Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl...

Details Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl... Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl...

1999-11-04

2001-10-02

Mulcahy, Peter D. (Department: 1713)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C528S423000, C544S191000, C544S204000, C544S209000

Reexamination Certificate

active

06297299

ABSTRACT:

The present invention relates to single specific block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups, to their use as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, particularly synthetic polymers, and to the organic materials thus stabilized. Furthermore, the present invention relates to a mixture with a narrow molecular weight distribution, containing at least three different block oligomers, and to a method of the preparation thereof.
The stabilization of synthetic polymers with derivatives of 2,2,6,6-tetramethylpiperidine has been described for example in U.S. Pat. Nos. 4,086,204, 4,331,586, 4,335,242, 4,234,707, EP-A-357 223 and EP-A-377 324.
The present invention relates in particular to a compound of the formula (I)
in which the polydispersity {overscore (M)}w/{overscore (M)}n is 1;
n is 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; the radicals R
1
are independently of one another hydrogen, C
1
-C
8
alkyl, C
2
-C
8
hydroxyalkyl, —CH
2
CN, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; or C
1
-C
8
acyl;
R
2
is C
2
-C
12
alkylene, C
4
-C
12
alkenylene, C
5
-C
7
cycloalkylene, C
5
-C
7
cycloalkylenedi(C
1
-C
4
alkylene), C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene), phenylenedi(C
1
-C
4
alkylene) or C
4
-C
12
alkylene interrupted by 1,4-piperazinediyl, —O— or >N—X
1
with X
1
being C
1
-C
12
acyl or (C
1
--C
12
alkoxy)carbonyl or having one of the definitions of R
4
given below except hydrogen; or R
2
is a group of the formula (a), (b) or (c);
with m being 2 or 3, X
2
being C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; and the radicals X
3
being independently of one another C
2
-C
12
alkylene; the radicals A are independently of one another —OR
3
, —N(R
4
)(R
5
) or a group of the formula (II);
R
3
, R
4
and R
5
, which are identical or different, are hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; C
3
-C
18
alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; tetrahydrofurfuryl or C
2
-C
4
alkyl which is substituted in the 2, 3 or 4 position by —OH, C
1
-C
8
alkoxy, di(C
1
-C
4
alkyl)amino or a group of the formula (III);
with Y being —O—, —CH
2
—, —CH
2
CH
2
— or >N—CH
3
, or —N(R
4
)(R
5
) is additionally a group of the formula (III);
X is —O— or >N—R
6
;
R
6
is hydrogen, C
1
-C
18
alkyl, C
3
-C
18
alkenyl, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl; C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl; tetrahydrofurfuryl, a group of the formula (IV),
or C
2
-C
4
alkyl which is substituted in the 2, 3 or 4 position by —OH, C
1
-C
8
alkoxy, di(C
1
-C
4
alkyl)amino or a group of the formula (III);
R has one of the definitions given for R
6
; and the radicals B have independently of one another one of the definitions given for A; with the proviso that in the individual recurrent units of the formula (I), each of the radicals B, R, R
1
and R
2
has the same or a different meaning.
In the repeating units of the formula (I), the radical R and the radical
can have a random distribution or a block distribution.
Examples of alkyl containing not more than 18 carbon atoms are methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, t-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, t-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl.
An example of C
2
-C
8
hydroxyalkyl and of C
2
-C
4
alkyl substituted by —OH is 2-hydroxyethyl.
Examples of C
2
-C
4
alkyl substituted by C
1
-C
8
alkoxy, preferably by C
1
-C
4
alkoxy, in particular methoxy or ethoxy, are 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-butoxypropyl, 3-octoxypropyl and 4-methoxybutyl.
Examples of C
2
-C
4
alkyl substituted by di(C
1
-C
4
alkyl)amino, preferably by dimethylamino or diethylamino, are 2-dimethylaminoethyl, 2-diethylaminoethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl, 3-dibutylaminopropyl and 4-diethylaminobutyl.
The group of the formula (III) is preferably
Preferred examples of C
2
-C
4
alkyl substituted by a group of the formula (III) are groups of the formula
The group
is particularly preferred.
Examples of alkoxy containing not more than 8 carbon atoms are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy or octoxy.
Examples of C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C
1
-C
4
alkyl are cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl, cyclodecyl and cyclododecyl. Unsubstituted or substituted cyclohexyl is preferred.
Examples of alkenyl containing not more than 18 carbon atoms are allyl, 2-methylallyl, butenyl, hexenyl, undecenyl and octadecenyl. Alkenyls in which the carbon atom in the 1-position is saturated are preferred, and allyl is particularly preferred.
An example of C
3
-C
6
alkynyl is 2-butynyl.
Examples of phenyl substituted by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy are methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, di-t-butylphenyl, 3,5-di-t-butyl-4-methylphenyl, methoxyphenyl, ethoxyphenyl and butoxyphenyl.
Examples of C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl are benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl and 2-phenylethyl. Benzyl is preferred.
Examples of acyl (aliphatic, cycloaliphatic or aromatic) containing not more than 12 carbon atoms are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl and benzoyl. C
1
-C
8
Alkanoyl and benzoyl are preferred. Acetyl is especially preferred.
Examples of (C
1
-C
12
alkoxy)carbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, hexoxycarbonyl, heptoxycarbonyl, octoxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl and dodecyloxycarbonyl.
Examples of alkylene containing not more than 12 carbon atoms are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, decamethylene and dodecamethylene. R
2
is for example C
2
-C
8
alkylene or C
4
-C
8
alkylene, in particular C
2
-C
6
alkylene, preferably hexamethylene.
An example of C
4
-C
12
alkenylene is 3-hexenylene.
An example of C
5
-C
7
cycloalkylene is cyclohexylene.
Examples of C
4
-C
12
alkylene interrupted by 1,4-piperazinediyl are
Examples of C
4
-C
12
alkylene interrupted by —O—, e.g. 1, 2 or 3 —O—, are 3-oxapentane-1,5-diyl, 4-oxaheptane-1,7-diyl, 3,6-dioxaoctane-1,8-diyl, 4,7-dioxadecane-1,10-diyl, 4,9-dioxadodecane-1,12-diyl, 3,6,9-trioxaundecane-1,11-diyl and 4,7,10-trioxatridecane-1,13-diyl.
Examples of C
4
-C
12
alkylene interrupted by >N—X
1
are —CH
2
CH
2
CH
2
—N(X
1
)—CH
2
CH
2
—N(X
1
)—CH
2
CH
2
CH
2
—, in particular —CH
2
CH
2
CH
2
—N(CH
3
)—CH
2
CH
2
—N(CH
3
)—CH
2
CH
2
CH
2
—.
An example of C
5
-C
7
cycloalkylenedi(C
1
-C
4
alkylene) is cyclohexylenedimethylene.
Examples of C
1
-C
4
alkylenedi(C
5
-C
7
cycloalkylene) are methylenedicyclohexylene and isopropylidenedicyclohexylene.
An example of phenylenedi(C
1
-C
4
alkylene) is phenylenedimethylene.
R is preferably hydrogen, C
1
-C
10
alkyl, cyclohexyl or a group of the formula (IV), in particular a group of the formula (IV).
The radicals R
1
are preferably independently of one another hydrogen, C
1
-C
4
alkyl, allyl, benzyl or acetyl. Hydrogen and methyl are particularly preferred.
The radical B is preferably N-(2,2,6,6-tetramethylpipe

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