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US4983322A Expired / Lapsed US ⏱️ 0.0 years remaining

Solution processible forms of electrically conductive polyaniline

Assignee: Zipperling Kessler GmbH and Co
•
Filing: 1987-01-12
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Granted: 1991-01-08
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Expires: 2007-01-12
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Abstract

Abstract This invention relates to solutions and plasticized compositions of electrically conductive substituted and unsubstituted polyanilines and to methods of forming such solutions or compositions and use of same to form conductive articles.

Inventors

  • 👤 Ronald L. Elsenbaumer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 11:18
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/026; C08G73/0266; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/128

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 232 words
A conductive material selected from the group consisting of solutions and plasticized compounds comprising one or more solvents selected from the group consisting of solvents having a dielectric constant equal to or greater than about 25 and a dipole moment equal to or greater than about 3.25; one or more dopant solutes selected from the group consisting of oxidizing dopants which form a charge transfer complex with the polyaniline having a conductivity equal to or greater than about 10 -3 ohm -1 cm -1 ; and a substituted or unsubstituted polyaniline having a molecular weight or greater than about 15,000 prepared by polymerizing an aniline of the Formula I: ##STR3## wherein: n is an integer from 0 to 4; m is an integer from 0 to 5 with proviso that the sum of n and m is 5; R is the same or different at each occurrence and is alkyl, alkenyl, alkoxy, cycloalkyl, cycloalkenyl, alkanoyl, alkylthio, aryloxy, alkylthioalkyl, alkylaryl, arylalkyl, alkylsulfinyl, alkoxyalkyl, alksulfonyl, aryl, arylthio, arylsulfinyl, alkoxycarbonyl, arylsulfonyl, carboxylic acid, halogen, cyano, or alkyl substituted with one or more sulfonic acid, carboxylic acid, halogen, nitro, cyano or epoxy moieties; or any two R substitutents taken together are an alkylene or alkenylene group completing a 3, 4, 5, 6 or 7 membered aromatic or alicyclic carbon ring, which ring may include one or more divalent heteroatoms of nitrogen, sulfur, sulfinyl, sulfonyl or oxygen.
Claim 2
Dependent Claim 232 words
A conductive material selected from the group consisting of solutions and plasticized compounds comprising one or more solvents selected from the group consisting of solvents having a dielectric constant equal to or greater than about 25 and a dipole moment equal to or greater than about 3.25; one or more dopant solutes selected from the group consisting of oxidizing dopants which form a charge transfer complex with the polyaniline having a conductivity equal to or greater than about 10 -3 ohm -1 cm -1 ; and a substituted or unsubstituted polyaniline having a molecular weight or greater than about 15,000 prepared by polymerizing an aniline of the Formula I: ##STR3## wherein: n is an integer from 0 to 4; m is an integer from 0 to 5 with proviso that the sum of n and m is 5; R is the same or different at each occurrence and is alkyl, alkenyl, alkoxy, cycloalkyl, cycloalkenyl, alkanoyl, alkylthio, aryloxy, alkylthioalkyl, alkylaryl, arylalkyl, alkylsulfinyl, alkoxyalkyl, alksulfonyl, aryl, arylthio, arylsulfinyl, alkoxycarbonyl, arylsulfonyl, carboxylic acid, halogen, cyano, or alkyl substituted with one or more sulfonic acid, carboxylic acid, halogen, nitro, cyano or epoxy moieties; or any two R substitutents taken together are an alkylene or alkenylene group completing a 3, 4, 5, 6 or 7 membered aromatic or alicyclic carbon ring, which ring may include one or more divalent heteroatoms of nitrogen, sulfur, sulfinyl, sulfonyl or oxygen.
