Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Patent
1997-12-23
2000-06-20
Short, Patricia A.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
528388, 525535, C08G 7514, C08G 7518, C08G 7520
Patent
active
060779187
DESCRIPTION:
BRIEF SUMMARY
The invention relates to polyarylene sulfides, sulfoxides and sulfones which are substituted by triphenylphosphonium groups, a process for the preparation of these compounds and their use for the production of membranes.
Polymer-bound tetraalkylphosphonium salts are of considerable interest for the production of ion exchangers (U.S. Pat. No. 4,043,948), phase-transfer catalysts (Tomoi et al., J. Am. Chem. Soc. 103, 3821-3828 (1981)) and their use as biocides (Endo et al., J. Appl. Polymer Sci., 52, 641-447 (1994)).
Thermally more stable than tetraalkylphosphonium salts are the corresponding tetraarylphosphonium salts (Houben-Weyl Vol. 12/1, page 47). For applications in which high thermal stability is required, the use of tetraarylphosphonium salts is therefore preferable to the use of alkylphosphonium salts. For this purpose, the substrate polymer, too, must have sufficiently high thermal stability. This is the case with polyarylene sulfides and their oxidation products having sulfoxide groups and sulfonyl groups, for example poly(1,4-phenylene sulfide).
Tetraarylphosphonium salts are generally prepared from the corresponding aryl halide and triphenylphosphine, catalytically active transition metals being used (Houben Weyl Vol. E1, pages 518-525). Furthermore, dehydroaromatics, diaryliodonium salts or quinones may also be used as starting materials, in addition to aryl halides.
Tetraarylphosphonium tetraphenylborates bound to isobutylene polymers, rubber, neoprene or polyethylene are described in PCT/US 93/10027. Here, the corresponding phosphine is reacted with a halogenated polymer and an alkali metal borate in toluene or tetrahydrofuran.
The phosphonium salts known to date have the disadvantage that they are either chemically and thermally unstable, in particular when an aliphatic radical is attached to the phosphorus, or are insoluble in the conventional solvents. Furthermore, their preparation is in general possible only with considerable technical complexity and is therefore uneconomical.
It was therefore the object of the invention to provide soluble, thermally and chemically stable phosphonium ionomers which can be prepared in a simple and economical manner.
The present invention achieves this object and relates to polymeric phosphonium ionomers which, as random copolymers, are composed of the units (1) and (2) ##STR2## in which Ar-- is a phenylene radical, in particular a 1,3- or 1,4-phenylene radical, or a biphenylene, naphthylene or anthrylene radical or another divalent aromatic radical and may be different units within the polymer chain; --X-- is an --S--, --SO-- and/or --SO.sub.2 -- unit, units (1) and (2) in a polymer chain, is in the range from 3 to 2000,
The average proportion of units (2) in the polymer is in the range from 0 to 100 mol %, preferably in the range from 5 to 95 mol %.
The polymer may, if desired, be crosslinked via --X--, --Ar-- and/or --X--Ar--X units.
Ar is in particular a 1,4-phenylene or a 1,4- and a 1,3-phenylene radical.
In the phosphonium ionomer according to the invention, Z is, for example, at least one ion selected from the following group: CO.sub.3.sup.2-, CN.sup.-, OCN.sup.-, Hal.sup.- in particular Br.sup.-, Cl.sup.-, I.sup.-, OH.sup.-, NO.sub.3.sup.-, SO.sub.3.sup.2-, SO.sub.2.sup.2- or SCN.sup.-. In particular Z is Br.sup.-, Cl.sup.-, I.sup.- or OH.sup.-.
Some of the Ar units, preferably from 5 to 50%, may furthermore be substituted by bromine.
The average molecular weight of the triphenylphosphonium-polyarylene sulfide according to the invention is in the range from 4000 to 300,000 g/mol, in particular in the range from 30,000 to 200,000.
In a preferred embodiment, either all Ar units may carry at least one triphenylphosphonium group PPh.sub.3.sup.+ Z.sup.m-.sub.(1/m) as substituent or some Ar units carry two triphenylphosphonium groups PPh.sub.3.sup.+ Z.sup.m-.sub.(1/m) as a substituent, the remaining Ar units carrying only one or no PPh.sub.3.sup.+ Z.sup.m-.sub.(1/m) group as a substituent.
In a preferred embodiment, Ar is a 1,3- or 1,4-phenylene unit. In
Hoechst Aktiengesellschaft
Short Patricia A.
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