Ion-conductive polymers with high ion conductivity and containing covalently bound ion complexes of one of formulas (IA-IC), wherein M.sup.+ is H.sup.+, Li.sup.+, Na.sup.+, or K.sup.+ ; m is an integer in the range 0-4; m' is an integer in the rage 0-7; m" is an integer in the range 0-8; and each R independently is halogen; --CO--O.sup.-, --CO--O.sup.-, M.sup.+, or --SO.sub.2 --O.sup.-, M.sup.+ ; cyano; nitro; C.sub.1-5 alkoxy; optionally substituted phenyl or phenoxy; --CONR.sup.5 R.sup.6 or --NR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 independently are hydrogen, C.sub.1-5 alkyl, optionally substituted phenyl, phenylcarbonyl, or C.sub.1-6 alkanoyl; --N(R.sup.6)--CO--R.sup.7 where R.sup.7 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, or optionally substituted phenyl; R.sup.7 --CO--, R.sup.7 --O--CO--, or R.sup.7 --O--CO--O--; cycloheptatrienyl; or one of the groups R is an ion complex of the type la, Ib, or Ic with the proviso that R cannot be a further ion complex of the type Ia, Ib, or Ic; or two groups R bound to two adjacent carbon together form a divalent aliphatic or alicyclic group with 3-8 carbon atoms and having at least 2 C--C double bonds, --CO--O--CO--, --CO--S--CO--, or --CO--N(R.sup.7)--CO--; and the free bond "a" either directly or through an intervening group, is bound to the polymer backbone.

FIELD OF THE INVENTION 
The present invention concerns ion-conductive polymers which are useful as 
electrolytes in electrochemical devices such as rechargeable batteries and 
fuel cells. 
BACKGROUND OF THE INVENTION 
The production, storage, and distribution of energy are among the main 
concerns of modern industry and society. Thus, the efficient exploitation 
of energy sources that generate electricity on an intermittent basis, e.g. 
solar energy, wind and wave power, require the availability of low-cost, 
high-efficiency electricity storage systems. Similarly, the increasingly 
widespread use of various portable electronic devices and appliances 
having fairly high power requirements, such as mobile telephones, portable 
music and video systems (compact cassette recorders/players, CD-players, 
video camcorders etc.), laptop computers and the like, has increased the 
number of rechargeable battery units in use by a significant factor. 
Finally, the desire to reduce urban air pollution has resulted in the 
development of electric automobile systems that have highlighted the 
shortcomings of existing battery systems with respect to price, 
power-to-weight ratio, and/or environmental concerns due to use of 
environmentally problematic materials such as heavy metals. 
There have been a number of attempts at using ion-conductive polymers as 
electrolytes in batteries, i.a. in connection with the use of alkali 
metals as electrode material combined with the corresponding alkali metal 
cation as the charge carrier through the electrolyte. Lithium in 
particular is attractive for high-density batteries due to its low 
specific density, high standard potential and high melting point. Such 
attempts include the use of alkali metal salts such as LiClO.sub.4 
solvated in a poly(alkylene oxide) matrix and the use of covalently bound 
ion-polymer complexes such as phenolate derivatives covalently bound to a 
poly(methyl hydrosiloxane) backbone. 
In the case of solvated salt, the stability of the alkali metal electrode 
is believed to depend on the formation of a passivation layer which is due 
to an irreversible chemical reaction between the counter anion and the 
alkali metal electrode. However, despite relatively high ion 
conductivities of such electrolytes, the passivation phenomenon seriously 
limits the lifetime of the battery. 
The passivation problem may be solved partially by covalently binding the 
anions to the backbone as has been done with the use of phenolates. 
However, although the anions are immobilized on the polymer matrix, these 
attempts have not resulted in electrolytes with ion conductivities of 
practically useful magnitude due to low dissociation constant of the 
lithium/phenolate ion pair and/or to the use of systems of inferior 
ion-solvating properties. 
Consequently, there is a need for ion-conductive polymers that are stable 
in contact with the electrode materials and have ion conductivities of a 
magnitude that makes them practically applicable as electrolytes for 
inclusion into batteries or fuel cells. 
SUMMARY OF THE INVENTION 
It has now been found that surprisingly high ion conductivities can be 
obtained by means of polymers containing ion complexes comprising 
covalently bound carbocyclic anionic groups, the anion groups being 
aromatic and having been rendered aromatic as a result of the anion 
formation through the removal of at least one H.sup.+ ion. The aromatic, 
carbocyclic anionic groups may be substituted by various groups including 
electron-withdrawing groups. 
In particular, the invention concerns an ion-conductive polymer containing 
covalently bound ion complexes of one of the formulas Ia-Ic 
##STR1## 
wherein M.sup.+ is H.sup.+, Li.sup.+, Na.sup.+, or K.sup.+ ; 
m is an integer in the range 0-4; 
m' is an integer in the range 0-7; 
m" is an integer in the range 0-8; and 
each group R independently is 
halogen; 
a group --CO--O.sup.-, --CO--O.sup.-,M.sup.+, or --SO.sub.2 
--O.sup.-,M.sup.+ wherein M.sup.+ is as defined above; 
cyano; 
nitro; 
C.sub.1-5 alkoxy; 
optionally substituted phenyl; 
optionally substituted phenoxy; 
a group --CONR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 independently are 
hydrogen, C.sub.1-5 alkyl, optionally substituted phenyl, phenylcarbonyl, 
or C.sub.1-6 alkanoyl; 
a group --NR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 independently are as 
defined above; 
a group --N(R.sup.5)--CO--R.sup.7 where R.sup.5 is as defined above, and 
R.sup.7 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 
alkynyl, or optionally substituted phenyl; 
a group R.sup.7 --CO--, a group R.sup.7 --O--CO--, a group R.sup.7 
--CO--O--, or a group R.sup.7 --O--CO--O-- where R.sup.7 is as defined 
above; cycloheptatrienyl; or 
one of the groups R is a ion complex Ia', Ib', or Ic' 
##STR2## 
wherein M.sup.+, m, m' and m" are as defined above, and R' has the same 
meanings as R defined above with the proviso that R' is not a ion complex 
Ia', Ib', or Ic'; 
or two groups R bound to two adjacent carbon atoms may together form 
a divalent aliphatic or alicyclic group with 3-8 carbon atoms and having at 
least 2 C--C double bonds; 
carbonyloxycarbonyl; 
carbonylthiocarbonyl; or 
a group --CO--N(R.sup.7)--CO-- where R.sup.7 is as defined above; 
and the free bond indicated by "a", either directly or through an 
intervening group, is bound to the polymer backbone. 
