Block oligomers containing...

Details Block oligomers containing... Block oligomers containing...

1999-11-18

2002-06-11

Sanders, Kriellion A. (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S100000, C252S403000, C544S198000, C544S209000, C544S212000

Reexamination Certificate

active

06403680

ABSTRACT:

The present invention relates to specific block oligomers containing 1-hydrocarbyloxy-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. The invention further relates to intermediate products.
The stabilization of synthetic polymers with derivatives of 2,2,6,6-tetramethylpiperidine has been described for example in U.S. Pat. No. 4,086,204, U.S. Pat. No. 4,331,586, U.S. Pat. No. 4,335,242, U.S. Pat. No. 4,234,707, U.S. Pat. No. 4,459,395, U.S. Pat. No. 4,492,791, U.S. Pat. No. 5,204,473, EP-A-53 775, EP-A-357 223, EP-A-377 324, EP-A-462 069, EP-A-782 994 and GB-A-2 301 106.
The present invention relates in particular to a product obtainable by
1) reacting a compound of the formula (&agr;)
 with a compound of the formula (&bgr;)
 in a stoichiometric ratio to obtain a compound of the formula (&ggr;);
2) reacting the compound of the formula (&bgr;) with the compound of the formula (&ggr;) in a molar ratio of 0.4:1 to 0.75:1, preferably 0.5:1 to 0.75:1, in particular 0.5:1;
3) reacting the end groups of the formula (&dgr;)
 being present in the product of the reaction 2) with a compound of the formula (&egr;)
A—H  (&egr;)
 in a molar ratio of 2 (end group):1.7 to 2:3, preferably 2:2 to 2:2.6, in particular 2:2 to 2:2.4;
 the reactions 1) to 3) being carried out in an organic solvent in the presence of an inorganic base; and
4 transferring the groups of the formula (G-I)
 being present in the product of the reaction 3) to groups of the formula (G-II);
 said transfer being carried out by reacting the product of the reaction 3) with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst;
R
1
is a hydrocarbyl radical or —O—R, is oxyl;
R
2
is C
2
-C
12
alkylene, C
4
-C
12
alkenylene, C
1
-C
7
cycloalkylene, C
1
-C
7
cycloalkylenedi(C
1
-C
4
alkylene), C
5
-C
4
alkylenedi-(C
5
-C
7
cycloalkylene), phenylenedi(C
5
-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; or R
2
is a group of the formula (I-a), (I-b) or (I-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;
A is —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 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
;
and R
3
is additionally hydrogen or —N(R
4
)(R
5
) is additionally a group of the formula (III);
X is —O— or >N—R
6
;
R
6
is C
1
-C
18
alkyl, C
3
-C
12
alkenyl, C
5
-C
18
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 (G-I), 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 meanings given for R
6
; and
B has one of the meanings given for A.
The transfer of the groups of the formula (G-I) to groups of the formula (G-II) may be carried out, for example, analogously to the method described in U.S. Pat. No. 4,921,962 which is incorporated by reference herein.
The meaning of R
1
depends on the hydrocarbon solvent used in the reaction 4). R
1
is preferably a hydrocarbyl radical having 5 to 18 carbon atoms.
R
1
is in particular C
5
-C
18
alkyl, C
5
-C
18
alkenyl, C
5
-C
18
alkynyl, C
5
-C
12
cycloalkyl unsubstituted or substituted by C
1
-C
4
alkyl; C
5
-C
12
cycloalkenyl unsubstituted or substituted by C
1
-C
4
alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms or C
7
-C
9
phenylalkyl unsubstituted or substituted on the phenyl by C
1
-C
4
alkyl; and
the hydrocarbon solvent in the reaction 4) is accordingly, dependent on R
1
, C
5
-C
18
alkane, C
5
-C
18
alkene, C
5
-C
18
alkynyl, C
5
-C
12
cycloalkane unsubstituted or substituted by C
1
-C
4
alkyl; C
5
-C
12
cycloalkene unsubstituted or substituted by C
1
-C
4
alkyl; a bicyclic or tricyclic hydrocarbon having 6 to 10 carbon atoms or C
7
-C
9
phenylalkane unsubstituted or substituted on the phenyl by C
1
-C
4
alkyl.
According to a further preferred embodiment R
1
is heptyl, octyl, cyclohexyl, methylcyclohexyl, cyclooctyl, cyclohexenyl, &agr;-methylbenzyl or 1,2,3,4-tetrahydronaphthenyl, and
the hydrocarbon solvent in the reaction 4) is, dependent on R
1
, heptane, octane, cyclohexane, methylcyclohexane, cyclooctane, cyclohexene, ethylbenzene or tetralin.
According to a particularly preferred embodiment R
1
is octyl or cyclohexyl, and the hydrocarbon solvent in the reaction 4) is, dependent on R
1
, octane or cyclohexane.
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. R
1
is preferably C
6
-C
12
alkyl, in particular heptyl or octyl. R
4
, R
5
and R
6
are preferably C
1
-C
8
alkyl, in particular C
1
-C
4
alkyl.
An example 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, 3octoxypropyl 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 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.
A preferred example of a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms is 1,2,3,4-tetrahydronaphthenyl.
A preferred example of C
5
-C
12
cycloalkenyl unsubstituted or substituted by C
1
-C
4
alkyl is cyclohexenyl.
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 alkynyl is pentynyl or octynyl.
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

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