Oxopiperazinyl derivatives and light stabilized compositions

Details Oxopiperazinyl derivatives and light stabilized compositions Oxopiperazinyl derivatives and light stabilized compositions

2001-05-15

2003-11-04

Ford, John M. (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S384000, C544S049000, C524S100000, C524S102000, C524S103000, C524S131000

Reexamination Certificate

active

06642383

ABSTRACT:

The invention relates to new compounds of the class 3,3,5,5-tetramethyl-2-oxo-1,4-piperazine, polymers thereof, the use of the novel compounds or polymers as stabilizers for organic material against harmful effects of light, oxygen and/or heat, and organic material stabilized correspondingly.
Structure and numbering of 3,3,5,5-tetramethyl-2-oxo-1,4-piperazine is as shown in the formula:
It has now been found, that certain compounds containing one or more moieties of the type 3,3,5,5-tetramethyl-2-oxo-1,4-piperazine-1-yl bonded via an oxygen atom are especially well suitable as stabilizers for organic materials.
The invention therefore relates to a compound of the formula (I)
wherein
p is zero or 1;
q and r, independently of each other, are an integer from 1 to 6; and
s is a number ranging from 1 to 8;
X is —O— or, when p is 1, X is also a group
R
w
, R
x
, R
y
and R
z
are, independently of each other, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl or C
1
-C
5
hydroxyalkyl, especially methyl;
R
1
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
7
-C
15
phenylalkoxy; C
7
-C15phenylalkoxy, 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
1
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
2
and R
6
, independently of each other, are hydrogen, C
1
-C
8
alkyl, C
5
-C
12
cycloalkyl or C
1
-C
4
hydroxyalkyl;
R
3
, R
4
, R
5
, R
7
, R
8
, R
9
, independently of each other, are hydrogen, C
1
-C
8
alkyl or C
5
-C
12
cycloalkyl;
when s is 1,
W 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 OR′
13
; or W is C
5
-C
12
cycloalkyl; C
5
-C
12
cycloalkyl which is substituted by OH, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
3
-C
6
alkenyl; C
3
-C
12
epoxyalkyl; 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 W is one of the groups of the formulae (IIa)-(IIe)
or, when R
1
is a group —CH
2
CH(OH)—G, W may also be hydrogen;
R
10
is hydrogen, C
1
-C
8
alkyl, 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;
R
11
is hydrogen; C
1
-C
17
alkyl; C
1
-C
12
alkyl 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; or R
11
is C
5
-C
12
cycloalkyl which is unsubstituted or substituted by C
1
-C
4
alkyl; C
2
-C
17
alkenyl; phenyl; phenyl substituted by NH
2
, NHR
10
, N(R
10
)
2
, or C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
7
-C
15
phenylalkyl; C
8
-C
15
phenylalkenyl; or C
7
-C
15
phenylalkyl which is substituted on the phenyl ring by C
1
-C
4
alkyl and/or C
1
-C
4
alkoxy;
R
12
is a direct bond or C
1
-C
12
alkylene; phenylene; cyclohexylene;
R
13
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 OR
13
; 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—; and when W is a group (IId) and when W is a group (IIb) while R
12
is not a direct bond, R
13
can be also hydrogen, or one equivalent of a cation of groups Ia or IIa of the periodic system, especially sodium or potassium;
R′
13
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 OR
13
; 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
14
is C
1
-C
18
alkyl; C
2
-C
18
alkyl which is substituted by NH
2
, NHR
10
, N(R
10
)
2
, hydroxy and/or OR
13
; C
5
-C
12
cycloalkyl which is unsubstituted or substituted by C
1
-C
4
alkyl and/or interrupted by —O—; or 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;