DETAILED DESCRIPTION OF THE INVENTION 
In the present context, the term "C.sub.1-5 alkyl" designates an alkyl 
moiety of 1-5 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, 
n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, or neopentyl. The term 
"C.sub.2-5 alkenyl" designates a monounsaturated hydrocarbyl group with 
2-5 carbon atoms, such as vinyl, allyl, 1-, 2-, or 3-propenyl, n-butenyl, 
sec-butenyl, iso-butenyl, n-pentenyl, sec-pentenyl, iso-pentenyl, The term 
"C.sub.2-5 alkynyl" designates a hydrocarbyl group with 2-5 carbon atoms 
and containing a triple bond, such as ethynyl, propynyl, n-butynyl, 
sec-butynyl, iso-butynyl, n-pentynyl, iso-pentynyl. The term "C.sub.1-5 
alkoxy" designates a C.sub.1-5 alkyl group as defined bound via an oxygen 
atom. The term "C.sub.1-6 alkanoyl" designates the acyl group derived from 
an alkanoic acid with 1-6 carbon atoms, such as formyl, acetyl, propionyl, 
butyryl, valeryl or hexanoyl. 
The term "halogen" designates fluoro, chloro, bromo, and iodo. 
The terms "optionally substituted phenyl" and "optionally substituted 
phenoxy" designate phenyl and phenoxy groups, respectively, which are 
unsubstituted or are substituted with, electron-withdrawing groups such as 
halogen, cyano, nitro, C.sub.1-5 alkoxy, a group --CONR.sup.5 R.sup.6 as 
defined above, a group --NR.sup.5 R.sup.6, as defined above, a group 
--N(R.sup.5)--CO--R.sup.7 as defined above, a group R.sup.7 --CO-- as 
defined above, a group R.sup.7 --O--CO-- as defined above, a group R.sup.7 
--CO--O-- as defined above, or a group R.sup.7 --O--CO--O-- as defined 
above. 
When two groups R bound are to two adjacent carbon atoms and together form 
a divalent aliphatic or alicyclic group, examples of such divalent groups 
are 1,3-propenylene, 1- or 2-buten-1,4-ylene, 1,3-butadien-1,4-ylene, 
1,3-pentadien-1,5-ylene, 5-methyl-1,3-pentadien-1,5-ylene, 
3-methyl-1,4-pentadien-1,5-ylene, 5-methylidene-1,3-pentadien-1,5-ylene, a 
group of the formula 
##STR3## 
and a group of the formula 
##STR4## 
where "a" indicates the free bonds. 
Specific, but not limiting examples of covalently bound ion complexes of 
the formulas Ia-Ic wherein two groups R bound to adjacent carbon atoms 
form the above defined groups are as follows: 
##STR5## 
where the free bond "a" shown in the formulas Ia-Ic may be in any of the 
possible positions. 
It is particularly preferred if the divalent group together with the cyclic 
nucleus in the formulas Ia-Ic forms a complete aromatic structure. 
Preferred examples of the covalently bound anion in the ion complexes of 
the formulas Ia-Ic are the cyclopentadienylide ion, the indenylide ion, 
and the 9-fluorenylide ion, in particular the cyclopentadienylide ion. 
Since the ion conductivity of an ion conductive polymer is unfavourably 
affected at temperatures below the glass transition temperature of the 
polymer due to crystallization of the ion-solvating polymer matrix, it is 
preferred that the glass transition temperature T.sub.g of the polymer of 
the invention is below 273.degree. K, more preferably below 263.degree.0K, 
most preferably below 253.degree. K, in particular below 243.degree. K, 
especially below 233.degree. K, such as below 223.degree. K. 
It has been established that a prerequisite for ion-conductivity is the 
presence of a suitably ion-solvating environment capable of solvating the 
ions, and in order to ensure such an environment, an ion solvating solvent 
may be incorporated into the electrolyte, e.g. tetrahydrofuran or 
propylene carbonate. 
However, it is known that the ion conductivity is also improved in the 
presence of poly(alkylene oxide) moieties in the polymer, and it is 
therefore preferred that such moieties are present in the polymer. It is 
particularly preferred that the polymer of the invention comprises 
sequences of the formula --(CH(Y)--CH.sub.2 --O).sub.n -- where Y is 
hydrogen or methyl, and n is an integer in the range of 2-30 depending on 
the polymeric: system selected, in particular in the range 3-10. Such 
sequences may be present either in the backbone of the polymer or in 
grafted side groups or in the intervening group. It has been shown that 
poly(alkylene oxide)s form canal-like structures in the polymeric matrix 
with the right dimensions for ion passage through the electrolyte. 
Depending on the precise composition of the poly(alkylene oxide) moieties 
in the polymer, they may affect the T.sub.g of the polymer due to the 
formation of crystalline domains amongst the poly(alkylene oxide) moieties 
present. While it has been found that such effects can be off-set by 
forming the electrolyte from a mixture of a polymer of the invention with 
for example polyisobutylene, it is also contemplated that the effect may 
be eliminated or substantially reduced by omitting forming the 
poly(alkylene oxide) moieties from identical units, thereby introducing an 
element of heterogeneity in the poly(alkylene oxide) moieties. 
Since it is chiefly the properties of the ion complexes of the formulas 
Ia-Ic which are responsible for the surprising ion conductivity properties 
of the polymers of the invention, the backbone in the polymers may in 
principle be any type of polymer which does not actually contain 
functionalities which would directly counteract the intended ion transport 
process such as groups or functionalities capable of binding strongly with 
M.sup.+. 