Claim 3
Dependent Claim 180 words
A material according to claim 1 wherein said polyaniline is of the Formulas II to V: ##STR4## wherein: x is an integer equal to or greater than 1; y is an integer equal to or greater than 0, with the proviso that the sum of x and y is greater than 8; z is greater than about 1; n is an integer from 0 to 4; m is an integer from 0 to 5 with the proviso that the sum of n and m is 5; R is the same or different at each occurrence and is alkyl, alkenyl, alkyoxy, cycloalkyl, cycloalkenyl, alkanoyl, alkylthio, aryloxy, alkylthioalkyl, alkylaryl, arylakyl, alkylsulfinyl, alkoxyalkyl, alkylsulfonyl, aryl, arylthio, arylsulfinyl, alkoxycarbonyl, arylsulfonyl, carboxylic acid, halogen, cyano, or alkyl substituted with one or more sulfonic acid, carboxylic acid, halogen, nitro, cyano or epoxy moieties; or any two R substitutes taken together are an alkylene or alkenylene group completing a 3, 4, 5, 6 or 7 membered aromatic or alicyclic carbon ring, which ring may include one or more divalent heteroatoms of nitrogen, sulfur, sulfinyl, sulfonyl or oxygen.
Claim 4
Dependent Claim 16 words
A material according to claim 1 wherein m is equal to 5 and n is 0.
Claim 5
Dependent Claim 14 words
A material according to claim 1 wherein said polyaniline is derived from substituted anilines.
Claim 6
Dependent Claim 49 words
A material according to claim 2 wherein R is the same or different at each occurrence and is alkyl or alkoxy having from 1 to about 12 carbon atoms, cyano, halogen or alkyl having from 1 to about 12 carbon atoms substituted with carboxylic acid or sulfonic acid substituents.
Claim 7
Dependent Claim 51 words
A material according to claim 5 wherein R is the same or different at each occurrence and is alkyl or alkoxy having from 1 to about 4 carbon atoms, or substituted alkyl having from 1 to about 4 carbon atoms wherein permissible substituents are alkyl, carboxylic acid and sulfonic acid substituents.
Claim 8
Dependent Claim 27 words
A material according to claim 6 wherein R is the same or different at each occurrence and is alkyl having from 1 to about 4 carbon atoms.
Claim 9
Dependent Claim 12 words
A material according to claim 5 wherein n is 1 to 4.
Claim 10
Dependent Claim 12 words
A material according to claim 8 wherein n is 1 to 3.
Claim 11
Dependent Claim 10 words
A material according to claim 9 wherein n is 1.
Claim 12
Dependent Claim 182 words
A material according to claim 1 wherein said dopant is selected from the group consisting of AsF 5 , MoOCl 4 , MoCl 5 , PCl 5 , POCl 3 , PCl 3 , AlCl 3 , NOBF 4 , NOPF 6 , NOSbF 6 , NOAsF 6 , NOCH 3 CO 2 , NO 2 BF 4 , NO 2 PF 6 , NO 2 AsF 6 , NO 2 SbF 6 , NO 2 CF 3 SO 3 , HClO 4 , HNO 3 , H 2 SO 4 , p-toluenesulfonic acid, benzoyl peroxide, CF 3 SO 3 H, SO 3 , Br 2 , (FSO 3 ) 2 , ZnCl 2 , FSO 3 H, Fe(BF 4 ) 3 , FeBr 3 , Fe(CH 3 SO 3 ) 3 , Fe(ClO 4 ) 3 , FeCl 3 , Fe(OTs) 3 , Fe(CF 3 SO 3 ) 3 , LiClO 4 , LiBF 4 , LiAsF 6 , NaPF 6 , BuNClO 4 , Bu 4 NOTs, Bu 4 CF 3 SO 3 , LiCF 3 SO 3 and AgOTs.
Claim 13
Dependent Claim 68 words
A material according to claim 11 wherein said dopant is selected from the group consisting of MoOCl 4 , MoCl 5 , POCl 3 , PCl 5 , AlCl 3 , FeCl 3 , FeBr 3 , Fe(OTs) 3 , FE(CH 3 SO 3 ) 3 , Fe(CF 3 SO 3 ) 3 , ZnCl 2 , Fe(ClO 4 ) 3 , and Fe(BF 4 ) 3 .
Claim 14
Dependent Claim 46 words
A material according to claim 12 wherein said dopant is selected from the group consisting of FeCl 3 , FeBr 3 , Fe(ClO 4 ) 3 , AlCl 3 , ZnCl 2 , PCl 5 , PCl 3 , POCl 3 , and MoCl 5 .
Claim 15
Dependent Claim 31 words
A material according to claim 13 wherein said dopant is selected from the group consisting of FeCl 3 , FeBr 3 , ZnCl 2 , PCl 3 and MoCl 5 .
Claim 16
