US5520852A
Expired / Lapsed
US
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Processible electrically conducting polyaniline compositions
Assignee: Neste Oyj
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Filing: 1994-06-08
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Granted: 1996-05-28
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Expires: 2014-06-08
Abstract
Abstract Polymeric compositions are disclosed comprising protonated, electrically conducting polyaniline; cyclic organic compounds capable of forming ring-ring interactions with the six-membered rings of the polyaniline and hydrogen bonding with the NH groups of the polyaniline; and anionic surface active additives. According to the invention, no particular requirements are posed for the counter-ions of polyaniline, which allows for the use of non-functionilized counter-ions. The conducting polyaniline complexes of the invention are processible in the fluid-phase and exhibit significantly improved electrical properties.
Inventors
- 👤 Olli Ikkala
- 👤 Pentti Passiniemi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 13:44
CPC Classifications
H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/128; C; C08; C08G; C08G73/00; C08G73/02; C08G73/026; C08G73/0266; C08K; C08K5/00; C08K5/0008; C08L; C08L79/00; C08L79/02
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
562 words
A fluid-phase processible electrically conductive polymeric composition comprising an admixture of: (a) at least one electrically conductive polymer selected from the group consisting of electrically conducting optionally substituted protonated polyaniline, and a copolymer thereof; (b) at least one aromatic compound selected from the group consisting of substituted aromatic compounds of Formulas (IV) to (X) ##STR15## wherein: each R 1 represents H, --OH, --F, --Cl, --CH 3 or --OCH 3 , wherein one or more of the hydrogen atoms in the --CH 3 or --OCH 3 groups may be substituted by --F or --Cl; each R 2 is independently selected from the group consisting of --H, --OH, alkyl, alkenyl, alkoxy, alkanoyl, alkylthio, alkylthioalkyl, alkyl amide, alkylamidealkyl, alkyl hydroxy, alkyl carboxyl, having from 1 to about 20 carbon atoms; alkylaryl, arylalkyl, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, alkoxycarbonyl, wherein the alkyl or alkoxy moiety has from 0 to about 20 carbon atoms; or any two R 2 groups together may form an alkylene or alkenylene chain completing a 3 to 7-membered aromatic or alicyclic ring, which ring may optionally include one or more nitrogen, sulfur or oxygen heteroatoms; each Y 1 is independently selected from the group consisting of --OH, --COOH, --COO--Z, --CO--Z, --SO--Z, --SO 2 --Z, SO 2 NH--Z and --OCOO--Z, wherein Z represents an alkyl having 1 to about 20 carbon atoms; each Y 2 is --OH; each W 1 is independently selected from the group consisting of substituents of formulas X 1 , --C(C n H 2n+1 ) (C m H 2m+1 )--X 1 , wherein n and m are integers from 1 to about 20, --COO--X 1 , --CO--X 1 , --OCO--X 1 , --CH 2 --O--X 1 , --O--CH 2 --X 1 , --O--X 1 , --S--X 1 , --SO--X 2 , --SO 2 --X 1 , --SO 2 NH--X 1 , --OCOO--X 1 , cyclohexyl, and 5 or 6 -membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings; each W 2 is independently selected from the group consisting of substituents of formulas X 1 , --C(C n H 2n+1 ) (C m H 2m+1 )--X 1 , wherein n and m are integers from 1 to about 20, --COO--X 1 , --CO--X 1 , --OCO--X 1 , --O--X 1 , --S--X 1 , --SO--X 1 , --SO 2 --X 1 , --SO 2 NH--X 1 , --OCOO--X 1 , --COO--CH 2 --X 1 , --OCO--CH 2 --X 1 , --CH 2 --COO--X 1 , --CH 2 --OCO--X 1 , --O--C 2 H 4 --O--X 1 , cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings and each W 3 is independently selected from the group consisting of substituents of formulas X 1 , --C(C n H 2n+1 ) (C m H 2m+1 )--X 1 , wherein n and m are integers from 1 to about 20, --COO--X 1 , --CO--X 1 , --OCO--X 1 , --O--X 1 , --S--X 1 , --SO--X 1 , --SO 2 --X 1 , --OCOO--X 1 , --CH 2 --X 1 , cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon ring; and each X 1 is a group of formula (X) ##STR16## wherein R 1 and R 2 are as defined above; and (c) at least one surface active additive, wherein said substituted aromatic compound together with said surface active additive is capable of dissolving said electrically conductive polymer during processing.