Examples, although by no means exhaustive, of general types of polymers 
which may form the basis for at least part of the backbone of the polymers 
of the invention are derivatives of polyolefines such as polyethylene, 
polypropylene or polyisobutylene; polymers of unsaturated acids such as 
acrylic acid, methacrylic acid, itaconic acid as well as derivatives of 
such acids such as esters, nitriles or amides, e.g. polyacrylic acid, 
poly(polyethoxymethylitaconate) (PEO(n)MI), poly(polyethyleneglycol 
methacrylate) (PGM), poly(hydroxyethyl acrylate); polyvinyl alcohol and 
derivatives thereof such as polyvinyl esters, e.g. polyvinyl acetate; 
derivatives of polyesters, typically formed from a diacid (e.g. adipic 
acid, terephthalic acid) and a dihydroxy compound (e.g. ethylene glycol, 
propylene glycol), such as poly(ethylene adipate); derivatives of 
polyamides, typically formed from a diacid (e.g. adipic acid, terephthalic 
acid) and a diamino compound (e.g. 1,3-diaminopropane, 1,4-diaminobutane, 
1,6-diaminohexane); polyalkyleneimines, both linear and branched, such as 
polyethyleneimine; substituted polyphosphazenes such as 
poly(bis-(methoxy-ethoxy-ethoxide)phosphazene; silicone polymer 
derivatives such as polysiloxane derivatives, e.g. derivatives of 
poly(methylhydrosiloxane). 
Furthermore, the polymer may be either crosslinked or non-crosslinked, and 
the crosslinking may have been brought about in any manner known in the 
art, e.g. through reaction of reactive groups on the backbone or a grafted 
side group thereon with crosslinking moieties having two or more 
functionalities; or through irradiation with ultraviolet light (optionally 
in the presence of UV-sensitive initiators such as benzophenone or 
benzoylperoxide), X-rays, gamma rays or electron beams (EB). 
The term "intervening group" is intended to mean any chemical moiety 
located between on the one hand the ion complexes of the formulas Ia-Ic 
defined above and on the other hand the polymer backbone. Since, as 
discussed above, it is the properties of the ion complexes of the formulas 
Ia-Ic which are chiefly responsible for ion conductivity properties of the 
polymers, it is clear that similar to the polymer backbone, the 
intervening group may in principle be any type of divalent chemical group 
or moiety which does not actually contain functionalities which would 
directly counteract the intended ion transport process. 
As examples, but by no means exhaustive, of intervening groups may be 
mentioned the following where the lefthand end of the various formulas is 
connected to the polymer backbone, and the righthand end is connected to 
the ion complex of the formulas Ia-Ic: 
--(CH.sub.2).sub.x -- where x is an integer from 1 to 10; 
--(CH.sub.2).sub.x' -(Phenyl)-, where x' is an integer from 1 to 10; 
--O--; 
--O-(Phenyl)-; 
--O--(CH.sub.2).sub.x" --, where x" is an integer from 1 to 10; 
--O--(CH.sub.2).sub.x' -(Phenyl)-, where x' is as defined above; and 
--(CH.sub.2).sub.y --O--CH.sub.2 --CH(OH)--CH.sub.2 --, where y is an 
integer from 1 to 10. 
In the above formulas, the group (Phenyl) designates a benzene ring, the 
substitution pattern of which may be 1,2-, 1,3-, or 1,4-, and the 
remaining positions on the ring are unsubstituted or may be substituted 
with any group capable of delocalizing the charge of the anion, e.g. 
cyano; nitro; C.sub.1-5 alkoxy; optionally substituted phenyl; optionally 
substituted phenoxy; a group --CONR.sup.5 R.sup.6 where R.sup.5 and 
R.sup.6 independently are hydrogen, C.sub.1-5 alkyl, optionally 
substituted phenyl, phenylcarbonyl, or C.sub.1-6 alkanoyl; a group 
--NR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 independently are as defined 
above; a group --N(R.sup.5)--CO--R.sup.7 where R.sup.5 is as defined 
above, and R.sup.7 is hydrogen, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, 
C.sub.2-5 alkynyl, or optionally substituted phenyl; a group R.sup.7 
--CO--, a group R.sup.7 --O--CO--, a group R.sup.7 --CO--O--, or a group 
R.sup.7 --O--CO--O-- where R.sup.7 is as defined above. 
In another embodiment of the polymer, sequences of the formula 
--(CH(Y)--CH.sub.2 --O).sub.n -- discussed above are comprised in the 
intervening groups between the ion complexes of the formulas Ia-Ic and the 
polymer backbone. 
The backbone of the polymer may be one which is derived from one of the 
following examples of polymers which, however, should not be construed as 
being limiting. In the examples, the basic structure of the polymer is 
given by showing the repeating units, but without showing where the 
location of the ion complex group of the formula Ia-Ic or the group 
containing the ion complex group. Thus, the backbone may be derived from 
polymer backbones of the following formulas II, III or IV 
##STR6## 
wherein X is halogen; R.sup.10 and R.sup.11 independently are hydrogen, 
alkyl with 1-3 carbon atoms, carboxy, carboxyalkyl with 1-3 carbon atoms, 
phenyl, a group --(OCH(Y)CH.sub.2).sub.n OH or a group 
--(OCH(Y)CH.sub.2).sub.n OR.sup.12 wherein Y is H or methyl, n is an 
integer in the range 2-30 and R.sup.12 is C.sub.1-3 alkyl; and y is an 
integer in the range from 3 to 10.sup.4, preferably from 3 to 10.sup.3, 
such as from 3 to 500. 
In the formula II, it will typically be in the position of the 
silicon-bound hydrogen that an intervening group or an ion complex or, 
alternatively, a grafted side group is inserted as a result of the 
reactivity of the hydrogen-silicon bond. Likewise, in the formula III it 
will typically be in the position of the halogen atom that an intervening 
group or an ion complex or, alternatively, a grafted side group is 
inserted as a result of the reactivity of the phosphorous-halogen bond. In 
the formula IV, it will typically be somewhere in R.sup.10 and/or R.sup.11 
that an intervening group or an ion complex or, alternatively, a grafted 
side group is inserted. 
