Triresorcinyl triazines

Details Triresorcinyl triazines Triresorcinyl triazines

1999-05-03

2002-02-12

Shah, Mukund J. (Department: 1624)

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C252S403000

Reexamination Certificate

active

06346619

ABSTRACT:

The invention relates to novel compounds of the 2,4,6-tris(2-hydroxyphenyl)-1,3,5-triazine type, to organic material such as organic polymers or prepolymers stabilized with the aid of these novel compounds, especially coating material, and to the use of these compounds as stabilizers, especially for wood or automobile coatings.
If it is desired to increase the photostability of an organic material such as a coating, it is common to add a light stabilizer. One very frequently employed class of light stabilizers are the UV absorbers, which protect the material by absorbing the damaging radiation by way of chromophores. One important group of UV absorbers is the triphenyltriazines; certain compounds of this type, containing branched ester groups, are described in EP-A-434608, EP-A-530135, U.S. Pat. No. 5,364,749, GB-A-2312210, U.S. Pat. No. 5,489,503 and GB-A-2319523.
For a compound to be an effective stabilizer, not only its spectral and antioxidant properties but also, inter alia, its compatibility with the material to be stabilized and its solubility are of critical importance (see GB-A-2312210).
It has now been found that some compounds of the 2-(2′-hydroxyphenyl)-4,6-diaryl-1,3,5-triazine type which contain specific branched acid or ester side chains do surprisingly have particularly good stabilizer properties and substrate compatibility.
The invention therefore first provides a compound of the formula I
in which Z, Z′ and Z″ independently of one another are a group of the formula II
R
7
is a radical of the formula III, IV or V
in which n is 1 or 2;
R
4
, R
5
and R
6
independently of one another are C
1
-C
18
alkyl; C
5
-C
12
cycloalkyl; C
2
-C
18
alkenyl; phenyl; C
7
-C
11
phenylalkyl; C
7
-C
11
alkylphenyl; C
1
-C
18
alkyl substituted by phenyl, OH, halogen; C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
3
-C
18
alkenyloxy, COOH, COOR
11
, O—COR
12
, CONH
2
, CONHR
13
, CONR
13
NR
14
, CN,NH
2
, NHR
13
, NR
13
R
14
, NHCOR
12
, C
6
-C
15
bicycloalkyl, C
6
-C
15
bicycloalkoxy, C
6
-C
15
bicycloalkenyl, C
6
-C
15
bicycloalkenyloxy, C
6
-C
16
bicycloalkyl-alkoxy C
6
-C
16
bicycloalkenyl-alkoxy or C
6
-C
15
tricycloalkoxy; C
5
-C
12
cycloalkyl substituted by OH, C
1
-C
4
alkyl, C
2
-C
6
alkenyl or O—COR
12
; or COR
15
; CO—X—R
8
; or SO
2
—R
16
; or C
3
-C
50
alkyl interrupted by O and/or substituted by OH, phenoxy, or C
7
-C
18
alkylphenoxy; or R
5
and R
6
, together with the carbon atom to which they are attached, form a C
4
-C
8
cycloalkyl ring which is uninterrupted or interrupted by O, NH, NR
13
, or S and/or unsubstituted or substituted by C
1
-C
6
alkyl, C
1
-C
6
alkoxy, OH, phenoxy or C
7
-C
18
alkylphenoxy;
R
8
is H or as defined for R
11
;
R
9
is C
3
-C
18
alkyl; C
3
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
1
-C
4
alkylcyclohexyl; C
6
-C
14
aryl; C
7
-C
11
phenylalkyl; C
7
-C
14
alkylphenyl; C
6
-C
15
bicycloalkyl; C
6
-C
15
bicycloalkenyl; C
6
-C
16
tricycloalkyl; or C
1
-C
18
alkyl substituted by halogen, COOH, COOR
11
, O—COR
12
, CONH
2
, CONHR
13
, CONR
13
R
14
, CN, NH
2
, NHR
13
, NR
13
R
14
, NHCOR
12
, C
6
-C
15
bicycloalkyl, C
6
-C
15
bicycloalkenyl; especially C
6
-C
12
alkyl;
R
11
is C
1
-C
18
alkyl; C
5
-C
12
cycloalkyl; C
6
-C
14
aryl; C
2
-C
18
alkenyl; C
7
-C
14
alkylphenyl; C
1
-C
18
alkyl substituted by phenyl, phenoxy, naphthyl, naphthyloxy, OH, halogen, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
3
-C
18
alkenyloxy, COOH, COOR
11
, O—COR
12
, CONH
2
, CONHR
13
, CONR
13
R
14
, CN, NH
2
, NHR
13
, NR
13
R
14
, NHCOR
12
, C
6
-C
15
bicycloalkyl, C
6
-C
15
bicylcloalkoxy, C
6
-C
15
bicycloalkenyl, C
6
-C
15
bicycloalkenyloxy, C
6
-C
16
bicycloalkyl-alkoxy, C
6
-C
16
bicycloalkenyl-alkoxy or C
6
-C
15
