Synergistic stabilizer mixture

Details Synergistic stabilizer mixture Synergistic stabilizer mixture

1999-03-24

2002-04-30

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...

C524S099000, C524S102000, C524S103000

Reexamination Certificate

active

06380286

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) or e), where
component a) is at least one compound of the formula I
in which
R
1
is hydrogen or methyl,
R
2
is a direct bond or C
1
-C
10
alkylene and
n
1
is a number from 2 to 50;
component b) is at least one compound of the formulae IIa and IIb
in which n
2
and n
2
* are a number from 2 to 50;
component c) is at least one compound of the formula III
in which R
3
and R
7
, independently of one another, are 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 IV
and X
2
is a direct bond or C
1
-C
4
alkylene, R
4
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 by C
1
-C
4
alkyl on the phenyl radical, or C
1
-C
8
acyl,
R
5
, R
6
, R
9
and R
10
, independently of one another, are hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl or phenyl,
R
8
is hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
9
phenylalkyl, phenyl or a group of the formula IV, and
n
3
is a number from 1 to 50;
component d) is at least one compound of the formula V
in which R
11
, R
12
, R
13
, R
14
and R
15
, independently of one another, are a direct bond or C
1
-C
10
alkylene, R
16
is as defined for R
4
, and n
4
is a number from 1 to 50; and
component e) is a product obtainable by reacting a product, obtained by reacting a polyamine of the formula VIa with cyanuric chloride, with a compound of the formula VIb
in which n
5
′, n
5
″ and n
5
′″, independently of one another, are a number from 2 to 12, R
17
is hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl, and R
18
is as defined for R
4
.
n
5
′, n
5
″ and n
5
′″ are preferably from 2 to 4, R
17
is C
1
-C
4
alkyl, and R
18
is preferably hydrogen.
Examples of C
1
-C
10
alkylene are methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, trimethylhexamethylene, octamethylene and decamethylene. R
2
is preferably ethylene, R
11
and R
13
are preferably methylene, R
14
is preferably 2,2-dimethylethylene, and R
15
is preferably 1,1-dimethylethylene.
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
4
, R
6
, R
10
, R
16
and R
18
is C
1
-C
4
alkyl, in particular methyl. One of the preferred meanings of R
5
and R
9
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
8
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.
Examples of C
7
-C
9
phenylalkyl are benzyl and phenylethyl.
C
7
-C
9
phenylalkyl which is substituted by C
1
-C
4
alkyl on the phenyl radical is, for example, methylbenzyl, dimethylbenzyl, trimethylbenzyl or tert-butylbenzyl.
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.
One of the preferred meanings of R
5
and R
9
is phenyl.
X
2
and R
12
are preferably a direct bond.
X
1
, X
3
, R
4
, R
16
and R
18
are preferably hydrogen.
The compounds described as components a) to e) are essentially known (in some cases commercially available) and can be prepared by known processes, for example as described in 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), U.S. Pat. Nos. 4,529,760, 4,477,615 and Chemical Abstracts—CAS No. 136 504-96-6.
Component e) can be prepared analogously to known processes, for example by reaction of a polyamine of the formula VIa 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 carbonate in an organic solvent, such as 1,2-dichloroethane, toluene, xylene, benzene, dioxane or tert-amyl alcohol, at a temperature of from −20° C. to +10° C., preferably from −10° C. to +10° C., in particular from 0° C. to +10° C., for from 2 to 8 hours, followed by reaction of the resultant product with a 2,2,6,6-tetramethyl-4-piperidylamine of the formula VIb. The molar ratio between 2,2,6,6-tetramethyl-4piperidylamine and polyamine of the formula VIa is, for example, from 4:1 to 8:1. The amount of 2,2,6,6-tetramethyl-4-piperidylamine can be added in one portion or in more than one portion at intervals of a few hours.
The polyamine of the formula VIa:cyanuric chloride:2,2,6,6-tetramethyl4-piperidylamine of the formula VIb ratio is preferably from 1:3:5 to 1:3:6.
The following example indicates one way of preparing the preferred component e).
Example: 23.6 g (0.128 mol) of cyanuric chloride, 7.43 g (0.0426 mol) of N,N′-bis[3-aminopropyl]ethylenediamine and 18 g (0.13 mol) of anhydrous potassium carbonate are reacted at 50° C. for 3 hours with stirring in 250 ml of 1,2-dichloroethane. The mixture is warmed at room temperature for a further 4 hours. 27.2 g (0.128 mol) of N-(2,2,6,6-tetramethyl-4-piperidyl)butylamine are added, and the resultant mixture is warmed at 60° C. for 2 hours. A further 18 g (0.13 mol) of anhydrous potassium carbonate are added, and the mixture is warmed at 60° C. for a further 6 hours. The solvent is removed by distillation under a slight vacuum (200 mbar) and replaced by xylene. 18.2 g (0.085 mol) of N-(2,2,6,6-tetramethyl-4-piperidyl)butylamine and 5.2 g (0.13 mol) of ground sodium hydroxide are added, the mixture is refluxed for 2 hours and the water formed during the reaction is removed by azeotropic distillation over a further 12 hours. The mixture is filtered. The solution is washed with water and dried over Na
2
SO
4
. The solvent is evaporated, and the residue is dried at 120-130° C. in vacuo (0.1 mbar). Component e) is obtained as a colourless resin.
In general, component e) can be represented for example by a compound of the formula VI-1, VI-2 or VI-3. It can also be in the form of a mixture of these three compounds.
A preferred meaning of the formula VI-1 is
A preferred meaning of the formula VI-2 is
A preferred meaning of the formula VI-3 is
In the above formulae VI-1 to VI-3, n
5
is preferably 1 to 20.
Component a) is preferably ®TINUVIN 622, component b) is preferably ®HOSTAVIN N 30, component c) is preferably ®UVINUL 5050 H, ®LICHTSCHUTZSTOFF UV 31 or ®LUCHEM B 18, component d) is preferably ®MARK LA 63 or ®MARK LA 68 and component e) is preferably ®UVASORB HA 88.
The compounds of the formulae IIa a

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