The polymers of the invention may typically be prepared from suitably 
substituted monomers by known methods of polymerisation analogous to the 
manner in which the type of polymer, from which a polymer of the invention 
is derived, is usually prepared. However, in some cases such as 
poly(ethylene glycol) ethers and poly(methyl siloxane)s, it may be more 
practical to introduce the ion complex groups or moieties containing them 
or grafted side groups into already existing polymers having suitable 
functionalities in their structure. As an example of a type of reagent 
capable of introducing an intervening group or a grafted side groups may 
be mentioned poly(ethylene glycol) allyl methyl diether, the double bond 
of which is able to react with the polymethylhydrosiloxane of formula II 
replacing the hydrogen in a hydrosilylation reaction. 
When preparing the polymers of the invention from suitably modified 
monomers, the actual polymerization is typically performed in the same 
manner as known polymerizations relevant for the polymer in question, 
including the use of catalysts, coinitiators, solvents, proton traps, 
etc., cf. standard works in the polymer field such as M. P. Stevens, 
"Polymer Chemistry", Oxford University Press, 1990. Also, when the polymer 
contains poly(alkylene oxide) moieties, it may be advantageous to add an 
antioxidant, such as a sterically hindered phenol derivative, at the end 
of the polymerization reaction in order to prevent polymer degradation. 
Similarly, the monomers may be modified by standard organic chemical 
methods as exemplified by the following. 
Thus, the monomers for preparation of poly(vinyl ether)s (PVE) where the 
ether functions are of the poly(alkylene oxide) type, in particular the 
poly(ethylene oxide) type, may be for example synthesized from a mixture 
of ethyl vinyl ether and an appropriate poly(ethylene glycol)-monomethyl 
ether in the presence of mercuric acetate as a catalyst while heating the 
mixture at reflux temperature.sup.(15,16). Ethylene glycol allyl vinyl 
diether for preparing allylated PVE may be prepared from allyl alcohol and 
(2-chloroethyl) vinyl ether, in the presence of a strong base such as 
potassium hydroxide, optionally in the presence of an aprotic solvent such 
as dimethyl sulfoxide (DMSO) at elevated temperatures, typically between 
75.degree. C. and 85.degree. C..sup.(15). 
Monomers which are esters of unsaturated acids with an alcohol, such as 
poly(alkylene oxide)s or phenols, are typically prepared by acid catalyzed 
esterification of the unsaturated acid, e.g. itaconic acid, with an 
appropriate poly(alkylene oxide) or derivative thereof such as a suitable 
poly(ethylene glycol) or poly(ethylene glycol)-monomethyl ether, or with 
an appropriate phenol, or with a mixture of these, in the presence of e.g. 
p-toluene sulfonic acid catalyst in a solvent such as toluene at reflux 
temperature.sup.(17,18,19,20). 
When polymerizing the modified monomers, other unmodified, unsaturated 
co-monomers such as isobutylene or styrene may be included. 
For the preparation of polymers of the poly(methyl siloxane) type shown 
above, a suitable starting material may be a poly(methyl hydrosiloxane) 
which may then be reacted with a poly(ethylene glycol) allyl methyl 
diether or with allyl glycid ether or with styrene or a mixture of these 
in the presence of platinum catalyst.sup.(2). The poly(ethylene glycol) 
allyl methyl ether used as a starting material may be prepared by a 
reaction between allyl chloride and the sodium salt of an appropriate 
poly(ethylene glycol) monomethyl ether, optionally in an aprotic solvent 
such as tetrahydrofuran (THF) at temperatures between 40.degree. C. and 
70.degree. C..sup.(10). Similarly, poly(ethylene glycol) monomethyl ether 
and phenols can be grafted on to poly(methyl hydrosiloxane) in the 
presence of zinc octoate as a catalyst.sup.(2). These reactions may be 
carried out at room temperature, optionally in an aprotic solvent such as 
THF. However, the use of zinc octoate requires the extraction thereof from 
the resulting polymer by a modified Soxhlet process. 
A poly(alkylene oxide) matrix may also be introduced by mixing a polymer of 
the invention containing the ion complex of the formulas Ia-Ic (e.g. of 
the poly(methyl siloxane type) with 1) a copolymer of poly(ethylene 
glycol) methyl vinyl diether and ethylene glycol allyl vinyl diether; 2) 
poly(ethylene glycol)-crosslinked di-(poly(ethylene glycol) monomethyl 
ether)-polyphosphazene (DPP); or 3) poly(ethylene glycol)-crosslinked 
poly(di-poly(ethylene glycol) monomethyl ether) itaconate (PPI). 
Furthermore, any mixture of poly(ethylene glycol)-crosslinked DPP, 
poly(ethylene glycol)-crosslinked PPI and allylated PVE may serve the same 
purpose. In the case of allylated PVE, a crosslinking reaction occurs 
between the Si--H-bond in poly(methyl hydrosiloxane) and the double bonds 
in allylated PVE copolymer. 
DPP, poly(ethylene glycol)-crosslinked DPP or phenylated DPP may be 
prepared by means of the ring-opening reaction of dichlorophosphazene at 
temperatures in the range 240.degree.-260.degree. C., followed by reaction 
with the sodium salt of poly(ethylene glycol) monomethyl ether, 
poly(ethylene glycol), phenol, or a mixture thereof in the presence of 
tetra-n-butyl ammonium bromide. The reactions may optionally be carried 
out in an aprotic solvent such as THF, at temperatures between 60.degree. 
C. and 80.degree. C..sup.(7,8,9). 
Polymers of the PVE-type, the polyalkene (such as polyisobutylene (PIB)) 
type, the polystyrene type, or combinations thereof may be prepared by 
carbocationic polymerization methods. The relevant starting materials are, 
in a typical example of such a polymerization reaction, reacted in a 40/60 
(v/v) methylcyclohexane/dichloromethane solvent system with an initiating 
complex of titanium(IV)chloride and 
1,3-di-(2-methoxy-2-propyl)-5-tert-butylbenzene in the presence of a 
proton trap such as 2,6-di-tert-butylpyridine, and in another typical 
example polymerized in dichloromethane with BF.sub.3 Et.sub.2 O as the 
initiator at temperatures in the range from -70.degree. C. to -90.degree. 
C..sup.(12,13,14,15,16). 
Polymerization of unsaturated acid ester monomers such as itaconic acid 
diester monomers may be effected at temperatures in the range of 
50.degree.-60.degree. C. using .alpha.,.alpha.'-azobisisobutyronitril as a 
radical initiator.sup.(17,18,19,20). 
