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US 8,137,590 B2Granted
Particles comprising zwitterionic structural elements
AssigneeWacker Chemie AG
InventorsChristoph Briehn, Peter Ball, Martina Baumann, Torsten Gottschalk-Gaudig, Manfred Hoelzl
Life of this patent
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Abstract
Solid particles bearing zwitterionic functional groups exhibit properties unlike other functionalized particles, and are particularly useful as proton-conductive fillers in membranes for fuel cells, where they increase physical properties as well as charge conducting properties. The particles are prepared by reacting functionalized particles with zwitterionic group-containing silanes or siloxanes.
Claims22
A composition of matter comprising solid functionalized particles which contain at least one structural element of the formulae [1] to [3],
- —NR2+—B-A− [1],
- ═NR+—B-A− [2],
- ≡N+—B-A− [3],
- and/or a protonated or deprotonated form thereof, wherein the structural elements of the formulae [1] to [3] are covalently bound to the particles by reacting (P) particles having an average primary particle size diameter less than 10 μm with silanes or siloxanes containing a structural element of the formula [1] to [3], and wherein
- A is a sulfonate radical —SO3, a carboxylate radical —C(O)O or a phosphonate radical —P(O)(OR7)O,
- B is (CR12)m, a substituted or unsubstituted alkyl radical interrupted by heteroatoms, or a substituted or unsubstituted aryl or heteroaryl radical,
- R and R7 are each hydrogen or a substituted or unsubstituted hydrocarbon radical,
- R1 is hydrogen, a halogen or a substituted or unsubstituted hydrocarbon radical, and
- m is 1, 2, 3, 4 or 5,
- with the proviso that the nitrogen atom in the formula [2] is an endocyclic nitrogen atom of an aliphatic heterocycle, and with the proviso that the nitrogen atom in the formula [3] is an endocyclic nitrogen atom of an aromatic heterocycle.
7 more elements
A process for producing a composition of matter comprising solid functionalized particles which contain at least one structural element of the formulae [1] to [3],
- —NR2+—B-A− [1],
- ═NR+—B-A− [2],
- ≡N+—B-A− [3],
- and/or a protonated or deprotonated form thereof, wherein the structural elements of the formulae [1] to [3] are covalently bound to the particles by reacting (P) particles with silanes or siloxanes containing a structural element of the formula [1] to [3], and wherein
- A is a sulfonate radical —SO3, a carboxylate radical —C(O)O or a phosphonate radical —P(O)(OR7)O,
- B is (CR12)m, a substituted or unsubstituted alkyl radical interrupted by heteroatoms, or a substituted or unsubstituted aryl or heteroaryl radical,
- R and R7 are each hydrogen or a substituted or unsubstituted hydrocarbon radical,
- R1 is hydrogen, a halogen or a substituted or unsubstituted hydrocarbon radical, and
- m is 1, 2, 3, 4 or 5,
- with the proviso that the nitrogen atom in the formula [2] is an endocyclic nitrogen atom of an aliphatic heterocycle, and with the proviso that the nitrogen atom in the formula [3] is an endocyclic nitrogen atom of an aromatic heterocycle,
- the process comprising reacting functionalizable particles with at least one silane or siloxane having at least one structural element of the formulae [1] to [3] to form functionalized particles.
8 more elements
A composition of matter comprising solid functionalized particles which contain at least one structural element of the formulae [1] to
- —NR2+—B-A− [1],
- ═NR+—B-A− [2],
- ≡N+—B-A− [3],
- and/or a protonated or deprotonated form thereof, wherein the structural elements of the formulae [1] to [3] are covalently bound to the particles by reacting (P) particles with silanes or siloxanes containing a structural element of the formula [1] to [3], and wherein
- A is a sulfonate radical —SO3, a carboxylate radical —C(O)O or a rhos shonate radical —P(O)(OR7)O,
- B is (CR12)m a substituted or unsubstituted alkyl radical interrupted by heteroatoms or a substituted or unsubstituted aryl or heteroaryl radical,
- R and R7 are each hydrogen or a substituted or unsubstituted hydrocarbon radical,
- R1 is hydrogen, a halogen or a substituted or unsubstituted hydrocarbon radical, and
- m is 1, 2, 3, 4 or 5,
- with the proviso that the nitrogen atom in the formula [2] is an endocyclic nitrogen atom of an aliphatic heterocycle, and with the proviso that the nitrogen atom in the formula [3] is an endocyclic nitrogen atom of an aromatic heterocycle further comprising a polymer matrix material in which the functionalized particles are dispersed, said composition in the form of a fuel cell membrane.
7 more elements
A composition of matter comprising solid functionalized particles which contain at least one structural element of the formulae [1] to [3],
- —NR2+—B-A− [1],
- ═NR+—B-A− [2],
- ≡N+—B-A− [3],
- and/or a protonated or deprotonated form thereof, wherein the functionalized particles are prepared by reacting particles (P) comprising primary particles with an average diameter less than 10 μm with silanes or siloxanes containing a structural element of the formula [1] to [3] and at least one silyl group which is reactive with surface functions of the particles (P), and wherein
- A is a sulfonate radical —SO3, a carboxylate radical —C(O)O or a phosphonate radical —P(O)(OR7)O,
- B is (CR12)m, a substituted or unsubstituted alkyl radical interrupted by heteroatoms, or a substituted or unsubstituted aryl or heteroaryl radical,
- R and R7 are each hydrogen or a substituted or unsubstituted hydrocarbon radical,
- R1 is hydrogen, a halogen or a substituted or unsubstituted hydrocarbon radical, and
- m is 1, 2, 3, 4 or 5,
- with the proviso that the nitrogen atom in the formula [2] is an endocyclic nitrogen atom of an aliphatic heterocycle, and with the proviso that the nitrogen atom in the formula [3] is an endocyclic nitrogen atom of an aromatic heterocycle, and
- wherein the structural elements of the formulae [1] to [3] are bound covalently to the solid particles through the silyl group.
8 more elements
Dependencies are inferred from the claim text.