Stabilizing polycarbonates

Details Stabilizing polycarbonates Stabilizing polycarbonates

2000-03-02

2001-10-30

Solola, T. A. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S310000, C524S482000, C528S354000, C528S361000

Reexamination Certificate

active

06310220

ABSTRACT:

The present invention relates to compositions comprising a polycarbonate, polyester or polyketone which is subject to oxidative, thermal and/or light-induced degradation, or their mixtures and blends, and at least one benzofuran-2-one type compound, to be use thereof for stabilising polycarbonate, polyester or polyketone or their mixtures or blends against oxidative, thermal and/or light-induced degradation, as well as to a process for stabilising these plastic materials.
It is known from, inter alia, R. Gächter and H. Müller, “Plastics Additives Handbook, 3rd Edition”, pages 88/89 (1990) that polycarbonates may be protected by suitable stabiliser mixtures, comprising triarylphosphites or phosphonites and certain phenolic antioxidants, against oxidative damage during their preparation, processing and use.
These known stabiliser mixtures do not meet the high demands made on stabiliser mixtures in all respects, in particular as regards storage stability, absorption of water, susceptibility to hydrolysis, processing stabilisation, colour behaviour, transmission properties, volatility, migration behaviour, compatibility and enhancement of light stabilisation. In the case of amorphous plastics, used e.g. as a substitute for glass, discolorations and reduction in transparency are undesirable while processing or using the plastics. In the case of polyesters, in particular PET, which come into contact with beverages, the degradation products of polyester, such as formaldehyde or acetaldehyde, are extremely undesirable because these can affect the taste of the beverages already at low concentrations. There is therefore still a need for effective stabilisers for polycarbonates, polyesters or polyketones or their mixtures or blends which do not substantially reduce the transparency of these plastics on exposure to light or under oxidative or thermal stress and which largely prevent the yellowing of these plastics and the release of degradation products of these plastics.
The use of the compounds of the benzofuran-2-one type as stabilisers for organic polymers, in particular polyolefins, is known, for example, from U.S. Pat. Nos. 4,325,863; 4,388,244; 5,175,312; 5,252,643; 5,216,052; 5,369,159; 5,488,117; 5,356,966; 5,367,008; 5,428,162; 5,428,177 or U.S. Pat. No. 5,516,920.
It has now been found that these benzofuran-2-one type compounds are particularly suitable as stabilisers for polycarbonates, polyesters or polyketones or their mixtures or blends.
Accordingly, this invention relates to compositions comprising
a) a polycarbonate, polyester or polyketone which is subject to oxidative, thermal and/or light-induced degradation, or their mixtures or blends, and
b) at least one benzofuran-2-one type compound.
Interesting compositions are those, wherein component (b) is a compound of formula I
wherein,
if n=1,
R
1
is naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3b]thienyl, thianthrenyl, dibenzofuryl, chromenyl, xanthenyl, phenoxathiinyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pyridinyl, carbazolyl, &bgr;-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, each of which is unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, hydroxy, halogen, amino, C
1
-C
4
alkylamino, phenylamino or di(C
1
-C
4
-alkyl)amino, or R
1
is a radical of formula II
 and,
if n=2,
R
1
is unsubstituted or C
1
-C
4
alkyl- or hydroxy-substituted phenylene or naphthylene; or —R
12
—X—R
13
—,
R
2
, R
3
, R
4
and R
5
are each independently of one another hydrogen, chloro, hydroxy, C
1
-C
25
alkyl, C
7
-C
9
phenylalkyl, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkyl; C
