Compositions – Preservative agents – Anti-oxidants or chemical change inhibitants
Reexamination Certificate
1998-06-24
2002-04-09
Wu, Shean C. (Department: 1756)
Compositions
Preservative agents
Anti-oxidants or chemical change inhibitants
C252S403000, C252S405000, C524S099000, C524S100000, C524S101000, C524S102000
Reexamination Certificate
active
06368520
ABSTRACT:
The present invention relates to a stabilizer system comprising two specific polyalkylpiperidine derivatives, some of which are novel, 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.
Polyalkylpiperidine derivatives are described for example in WO-A-94/112 544, U.S. Pat. No. 4,110,334 and U.S. Pat. No. 5,204,473.
U.S. Pat. No. 4,692,486, U.S. Pat. No. 4,863,981, U.S. Pat. No. 4,957,953, WO-A-92/12 201, WO-A-94/22 946, EP-A-449 685, EP-A-632 092, GB-A-2 267 499 and Research Disclosure 34 549 (January 1993) describe some stabilizer mixtures which comprise two polyalkylpiperidine derivatives.
The present invention relates to a stabilizer mixture comprising a component I-a), I-b), I-c), I-d), I-e), I-f), I-g), I-h), I-i), I-j), I-k) or I-l) and a component II-a), II-b), II-c), II-d), II-e), II-f), II-g), II-h), II-i), II-j), II-k), II-l) or II-m), where
component I-a) is at least one compound of the formula I-1
in which
R
1
is hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl or C
1
-C
4
alkyl-substituted
C
5
-C
12
cycloalkyl,
n
1
is 1, 2 or 4,
if n
1
is 1, R
2
is C
1
-C
25
alkyl,
if n
1
is 2, R
2
is C
1
-C
14
alkylene and
if n
1
is 4, R
2
is C
4
-C
10
alkanetetrayl,
with the provisos that,
(1) in a stabilizer mixture comprising component I-a) and component II-b) or I-m), if
n
1
=2, R
1
is other than C
1
-C
18
alkyl and
(2) in a stabilizer mixture comprising component I-a) and component II-d), if n
1
=2 and
R
1
=C
1
-C
18
alkyl, the group —N(A
14
)A
15
is a 5- to 10-membered heterocyclic ring;
component I-b) is at least one compound of the formula II-1
in which
R
3
and R
7
independently of one another are hydrogen or C
1
-C
12
alkyl,
R
4
, R
5
and R
6
independently of one another are C
2
-C
10
alkylene and
X
1
, X
2
, X
3
, X
4
, X
5
, X
6
, X
7
and X
8
independently of one another are a group of the formula III-1
in which
R
8
is hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, C
1
-C
4
alkyl-substituted C
5
-C
12
cycloalkyl, phenyl, —OH— and/or C
1
-C
10
alkyl-substituted phenyl, 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 is a group of the formula IV-1
and R
9
and R
10
independently of one another are as defined for R
1
;
component I-c) is at least one compound of the formula V-1
in which
X
9
, X
10
and X
11
independently of one another are a group of the formula III-1;
component I-d) is at least one compound of the formula VI-1
in which
R
11
, R
13
, R
14
and R
15
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, —OH— and/or C
1
-C
10
alkyl-substituted phenyl, 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 are a group of the formula IV-1,
R
12
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
11
, R
12
and R
13
, together with the nitrogen atoms to which they are attached, form a 5- to 10-membered heterocyclic ring, or
R
14
and R
15
, together with the nitrogen atom to which they are attached, form a 5- to 10-membered heterocyclic ring,
n
2
is a number from 2 to 50 and
at least one of the radicals R
11
, R
13
, R
14
and R
15
is a group of the formula IV-1;
component I-e) is at least one compound of the formula VII-1
in which
R
16
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
17
is C
3
-C
10
alkylene,
R
18
is as defined for R
1
and
n
3
is a number from 1 to 50;
component I-f) is a product obtainable by
a) reacting a product, obtained by reaction of a polyamine of the formula VIII-1-a with cyanuric chloride, with a compound of the formula VIII-1-b
