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Electroactive, energy-storing, highly crosslinked, polysulfide-containing organic polymers and methods for making same

Assignee: Sion Power Corp
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Filing: 1997-12-19
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Granted: 2001-03-13
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Expires: 2017-12-19
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Abstract

Abstract The present invention pertains to electroactive, energy-storing, highly crosslinked organic polymers and copolymers with a carbocyclic repeat unit comprising a non-aromatic carbocycle with from 3 to 12 ring carbon atoms, wherein each repeat unit is covalently linked via divalent polysulfide linkages having the formula, —S m —, where m is the same or different at each occurrence and is an integer from 3 to 10. The present invention also pertains to methods of making such polymers and copolymers, which methods generally comprise reacting an alkali metal polysulfide with a halogen-substituted carbocyclic precursor.

Inventors

  • 👤 Alexander Gorkovenko
  • 👤 Terje A. Skotheim

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 12:31
CPC Classifications
H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01M; H01M4/00; H01M4/02; H01M4/36; H01M4/60; Y; Y02; Y02E; Y02E60/00; Y02E60/10

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 142 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, said method comprising the steps of: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogen substituted precursor comprises one or more materials selected from the group consisting of hexachlorocyclopentadiene, octachlorocyclopentadiene, 1,2,3,3,5,5-hexachloro-4-(dichloromethylene)-1-cyclopentene, and 1,2,3,4,5-pentachloro-5-(1,2,3,4,5-pentachlorocyclopenta-2,4-dieniyl)cyclopenta-1,3-diene; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 2
Independent Claim 142 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, said method comprising the steps of: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogen substituted precursor comprises one or more materials selected from the group consisting of hexachlorocyclopentadiene, octachlorocyclopentadiene, 1,2,3,3,5,5-hexachloro-4-(dichloromethylene)-1-cyclopentene, and 1,2,3,4,5-pentachloro-5-(1,2,3,4,5-pentachlorocyclopenta-2,4-dieniyl)cyclopenta-1,3-diene; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 3
Dependent Claim 23 words
The method of claim 1 , wherein the mixture of step (c) is heated at a temperature between 20° C. and 100° C.
Claim 4
Dependent Claim 12 words
The method of claim 1 , wherein said liquid medium comprises water.
Claim 5
Dependent Claim 13 words
The method of claim 1 , wherein said liquid medium consists of water.
Claim 6
Dependent Claim 29 words
The method of claim 1 , said method further comprising after step (d), one or more steps of: (e) purifying the polymer after isolation; and, (f) drying the polymer.
Claim 7
Independent Claim 224 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises a plurality of non-aromatic carbocyclic repeat units which are covalently linked via polysulfide linkages; each of said carbocyclic repeat units comprising a carbocycle having from 3 to 12 ring carbon atoms and from 3 to 22 covalent linkages to adjacent carbocyclic repeat units; and, each of said polysulfide linkages comprising a divalent polysulfide moiety having the formula, —(S m )—, wherein m is an integer from 3 to 10 and is the same or different at each occurrence; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens are selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 8
Independent Claim 224 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises a plurality of non-aromatic carbocyclic repeat units which are covalently linked via polysulfide linkages; each of said carbocyclic repeat units comprising a carbocycle having from 3 to 12 ring carbon atoms and from 3 to 22 covalent linkages to adjacent carbocyclic repeat units; and, each of said polysulfide linkages comprising a divalent polysulfide moiety having the formula, —(S m )—, wherein m is an integer from 3 to 10 and is the same or different at each occurrence; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens are selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 9
Independent Claim 235 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises polymeric segments of the formula wherein: Q denotes a non-aromatic carbocyclic repeat unit comprising a carbocycle having from 3 to 12 ring carbon atoms; S denotes a sulfur atom; m is the number of sulfur atoms in a given polysulfide linkage, is an integer from 3 to 10 and is the same or different at each occurrence; n denotes the number of crosslinking polysulfide linkages, is an integer from 1 to 20 and is the same or different at each occurrence; and, p is an integer greater than 1; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens arc selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 10
Independent Claim 235 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises polymeric segments of the formula wherein: Q denotes a non-aromatic carbocyclic repeat unit comprising a carbocycle having from 3 to 12 ring carbon atoms; S denotes a sulfur atom; m is the number of sulfur atoms in a given polysulfide linkage, is an integer from 3 to 10 and is the same or different at each occurrence; n denotes the number of crosslinking polysulfide linkages, is an integer from 1 to 20 and is the same or different at each occurrence; and, p is an integer greater than 1; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens arc selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 11
Independent Claim 225 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises two or more different non-aromatic carbocyclic repeat units which are covalently linked via polysulfide linkages; each of said carbocyclic repeat units comprising a carbocycle having from 3 to 12 ring carbon atoms and from 3 to 20 covalent linkages to adjacent carbocyclic repeat units; and, each of said polysulfide linkages comprising a divalent polysulfide moiety having the formula, —(S m )—, wherein m is an integer from 3 to 10 and is the same or different at each occurrence; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens are selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 12
Independent Claim 225 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises two or more different non-aromatic carbocyclic repeat units which are covalently linked via polysulfide linkages; each of said carbocyclic repeat units comprising a carbocycle having from 3 to 12 ring carbon atoms and from 3 to 20 covalent linkages to adjacent carbocyclic repeat units; and, each of said polysulfide linkages comprising a divalent polysulfide moiety having the formula, —(S m )—, wherein m is an integer from 3 to 10 and is the same or different at each occurrence; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens are selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 13
Independent Claim 230 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises non-aromatic carbocyclic repeat units and non-carbocyclic repeat units which are covalently linked via polysulfide linkages; each of said carbocyclic repeat units comprising a carbocycle having from 3 to 12 ring carbon atoms and from 3 to 20 covalent linkages to one or more adjacent carbocyclic or non-carbocyclic repeat units; and, each of said polysulfide linkages comprising a divalent polysulfide moiety having the formula —(S m )—, wherein m is an integer from 3 to 10 and is the same or different at each occurrence; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens are selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.
Claim 14
Independent Claim 230 words
A method for preparing an electroactive, energy-storing, highly crosslinked organic polymer, which polymer comprises non-aromatic carbocyclic repeat units and non-carbocyclic repeat units which are covalently linked via polysulfide linkages; each of said carbocyclic repeat units comprising a carbocycle having from 3 to 12 ring carbon atoms and from 3 to 20 covalent linkages to one or more adjacent carbocyclic or non-carbocyclic repeat units; and, each of said polysulfide linkages comprising a divalent polysulfide moiety having the formula —(S m )—, wherein m is an integer from 3 to 10 and is the same or different at each occurrence; the method comprising: (a) providing a solution or suspension of an alkali metal polysulfide of formula M 2 S m in a liquid medium, wherein M is an alkali metal selected from the group consisting of lithium, sodium, potassium, and cesium, and m is an integer from 3 to 10; (b) adding to the solution or suspension of step (a) a halogen substituted precursor comprising a non-aromatic carbocycle, wherein said halogens are selected from the group consisting of: chlorine, bromine and iodine, and said carbocycle comprises from 3 to 12 ring carbon atoms; (c) stirring and heating said mixture of step (b), thereby reacting said alkali metal polysulfide with said halogen substituted carbocyclic compound to form an electroactive, energy-storing, highly crosslinked organic polymer; and, (d) separating the polymer from the reaction medium.

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