Sterically hindered amine compounds

Details Sterically hindered amine compounds Sterically hindered amine compounds

1999-12-13

2002-08-27

Raymond, Richard L. (Department: 1611)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S212000, C546S256000

Reexamination Certificate

active

06441166

ABSTRACT:

The present invention relates to products containing 1-(C
1
-C
20
acyl)-2,2,6,6-tetramethyl-4-piperidyl groups as well as 2,2,6,6-tetramethyl-4-piperidyl groups the latter of which may optionally be substituted on the piperidyl nitrogen by C
1
-C
8
alkyl, to the use of these products as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, particularly synthetic polymers, and to the organic materials thus stabilized. 2,2,6,6-tetramethylpiperidine derivatives are, for example, disclosed in EP-A-209,126, EP-A-849,327, DE-A-2,718,458 (U.S. Pat. No. 4,293,468 and U.S. Pat. No. 4,369,275), DE-A-2,755,340 (U.S. Pat. No. 4,238,613), EP-A-52,579 (U.S. Pat. No. 4,419,472), EP-A-107,805, DE-A-3,403,116 (U.S. Pat. No. 4,532,279), U.S. Pat. No. 4,670,488 and U.S. Pat. No. 4,948,889. In detail, the present invention relates to a product containing 5 to 85%, for example 15 to 85%, 15 to 80%, 15 to 75% or 5 to 75%, 15 to 70% or 20 to 70%, 15 to 60%, 20 to 60%, 30 to 60%, 25 to 50%, 40 to 60% or 50% of a group (A-1-a) and/or (A-1-b)
and 15 to 95%, for example 15 to 85%, 20 to 85%, 25 to 85% or 25 to 95%, 30 to 85% or 30 to 80%, 40 to 85%, 40 to 80%, 40 to 70% or 50 to 75%, 40 to 60% or 50% of a group (A-2),
the total sum of the groups (A-1-a), (A-1-b) and (A-2) being 100%.
A product which corresponds to the formula (I) as defined under a), the formula (II) as defined under b), the formula (V) as defined under c), the formula (VI) as defined under d), the formula (VII) as defined under e), a reaction product as defined under f), or which corresponds to the formula (IX) as defined under g), the formula (X) as defined under h), the formula (XI) as defined under i), the formula (XII) as defined under j), the formula (XIII) as defined under k), the formula (XIV) as defined under l), the formula (XVI) as defined under m), the formula (XVII) as defined under n), the formula (XVIII) as defined under o) or the formula (XIX) as defined under p) is preferred.
a) a product mixture of the formula
 in which
the radicals R
1
independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl with 5 to 85% of the total sum of the radicals R
1
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
1
being C
1
-C
20
acyl;
n
1
is 2 or 4,
if n
1
is 2, R
2
is C
1
-C
14
alkylene or bis{(C
1
-C
20
alkyl)oxycarbonyl}C
4
-C
10
alkanetetrayl,
if n
1
is 4, R
2
is C
4
-C
10
alkanetetrayl;
b) a product mixture of the formula
 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),
 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 a group of the formula (IV),
 and the radicals R
9
and R
10
independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl with 5 to 85% of the total sum of the radicals R
9
and R
10
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
9
and R
10
being C
1
-C
20
acyl;
c) a product mixture of the formula
 in which
X
9
, X
10
and X
11
independently of one another are a group of the formula (III) with 5 to 85% of the total sum of the radicals R
9
and R
10
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
9
and R
10
being C
1
-C
20
acyl;
 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 a group of the formula (IV),
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) with 5 to 85% of the radicals R
10
independently of one another being hydrogen or C
1
--C
8
alkyl and the remaining radicals R
10
being C
1
-C
20
acyl;
 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, the radicals R
18
independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl with 5 to 85% of the radicals R
18
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
18
being C
1
-C
20
acyl, and
n
3
is a number from 2 to 50;
f) a product obtainable by reacting a compound, obtained by reaction between a polyamine of the formula (VIIIa) and cyanuric chloride, with a compound of the formula (VIIIb) or a mixture of the compounds (VIIIb) and (VIIIb*) to give an intermediate
 in which
n′
4
, n″
4
and n′″
4
independently of one another are an integer from 2 to 12,
R
19
is hydrogen, C
1
-C
12
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl, and
R
20
is C
1
-C
8
alkyl,
with the proviso that in the mixture of the compounds (VIIIb) and (VIIIb*) at least 15% of the compound (VIIIb) is present; and subsequent acylation of the groups of the formula (A-1-a) being present in the intermediate
 in a proportion to give a product which contains 15 to 95% of the groups of the formula (A-2)
 and 5 to 85% of the groups of the formula (A-1-a) and/or (A-1-b),
 relative to the total sum of the groups (A-1-a), (A-1-b) and (A-2);
 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),
Y
2
is a direct bond or C
1
-C
4
alkylene, the radicals R
22
independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl,
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) with 5 to 85% of the total sum of the radicals R
10
and R
22
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
10
and R
22
being C
1
-C
20
acyl, and
n
5
is a number from 2 to 50;
h) a product mixture of the formula
 in which
R
29
is hydrogen, C
1
-C
12
alkyl or C
1
-C
12
alkoxy, and the radicals R
30
independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl with 5 to 85% of the total sum of the radicals R
30
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
30
being C
1
-C
20
acyl;
 in which
the radicals R
3
, independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl with 5 to 85% of the radicals R
31
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
31
, being C
1
-C
20
acyl, and
n
6
is a number from 2 to 50;
j) a product mixture of the formula
 in which
the radicals R
32
independently of one another are hydrogen, C
1
-C
8
alkyl or C
1
-C
20
acyl with 5 to 85% of the total sum of the radicals R
32
independently of one another being hydrogen or C
1
-C
8
alkyl and the remaining radicals R
32
being C
1
-C
20
acyl,
the radicals R
33
independently o

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