Pyrrolidinone-containing compatibilizers

Details Pyrrolidinone-containing compatibilizers Pyrrolidinone-containing compatibilizers

1997-08-14

2002-04-09

Zitomer, Fred (Department: 1713)

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

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S256000, C525S257000, C525S259000, C525S279000, C525S266000, C525S293000, C525S298000, C525S300000, C525S286000, C525S328200, C525S329400, C525S333700, C525S375000, C525S383000

Reexamination Certificate

active

06369163

ABSTRACT:

The invention relates to the use of monomeric and polymeric N-pyrrolidinone-containing compounds as compatibilisers in plastic compositions, to the improved plastic compositions obtainable thereby as well as to novel polymeric N-pyrrolidinone-containing compounds.
Different plastic materials are usually not miscible, i.e. when two different plastic materials are processed, a macroscopic mixture is obtained which has insufficient mechanical properties. This is not only to be observed in mixtures of nonpolar plastics, e.g. polyethylene, and polar plastics, e.g. polyamide, but also even in the case of e.g. HDPE and LDPE. Such mixtures in the simplest case form a dispersion of the one polymer in the matrix of the other, i.e. a two phase system is obtained. Compatibilisers are polymers which preferably attach themselves to the interface between the polymers involved, or which penetrate into the polymers, thereby improving the adhesion between the polymers involved. The improved connection between matrix and dispersed phase enhances the mechanical properties. In addition, compatibilisers can improve the dispersion of the component and reduce the coagulation of the particles. In some cases, the separation of two-component systems or multicomponent systems can be completely inhibited resulting in a homogeneous blend of different plastic materials which has good mechanical properties.
Compatibilisers are used in virgin plastic compositions, but increasingly also in recyclates. Typical examples are polyethylene/polyamide-coextruded films (PE/PA films), which cannot be separated anymore in simple manner by physical methods. Further examples to be mentioned are PE/PET- and PE/PVC-coextruded films.
The known compatibilisers are mainly based on polymers of polar and nonpolar structure which can be prepared by conventional polymerisation reactions (K. Hausmann, Kunststoffe 1993, (83), 820; G. Obieglo and K. Romer, Kunststoffe, 1993, (83), 926; S. Fuzessery, Recycle 91, D 4.1-D 4.13; K. Hausmann, Kunststoffe 1995, (85), 446-451; S. Fuzessery, Recycle 95, Davos, 6-4.3-6-4.9; R. Mülhaupt et al., Kunststoffe 1994, (84), 1153-1158.
EP-A-0 602 008 discloses poly-N-vinylpyrrolidones as compatibilisers.
There is still a need to provide compatibilisers by means of which the properties of plastic compositions can be improved in simple manner.
This invention solves this task by using N-pyrrolidinone-containing compounds.
Accordingly, the invention relates to the use of 0.5 to 50% by weight of at least one monomeric or polymeric N-pyrrolidinone-containing compound as compatibiliser for plastic compositions, with the proviso that poly-N-vinylpyrrolidones are excluded.
Some of the N-pyrrolidinone-containing compounds used according to this invention are known from the state of the art, while those compounds which are N-pyrrolidinone-containing graft polymers are novel.
One advantage of the present invention is that the compatibility-improving effect is achieved already at low concentrations of monomeric or polymeric N-pyrrolidinone-containing compound.
Monomeric N-pyrrolidinone-containing compounds are preferably those of formula I
wherein
X is a direct bond or —OCH
2
CH
2
—, where the carbon atom is bound to the nitrogen,
R is
R
1
is hydrogen, C
1
-C
18
alkyl, C
6
-C
14
aryl, C
6
-C
13
aryl which is substituted by 1 to 3 phenyl or C
1
-C
18
alkyl groups; C
5
-C
7
cycloalkyl, or C
5
-C
7
cycloalkyl which is substituted by 1 to 3 C
1
-C
18
alkyl groups,
R
2
is hydrogen, C
1
-C
18
alkyl, C
6
-C
14
aryl, C
6
-C
13
aryl which is substituted by 1 to 3 phenyl or C
1
-C
18
alkyl groups; C
5
-C
7
cycloalkyl, or C
5
-C
7
cycloalkyl which is substituted by 1 to 3 C
1
-C
18
-alkyl groups, and
R
3
is hydrogen, C
1
-C
18
alkyl, C
6
-C
14
aryl, —COOH, C
6
-C
13
aryl which is substituted by 1 to 3 phenyl or C
1
-C
18
alkyl groups; C
5
-C
7
cycloalkyl, or C
5
-C
7
cycloalkyl which is substituted by 1 to 3 C
1
-C
18
alkyl groups.
Substituents of formula I defined as alkyl of up to 18 carbon atoms are typically radicals such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl or octadecyl as well as corresponding branched isomers.
Substituents of formula I defined as C
5
-C
7
cycloalkyl or C
5
-C
7
cycloalkyl which is substituted by 1 to 3 C
1
-C
18
alkyl groups are suitably radicals such as cyclopentyl, cyclohexyl, cycloheptyl, methylcyclohexyl, ethylcyclohexyl or ethylcycloheptyl.
Substituents of formula I defined as C
6
-C
14
aryl or C
6
-C
13
aryl which is substituted by 1 to 3 phenyl or C
1
-C
18
alkyl groups are suitably radicals such as phenyl, naphthyl or tert-butylphenyl.
R
1
and R
2
are preferably hydrogen.
R
3
is preferably —COOH; phenyl is unsubstituted or substituted by one C
1
-C
12
alkyl radical or phenyl radical.
Very particularly preferred compounds of formula I are those, wherein R
1
and R
2
are hydrogen and R
3
is —COOH; phenyl is unsubstituted by one C
1
-C
12
alkyl radical or phenyl radical.
The polymeric N-pyrrolidinone-containing compounds are derived from the above-described monomeric compounds, i.e. they contain at least one structural unit of monomeric compounds. The polymeric N-pyrrolidinone-containing compounds can be obtained by linking the monomeric compounds via the ethylenically unsaturated bond by a radically initiated graft polymerisation on organic polymers. In addition to their use as compatibilisers, these polymeric compounds constitute, as novel substances, a further object of the invention. It is not necessary that the monomer is chemically bonded to 100%. It suffices, for example, that only part of the monomer is chemically bonded (e.g. 10 to 40%) and that the remaining monomer is still in reactive form. A compatibiliser is then obtained which contains polymerically bonded groups as well as low-molecular components which only react when used in the blend and which become effective after reaction or as low-molecular compound.
The incorporation of the ethylenically unsaturated compounds of formula (I) in polymers is carried out by grafting on organic polymers. Organic polymers are mainly hydrocarbon polymers which can be saturated or unsaturated. Saturated hydrocarbons include the polyolefins, typically polyethylene, polypropylene, polybutene or polyisobutene. Unsaturated hydrocarbons include the diene polymers and their copolymers with olefines, typically poly-butadiene, polyisoprene, propylene/butadiene or ethylene/propylene/butadiene. It is preferred to graft on polyolefins, in particular on polyethylene and polypropylene.
Besides the cited and preferred polymers, further novel polymeric N-pyrrolidinone-containing compounds are derived from the polymers in the following list:
1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbomene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), branched low density polyethylene (BLDPE).
Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:
a) radical polymerisation (normally under high pressure and at elevated temperature).
b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either &pgr;- or &sgr;-coordinated. These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(II) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium.

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