Polysilane stabitizers containing sterically hindered amine...

Details Polysilane stabitizers containing sterically hindered amine... Polysilane stabitizers containing sterically hindered amine...

2001-10-18

2003-03-25

Dawson, Robert (Department: 1712)

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

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C524S266000, C525S100000, C528S027000, C528S028000, C556S401000, C556S413000, C556S424000, C556S430000, C556S431000

Reexamination Certificate

active

06538055

ABSTRACT:

The present invention relates to compounds containing a polysilane backbone and 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.
Stabilizers containing a polysiloxane backbone and 2,2,6,6-tetramethyl-4-piperidyl groups are described for example in U.S. Pat. Nos. 4,234,700, 5,134,233, 5,219,905, 5,514,738, 5,561,179, GB-A-2,295,619 and U.S. Pat. No. 5,726,226. Some polysilane stabilizers are disclosed in EP-A-836,635. The autoxidation of poly(hydrosilane)s is described by C. Chatgilialoglu et al. in Organometallics 1998,17, 216914 2176.
In more detail, the present invention relates to a compound containing a polysilane backbone with more than two Si atoms and a group of the formula
wherein R is hydrogen, C
1
-C
8
alkyl, —O
•
, —OH, —CH
2
CN, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; or C
1
-C
8
acyl.
The backbone corresponds for example to the formula
with X
1
, X
2
, m, n, p and q as defined below.
A backbone which contains only Si atoms (m and n are zero) is especially preferred.
The present invention relates in particular to a compound of the formula (I)
in which
p is a number from 2 to 100 and q is zero or a number from 2 to 90;
m and n independently of one another are zero or 1;
R
1
and R
2
independently of one another are a group of the formula (II) or (III) as defined below, or hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; phenyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy;
X
1
and X
2
independently of one another are C
2
-C
12
alkylene;
A
1
is a group of the formula (II) or (III)
 wherein
R
3
is a direct bond or C
1
-C
12
alkylene,
R
4
, R
6
, R
7
and R
8
independently of one another are —O— or >N—R
11
with R
11
being hydrogen, C
1
-C
8
alkyl, C
5
-C
12
cycloalkyl or a group of the formula (IV),
R
5
, R
9
, R
10
and R
12
independently of one another are hydrogen, C
1
-C
8
alkyl, —O
•
, —OH, —CH
2
CN, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl ; or C
1
-C
8
acyl,
X
3
is a direct bond or >C═O, and
X
4
is C
2
-C
12
alkylene;
A
2
is a group of the formula (II) or (III), or hydrogen, C
1
-C
12
alkyl, C
5
-C
2
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; and
each of the radicals R
1
, R
2
, X
1
, X
2
, A
1
and A
2
as well as each of the variables m and n can have the same or a different meaning in the individual recurring units of the formula (I); and when the compounds of the formula (I) are copolymeric, they can have a random, alternate or block distribution of the individual recurring units.
One of the preferred embodiments of the present invention relates to a compound of the formula (I) wherein the structural unit of the formula (A)
is different from the structural unit of the formula (B).
Example of alkyl containing up to 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 R
1
and R
2
is C
1
-C
12
alkyl. One of the preferred meanings of R
5
, R
9
, R
10
and R
12
is C
1
-C
4
alkyl, in particular methyl. One of the preferred meanings of R
11
is C
1
-C
4
alkyl.
Examples of alkoxy containing not more than 18 carbon atoms are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy and octadecyloxy. C
6
-C
12
Alkoxy, in particular heptoxy or octoxy, is one of the preferred meanings of R
5
, R
9
, R
10
and R
12
.
Examples of alkenyl containing not more than 6 carbon atoms are allyl, 2-methylallyl, butenyl and hexenyl. Alkenyls in which the carbon atom in the 1-position is saturated are preferred, and allyl is particularly preferred.
Examples of C
5
-C
12
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy are cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, methoxycyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl, cyclodecyl and cyclododecyl. Cyclohexyl is preferred.
Examples of C
5
-C
12
cycloalkoxy are cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclodecyloxy and cyclododecyloxy. C
5
-C
8
Cycloalkoxy, in particular cyclopentoxy and cyclohexoxy, is preferred.
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 unsubstituted or substituted on the phenyl by 1. 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy are benzyl, methylbenzyl, methoxybenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl and 2-phenylethyl. Benzyl is preferred.
Examples of acyl (aliphatic, cycloaliphatic or aromatic) containing not more than 8 carbon atoms are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl and octanoyl. C
1
-C
8
Alkanoyl and benzoyl are preferred. Acetyl is especially preferred.
Examples of alkylene containing not more than 12 carbon atoms are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, decamethylene and dodecamethylene. R
3
and X
4
are preferably C
2
-C
10
alkylene. C
3
-C
10
alkylene is a particularly preferred meaning of R
3
and X
4
.
p is preferably a number from 2 to 50, in particular 2 to 20. q is preferably zero or a number from 2 to 45, in particular 2 to 18. According to a particularly preferred embodiment, q varies from 0 to 90% of the sum of p+q. The p:q molar ratio is for example 1:9 to 9:1 or 1:4 to 4:1 or 1:2 to 2:1.
R
1
and R
2
independently of one another may be for example C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; phenyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; and A
2
may be for example hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy.
R
1
may be for example hydrogen or a group of the formula (II) or (III); R
2
may be for example hydrogen, a group of the formula (II) or (III), C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; phenyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; and A
2
may be for example hydrogen, a group of the formula (II) or (III), C
1
-C12alkyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy.
R
5
, R
9
, R
10
and R
12
independently of one another are preferably hydrogen, C
1
-C
4
alkyl, —OH, C
6
-C
12
alkoxy, C
5
-C
8
cycloalkoxy, allyl, benzyl or acetyl, in particular hydrogen or C
1
-C
4
alkyl such as methyl.
R
1
and R
2
independently of one another are preferably C
1
-C
16
alkyl or phenyl. A preferred meaning of R
2
is also hydrogen.
The variables m and n are preferably zero.
Preferred compounds of the formula (I) are those wherein m and n are zero and R
1
is hydrogen or a group of the formula (II).
X
3
is preferably a direct bond.
Preferred compounds of the formula (I) are also those wherein

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