Compositions stabilized by dioxopiperazinyl derivatives

Details Compositions stabilized by dioxopiperazinyl derivatives Compositions stabilized by dioxopiperazinyl derivatives

2002-10-15

2004-07-13

Balasubramanian, Venkataraman (Department: 1624)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S102000, C524S103000, C524S106000, C544S384000

Reexamination Certificate

active

06762226

ABSTRACT:

The invention relates to compositions based on polyoxymethylene, blends of polycarbonate with acrylonitrile-butadiene-styrene terpolymer, or functional acrylate resin and crosslinking agent, which are stabilized by addition of a compound of the class of 3,3,5,5-tetraalkyl-piperazin-2,6-dione, new compounds of this class, the use of the novel compounds as stabilizers for organic material against harmful effects of light, oxygen and/or heat, and organic material stabilized correspondingly.
Structure and numbering of of 3,3,5,5-tetraalkyl-piperazin-2,6-dione is as shown in the formula:
with R being alkyl.
Preparation of some of the above compounds, specific derivatives thereof, and use of these compounds as stabilizers e.g. for polyethylene, polypropylene, nylon or ABS is shown by T. Yoshioka et al., Bull. Chem. Soc. Jap. 45, 1855-1860 (1972); Luston and Vass, Makromol. Chem., Macromol. Symp. (1989), 27; and in the documents U.S. Pat. No. 4,413,096; C.A.99:141068; C.A.96:104191; U.S. Pat. No. 3,969,316; U.S. Pat. No. 3,936,456; U.S. Pat. No. 3,928,357; U.S. Pat. No. 3,928,330; US-A-3920659; U.S. Pat. No. 3,919,234.
It has now been found, that certain compounds of the 3,3,5,5-tetraalkyl-piperazin-2,6-dione class are especially well suitable as stabilizers for polyoxymethylene, blends of polycarbonate with acrylonitrile-butadiene-styrene terpolymer, or coatings based on a functional acrylate resin and a crosslinking agent.
The invention therefore pertains to a composition comprising
(A) a synthetic organic polymer selected from the group consisting of polyoxymethylene, a blend of polycarbonate with acrylonitrile-butadiene-styrene terpolymer, and a coating system based on a functional acrylate resin and a crosslinking agent, and
(B) as stabilizer a compound of the formula I or II
wherein p is from the range 1 to 10;
s is from the range 1 to 8;
when s is 1,
A is C
1
-C
18
alkyl; C
2
-C
18
alkyl which is substituted by NH
2
, hydroxy, halogen and/or OR
10
or interrupted by —O—, —NH— and/or —NR
10
—; or A is C
1
-C
18
alkyl substituted by —COOR
11
or phenyl;
when s is 2,
A is C
2
-C
10
alkylene; C
4
-C
12
alkenylene; C
3
-C
15
alkylene substituted by one or more OH and/or interrupted by one or more oxygen, phenylene, C
1
-C
4
alkylphenylene, —COO—, —CONH—,
when s is 3,
A is C
3
-C
10
alkantriyl; C
3
-C
12
alkantriyl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—; or one of the groups of the formulae (IIIa)-(IIId)
when s is 4,
A is C
4
-C
10
alkantetryl; C
4
-C
12
alkantetryl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—; or one of the groups of the formulae (IVa)-(IVd)
when s is 5,
A is C
5
-C
10
alkanepentayl; C
5
-C
12
alkanepentayl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—; or one of the groups of the formulae (Va)-(Vc)
when s is 6,
A is C
6
-C
10
alkanehexayl; C
6
-C
12
alkanehexayl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—; or one of the groups of the formulae (VIa)-(VIf)
when s is 7,
A is C
7
-C
10
alkaneheptayl; C
7
-C
12
alkaneheptayl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—; or one of the groups of the formulae (VIIa)-(VIId)
when s is 8,
A is C
8
-C
10
alkaneoctayl; C
8
-C
12
alkaneoctayl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—; or one of the groups of the formulae (VIIIa)-(VIIIb)
the index i is zero or 1;
R
1
, R
2
, R
3
and R
4
, independently of each other, are C
1
-C
4
alkyl, or R
1
and R
2
or R
3
and R
4
, together with the carbon atom to which they are bound, form a cyclopentyl or cyclohexyl ring;
R
5
is hydrogen; C
1
-C
18
alkyl; oxyl; OH; CH
2
CN; C
1
-C
18
alkoxy; C
5
-C
12
cycloalkoxy; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
7
-C
12
phenylalkyl; C
7
-C
15
phenylalkyl, which is substituted on the phenyl ring by 1, 2 or 3 radicals selected from C
1
-C
4
alkyl and C
1
-C
4
