Polyoxyalkylene substituted and bridged triazine,...

Details Polyoxyalkylene substituted and bridged triazine,... Polyoxyalkylene substituted and bridged triazine,...

2000-10-04

2002-04-09

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Carboxylic acid esters

C560S145000, C564S152000, C568S333000

Reexamination Certificate

active

06369267

ABSTRACT:

The invention relates to novel polyoxyalkylene substituted and bridged triazine, benzotriazole and benzophenone derivatives, to their use in particular as UV absorbers, to compositions and materials, including coating compositions, comprising such polyoxyalkylene substituted and bridged triazine, benzotriazole and benzophenone derivatives, to the use of the coating compositions, and to material, especially organic material, which has been stabilized with the novel polyoxyalkylene substituted and bridged triazine, benzotriazole and benzophenone derivatives.
A range of triazine, benzotriazole and benzophenone derivatives which can be used inter alia as UV absorbers are already known. For example U.S. Pat. No. 3,843,371 describes certain hydroxyphenyltriazines and their use in photographic materials; certain 1,3,5-triphenyl-s-triazines, containing two free phenolic OH groups, which are substituted by a polyalkylene radical, are known from GB-A-2 273 498; certain bridged o-hydroxyphenyl-s-triazines, containing as bridge member a —CH
2
—CH(OH)—CH
2
—O—CH
2
—CH
2
—O—CH
2
—CH(OH)—CH
2
— group, and their use as UV absorbers are known from U.S. Pat. No. 5,322,868; and certain o-hydroxyphenyl-s-triazines, bridged by an &agr;,&ohgr;-butylenediol diglycidyl ether radical, are described in EP-A-0 434 608. Furthermore, U.S. Pat. No. 4,853,471 describes a number of 2-(2-hydroxyphenyl)benzotriazoles bridged by way of an &agr;,&ohgr;-butylenediol diglycidyl ether radical and their use as UV absorbers, especially in plastics and in photographic materials, and U.S. Pat. No. 3,580,927 describes certain benzophenone derivatives bridged by way of an &agr;,&ohgr;-butylenediol diglycidyl ether radical. However, none of these documents refers to triazine, benzotriazole or benzophenone derivatives bridged or substituted by an &agr;,&ohgr;-alkanediol diglycidyl ether in which the alkane radical is interrupted one or more times by oxygen.
One of the objects of the invention, then, was to develop further compounds which can be used in particular as UV absorbers and which on the one hand are compatible with polymers and are dispersible in water and which on the other hand can also be used for water-based primers. The properties of a UV absorber are defined not only by the active centre, for example by the spectral properties of the UV-absorbing chromophore. Also of critical importance are those units of the molecule that are the primary determinants of ease of incorporation and mobility in the substrate and of compatibility with the substrate.
The achievement of this object lies in novel polyoxyalkylene substituted and bridged triazine, benzotriazole and benzophenone derivatives, which surprisingly respond very well to the requirements set out above—and set by industry—and which as UV absorbers cover a very wide range of applications.
The invention therefore provides polyoxyalkylene substituted and bridged triazine, benzotriazole and benzophenone derivatives, of the formulae
A
1
—L
1
  (I)
and
A
1
—L
2
—A
1
  (II)
in which:
A
1
independently at each occurrence is a radical of the formula IIIA, IIIB or IIIC
or a radical of the formulae IVA, IVB or IVC
or a radical of the formula VA
B
1
is the bridge member —O— or —NH—,
L
1
is a polyoxyalkylene radical of the formula VI
—CH
2
—CH(OH)—CH
2
—O—(CH
2
—(CH
2
)
u
—O—)
m
—D
1
  (VI)
in which D
1
is hydrogen,
—CH
2
—CH(OH)—CH
2
—OH or R
16
;
or is a polyoxyalkylene radical of the formula VII
—CO—(CH
2
)
u
—O—(CH
2
—(CH
2
)
u
—O—)
m
—D
2
  (VII)
in which D
2
is —(CH
2
)
u
—CO—R
13
or R
16
;
or is a polyoxyalkylene radical of the formula VIII
—Y—O—CO—(CH
2
)
u
—O—(CH
2
—(CH
2
)
u
—O—)
m
—D
3
  (VIII)
in which D
3
is —(CH
