Processible electrically conducting polyaniline compositions
First Claim
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1. 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 R1 represents H, --OH, --F, --Cl, --CH3 or --OCH3, wherein one or more of the hydrogen atoms in the --CH3 or --OCH3 groups may be substituted by --F or --Cl;
each R2 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 R2 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 Y1 is independently selected from the group consisting of --OH, --COOH, --COO--Z, --CO--Z, --SO--Z, --SO2 --Z, SO2 NH--Z and --OCOO--Z, wherein Z represents an alkyl having 1 to about 20 carbon atoms;
each Y2 is --OH;
each W1 is independently selected from the group consisting of substituents of formulas X1, --C(Cn H2n+1) (Cm H2m+1)--X1, wherein n and m are integers from 1 to about 20, --COO--X1, --CO--X1, --OCO--X1, --CH2 --O--X1, --O--CH2 --X1, --O--X1, --S--X1, --SO--X2, --SO2 --X1, --SO2 NH--X1, --OCOO--X1, cyclohexyl, and 5 or 6 -membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings;
each W2 is independently selected from the group consisting of substituents of formulas X1, --C(Cn H2n+1) (Cm H2m+1)--X1, wherein n and m are integers from 1 to about 20, --COO--X1, --CO--X1, --OCO--X1, --O--X1, --S--X1, --SO--X1, --SO2 --X1, --SO2 NH--X1, --OCOO--X1, --COO--CH2 --X1, --OCO--CH2 --X1, --CH2 --COO--X1, --CH2 --OCO--X1, --O--C2 H4 --O--X1, cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings andeach W3 is independently selected from the group consisting of substituents of formulas X1, --C(Cn H2n+1) (Cm H2m+1)--X1, wherein n and m are integers from 1 to about 20, --COO--X1, --CO--X1, --OCO--X1, --O--X1, --S--X1, --SO--X1, --SO2 --X1, --OCOO--X1, --CH2 --X1, cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon ring; and
each X1 is a group of formula (X) ##STR16## wherein R1 and R2 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.
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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.
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Citations
7 Claims
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1. A fluid-phase processible electrically conductive polymeric composition comprising an admixture of:
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(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 R1 represents H, --OH, --F, --Cl, --CH3 or --OCH3, wherein one or more of the hydrogen atoms in the --CH3 or --OCH3 groups may be substituted by --F or --Cl;each R2 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 R2 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 Y1 is independently selected from the group consisting of --OH, --COOH, --COO--Z, --CO--Z, --SO--Z, --SO2 --Z, SO2 NH--Z and --OCOO--Z, wherein Z represents an alkyl having 1 to about 20 carbon atoms; each Y2 is --OH; each W1 is independently selected from the group consisting of substituents of formulas X1, --C(Cn H2n+1) (Cm H2m+1)--X1, wherein n and m are integers from 1 to about 20, --COO--X1, --CO--X1, --OCO--X1, --CH2 --O--X1, --O--CH2 --X1, --O--X1, --S--X1, --SO--X2, --SO2 --X1, --SO2 NH--X1, --OCOO--X1, cyclohexyl, and 5 or 6 -membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings; each W2 is independently selected from the group consisting of substituents of formulas X1, --C(Cn H2n+1) (Cm H2m+1)--X1, wherein n and m are integers from 1 to about 20, --COO--X1, --CO--X1, --OCO--X1, --O--X1, --S--X1, --SO--X1, --SO2 --X1, --SO2 NH--X1, --OCOO--X1, --COO--CH2 --X1, --OCO--CH2 --X1, --CH2 --COO--X1, --CH2 --OCO--X1, --O--C2 H4 --O--X1, cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon rings and each W3 is independently selected from the group consisting of substituents of formulas X1, --C(Cn H2n+1) (Cm H2m+1)--X1, wherein n and m are integers from 1 to about 20, --COO--X1, --CO--X1, --OCO--X1, --O--X1, --S--X1, --SO--X1, --SO2 --X1, --OCOO--X1, --CH2 --X1, cyclohexyl, and 5 or 6-membered aromatic, heteroalicyclic, heteroaromatic or alicyclic carbon ring; and each X1 is a group of formula (X) ##STR16## wherein R1 and R2 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. - View Dependent Claims (2, 3, 4, 5, 6, 7)
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Specification
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Current AssigneeNeste Oy (Neste Corporation)
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Original AssigneeNeste Oy (Neste Corporation)
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InventorsIkkala, Olli, Passiniemi, Pentti
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Primary Examiner(s)McGinty, Douglas J.
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Application NumberUS08/257,115Time in Patent Office720 DaysField of Search252/500, 252/518, 252/519, 252/520, 252/521, 525/540, 528/422US Class Current252/519.21CPC Class CodesC08G 73/0266 Polyanilines or derivatives...C08K 5/0008 Organic ingredients accordi...C08L 79/02 PolyaminesH01B 1/128 comprising six-membered aro...
