Stabilizer mixtures

Details Stabilizer mixtures Stabilizer mixtures

1997-08-14

2003-04-08

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...

C524S089000, C524S102000, C524S103000, C524S399000, C524S400000

Reexamination Certificate

active

06545071

ABSTRACT:

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. Nos. 4,929,652, 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.
This invention relates to a stabilizer mixture containing
A) either
(A1) at least one compound of the formula (I)
 wherein the radicals R
1
, independently of one another, are 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; or
(A2) at least one compound of the formula (II)
 wherein
the radicals R
2
, independently of one another, have one of the definitions given for R
1
, and
R
3
is C
2
-C
22
alkylene, C
5
-C
7
cycloalkylene, C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene), phenylene or phenylenedi(C
1
-C
4
alkylene); or
(A3) at least one compound of the formula (III)
 wherein
the radicals R
4
, independently of one another, have one of the definitions given for R
1
,
and R
5
is hydrogen, C
1
-C
12
alkyl or C
1
-C
12
alkoxy; or
(A4) at least one compound of the formula (IV)
 wherein the radicals R
6
, independently of one another, have one of the definitions given for R
1
,
the radicals R
7
, independently of one another, are hydrogen or C
1
-C
1
alkyl, and
R
8
and R
9
, independently of one another, are C
1
-C
12
alkyl; or
(A5) at least one compound of the formula (V)
 wherein
the radicals R
10
, independently of one another, have one of the definitions given for R
1
, and
R
11
is C
2
-C
22
alkylene; or
(A6) at least one compound of the formula (VI)
 wherein R
12
is a group of the formula (VII)
 in which
R
13
is C
1
-C
12
alkyl or C
5
-C
12
cycloalkyl,
R
14
is C
2
-C
12
alkylene, and
R
15
has one of the meanings given for R
1
; or
(A7) at least one compound of the formula (VIII)
 wherein
R
16
is C
1
-C
24
alkyl, and
R
17
has one of the definitions given for R
1
; and
B) magnesium oxide, magnesium hydroxide, zinc oxide, zinc hydroxide or an organic salt of zinc or magnesium, or a hydrotalcite; and
C) either
(C1) an UV absorber or
(C2) a pigment or
(C3) an UV absorber and a pigment.
Component B) is preferably magnesium oxide, magnesium hydroxide, zinc oxide, zinc hydroxide or an organic salt of zinc or magnesium.
When component A) is at least one compound of the formula I or IV, component B) is preferably magnesium oxide, magnesium hydroxide or an organic salt of zinc or magnesium, in particular an organic salt of zinc or magnesium.
Examples of alkyl having up to 24 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 and docosyl.
A preferred embodiment of R
1
, R
2
, R
4
, R
6
, R
10
, R
15
and R
17
is C
1
-C
4
alkyl, in particular methyl.
One of the preferred meanings of R
5
, R
7
, R
8
, R
9
and R
13
is C
1
-C
8
alkyl, in particular C
1
-C
4
alkyl, for example methyl.
R
16
is preferably C
1
-C
14
alkyl, in particular C
8
-C
14
alkyl, for example docecyl.
Examples of C
1
-C
12
alkoxy are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy and dodecyloxy.
One of the preferred meanings of R
5
is C
1
-C
8
alkoxy, in particular C
1
-C
4
alkoxy, for example methoxy.
Examples of C
5
-C
12
cycloalkyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclododecyl. C
5
-C
7
cycloalkyl, in particular cyclohexyl, 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, acrylyl and crotonyl. Acetyl is preferred.
Examples of alkylene having up to 22 carbon atoms are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, trimethylhexamethylene, octamethylene, decamethylene, undecamethylene, tetradecamethylene, hexadecamethylene and octadecamethylene. C
2
-C
10
alkylene is preferred, in particular C
2
-C
6
alkylene, for example dimethylene and hexamethylene.
R
3
is preferably hexamethylene and R
11
and R
14
are preferably dimethylene.
An example of C
5
-C
7
cycloalkylene is cyclohexylene.
An example of C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene) is
An example of phenylenedi(C
1
-C
4
alkylene) is phenylenedimethylene.
The radical R
5
in the formula (III) is preferably in the para-position.
R
1
, R
2
, R
4
, R
6
, R
10
, R
15
and R
17
, independently of one another, are preferably hydrogen, C
1
-C
4
alkyl, 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 U.S. Pat. Nos. 4,769,457, 4,976,889, GB-A-2 269 819, EP-A-172 413, U.S. Pat. Nos. 4,190,571, 5,071,981 and 4,356,307.
Component A) is preferably ®UVINUL 4049, ®UVINUL 4050 H, ®SANDUVOR PR-31, ®SUMISORB TM 61, ®GOODRITE UV 3034, ®GOODRITE UV 3150, ®GOODRITE UV 3159, ®CYASORB UV 3581 or ®SANDUVOR 3056.
A preferred embodiment of this invention relates to a stabilizer mixture wherein component A) is at least one compound of the formula (II), (III), (V), (VI) or (VIII).
Preferred stabilizer mixtures are those wherein
R
3
is C
2
-C
10
alkylene, cyclohexylene, (C
1
-C
4
alkylene)dicyclohexylene, phenylene or phenylenedi(C
1
-C
4
alkylene),
R
5
is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy,
the radicals R
7
, independently of one another, are hydrogen or C
1
-C
4
alkyl,
R
8
and R
9
, independently of one another, are C
1
-C
4
alkyl,
R
11
is C
2
-C
10
alkylene,
R
13
is C
1
-C
4
alkyl or cyclohexyl,
R
14
is C
2
-C
10
alkylene and
R
16
is C
1
-C
1 4
alkyl.
Particularly preferred stabilizer mixtures are those wherein component A) is a compound of the formula
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 a

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