Polymers containing phenol- and/or styrene groups may furthermore be 
lithiated with alkyllithium (such as butyllithium (BuLi)) and then reacted 
with a suitable chemical compound for introducing a into the polymer 
precursor to the ion complex of the formulas Ia-Ic. One example of such a 
compound is 2-cyclopentene-1-on for introducing a cyclopentadienyl group 
onto the phenyl group. The ion complex is then formed by reacting the 
precursor group on the polymer with a metallating agent, for example an 
alkyllithium (such as methyllithium (MeLi) or BuLi) which then results in 
the formation of a lithium cyclopentadienylide group 
complex.sup.(3,4,5,6). 
The ion-complex may also be introduced into the polymer either by adding a 
metal salt of the desired ion complex group to a polymer containing 
suitable functional groups with which to react; one example is the 
reaction between lithium cyclopentadienylide (LiCp) and an epoxy group on 
poly(methyl hydrosiloxane) carrying grafted allyl glycidyl ether groups. 
Another aspect of the invention is a battery or a proton exchange membrane 
fuel cell comprising an electrolyte comprising a polymer of the invention. 
When a fuel cell is desired, a polymer in which M.sup.+ is H.sup.+ is 
used, whereas when M.sup.+ is Li.sup.+, Na.sup.+, or K.sup.+, the polymer 
is used in a battery. The polymers of the invention may also be used in 
other electrochemical devices such as electrochromic displays, "smart 
window" displays, electrochemical sensors, ion exchange matrixes (e.g. in 
desalination plants), galvanic cells, supercapacitors, and hydrogen 
concentration units. 
A battery or a fuel cell according to the invention may be designed in a 
manner known per se to the person skilled in the art, e.g. as described in 
"Polymer Electrolyte Reviews" vol. 1 and 2, Ed. J. R. MacCallum & C. A. 
Vincent, Elsevier Applied Science, 1989; "Electrochemical Science and 
Technology of Polymers" vol. 2, Ed. R. G. Linford, Elsevier Applied 
Science, 1990; Fiona M. Gray, "Solid Polymer Electrolytes", VCH 
Publishers, 1991; and A. J. Appleby & F. R. Foulkes, "Fuel Cell Handbook", 
Van Nostrand, New York, 1989. 
Thus, a typical example of a battery of the invention comprises a anode 
consisting of a sheet of nickel foil (serving as a current collector) 
laminated with a sheet of foil of the alkali metal in question, e.g. 
lithium foil with a thickness of 40-100 .mu.m. The electrolyte is then 
laminated onto the alkali metal foil, the thickness of the polymeric 
electrolyte typically being the range 20-100 .mu.m. 
Finally, a cathode is laminated onto the surface of the electrolyte 
opposite the anode laminate. In order to be able to accommodate the alkali 
metal atoms resulting from the transport across the electrolyte of alkali 
metal ions, the cathode typically comprises a intercalating material, such 
as TiS.sub.2, V.sub.2 O.sub.5, V.sub.6 O.sub.13, MnO.sub.2, CoO.sub.2, the 
alkali metal atoms resulting from the ion transport intercalating in 
vacant positions in the crystal lattice of the cathode material when the 
ion accepts an electron. In order to provide the cathode with sufficient 
electrical conductivity, the intercalation material is typically mixed 
with particles of an electrically conductive, but electrochemically inert 
material such as carbon, e.g. graphite and coke, and further contains a 
portion of the ion-conductive polymer. 
The thickness of the entire laminate of anode, electrolyte, and cathode 
will depend on several factors but is typically up to a maximum of 2 mm. 
To provide batteries of cylindrical shape, the above laminate may simply 
be provided with suitable insulating layers and electrical connections and 
rolled or folded into the appropriate shape, e.g. a cylinder, and placed 
in a suitable casing. 
A typical example of a proton exchange membrane fuel cell according to the 
invention comprises a pair of teflon-coated carbon gas diffusion 
electrodes laminated onto both sides of a membrane of a proton-conductive 
polymer according to the invention which has been platinized on both 
sides, i.e. has been coated with very small platinum particles (cf. M. S. 
Wilson & S. Gottesfeld, (Electronics Research Group, Los Alamos National 
Laboratory, USA), Thin-film Catalyst Layers for Polymer Electrolyte Fuel 
Cells, Journal of Applied Electrochemistry, 22 (1992) 1-7). The whole 
system is enclosed in a casing, and hydrogen or a hydrogen-containing gas 
(or methane) is supplied to the anode side of the membrane, while oxygen 
or an oxygen-containing gas is supplied to the cathode side of the 
membrane. 
The manner in which the polymers of the invention are prepared as well as 
the procedures for producing single ion-conductive membranes containing an 
ion-polymer complex of the invention will be illustrated in more detail in 
the following, non-limiting examples. 
All the reactions were carried out in dry, O.sub.2 -free solvents and under 
a dry, inert atmosphere (N.sub.2 or Ar).

EXAMPLE 1 
The synthesis of: 
##STR7## 
A tetrahydrofuran solution (40 ml) of polymethyl hydrosiloxane (1.18 g, 
5.2.10.sup.-4 mole (PS 120)), polyethyleneglycol allyl methyl diether 
(2.12 g, 5.4.10.sup.-3 mole (MW=391)) and allyl glycidyl ether (0.45 g, 
3.9.10.sup.-3 mole) was placed in a 50 ml Erlenmeyer flask. The reaction 
was catalyzed by adding 7.5 .mu.l platinum-divinyltetramethyldisiloxan 
complex to the solution with a microsyringe.sup.(2). The mixture was 
stirred for 72 hours followed by addition of lithium cyclopentadienylide 
(0.22 g, 3.0.10.sup.-3 mole, corresponding to a EO/Li.sup.+ ratio of 
approximately 15. The solution was stirred for another 24 hours and cast 
on a glass plate. After the evaporation of the solvent the resulting 
polymer membrane (thickness approx. 0.25 mm) was dried at high vacuum. The 
conductivity of the complex was tested by means of a Solartron 1260 AC 
conductivity meter and was found to be 1.1.10.sup.-5 S cm.sup.-1 at room 
temperature. 
