Methods and agents for the extraction of cesium and strontium from nuclear waste
AssigneeCoremetals Research, Inc.
InventorsM. Frederick Hawthorne, Gary B. Dunks
Life of this patent
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Abstract
Methods and agents for extracting cesium and strontium ions from aqueous solutions, including aqueous fission product waste solutions, are disclosed using substituted metal dicarbollide and/or dicarbaextranide ions containing one or more chemical groups that increase solubility of the substituted metal dicarbollide or dicarbaextranide ions in non-nitrated, non-chlorinated solvents, or using metal dicarbollide or dicarbaextranide ion-substituted silicones.
Claims41
A substituted dicarbaextranide comprising a compound selected from the group consisting of:
- a) metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- 10 where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and;
- each R is independently selected from R.sub.1 and R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
The conjugate acid of a substituted dicarbaextranide, wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'" )(R')--O--!.sub.e ----!Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5 and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro- substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl,
- provided that at least one R must be R.sub.1.
An extraction agent comprising a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2--O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')---O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- W is oxygen or alkylene having from 2 to about 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
A method for selectively extracting cesium ions from an aqueous phase, comprising:
- forming an aqueous-nonaqueous liquid combination by contacting a pregnant aqueous phase containing cesium ions with a first nonaqueous phase comprising at least one extraction agent, wherein the extraction agent is a substituted metal dicarbaextranide;
- and
- separating the liquid combination into a stripped aqueous phase and a pregnant nonaqueous phase, wherein the pregnant nonaqueous phase contains cesium ions extracted from the pregnant aqueous phase;
- wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
A method for selectively extracting strontium ions from a substantially cesium-free aqueous solution, comprising:
- adding a polyethylene glycol or p-nonylphenyl-nonaethylene glycol to a pregnant aqueous phase containing strontium ions;
- forming an aqueous-nonaqueous liquid combination by contacting the pregnant aqueous phase with a first nonaqueous phase comprising at least one extraction agent, wherein the extraction agent is a substituted dicarbaextranide;
- and
- separating the liquid combination into a stripped aqueous phase and a pregnant nonaqueous phase, wherein the pregnant nonaqueous phase contains strontium ions extracted from the pregnant aqueous phase;
- wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub. ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms;
- and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5 and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0to 4, b, d, f, and h are 0to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl 1 of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10 and R', R", R'", b, c, and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
A method for selectively extracting cesium and strontium ions from an aqueous solution, comprising:
- forming a first aqueous-nonaqueous liquid combination by contacting a pregnant aqueous phase containing cesium and strontium ions with a first nonaqueous phase comprising at least one extraction agent, wherein the extraction agent is a substituted dicarbaextranide;
- separating the first liquid combination into a stripped aqueous phase and a pregnant nonaqueous phase, wherein the pregnant nonaqueous phase contains cesium ions extracted from the pregnant aqueous phase;
- modifying the stripped aqueous phase by adding a polyethylene glycol or p-nonylphenylnonaethylene glycol;
- forming a second aqueous-nonaqueous liquid combination by contacting the modified, stripped aqueous phase with a fresh nonaqueous phase comprising at least one extraction agent, wherein the extraction agent is a substituted dicarbaextranide;
- and
- separating the second liquid combination into a second stripped aqueous phase and a second pregnant nonaqueous phase, wherein the second pregnant nonaqueous phase contains strontium ions;
- wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10 and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
A method for extracting cesium ions from an aqueous solution, comprising contacting the cesium ions with at least one extraction agent comprising a substituted dicarbaextranide;
- wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3 ', --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
A method for extracting strontium ions from an aqueous solution, comprising contacting the strontium ions, in the presence of a polyethylene glycol or p-nonaphenylnonaethylene glycol, with at least one an extraction agent comprising a substituted dicarbaextranide;
- wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'-1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula;
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluorormethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to have 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro- substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro- substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
A semipermeable membrane, comprising a silicone elastomer or microporous polymer film wherein the elastomer or film comprises at least one substituted dicarbaextranide:
- wherein the substituted dicarbaextranide comprises:
- a) a metal dicarbaextranide ion of the formula:
- M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.a'+1).sub.2.sup.- ;
- or
- b) a metal dicarbaextranide ion-substituted organosiloxane of the formula:
- (R').sub.3 Si--O--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d ----Si(R'")(R')--O--!.sub.e ----Si(R').sub.2 --O--!.sub.f SiR'R"--O--!.sub.g Si(R').sub.2 --O--!.sub.h }.sub.i Si(R').sub.3 ;
- wherein
- M is a transition metal capable of forming a trivalent oxidation state;
- R' is methyl or trifluoromethyl;
- R" is phenyl or fluoro-substituted phenyl;
- R'" is a metal dicarbaextranide ion moiety of the formula:
- --W--M(B.sub.10 C.sub.2 H.sub.11-a' R.sub.1'+1 Z).sub.2.sup.- !
- where W is oxygen or alkylene having from 2 to about 10 carbon atoms, and each Z is independently selected from hydrogen, alkyl having from about 1 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 1 to about 10 carbon atoms;
- phenyl or substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- a' is 0 to 4;
- b, d, f, and h are 0 to 10;
- c and g are 0 or 1;
- and e and i are 1 to 10;
- and each R is independently selected from R.sub.1 or R.sub.2, where
- R.sub.1 is alkyl having from about 7 to about 10 carbon atoms;
- fluoro-substituted alkyl having from 2 to about 10 carbon atoms;
- substituted phenyl of the formula:
- --C.sub.6 H.sub.5-j Y.sub.j
- where j is 1 to 5, and Y is fluorine, phenyl or fluoro-substituted phenyl;
- or R.sub.1 is an organosiloxane of the formula:
- --W--{Si(R').sub.2 --O--!.sub.b SiR'R"--O--!.sub.c Si(R').sub.2 --O--!.sub.d }.sub.k E
- where
- E is --Si(R').sub.3, --Si(R').sub.2 (C.sub.6 H.sub.5) or R'", k is 1 to 10, and R', R", R'", b, c and d are as defined above;
- and
- R.sub.2 is selected from the group consisting of chlorine, bromine, methyl and trifluoromethyl;
- provided that at least one R must be R.sub.1.
Dependencies are inferred from the claim text.