Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1993-04-26
1994-08-16
Bleutge, John C.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
528174, 528125, 549 46, C08G 7523
Patent
active
053388216
DESCRIPTION:
BRIEF SUMMARY
This invention relates to novel aryl-ether-sulphone monomers and to polymers and copolymers, preferably aryl-ether-ketone-sulphone (AEKS) polymers and copolymers, containing units derived from these monomers.
Monomers for making AEKS polymers are often difficult and expensive to produce. One aspect of the present invention provides a monomer which can be made from readily available starting materials by a simple one-step process.
The aspect accordingly provides a compound of formula ##STR3## wherein each R independently is H, or C.sub.1 -C.sub.10 alkyl, and each R' independently is H. C.sub.1 -C.sub.10 alkyl, or Cl or F, having at least one reactive hydrogen on each of the two end benzo-rings. Preferably, all the R groups will be H. Also preferably, the ether --O-- groups will be in the para-position relative to the sulphone group and to the. furan oxygen. The most preferred monomer thus has the formula ##STR4##
These aryl furan-ether-sulphone-ether-furan (FESEF) monomers may be prepared, for example by a method comprising reacting a dibenzofuran compound of formula ##STR5## wherein M is an alkali metal, preferably Na, with a dihalide compound formula ##STR6## wherein X is halogen, preferably Cl, the molar ratio of the reacted dibenzofuran compound to the reacted dihalide compound being 2:1.
Appropriate starting materials, such as 2-hydroxydibenzofuran and 4,4'-dichlorodiphenylsulphone, are readily available in appropriately pure grades, and may for example be simply reacted by known procedures in the presence of alkali metal hydroxide (preferably sodium hydroxide) which produces the salt fore of the dibenzofuran for the above reaction.
The novel FESEF monomers may be used to produce polymers for example having a repeat unit of formula ##STR7## wherein R and R' are as defined above, and Ar is a mono- or poly-nuclear aromatic moiety in which two or more arylene groups if present may be linked by --CO--, --O--, --C(CH.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, or by a direct or fused-ring bond. Again it is preferred that all the groups are H and that the ether --O-- groups are in the para positions, the most preferred polymers thus having the repeat unit ##STR8##
These FESEFKetone polymer units may be made by condensing a FESEF monomer as hereinbefore defined with a diacid halide, for example terephthaloyl chloride or isophthaloyl chloride, so that the FESEFKetone unit is the product of condensing a compound of formula ##STR9## with a diacid halide compound of formula base controlling agent for the Lewis acid.
The invention includes random or block copolymers of such FESEFKetone repeat units together with aryletherketone repeat units, preferably present in the form of a polymer pre-block, for example as described in our copending British Patent Application (RK419), the disclosure of which is incorporated herein by reference. Preferably, the copolymers will comprise 30 to 60 mol % of the aryletherketone repeat units, although higher and lower proportions thereof are not excluded. Suitable aryletherketone repeat units are described, for example in our published International Application WO90/00573, the disclosure of which is incorporated herein by reference.
The invention also provides a method of making the FESEFKetone polymers hereinbefore described comprising ##STR10## or a monomer, oligomer or polymer pre-block having two terminal moieties of formula (TT) ##STR11## wherein each R independently is H, or C.sub.1 -C.sub.10 alkyl, and each R' independently is H, C.sub.1 -C.sub.10 alkyl, or Cl or F, having at least one reactive hydrogen on each of the two end benzo-rings, with a diacid halide component of formula terminal moiety (TT) as above and one terminal acid halide group --COX, in the presence of a Lewis acid, preferably also in the presence of a Lewis base controlling agent for the Lewis acid.
Polymers could alternatively be made from acid halide-terminated derivatives of the compound (A) or terminal moieties (TT) with an arylene moiety having two active terminal hydrogens.
These preferred methods may be c
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Bleutge John C.
Burkard Herbert G.
Chao Yuan
Lee Helen F.
Raychem Limited
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