Stabilizer mixtures

Details Stabilizer mixtures Stabilizer mixtures

1997-07-31

2003-05-20

Szekely, Peter (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S095000, C524S413000

Reexamination Certificate

active

06566427

ABSTRACT:

STABILIZER MIXTURES
This invention relates to a stabilizer mixture containing A) a certain sterically hindered amine compound, B) a magnesium compound or a zinc compound and C) an UV absorber and/or a pigment, the use of this stabilizer mixture for stabilizing a polyolefin against light-induced degradation and the polyolefin thus stabilized.
Several stabilizer mixtures have already been described in the prior art, for example in U.S. Pat. No. 4,929,652, U.S. Pat. No. 5,037,870, EP-A-290 388, EP-A-468 923 and EP-A-690 094.
Although numerous stabilizer systems already exist, there is still a need to improve the light stability of polyolefin furthermore.
In detail, this invention relates to a stabilizer mixture containing
A) either
(A1) at least one compound of the formula (I)
in which R
1
is hydrogen, C
1
-C
8
alkyl, —O; —OH, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, —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,
R
2
, R
3
, R
5
and R
6
, independently of one another, are hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl or phenyl,
R
4
is hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl, C
7
-C
9
phenylalkyl, phenyl or a group of the formula (II),
wherein R
7
has one of the meanings given for R
1
, and
n
1
is a number from 1 to 50; or
(A2) at least one compound of the formulae (IIIa) and (IIIb)
wherein n
2
and n
2
* are a number from 2 to 50;
B) magnesium oxide, magnesium hydroxide, zinc oxide, zinc hydroxide or an organic salt of zinc or magnesium; and
C) either
(C1) an UV absorber or
(C2) a pigment or
(C3) an UV absorber and a pigment;
with the proviso that, when component A) is at least one compound of the formulae (IIIa) and (IIIb), component B) is magnesium oxide, magnesium hydroxide or an organic salt of zinc or magnesium.
In general, when component A) is at least one compound of the formulae (IIIa) and (IIIb), component B) is preferably an organic salt of zinc or magnesium.
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-dimethyl-butyl, 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
and R
6
is C
1
-C
4
alkyl, in particular methyl. One of the preferred meanings of R
2
and R
5
is C
1
-C
25
alkyl, in particular C
15
-C
25
alkyl, for example C
18
-C
22
alkyl. One of the preferred meanings of R
4
is C
1
-C
25
alkyl, in particular C
10
-C
20
alkyl, for example octadecyl. One of the preferred meanings of R
1
and R
7
is C
1
-C
4
alkyl, in particular methyl.
Examples of C
1
-C
18
alkoxy are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy and octadecyloxy. R
1
and R
7
may be for example C
6
-C
12
alkoxy, in particular heptoxy or octoxy.
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
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 C
3
-C
6
alkenyl are allyl, 2-methallyl, butenyl, pentenyl and hexenyl. Allyl is preferred. The carbon atom in position 1 is preferably saturated. C
7
-C
9
Phenylalkyl which is unsubstituted or substituted by C
1
-C
4
alkyl on the phenyl radical is, for example, benzyl, phenylethyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl or tert-butylbenzyl. Benzyl 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 crotonoyl. Acetyl is preferred.
n
1
is preferably a number from 1 to 25, in particular 1 to 20 or 1 to 10. n
2
and n
2
*, independently of one another, are preferably 2 to 25, in particular 2 to 20 or 2 to 10.
R
1
and R
7
, 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 methyl.
The compounds described as component A) are essentially known (in some cases commercially available) and can be prepared by known processes, for example as described in DD-A-262 439 (Derwent 89-122 983/17, Chemical Abstracts 111:58 964u), WO-A-94/12 544 (Derwent 94-177 274/22) and U.S. Pat. No. 4,340,534.
The compounds of the formulae (IIIa) and (IIIb) can be obtained together as a mixture and also employed as such in the novel stabilizer mixture. The (IIIa):(IIIb) ratio is, for example, from 20:1 to 1:20 or from 1:10 to 10:1.
Component A) is preferably ®UVINUL 5050 H, ®LICHTSCHUTZSTOFF UV 31 or ®HOSTAVIN N 30.
The meanings of the terminal groups which saturate the free valences in the compounds of the formulae (I), (IIIa) and (IIIb) depend on the processes used for their preparation. The terminal groups can also be modified after the preparation of the compounds.
In the compounds of the formula (I), the terminal group bonded to the 2,5-dioxopyrrolidine ring is, for example, hydrogen, and the terminal group bonded to the —C(R
5
)(R
6
)— radical is, for example,
In the compounds of the formula (IIIa), the terminal group bonded to the nitrogen can be, for example, hydrogen and the terminal group bonded to the 2-hydroxypropylene radical can be, for example, a
group.
In the compounds of the formula (IIIb), the terminal group bonded to the dimethylene radical can be, for example, —OH, and the terminal group bonded to the oxygen can be, for example, hydrogen. The terminal groups can also be polyether radicals.
A preferred embodiment of this invention relates to a stabilizer mixture wherein component
A) is at least one compound of the formulae (IIIa) and (IIIb).
Preferred stabilizer mixtures are those wherein
R
2
and R
5
, independently of one another, are C
1
-C
25
alkyl or phenyl,
R
3
and R
6
, independently of one another, are hydrogen or C
1
-C
4
alkyl, and
R
4
is C
1
-C
25
alkyl or a group of the formula (II).
Particularly preferred stabilizer mixtures are those wherein the compound of the formula (I) is
wherein R
1
is hydrogen or methyl, and n
1
is a number from 1 to 25.
The organic salt of zinc or magnesium defined in component B) is preferably a compound of the formula MeL
2
in which Me is zinc or magnesium and L is an anion of an organic acid or of an enol. The organic acid can, for example, be a sulfonic acid, sulfinic acid, phosphonic acid or phosphinic acid, but is preferably a carboxylic acid. The acid can be aliphatic, aromatic, araliphatic or cycloaliphatic; it can be linear or branched; it can be substituted by hydroxyl or alkoxy groups; it can be saturated or unsaturated and it preferably contains 1 to 24 carbon atoms.
Examples of carboxylic acids of this type are formic, acetic, propionic, butyric, isobutyric, caprioic, 2-ethylcaproic, caprylic, capric, lauric, palmitic, stearic, behenic, oleic, lactic, ricinoleic, 2-ethoxypropionic, benzoic, salicylic, 4-butylbenzoic, toluic, 4-dodecylbenzoic, phenylacetic, naphthylacetic, cyclohexanecarboxylic, 4-butylcyclohexanecarboxylic or cyclohexylacetic acid. The carboxylic acid can also be a technical mixture of carboxylic acids, for example technical mixtures of fatty acids or mixtures of alkylated benzoic acids.
Examples of organic acids containing sulfur or phosphorus are methanesulfonic, ethanesulfonic, &agr;,&agr;-dimethylethanesulfonic, n-butanesulfonic, n-dodecanesulfonic, benzenesulfonic, toluenesulfonic, 4-nonylbenzenesulfonic, 4-dodecylbenzenesulfonic or cyclohexanesulfonic acid

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