Stabilization of paints with spiroindane derivatives

Details Stabilization of paints with spiroindane derivatives Stabilization of paints with spiroindane derivatives

1999-01-27

2001-03-06

Cain, Edward J. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

Reexamination Certificate

active

06197861

ABSTRACT:

The invention relates to coating compositions containing spiroindane compounds and to novel spiroindane compounds.
Antioxidants are needed in thermosetting coatings to prevent oxidation of the binder on curing and overbaking. NO
x
present in the burner gases of ovens causes an additional problem by reacting, with preferentially aromatic components in the binder, to form yellow breakdown products.
It is the usual practice in paints to use a stabiliser combination of a hindered phenol and a phosphite, for example octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate or tetrakis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxymethyl)methane with 2,4-di-tert-butylphenylphosphite.
For better gas oven stability a phosphite is usually used alone.
DE-A-4306 747 teaches the use of the combination of a phosphite and a 2,2,6,6-tetramethylpiperidine compound (HALS) in one molecule as stabiliser for powder paints.
Phosphites on their own give only slight protection against oxidation in air. In the presence of NO
x
they mostly do not yellow, but remain largely ineffective.
The hindered phenols give much better protection against oxidation, particularly when used together with phosphites, but are themselves highly prone to yellowing in the presence of NO
X
.
A number of patents by Fuji Photo Film KK claim the spiroindanes and their use in colour photographic films and papers as light fading preventing agents for the magenta pyrazolone-azomethine and pyrazolotriazole-azomethine dyes: GB-A-2077 455, DE-A-3221 883, JP-A-57204 035 and EP-A-355 660. U.S. Pat. No. 5,411,847 and GB-A-2 201 254 disclose similar structures in photographic applications.
The present invention is based on the discovery that the problem of yellowing of paints on curing in gas(or oil-)-fired ovens can be solved through use of certain specific spiroindane derivatives, either alone or with other stabilisers, preferably phosphites.
The invention relates to a composition comprising:
(A) a powder coating material
(B) at least one compound of formula
wherein R
1
,R
2
, R
3
and R
4
are independently of one another:
a) C
1
-C
18
unsubstituted alkyl or C
1
-C
18
alkyl substituted by one or more of the groups OH, C
1
-C
18
alkoxy, C
2
-C
18
alkenyloxy, halogen, phenoxy (which is unsubstituted or substituted by C
1
-C
18
alkyl, C
1
-C
18
alkoxy or halogen), COOR
8
, —CONH
2
, —CONHF
9
or —CONR
9
R
10
;
b) C
5
-C
12
cycloalkyl which is unsubstituted or substituted by OH or —OCOR
11
;
c) a five or six-membered heterocycle that is saturated or unsaturated;
d) C
7
-C
11
phenylalkyl, which is unsubstituted or substituted by one or more OH, Cl or CH
3
;
e) C
2
-C
18
alkenyl;
f) C
4
-C
30
alkyl which is interrupted by one or more O atoms and can be substituted by OH;
g) —CO—R
12
or —(CH
2
)
n
—CO—R
12
;
h) —SO
2
—R
13
;
n is 1 to 18;
R
5
is H, C
1
-C
18
straight chain or branched alkyl, C
2
-C
18
alkenyl or C
6
-C
12
aryl;
R
6
and R
7
are independently of one another H, halogen, C
1
-C
18
alkyl, C
2
-C
6
alkenyl, C
1
-C
12
alkoxy or C
2
-C
12
alkenyloxy;
R
8
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl, C
3
-C
20
alkyl which is interrupted by one or more O, NR
9
or S and/or substituted by OH, C
1
-C
4
alkyl which is substituted by —P(O)(OR
18
)
2
, C
3
-C
8
alkynyl or C
7
-C
11
phenylalkyl;
R
9
and R
10
are independently of one another 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 C
3
-C
9
oxaalkylene or C
3
-C
9
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, C
1
-C
12
alkoxy, phenoxy, C
1
-C
12
alkylamino or C
6
-C
12
arylamino or a group —R
19
—COOH;
R
13
is C
1
-C
12
alkyl, C
6
-C
12
aryl or C
7
-C
14
alkaryl;
R
14
is hydrogen, oxyl, hydroxy, —CH
2
CN, C
1
-C
18
alkyl, C
1
-C
18
— alkoxy, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
5
-C
8
cycloalkyl or -alkoxy, phenyl, naphthyl, C
7
-C
12