EXAMPLE 2 
The synthesis of: 
##STR8## 
A tetrahydrofuran solution (40 ml) of polymethyl hydrosiloxane (1.25 g, 
5.5.10.sup.-4 mole (PS 120)) and polyethyleneglycol 350 monomethyl ether 
(2.20 g, 6.3.10.sup.-3 mole) was placed in a 50 ml Erlenmeyer flask. The 
reaction was catalyzed by adding 25 mg of zinc octoate to the 
solution.sup.(2). The mixture was stirred for 24 hours followed by 
addition of allyl glycidyl ether (0.39 g, 3.4.10.sup.-3 mole) and 5 .mu.l 
platinum divinyl tetramethyldisiloxan complex for catalyzing.sup.(2). The 
mixture was stirred for 48 hours followed by addition of lithium 
cyclopentadienylide (0.16 g, 2,3.10.sup.-3 mole), corresponding to a 
EO/Li.sup.+ ratio of approximately 20. The solution was stirred for 
another 24 hours, filtered and then cast on a glass plate. After the 
evaporation of the solvent the resulting polymer membrane (thickness 
approx. 0.25 mm) was dried at high-vacuum. The conductivity of the complex 
was found to be 1.3.10.sup.-5 S cm.sup.-1 at room temperature. 
EXAMPLE 3 
The synthesis of: 
##STR9## 
A tetrahydrofuran solution (40 ml) of polymethyl hydrosiloxane (1.38 g, 
6.1.10.sup.-4 mole (PS 120)), polyethyleneglycol allyl methyl diether 
(2.92 g, 7.5.10.sup.-3 mole (MW=391)) and allyl glycidyl ether (0.37 g, 
3.2.10.sup.-3 mole) was placed in a 50 ml Erlenmeyer flask. The reaction 
was catalyzed by adding 7.5 .mu.l platinum divinyl tetramethyldisiloxan 
complex to the solution with a microsyringe.sup.(2). The mixture was 
stirred for 15 hours followed by addition of lithium indenylide (0.33 g, 
2.7.10.sup.-3 mole), corresponding to a EO/Li.sup.+ ratio of approximately 
20. The solution was stirred for another 8 hours, filtered and cast on a 
glass plate. After the evaporation of the solvent the resulting polymer 
membrane (thickness approx. 0.25 mm) was dried at high vacuum. The complex 
was purple and the conductivity was found to be 1.9.10.sup.-6 S cm.sup.-1 
at room temperature. 
EXAMPLE 4 
The synthesis of: 
##STR10## 
A tetrahydrofuran solution (40 ml) of polymethyl hydrosiloxane (1.35 g, 
5.9.10.sup.-4 mole (PS 120)), polyethyleneglycol allyl methyl diether 
(2.84 g, 7.3.10.sup.-3 mole (MW=391)) and allyl glycidyl ether (0.36 g, 
3.2.10.sup.-3 mole) was placed in a 50 ml Erlenmeyer flask. The reaction 
was catalyzed by adding 7.5 .mu.l platinum divinyl tetramethyldisiloxan 
complex.sup.(2). The mixture was stirred for 20 hours followed by addition 
of lithium fluorenylide (0.45 g, 2.6.10.sup.-3 mole (9-lithiumfluorene)), 
corresponding to a EO/Li.sup.+ ratio of approximately 20. The solution was 
stirred for another 7 hours, filtered and then cast on a glass plate. 
After evaporation of the solvent the resulting polymer was a viscosious 
purple liquid. 
Complexes made as described above, containing mixed salt mixtures of 
lithium cyclopentadienylide (example 1) and lithium fluorenylide, were 
solid complexes. The result of conductivity measurements of complexes 
containing 20-80 mole % (of total salt content) lithium fluorenylide 
(LiFl) is shown on the following table. The conductivity is obviously 
decreasing with increasing lithium fluorene content. 
______________________________________ 
% LiFl Conductivity (S cm.sup.-1) 
______________________________________ 
20 1.0 .multidot. 10.sup.-6 
60 7.4 .multidot. 10.sup.-7 
80 4.7 .multidot. 10.sup.-7 
______________________________________ 
EXAMPLE 5 
The synthesis of 
##STR11## 
9.5 g polymethyl hydrosiloxane (4.2.10.sup.-3 mole (PS 120)) and 20.1 g 
polyethyleneglycol allyl methyl diether (4.8.10.sup.-2 mole (MW=415)) was 
dissolved in approximately 70 ml tetrahydrofuran in a 100 ml volumetric 
flask. A reaction between the components was catalyzed by adding 25 .mu.l 
platinum divinyl tetramethyldisiloxan complex to the solution with a 
microsyringe.sup.(2). The mixture was stirred for 5 hours and then diluted 
to 100.0 ml. (PMHS/PEG-matrix solution) 
A polymer membrane with a EO/Li.sup.+ ratio of approximately 10 was 
prepared as follows: 15.0 ml of the PMHS/PEG-matrix solution was placed in 
a 50 ml Erlenmayer flask followed by addition of 5.7.10.sup.-3 mole of 
lithiumallyl-cyclopentadienylide dissolved in 7 ml of tetrahydrofuran. The 
solution was diluted to approximately 30 ml, stirred for 15 hours, diluted 
again to approximately 40 ml, filtered and cast on a glass plate. After 
evaporation of the solvent the resulting polymer membrane (thickness 
approx. 0.25 mm) was dried at high vacuum. The complex was brown and waxy. 
The conductivity was found to be 2.7.10.sup.-5 S cm.sup.-1 at room 
temperature. 
