Plasticized polymer compositions

Details Plasticized polymer compositions Plasticized polymer compositions

2002-03-13

2003-09-23

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...

C524S171000, C524S514000, C524S567000, C524S593000

Reexamination Certificate

active

06624218

ABSTRACT:

The present invention relates to semi-crystalline polymer compositions plasticized with aromatic sulphonamides in which the nitrogen atom contains a substituent carrying a hydroxyl or oxycarbonyl group.
The problem of plasticizers in polymers is well known in the state of the art. Reference may be made, on this subject, to the work “Encyclopedia of Polymer Science and Engineering”, published by Wiley, 1989, Supplement Vol., pp. 568-647, for example, or alternatively to the book “The Technology of Plasticizers”, J. K. Sears and J. R. Darby, John Wiley and Sons Inc., 1982.
It is well known that semi-crystalline polymers, such as polyamide-6, polyamide-6,6, polyamides-4,6, -6,10 and -6,12 and some polyketones, are very difficult to plasticize because of their high melting temperature and of the low compatibility between these polymers and the plasticizers known in the state of the art. This is because, if it is desired to incorporate a plasticizer above these high melting temperatures, typically from 250 to 300° C., and even 340° C. for polyamide-4,6, the plasticizer rapidly degrades, colouring the polymer, and its destruction does not make it possible to effectively plasticize the polymer; in addition, the plasticizer can also evaporate. Such is the case if attempts are made to use, as plasticizer for these polyamides, N-n-butylbenzenesulphonamide or N-ethyl-p-toluenesulphonamide, for example, plasticizers widely used on an industrial scale to plasticize polyamides with lower melting temperatures. One way of alleviating these disadvantages is to process the polymer so that the plasticizer is only found at a high temperature for the shortest possible time but this way of operating causes great technical difficulties, including very high losses of the plasticizer, problems of air pollution related to the sudden evaporation and/or thermal degradation of the plasticizer, and the like.
In addition to the criterion of good thermal stability which must be exhibited by plasticizers for semi-crystalline polymers with high melting temperatures, there is also the problem of the possible migration from the polymer of these plasticizers with time.
As regards semi-crystalline polymers which have lower melting temperatures, such as polyamide-11, polyamide-12, polyoxymethylene or poly(vinylidene fluoride), for which polymers a plasticizer is incorporated at temperatures of the order of 220° C., the problem of the thermal stability of the plasticizer is less critical. However, the intrinsic volatility of a plasticizer such as N-n-butylbenzenesulphonamide can be the source of problems, such as a loss of the product, and smells, which will have to be eliminated by means of complex and expensive equipment.
It would therefore be advantageous to find plasticizers for semi-crystalline polymers with high melting temperatures, such as polyamide-6, polyamide-6,6, polyamides-4,6, -6,9, -6,10, -6,12 and MXD-6 and some polyketones, but also polyamide-11, polyamide-12, polyoxymethylene and poly(vinylidene fluoride), which would be stable at high temperatures ranging from 220 to 300° C. and even 340° C. for polyamide-4,6 without undergoing either consequent decomposition or consequent evaporation. These plasticizers should not migrate towards the surface of the polymer either, in order to avoid the problem of exudation. In addition, it goes without saying that these plasticizers should effectively exhibit plasticizing properties at least equivalent to and preferably better than those of the plasticizers known in the state of the art.
The Applicant Company has now found, surprisingly, a family of aromatic sulphonamides in which the nitrogen atom contains a substituent carrying a hydroxyl or oxycarbonyl group which fully meets all the requirements mentioned above for plasticizers for semi-crystalline polymers with a high melting temperature and a processing temperature equal to or greater than 220° C., preferably 250° C.