Dependent Claim 16 words
A material according to claim 2 wherein z is equal to or greater than about 5.
Claim 17
Dependent Claim 16 words
A material according to claim 15 wherein z is equal to or greater than about 10.
Claim 18
Dependent Claim 16 words
A material according to claim 16 wherein z is equal to or greater than about 15.
Claim 19
Dependent Claim 37 words
A material according to claim 2 wherein x is from 0 to about 8 and y is from 0 to about 8, with the proviso that the sum of x and y is at least about 8.
Claim 20
Dependent Claim 38 words
A material according to claim 18 wherein x is from about 1 to about 8 and y is from 0 to about 7, with the proviso that the sum of x and y is at least about 8.
Claim 21
Dependent Claim 38 words
A material according to claim 19 wherein x is from about 2 to about 8 and y is from 0 to about 6 with the proviso that the sum of x and y is at least about 8.
Claim 22
Dependent Claim 40 words
A material according to claim 1 wherein said solvent is selected from the group consisting of organic solvents having a dielectric constant equal to or greater than about 25 and a dipole moment equal to or greater than about 3.25.
Claim 23
Dependent Claim 18 words
A material according to claim 21 wherein said dielectric constant is equal to or greater than about 30.
Claim 24
Dependent Claim 30 words
A material according to claim 22 wherein said dielectric constant is equal to or greater than about 35, and said dipole moment is equal to or greater than about 34.
Claim 25
Dependent Claim 28 words
A material according to claim 1 wherein said solvent is selected from the group consisting of nitroalkanes, nitroaromatics, acetonitrile, propionitrile benzonitrile, dimethyl formamide, dimethyl sulfoxide and dimethyl acetamide.
Claim 26
Dependent Claim 24 words
A material according to claim 24 wherein said solvent is selected from the group consisting of nitroalkanes, nitroaromatics, dimethyl formamide, acetonitrile, proprionitrile and benzonitrile.
Claim 27
Dependent Claim 31 words
A material according to claim 1 wherein said solution contains sufficient dopant to provide a doped polyaniline having a conductivity of at least about 10 -5 ohm -1 cm -1 .
Claim 28
Dependent Claim 20 words
A material according to claim 26 wherein said conductivity is at least about 10 -4 ohm -1 cm -1 .
Claim 29
Dependent Claim 20 words
A material according to claim 27 wherein said conductivity is at least about 10 -3 ohm -1 cm -1 .
Claim 30
Dependent Claim 20 words
A material according to claim 28 wherein said conductivity is at least about 10 -2 ohm -1 cm -1 .
Claim 31
Dependent Claim 20 words
A material according to claim 29 wherein said conductivity is at least about 10 -1 ohm -1 cm -1 .
Claim 32
Dependent Claim 20 words
A material according to claim 29 wherein said conductivity is at least about 10 0 ohm -1 cm -1 .
Claim 33
Dependent Claim 20 words
A material according to claim 31 wherein said conductivity is at least about 10 1 ohm -1 cm -1 .
Claim 34
Dependent Claim 12 words
A material according to claim 1 wherein said material is a solution.
Claim 35
Dependent Claim 13 words
A material according to claim 1 wherein said material is a plasticized composition.
Claim 36
Dependent Claim 8 words
A composition comprising the material of claim 1.

References Cited (Backward Citations)

US3963498A Cited
US4025463A Cited
US4798685A Cited
US4806271A Cited
US4822638A Cited
US4851487A Cited
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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) 1994-01-07 1994-07-09 1995-01-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-01-07 1998-07-09 1999-01-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-01-07 2002-07-09 2003-01-08 $7700.00 Window Closed / Lapsed

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