in which
n
4
′, n
4
″ and n
4
′″ independently of one another are a number from 2 to 12 and
R
19
is hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl, and
b) further reacting the 2,2,6,6-tetramethylpiperid-4-yl groups present in the molecule to give groups of the formula VIII-1-c
in which R
20
is as defined for R
1
;
component I-g) is at least one compound of the formula IX-1
in which
R
21
and R
26
independently of one another are a direct bond or a group —N(Y
1
)—CO—Y
2
—CO—N(Y
3
)—,
Y
1
and Y
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-1,
Y
2
is a direct bond or C
1
-C
4
alkylene,
R
22
is as defined for R
1
,
R
23
, R
24
, R
27
and R
28
independently of one another are hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl or phenyl,
R
25
is hydrogen, C
1
-C
30
alkyl, C
5
-C
12
cycloalkyl, phenyl, C
7
-C
9
phenylalkyl or a group of the formula IV-1 and
n
5
is a number from 1 to 50;
component I-h) is at least one compound of the formula X-1
in which
R
29
is C
1
-C
24
alkyl and
R
30
is as defined for R
1
;
component I-i) is at least one compound of the formula XI-1
in which
R
31
is as defined for R
1
and
n
6
is a number from 2 to 50;
component I-j) is at least one compound of the formula XII-1
in which
R
32
and R
33
together form C
2
-C
14
alkylene,
R
34
is hydrogen or a group —Z
1
—COO—Z
2
,
Z
1
is C
2
-C
14
alkylene and
Z
2
is C
1
-C
24
alkyl and
R
35
is as defined for R
1
;
component I-k) is at least one compound of the formula XIII-1
in which R
36
, R
37
, R
38
, R
39
and R
40
independently of one another are a direct bond or C
1
-C
10
alkylene,
R
41
is as defined for R
1
and
n
7
is a number from 1 to 50;
component I-l) is at least one compound of the formula XIV-1
in which
X
12
, X
13
and X
14
independently of one another are a group of the formula XV-1
in which A is a group of the formula III-1;
component II-a) is at least one compound of the formula I-2
in which
A
1
is hydrogen, C
1
-C
8
alkyl, O, —CH
2
CN, C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl or C
7
-C
9
phenylalkyl which is substituted on the phenyl radical by C
1
-C
4
alkyl,
b
1
is 1, 2 or 4,
if b
1
is 1, A
2
is C
1
-C
25
alkyl,
if b
1
is 2, A
2
is C
1
-C
14
alkylene and
if b
1
is 4, A
2
is C
4
-C
10
alkanetetrayl;
component II-b) is at least one compound of the formula II-2
in which
A
3
and A
7
independently of one another are hydrogen or C
1
-C
12
alkyl,
A
4
, A
5
and A
6
independently of one another are C
2
-C
10
alkylene and
T
1
, T
2
, T
3
, T
4
, T
5
, T
6
, T
7
and T
8
independently of one another are a group of the formula III-2
in which A
8
is hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, C
1
-C
4
alkyl-substituted C
5
-C
12
cycloalkyl, phenyl, —OH— and/or C
1
-C
10
alkyl-substituted phenyl, 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 is a group of the formula IV-2
and A
9
and A
10
independently of one another are as defined for A
1
;
component II-c) is at least one compound of the formula V-2
in which
T
9
, T
10
and T
11
independently of one another are a group of the formula III-2;
component II-d) is at least one compound of the formula VI-2
in which
A
11
, A
13
, A
14
and A
15
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, —OH— and/or C
1
-C
10
alkyl-substituted phenyl, 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 are a group of the formula IV-2,
A
12
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 A
11
, A
12
and A
13
, together with the nitrogen atoms to which they are attached, form a 5- to 10-membered heterocyclic ring, or
A
14
and A
1
Ciba Specialty Chemicals Corporation
Crichton David R.
Hall Luther A. R.
Wu Shean C.
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