1
-C
18
alkoxy, C
1
-C
18
alkylthio, C
1
-C
4
alkylamino, di(C
1
-C
4
-alkyl)amino, C
1
-C
25
alkanoyloxy, C
1
-C
25
alkanoylamino, C
3
-C
25
alkenoyloxy; C
3
-C
25
alkanoyloxy which is interrupted by oxygen, sulfur or
 C
6
-C
9
cycloalkyl-carbonyloxy, benzoyloxy or C
1
-C
12
alkyl-substituted benzoyloxy; or R
2
and R
3
, or R
3
and R
4
, or R
4
and R
5
, together with the linking carbon atoms, form a benzene ring, R
4
is additionally —(CH
2
)
p
—COR
15
or —(CH
2
)
q
OH or, if R
3
, R
5
and R
6
are hydrogen, R
4
is additionally a radical of formula III
wherein
R
1
is as defined above for n=1,
R
6
is hydrogen or a radical of formula IV
wherein R
4
is not a radical of formula III, and R
1
is as defined above for n=1,
R
7
, R
8
, R
9
, R
10
and R
11
are each independently of one another hydrogen, halogen, hydroxy, C
1
-C
25
alkyl; C
2
-C
25
alkyl which is interrupted by oxygen, sulfur or
 C
1
-C
25
alkoxy; C
2
-C
25
alkoxy which is interrupted by oxygen, sulfur or
 C
1
-C
25
alkylthio C
3
-C
25
-alkenyl, C
3
-C
25
alkenyloxy, C
3
-C
25
alkynyl, C
3
-C
25
alkynyloxy, C
7
-C
9
phenylalkyl, C
7
-C
9
phenylalkoxy, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; unsubstituted or C
1
-C
4
alkyl-substituted phenoxy; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkyl; unsubstituted or C
1
-C
4
alkyl-substituted C
5
-C
8
cycloalkoxy; C
1
-C
4
alkylamino, di(C
1
-C
4
alkyl)amino, C
1
-C
25
alkanoyl; C
3
-C
25
alkanoyl which is interrupted by oxygen, sulfur or
 C
1
-C
25
alkanoyloxy; C
3
-C
25
alkanoyloxy which is interrupted by oxygen, sulfur or
 C
1
-C
25
alkanoylamino, C
3
-C
25
alkenoyl; C
3
-C
25
alkenoyl which is interrupted by oxygen, sulfur or
 C
3
-C
25
alkenoyloxy; C
3
-C
25
alkenoyloxy which is interrupted by oxygen, sulfur or
 C
6
-C
9
cycloalkylcarbonyl, C
6
-C
9
cycloalkylcarbonyloxy, benzoyl or C
1
-C
12
alkyl-substituted benzoyl; benzoyloxy or C
1
-C
12
alkyl-substituted benzoyloxy;
 or, in formula II, R
7
and R
8
, or R
8
and R
11
, together with the linking carbon atoms, form a benzene ring,
R
12
and R
13
are each independently of the other unsubstituted or C
1
-C
4
alkyl-substituted phenylene or naphthylene,
(R
14
is hydrogen or C
1
-C
8
alkyl,
R
15
is hydroxy,
 C
1
-C
18
alkoxy or
R
16
and R
17
are each independently of the other hydrogen, CF
3
, C
1
-C
12
alkyl or phenyl, or R
16
and R
17
, together with the linking carbon atom, are a C
5
-C
8
cycloalkylidene ring which is unsubstituted or substituted by 1 to 3 C
1
-C
4
alkyl;
R
18
and R
19
are each independently of the other hydrogen, C
1
-C
4
alkyl or phenyl,
R
20
is hydrogen or C
1
-C
4
alkyl,
R
21
is hydrogen, unsubstituted or C
1
-C
4
alkyl-substituted phenyl; C
1
-C
25
alkyl; C
2
-C
25
alkyl which is interrupted by oxygen, sulfur or
 C
7
-C
9
phenylalkyl which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C
1
-C
4
alkyl; C
7
-C
25
phenylalkyl which is interrupted by oxygen, sulfur or
 and which is unsubstituted or substituted at the phenyl moiety by 1 to 3 C
1
-C
4
alkyl, or R
20
and R
21
, together with the linking carbon atoms, form a C
5
-C
12
cycloalkylene ring which is unsubstituted or substituted by 1 to 3 C
1
-C
4
alkyl;
R
22
is hydrogen or C
1
-C
4
alkyl,
R
23
is hydrogen, C
1
-C
25
alkanoyl, C
3
-C
25
alkenoyl; C
3
-C
25
alkanoyl which is interrupted by oxygen, sulfur or
 C
2
-C
25
alkanoyl which is substituted by a di(C
1
-C
6
alkyl)phosphonate group; C
6
-C
9
cycloalkylcarbonyl, thenoyl, furoyl, benzoyl or C
1
-C
12
alkyl-substituted benzoyl;
R
24
and R
25
are each independently of the other hydrogen or C
1
-C
18
alkyl,
R
26
is hydrogen or C
1
-C
8
alkyl,
R
27
is a direct bond, C
1
-C
18
alkylene; C
2
-C
18
alkylene which is interrupted by oxygen, sulfur or
 C
2
-C
18
alkenylene, C
2
-C
20
alkylidene, C
7
-C
20
phenylalkylidene, C
5
-C
8
cycloalkylene, C
7
-C
8
bicycloalkylene,

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