Functionalized polymers

Details Functionalized polymers Functionalized polymers

1998-09-14

2001-03-06

Lipman, Bernard (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...

C525S359200, C525S386000

Reexamination Certificate

active

06197892

ABSTRACT:

The present invention relates to a functionalized polymer of the formula
A—Z—X
where
A is a block of vinylaromatic monomers of 8 to 20, preferably 8 to 12, carbon atoms,
Z is a basic building block comprising a compound having sterically hindering groups and
X is a functionalized basic building block,
wherein the degree of functionalization of the polymer is at least 65%, preferably greater than 85%, particularly preferably at least 90%.
The preparation of terminal anhydride-functionalized polystyrene is described in Park, J. W., Barlow, and Paul “Terminal Anhydride Functionalization of Polystyrene”, J. Polym. Sci., Part A, Polymer Chemistry, 29 (1993), 1329-1338. Styrene is subjected to anionic polymerization, and the polystyryllithium formed is coupled directly with trimellitic anhydride chloride (TMAC) at the end of the anionic polymerization of styrene. The degree of functionalization of the polymer is not more than 61% in this direct functionalization. Polystyrenes functionalized with TMAC were also obtained by reacting hydroxyl-terminated polystyrene and TMAC. In this reaction for indirect functionalization, degrees of functionalization of up to 85% are achieved. However, the feasibility of this process depends on the availability of hydroxyl-terminated polymer, which is obtainable by anionic polymerization and subsequent reaction with ethylene oxide at the end of the polymerization (R. P. Quirk and J.-J. Ma, J. Polym. Sci. Polym. Chem. Ed. 26 (1988) 2031). Polystyrenes functionalized in this manner to can be used for the in situ formation of block copolymers in polymer blends for compatibilization of the polymer blend components.
The indirect functionalization has the disadvantage that ethylene oxide, which is toxicologically unsafe, must be used in the process.
Reinforced blends of PPE and high impact polystyrene, which are used as molding materials in many areas of industry, are known per se. In many applications, high tensile strength and flowability of the material are decisive.
DE 31 18 629 A1 discloses molding materials of polyphenylene ethers and toughened styrene polymers, which molding materials contain a polyorganosiloxane as a further component for imparting good flowability to the molding material. If these molding materials are reinforced, the rigidity of the reinforced molding material is not sufficiently high for all applications.
EP-B1 0 214 400 describes resin compositions of polyphenylene ether resin and styrene resin, which additionally comprise a cyclopentadiene resin which contains a polar group, in order to improve the flowability of the resin composition. In this resin composition, too, the mechanical properties are unsatisfactory for many applications.
EP-A 0 319 833 describes reinforced thermoplastic molding materials which contain polyphenylene ether, a toughened styrene polymer and a further copolymer of styrene and tert-butyl acrylate. The copolymer of styrene and tert-butyl acrylate serves for improving the mechanical properties, but the molding material has insufficient flowability.
It is an object of the present invention to provide a functionalized polymer of vinylaromatic monomers, the degree of functionalization being very high.
It is a further object of the present invention to provide a functionalized polymer of vinylaromatic monomers, the functionalization comprising no ethylene oxide basic building blocks.
It is a further object of the present invention to provide a process for the preparation of the functionalized polymers having a high degree of functionalization.
It is a further object of the present invention to provide a process for the preparation of the functionalized polymers having a high degree of functionalization, the use of the toxicologically unsafe ethylene oxide being dispensed with.
It is a further object of the present invention to provide reinforced thermoplastic molding materials which have high rigidity.
It is a further object of the present invention to provide reinforced thermoplastic molding materials which have very good tensile strength and at the same time flowability.
It is a further object of the present invention to provide thermoplastic molding materials which have high rigidity.
It is a further object of the present invention to provide thermoplastic molding materials which have great toughness or impact strength.
It is a further object of the present invention to provide a process for the preparation of these (reinforced) thermoplastic molding materials.
It is a further object of the present invention to provide moldings which have good rigidity and tensile strength.
We have found that these and further objects are achieved by a functionalized polymer as defined at the outset, by a process for its preparation, by (reinforced) thermoplastic molding materials, by processes for their preparation and by moldings as defined in the following. Preferred functionalized polymers are described as well in the following. Uses of the functionalized polymer and of the (reinforced) thermoplastic molding materials are described as well.
Functionalized Polymer (component (a))
The novel functionalized polymer is of the formula
A—Z—X
where
A is a block of vinylaromatic monomers of 8 to 20, preferably 8 to 12, carbon atoms,
Z is a basic building block comprising a compound having sterically hindering groups and
X is a functionalized basic building block,
wherein the degree of functionalization of the polymer is at least 65%, preferably greater than 85%, particularly preferably at least 90%.
According to the invention, the block A may be composed of one type or a plurality of types of vinylaromatic monomers, ie. may be homopolymer or copolymer.
A group of monomers which can be used according to the invention of A comprises styrene monomers. Styrene monomers may be unsubstituted or may be substituted by C
1
-C
12
-alkyl, preferably C
1
-C
14
-alkyl, on the aromatic nucleus or on the vinyl group. One or more straight-chain or branched alkyl radicals may be present as substituents. It is also possible for both the aromatic nucleus (benzene nucleus) and the vinyl group of the styrene monomers to be substituted.
Examples of styrenes which may be used according to the invention are styrene, &agr;-methylstyrene, p-methylstyrene, vinyltoluene and p-tert-butylstyrene, particularly preferably styrene.
Vinylaromatic monomers which contain a polynuclear aromatic radical bonded to the vinyl group may also be used. A suitable radical is, for example, naphthyl, which may be unsubstituted or alkyl-substituted as described above.
Z is a basic building block of a compound having sterically hindering (bulky) groups.
The compound is preferably a vinyl monomer which is substituted by sterically hindering groups at least on a carbon atom. Preferably, the vinyl group is substituted on a carbon atom by two aromatic radicals, preferably by vinyl radicals, which in turn may be substituted by the alkyl radicals described above for the monomers of the block A and further substituents. For example, alkyl of, preferably, 1-4 carbon atoms which in turn may be unsubstituted or substituted as described may be bonded to the other carbon atom of the vinyl group. According to an embodiment of the invention, the vinyl group substituted by sterically hindering groups has a total of 14-22 carbon atoms.
Thus, the basic building block Z is preferably diaryl alkylene of 14 to 22 carbon atoms, in particular 1,1-diarylethylene of the formula
where R is hydrogen or alkyl of 1 to 4 carbon atoms and Aryl is aryl of 6 to 10 carbon atoms, preferably phenyl.
X is a functionalized basic building block. According to an embodiment of the invention, the functional group(s) is/are such that they can form a strong bond, in particular a covalent bond, to a reinforcing agent, preferably a glass fiber or silanized glass fiber, in a molding material, as described below for the molding materials.
The functional group by means of which the covalent bond to the basic building block Z is achieved may be any desired functional group suitable for this purpose. It is preferably hydrox

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