EXAMPLE 6 
The synthesis of: 
##STR12## 
23.7 g polymethyl hydrosiloxane (1.0.10.sup.-2 mole (PS 120)) and 50.1 g 
polyethyleneglycol allyl methyl diether (0.121 mole (MW=415)) was 
dissolved in approximately 150 ml tetrahydrofuran in a 250 ml volumetric 
flask. A reaction between the components was catalyzed by adding 100 .mu.l 
platinum divinyl tetramethyldisiloxan complex to the solution with a 
microsyringe.sup.(2). The mixture was stirred for 15 hours and then 
diluted to 250.0 ml. (PMHS/PEG-matrix solution) 
15.0 ml of the PMHS/PEG-matrix solution was placed in a 50 ml Erlenmeyer 
flask. The polymer was crosslinked by addition of 0.12 g 
polyethyleneglycol diallyl ether dissolved in 1.0 ml tetrahydrofuran 
(4.4.10.sup.-4 mole (MW=282)). After stirring for 4 hours, approximately 
3.9.10.sup.-3 mole of 2-(lithium cyclopentadienylide)ethyl-vinyl ether 
suspended in 8.3 ml tetrahydrofuran was added to the mixture, 
corresponding to a EO/Li.sup.+ ratio close to 15. The solution was 
diluted to approximately 40 ml, stirred for 15 hours, filtered and cast on 
a glass plate. After evaporation of the solvent the resulting polymer 
membrane (thickness approx. 0.25 mm) was dried at high vacuum. The complex 
was brown and the conductivity was found to be 3.3.10.sup.- 6 S cm.sup.-1 
at room temperature. 
EXAMPLE 7 
The synthesis of: 
##STR13## 
A 40 g sample of polymethyl hydrosiloxane (1.8.10.sup.-2 mole (PS 120)) was 
mixed with 70 g of polyethyleneglycol 350 monomethyl ether (0.20 mole) and 
10 g phenol (0.11 mole). The mixture was dissolved in 300 ml 
tetrahydrofuran and placed in a 0.5 l three-necked flask. The reaction was 
catalyzed by adding 100 mg of zinc octoate to the solution.sup.(2) and the 
mixture was stirred at room temperature for 72 hours. The polymer was 
lithiated by addition of 40 ml N,N,N',N'-tetramethylethylenediamine 
(TMEDA) and 20 ml of 10M butyllithium solution.sup.(3,4,6). The solution 
was refluxed overnight and then the solvent was removed a rotary 
evaporator. The resulting polymer (a yellow liquid) was washed three times 
with 100 ml of methylcyclohexane and dried at high vacuum (Yield 91.3 g 
(75%)). 
A 26 g sample of the lithiated polymer was dissolved in 100 ml 
tetrahydrofuran. While the mixture was stirred and cooled in an ice bath, 
2.5 ml of 2-cyclopentene-1-on was added.sup.(3). The solution immediately 
became orange, but then slowly turned deep red while being stirred for 100 
hours. The solvent was removed on a rotary evaporator whereby the polymer 
precipitated as beads. 
3 g of the beads were suspended in 75 ml of tetrahydrofuran by stirring for 
24 hours. Then they were treated with 0.25 ml of 10M butyllithium 
solution.sup.(3), corresponding to a EO/Li.sup.+ ratio of approximately 
20. The suspension was cast on a glass plate and after the evaporation of 
the solvent the resulting polymer membrane was dried at high vacuum. The 
conductivity of the complex was found to be 7.1.10.sup.-6 S cm.sup.-1 at 
room temperature. 
EXAMPLE 8 
The synthesis of: 
##STR14## 
A 40 g sample of polymethyl hydrosiloxane (1.8.10.sup.-2 mole (PS 120)) was 
mixed with 78 g of polyethyleneglycol allyl methyl diether (0.20 mole 
(MW=391)) and 11 g freshly distilled styrene (0.11 mole). The mixture was 
dissolved in 300 ml tetrahydrofuran and placed in an 0.5 1 three-necked 
flask. The reaction was catalyzed by adding 25 .mu.l platinum divinyl 
tetramethyldisiloxan complex to the solution.sup.(2), and the mixture was 
stirred at room temperature for 72 hours. The polymer was lithiated by 
addition of 40 ml TMEDA and 20 ml of 10M butyllithium 
solution.sup.(3,4,6). The solution was refluxed overnight and then the 
solvent was removed by a rotary evaporator. The resulting polymer (a 
orange liquid) was washed three times with 100 ml of methylcyclohexane and 
dried at high vacuum. (Yield 109.9 g (82%)). 
A 28 g sample of the lithiated polymer was dissolved in 100 ml 
tetrahydrofuran. While the mixture was stirred and cooled in an ice bath, 
2.5 ml of 2-cyclopentene-1-on was added.sup.(3). The solution immediately 
became red, but then slowly turned brown while being stirred for 100 
hours. The solvent was removed on a rotary evaporator whereby the polymer 
precipitated as beads. 
4 g of the beads were suspended in 75 ml of tetrahydrofuran by stirring for 
24 hours. Then they were treated with 0.30 ml of 10M butyllithium 
solution.sup.(3), corresponding to a EO/Li.sup.+ ratio of approximately 
20. The suspension was cast on a glass plate, and after the evaporation of 
the solvent the resulting polymer membrane was dried at high vacuum. The 
conductivity of the complex was found to be 9.1.10.sup.-6 S cm.sup.-1 at 
room temperature. 
EXAMPLE 9 
The synthesis of: 
##STR15## 
1.04 g (1.4.10.sup.-2 mole) lithium cyclopentadienylide was weighed in a 
100 ml volumetric flask and dissolved in approximately 50 ml 
tetrahydrofuran, followed by addition of 4.87 g (7.6.10.sup.-3 mole) 
poly(propylene oxide)diglycidyl ether. The mixture was stirred for 24 
hours and then diluted to 100.0 ml. (PPO solution) 
A solution containing 0.74 g of polymethyl hydrosiloxane (3.3.10.sup.-4 
mole (PS 120)), 2.70 g polyethyleneglycol allyl methyl diether 
(4.6.10.sup.-3 mole (Mw=591)) and allyl glycidyl ether (0.13 g, 
1.1.10.sup.-3 mole) in tetrahydrofuran was prepared in a 50 ml Erlenmeyer 
flask. A reaction between the existing carbon-carbon double bonds and the 
silicon-hydrogen bonds was catalyzed by adding 5.0 .mu.l platinum divinyl 
tetramethyldisiloxan complex to the solution with a microsyringe.sup.(2). 
The mixture was stirred for 15 hours followed by addition of 24 ml of the 
PPO solution, corresponding to a EO/Li.sup.+ ratio of approximately 20. 
