Coating compositions stabilized against damage by light,...

Details Coating compositions stabilized against damage by light,... Coating compositions stabilized against damage by light,...

1997-06-23

2004-03-16

Raymond, Richard L. (Department: 1624)

Compositions

Preservative agents

Anti-oxidants or chemical change inhibitants

C252S401000, C252S405000, C544S335000

Reexamination Certificate

active

06706215

ABSTRACT:

The invention relates to coating compositions stabilized against damage by light, heat and oxygen, which contain as stabilizer a 2-(2′-hydroxyphenyl)-1,3-pyrimidine derivative, to new compounds of the 2-(2′hydroxyphenyl)-1,3-pyrimidine type, to their use for stabilizing organic material and to corresponding compositions.
If it is desired to increase the light stability of an organic material, especially a coating, it is conventional to add a light stabilizer. One class of light stabilizers which is very frequently employed is that of the UV absorbers, which protect the material by absorbing the damaging radiation via chromophores. The most commonly used types of UV absorbers are 2-hydroxybenzophenones and 2-(2-hydroxyphenyl)benzotriazoles. In more recent literature, triphenyl-triazines are also mentioned as stabilizers for coating materials, for example in the publications U.S. Pat. No. 4,619,956, EP-A-434 608, EP-A-442 847 and EP-A-502 816, or as stabilizers for polycarbonate (U.S. Pat. No. 5,288,778).
Some o-hydroxy-substituted triphenylpyrimidines have also already been proposed as light stabilizers.
U.S. Pat. No. 3,442,898 describes the protective action of some compounds of this type against UV radiation in, for example, acetylcellulose, polyamide, polyvinyl chloride and polypropylene.
The teaching of U.S. Pat. No. 4,895,981 comprises their use as light stabilizers for polyester fibre materials.
Heller and Blattmann, Pure Appl. Chem. 36, 141 (1973) report on the use of some o-hydroxy-substituted triphenylpyrimidines in polyester. They come to the conclusion that these compounds, in polyester, have a comparatively small light stabilization effect and contribute to the accelerated discolouration of the substrate.
It has now been found that certain 2-(2′-hydroxyphenyl)-1,3-pyrimidine derivatives are surprisingly good stabilizers for coating compositions.
The invention relates to a coating composition comprising
A) a binder based on an organic polymer and
B) as stabilizer against damage by light, heat and oxygen, a compound of the formula I
 in which
R
1
and R
2
independently of one another are H; OH; C
1
-C
12
alkyl; cyclohexyl or trifluoromethyl;
R
3
and R
4
independently of one another have one of the definitions of R
7
or are OR
7
or halogen;
R
5
has one of the definitions given for R
7
or is halogen; —O—CO—R
12
; —O—SO
2
—R
13
or —O—R
7
;
R
6
is H; C
2
-C
18
alkenyl; —X—Z
3
; benzoyl which is unsubstituted or substituted on the phenyl ring by methyl, halogen, —CN or methoxy; —C(Z
3
)═N—Z
3
; —CH(Z
3
)—NH—Z
3
; a radical of the formula
 or a radical of the formula
R
7
is hydrogen; C
1
-C
18
alkyl; C
5
-C
18
alkyloxycarbonyl; or C
2
-C
18
alkenyl; or R
7
is C
1
-C
18
alkyl which is substituted by OH, C
1
-C
18
alkoxy, C
2
-C
18
alkanoyl, C
2
-C
8
alkenyloxy, halogen, —COOH, —COOR
8
, —CONH
2
, —CONHR
9
, —CON(R
9
)(R
10
), —NH
2
, —NHR
9
, —N(R
9
)(R
10
), —NHCOR
11
, —CN, —OCOR
11
, a group of the formula
 and/or phenoxy which is unsubstituted or is substituted by C
1
-C
18
alkyl, C
1
-C
18
alkoxy or halogen; or R
7
is C
4
-C
20
alkyl which is interrupted by O and substituted by OH or C
1
-C
12
alkoxy; glycidyl; C
5
-C
8
cycloalkyl; cyclohexyl which is substituted by OH, C
1
-C
4
alkyl or —OCOR
11
; or C
7
-C
11
phenylalkyl which is unsubstituted or substituted by OH, Cl or CH
3
;
R
8
is C
1
-C
18
alkyl; C
2
-C
6
hydroxyalkyl; C
3
-C
18
alkenyl; C
3
-C
20
