Synergistic stabilizer mixture

Details Synergistic stabilizer mixture Synergistic stabilizer mixture

1999-03-18

2002-04-02

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

06365651

ABSTRACT:

The present invention relates to a stabilizer system comprising two specific high-molecular-weight polyalkylpiperidine derivatives, to the use of this stabilizer system for stabilizing organic material, and to the organic material protected against thermal, oxidative or light-induced degradation by means of the stabilizer system mentioned. U.S. Pat. Nos. 4,692,486, 4,863,981, 4,957,953, WO-A-92/12 201, EP-A-449 685, EP-A-632 092, GB-A-2 267 499 and Research Disclosure 34549 (January 1993) describe stabilizer mixtures comprising two polyalkylpiperidine derivatives.
The present invention relates to a stabilizer mixture comprising a component a) and a component b), c), d), e), f) or g), where component a) is at least one compound of the formula I
in which
R
1
is C
1
-C
10
alkyl, C
5
-C
12
cycloalkyl, C
1
-C
4
alkyl-substituted C
5
-C
12
cycloalkyl, phenyl or C
1
-C
10
alkyl-substituted phenyl,
R
2
is C
3
-C
10
alkylene,
R
3
is hydrogen, C
1
-C
8
alkyl, O, —CH
2
CN, C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl, C
7
-C
9
phenylalkyl which is substituted on the phenyl radical by C
1
-C
4
alkyl; or C
1
-C
8
acyl and,
n
1
is a number from 1 to 50;
component b) is at least one compound of the formula (II)
in which R
4
, R
6
, R
7
and R
8
, independently of one another, are hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, C
1
-C
4
-alkyl-substituted C
5
-C
12
cycloalkyl, phenyl, phenyl which is substituted by —OH and/or C
1
-C
10
alkyl; C
7
-C
9
phenylalkyl, C
7
-C
9
phenylalkyl which is substituted on the phenyl radical by —OH and/or C
1
-C
10
alkyl; or a group of the formula III
R
5
is C
2
-C
18
alkylene, C
5
-C
7
cycloalkylene or C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene), or the radicals R
4
, R
5
and R
6
, together with the nitrogen atoms to which they are bonded, perform a 5- to 10-membered heterocyclic ring, or
R
7
and R
8
, together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring,
R
9
is as defined for R
3
,
n
2
is a number from 2 to 50, and
at least one of the radicals R
4
, R
6
, R
7
and R
8
is a group of the formula (III);
component c) is a product obtainable by reacting a product, obtained by reaction of a polyamine of the formula IVa with cyanuric chloride, with a compound of the formula IVb
in which n
3
′, n
3
″ and n
3
′″, independently of one another are a number from 2 to 12, R
10
is hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl, and R
11
is as defined for R
3
;
component d) is at least one compound of the formula (V)
in which
R
12
is hydrogen or methyl,
R
13
is a direct bond or C
1
-C
10
alkylene and
n
4
is a number from 2 to 50;
component e) is at least one compound of the formulae (VIa) and (VIb)
in which n
5
and n
5
* independently of one another are a number from 2 to 50;
component f) is at least one compound of the formula (VI)
in which
R
14
and R
18
, independently of one another, are a direct bond or an —N(X
1
)—CO—X
2
—CO—N(X
3
)— group, where X
1
and X
3
, independently of one another, are hydrogen, C
1
-C
8
alkyl, C
5
-C
12
cycloalkyl, phenyl, C
7
-C
9
phenylalkyl or a group of the formula III,
X
2
is a direct bond or C
1
-C
4
alkylene,
R
15
is as defined for R
3
,
R
16
, R
17
, R
20
and R
21
, independently of one another, are hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl or phenyl,
R
19
is hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
9
phenylalkyl, phenyl or a group of the formula III, and
n
6
is a number from 1 to 50;
component g) is at least one compound of the formula (VIII)
in which
R
22
, R
23
, R
24
, R
25
and R
26
, independently of one another, are a direct bond or C
1
-C
10
alkylene,
R
27
is as defined for R
