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US4640748A
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Polyisothianaphtene, a new conducting polymer
Assignee: University of California
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Filing: 1985-05-22
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Granted: 1987-02-03
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Expires: 2005-05-22
Abstract
Abstract A polymer having an isothianaphthene structure represented by the formula (Ia) and/or Ib): <IMAGE> wherein R1 and R2 each represents a hydrogen atom or a hydrocarbon residue having 1 to 5 carbon atoms such as methyl, methoxy and thiomethyl, with the proviso that R1 and R2 may link together to form, along with the benzene ring, a fused ring which is naphthalene; X is sulfur, selenium or tellurium; Y- represents an anion of an electrolyte; z represents a number from 0.01 to 1 showing a ratio of the anion per mol of a monomer; and n represents a number of from 5 to 500 showing a degree of polymerization. An electrochromic display wherein a high molecular weight conductive membrane formed on a conductive transparent base is used as a display base and an opposing electrode is arranged thereunder via a liquid electrolyte, which is characterized in that said high molecular weight conductive membrane is a polymer having an isothianaphthene structure and capable of being reversibly oxidized or reduced.
Inventors
- 👤 Fred Wudl
- 👤 Masao Kobayashi
- 👤 Alan Heeger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:15
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/12; C08G61/122; C08G61/123; C09; C09K; C09K9/00; C09K9/02; G; G02; G02F; G02F1/00; G02F1/01; G02F1/15; G02F1/1514; G02F1/1516; G02F1/15165; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/127; H01M; H01M4/00; H01M4/02; H01M4/36; H01M4/60; Y; Y02; Y02E; Y02E60/00; Y02E60/10
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
129 words
A poly(isothianaphthene) polymer having a structural formula selected from the group consisting of (Ia) and (Ib) wherein: ##STR16## and wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen atoms and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that said R 1 and R 2 may link together to form, along with the benzene ring, a fused ring which is naphthalene; said X is selected from the group consisting of sulfur, selenium and tellurium; said Y - represents an anion of an electrolyte; said z represents a number from 0.01 to 1 showing a ratio of the anion per mol of a monomer; and said n represents a number of from 5 to 500 showing a degree of polymerization.
Claim 2
Dependent Claim
129 words
A poly(isothianaphthene) polymer having a structural formula selected from the group consisting of (Ia) and (Ib) wherein: ##STR16## and wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen atoms and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that said R 1 and R 2 may link together to form, along with the benzene ring, a fused ring which is naphthalene; said X is selected from the group consisting of sulfur, selenium and tellurium; said Y - represents an anion of an electrolyte; said z represents a number from 0.01 to 1 showing a ratio of the anion per mol of a monomer; and said n represents a number of from 5 to 500 showing a degree of polymerization.
Claim 3
Dependent Claim
11 words
The polymer of claim 1 having the structure of formula (Ia).
Claim 4
Dependent Claim
9 words
The polymer of claim 2 wherein X is sulfur.
Claim 5
Dependent Claim
14 words
The polymer of claim 3 wherein both R 1 and R 2 are hydrogen.
Claim 6
Dependent Claim
23 words
The polymer of claim 3 wherein R 1 and R 2 are selected independently from the group consisting of hydrogen, methyl and ethyl.
Claim 7
Dependent Claim
24 words
The polymer of claim 2 wherein R 1 and R 2 are selected independently from the group consisting of hydrogen, methyl, methoxy and thiomethyl.
Claim 8
Dependent Claim
9 words
The polymer of claim 6 wherein X is sulfur.
Claim 9
Dependent Claim
11 words
The polymer of claim 1 having the structure of formula (Ib).
Claim 10
Dependent Claim
9 words
The polymer of claim 8 wherein X is sulfur.
Claim 11
Dependent Claim
14 words
The polymer of claim 9 wherein R 1 and R 2 are both hydrogen.
Claim 12
Dependent Claim
23 words
The polymer of claim 9 wherein R 1 and R 2 are selected indpendently from the group consisting of hydrogen, methyl and ethyl.
Claim 13
Dependent Claim
24 words
The polymer of claim 8 wherein R 1 and R 2 are selected independently from the group consisting of hydrogen, methyl, methoxy and thiomethoxy.
Claim 14
Dependent Claim
9 words
The polymer of claim 12 wherein X is sulfur.
Claim 15
Dependent Claim
63 words
The polymer of claim 8 wherein Y - is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 16
Dependent Claim
62 words
The polymer of claim 9 wherein Y- is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 17
Dependent Claim
62 words
The polymer of claim 10 wherein Y- is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , Bf 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 18
Dependent Claim
62 words
The polymer of claim 11 wherein Y- is selected from the group consisting of Cl - , Br - , I - , ClO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 19
Dependent Claim
62 words
The polymer of claim 12 wherein Y- is selected from the group consisting of Cl - , Br - , I - , CIO 4 - , BF 4 - , PF 6 - , AsF 6 - , SbF 6 - , AlCl 4 - , AlBr 4 - , FeCl 4 - , and CF 3 SO 3 - .
Claim 20
Dependent Claim
13 words
The polymer of claim 8 wherein Y - is HSO 4 - .
Claim 21
Dependent Claim
13 words
The polymer of claim 23 wherein Y - is HSO 4 - .
Claim 22
Dependent Claim
13 words
The polymer of claim 10 wherein Y - is HSO 4 - .
Claim 23
Dependent Claim
13 words
The polymer of claim 11 wherein Y - is HSO 4 - .
Claim 24
Dependent Claim
13 words
The polymer of claim 12 wherein Y - is HSO 4 - .
