Paint stabilizer

Details Paint stabilizer Paint stabilizer

1998-10-12

2001-04-17

Chang, Celia (Department: 1625)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C526S217000, C526S263000, C526S265000, C546S187000, C546S188000, C546S190000

Reexamination Certificate

active

06218451

ABSTRACT:

The present invention relates to the use of a photoreactive, UV-absorbing piperidine compound and of a mixture consisting of this piperidine compound and at least one UV absorber as light stabilizers in coating materials, preferably automotive coating materials.
The invention also provides a method of stabilizing coating materials against the degradation of the polymer material present in the coating material, as induced by the effect of atmospheric oxygen, heat and/or UV light, and the coating materials themselves that have been stabilized in this way.
The effects of atmospheric oxygen, moisture and, in particular, UV light in coating materials lead to a degradation of the polymer material present in the coating material. This manifests itself, for example, in cracking, loss of gloss, colour changes, delamination and blistering. It is known that such processes in coating materials can be retarded by using appropriate stabilizers. Known coating compositions therefore often include a mixture of a UV absorber and a sterically hindered amine (HALS: hindered amine light stabilizer). It is known that these compounds of the HALS type react as free-radical scavengers and are therefore generally employed for the stabilization of polymeric substrates.
It has now been found that a specific, sterically hindered amine of the formula (A) below, which is photoreactive and absorbs UV light, is particularly suitable, alone or in combination with UV absorbers or mixtures of different UW absorbers, as a light stabilizer for coating materials, especially automotive coating materials.
The invention therefore provides for the use of a piperidine compound of the following formula (A) (referred to below as HALS A)
for increasing the light stability of coating materials. A further embodiment of the invention relates to the use of a mixture consisting of this photoreactive, UV-absorbing piperidine compound and at least one UV absorber selected from the group consisting of 2-hydroxyphenylbenzotriazoles (1), 2-hydroxyphenyltriazines (2), 2-hydroxybenzophenones (3), oxalanilides (4) and cinnamic acid derivatives (5) as a light stabilizer in coating materials.
Suitable 2 -hydroxyphenylbenzotriazoles correspond to the formulae [sic] (1a) or (1b)
where, in the compounds of the formula (1a),
R
1
is hydrogen, alkyl having 1 to 24 carbon atoms, preferably alkyl having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, butyl, hexyl, octyl, nonyl, dodecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl and eicosyl, and corresponding branched isomers, or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, in particular benzyl.
R
2
is hydrogen, halogen, in particular chlorine and bromine, alkyl having 1 to 18 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, in particular benzyl, &agr;-methylbenzyl, cumyl.
R
3
is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms, in particular methyl, butyl, at least one of the radicals R
1
and R
2
being other than hydrogen, and
where, in the compounds of the formula (1b),
T is hydrogen or alkyl having 1 to 6 carbon atoms, in particular methyl and butyl
T
1
is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms, in particular methyl
n is 1 or 2 and
T
2
, if n is 1, is chlorine or a radical of the formula —OT
3
, and, if n is 2, is a radical of the formula —O—T
9
—O—, where
T
3
is hydrogen, alkyl having 1 to 18 carbon atoms which is optionally substituted by from 1 to 3 hydroxyl groups, alkyl having 3 to 18 carbon atoms which is interrupted one or more times by —O— and is optionally substituted by hydroxyl, alkenyl having 2 to 18 carbon atoms which is optionally substituted by hydroxyl (suitable alkenyl radicals are derived from the alkyl radicals ab which are listed in the definitions of R
1
), phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, in particular benzyl, phenylethyl, cumyl, &agr;-methylbenzyl, or is a radical of the formula —CH
2
CH(OH)—T
7
,
T
7
is hydrogen, alkyl having 1 to 18 carbon atoms or phenyl,
T
9
is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, or alkylene having 2 to 18 carbon atoms which is interrupted one or more times by —O—, where the alkylene or alkenylene radicals may also be branched.
Suitable 2-hydroxyphenyltriazines correspond to the formula (2)
where
u is 1 or 2,
r is an integer from 1 to 3,
Y
1
independently of one another are hydrogen, hydroxyl, halomethyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms or halogen,
Y
2
, if u is 1, is alkyl having 1 to 18 carbon atoms, or is alkyl having 1 to 12 carbon atoms which is substituted by hydroxyl, alkoxy having 1 to 18 carbon atoms, halogen, by —COOH, —COOY
8
, —CONH
2
, —CONHY
9
, —CONY
9
Y
10
, —CN and/or —OCOY
11
, or is alkyl having 4 to 20 carbon atoms which is interrupted by one or more oxygen atoms and is optionally substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms, or is alkenyl having 3 to 6 carbon atoms, or is glycidyl, or is phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety and unsubstituted or substituted by hydroxyl, chlorine and/or methyl, or is —COY
12
or —SO
2
Y
13
, or
Y
2
, if u is 2, is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylylene, alkylene having 3 to 20 carbon atoms which is interrupted by one or more —O— and/or is substituted by hydroxyl, or is —CH
2
CH—(OH)CH
2
—O—Y
15
—OCH
2
CH(OH)CH
2
, or is —(CH
2
)
m
—CO
2
—Y
18
—OCO—(CH
2
)
m
, in which m is 1, 2 or 3,
Y
8
is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl having 3 to 20 carbon atoms which is interrupted by one or more oxygen atoms and/or is substituted by hydroxyl, or is glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety,
Y
9
and Y
10
independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cycloalkyl having 5 to 12 carbon atoms,
Y
11
is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl,
Y
12
is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms, or phenylamino,
Y
13
is alkyl having 1 to 18 carbon atoms, phenyl, alkylphenyl having 1 to 8 carbon atoms in the alkyl radical,
Y
15
is alkylene having 2 to 20 carbon atoms, phenylene or a group -phenylene-M-phenylene, in which M is —O—, —S—, —SO
2
—, —CH
2
— or —C(CH
3
)
2
—, and
Y
18
is alkylene having 2 to 10 carbon atoms or is alkylene having 4 to 20 carbon atoms which is interrupted one or more times by oxygen.
Suitable 2-hydroxybenzophenone correspond to the formula (3)
where
v is an integer from 1 to 3,
w is 1 or 2, and
Z independently of one another is hydrogen, halogen, hydroxyl or alkoxy having 1 to 12 carbon atoms.
Suitable oxalanilides correspond to the formula (4)
where
x is an integer from 1 to 3
y is 1 or 2 and
L independently of one another is H, alkyl having 1 to 20 carbon atoms, hydroxyl or alkoxy having 1 to 20 carbon atoms. In this formula the substituents L are preferably in ortho and/or para position.
Examples of alkyl, alkoxy, phenylalkyl, alkylene, alkenylene, alkoxyalkyl and cycloalkyl radicals and of alkylthio, oxaalkylene or azoalkylene radicals in the compounds of the formulae (2), (3), (4) and (5) can be taken from the above remarks.
Suitable cinnamic acid derivatives correspond to the formula (5)
where
n is an integer from 1-4
U
1
is H, alkyl, hydroxyl, alkoxy, NH
2
, NHalkyl, N-dialkyl
U
2
is H, alkyl, aryl, alkyl-substituted aryl, alkoxyaryl, p-hydroxyaryl, p-aminoaryl
U
3
is H, CN, COOU
6
U
4
if n is 1, is alkyl (n, iso, cyclo) of 1 to 20 carbon atoms that is uninterrupted or interrupted one or more times by —O—,
if n is 2, is alkylene (n, iso, cyclo) of 1 to 20 carbon atoms that is uninterrupted or interrupted one or more times by —O—,
if n is 3, is the radical of a triol such as trimethylolpropane, propanetriol
if n is 4, is the radical o

Affiliated with

Also associated with

Rating

Paint stabilizer does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Paint stabilizer, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Paint stabilizer will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2523754