For this reason, the present invention relates to compositions comprising at least one polymer and at least one plasticizer, characterized in that
a. the polymer is semi-crystalline and exhibits a processing temperature equal to or greater than 220° C., preferably 250° C.,
b. the plasticizer is an aromatic benzenesulphonamide represented by the general formula (I)
in which
R
1
represents a hydrogen atom, a C
1
-C
4
alkyl group or a C
1
-C
4
alkoxy group,
X represents a linear or branched C
2
-C
10
alkylene group, or
a cycloaliphatic group, or
an aromatic group,
Y represents one of the groups OH or
 R
2
representing a C
1
-C
4
alkyl group or an aromatic group, these groups optionally themselves being substituted by an OH or C
1
-C
4
alkyl group.
The preferred aromatic benzenesulphonamides of formula (I) are those in which:
R
1
represents a hydrogen atom or a methyl or methoxy group,
X represents a linear or branched C
2
-C
10
alkylene group or a phenyl group,
Y represents an OH or —O—CO—R
2
group,
R
2
representing a methyl or phenyl group, the latter being themselves optionally substituted by an OH or methyl group.
The semi-crystalline polymers to which the present invention relates are those for which the processing temperature is equal to or greater than 220° C., preferably 250° C., this processing temperature being imposed by the high melting temperature of these polymers. Mention may be made, among these, of polyamide-6, polyamide-6,6 and some polyketones, on account of the plasticization problems which they pose by virtue of their high melting temperature. The polyketones concerned here are condensation products of carbon monoxide with aliphatic olefins, for example the condensation product of carbon monoxide with ethene and propene. These polyketones are well known in the state of the art (mention may be made, without implied limitation, of Patents EP 485,058, EP 213,671 and EP 121,965, for example). The present invention also relates to polyamides-4,6, -6,9, -6,10, -6,12 and MDX-6. Other semi-crystalline polymers, such as polyamide-11, polyamide-12, polyoxymethylene and poly(vinylidene fluoride), can also be advantageously plasticized by the aromatic sulphonamides of formula (I).
Mention may be made, among the aromatic sulphonamides of formula (I) which are liquid (L) or solid (S) at room temperature as specified below, of the following products, with the abbreviations which have been assigned to them:
AS: N-(2-hydroxyethyl)benzenesulphonamide C
6
H
5
SO
2
NH(CH
2
)
2
OH (L)
AY: N-(3-hydroxypropyl)benzenesulphonamide C
6
H
5
SO
2
NH(CH
2
)
3
OH (L)
BC: N-(2-hydroxyethyl)-p-toluenesulphonamide CH
3
C
6
H
4
SO
2
NH(CH
2
)
2
OH (S)
BE: N-(4-hydroxyphenyl)benzenesulphonamide C
6
H
5
SO
2
NHC
6
H
4
OH (S)
BF: N-[(2-hydroxy-1-hydroxymethyl-1-methyl)ethyl]-benzenesulphonamide C
6
H
5
SO
2
NHC(CH
3
)(CH
2
OH)CH
2
OH (L)
BG: N-[5-hydroxy-1,5-dimethylhexyl]benzenesulphonamide C
6
H
5
SO
2
NHCH(CH
3
)(CH
2
)
3
C(CH
3
)
2
OH (S)
BH: N-(2-acetoxyethyl)benzenesulphonamide C
6
H
5
SO
2
NH(CH
2
)
2
OCOCH
3
(S)
BI: N-(5-hydroxypentyl)benzenesulphonamide C
6
H
5
SO
2
NH(CH
2
)
5
OH (L)
BK: N-[2-(4-hydroxybenzoyloxy)ethyl]benzene-sulphonamide C
6
H
5
SO
2
NH(CH
2
)
2
OCOC
6
H
4
OH (S)
BL: N-[2-(4-methylbenzoyloxy)ethyl]benzenesulphonamide C
6
H
5
SO
2
NH(CH
2
)
2
OCOC
6
H
4
CH
3
(S)
BJ: N-(2-hydroxyethyl)-p-methoxybenzenesulphonamide CH
3
OC
6
H
4
SO
2
NH(CH
2
)
2
OH (S)
BM: N-(2-hydroxypropyl)benzenesulphonamide C
6
H
5
SO
2
NHCH
2
CH(CH
3
)OH (L)
The advantages introduced by the aromatic sulphonamides of formula (I) in the plasticization of the semi-crystalline polymers are many. Among these, mention may be made of:
the high thermal stability of the sulphonamides makes it possible to incorporate them in polymers at high temperature without them substantially evaporating, which prevents losses of the product and atmospheric pollution; they do not decompose at high temperature, which prevents unacceptable colouring of the polymer and allows them to act as plasticizer since they remain present intact in the polymer. It is consequently possible henc

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