Block oligomers containing...

Details Block oligomers containing... Block oligomers containing...

1999-11-18

2001-01-23

Sanders, Kriellion (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S097000, C544S113000, C544S198000, C544S219000, C544S220000, C252S401000, C252S403000

Reexamination Certificate

active

06177491

ABSTRACT:

The present invention relates to block oligomers containing 1-hydrocarbyloxy-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.
The stabilization of synthetic polymers with derivatives of 2,2,6,6-tetramethylpiperidine has been described for example in U.S. Pat. Nos. 4,086,204, 4,331,586, 4,335,242, 4,234,707, 4,459,395, 4,492,791, 5,204,473, EP-A 53 775, EP-A-357 223, EP-A-377 324, EP-A-462 069, EP-A-782 994 and GB-A-2 301 106.
The present invention relates in particular to a compound of the formula (I)
wherein n is a number from 2 to 14;
the radicals R
1
are independently of one another hydrogen or a hydrocarbyl radical or —O—R, is oxyl; the radicals R
2
are independently of one another C
2
-C
12
alkylene, C
4
-C
12
alkenylene, C
5
-C
7
cycloalkylene, C
5
-C
7
cycloalkylenedi(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
the radicals R have independently of one another 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
1
as a hydrocarbyl radical of preferably 1 to 18 carbon atoms is e.g. C
1
-C
18
alkyl, C
5
-C
18
alkenyl, C
5
-C
18
alkynyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by C
1
-C
4
alkyl; C
5
-C
12
cycloalkenyl unsubstituted or substituted by C
1
-C
4
alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms or C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by C
1
-C
4
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. R
1
is preferably C
1
-C
12
alkyl, e.g. C
6
-C
12
alkyl, in particular heptyl or octyl. R
6
is preferably C
1
-C
8
alkyl, in particular C
1
-C
4
alkyl. One of the preferred meanings of A is C
1
-C
4
alkyl.
An example 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 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 cyclododecyl. Unsubstituted or substituted cyclohexyl is preferred.
A preferred example of a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms is 1,2,3,4-tetrahydronaphthenyl.
A preferred example of C
5
-C
12
cycloalkenyl unsubstituted or substituted by C
1
-C
4
alkyl is cyclohexenyl.
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.
A preferred example of C
5
-C
18
alkynyl is octynyl.
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.
Examples of alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, hexoxycarbonyl, heptoxycarbonyl, octoxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl and dodecyloxycarbonyl.
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 preferred example of (C
5
-C
12
cycloalkyl)aminocarbonyl is cyclohexylaminocarbonyl. (C
5
-C
7
cycloalkyl)aminocarbonyl is preferred.
A particularly preferred example of (C
7
-C
9
phenylalkyl)aminocarbonyl is benzylaminocarbonyl.
Examples of alkylene containing not more than 12 carbon atoms are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, octamethylene

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