Phenol-free stabilization of polyolefin fibres

Details Phenol-free stabilization of polyolefin fibres Phenol-free stabilization of polyolefin fibres

1997-06-23

2003-02-18

Szekely, Peter (Department: 1714)

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

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S102000, C524S103000, C524S104000, C524S111000, C524S117000, C524S118000, C524S119000, C524S120000, C524S126000, C524S128000, C524S135000, C524S151000, C524S405000

Reexamination Certificate

active

06521681

ABSTRACT:

The present invention relates to compositions comprising an organic material subject to oxidative, thermal or light-induced degradation, especially polyolefins, for example polyolefin fibres, and as stabilizers at least one compound of the benzofuran-2-one type and at least one compound of the sterically hindered amine type, and to the use thereof for stabilizing organic materials against oxidative, thermal or light-induced degradation.
The use of compounds of the benzofuran-2-one type as stabilizers for organic polymers 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 5,516,920.
Sterically hindered amines, including in particular compounds containing 2,2,6,6-tetramethylpiperidyl groups, are known as “hindered amine” light stabilizers (HALS).
The known stabilizers do not satisfy in every respect the high requirements which a stabilizer is required to meet, especially with regard to shelf life, water absorption, sensitivity to hydrolysis, in-process stabilization, colour properties, volatility, migration behaviour, compatibility and improvement in protection against light. As a result there continues to be a need for effective stabilizers for organic materials, especially polyolefins, for example polyolefin fibres, that are sensitive to oxidative, thermal and/or light-induced degradation.
Polyolefin fibres have to date been stabilized with sterically hindered phenols in combination with compounds from the group of the organic phosphites or phosphonites and, in some cases, with additional use of light stabilizers. The use of such stabilizer mixtures leads in many cases to yellowing of the polyolefin fibres thus produced, especially under the action of NO
x
gas, referred to in the art as gas fading. In many cases discoloration occurs even during processing, especially in the case of melt extrusion. It is also known that compounds from the group of the sterically hindered amines, which may be added as light stabilizers, show an antagonistic effect together with the sterically hindered phenols, which adversely effects the long-term thermal stability.
It has now been found that a stabilizer mixture comprising at least one compound of the benzofuran-2-one type and at least one compound of the sterically hindered amine type is particularly suitable as a stabilizer for organic materials which are sensitive to oxidative, thermal or light-induced degradation. Such phenol-free stabilization systems exhibit, in particular, excellent stabilization of polyolefins in the course of processing to polypropylene fibres, for example. These novel stabilizer systems suppress the discoloration of the organic materials during processing, have an excellent action in respect of resistance to the effect of NO
x
(no gas fading) and, moreover, exhibit improved long-term thermal stability relative to stabilization systems which include phenolic antioxidants. The sterically hindered amines, which replace the phenolic long-term thermal stabilizers, additionally provide good protection against photooxidative degradation of the organic material.
The present invention therefore provides compositions comprising
a) an organic material which is subject to oxidative, thermal or light-induced degradation,
b) at least one compound having a benzofuran-2-one moiety, and
c) at least one compound having a sterically hindered amine radical.
The present invention also provides compositions comprising, in addition to components (a), (b) and (c), also d) at least one compound from the group of the organic phosphites or phosphonites.
Compositions which are of interest include those comprising as component (b) a compound of the formula I
in which, if n is 1,
R
1
is unsubstituted or C
1
-C
4
alkyl-, C
1
-C
4
alkoxy-, C
1
-C
4
alkylthio-, hydroxyl-, halo-, amino-, C
1
-C
4
alkylamino-, phenylamino- or di(C
1
-C
4
alkyl)amino-substituted naphthyl, phenanthryl, anthryl, 5,6,7,8-tetrahydro-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, thienyl, benzo[b]thienyl, naphtho[2,3-b]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, pteridinyl, carbazolyl, &bgr;-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, isothiazolyl, phenothiazinyl, isoxazolyl, furazanyl, biphenyl, terphenyl, fluorenyl or phenoxazinyl, or R
1
is a radical of the formula II
and
if n is 2,
R
1
is unsubstituted or C
1
-C
4
alkyl- or hydroxy-substituted phenylene or naphthylene; or is —R
12
—X—R
13
—,
R
2
, R
3
, R
4
and R
5
independently of one another are hydrogen, chlorine, hydroxyl, 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
cycloalkylcarbonyloxy, benzoyloxy or C
1
-C
12
alkyl-substituted benzoyloxy; or else the radicals R
2
and R
3
or the radicals R
3
and R
4
or the radicals R
4
and R
5
, together with the carbon atoms to which they are attached, form a benzo 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 the formula III
in which
R
1
is defined as indicated above for n=1,
R
6
is hydrogen or a radical of the formula IV
where
R
4
is not a radical of the formula III and R
1
is defined as indicated above for n=1,
R
7
, R
8
, R
9
, R
10
and R
11
independently of one another are hydrogen, halogen, hydroxyl, C
1
-C
25
alkyl, C
2
-C
25
alkyl interrupted by oxygen, sulfur or
 C
1
-C
25
alkoxy, C
2
-C
25
alkoxy 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 interrupted by oxygen, sulfur or
 C
1
-C
25
alkanoyloxy, C
3
-C
25
alkanoyloxy interrupted by oxygen, sulfur or
 C
1
-C
25
alkanoylamino, C
3
-C
25
alkenoyl, C
3
-C
25
alkenoyl interrupted by oxygen, sulfur or
 C
3
-C
25
alkenoyloxy, C
3
-C
25
alkenoyloxy 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 else, in formula II, the radicals R
7
and R
8
or the radicals R
8
and R
11
, together with the carbon atoms to which they are attached, form a benzo ring,
R
12
and R
13
independently of one another are unsubstituted or C
1
-C
4
alkyl-substituted phenylene or naphthylene,
R
14
is hydrogen or C
1
-C
8
alkyl,
R
15
is hydroxyl,
 C
1
-C
18
alkoxy or
 R
16
and R
17
independently of one another are hydrogen, CF
3
, C
1
-C
12
alkyl or phenyl, or R
16
and R
17
, together with the C atom to which they are attached, form a C
5
-C
8
cycloalkylidene ring which is unsubstituted or substituted from 1 to 3 times by C
1
-C
4
alkyl;
R
18
and R
19
independently of one another are 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 interrupted by oxygen, sulfur or
 C
7
-C
9
phenylalkyl which is unsubstituted or substituted on the phenyl radical from 1 to 3 times by C
1
-C

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