Light-stabilized organic polymers

Details Light-stabilized organic polymers Light-stabilized organic polymers

1999-11-08

2002-03-05

Yoon, Tae H. (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S100000, C524S102000, C524S103000

Reexamination Certificate

active

06353044

ABSTRACT:

The present invention relates to light-stabilized organic polymers.
More specifically, the present invention relates to organic polymers light-stabilized by the addition, to said organic polymers, of an effective quantity of one or more compounds belonging to the group of enamines consisting of derivatives of &bgr;-keto-esters, or &bgr;-keto-amides or 1,3-diketones with primary or secondary aliphatic or aromatic amines, carrying at least one sterically hindered amine group in the molecule.
It is known that organic polymers undergo degradation over a period of time as a result of exposure to atmospheric agents, and mainly to ultraviolet radiation, and they also easily undergo thermoxidative degradation during processing and transformation processes.
This degradation causes a deterioration in the physical characteristics of organic polymers such as, for example, a reduction in the impact strenght and flexure as well as alterations in the optical properties of the end-article.
Stabilizing compounds are usually introduced into organic polymers to prevent the above degradation.
The Applicant has now found that compounds belonging to the group of enamines consisting of derivatives of &bgr;-keto-esters, or &bgr;-keto-amides or 1,3-diketones with primary or secondary aliphatic or aromatic amines, carrying at least one sterically hindered amine group in the molecule, are capable of stabilizing organic polymers to which they are added improving their resistance to light, in particular, to ultraviolet radiation.
The above compounds are capable of absorbing ultraviolet radiation with a maximum absorption at a wave-length equal to 280 nm. This wave-length has a particularly aggressive action towards organic polymers.
The present invention therefore relates to organic polymers light-stabilized by the addition, to said organic polymers, of an effective quantity of one or more compounds belonging to the group of enamines consisting of derivatives of &bgr;-keto-esters, or &bgr;-keto-amides or 1,3-diketones with primary or secondary aliphatic or aromatic amines, carrying in the molecule at least one sterically hindered amine group, having general formula (I):
wherein
m represents an integer from 1 to 3, extremes included;
n represents an integer from 1 to 4, extremes included;
R
1
represents a triazine having one or the following general formula (II), (III) or (IV):
 wherein R
5
represents a hydrogen atom; a linear or branched C
1
-C
18
alkyl group; a —NHR
6
amine group or a —SR
6
group wherein R
6
represents a hydrogen atom or a linear or branched C
1
-C
18
alkyl group;
R
1
and R
2
, the same or different, represent a hydrogen atom; a linear or branched C
1
-C
8
alkyl group; a linear or branched C
2
-C
8
alkoxyalkyl group; a C
5
-C
8
cycloalkyl group optionally containing a heteroatom selected from oxygen, nitrogen and sulfur; a C
6
-C
18
aryl group; a C
7
-C
20
arylalkyl or alkylaryl group; a group having general formula (V):
 wherein R
7
represents a hydrogen atom; a linear or branched C
1
-C
18
alkyl group, said alkyl group optionally substituted with a —NHR
8
group or an —OR
8
group wherein R
8
represents a hydrogen atom, a linear or branched C
1
-C
18
alkyl group, or a C
6
-C
18
aryl group; an —OR
9
group wherein R
9
represents a hydrogen atom, or a linear or branched C
1
-C
18
alkyl group;
or, R
1
and R
2
considered jointly with the nitrogen atom, represent a C
5
-C
8
heterocyclic group optionally containing a second heteratom selected from oxygen, nitrogen and sulfur;
R
3
and R
4
, the same or different, represent a linear or branched C
1
-C
18
alkyl group; a C
6
-C
18
aryl group; a C
7
-C
20
alkylaryl or arylalkyl group; a linear or branched C
1
-C
8
alkoxyl group;
or, R
4
represents a group having general formula (VI):
 wherein R
7
has the same meanings defined above;
or, R
4
represents an NR
10
R
11
group wherein R
10
and R
11
, the same or different, represent a hydrogen atom; a linear or branched C
1
-C
18
alkyl group; a linear or branched C
2
-C
8
alkoxyalkyl group; a C
5
-C
8
cycloalkyl group optionally containing a heteroatom selected from oxygen, nitrogen and sulfur; a C
6
-C
15
aryl group; a C
7
-C
20
arylalkyl or alkylaryl group; a triazine having one of the following general formula (II), (III) or (IV):
wherein R
5
has the same meanings defined above; a group having general formula (V);
wherein R
7
has the same meanings defined above;
or, R
10
and R
11
considered jointly with the nitrogen atom, represent a C
5
-C
8
heterocyclic group optionally containing a second heteroatom selected from oxygen, nitrogen and sulfur;
or R
4
represents a group having one of the following general formulae (VII), (VIII) or (IX):
wherein:
R
12
represents a hydrogen atom; or a linear or branched C
1
-C
18
alkyl group;
R
13
represents a linear or branched C
1
-C
8
alkyl group; a —COCH
2
COCH
3
group; or a direct bond;
 provided that, when R
1
and R
2
are different from the group having general formula (V), R
4
represents a group having general formula (VI).


REFERENCES:
patent: 4855434 (1989-08-01), Cantatore et al.
patent: 5486613 (1996-01-01), Broussard et al.
patent: 2849444 (1980-05-01), None
patent: 3533451 (1987-03-01), None
patent: 0345221 (1989-12-01), None

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