2
)
u
—CO—R
13
or R
16
;
or is a polyoxyalkylene radical of the formula IX
—(CH
2
)
k
—CH(R
12
)—CO—B
1
—(C
n
H
2n
—O—)
m
—C
n
H
2n
—B
1
—D
4
  (IX)
in which D
4
is hydrogen or R
16
;
or is a polyoxyalkylene radical of the formula X
—CO—CH
2
—CH
2
—NH—(C
n
H
2n
—O—)
m
—C
n
H
2n
—D
5
  (X)
in which D
5
is —NH
2
, —NH—(CH
2
)
2
—COO—R
14
or —O—R
16
;
or is a polyoxyalkylene radical of the formula XI
—Y—O—CO—CH
2
—CH
2
—NH—(C
n
H
2n
—O—)
m
—C
n
H
2n
—D
5
  (XI)
in which D
5
is as defined under formula (X);
or is a polyoxyalkylene radical of the formula XII
—(C
n
H
2n
—O—)
m
—C
n
H
2n
—D
6
  (XII)
in which D
6
is —NH—CO—R
15
, —OR
16
, OH or H;
or is a polyoxyalkylene radical of the formula XIII
in which D
7
is —OR
16
, —NHCOR
15
or —OCH
2
CH
2
OR
16
;
L
2
is a polyoxyalkylene bridge member of the formula XIV
—CH
2
—CH(OH)—CH
2
—O—(CH
2
—(CH
2
)
u
—O—)
m
—CH
2
—CH(OH)—CH
2
—  (XIV)
or is a polyoxyalkylene bridge member of the formula XV
—CO—(CH
2
)
u
—O—(CH
2
—(CH
2
)
u
—O—)
m
—(CH
2
)
u
—CO—  (XV)
or is a polyoxyalkylene bridge member of the formula XVI
—Y—O—CO(CH
2
)
u
—O—(CH
2
—(CH
2
)
u
—O—)
m
—(CH
2
)
u
COO—Y—(XVI)
or is a polyoxyalkylene bridge member of the formula XVII
—(CH
2
)
k
—CH(R
12
)—CO—B
1
—(C
n
H
2n
—O—)
m
—C
n
H
2n
—B
1
—CO—CH(R
12
)—(CH
2
)
k
—  (XVII)
or is a polyoxyalkylene bridge member of the formula XVIII
or is a polyoxyalkylene bridge member of the formula XIX
—Y—O—CO—(CH
2
)
2
—NH—(C
n
H
2n
—O—)
m
—C
n
H
2n
—NH—(CH
2
)
2
COO—Y—  (XIX)
or is a polyoxyalkylene bridge member of the formula XX
—(C
n
H
2n
—O—)
m
—C
n
H
2n
—  (XX)
or is a polyoxyalkylene bridge member of the formula XXI
—CH(CH
3
)—CH
2
—(O—CH(CH
3
)—CH
2
)
a
—(O—CH
2
—CH
2
)
b
—(O—CH
2
—CH(CH
3
)
c
—  (XXI)
in which: a+c=2.5 and b=8.5 to 40.5 or a+c=2 to 33 and b=0;
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
independently of one another are: hydrogen, C
1
-C
18
alkyl, C
3
-C
6
alkenyl, halogen, C
1
-C
18
alkoxy, aryl, C
1
-C
18
alkoxyaryl, aryl-C
1
-C
4
alkyl, CN, C
1
-C
18
alkyl-S(O)
t
or aryl—S(O)
t
;
R
7
is hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
8
alkoxy, C
3
-C
6
alkenoxy, C
1
-C
18
alkyl-S(O)
t
or aryl-S(O)
t
;
R
8
is hydrogen, C
1
-C
12
alkyl, aryl-C
1
-C
4
alkyl or C
5
-C
12
cycloalkyl;
R
9
is hydrogen, halogen, C
1
-C
18
alkoxy, C
3
-C
6
alkenoxy or aryl-S(O)
t
;
R
10
is hydrogen or OH;
R
11
is hydrogen, C
1
-C
12
alkyl, aryl-C
1
-C
4
alkyl or C
3
-C
6
alkenyl;
R
12
is hydrogen or C
1
-C
16
alkyl;
R
13
is halogen or —O—R
14
;
R
14
is hydrogen, C
1
-C
8
alkyl, C
3
-C
6
alkenyl, aryl or aryl-C
1
-C
4
-alkyl;
R
15
is hydrogen, C
1
-C
12
alkyl or aryl;
R
16
is C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl, C
3
-C
6
alkenyl, C
1
-C
12
alkylaryl or aryl-C
1
-C
4
alkyl;
R
17
is hydrogen or C
1
-C
4
alkyl;
R
18
is hydrogen, C
1
-C
18
alkyl, C
3
-C
6
alkenyl, C
1
-C
18
alkoxy, halogen or aryl-C
1
-C
4
alkyl;
R
19
and R
20
independently of one another are: hydrogen, C
1
-C
18
alkyl, C
3
-C
6
alkenyl, C
1
-C
18
alkoxy or halogen;
R
21
is hydrogen, C
1
-C
4
alkyl or CN;
Y is unsubstituted or substituted C
2
-C
20
alkylene;
k is zero or a number from 1-16,
m is a number from 2-60,
n is the numbers 2 to 6,
p is a number from 2-12,
q is a number from 1-6,
r is zero or 1,
t is zero, 1 or 2, and
u is a number from 1-4.
R
1
to R
6
, R
16
and R
18
to R
20
as C
1
to C
18
alkyl are independently of one another, for example: an unbranched C
1
-C
18
alkyl radical, such as the methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl radical; a branched C
1
-C
18
alkyl radical, such as the sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, 1-methylhexyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, 1-methylundecyl or 1,1,3,3,5,5-hexamethylhexyl radical.
All these C
1
to C
18
alkyl radicals are either unsubstituted or can be substituted one or more times.
R
1
to R
6
, R
11
, R
14
, R
16
and R
18
to R
20
as C
3
to C
6
alkenyl are independently of one another, for example: an unbranched or branched C
3
to C
6
alkenyl radic

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