisting of lower alkyl, and R.sub.3 and R.sub.4 taken together as one of butylene--(CH.sub.2).sub.4, pentylene--(CH.sub.2).sub.5, and CH.sub.2 --C(CH.sub.3).sub.2 --NH--C(CH.sub.3).sub.2 --CH.sub.2 --; n is 1 or 2; and when n is 1, Y.sub.1 is selected from the group consisting of hydrogen, O.sup..cndot., OH, alkyl, alkenyl, alkynyl, aralkyl and acyl having from one to about thirty carbon atoms; and when n is 2, Y.sub.1 is selected from the group consisting of alkylene, alkenylene, alkynylene, cycloalkylene and aralkylene having from one to about thirty carbon atoms; together with (2) at least one heterocyclic acid hydrazide having the formula: ##STR3## wherein: R is selected from the group consisting of hydrogen, alkyl, aryl and such groups having hydroxyl, carboxylic acid ester, oxyether and carbonyl groups having from one to about thirty carbon atoms; ##STR4## is the residue of a dicarboxylic or tetracarboxylic acid, wherein Z is selected from the group consisting of alkylene, alkenylene, cycloalkylene, alkylcycloalkylene, arylene and alkylarylene having from one to about thirty carbon atoms, and such radicals bearing free carboxylic acid or carboxylic acid ester groups; and m is 1 or 2. In such combinations, the heterocyclic acid hydrazide, which alone is not a light-stabilizer, synergizes the stabilizing effectiveness of the hindered heterocyclic amine.

Claims29

Dependent claims

A light stabilizer composition for organic polymeric materials comprising:

(1) at least one hindered heterocyclic amine having the formula:
##STR241## wherein:
X is a bivalent linking radical including at least one up to four ring carbon atoms completing the ring structure:
##STR242## as a heterocyclic ring having from five to seven ring atoms of which at least one is nitrogen and from three to six are carbon;
and a substituent selected from the group consisting of Z;
O--Z;
NH--Z;
##STR243## wherein Z is the residue of an acid selected from the group consisting of carboxylic acids having from one to thirty carbon atoms, carbonic acid and inorganic oxyacids of phosphorus, silicon and boron and R" is hydrogen or lower alkyl;
and
.dbd.Z.sub.4 wherein Z.sub.4 is a bivalent group selected from the group consisting of:
##STR244## wherein X.sub.4 is hydrogen or methyl;
and
B is selected from the group consisting of alkyl, epoxy alkyl, alkenyl and cycloalkyl having from one to about eighteen carbon atoms, and ##STR245## in which the alkylene has from one to about ten carbon atoms;
R.sub.1 and R.sub.2 are each selected from the group consisting of lower alkyl and R.sub.1 and R.sub.2 taken together as pentylene (CH.sub.2).sub.5 ;
R.sub.3 and R.sub.4 are each selected from the group consisting of lower alkyl, and R.sub.3 and R.sub.4 taken together as one of butylene--(CH.sub.2).sub.4, pentylene--(CH.sub.2).sub.5, and CH.sub.2 --C(CH.sub.3).sub.2 --NH--C(CH.sub.3).sub.2 --CH.sub.2 --;
n is 1 or 2;
and
when n is 1, Y.sub.1 is selected from the group consisting of hydrogen;
O.sup..cndot., OH, alkyl, alkenyl, alkynyl, aralkyl and acyl having from one to about thirty carbon atoms;
and
when n is 2, Y.sub.1 is selected from the group consisting of alkylene, alkenylene, alkynylene, cycloalkylene and aralkylene having from one to about thirty carbon atoms;
and p1 (2) at least one heterocyclic acid hydrazide having the formula:
##STR246## wherein:
R is selected from the group consisting of hydrogen, alkyl, aryl and such groups having hydroxyl, carboxylic acid ester, oxyether and carbonyl groups having from one to about thirty carbon atoms;
##STR247## is the residue of a dicarboxylic or tetracarboxylic acid, wherein Z.sub.1 is selected from the group consisting of alkylene, alkenylene, cycloalkylene, alkylcycloalkylene, arylene and alkylarylene having from one to about thirty carbon atoms, and such radicals bearing free carboxylic acid or carboxylic acid ester groups;
and
m is 1 or 2,
the heterocyclic acid hydrazide being in an amount synergizing the stabilizing effectiveness of the hindered heterocyclic amine.

25 more elements

A light stabilizer composition

comprising
(1) at least one hindered heterocyclic amine having the formula:
##STR266## wherein A is alkylene completing the ring structure;
X is a bivalent linking radical including at least one up to four ring carbon atoms completing the ring structure ##STR267## as a heterocyclic ring having from five to seven ring atoms of which at least one is nitrogen and from three to six are carbon;
R.sub.1 and R.sub.2 are each selected from the group consisting of lower alkyl, and R.sub.1 and R.sub.2 taken together as pentylene (CH.sub.2).sub.5 ;
R.sub.3 and R.sub.4 are each selected from the group consisting of lower alkyl and R.sub.3 and R.sub.4 taken together as one of butylene--(CH.sub.2).sub.4, pentylene--(CH.sub.2).sub.5, and --CH.sub.2 --C(CH.sub.3).sub.2 --NH--C(CH.sub.3).sub.2 --CH.sub.2 --;
n is 1 or 2;
and
Y.sub.1 is selected from the group consisting of hydrogen, O.sup..cndot., OH, alkyl, alkenyl, alkynyl, aralkyl and acyl having from one to about thirty carbon atoms;
and
when n is 1, Y.sub.2 is selected from the group consisting of bivalent alkylene, alkenylene, alkynylene, cycloalkylene and arylkylene having from one to about thirty carbon atoms;
and when n is 2, Y.sub.2 is selected from the group consisting of trivalent alkylene, alkenylene, alkynylene, cycloalkylene and aralkylene having from one to about thirty carbon atoms;
together with
(2) at least one heterocyclic acid hydrazide having the formula:
##STR268## wherein:
R is selected from the group consisting of hydrogen, alkyl, aryl and such groups having hydroxyl, carboxylic acid ester, oxyether and carbonyl groups having from one to about thirty carbon atoms;
##STR269## is the residue of a dicarboxylic or tetracarboxylic acid, wherein Z.sub.1 is selected from the group consisting of alkylene, alkenylene, cycloalkylene, alkylcycloalkylene, arylene and alkylarylene having from one to about thirty carbon atoms, and such radicals bearing free carboxylic acid or carboxylic acid ester groups;
and
m is 1 or 2,
the heterocyclic acid hydrazide being in an amount synergizing the stabilizing effectiveness of the hindered heterocyclic amine.

17 more elements

Dependencies are inferred from the claim text.

Synergistic light stabilizer compositions for synthetic resins and resin compositions containing the same

Life of this patent

Synergistic light stabilizer compositions for synthetic resins and resin compositions containing the same

Life of this patent

Abstract

Claims29