3
, and
n
7
is a number from 1 to 50.
Examples of alkyl having up to 30 carbon atoms are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, docosyl and triacontyl. One of the preferred meanings of R
3
, R
9
, R
11
, R
15
, R
17
, R
21
and R
27
is C
1
-C
4
alkyl, in particular methyl. One of the preferred meanings of R
16
and R
20
is C
1
-C
25
alkyl, in particular C
15
-C
25
alkyl, for example hexadecyl and C
18
-C
22
alkyl. One of the preferred meanings of R
19
is C
1
-C
25
alkyl, in particular octadecyl.
Examples of C
5
-C
12
cycloalkyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclododecyl. C
5
-C
8
cycloalkyl, in particular cyclohexyl, is preferred.
C
1
-C
4
Alkyl-substituted C
5
-C
12
cycloalkyl is, for example, methylcyclohexyl or dimethylcyclohexyl.
Phenyl which is substituted by —OH and/or C
1
-C
10
alkyl is, for example, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl or 3,5-di-tert-butyl-4-hydroxyphenyl.
Examples of C
7
-C
9
phenylalkyl are benzyl and phenylethyl.
C
7
-C
9
phenylalkyl which is substituted by —OH and/or alkyl with up to 10 carbon atoms on the phenyl radical is, for example, methylbenzyl, dimethylbenzyl, trimethylbenzyl, tert-butylbenzyl, or 3,5-di-tert-butyl-4-hydroxyphenyl.
Examples of C
3
-C
6
alkenyl are allyl, 2-methallyl, butenyl, pentenyl and hexenyl. Allyl is preferred.
C
1
-C
8
acyl is preferably C
1
-C
8
alkanoyl, C
3
-C
8
alkenoyl or benzoyl. Examples are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, octanoyl, benzoyl, acryloyl and crotonyl.
Examples of alkylene having up to 18 carbon atoms are methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, trimethylhexamethylene, octamethylene and decamethylene. R
5
is preferably hexamethylene, R
13
is preferably ethylene, R
22
and R
24
are preferably methylene, R
25
is preferably 2,2-dimethylethylene and R
26
is preferably 1,1-dimethylethylene.
An example of C
5
-C
7
cycloalkylene is cyclohexylene.
An example of C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene) is methylenedicyclohexylene.
If the radicals R
4
, R
5
and R
6
, together with the nitrogen atoms to which they are bonded, form a 5- to 10-membered heterocyclic ring, this is, for example,
A 6-membered heterocyclic ring is preferred.
If the radicals R
7
and R
8
, together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring, this is, for example, 1-pyrrolidyl, piperidino, morpholino, 1-piperazinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl, 5,5,7-trimethyl-1-homopiperazinyl or 4,5,5,7-tetramethyl-1-homopiperazinyl. Morpholino is particularly preferred.
One of the preferred meanings of R
16
and R
20
is phenyl.
X
2
and R
23
are preferably a direct bond.
X
1
, X
3
, R
3
, R
9
, R
11
, R
15
an d R
27
are preferably hydrogen.
n
1
is preferably 1-25, in particular 2-20 or 2-10.
n
2
is preferably 2-25.
n
3
′, n
3
″, n
3
′″ are preferably 2-4.
n
4
is preferably 2-25, in particular 2-20 or 2-10.
n
5
and n
5
* are preferably 2-25, in particular 2-20 or 2-10.
n
6
is preferably 1-25, in particular 1-20 or 1-10.
n
7
is preferably 1-25, in particular 1-20 or 1-10.
The compounds described as components a) to g) are essentially known (in some cases commercially available) and can be prepared by known processes, for example as described in U.S. Pat. Nos. 5,051,458, 4,086,204, 4,331,586, 4,477,615 and Chemical Abstracts- CAS No. 136 504-96-6, U.S. Pat. Nos. 4,233,412, 4,340,534, 4,857,595, DD-A-262 439 (Derwent 89-122 983/17, Chemical Abstracts 111:58 964u), DE-A-4 239 437 (Derwent 94-177 274/22) and U.S. Pat. No. 4,529,760.
Component c) can be prepared analogously to known processes, for example by reaction of a polyamine of the formula IVa with cyanuric chloride in a molar ratio of from 1:2 to 1:4 in the presence of anhydrous lithium carbonate, sodium carbonate or potassium car

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