Stabilized organic material

Details Stabilized organic material Stabilized organic material

1996-01-19

2001-02-13

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

active

06187919

ABSTRACT:

The present invention relates to an organic material containing, as stabilizers, a mixture of a sterically hindered amine and an o-hydroxyphenyl-s-triazine, and to novel o-hydroxyphenyl-s-triazine.
It is already known from U.S. Pat. No. 4,619,956 that polymers can be stabilized against the action of light, moisture and oxygen by adding a mixture of a sterically hindered amine and an o-hydroxyphenyl-s-triazine. The triazines used in this context contain at least one phenyl group carrying a hydroxyl group in the o-position.
Triazine compounds of this type are relatively sparingly soluble in many substrates and tend to migrate. In accordance with the present invention, similar triazine derivatives which have an improved compatibility with or solubility in organic polymers are used.
Ten invention relates to an organic material which has been stabilized against damage caused by light, heat and oxygen and which contains
(a) at least one sterically hindered amine of the polyalkylpiperidine type and
(b) at least one o-hydroxyphenyl-s-triazine, wherein the triazine compound (b) is a compound of the formula I
 in which n is 1 to 4,
R
1
and R
2
independently of one another are H, OH, C
1
-C
12
alkyl, cyclohexyl or tifluor methyl,
R
3
and R
4
independently of one another are H, OH, C
1
-C
12
alkyl, cyclohexyl, C
1
-C
18
-alkoxy or halogen and, in the event that n=1, can also be a radical —OR
7
,
R
5
and R
6
independently of one another are H, C
1
-C
12
alkyl or halogen,
R
7
, if n is 1, is
a) C
1
-C
18
alkyl which is substituted by one or more of the groups OH, C
1
-C
18
alkoxy, C
3
-C
18
alkenoxy, halogen, phenoxy (which is unsubstituted or substituted by C
1
-C
18
alkyl, C
1
-C
18
alkoxy or halogen), furyloxy,
 —COOH, —COOR
8
, —CONH
2
, —CONHR
9
, —CON(R
9
)(R
10
), —NH
2
, —NHR
9
, —N(R
9
)(R
10
), —NHCOR
11
, —CN and/or by —O—CO—R
11
,
b) C
4
-C
50
alkyl which is interrupted by one or more O and can be substituted by OH or/and glycidyloxy,
c) C
3
-C
6
alkenyl,
d) glycidyl or a group
e) cyclohexyl which is unsubstituted or substituted by OH or —OCOR
11
,
f) C
7
-C
11
phenylalkyl which is unsubstituted or substituted by OH, Cl or CH
3
,
g) —CO—R
12
or
h) —SO
2
—R
13
,
and if n is 2, R
7
is
a) C
2
-C
16
alkylene,
b) C
4
-C
12
alkenylene,
c) xylylene,
d) C
3
-C
20
alkylene which is interrupted by one or more O and/or substituted by OH,
e) a group —CH
2
CH(OH)CH
2
O—R
15
—OCH
2
CH(OH)CH
2
—, —CO—R
16
—CO—, —CO—NH—R
17
—NH—CO— or —(CH
2
)
m
—COO—R
18
—OOC—(CH
2
)
m
— (in which m is 1 to 3) or
 and if n is 3, R
7
is a group
 and if n is 4, R
