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US 6,586,554 B1Granted
Polyarylene and method for production thereof
AssigneeJapan Science and Technology Corporation
InventorTamotsu Takahashi
Life of this patent
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Abstract
This invention provides polyarylenes having a recurring unit shown by formula (I) or (II) below and a process for production thereof as well as these monomers: (wherein Ar1 and Ar2 are an arylene; R1 and R2 are C1-C20 hydrocarbon group, etc.; A1 and A2 are C1-C20 hydrocarbon group, etc.; and n is an integer of 2 or more); (wherein Ar1 and Ar2 are an arylene; R1 and R2 are C1-C20 hydrocarbon group, etc.; A1 and A2 are C1-C20 hydrocarbon group, etc.; and n is an integer of 2 or more) The polyarylenes of the invention find extensive applications as electrically conductive resins. The polyarylenes can be used also as resin compositions in a variety of formed shapes.
Claims19
A polyarylene comprising a recurring unit of formula (I) or (II) below:
- (wherein:
- Ar1 and Ar2, which may be the same or different, each represents independently an arylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
- R1 and R2, which may be the same or different, each represents independently a C1-C20 hydrocarbon group which may be substituted, a C1-C20 alkoxy group which may be substituted, a C6-C20aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula:
- —Si(R3)(R4)(R5) (wherein R3, R4 and R5, which may be the same or different, each represents independently a C1-C20 alkyl group, a C6-C20 arylalkyl group, a C1-C20 alkoxy group or a C6-C20 arylalkyloxy group);
- provided that, in the recurring unit of formula (I), R1 and R2 may form together a C4-C20 saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
- A1 and A2, which may be the same or different, each represents independently hydrogen atom;
- a C1-C20 hydrocarbon group which may be substituted;
- a C1-C20 alkoxy group which may be substituted;
- a C6-C20 aryloxy group which may be substituted;
- a C6-C20 alkylaryloxy group which may be substituted;
- a C1-C20 alkoxycarbonyl group which may be substituted;
- a C6-C20 aryloxycarbonyl group which may be substituted;
- cyano group (—CN);
- carbamoyl group (—C(═O)NH2);
- a haloformyl group (—C(═O)—X, wherein X is a halogen atom);
- or formyl group (—C(═O)—H);
- and,
- n is an integer of 2 or more).
15 more elements
A teraryl represented by formula (III) or (IV) below:
- (wherein:
- Ar1 and Ar2, which may be the same or different, each represents independently an arylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
- R1 and R2, which may be the same or different, each represents independently a C1-C20 hydrocarbon group which may be substituted, a C1-C20 alkoxy group which may be substituted, a C6-C20 aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula:
- —Si(R3)(R4)(R5) (wherein R3, R4 and R5, which may be the same or different, each represents independently a C1-C20 alkyl group, a C6-C20 arylalkyl group, a C1-C20 alkoxy group or a C6-C20 arylalkyloxy group)
- provided that, in the recurring unit of formula (III), R1 and R2 may form together a C4-C20 saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
- A1 and A2, which may be the same or different, each represents independently hydrogen atom;
- a C1-C20 hydrocarbon group which may be substituted;
- a C1-C20 alkoxy group which may be substituted;
- a C6-C20 aryloxy group which may be substituted;
- a C6-C20 alkylaryloxy group which may be substituted;
- a C1-C20 alkoxycarbonyl group which may be substituted;
- a C6-C20 aryloxycarbonyl group which may be substituted;
- cyano group (—CN);
- carbamoyl group (—C(═O)NH2);
- a haloformyl group (—C(═O)—X, wherein X is a halogen atom);
- formyl group (—C(═O)—H);
- and,
- X1 and X2, which may be the same or different, each represents independently a leaving group).
15 more elements
A process for producing a polyarylene, which comprises polymerizing a teraryl represented by formula (III) or (IV) below:
- (wherein:
- Ar1 and Ar2, which may be the same or different, each represents independently an arylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
- R1 and R2, which may be the same or different, each represents independently a C1-C20 hydrocarbon group which may be substituted, a C1-C20 alkoxy group which may be substituted, a C6-C20aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula:
- —Si(R3)(R4)(R5) (wherein R3, R4 and R5, which may be the same or different, each represents independently a C1-C20 alkyl group, a C6-C20 arylalkyl group, a C1-C20 alkoxy group or a C6-C20 arylalkyloxy group);
- provided that, in the recurring unit of formula (III), R1 and R2 may form together a C4-C20 saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
- A1 and A2, which may be the same or different, each represents independently hydrogen atom;
- a C1-C20 hydrocarbon group which may be substituted;
- a C1-C20 alkoxy group which may be substituted;
- a C6-C20 aryloxy group which may be substituted;
- a C6-C20 alkylaryloxy group which may be substituted;
- a C1-C20 alkoxycarbonyl group which may be substituted;
- a C6-C20 aryloxycarbonyl group which may be substituted;
- cyano group (—CN);
- carbamoyl group (—C(═O)NH2);
- a haloformyl group (—C(═O)—X, wherein X is a halogen atom);
- or formyl group (—C(═O)—H);
- and,
- X1 and X2, which may be the same or different, each represents independently a leaving group);
- to produce a polyarylene represented by formula (I) or (II) below:
- (wherein each of Ar1, Ar2, R1, R2, A1 and A2 has the same significance as defined above;
- and n is an integer of 2 or more).
