Hydroxyphenyl triazines

Details Hydroxyphenyl triazines Hydroxyphenyl triazines

1997-11-19

2001-02-06

Sanders, Kriellion (Department: 1714)

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S216000

Reexamination Certificate

active

06184375

ABSTRACT:

The invention relates to novel compounds of the hydroxyphenyl-s-triazine type containing one blocked and 2 free o-hydroxyl groups, to the use of these compounds for stabilizing organic material, especially in plastics, coating materials, cosmetic preparations, sun screen lotions or photographic material, against damage by light, oxygen and/or heat, and to correspondingly stabilized organic material.
When it is desired to increase the stability of an organic material, especially a coating, to light, 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 harmful radiation via chromophores. One important group of UV absorbers are the triphenyl-s-triazines, as are described, inter alia, in the publications U.S. Pat. No. 3,118,887, U.S. Pat. No. 3,242,175, U.S. Pat. No. 3,244,708, GB-A-1 321 561, EP-A-0 434 608, U.S. Pat. No. 4,619,956, U.S. Pat. No. 5,364,749, U.S. Pat. No. 5,461,151, EP-A-0 704 437 and WO-96/28431.
Also known are individual compounds of the hydroxyphenyl-s-triazine type some or all of whose hydroxyl groups in ortho position are blocked (U.S. Pat. No. 3,113,940, U.S. Pat. No. 3,113,941, U.S. Pat. No. 3,113,942, GB-A-975 966, U.S. Pat. No. 3,249,608: U.S. Pat. No. 5,597,854, WO-94/05645).
Specific compounds from the class of the trisaryl-s-triazines have now been found which, surprisingly, possess particularly good stabilizer properties. The invention therefore provides a compound of the formula I
in which
R
1
is C
1
-C
18
alkyl; C
5
-C
12
cycloalkyl; C
3
-C
18
alkenyl; phenyl; C
1
-C
18
alkyl which is substituted by phenyl, OH, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
3
-C
18
alkenyloxy, halogen, —COOH, —COOR
4
, —O—CO—R
5
, —O—CO—O—R
6
, —CO—NH
2
, —CO—NHR
7
, —CO—N(R
7
)(R
8
), CN, NH
2
, NHR
7
, —N(R
7
)(R
8
), —NH—CO—R
5
, phenoxy, C
1
-C
18
alkyl-substituted phenoxy, phenyl-C
1
-C
4
alkoxy, C
6
-C
15
bicycloalkoxy, C
6
-C
15
bicycloalkylalkoxy, C
6
-C
15
bicycloalkenylalkoxy, or C
6
-C
15
tricycloalkoxy; C
5
-C
12
cycloalkyl which is substituted by OH, C
1
-C
4
alkyl, C
2
-C
6
alkenyl or —O—CO—R
5
; —CO—R
9
or —SO
2
—R
10
; or R
1
is C
3
-C
50
alkyl which is interrupted by one or more oxygen atoms and/or substituted by OH, phenoxy or C
7
-C
18
alkylphenoxy;
or R
1
is one of the definitions —A; —CH
2
—CH(XA)—CH
2
—O—R
12
; —CR
13
R′
13
—(CH
2
)
m
—X—A;
—CH
2
—CH(OA)—R
14
; —CH
2
—CH(OH)—CH
2
—XA;
 —CR
15
R′
15
—C(═CH
2
)—R″
15
; —CR
13
R′
13
—(CH
2
)
m
—CO—X—A;
 —CR
13
R′
13
—(CH
2
)
m
—CO—O—CR
15
R′
15
—C(═CH
2
)—R″
15
or —CO—O—CR
15
R′
15
—C(═CH
2
)—R″
15
, where A is —CO—CR
16
═CH—R
17
; the radicals
R
2
, independently of one another, are C
6
-C
18
alkyl; C
2
-C
6
alkenyl; phenyl; C
7
-C
11
phenylalkyl; COOR
4
; CN; NH—CO—R
5
; halogen; trifluoromethyl; —O—R
3
;
R
3
embraces the definitions given for R
1
;
R
4
is C
1
-C
18
alkyl; C
3
-C
18
alkenyl; phenyl; C
7
-C
11
phenylalkyl; C
5
-C
12
cycloalkyl; or is C
3
-C
50
alkyl, which is interrupted by one or more —O—, —NH—, —NR
7
—, —S— and can be substituted by OH, phenoxy or C
7
-C
18
alkylphenoxy;
R
5
is H; C
1
-C
18
alkyl; C
2
-C
18
alkenyl; C
5
-C
12
cycloalkyl; phenyl; C
7
-C
11
phenylalkyl C
6
-C
15
bicycloalkyl; C
6
-C
15
bicycloalkenyl; C
6
-C
15
tricycloalkyl;
R
6
is H; C
1
-C
18
alkyl; C
3
-C
18
alkenyl; phenyl; C
7
-C
11
phenylalkyl; C
5
-C
12
cycloalkyl
R
7
and R
8
, independently of one another are C
1
-C
12
alkyl; C
3
-C
12
alkoxyalkyl; C
4
-C
16
dialkylaminoalkyl; or are C
5
-C
12
cycloalkyl; or together are C
3
-C
9
alkylene, C
3
-C
9
oxaalkylene or C
3
-C
9
azaalkylene;
R
9
is C
1
-C
18
alkyl; C
2
-C
18
alkenyl; phenyl; C
5
-C
12
cycloalkyl; C
7
-C
11
phenylalkyl; C
6
-C
15
bicycloalkyl, C