alkyl which is interrupted by 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; glycidyl; cyclohexyl or C
7
-C
11
phenylalkyl; or is a group of the formula
R
9
and R
10
independently of one another are C
1
-C
12
alkyl; C
3
-C
12
alkoxyalkyl; C
4
-C
16
dialkylaminoalkyl or C
5
-C
12
cycloalkyl or
R
9
and R
10
together are C
3
-C
9
alkylene or -oxaalkylene or -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; or —R
15
—O—CO—R
11
; or is a group of the formula
R
13
is C
1
-C
12
alkyl; phenyl; naphthyl or C
7
-C
14
alkylphenyl; and
R
14
is C
1
-C
12
alkyl or phenyl;
R
15
is C
1
-C
18
alkylene or C
2
-C
18
alkenylene;
R
16
is hydrogen; oxide; C
1
-C
8
alkanoyl; C
1
-C
18
alkyl; C
2
-C
18
-hydroxyalkyl; C
3
-C
18
hydroxyalkyl which is interrupted by O; C
1
-C
18
alkoxy; C
5
-C
8
cycloalkyl; C
5
-C
8
cycloalkoxy; C
7
-C
11
phenylalkyl; C
7
-C
11
phenylalkyl which is substituted on the phenyl ring by from 1 to 3 radicals C
1
-C
4
-alkyl or C
1
-C
8
alkanoyl; or C
7
-C
11
phenylalkoxy;
X is a direct bond or —CO—;
Z
1
and Z
2
independently of one another are C
1
-C
12
alkyl or together are C
4
-C
10
alkylene which may be interrupted by an oxygen atom;
Z
3
is C
1
-C
20
-Alkyl; and
Z
4
is hydrogen or methyl.
A halogen substituent is —F, —Cl, —Br or —I; it is preferably —Cl or —Br, especially —Cl.
In formula I the line protruding into the phenyl ring and carrying the symbol R
6
is a substituent which is located at one of the three remaining free positions, in the o-, m- or p-position to the phenolic OH group.
The substituent R
6
is preferably in the o- or p-position to the phenolic OH group, especially in the p-position.
R
6
includes, for example, hydrogen, C
1
-C
12
alkyl; C
6
-C
18
alkanoyl; benzoyl; methylbenzoyl; dimethylbenzoyl; benzoyl which is substituted by —Cl, —Br, —CN or —OCH
3
; &agr;-methylbenzyl; &agr;,&agr;-dimethylbenzyl; N,N-dialkylaminomethyl; 1-piperidylmethyl; 1-(4-oxapiperidyl)methyl; an imide of an acyl radical; and &agr;-(N-alkylamino)alkyl. R
6
is preferably hydrogen, C
1
-C
6
alkyl, benzoyl, &agr;-methylbenzyl, allyl or a radical of the formula
for example hydrogen or C
1
-C
6
-alkyl or allyl, particularly hydrogen or methyl and especially hydrogen.
Alkyl R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
16
, Z
1
and Z
2
in the context of the definitions given 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 and octadecyl. Alkyl R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
and R
16
is preferably C
1
-C
8
alkyl, especially C
1
-C
4
alkyl such as methyl or tert-butyl, in particular methyl.
R
6
as alkanoyl is, for example, acetyl, propionyl, butyryl, valeryl, caproyl, caprylyl, caprinyl, lauroyl, myristyl, palmitoyl, or stearyl; C
6
-C
18
-alkanoyl is preferred.
Examples of C
1
-C
18
alkoxy R
3
, R
4
, R
5
and R
16
are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy or octadecyloxy; preference is given to C
4
-C
12
alkoxy, for example n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octyloxy, 1-ethylhexyloxy, n-nonyloxy and n-decyloxy.
Substituted C
1
-C
12
alkyloxy R
3
, R
4
and R
5
is preferably alkoxyalkyloxy, hydroxyalkyloxy interrupted by O, alkyloxy substituted by
or alkyloxy which is substituted by alkenyloyloxy and/or hydroxyl; particularly interesting examples of R
3
, R
4
and R
5
are —OCH
2
CH
2
OCOCH═CH
2
, —OCH
2
CH(OH)C
8
H
17
, —OCH
2
CH(OH)C
12
H
25
, —OCH
2
CH(OH)CH
2
OC
8
H
17
, —OCH
2
CH(OH)CH
2
O—(CH
2
&Parenclosest;
12-14
CH
3
, —OCH
2
CH(OH)CH
2
OCOC(CH
3
)═CH
2
, —OCH
2
CH(OH)CH
2
OCOCH═CH
2
,
R
1
, R
2
, R
3
and R
4
are particularly preferably hydrogen or methyl. Of particular interest are compounds in which the radicals R
1
, R
2
, R
3
and R
4
are identical.
C
3
-C
18
-Alkenyl R
7
, R
8
, R
11
and R
12
comprises, inter alia, allyl, isopropenyl, 2-butenyl,

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