R
15
is a direct bond; C
1
-C
20
alkylene; C
2
-C
10
alkenylene; C
2
-C
8
alkenylene substituted by C
6
-C
12
aryl or C
6
-C
12
aryl which is substituted by C
1
-C
8
alkyl, C
1
-C
8
alkoxy, di(C
1
-C
4
-alkyl)amino, nitro, thienyl, phenoxyphenyl, phenylthiophenyl, benzo[b]thiophen-2-yl, benzofuran-2-yl, 9H-fluorenyl, biphenylyl, 10H-phenothiazinyl; C
2
-C
4
oxaalkylene; C
5
-C
7
cycloalkylene; C
5
-C
7
cycloalkenylene or phenylene;
when s is 2
W is C
2
-C
12
alkylene; C
4
-C
12
alkylene substituted by OH and/or interrupted by oxygen or sulfur or —NR
10
—; C
4
-C
12
alkenylene; C
6
-C
12
alkenylene substituted by OH and/or interrupted by O; C
5
-C
7
cycloalkylene; C
5
-C
7
cycloalkylene-di(C
1
-C
4
alkylene); C
1
-C
4
alkylene-di(C
5
-C
7
cycloalkylene); phenylene di(C
1
-C
4
alkylene); or one of the groups of the formulae (IIIa)-(IIIh)
—CO—R
18
—CO  (IIIa);
—COO—R
19
—OOC—  (IIIb);
—CONH—R
20
—NHCO—  (IIIc);
in which Hal stands for halogen or C
1
-C
4
alkoxy;
R
18
is a direct bond; C
1
-C
12
alkylene; C
2
-C
12
alkylene interrupted by oxygen, sulfur and/or —NR
10
—; C
5
-C
7
cycloalkylene; C
5
-C
7
cycloalkenylene; or phenylene; C
2
-C
8
alkenylene; C
2
-C
8
alkenylene substituted by C
4
-C
12
aryl or C
4
-C
12
aryl which is substituted by C
1
-C
8
alkyl, C
1
-C
8
alkoxy, di(C
1
-C
4
-alkyl)amino, nitro; or C
2
-C
8
alkenylene substituted by thienyl, phenoxyphenyl, phenylthiophenyl, benzo[b]thiophen-2-yl, benzofuran-2-yl, 9H-fluorenyl, biphenylyl, 10H-phenothiazinyl, thiofuranyl;
R
19
is C
2
-C
12
alkylene; C
4
-C
12
alkylene interrupted by 1, 2 or 3 oxygen atoms; C
5
-C
7
cycloalkylene; C
5
-C
7
cycloalkylene di(C
1
-C
4
alkylene); or C
1
-C
4
alkylidene di(C
5
-C
7
cycloalkylene);
R
20
is C
2
-C
12
alkylene; C
5
-C
7
cycloalkylene; phenylene;
R′
20
is C
2
-C
12
alkylene; C
5
-C
7
cycloalkylene; phenylene; and if i is 1, R′
20
additionally embraces methylene;
i is zero or 1;
t is zero or an integer from 1 to 7;
v and z, independently of each other, are an integer from 1 to 4;
when s is 3
W is aliphatic C
4
-C
18
triacyl; cycloaliphatic C
6
-C
18
triacyl or aromatic C
9
-C
18
triacyl; 1,3,5triazine-2,4,6-triyl; or a group of the formulae (IVa-IVb)
where R
22
, R
23
, R
24
, independently of each other, are C
1
-C
7
alkylene;
when s is 4
W is aliphatic C
5
-C
18
tetraacyl; cycloaliphatic C
8
-C
18
tetraacyl or aromatic C
10
-C
18
tetraacyl or a tetravalent residue of the formula Va
Z
1
—NR
10
—R
20
—NR
10
—Z
2
,  (Va)
wherein Z
1
and Z
2
are each, independently of one another, a group of the formula Vb, Vc or Vd
and the group of formula Vb-d is attached via a bond from the triazine ring to the nitrogen atom in formula Va;
when s is 5, W is aliphatic C
7
-C
18
pentaacyl; cycloaliphatic C
10
-C
18
pentaacyl or aromatic C
11
-C
18
pentaacyl;
when s is 6, W is aliphatic C
8
-C
18
hexaacyl; cycloaliphatic or aromatic C
12
-C
18
hexaacyl or a hexavalent residue of the formula VIa
Z
1
—NR
10
—R
20
—N(Z
2
)—R
20
—NR
10
—Z
3
  (VIa)
wherein Z
1
, Z
2
and Z
3
, independently of one another, are a group of the formula Vb, Vc or Vd, which is attached via a bond from the triazine ring to the nitrogen atom in formula VIa;
when s is 7, W is aliphatic, cycloaliphatic or aromatic C
12
-C
18
heptaacyl;
when s is 8, W is aliphatic, cycloaliphatic or aromatic C
12
-C
18
octaacyl or a residue of the formula VIIa
Z
1
—NR
10
—R
20
—N(Z
2
)—R
20
—N(Z
3
)—R
20
—NR
10
—Z
4
  (VIIa)
wherein Z
1
, Z
2
, Z
3
and Z
4
, independently of one another, are a group of the formula Vb, Vc or Vd, which is attached via a bond from the triazine ring to the nitrogen atom in formu

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