6
-C
15
bicycloalkylalkyl, C
6
-C
15
bicycloalkenyl, or C
6
-C
15
tricyloalkyl;
R
10
is C
1
-C
12
alkyl; phenyl; naphthyl or C
7
-C
14
alkylphenyl;
the radicals R
11
independently of one another are H; C
1
-C
18
alkyl; C
3
-C
6
alkenyl; phenyl; C
7
-C
11
phenylalkyl; halogen; C
1
-C
18
alkoxy;
R
12
is C
1
-C
18
alkyl; C
3
-C
18
alkenyl; phenyl; phenyl which is substituted by one to three radicals C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
3
-C
8
alkenoxy, halogen or trifluoromethyl;
or is C
7
-C
11
phenylalkyl; C
5
-C
12
cycloalkyl; C
6
-C
15
tricycloalkyl; C
6
-C
15
bicycloalkyl; C
6
-C
15
bicycloalkylalkyl; C
6
-C
15
bicycloalkenylalkyl; —CO—R
5
; or is C
3
-C
50
alkyl which is interrupted by one or more —O—, —NH—, —NR
7
—, —S— and can be substituted by OH, phenoxy or C
7
-C
18
alkylphenoxy;
R
13
and R′
13
independently of one another are H; C
1
-C
18
alkyl; phenyl;
R
14
is C
1
-C
18
alkyl; C
3
-C
12
alkoxyalkyl; phenyl; phenyl-C
1
-C
4
alkyl;
R
15
, R′
15
and R″
15
independently of one another are H or CH
3
;
R
16
is H; —CH
2
—COO—R
4
; C
1
-C
4
alkyl; or CN;
R
17
is H; —COOR
4
; C
1
-C
17
alkyl; or phenyl;
X is —NH—; —NR
7
—; —O—; —NH—(CH
2
)
p
—NH—; or —O—(CH
2
)
q
—NH—;
and the indices
m is a number 0-19;
n is a number 1-8;
p is a number 0-4; and
q is a number 2-4;
where at least one of the radicals R
1
, R
2
and R
11
in formula I contains 2 or more carbon atoms.
Preferably, at least one of the radicals R
1
, R
2
, R
11
in formula I and in formula II below contains 3 or more carbon atoms, especially 4 or more carbon atoms.
Within the scope of the stated definitions the radicals R
1
to R
10
, R
12
to R
14
, R
16
and R
17
as alkyl are branched or unbranched alkyl, for example methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-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-methylun-decyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl.
The radicals R
1
, R
3
to R
9
and R
12
as C
5
-C
12
cycloalkyl comprise cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl. Preference is given to cyclopentyl, cyclohexyl, cyclooctyl and cyclododecyl.
Within the scope of the stated definitions, R
1
to R
6
, R
9
, R
11
, and R
12
as alkenyl embrace, inter alia, allyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl, n-dodec-2-enyl or n-octadec-4-enyl.
Substituted alkyl, cycloalkyl or phenyl radicals can be substituted one or more times and can carry substituents on the bonding carbon atom (in &agr;-position) or on other carbon atoms; if the substituent bonds by means of a heteroatom (for example alkoxy) it is preferably not in &agr;-position and the substituted alkyl radical contains 2, especially 3, or more carbon atoms. Two or more substituents bond preferably to different carbon atoms.
Alkyl interrupted by —O—, —NH—, —NR
7
—, —S— can be interrupted by one or more of these groups, one group in each case being inserted, in general into one bond, and hetero-hetero bonds, for example O—O, S—S, NH—NH, etc., not occurring; if the interrupted alkyl is additionally substituted, the substituents are generally not &agr; to the heteroatom. If two or more interrupting groups of the type —O—, —NH—, —NR
7
—, —S— occur in one radical, they are usually identical.
Aryl is generally an aromatic hydrocarbon radical, for example phenyl, biphenylyl or naphthyl, preferably phenyl and biphenylyl. Aralkyl is generally alkyl substituted by aryl, especially by phenyl; thus C
7
-C
20
aralkyl comprises, for example, benzyl, &agr;-methylbenzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl and phenylhexyl; C
7
-C
11
phenylalkyl preferably embraces benzyl, &agr;-methylbenzyl and &agr;,&agr;-dimethylbenzyl.
Alkylphenyl and alkylphenoxy are alkyl-substituted phenyl and phenoxy, respectively.
A halogen substituent is —F, —Cl, —Br or —I; preference is given to —F or —Cl, especially —C

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