Biphenyl-substituted triazines

Details Biphenyl-substituted triazines Biphenyl-substituted triazines

1999-08-25

2001-07-03

Raymond, Richard L. (Department: 1611)

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

active

06255483

ABSTRACT:

The present invention relates to biphenyl-substituted triazine compounds, to processes for the preparation of these compounds, to organic material stabilized with the aid of these compounds against damage by sunlight, heat and oxygen, to the corresponding use of these compounds as stabilizers for organic material, and to their use as light stabilizers for textile fiber materials and as sunscreens for the human skin.
If it is desired to increase the light stability of an organic material, especially a coating, a light stabilizer is usually added. A class of light stabilizers which is very frequently employed comprises the UV absorbers, which protect the material by absorbing the harmful radiation via chromophores. An important group of UV absorbers is the triphenyltriazines, as are described inter alia in EP-A-434 608, EP-A-520 938, U.S. Pat. No. 4,619,956, EP-A-483 488, EP-A-500 496, EP-A-502 816 and EP-A-506 615. Some bis-resorcinyl derivatives from this group are mentioned, for example, in CH-A-480 090, CH-A-484 695, U.S. Pat. Nos. 3,249,608, 3,244,708, 3,843,371, 4,826,978, EP-A-434 608, EP-A-520 938, GB-A-2 273 498 and WO-A-94/18 278.
It has now been found that certain biphenyl-substituted triazine compounds have surprisingly high absorption in the range from 300 to 400 nm which is important for organic polymers.
The novel biphenyl-substituted triazine compounds are of the formula
in which
R
1
is hydrogen; C
1
-C
24
alkyl or C
5
-C
12
cycloalkyl; or C
1
-C
24
alkyl or C
5
-C
12
cycloalkyl, which are substituted by 1 to 9 halogen atoms, —R
4
, —OR
5
, —N((R
5
)
2
, ═NR
5
, ═O, —CON(R
5
)
2
, —COR
5
, —COOR
5
, —OCOR
5
, —OCON(R
5
)
2
;—CN, —NO
2
, —SR
5
, —SOR
5
, —SO
2
R
5
, —P(O)(OR
5
)
2
, a morpholinyl, piperidyl, 2,2,6,6-tetramethylpiperidyl, piperazinyl or N-methylpiperazinyl group, or combinations thereof; and/or C
1
-C
24
alkyl or C
5
-C
12
cycloalkyl which is interrupted by 1 to 6 phenylene, —O—, —NR
5
—, —CONR
5
—, —COO—, —OCO—, —CH(R
5
)—, —C(R
5
)
2
—or —CO— groups or combinations thereof; and R
1
is furthermore C
2
-C
24
alkenyl; halogen; —SR
3
, SOR
3
; SO
2
R
3
; —SO
3
H; —SO
3
M; or a radical of the formula
R
3
is C
1
-C
20
alkyl; C
3
-C
18
alkenyl; C
5
-C
12
cycloalkyl; C
7
-C
15
phenylalkyl, or C
6
-C
12
aryl which is unsubstituted or substituted by 1 to 3 C
1
-C
4
alkyl groups;
R
4
is unsubstituted C
6
-C
12
aryl; or C
6
-C
12
aryl which is substituted by 1 bis 3 halogen atoms, C
1
-C
8
alkyl or C
1
-C
8
alkoxy or combinations thereof; C
5
-C
12
cycloalkyl; unsubstituted C
7
-C
15
-phenylalkyl; or C
7
-C
15
phenylalkyl which is substituted in the phenyl ring by 1 to 3 halogen atoms, C
1
-C
8
alkyl, C
1
-C
8
alkoxy or combinations thereof or C
2
-C
8
alkenyl;
R
5
is R
4
; hydrogen; C
1
-C
24
alkyl; or a radical of the formula
 in which
T is hydrogen; C
1
-C
8
alkyl; C
2
-C
8
alkyl which is substituted by one or more hydroxyl groups or by one or more acyloxy groups; oxyl; hydroxyl; —CH
2
CN;, C
1
C
18
alkoxy; C
5
-C
12
cycloalkoxy; C
3
-C
6
alkenyl; C
7
-C
9
phenylalkyl; C
7
-C
9
phenylalkyl which is substituted one, two or three times in the phenyl ring by C
1
-C
4
alkyl; or aliphatic C
1
-C
8
alkanoyl;
R
6
to R
15
independently of one another are hydrogen; hydroxyl; —C≡N; C
1
-C
20
alkyl; C
1
-C
20
-alkoxy; C
7
-C
20
phenylalkyl; C
4
-C
12
cycloalkyl; C
4
-C
12
cycloalkoxy; halogen; halo-C
1
-C
5
-alkyl; sulfonyl; carboxyl; acylamino; acyloxy; C
1
-C
12
alkoxycarbonyl; aminocarbonyl; —O—Y; or O—Z; or R
8
and R
9
, together with the phenyl radical, are a cyclic radical which is interrupted by one or more oxygen or nitrogen atoms;