Claim 25
Independent Claim
105 words
A method of preparing a poly(isothianaphthene) polymer by electrochemical polymerization comprising: (a) providing a monomer having the formula: ##STR17## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is napthalene; (b) disolving said monomer in an aprotic solvent containing electrolyte to provide a monomer solution, said electrolyte being ionic and a source of nucleophilic anions; and (c) electrochemically polymerizing said monomer solution to provide a poly(isothianaphthene).
Claim 26
Independent Claim
105 words
A method of preparing a poly(isothianaphthene) polymer by electrochemical polymerization comprising: (a) providing a monomer having the formula: ##STR17## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is napthalene; (b) disolving said monomer in an aprotic solvent containing electrolyte to provide a monomer solution, said electrolyte being ionic and a source of nucleophilic anions; and (c) electrochemically polymerizing said monomer solution to provide a poly(isothianaphthene).
Claim 27
Dependent Claim
10 words
The method of claim 24 wherein said monomer is 1,3-isothianaphthene.
Claim 28
Dependent Claim
19 words
The method of claim 24 wherein said polymerization forms said poly(isothianaphthene) into a membrane on a transparent conductive base.
Claim 29
Dependent Claim
19 words
The method of claim 25 wherein said polymerization forms said poly(isothianaphthene) into a membrane on a transparent conductive base.
Claim 30
Independent Claim
105 words
A method of preparing a poly(isothianaphthene) polymer of chemical polymerization comprising: (a) providing a monomer having the formula: ##STR18## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is napthalene; (b) polymerizing said monomer by contacting said monomer with a cationic polymerization catalyst whereby a poly(dihydroisothianaphthene) polymer is formed; and (c) dehydrogenating said poly(dihydroisothianaphthene) polymer by contact with an oxidizing agent to form a poly(isothianaphthene) polymer.
Claim 31
Independent Claim
105 words
A method of preparing a poly(isothianaphthene) polymer of chemical polymerization comprising: (a) providing a monomer having the formula: ##STR18## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is napthalene; (b) polymerizing said monomer by contacting said monomer with a cationic polymerization catalyst whereby a poly(dihydroisothianaphthene) polymer is formed; and (c) dehydrogenating said poly(dihydroisothianaphthene) polymer by contact with an oxidizing agent to form a poly(isothianaphthene) polymer.
Claim 32
Dependent Claim
10 words
The method of claim 28 wherein said monomer is 1,3-isothianaphthene.
Claim 33
Dependent Claim
13 words
The method of claim 28 wherein said monomer is polymerized in a solvent.
Claim 34
Dependent Claim
13 words
The method of claim 29 wherein said monomer is polymerized in a solvent.
Claim 35
Independent Claim
86 words
A method of preparing a poly(isothianaphthene) polymer comprising: (a) providing a monomer having the formula: ##STR19## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is napthalene; and (b) polymerizing said monomer by contacting said monomer with an oxidative polymerization catalyst whereby a poly(isothianaphthene) polymer is formed.
Claim 36
Independent Claim
86 words
A method of preparing a poly(isothianaphthene) polymer comprising: (a) providing a monomer having the formula: ##STR19## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is napthalene; and (b) polymerizing said monomer by contacting said monomer with an oxidative polymerization catalyst whereby a poly(isothianaphthene) polymer is formed.
Claim 37
Dependent Claim
14 words
The method of claim 32 wherein said oxidative polymerization catalyst is a Friedel-Crafts catalyst.
Claim 38
Dependent Claim
13 words
The method of claim 32 wherein said oxidative polymerization catalyst is sulfuric acid.
Claim 39
Dependent Claim
12 words
The method of claim 32 wherein said oxidative polymerization catalyst is 7,7,8,8-tetracyanoquinodimethane.
Claim 40
Dependent Claim
10 words
The method of claim 32 wherein said monomer is 1,3-isothianaphthene.
Claim 41
Dependent Claim
10 words
The method of claim 33 wherein said monomer is 1,3-isothianaphthene.
Claim 42
Dependent Claim
10 words
The method of claim 34 whrein said monomer is 1,3-isothianaphthene.
Claim 43
Dependent Claim
10 words
The method of claim 35 wherein said monomer is 1,3-isothianaphthene.
Claim 44
Independent Claim
87 words
A method of preparing a poly(isothianaphthene) polymer comprising: (a) providing a monomer having the formula: ##STR20## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is naphthalene; and (b) polymerizing said monomer by dissolving said monomer in a dehydrating and oxidizing solvent whereby a poly(isothianaphthene) polymer is formed.
Claim 45
Independent Claim
87 words
A method of preparing a poly(isothianaphthene) polymer comprising: (a) providing a monomer having the formula: ##STR20## wherein said R 1 and R 2 are selected independently from the group consisting of hydrogen and hydrocarbon residues having 1 to 5 carbon atoms, with the proviso that R 1 and R 2 may link together, along with the benzene ring, to form a fused ring which is naphthalene; and (b) polymerizing said monomer by dissolving said monomer in a dehydrating and oxidizing solvent whereby a poly(isothianaphthene) polymer is formed.
Claim 46
Dependent Claim
20 words
The method of claim 40 wherein said solvent is selected from the group consisting of sulfuric acid and polyphosphoric acid.
Claim 47
Dependent Claim
10 words
The method of claim 41 wherein said monomer is 1,3-dihydroisothianaphthene.
References Cited (Backward Citations)
US3574072A
Cited
US4461691A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-02-02 | 1990-08-04 | 1991-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-02 | 1994-08-04 | 1995-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-02 | 1998-08-04 | 1999-02-03 | $7700.00 | Window Closed / Lapsed |