Triazine compounds containing...

Details Triazine compounds containing... Triazine compounds containing...

1999-10-25

2001-04-24

Hoke, Veronica P. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

Reexamination Certificate

active

06221937

ABSTRACT:

The present invention relates to triazine compounds containing 2,2,6,6-tetramethyl-4-piperidyl groups, to their use as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, particularly synthetic polymers, and to the organic materials thus stabilized. Furthermore, the present invention relates to specific block oligomers as well as to a mixture of block oligomers with a narrow molecular weight distribution, and to a method of the preparation thereof.
The stabilization of synthetic polymers with derivatives of 2,2,6,6-tetramethylpiperidine has been described for example in U.S. Pat. No. 4,086,204, U.S. Pat. No. 4,331,586, U.S. Pat. No. 4,335,242, U.S. Pat. No. 4,234,707, U.S. Pat. No. 5,198,546, U.S. Pat. No. 5,610,211, U.S. Pat. No. 5,449,776, U.S. Pat. No. 5,047,531, U.S. Pat. No. 4,468,488, U.S. Pat. No. 4,415,689, EP-A-357 223, EP-A-377 324 and Derwent 86-248801/38.
The present invention relates in particular to a product of the formula (I)
in which n is a number from 2 to 14;
the radicals R
1
are independently of one another hydrogen, C
1
-C
8
alkyl, C
1
-C
8
hydroxyalkyl, —CH
2
CN, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; C
1
-C
8
acyl, (C
1
-C
8
alkoxy)carbonyl or (C
5
-C
12
cycloalkoxy)carbonyl;
R
2
is C
2
-C
12
alkylene, C
4
-C
12
alkenylene, C
5
-C
7
cycloalkylene, C
5
-C
7
cycloalkylene-di(C
1
-C
4
alkylene), C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene), phenylenedi(C
1
-C
4
alkylene) or C
4
-C
12
alkylene interrupted by 1,4-piperazinediyl, —O— or >N-X
1
with X
1
being C
1
-C
12
acyl or (C
1
-C
12
alkoxy)carbonyl or having one of the definitions of R
4
given below except hydrogen; or R
2
is a group of the formula (a), (b) or (c);
with m being 2 or 3,
X
2
being C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; and
the radicals X
3
being independently of one another C
2
-C
12
alkylene;
the radicals A are independently of one another C
1
-C
8
acyl, (C
1
-C
8
alkoxy)carbonyl, (C
5
-C
12
cycloalkoxy)carbonyl, (C
1
-C
8
alkyl)aminocarbonyl, (C
5
-C
12
cycloalkyl)aminocarbonyl, (C
7
-C
9
phenylalkyl)aminocarbonyl, C
1
-C
8
alkyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; or —CH
2
CN;
B is OR
3
, —N(R
4
)(R
5
) or a group of the formula (II);
R
3
, R
4
and R
5
, which are identical or different, are hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; C
3
--C
18
alkenyl, phenyl which is unsubstituted, or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; tetrahydrofurfuryl or C
2
-C
4
alkyl which is substituted in the 2, 3 or 4 position by —OH, C
1
-C
8
alkoxy, di(C
1
-C
4
alkyl)amino or a group of the formula (III);
with Y being —O—, —CH
2
—, —CH
2
CH
2
— or >N—CH
3
,
or —N(R
4
)(R
5
) is additionally a group of the formula (III);
X is —O— or >N-R
6
;
R
6
is hydrogen, C
1
-C
18
alkyl, C
3
-C
18
alkenyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; tetrahydrofurfuryl, a group of the formula (IV),
or C
2
-C
4
alkyl which is substituted in the 2, 3 or 4 position by —OH, C
1
-C
8
alkoxy, di(C
1
-C
4
alkyl)amino or a group of the formula (III); and
R has one of the meanings given for R
6
;
with the proviso that in the individual recurrent units of the formula (I), each of the radicals B, R, R
1
and R
2
has the same or a different meaning.
In the individual recurring units of the formula (I), each of the radicals B, R, R
1
and R
2
has preferably the same meaning.
In the formula (I), the radical R and the radical
can have a random distribution or a block distribution.
R is preferably different from hydrogen, when A is C
1
-C
8
alkyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; or —CH
2
CN, in particular C
1
-C
8
alkyl.
Examples of alkyl containing not more than 18 carbon atoms are methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, t-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, t-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl. One of the preferred meanings of A is C
1
-C
4
alkyl.
An example of C
2
-C
8
hydroxyalkyl and of C
2
-C
4
alkyl substituted by —OH is 2-hydroxyethyl.
Examples of C
2
-C
4
alkyl substituted by C
1
-C
8
alkoxy, preferably by C
1
-C
4
alkoxy, in particular methoxy or ethoxy, are 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-butoxypropyl, 3-octoxypropyl and 4-methoxybutyl.
Examples of C
2
-C
4
alkyl substituted by di(C
1
-C
4
alkyl)amino, preferably by dimethylamino or diethylamino, are 2-dimethylaminoethyl, 2-diethylaminoethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl, 3-dibutylaminopropyl and 4-diethylaminobutyl.
The group of the formula (III) is preferably
Preferred examples of C
2
-C
4
alkyl substituted by a group of the formula (III) are groups of the formula
The group
is particularly preferred.
Examples of alkoxy containing not more than 8 carbon atoms are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy or octoxy.
Examples of C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl are cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl, cyclodecyl and cyclodecyl. Unsubstituted or substituted cyclohexyl is preferred.
Examples of alkenyl containing not more than 18 carbon atoms are allyl, 2-methylallyl, butenyl, hexenyl, undecenyl and octadecenyl. Alkenyls in which the carbon atom in the 1-position is saturated are preferred, and allyl is particularly preferred.
An example of C
3
-C
6
alkynyl is 2-butynyl.
Examples of phenyl substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy are methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, di-t-butylphenyl, 3,5-di-t-butyl-4-methylphenyl, methoxyphenyl, ethoxyphenyl and butoxyphenyl.
Examples of C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl are benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl and 2-phenylethyl. Benzyl is preferred.
Examples of acyl (aliphatic, cycloaliphatic or aromatic) containing not more than 12 carbon atoms are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl and benzoyl. C
1
-C
8
Alkanoyl and benzoyl are preferred. Acetyl is especially preferred. One of the preferred meanings of A is C
1
-C
2
acyl, in particular formyl or acetyl.
Examples of alkoxycarbonyl with the alkoxy group having up to 12 carbon atoms are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, hexoxycarbonyl, heptoxycarbonyl, octoxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl and dodecyloxycarbonyl. One of the preferred meanings of A is (C
1
-C
2
alkoxy)carbonyl.
A particularly preferred example of (C
5
-C
12
cycloalkoxy)carbonyl is cyclohexoxycarbonyl. (C
5
-C
7
cycloalkoxy)carbonyl is preferred.
Examples of (C
1
-C
8
alkyl)aminocarbonyl are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butylaminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl and octylaminocarbonyl. (C
1
-C
4
alkyl)aminocarbonyl is preferred.
A particularly

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