Piperazinone derivatives

Details Piperazinone derivatives Piperazinone derivatives

2001-05-22

2003-07-22

Baxter, Janet (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Imaging affecting physical property of radiation sensitive...

Radiation sensitive composition or product or process of making

C430S271100, C430S273100, C430S281100, C430S286100, C430S287100, C430S372000, C430S512000, C430S551000, C430S905000, C430S906000, C430S907000, C544S357000, C544S379000, C544S383000, C544S198000, C544S209000, C544S212000, C528S423000, C524S100000, C524S102000, C252S401000, C252S403000, C252S405000

Reexamination Certificate

active

06596461

ABSTRACT:

This invention relates to piperazinone derivatives, to an organic material susceptible to light, heat or oxidation, containing a piperazinone derivative and to a method for stabilizing such an organic material. This invention further relates to intermediate products.
Several piperazinone derivatives and their use as stabilizers are described in U.S. Pat. Nos. 4,629,752 and 4,480,092.
The present invention relates in particular to a compound of the formula (I)
wherein
at least one group of the formula (II)
is present in the repeating unit of the formula (I);
n is a number from 1 to 100;
G
1
, G
2
, G
3
and G
4
are independently of one another C
1
-C
18
alkyl or C
5
-C
12
cycloalkyl or the radicals G
1
and G
2
and the radicals G
3
and G
4
form independently of one another, together with the carbon atom they are attached to, C
5
-C
12
cycloalkyl;
R
1
is hydrogen, C
1
-C
18
alkyl, oxyl, —OH, —CH
2
CN, C
3
-C
6
alkenyl, C
3
-C
8
alkynyl, C
7
-C
12
phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
1
-C
8
acyl, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
7
-C
12
phenylalkoxy unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
1
-C
18
alkanoyloxy, (C
1
-C
18
alkoxy)carbonyl, glycidyl or a group —CH
2
CH(OH)(G) with G being hydrogen, methyl or phenyl;
R
2
is C
2
-C
14
alkylene or a group —CR
2
′(R
2
″)— with R
2
′ and R
2
″ being independently of one another hydrogen, C
1
-C
18
alkyl or C
5
-C
12
cycloalkyl;
R
3
′ and R
3
″ are independently of one another hydrogen, C
1
-C
18
alkyl, C
2
-C
18
alkyl interrupted by oxygen; or C
5
-C
12
cycloalkyl;
R
4
is C
2
-C
14
alkylene, C
4
-C
14
alkylene interrupted by oxygen or sulphur; 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) or phenylenedi(C
1
-C
4
alkylene);
R
5
′ and R
5
″ are independently of one another 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
12
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 (II) 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 E being a direct bond, —O—, —CH
2
—, —CH
2
CH
2
— or >N—CH
3
;
X is —OR
6
, —SR
6
, —N(R
7
)(R
8
) or a group of the formula (IV);
R
6
R
7
and R
8
are independently of one another 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; 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
12
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 C
1
-C
8
alkoxy, di(C
1
-C
4
alkyl)amino or a group of the formula (III);
or —N(R
7
)(R
8
) is additionally a group of the formula (III);
T is —O— or >N—R
9
; and
R
9
is hydrogen, C
1
-C
18
alkyl, C
2
-C
18
hydroxyalkyl, 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
12
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 (II), or C
2
-C
4
alkyl which is substituted in the 2, 3 or 4 position by C
1
-C
8
alkoxy, di(C
1
-C
4
alkyl)amino or a group of the formula (III);
the radicals R
1
, the radicals R
2
, the radicals R
3
′, the radicals R
3
″, the radicals G
1
, the radicals G
2
, the radicals G
3
or the radicals G
4
, independently of one another, have the same or a different meaning; and
in the individual recurrent units of the formula (I), each of the radicals X, R
4
, R
5
′ and R
5
″ has the same or a different meaning;
with the proviso that one of the radicals R
5
′ and R
5
″ is different from hydrogen, when X is a group of the formula (IV) with T being >N—R
9
.
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.
G
1
, G
2
, G
3
and G
4
are preferably C
1
-C
4
alkyl, in particular methyl.
One of the preferred meanings of R
1
is C
1
-C
4
alkyl, in particular methyl.
One of the preferred meanings of R
3
′ and R
3
″ are C
1
-C
8
alkyl, in particular C
1
-C
4
alkyl, for example methyl.
One of the preferred meanings of R
7
, R
8
and R
9
is C
1
-C
8
alkyl.
An example of C
2
-C
18
hydroxyalkyl and of C
2
-C
4
alkyl substituted by —OH is 2-hydroxyethyl.
Examples of C
2
-C
18
alkyl interrupted by oxygen and 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 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
8
alkynyl is 2-butynyl.
Examples of alkoxy containing not more than 18 carbon atoms are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy and octadecyloxy. C
6
-C
12
Alkoxy, in particular heptoxy and octoxy, is one of the preferred meanings of R
1
.
Examples of acyl (aliphatic, cycloaliphatic or aromatic) containing not more than 8 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
18
alkanoyloxy are formyloxy, acetyloxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, heptanoyloxy and octanoyloxy.
Examples of (C
1
-C
18
alkoxy)carbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl and octyloxycarbonyl.
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 C
5
-C
8
cycloalkyl, in particular cyclohexyl, is preferred.
Examples of C
5
-C
12
cycloalkoxy are cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclodecyloxy, cyclododecyloxy and methylcyclohexoxy. C
5
-C
8
Cycloalkoxy, in particular cyclopentoxy and cyclohexoxy, is preferred.
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
12
phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C
4
alkyl or C
1
-C
4
alkoxy are benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl, 2-phenylethyl and methoxybenzyl. C
7
-C
9
phenylalkyl, in particular benzyl, is preferred.
Example of C
7
-C
12
phenylalkoxy unsubstituted or substituted on the phenyl by 1, 2 or 3 C
1
-C

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