7
is a group
R
8
is C
1
-C
18
alkyl, C
3
-C
18
alkenyl, C
3
-C
20
alkyl which is interrupted by one or more O, N or S and/or substituted by OH, C
1
-C
4
alkyl which is substituted by —P(O)(OR
14
)
2
, —N(R
9
)(R
10
) or —OCOR
11
and/or OH, C
3
-C
18
alkenyl, glycidyl or C
7
-C
11
phenylalkyl,
R
9
and R
10
independently of one another are C
1
-C
12
alkyl, C
3
-C
12
alkoxyalkyl, C
4
-C
16
dialkylamrinoalkyl or C
5
-C
12
cycloalkyl, or R
9
and R
10
together are C
3
-C
9
alkylene or C
3
-C
9
oxaalkylene or C
3
-C
9
azaalkylene,
R
11
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl or phenyl,
R
12
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl, phenyl, C
1
-C
12
alkoxy, phenoxy, C
1
-C
12
alkylamino or C
6
-C
12
arylamino or a group —R
24
—COOH or —NH—R
17
—NCO,
R
13
is C
1
-C
12
alkyl, C
6
-C
12
aryl or C
7
-C
14
alkaryl,
R
14
is C
1
-C
12
alkyl or phenyl,
R
15
is C
2
-C
10
alkylene, C
4
-C
50
alkylene which is interrupted by one or more O, phenylene or a group -phenylene-X-phenylene- in which X is —O—, —S—, —SO, —CH
2
— or —C(CH
3
)
2
—,
R
16
is C
2
-C
10
alkylene, C
2
-C
10
oxaalkylene or C
2
-C
10
thiaalkylene, C
6
-C
12
arylene or C
2
-C
6
alkenylene,
R
17
is C
2
-C
10
alkylene, phenylene, tolylene, diphenylenemethane or a group
R
18
is C
2
-C
10
alkylene or C
4
-C
20
alkylene which is interrupted by one or more O,
R
19
is C
3
-C
12
alkanetiyl,
R
20
is C
4
-C
12
alkanetetryl,
R
23
is C
2
-C
10
alkylene, phenylene or a group
 wherein X is O, S, SO
2
, CH
2
or C(CH
3
)
2
, and
R
24
is C
2
-C
14
alkylene, vinylene or o-phenylene.
If one of the substituents in formula I is C
1
-C
12
alkyl, it can be unbranched or branched alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, i-butyl, s-butyl or t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, di-t-octyl, nonyl, decyl, undecyl or dodecyl. As C
1
-C
18
alkyl, R
8
, R
11
, and R
12
can additionally be, for example, tetradecyl, hexadecyl or octadecyl.
As C
1
-C
18
alkoxy, R
3
and R
4
are preferably C
1
-C
12
alkoxy. The alkoxy radical is preferably unbranched Examples of these are methoxy, ethoxy, propoxy, butoxy, hexyloxy, octyloxy, decyloxy or dodecyloxy.
As substituted C
1
-C
12
alkyl, R
7
can be substituted by one or more of the groups OH, C
1
-C
18
alkoxy, halogen, phenoxy which is unsubstituted or substituted by C
1
-C
18
alkyl, C
1
-C
18
alkoxy or halogen, —COOH, —COOR
8
, —CONII
2
, —CONHR
9
, —CON(R
9
)(R
10
), —NH
2
, —NHR
9
, —NH(R
9
)(R
10
), —NHCOR
11
, —CN or —OCOR
11
. The following groups are examples of such substituted alkyl groups: —CH
2
CH
2
OH, —CH
2
CH(OH)CH
3
, —CH
2
CH(OH)C
2
H
5
, —CH
2
CH(OH)C
6
H
13
, —CH
2
CH(OH)C
10
H
21
, —CH
2
CH
2
OCH
3
, —CH
2
CH
2
OC
2
H
5
, —CH
2
CH
2
OC
4
H
9
, —(CH
2
)
3
OH, —CH
2
CH(OH)CH
2
OC
