A method of preparing an electrolyte membrane comprising a crosslinked object of a polybenzoxazine-based compound formed of a polymerized resultant product of a first monofunctional benzoxazine-based monomer or a second benzoxazine-based monomer multifunctional benzoxazine-based monomer with a cross
A method of preparing an electrolyte membrane comprising a crosslinked object of a polybenzoxazine-based compound formed of a polymerized resultant product of a first monofunctional benzoxazine-based monomer or a second benzoxazine-based monomer multifunctional benzoxazine-based monomer with a crosslinkable compound.
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1. A method of preparing an electrolyte membrane comprising a crosslinked object of a polybenzoxazine-based compound formed of a polymerized resultant product of a first benzoxazine-based monomer represented by Formula 1 below or a second benzoxazine-based monomer represented by Formula 2 below with
1. A method of preparing an electrolyte membrane comprising a crosslinked object of a polybenzoxazine-based compound formed of a polymerized resultant product of a first benzoxazine-based monomer represented by Formula 1 below or a second benzoxazine-based monomer represented by Formula 2 below with a crosslinkable compound, the method comprising: mixing the first benzoxazine-based monomer of Formula 1 or the second benzoxazine-based monomer of Formula 2 with the crosslinkable compound to form a resultant mixture, the crosslinkable compound including at least one of a polybenzimidazole, a polybenzthiazole, a polybenzoxazole, and a polyimide; andcuring the resultant mixture to form a resultant, and then impregnating the resultant with a proton conductor: wherein, R1 in Formula 1 is hydrogen, a substituted or nonsubstituted C1-C20 alkyl group, a substituted or nonsubstituted C1-C20 alkenyl group, a substituted or nonsubstituted C1-C20 alkynyl group, a substituted or nonsubstituted C6-C20 aryl group, a substituted or nonsubstituted C2-C20 heteroaryl group, a substituted or nonsubstituted C4-C20 cycloalkyl group, a substituted or nonsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group; andR2 in Formula 1 is a substituted or nonsubstituted C1-C20 alkyl group, a substituted or nonsubstituted C1-C20 alkenyl group, a substituted or nonsubstituted C1-C20 alkynyl group, a substituted or nonsubstituted C6-C20 aryl group, a substituted or nonsubstituted C7-C20 arylalkyl group, a substituted or nonsubstituted C2-C20 heteroaryl group, a substituted or nonsubstituted C2-C20 heteroarylalkyl group, a substituted or nonsubstituted C4-C20 carbocyclic group, a substituted or nonsubstituted C4-C20 carbocyclic alkyl group, a substituted or nonsubstituted C2-C20 heterocyclic group, or a substituted or nonsubstituted C2-C20 heterocyclic alkyl group; wherein, R2 in Formula 2 is a substituted or nonsubstituted C1-C20 alkyl group, a substituted or nonsubstituted C1-C20 alkenyl group, a substituted or nonsubstituted C1-C20 alkynyl group, a substituted or nonsubstituted C6-C20 aryl group, a substituted or nonsubstituted C7-C20 arylalkyl group, a substituted or nonsubstituted C2-C20 heteroaryl group, a substituted or nonsubstituted C2-C20 heteroarylalkyl group, a substituted or nonsubstituted C4-C20 carbocyclic group, a substituted or nonsubstituted C4-C20 carbocyclic alkyl group, a substituted or nonsubstituted C2-C20 heterocyclic group, or a substituted or nonsubstituted C2-C20 heterocyclic alkyl group; andR3 in Formula 2 is a substituted or nonsubstituted C1-C20 alkylene group, a substituted or nonsubstituted C1-C20 alkenylene group, a substituted or nonsubstituted C1-C20 alkynylene group, a substituted or nonsubstituted C6-C20 arylene group, a substituted or nonsubstituted C2-C20 heteroarylene group, —C(═O)—, or —SO2—. 2. The method of claim 1, wherein the mixing of the first benzoxazine-based monomer of Formula 1 or the second benzoxazine-based monomer of Formula 2 with the crosslinkable compound comprises: preparing the first benzoxazine-based monomer of Formula 1 according to the following reaction scheme: or preparing the second benzoxazine-based monomer of Formula 2 according to at least one of the following reaction schemes: 3. The method of claim 1, wherein an amount of the crosslinkable compound is in a range of 5 to 95 parts by weight based on 100 parts by weight of the first or second benzoxazine-based monomer. 4. The method of claim 1, wherein the curing of the resultant mixture is performed at 50 to 250° C. 5. The method of claim 1, wherein an amount of the proton conductor is in a range of 100 to 1,000 parts by weight based on 100 parts by weight of the crosslinkable compound. 6. The method of claim 1, wherein the proton conductor is at least one selected from the group of phosphoric acid and a C1-C10 alkyl phosphoric acid; and an amount of the proton conductor is in a range of 100 to 1,000 parts by weight based on 100 parts by weight of the crosslinked object of the polybenzoxazine-based compound. 7. A method of preparing a fuel cell employing an electrolyte membrane produced by the method of claim 1, the method comprising: laminating an electrode having a catalyst layer on each side of the electrolyte membrane to form a membrane electrode assembly (MEA); andattaching a bipolar plate to each side of the MEA. 8. The method of claim 7, wherein the laminating of the electrodes on the electrolyte membrane includes binding the electrodes to the electrolyte membrane at a temperature where the electrolyte membrane is softened and at a high pressure in a range of 0.1 to 3 ton/cm2. 