Claim 2
Dependent Claim
562 words
A fluid-phase processible electrically conductive polymeric composition comprising an admixture of: (a) at least one electrically conductive polymer selected from the group consisting of electrically conducting optionally substituted protonated polyaniline, and a copolymer thereof; (b) at least one aromatic compound selected from the group consisting of substituted aromatic compounds of Formulas (IV) to (X) ##STR15## wherein: each R 1 represents H, --OH, --F, --Cl, --CH 3 or --OCH 3 , wherein one or more of the hydrogen atoms in the --CH 3 or --OCH 3 groups may be substituted by --F or --Cl; each R 2 is independently selected from the group consisting of --H, --OH, alkyl, alkenyl, alkoxy, alkanoyl, alkylthio, alkylthioalkyl, alkyl amide, alkylamidealkyl, alkyl hydroxy, alkyl carboxyl, having from 1 to about 20 carbon atoms; alkylaryl, arylalkyl, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, alkoxycarbonyl, wherein the alkyl or alkoxy moiety has from 0 to about 20 carbon atoms; or any two R 2 groups together may form an alkylene or alkenylene chain completing a 3 to 7-membered aromatic or alicyclic ring, which ring may optionally include one or more nitrogen, sulfur or oxygen heteroatoms; each Y 1 is independently selected from the group consisting of --OH, --COOH, --COO--Z, --CO--Z, --SO--Z, --SO 2 --Z, SO 2 NH--Z and --OCOO--Z, wherein Z represents an alkyl having 1 to about 20 carbon atoms; each Y 2 is --OH; each W 1 is independently selected from the group consisting of substituents of formulas X 1 , --C(C n H 2n+1 ) (C m H 2m+1 )--X 1 , wherein n and m are integers from 1 to about 20, --COO--X 1 , --CO--X 1 , --OCO--X 1 , --CH 2 --O--X 1 , --O--CH 2 --X 1 , --O--X 1 , --S--X 1 , --SO--X 2 , --SO 2 --X 1 , --SO 2 NH--X 1 , --OCOO--X 1 , cyclohexyl, and 5 or 6 -membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings; each W 2 is independently selected from the group consisting of substituents of formulas X 1 , --C(C n H 2n+1 ) (C m H 2m+1 )--X 1 , wherein n and m are integers from 1 to about 20, --COO--X 1 , --CO--X 1 , --OCO--X 1 , --O--X 1 , --S--X 1 , --SO--X 1 , --SO 2 --X 1 , --SO 2 NH--X 1 , --OCOO--X 1 , --COO--CH 2 --X 1 , --OCO--CH 2 --X 1 , --CH 2 --COO--X 1 , --CH 2 --OCO--X 1 , --O--C 2 H 4 --O--X 1 , cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings and each W 3 is independently selected from the group consisting of substituents of formulas X 1 , --C(C n H 2n+1 ) (C m H 2m+1 )--X 1 , wherein n and m are integers from 1 to about 20, --COO--X 1 , --CO--X 1 , --OCO--X 1 , --O--X 1 , --S--X 1 , --SO--X 1 , --SO 2 --X 1 , --OCOO--X 1 , --CH 2 --X 1 , cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon ring; and each X 1 is a group of formula (X) ##STR16## wherein R 1 and R 2 are as defined above; and (c) at least one surface active additive, wherein said substituted aromatic compound together with said surface active additive is capable of dissolving said electrically conductive polymer during processing.
Claim 3
Dependent Claim
30 words
A composition according to claim 1, wherein the surface active additive is an anionic surfactant selected from the group consisting of organic sulfonates, organic sulfates, organic phosphonates, and organic phosphates.
Claim 4
Dependent Claim
61 words
The composition according to claim 1, wherein, in Formulas (IV) to (X), at least one of the substituents R 1 , R 2 , Y 1 , Y 2 , W 1 , W 2 and W 3 is adjacent to at least one --OH substituent on a benzene ring and is selected from the group consisting of --H and --OH.
Claim 5
Dependent Claim
20 words
A composition according to claim 1, wherein the electrical conductivity of the composition is at least about 10 -9 S/cm.
Claim 6
Dependent Claim
20 words
A composition according to claim 1, wherein the electrical conductivity of the composition is at least about 10 -9 S/cm.
Claim 7
Dependent Claim
20 words
A composition according to claim 1, wherein the electrical conductivity of the composition is at least about 10 -3 S/cm.
Claim 8
Dependent Claim
104 words
A composition according to claim 1, wherein the aromatic compound is selected from the group consisting of alkyl substituted or unsubstituted hydroquinone, resorcinol, alkyl-substituted or unsubstituted catechol, alkyl gallates, dihydroxy acetophenones, bisphenol A, bisphenol F, dihydroxy benzophenone, p-hydroxy benzoic acid, m-hydroxy benzoic acid, and wherein the surface active additive is selected from the group consisting of Na + , Zn 2+ , Mg 2+ and Cu 2+ salts of alkyl benzene sulfonic acid, alkyl Na + , Zn 2+ , Mg n+ and Cu 2+ sulfates, and the Na + , Zn 2+ , Mg 2+ and Cu 2+ salts of naphthalene sulfonic acid.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-05-28 | 1999-11-27 | 2000-05-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-05-28 | 2003-11-27 | 2004-05-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-05-28 | 2007-11-27 | 2008-05-28 | $7700.00 | Window Closed / Lapsed |