US 5,106,891 AGranted

Light stabilized coating compositions containing a mixture of 2-hydroxyphenylbenzotriazole and 2-hydroxyphenyltriazine

AssigneeCiba-Geigy Corporation

InventorAndreas Valet

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Abstract

Coating compositions which, in addition to a 2-hydroxyphenylbenzotriazole UV absorber, also contain a UV absorber belonging to the group of the 2-hydroxyphenyltriazines, 2-hydroxybenzophenones and/or, in addition to a 2-hydroxyphenyltriazine, also contain a 2-hydroxybenzophenone and/or oxanilide are described.

Claims17

Dependent claims

A coating composition which contains, as the UV absorber, a mixture of at least one 2-hydroxyphenylbenzotriazole and at least one 2-hydroxyphenyltriazine, wherein

the 2-hydroxyphenylbenzotriazole has the formula 1a or 1b ##STR39## in which in formula 1a or 1b R.sub.1 is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
R.sub.2 is hydrogen, halogen, alkyl having 1 to 18 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and
R.sub.3 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms;
with at least one of the radicals R.sub.1 and R.sub.2 being other than hydrogen;
T is hydrogen or alkyl having 1 to 6 carbon atoms,
T.sub.1 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms,
n is 1 or 2,
when n is 1, T.sub.2 is chlorine or a radical of the formula--OT.sub.3,
wherein T.sub.3 is hydrogen, alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups;
alkyl of 3 to 18 carbon atoms interrupted once or several times by --O-- and is unsubstituted or substituted by hydroxyl;
alkenyl which has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl;
phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula --CH.sub.2 CH(OH)--T.sub.7 or glycidyl;
where T.sub.7 is hydrogen, alkyl having 1 to 18 carbon atoms or phenyl, and
when n is 2, T.sub.2 is a radical of the formula --O--T.sub.9 --O--,
wherein T.sub.9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, alkylene which has 2 to 8 carbon atoms and is interrupted once or several times by --O--;
and
in which in formula 2
u is 1 or 2
r is an integer from 1 to 3
the substituents Y.sub.1 independently of one another are hydrogen, hydroxyl, halogenomethyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms or halogen,
when u is 1, Y.sub.2 is alkyl having 1 to 18 carbon atoms, alkyl which has 1 to 12 carbon atoms and is substituted by --COOH, --COOY.sub.8, --CONH.sub.2, --CONHY.sub.9, --CONY.sub.9 Y.sub.10, --CN, --OCOY.sub.11 or mixtures thereof;
alkyl which has 4 to 20 carbon atoms which is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms;
alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl which has 1 to 5 carbon atoms in the alkyl moiety and is unsubstituted or substituted by hydroxyl, chlorine and/or methyl;
--COY.sub.12 or --SO.sub.2 Y.sub.13,
wherein Y.sub.8 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl which has 3 to 20 carbon atoms and is interrupted by one or more oxygen atoms or said alkyl substituted by hydroxyl;
alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety,
Y.sub.9 and Y.sub.10 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cycloalkyl having 5 to 12 carbon atoms,
Y.sub.11 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl,
Y.sub.12 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, and
Y.sub.13 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical;
and when u is 2, Y.sub.2 is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylylene, alkylene which has 3 to 20 carbon atoms and is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl;
--CH.sub.2 CH(OH)CH.sub.2 --O--Y.sub.15 --OCH.sub.2 CH(OH)CH.sub.2 -- or --(CH.sub.2).sub.m --CO.sub.2 --Y.sub.18 --OCO--(CH.sub.2).sub.m --, in which m is 1, 2 or 3,
wherein Y.sub.15 is alkylene having 2 to 10 carbon atoms, phenylene or a group phenylene-M-phenylene in which M is --O--, --S--, --SO.sub.2 --, --CH.sub.2 -- or --C(CH.sub.3).sub.2 --, and
Y.sub.18 is alkylene having 2 to 10 carbon atoms or alkylene which has 4 to 20 carbon atoms and is interrupted once or several times by oxygen.

31 more elements

Dependencies are inferred from the claim text.

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Abstract

A coating composition which contains, as the UV absorber, a mixture of at least one 2-hydroxyphenylbenzotriazole and at least one 2-hydroxyphenyltriazine, wherein

the 2-hydroxyphenylbenzotriazole has the formula 1a or 1b ##STR39## in which in formula 1a or 1b R.sub.1 is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
R.sub.2 is hydrogen, halogen, alkyl having 1 to 18 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and
R.sub.3 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms;
with at least one of the radicals R.sub.1 and R.sub.2 being other than hydrogen;
T is hydrogen or alkyl having 1 to 6 carbon atoms,
T.sub.1 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms,
n is 1 or 2,
when n is 1, T.sub.2 is chlorine or a radical of the formula--OT.sub.3,
wherein T.sub.3 is hydrogen, alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups;
alkyl of 3 to 18 carbon atoms interrupted once or several times by --O-- and is unsubstituted or substituted by hydroxyl;
alkenyl which has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl;
phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula --CH.sub.2 CH(OH)--T.sub.7 or glycidyl;
where T.sub.7 is hydrogen, alkyl having 1 to 18 carbon atoms or phenyl, and
when n is 2, T.sub.2 is a radical of the formula --O--T.sub.9 --O--,
wherein T.sub.9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, alkylene which has 2 to 8 carbon atoms and is interrupted once or several times by --O--;
and
in which in formula 2
u is 1 or 2
r is an integer from 1 to 3
the substituents Y.sub.1 independently of one another are hydrogen, hydroxyl, halogenomethyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms or halogen,
when u is 1, Y.sub.2 is alkyl having 1 to 18 carbon atoms, alkyl which has 1 to 12 carbon atoms and is substituted by --COOH, --COOY.sub.8, --CONH.sub.2, --CONHY.sub.9, --CONY.sub.9 Y.sub.10, --CN, --OCOY.sub.11 or mixtures thereof;
alkyl which has 4 to 20 carbon atoms which is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms;
alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl which has 1 to 5 carbon atoms in the alkyl moiety and is unsubstituted or substituted by hydroxyl, chlorine and/or methyl;
--COY.sub.12 or --SO.sub.2 Y.sub.13,
wherein Y.sub.8 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl which has 3 to 20 carbon atoms and is interrupted by one or more oxygen atoms or said alkyl substituted by hydroxyl;
alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety,
Y.sub.9 and Y.sub.10 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cycloalkyl having 5 to 12 carbon atoms,
Y.sub.11 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl,
Y.sub.12 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, and
Y.sub.13 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical;
and when u is 2, Y.sub.2 is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylylene, alkylene which has 3 to 20 carbon atoms and is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl;
--CH.sub.2 CH(OH)CH.sub.2 --O--Y.sub.15 --OCH.sub.2 CH(OH)CH.sub.2 -- or --(CH.sub.2).sub.m --CO.sub.2 --Y.sub.18 --OCO--(CH.sub.2).sub.m --, in which m is 1, 2 or 3,
wherein Y.sub.15 is alkylene having 2 to 10 carbon atoms, phenylene or a group phenylene-M-phenylene in which M is --O--, --S--, --SO.sub.2 --, --CH.sub.2 -- or --C(CH.sub.3).sub.2 --, and
Y.sub.18 is alkylene having 2 to 10 carbon atoms or alkylene which has 4 to 20 carbon atoms and is interrupted once or several times by oxygen.

31 more elements