tricycloalkoxy or by a phenyl, phenyloxy or naphthyloxy, which itself is substituted by halogen, OH, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
8
alkylamino, cyclohexylamino, C
1
-C
8
alkylthio, cyclohexylthio; or R
11
is C
5
-C
12
cycloalkyl substituted by OH, C
1
-C
4
alkyl, C
2
-C
6
alkenyl or O—COR
12
; or is COR
15
; CO—X—R
8
; or SO
2
-R
16
; or a carbon-linked 5-7 membered heterocyclic residue containing 4-12 carbon and 1-3 heteroatoms selected from O, N and S; or R
11
is C
3
-C
50
alkyl interrupted by O, NH, NR
13
, S and/or substituted by OH, phenoxy, C
3
-C
18
alkenoxy, C
7
-C
18
alkylphenoxy, O—COR
12
, O—P(═O)(OR
12
)
2
, O—P(═O)(R
12
)
2
, O—Si(OR
12
)
3
;
R
12
is C
1
-C
18
alkyl; C
2
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
1
-C
4
alkylcyclohexyl; C
6
-C
14
aryl; C
7
-C
11
phenylalkyl; C
7
-C
14
alkylphenyl; C
6
-C
15
bicycloalkyl; C
6
-C
15
bicycloalkenyl; C
6
-C
15
tricycloalkyl;
R
13
and R
14
independently of one another are C
1
-C
18
alkyl; C
2
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
1
-C
4
alkylcyclohexyl; C
6
-C
14
aryl; C
7
-C
11
phenylalkyl; C
7
-C
14
alkylphenyl; or C
3
-C
30
alkyl interrupted by O, NH or NR
13
and/or substituted by OH; or are C
6
-C
15
bicycloalkyl; C
6
-C
15
bicycloalkenyl; or C
6
-C
15
tricycloalkyl;
R
15
is C
1
-C
18
alkyl; C
2
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
6
-C
14
aryl; C
7
-C
11
phenlalkyl; or C
7
-C
14
alkylphenyl;
R
16
is C
1
-C
18
alkyl; C
2
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
6
-C
14
aryl; C
7
-C
11
phenylalkyl; or C
7
-C
14
alkylphenyl;
R
17
is CH
2
—O—R
15
or furfuryl or tetrahydrofurfuryl or is C
3
-C
30
alkyl interrupted by O, NH, NR
13
and/or substituted by OH; and
X and Y independently of one another are O, NH, NR
13
or S,
with the exception of the compound 2,4,6-tris(2-hydroxy-4-[1-ethyloxycarbonyl-1-methylethoxy]phenyl)-1,3,5-triazine.
Where two or more radicals bearing the same designation appear within a single compound of the formula I, they may be identical or else different within the scope of the possible definitions indicated. Of particular importance are compounds of the invention in which radicals with the same designation have the same definition.
A halogen substituent is —F, —Cl, —Br or —I, preferably —F, —Cl or —Br and, in particular, —Cl.
C
6
-C
14
aryl is generally phenyl, biphenylyl or a corresponding fused carbocyclic aromatic radical; preference is given to phenyl and naphthyl.
Alkylphenyl is alkyl-substituted phenyl; C
7
-C
14
alkylphenyl embraces examples such as methylphenyl (tolyl), dimethylphenyl (xylyl), trimethylphenyl (mesityl), ethylphenyl, propylphenyl, butylphenyl, dibutylphenyl, pentylphenol, hexylphenyl, heptylphenyl and octylphenyl.
Phenylalkyl is phenyl-substituted alkyl; C
7
-C
11
phenylalkyl embraces examples such as benzyl, &agr;-methylbenzyl, &agr;-ethylbenzyl, &agr;,&agr;-dimethylbenzyl, phenylethyl, phenylpropyl, phenylbutyl and phenylpentyl.
Glycidyl is 2,3-epoxypropyl.
n-alkyl or alkyl-n is an unbranched alkyl radical.
Alkyl interrupted by O, NH, NR
13
, etc., can generally comprise one or more nonadjacent heteroatoms. Preferably, a carbon atom of the alkyl chain bonds to not more than 1 heteroatom.
Within the scope of the stated definitions, the radicals R
4
, R
5
, R
6
, R
8
, R
9
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
as alkyl are branched or unbranched alkyl such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.
C
1
-C
4
alkyl is especially methyl, ethyl, isopropyl, n-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
Within the scope of the stated definitions, R
4
, R
5
, R
6
, R
8
, R
9
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
as alkenyl include allyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl; R
8
further includes n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-octadec-2-enyl and n-octadec-4-enyl. In the case of R
12
and R
15
, for example, vinyl is another possible definition.
R
4
, R
5
and R
6
, independently, are preferably C

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