4
H
9
, —CH
2
CH(OH)CH
2
OC
12
H
25
, —CH
2
CH
2
Ophenyl, —CH
2
CH
2
Cl, —CH
2
CH(OH)CH
2
Ophenyl,
—CH
2
COOH, —CH
2
CH
2
COOH, —CH
2
COOC
2
H
5
, —CH
2
COOC
8
H
17
, —CH
2
CH
2
COOCH
3
, —CH
2
CH
2
COOC
4
H
9
, —CH
2
CH
2
COOC
12
H
25
, —CH
2
CONH
2
, —CH
2
CONHC
4
H
9
, —CH
2
CON(C
4
H
9
)
2
, —CH
2
CH
2
CONHC
12
H
25
, —CH
2
CH
2
CON(C
2
H
5
)
2
, —CH
2
CH
2
NH
2
, —CH
2
CH
2
N(CH
3
)
2
, —(CH
2
)
3
—NH
2
, —(CH
2
)
3
—NHC
4
H
9
, —(CH
2
)
3
N(CH
3
)
2
, —(CH
2
)
3
N(C
2
H
5
)
2
, —(CH
2
)
3
NHCOCH
3
, —(CH
2
)
3
NHCOC
7
H
15
, —CH
2
CH
2
CN, —CH
2
CH
2
OCOC
3
H
7
, —CH
2
CH
2
OCOC
17
H
35
, —CH
2
CH(CH
3
)—OCOCH
3
, —CH
2
CH(OCOCH
3
)CH
2
OC
8
H
17
or —CH
2
CH(OCOC
7
H
15
)CH
2
Ophenyl.
As C
3
-C
6
alkenyl, R
7
can, for example, be allyl, methallyl or 2-butenyl. As C
3
-C
18
alkenyl, R
8
can additionally also be, for example, octenyl, dodecenyl or oleyl. As C
2
-C
18
alkenyl, R
11
and R
12
can additionally also be vinyl.
As C
7
-C
11
phenylalkyl which is unsubstituted or substituted by OH, Cl or CH
3
, R
7
and R
8
can, for example, be phenylethyl, 2-hydroxy-2-phenylethyl, 2-phenylpropyl, 3-phenylpropyl, 4-chlorobenzyl or 4methylbenzyl, but especially benzyl.
As C
2
-C
16
alkylene, R
7
can be unbranched or branched alkylene, for example di-, tri-, tetra-, hexa-, octa-, deca- or dodeca-methylene, 2,2-dimethyl-prop-1,3-ylene or 1,2-propylene. As C
4
-C
12
alkenylene, R
7
can, in particular, be 2-buten-1,4-ylene. As C
3
-C
20
alkylene which is interrupted by O and/or substituted by OH, R
7
can, for example, be one of the groups —CH
2
CH(OH)CH
2
—, —CH
2
CH
2
OCH
2
CH
2
— or —CH
2
CH(OH)CH
2
O—(CH
2
)
x
—OCH
2
CH(OH)CH
2
— in which x=2-10.
As C
3
-C
20
alkyl which is interrupted and/or substituted by OH, R
8
can, in particular, be alkyl which is substituted by OH or alkyl which is interrupted by O and substituted by OH. Examples of these are the groups —CH
2
CH
2
OH, —CH
2
CH(OH)CH
3
, —CH
2
CH(OH)C
6
H
13
, —CH
2
CH
2
OC
4
H
9
, —CH
2
CH
2
OCH
2
CH
2
OH or —CH
2
CH
2
(OCH
2
CH
2
)
p
OH in which p=2-9.
As C
1
-C
4
alkyl which is substituted by —P(O)(OR
14
)
2
, —N(R
9
)(R
10
) or —OCOR
11
, R
8
can, for example, be —CH
2
CH
2
P(O)(OC
2
H
5
)
2
, —CH
2
P(O)(OC
6
H
13
)
2
, —CH
2
CH
2
N(CH
3
)
2
, —CH
2
CH
2
CH
2
N(C
2
H
5
)
2
, —CH
2
CH
2
OCOC
7
H
15
or —CH
2
CH
2
OCOCH═CH
2
.
As C
3
-C
12
alkoxyalkyl, R
9
and R
10
can, in particular, be 2-(C
1
-C
10
alkoxy)-ethyl, for example 2-methoxyethyl, 2-butoxyethyl or 2-octyloxyethyl. As C
4
-C
16
dialkylaminoalkyl, R
9
and R
10
can, for example, be 2-dibutylaminoethyl, 2-diethylaminoethyl or 3-dimethylaminopropyl.
As C
5
-C
12
cycloalkyl, R
9
and R
10
can, for example, be cyclopentyl, cyclooctyl or cyclododecyl, but especial

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