alkoxy; C
1
-C
15
phenylalkoxy; C
1
-C
15
phenylalkoxy, which is substituted on the phenyl ring by 1, 2 or 3 radicals selected from C
1
-C
4
alkyl and C
1
-C
4
alkoxy; or R
5
is C
1
-C
8
alkanoyl; C
3
-C
5
alkenoyl; C
1
-C
18
alkanoyloxy; glycidyl; or a group —CH
2
CH(OH)-G, in which G is hydrogen, methyl or phenyl;
R
8
and R
9
, and R
28
, R
29
, R
30
, R
31
, R
32
and R
33
, independently of each other, are C
1
-C
4
alkylene;
R
10
is C
1
-C
8
alkyl, C
1
-C
8
alkanoyl, C
5
-C
12
cycloalkyl, C
7
-C
15
phenylalkyl which is unsubstituted or substituted on the phenyl ring by a radical selected from C
1
-C
4
alkyl and C
1
-C
4
alkoxy; or R
10
is C
1
-C
8
alkyl or C
1
-C
8
alkanoyl substituted by OH, C
1
-C
12
alkoxy and/or a residue benzophenonyl or benzophenonyloxy, wherein one or both phenyl rings of the benzophenone moiety are unsubstituted or substituted by OH, halogen, C
1
-C
4
alkyl and/or C
1
-C
18
alkoxy;
R
11
is C
1
-C
18
alkyl; C
2
-C
18
alkyl which is substituted by NH
2
, NHR
10
, N(R
10
)
2
, nitro, hydroxy and/or C
1
-C
18
alkoxy; C
3
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
5
-C
12
cycloalkyl which is substituted by C
1
-C
4
alkyl and/or interrupted by —O—;
R
12
, R
13
and R
14
, independently of each other, are C
2
-C
10
alkylene; C
3
-C
12
alkylene substituted by OH and/or interrupted by oxygen, phenylene, C
1
-C
4
alkylphenylene, —NH— or —NR
10
—; C
4
-C
12
alkenylene;
R
15
and R′
15
, independently of each other, are is C
2
-C
10
alkylene; C
3
-C
12
alkylene substituted by OH and/or interrupted by oxygen, phenylene, C
1
-C
4
alkylphenylene, —NH— or —NR
10
—;
R
16
is C
3
-C
10
alkantriyl; C
3
-C
12
alkantriyl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—;
R
17
is C
4
-C
10
alkantetryl; C
4
-C
12
alkantetryl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—;
R
18
is C
5
-C
10
alkanepentayl; C
5
-C
12
alkanepentayl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—;
R
19
is C
6
-C
10
alkanehexayl; C
6
-C
12
alkanehexayl substituted by OH and/or interrupted by oxygen, —NH— or —NR
10
—;
X is —O—, —NH— or —N(R
10
)—;
X
1
, X
2
, X
3
, X
4
, X
5
, X
6
, X
7
and X
8
, independently of each other, are —O— or —NH—;
Y is —O— or a residue of the formula
Z stands for halogen, NH
2
, NHR
10
, N(R
10
)
2
or C
1
-C
4
alkoxy;
Z
1
has one of the meanings given for Z or is —X—R′
15
—XH and
Z
2
is H or a residue of the formula
Where one compound carries more than one group denoted with the same symbol, these groups may be the same or different within their defined meanings.
Alkylene, cycloalkylene or alkenylene residues may be bonded on different carbon atoms or on the same carbon atom thus embracing alkylidene, cycloalkylidene and alkenylidene, respectively.
All residues, where appropriate, may be straight chain or branched unless otherwise indicated. Hetero atoms are non-carbon atoms, for instance N, O, S or P atoms. Alkyl or alkylene interrupted by hetero groups such as oxygen or cycloalkylene may be interrupted by one or more of these groups as long as no linkages of the type O—O, O—N etc. occur.
The index s is the valency of A; for example, A as alkyl is a monovalent, A as alkylene a divalent, A as alkanetriyl a trivalent, A as alkanetetryl a tetravalent, A as alkanepentayl a pentavalent, A as alkanehexayl a hexavalent, A as alkaneheptayl a heptavalent, and A as alkaneoctayl an octovalent saturated hydrocarbon residue. A residue which is interrupted is interrupted in a carbon—carbon single bond. A residue which is interrupted and/or substituted may be a residue interrupted in one or more carbon—carbon single bonds by one or more divalent interrupting groups, a residue substituted by one or more monovalent substituents, or a residue which is both interrupted in one or more carbon—carbon single bonds by one or more divalent interrupting groups and substituted by one or more monovalent substituents.
Thus, examples for A as C
3
-C
15
alkylene substituted by one or more OH and/or interrupted by oxygen, phenylene, C
1
-C
4
alkylphenylene, —COO—, —CONH—, —NH— or —NR
10
— include groups of the formulae CH
2
CH(OH)CH
2
, CH
2
—C(CH
2
OH)
2
—CH
2
, (CH
2
)
2
—N(CHO)—(CH
2
)
2
, (CH
2
)
2
—N H

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