phenylalkyl or -alkoxy, phenyl or phenylalkyl substituted by alkyl or phenyl of 7-14 carbon atoms, C
3
-C
5
alkenoyl, C
1
-C
18
alkynoyloxy, benzyloxy or a group CH
2
—CH(OH)—Z where z is H, CH
3
or Phenyl,
or a group of the formula
wherein
D′ is C
1
-C
18
alkyl, C
1
-C
18
alkoxy, phenyl, or phenyl substituted by hydroxy, C
1
-C
8
alkyl, C
1
-C
8
alkoxy, amino or amino mono- or disubstituted by C
1
-C
8
alkyl or phenyl.
R
15
is H, C
1
-C
18
alkyl or C
3
-C
18
alkyl interrupted by one or more oxygen atoms, cyanoethyl, benzyl, glycidyl, a monovalent radical of an aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acid, or of carbamic acid, or of a phosphorus-containing acid, or a monovalent silyl radical —Si(R
21
)(R
22
)(R
23
);
R
16
is H, —CO—R
11
, —Si(R
21
)(R
22
)(R
23
), or —COOR
24;
;
R
17
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl, phenyl-C
1
-C
4
alkyl, C
3
-C
24
alkyl or C
2
-C
14
hydroxyalkyl, each of which is interrupted by one or more O atoms, or is phenyl, which is unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy or halogen, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1-3 C
1
-C
8
alkyl, or —COR
11
, or
R
18
is C
1
-C
18
alkyl or phenyl;
R
19
is C
1
-C
18
alkylene, vinylene or phenylene;
R
20
is H, OH, oxyl, C
1
-C
18
alkyl, C
2
-C
18
alkenyl, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkyl, C
5
-C
12
cycloalkoxy, C
3
-C
8
alkynyl, C
7
-C
12
phenylalkyl, C
1
-C
8
alkanoyl, C
3
-C
5
alkenoyl or glycidyl;
R
21
, R
22
and R
23
are independently of one another C
1
-C
6
alkyl or phenyl;
Preferred spiroindane derivatives which can be used according to the invention are of formula I, herein
R
5
is H;
R
1
,R
2
, R
3
and R
4
are the same and can be
a) C
1
-C
18
straight chain or branched alkyl, optionally substituted by one or more of the groups OH, C
1
-C
18
alkoxy, C
2
-C
18
alkenyloxy, —COOR
8
, —CONH
2
, —CONHR
9
, —CONR
9
R
10
;
b) C
5
-C
12
cycloalkyl which is unsubstituted or substituted by OH or —OCOR
1
i
c) tetrahydropyran;
e) C
2
-C
18
alkenyl;
f) C
4
-C
30
alkyl which is interrupted by one or more O atoms and can be substituted by OH;
g) —CO—R
12
or —(CH
2
)
n
—CO—R
12
;
n is 1 to 18;
R
6
and R
7
are independently of one another H or C
1
-C
8
alkyl;
R
8
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl, C
3
-C
20
alkyl which is interrupted by one or more 0 or substituted by OH or is C
3
-C
8
alkynyl;
R
9
and R
10
are independently of one another C
1
-C
12
alkyl, C
3
-C
12
alkoxyalkyl or C
5
-C
12
cycloalkyl;
R
11
is C
1
-C
18
alkyl or C
2
-C
18
alkenyl;
R
12
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl, C
1
-C
12
alkoxy, C
1
-C
12
alkylamino or a group R
19
—COOH,
R
14
is especially C
1
-C
12
alkyl, allyl, cyclohexyl, benzyl, acetyl, acryloyl, Cyclohexyloxy or C
1
-C
12
-alkyoxy
R
15
is H or C
1
-C
18
alkyl optionally interrupted by one or more oxygen atoms;
R
16
is H, —CO—R
11
, —Si(R
21
)(R
22
)(R
23
), or —COOR
24;
;
R
17
is C
1
-C
18
alkyl, C
2
-C
18
alkenyl, C
3
-C
24
alkyl or C
2
-C
14
hydroxyalkyl, each of which is interrupted by one or more O atoms, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by 1-3 C
1
-C
8
alkyl, or —COR
11
, or is
R
19
is C
1
-C
18
alkylene or vinylene;
R
20
is H, OH, oxyl, C
1
-C
18
alkyl, C
2
-C
18
alkenyl, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkyl, C
5
-C
12
cycloalkoxy, C
3
-C
8
alkynyl, C
1
-C
8
alkanoyl, C
3
-C
5
alkenoyl or glycidyl;
R
21
, R
22
and R
23
are independently of one another C
1
-C
6
alkyl;
R
24
is C
1
-C
4
alkyl.
Particularly preferred spiroindane derivatives which can be used according to the invention are of formula I wherein
R
5
, R
6
and R
7
are H;
R
1
,R
2
, R
3
and R
4
are the same and can be either:
a) C
1
-C
18
straight chain or branched alkyl;
b) cyclohexyl;
e) allyl;
f) C
3
-C
12
alkyl which is interrupted by one or more O atoms;
g) —CO—R
12;
n is 1 to 6;
R
12
is C
1
-C
4
alkyl or C
2
-C
3
alkenyl;
R
14
is C
1
-C
12
alkyl, benzyl, or C
5
-C
8
cycloalkyl; most preferably C
6
-C
10
alkyl or cyclohexyl.
R
15
is H or C
1
-C
18
alkyl optionally interrupted by one or more oxygen atoms;
R
16
is H, —CO—R
11
or —COOR
24
;

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