Derivatized carbon monoxide copolymers

Details Derivatized carbon monoxide copolymers Derivatized carbon monoxide copolymers

2000-09-07

2001-10-23

Acquah, Samuel A. (Department: 1711)

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

Synthetic resins

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

C528S392000, C525S088000, C525S090000, C525S094000, C525S534000, C525S539000, C524S233000

Reexamination Certificate

active

06306979

ABSTRACT:

The present invention relates to derivatized carbon monoxide copolymers. The invention further relates to a process for the preparation of said carbon monoxide copolymers and their use for the preparation of graft copolymers. In addition, the invention relates to graft, copolymers, a process for the preparation of said copolymers and their use for the preparation of moldings, fibers, films and coatings and their use as a compatibilizer in polymer blends or as a coating component. Finally, the invention relates to the use of functionalized carbon monoxide copolymers for the preparation of derivatized carbon monoxide copolymers.
Carbon monoxide copolymers can now be prepared in the form of strictly alternating linear copolymers from carbon monoxide and &agr;-olefins such as ethene or propene using transition metal catalysts. Suitable catalyst systems are based on palladium complexes chelated with bidentate phosphine ligands (cf. EP-A-0 121 965 and J. Organomet. Chem. 417 (1991) 235). Conventional carbon monoxide/ethene or carbon monoxide/ethene/propene copolymers may usually be considered polymeric materials having a thermoplastic property spectrum. They exhibit good mechanical properties, e.g. with respect to impact resistance and abrasion, and good chemical resistance.
Apart from attempts to vary the polymer properties of carbon monoxide copolymers, such as the glass transition temperature, by the choice of the olefin component (cf. Jiang et al., J. Am. Chem. Soc. 117 (1995) 4455), it has also been attempted to obtain novel polymers by functionalizing the carbonyl group in the backbone of the chain, i.e. by polymer-analogous reactions.
For instance, Japanese patent applications JP-A 22 32 338 and JP-A 62 26 925 disclose the catalytic reduction of alternating carbon monoxide copolymers to form 1,4-polyalcohols. U.S. Pat. No. H1346 discloses the reaction with nitrogen-containing nucleophiles to give carbon monoxide/ethene/propene terpolymers having 2,5-pyrrole moieties. It is also possible to subject carbon monoxide copolymers to the Mannich reaction and to halogenate their methylene moiety (cf. U.S. Pat. No. 4,424,317 and U.S. Pat. No. 4,616,072).
Among the carbon monoxide copolymers known in the art, the carbon monoxide/ethene copolymer can be prepared relatively easily in large amounts, but the possible range of subsequent reactions is severely limited by its insolubility in all conventional solvents when it is used as a substrate for the abovementioned polymer-analogous reactions.
Furthermore, side reactions limit efficient derivatization of carbon monoxide copolymers. Examples of side reactions include subsequent free-radical reactions of the Norrish I and II type. Similarly, the addition of N-nucleophiles to the carbonyl group may also lead to a cleavage of the polymer backbone and thus to a reduction in the molecular weight of the copolymer.
It would therefore be desirable to be able to perform polymer-analogous reactions on carbon monoxide copolymers without side reactions and chain degradation.
It is an object of the present invention to provide carbon monoxide copolymers which may be derivatized without problems and without side reactions or reductions in molecular weight. It is another object of the invention to develop derivatized carbon monoxide copolymers which are suitable for further, subsequent reactions.
We have found that these objects are achieved by derivatized carbon monoxide copolymers obtainable by reacting, in an aprotic organic solvent, functionalized linear, strictly alternating carbon monoxide copolymers of carbon monoxide, at least one 1-alkene (A), where (A) is an aryl compound substituted by at least one terminal allyl or homoallyl moiety and by at least one hydroxyl or amino group, or an &agr;-olefinically unsaturated aliphatic alcohol, and, if desired, at least one C