9. A method of preparing an electrolyte membrane comprising a crosslinked object of a polybenzoxazine-based compound formed of a polymerized resultant product of a first benzoxazine-based monomer represented by Formula 1 below or a second benzoxazine-based monomer represented by Formula 2 below with a crosslinkable compound, the method comprising: mixing the first benzoxazine-based monomer of Formula 1 or the second benzoxazine-based monomer of Formula 2 with the crosslinkable compound to form a resultant mixture, the crosslinkable compound including at least one of a polybenzimidazole, a polybenzthiazole, a polybenzoxazole, and a polyimide; andforming a membrane on a supporter using the resultant mixture, then curing the resultant mixture to form a resultant, and then impregnating the cured resultant with a proton conductor: wherein, R1 in Formula 1 is hydrogen, a substituted or nonsubstituted C1-C20 alkyl group, a substituted or nonsubstituted C1-C20 alkenyl group, a substituted or nonsubstituted C1-C20 alkynyl group, a substituted or nonsubstituted C6-C20 aryl group, a substituted or nonsubstituted C2-C20 heteroaryl group, a substituted or nonsubstituted C4-C20 cycloalkyl group, a substituted or nonsubstituted C2-C20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group; andR2 in Formula 1 is a substituted or nonsubstituted C1-C20 alkyl group, a substituted or nonsubstituted C1-C20 alkenyl group, a substituted or nonsubstituted C1-C20 alkynyl group, a substituted or nonsubstituted C6-C20 aryl group, a substituted or nonsubstituted C7-C20 arylalkyl group, a substituted or nonsubstituted C2-C20 heteroaryl group, a substituted or nonsubstituted C2-C20 heteroarylalkyl group, a substituted or nonsubstituted C4-C20 carbocyclic group, a substituted or nonsubstituted C4-C20 carbocyclic alkyl group, a substituted or nonsubstituted C2-C20 heterocyclic group, or a substituted or nonsubstituted C2-C20 heterocyclic alkyl group; wherein, R2 in Formula 2 is a substituted or nonsubstituted C1-C20 alkyl group, a substituted or nonsubstituted C1-C20 alkenyl group, a substituted or nonsubstituted C1-C20 alkynyl group, a substituted or nonsubstituted C6-C20 aryl group, a substituted or nonsubstituted C7-C20 arylalkyl group, a substituted or nonsubstituted C2-C20 heteroaryl group, a substituted or nonsubstituted C2-C20 heteroarylalkyl group, a substituted or nonsubstituted C4-C20 carbocyclic group, a substituted or nonsubstituted C4-C20 carbocyclic alkyl group, a substituted or nonsubstituted C2-C20 heterocyclic group, or a substituted or nonsubstituted C2-C20 heterocyclic alkyl group; andR3 in Formula 2 is a substituted or nonsubstituted C1-C20 alkylene group, a substituted or nonsubstituted C1-C20 alkenylene group, a substituted or nonsubstituted C1-C20 alkynylene group, a substituted or nonsubstituted C6-C20 arylene group, a substituted or nonsubstituted C2-C20 heteroarylene group, —C(═O)—, or —SO2—. 10. The method of claim 9, wherein the impregnating of the cured resultant with a proton conductor comprises: impregnating in phosphoric acid at 110° C., for 1 hour, in a vacuum, and then again at 110° C. for 10 hours, under a normal atmospheric pressure. 11. The method of claim 9, wherein the forming of the membrane is performed by tape casting the resultant mixture on the supporter. 12. The method of claim 9, wherein the forming of the membrane is performed by casting the resultant mixture on the supporter. 13. The method of claim 9, further comprising detaching the cured resultant from the supporter to remove the supporter. 14. The method of claim 9, wherein an amount of the crosslinkable compound is in a range of 5 to 95 parts by weight based on 100 parts by weight of the first or second benzoxazine-based monomer. 15. The method of claim 9, wherein the curing of the resultant mixture is performed at 50 to 250° C. 16. The method of claim 9, wherein an amount of the proton conductor is in a range of 100 to 1,000 parts by weight based on 100 parts by weight of the crosslinkable compound. 17. The method of claim 9, wherein the proton conductor is at least one selected from the group of phosphoric acid and a C1-C10 alkyl phosphoric acid; and an amount of the proton conductor is in a range of 100 to 1,000 parts by weight based on 100 parts by weight of the crosslinked object of the polybenzoxazine-based compound. 18. A method of preparing a fuel cell employing an electrolyte membrane produced by the method of claim 9, the method comprising: laminating an electrode having a catalyst layer on each side of the electrolyte membrane to form a membrane electrode assembly (MEA); andattaching a bipolar plate to each side of the MEA. 19. The method of claim 18, wherein one of the electrodes is an anode, and the catalyst layer of the anode comprises a platinum-cobalt alloy having a platinum loading in a range of 2.2 to 3.5 mg/cm3.
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이 특허에 인용된 특허 (16)
Ishida Hatsuo, Cationic ring-opening polymerization of benzoxazines.
Connell John W. (Yorktown VA) Hergenrother Paul M. (Yorktown VA) Smith ; Jr. Joseph G. (Yorktown VA), Poly(N-arylenebenzimidazoles) via aromatic nucleophilic displacement.
Connell John W. (Yorktown VA) Hergenrother Paul M. (Yorktown VA) Smith ; Jr. Joseph G. (Yorktown VA), Polybenzimidazoles via aromatic nucleophilic displacement.
Onorato Frank J. ; Sansone Michael J. ; Kim Dai W. ; French Stuart M. ; Marikar Faruq, Process for producing polybenzimidazole fabrics for use in fuel.
Onorato Frank J. ; Sansone Michael J. ; French Stuart M. ; Marikar Faruq, Process for producing polybenzimidazole pastes and gels for use in fuel cells.
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