The solution was stirred for another 8 hours and cast on a glass plate. 
After evaporation of the solvent the resulting polymer membrane (thickness 
approx. 0.25 mm) was dried at high vacuum. The complex was red and seemed 
to be separated into two phases. The conductivity of the dominant phase 
was found to be 5.4.10.sup.-6 S cm.sup.-1 at room temperature. 
EXAMPLE 10 
The synthesis of: 
##STR16## 
may be carried out in the following manner: A 12.5 g sample of 
phosphornitrile chloride (Cl.sub.9 N.sub.3 P.sub.3) is polymerized by a 
ring opening polymerization at 250.degree. C..sup.(7). The resulting 
polydichlorophosphazene is dissolved in 300 ml tetrahydrofuran and is 
added over a 0.5 hour period to a stirred suspension of 27.4 g of the 
sodium salt of triethyleneglycol monomethyl ether 
(polyoxyethylene-3-methylether (0.15 mole)) and 0.53 g of the disodium 
salt of polyethylene glycol 200 (2.1.10.sup.-3 mole) in 200 ml 
tetrahydrofuran in a 1.0 l three-necked flask. The reaction is carried out 
in the presence of tetra-n-butyl ammonium bromide to yield a fully 
substituted polymer.sup.(8). The mixture is refluxed for another 24 hours 
and then 7.7 g of the sodium salt of the phenol suspended in 100 ml 
tetrahydrofuran is added. The mixture is refluxed for another 24 hours and 
is then cooled to room temperature. The polymer is recovered by 
precipitation into heptane. 
The resulting polymer is then lithiated, grafted with cyclopentadiene and 
complexed in the same manner as described in examples 7 and 8. 
EXAMPLE 11 
The synthesis of: 
##STR17## 
may be carried out in the following manner: A polymer of the PVE-type, 
polyalkane, polystyrene or a combination thereof in a random copolymer or 
block-copolymer is prepared by living carbocationic polymerization with 
1,3-di-(2-methoxy-2-propyl)-5-tert-butylbenzene as an initiator, with 
titanium.sup.(IV) chloride as coinitiator. An ideal solvent system may be 
a 40:60 (v/v) mixture of methylcyclohexane and 
dichloromethane.sup.(12,13,14). The polymerization is carried out at 
-78.degree. C., in a cooling bath consisting of isopropyl alcohol mixed 
with dry ice. A proton trap such as 2,6-di-tert-butyl-pyridine and an 
electron donor such as DMA may optionally be applied. The resulting 
polymer is rinsed for homopolymers by soxhlet extraction with ethyl methyl 
ketone as an eluent. The apparent average molecular weight of the purified 
polymer may be measured by Gel Permeation Chromatography (GPC) with 
polyisobutylene, polystyrene and/or poly(ethylene glycol) standards, 
depending on the actual composition.sup.(12,13,14). 
A block-copolymer consisting of a middle-block of polyisobutylene and 
random end-blocks of polystyrene-co-poly-(ethylene glycol) methyl vinyl 
diether is prepared by living carbocationic polymerization in the said 
system, by preparing a solution of the initiator, proton trap, and 
isobutylene according to the art. The polymerization is turned on by 
adding a solution of the coinitiator to the system. After a while 
(typically 1-5 hours) the electron donor is added, followed by addition of 
a solution of poly(ethylene glycol) methyl vinyl diether and styrene. The 
polymerization is quenched with methanol after another 2-3 
hours.sup.(12,14). 
The polymer is the lithiated, grafted with cyclopentadiene and complexed in 
the same manner as described in examples 7 and 8. 
EXAMPLE 12 
The synthesis of: 
##STR18## 
may be carried out in the following manner: A random copolymer of 
poly(ethylene glycol) methyl vinyl diether and ethylene glycol allyl 
diether (allylated PVE).sup.(15,16) is prepared by living carbocationic 
polymerization, in the same system as described in example 11, by 
preparing a solution of the initiator, proton trap, and the said monomers 
according to the art. The polymerization is turned on by adding a solution 
of the coinitiator to the system. After typically 1-5 hours, the 
polymerization is quenched with methanol.sup.(12,13,14). 
The ion-conductivity may be gained by mixing the resulting copolymer with a 
polymer containing an ion complex of the invention, such as a poly(methyl 
hydrosiloxane) derivative (examples 1 and 2). In this case a crosslinking 
reaction occurs between the Si--H bond in the poly(methyl hydrosiloxane) 
and the double bond in the allylated PVE. 
EXAMPLE 13 
The synthesis of: 
##STR19## 
may be carried out in the following manner: Itaconate ester monomers may 
be prepared by acid catalyzed esterification of itaconic acid with the 
appropriate starting alcohol using p-toluene sulfonic acid as catalyst and 
toluene as solvent at reflux temperature. Alcohols such as polyethylene 
glycol 350 monomethyl ether, triethylene glycol monomethyl ether and 
phenol, may be used for the monomer synthesis. The corresponding 
itaconates are di-ethoxy(7,2)-methyl itaconate, di-ethoxy(3)-methyl 
itaconate and diphenyl itaconate. Unreacted alcohol is removed by washing 
the toluene solution several times with water. The required monomer may 
then be obtained by drying the toluene solution with magnesium sulphate, 
followed by azeotropic distillation.sup.(17,18,19,20). 
A mixture of di-ethoxy(7,2)-methyl itaconate, di-ethoxy(3)-methyl itaconate 
and diphenyl itaconate is placed in a 0.5 l flask. The monomers are 
polymerized using .alpha.,.alpha.'-azabisiso-butyronitrile as initiator by 
heating the system at 340 K for one week. The resulting polymer is 
dissolved in chloroform, precipitated from diethyl ether and dried for 24 
hours in vacuo.sup.(17,18,19,20). 
The polymer may then be lithiated, grafted with cyclopentadiene and 
complexed in the same manner as described in examples 7 and 8, with 
carefully purified and dried dichloromethane as solvent. 
In the case of y=0, ion-conductivity may be gained by mixing the resulting 
poly(poly(ethylene glycol) monomethyl ether) itaconate with a polymer 
containing an ion complex of the invention, such as a poly(methyl 
hydrosiloxane) derivative (example 1 and 2). 
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