M is alkali metal;
p 1 or 2;
q 0 or 1;
and, if q is 0, R
12
and R
13
are not hydroxyl;
if p is 1,
X, Y and Z independently of one another are hydrogen; C
4
-C
50
alkyl which is interrupted by one or more oxygen atoms and/or substituted by one or more hydroxyl groups;
C
4
-C
12
cycloalkyl which is substituted by R
2
; —OR
2
-substituted C
4
-C
12
cycloalkyl; —CH((CH
2
)
n
—R
2
)—CO—O—(CH
2
)
m
—R′
2
; —CH((CH
2
)
n
—R
2
) —CO—(NR′)—(CH
2
)
m
—r′
2
;
—CH
2
—CH(—O(CO)—R
2
)—R′
2
, —CO—NR′—(CH
2
)
n
—R
2
; C
6
-C
12
aryl; allyl; C
4
-C
20
alkenyl which is unsubstituted or is interrupted by one or more oxygen atoms; C
4
-C
12
cycloalkenyl which is unsubstituted or is substituted by one or more oxygen atoms; C
3
-C
20
alkynyl; or C
6
C
12
cycloalkynyl;
R
2
and R′
2
independently of one another are R
x
if attached to a carbon atom and are R
y
if attached to an atom other than carbon;
n 0 to 20;
m 0 to 20;
and, if p is 2,
Y and Z independently of one another are as defined for when p is 1; and
X is C
2
-C
12
alkylene; —CO—(C
2
-C
12
alkylene)—CO—; —CO-phenylene-CO—; CO-biphenylene-CO—; CO—O—(C
2
-C
12
alkylene)—O—CO—; —CO —O-phenylene-O—CO—; —CO—O—biphenylene-O—CO—; —CO—NR′—(C
2
-C
12
alkylene)—NR′—CO—; —CO—NR′-phenylene-NR′—CO—; —CO—NR′-biphenylene-NR′—CO—; —CH
2
—CH(OH) —CH
2
—; —CH
2
—CH(OR
2
) —CH
2
—; —CH
2
—CH(OH)—CH
2
—O—D—O—CH
2
—CH(OH) —CH
2
; —CH
2
—CH(OR
2
)—CH
2
—O—D—O—CH
2
—CH(OR
2
)—CH
2
—;
D is C
2
-C
12
alkylene; C
4
-C
50
alkylene which is interrupted by one or more oxygen atoms; phenylene; biphenylene or phenylene-E-phenylene;
E is —O—; —S—; —SO
2
—; —CH
2
—; —CO—; or —C(CH
3
)
2
—;
R
x
is hydrogen; hydroxyl; C
1
-C
20
alkyl; C
4
-C
12
cycloalkyl; C
1
-C
20
alkoxy; C
4
-C
12
cycloalkoxy; C
4
-C
12
cycloalkyl or C
4
-C
12
cycloalkoxy which is interrupted by one or more oxygen atoms; C
6
-C
12
aryl; hetero-C
3
-C
12
aryl; —OR
z
; NHR
z
; R
z
; CONR′R″; allyl; C
2
-C
20
alkenyl; C
4
-C
12
-cycloalkenyl which is uninterrupted or interrupted by one or more oxygen atoms; C
3
-C
20
-alkynyl; or C
6
-C
12
cycloalkynyl;
R
y
is hydrogen; C
1
-C
20
alkyl; C
4
-C
12
cycloalkyl which is uninterrupted or interrupted by one or more oxygen atoms; C
6
-C
12
aryl; hetero-C
3
-C
12
aryl; R
z
; allyl; C
2
-C
20
alkeny; C
4
-C
12
-cycloalkenyl which is uninterrupted or is interrupted by one or more oxygen atoms; C
3
-C
20
alkynyl; or C
6
-C
12
cycloalkynyl;
R
z
is —COR′; —COOR′; —CONR′R″; —CO—CH═CH
2
; —CO—C(CH
3
)═CH
2
;
R′ and R″ independently of one another are hydrogen; C
1
-C
20
alkyl; C
4
-C
50
alkyl which is interrupted by one or more oxygen atoms; C
4
-C
12
cycloalkyl which is uninterrupted or interrupted by one or more oxygen atoms; C
2
-C
20
alkenyl which is unsubstituted or is interrupted by one or more oxygen atoms; or C
6
-C
12
aryl.
The radicals R
x
, R
y
, R′ and R″ can independently of one another be substituted by hydroxyl, —NH
2
, —NHR′, —NR′R″, halogen, C
1
-C
20
alkyl, C
1
-C
20
alkoxy, C
4
-C
12
cycloalkyl, C
4
-C
12
cycloalkoxy, C
2
-C
20
alkenyl, C
4
-C
12
cycloalkyl, C
3
-C
20
alkynyl, C
6
-C
12
cycloalkynyl, C
6
-C
12
aryl, acylamine, acyloxy, sulfonyl, carboxyl, (meth)acryloxy, (meth)acrylamino,
The abovementioned radicals can also constitute isomer mixtures from the definitions given. When q is 0, compounds are preferred wherein none of R
6
to R
15
is OH or allyloxy, especially wherein none is OH or alkenyloxy.
Alkyl is 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 or octadecyl.
C
1
-C
20
alkoxy comprises straight-chain or branched radicals such as, for example, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, undecyloxy, dodecyloxy, tetradecyloxy or pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, nonadecyloxy or eicosyloxy.
Phenylalkyl is alkyl which is substituted by phenyl. C
7
-C
20
phenylalkyl, for example, compr

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