US5777070A
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Process for preparing conjugated polymers
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1997-10-23
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Granted: 1998-07-07
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Expires: 2017-10-23
Abstract
Abstract A process for preparing conjugated polymers which comprises contacting (i) monomers having two reactive groups selected from boronic acid, C 1 -C 6 boronic acid ester, C 1 -C 6 borane, and combinations thereof, with aromatic dihalide-functional monomers or (ii) monomers having one reactive boronic acid, boronic acid ester, or borane group and one reactive halide-functional group, with each other; (wherein the monomers are selected so that the polymerization reaction product of such has conjugated unsaturated internal groups) in a reaction mixture which contains: (a) an organic solvent in which the polymer forms at least a 1 percent solution; (b) an aqueous solution of an inorganic base having a pKa in the range of from 9 to 13, said solution having a concentration of at least 0.1N; (c) a catalytic amount of a palladium complex; and (d) at least 0.01 mole percent of a phase transfer catalyst, based on the number of moles of boronic acid, boric acid ester, and borane groups in the reaction mixture; under reaction conditions sufficient to form the corresponding conjugated polymer.
Inventors
- 👤 Michael Inbasekaran
- 👤 Weishi Wu
- 👤 Edmund P. Woo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 11:30
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08L; C08L65/00; H; H10; H10K; H10K50/00; H10K50/10; H10K50/11; H10K85/00; H10K85/10; H10K85/111; H10K85/113; H10K85/115; H10K85/151; H10K85/60; H10K85/631
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
177 words
A process for preparing a conjugated polymer which comprises contacting (i) monomers having two reactive groups selected from boronic acid, C 1 -C 6 boronic acid ester, C 1 -C 6 borane, and combinations thereof, with aromatic dihalide-functional monomers or (ii) monomers having one reactive boronic acid, boronic acid ester, or borane group and one reactive halide-functional group, with each other; wherein the monomers are selected so that the polymerization reaction products of such have conjugated unsaturated internal groups; in a reaction mixture which contains: (a) an organic solvent in which the polymer forms at least a 1 percent solution; (b) an aqueous solution of an inorganic base having a pKa in the range of from 9 to 13, said solution having a concentration of at least 0.1N; (c) a catalytic amount of a palladium complex; and (d) at least 0.01 mole percent of a phase transfer catalyst, based on the number of moles of boronic acid, boric acid ester, and borane groups in the reaction mixture; under reaction conditions sufficient to form the corresponding conjugated polymer.
Claim 2
Dependent Claim
177 words
A process for preparing a conjugated polymer which comprises contacting (i) monomers having two reactive groups selected from boronic acid, C 1 -C 6 boronic acid ester, C 1 -C 6 borane, and combinations thereof, with aromatic dihalide-functional monomers or (ii) monomers having one reactive boronic acid, boronic acid ester, or borane group and one reactive halide-functional group, with each other; wherein the monomers are selected so that the polymerization reaction products of such have conjugated unsaturated internal groups; in a reaction mixture which contains: (a) an organic solvent in which the polymer forms at least a 1 percent solution; (b) an aqueous solution of an inorganic base having a pKa in the range of from 9 to 13, said solution having a concentration of at least 0.1N; (c) a catalytic amount of a palladium complex; and (d) at least 0.01 mole percent of a phase transfer catalyst, based on the number of moles of boronic acid, boric acid ester, and borane groups in the reaction mixture; under reaction conditions sufficient to form the corresponding conjugated polymer.
Claim 3
Dependent Claim
42 words
The process of claim 1 wherein the molar ratio of monomers (i) having two groups selected from boronic acid, C 1 -C 6 boronic acid ester, C 1 -C 6 borane, and combinations thereof, to aromatic dihalide-functional monomers is at least 1.02:1.00.
Claim 4
Dependent Claim
18 words
The process of claim 1 wherein the organic solvent is a C 6 -C 20 aromatic group-containing compound.