2
-C
20
-1-alkene (B) with an organic compound (C) having at least one reactive electrophilic group.
Furthermore, we have found a process for the preparation of derivatized carbon monoxide copolymers and their use for the preparation of graft copolymers.
Furthermore, we have found graft copolymers, a process for the preparation of said copolymers and their use for the preparation of moldings, fibers, films and coatings and their use as a compatibilizer in polymer blends or as a coating component.
Finally, we have found the use of functionalized linear alternating carbon monoxide copolymers of carbon monoxide, at least one 1-alkene (A), where (A) is an aryl compound substituted by at least one terminal allyl or homoallyl moiety and by at least one hydroxyl or amino group, or an &agr;-olefinically unsaturated aliphatic alcohol, and, if desired, at least one C
2
-C
20
-1-alkene (B) for the preparation of derivatized carbon monoxide copolymers.
Suitable functionalized carbon monoxide copolymers which may be used for derivatization reactions in the present case are based on linear alternating carbon monoxide copolymers of carbon monoxide, at least one 1-alkene (A) which is an aryl compound substituted by at least one terminal allyl and/or homoallyl moiety and by at least one hydroxyl and/or amino group, or an &agr;-olefinically unsaturated aliphatic alcohol, and, if desired, at least one C
2
-C
20
-1-alkene (B).
1-Alkenes (A) used are preferably compounds of formulae (Ia) or (Ib)
where
X is OH or NH
2
,
Y is a compound of formula (II)
CH
2
═C(R
1
) (C(R
2
)
2
)
q
)—  (II),
where
R
1
is hydrogen, linear and branched C
1
-C
10
-alkyl, preferably C
1
-C
6
-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or t-butyl, especially methyl, C
3
-C
10
-cycloalkyl, preferably C
3
-C
6
-cycloalkyl, such as cyclopropyl or cyclohexyl, C
6
-C
10
-aryl, preferably C
6
-C
10
-aryl, especially phenyl, and
R
2
is independently at each appearance hydrogen, linear and branched C
1
-C
10
-alkyl, preferably C
1
-C
6
-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl or t-butyl, especially methyl, C
3
-C
10
-cycloalkyl, preferably C
3
-C
6
-cycloalkyl, such as cyclopropyl or cyclohexyl, C
6
-C
14
-aryl, preferably C
6
-C
10
-aryl, especially phenyl, or halogen, such as fluorine, chlorine, bromine, iodine, and
q is 1 or 2,
Q is independently at each appearance linear or branched C
1
-C
10
-alkyl, preferably C
1
-C
6
-alkyl, such as methyl, ethyl, n-propyl, Isopropyl, n-butyl, s-butyl or t-butyl, especially methyl, isopropyl or t-butyl, C
3
-C
10
-cycloalkyl, preferably C
3
-C
6
-cycloalkyl, such as cyclopropyl or cyclohexyl, C
6
-C
14
-aryl, preferably C
6
-C
10
-aryl, especially phenyl, aralkyl having from 1 to 6, preferably from 1 to 3, carbon atoms in the alkyl moiety and from 6 to 14, preferably from 6 to 10, carbon atoms in the aryl moiety, for example benzyl, or C
3
-C
30
-organosilyl, for example trimethyl-, triethyl-, triisopropyl-, triphenyl-, t-butyldiphenyl- or t-hexyldimethylsilyl, preferably trimethylsilyl,
where in the case of compounds of formula (Ia)
k, 1 are each an integer from 1 to 5 and
o is an integer from 0 to 4, subject to the proviso that
k+l+o≦6
and in the case of compounds of formula (Ib)
m, n are each an integer from 1 to 7 and
p is an integer from 0 to 6, subject to the proviso that
m+n+p≦8.
Particularly suitable compounds (A) have a terminal allyl moiety, i.e. are compounds of the formulae (Ia) and (Ib) where q=1. Of these olefinic monomers, the preferred monomers in turn have the terminal allyl moiety in a position ortho to a hydroxyl or amino group. Examples which may be mentioned are naphthyl compounds having an allyl moiety in the 1-position and one of the abovementioned polar groups in the 2-position or having an allyl moiety in the 2-position and a polar group in the 1- and/or 3-position and especially allylphenyl compounds having one or two polar groups in a position ortho to the allyl moiety.
Polar groups X that can be used are the hydroxyl group and the primary amino group. Suitable compounds are, for example, 2-allylphenol, 2-allyl-p-hydroquinone, 3-allyl-o-hydroquinone, 2-allylaniline, 2-allyl-4-aminoph

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