18 more elements
A process for producing a polyarylene, which comprises reacting a metallacyclopentadiene represented by formula (V) or (VI) below:
- (wherein:
- Ar1 and Ar21 which may be the same or different, each represents independently an arylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
- R1 and R2, which may be the same or different, each represents independently a C1-C20 hydrocarbon group which may be substituted, a C1-C20 alkoxy group which may be substituted, a C6-C20aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula:
- —Si(R3)(R4)(R5) (wherein R3, R4 and R5, which may be the same or different, each represents independently a C1-C20 alkyl group, a C6-C20 arylalkyl group, a C1-C20 alkoxy group or a C6-C20 arylalkyloxy group);
- provided that, in the metallacyclopentadiene shown by formula (V), R1 and R2 may form together a C4-C20 saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
- M is a metal from Groups III-V or the lanthanide series of the Periodic Table;
- L1 and L2, which may be the same or different, each represents independently an anionic ligand, provided that L1 and L2 may be crosslinked;
- and,
- X1 and X2, which may be the same or different, each represents independently a leaving group);
- with an alkyne derivative represented by formula (VII) below:
- A1a—C≡C—A2a (VII)
- (wherein;
- A1a and A2a, which may be the same or different, each represents independently hydrogen atom;
- a C1-C20 hydrocarbon group which may be substituted;
- a C1-C20 alkoxy group which may be substituted;
- a C6-C20 aryloxy group which may be substituted;
- a C6-C20 alkylaryloxy group which may be substituted;
- a C1-C20 alkoxycarbonyl group which may be substituted;
- a C6-C20 aryloxycarbonyl group which may be substituted;
- or cyano group (—CN));
- to produce a teraryl represented by formula (IIIa) or (IVa) below:
- (wherein each of Ar1, Ar2, R1, R2 A1a, A2a, X1 and X2 has the same significance as defined above);
- and polymerizing the resulting teraryl to produce the polyarylene represented by formula (Ia) or (IIa) below:
- (wherein each of Ar1, Ar2, R2, R2, A1a and A2a has the same significance as defined above;
- and n is an integer of 2 or more).
22 more elements
A metallacyclopentadiene represented by formula (V) or (VI) below:
- (wherein:
- M is a metal from Groups III-V or the lanthanide series of the Periodic Table;
- L1 and L2, which may be the same or different, each represents independently an anionic ligand, provided that L1 and L2 may be crosslinked;
- Ar1 and Ar2, which may be the same or different, each represents independently an arylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
- R1 and R2, which may be the same or different, each represents independently a C1-C20 hydrocarbon group which may be substituted, a C1-C20 alkoxy group which may be substituted, a C6-C20 aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula:
- —Si(R3)(R4)(R5)(wherein R3, R4 and R5, which may be the same or different, each represents independently a C1-C20 alkyl group, a C6-C20 arylalkyl group, a C1-C20 alkoxy group or a C6-C20 arylalkyloxy group);
- provided that, in the metallacyclopentadiene shown by formula (V), R1 and R2 may form together a C4-C20 saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
- and,
- X1 and X2, which may be the same or different, each represents independently a leaving group).
6 more elements
A polyarylene comprising a recurring unit represented by formula (I) below:
- (wherein:
- Ar1 and Ar2, which may be the same or different, each represents independently a paraarylene having 4 to 18 carbon atoms, which may be substituted and may contain 1 to 5 nitrogen atoms;
- R1 and R2, which may be the same or different, each represents independently a C1-C20 hydrocarbon group which may be substituted, a C1-C20 alkoxy group which may be substituted, a C6-C20aryloxy group which may be substituted, an amine group, hydroxy group or a group shown by formula:
- —Si(R3)(R4)(R5) (wherein R3, R4 and R5, which may be the same or different, each represents independently a C1-C20 alkyl group, a C6-C20 arylalkyl group, a C1-C20 alkoxy group or a C6-C20 arylalkyloxy group);
- provided that, in the recurring unit of formula (I), R1 and R2 may form together a C4-C20 saturated or unsaturated ring which may be intervened by an oxygen atom and may be substituted;
- A1 and A2, which may be the same or different, each represents independently hydrogen atom;
- a C1-C20 hydrocarbon group which may be substituted;
- a C1-C20 alkoxy group which may be substituted;
- a C6-C20 aryloxy group which may be substituted;
- a C6-C20 alkylaryloxy group which may be substituted;
- an alkoxycarbonyl group which may be substituted;
- a C6-C20 aryloxycarbonyl group which may be substituted;
- cyano group (—CN);
- carbamoyl group (—C(═O)NH2);
- a haloformyl group (—C(═O)—X, wherein X is a halogen atom);
- or formyl group (—C(═O)—H);
- and,
- n is an integer of 2 or more).
15 more elements
Dependencies are inferred from the claim text.