Claim 5
Dependent Claim
17 words
The process of claim 1 wherein the organic solvent is benzene, toluene, xylene, ethylbenzene, mesitylene, or anisole.
Claim 6
Dependent Claim
11 words
The process of claim 1 wherein the organic solvent is toluene.
Claim 7
Dependent Claim
20 words
The process of claim 1 wherein the inorganic base is an alkali metal carbonate, alkali metal bicarbonate, or mixture thereof.
Claim 8
Dependent Claim
20 words
The process of claim 4 wherein the inorganic base is an alkali metal carbonate, alkali metal bicarbonate, or mixture thereof.
Claim 9
Dependent Claim
15 words
The process of claim 1 wherein the inorganic base is sodium carbonate or potassium carbonate.
Claim 10
Dependent Claim
15 words
The process of claim 4 wherein the inorganic base is sodium carbonate or potassium carbonate.
Claim 11
Dependent Claim
29 words
The process of claim 6 wherein the inorganic base is employed in an amount sufficient to provide a molar ratio of base to halide-functional monomer of at least 2:1.
Claim 12
Dependent Claim
32 words
The process of claim 1 wherein the palladium complex is employed in an amount sufficient to provide a molar ratio or palladium to monomer in the range of from 0.001:1 to 0.05:1.
Claim 13
Dependent Claim
32 words
The process of claim 4 wherein the palladium complex is employed in an amount sufficient to provide a molar ratio or palladium to monomer in the range of from 0.001:1 to 0.05:1.
Claim 14
Dependent Claim
32 words
The process of claim 7 wherein the palladium complex is employed in an amount sufficient to provide a molar ratio or palladium to monomer in the range of from 0.001:1 to 0.05:1.
Claim 15
Dependent Claim
32 words
The process of claim 9 wherein the palladium complex is employed in an amount sufficient to provide a molar ratio or palladium to monomer in the range of from 0.001:1 to 0.05:1.
Claim 16
Dependent Claim
17 words
The process of claim 1 wherein the phase transfer catalyst is C 4 -C 30 tetraalkylammonium halide.
Claim 17
Dependent Claim
17 words
The process of claim 4 wherein the phase transfer catalyst is C 4 -C 30 tetraalkylammonium halide.
Claim 18
Dependent Claim
17 words
The process of claim 7 wherein the phase transfer catalyst is C 4 -C 30 tetraalkylammonium halide.
Claim 19
Dependent Claim
17 words
The process of claim 9 wherein the phase transfer catalyst is C 4 -C 30 tetraalkylammonium halide.
Claim 20
Dependent Claim
29 words
The process of claim 1 wherein the phase transfer catalyst is employed in an amount sufficient to provide a molar ratio of catalyst to monomer of at least 0.01:1.
Claim 21
Dependent Claim
22 words
The process of claim 1 wherein the polymer reaches a degree of polymerization of at least 20 in less than 24 hours.
Claim 22
Dependent Claim
42 words
The process of claim 20 wherein the molar ratio of monomers having two groups selected from boronic acid, C 1 -C 6 boronic acid ester, C 1 -C 6 borane, and combinations thereof to aromatic dihalide-functional monomers is no greater than 1.10:1.00.
Claim 23
Dependent Claim
103 words
The process of claim 1 wherein the polymer contains at least 20 groups of the formula: ##STR13## wherein Ar is a conjugated unsaturated group; and R 1 is independently in each occurrence C 1 -C 20 hydrocarbyl or C 1 -C 20 hydrocarbyl containing one or more S, N, O, P or Si atoms, C 4 -C 16 hydrocarbyl carbonyloxy, C 4 -C 16 aryl(trialkylsiloxy) or both, R 1 may form with the 9-carbon on the fluorene ring a C 5 -C 20 ring structure or a C 4 -C 20 ring structure containing one or more heteroatoms of S, N or O.
Claim 24
Dependent Claim
9 words
The process of claim 12 wherein Ar is benzothiadiazole.
References Cited (Backward Citations)
No citation records indexed.
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