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1. 发明授权

US06825310B2 Halogenated aromatic compound, polymer thereof, and proton-conductive membrane comprising same 有权
标题翻译：卤化芳族化合物，其聚合物和包含其的质子传导膜
公开(公告)号：US06825310B2
公开(公告)日：2004-11-30
申请号：US10105213
申请日：2002-03-26
申请人： Kohei Goto , Masayuki Takahashi , Yoshitaka Yamakawa , Makoto Higami
发明人： Kohei Goto , Masayuki Takahashi , Yoshitaka Yamakawa , Makoto Higami
IPC分类号： C08G6538
CPC分类号： H01B1/122 , C07C45/71 , C07C49/84 , C07C317/22 , C08G61/12 , C08G65/40 , C08G65/4018 , C08G65/4025 , C08G75/23 , C08J5/2256 , C08J2381/06 , H01M6/181 , H01M2300/0082
摘要： A polymer which has a flexible structure in its main chain and thus exhibits a high toughness and can difficultly be deteriorated in its mechanical properties and thermal properties even when sulfonated, a sulfonic acid group-containing polymer obtained by the sulfonation of the polymer, and a proton-conductive membrane having an excellent mechanical strength and durability made of the sulfonic acid group-containing polymer. A novel halogenated aromatic compound represented by the following general formula (1m) is provided: wherein A independently represents an electron-withdrawing group; B independently represents an electron-donating atom or group; X represents a chlorine atom, iodine atom or bromine atom; R1 to R8 may be the same or different and each represent a hydrogen atom, fluorine atom or alkyl group; and n represents an integer of 2 or more.
摘要翻译：一种聚合物，其主链具有柔性结构，因此即使在磺化时也显示出高的韧性并且难以在其机械性能和热性能上劣化，通过聚合物磺化得到的含磺酸基的聚合物和质子传导膜具有优异的机械强度和耐久性，由含磺酸基的聚合物制成。提供由以下通式（1m）表示的新型卤代芳族化合物：其中A独立地表示吸电子基团; B独立地表示给电子原子或基团; X表示氯原子，碘原子或溴原子; R 1至R 8可以相同或不同，各自表示氢原子，氟原子或烷基; n表示2以上的整数。

2. 发明授权

US06794480B2 Monomer containing electron-withdrawing group and electron-donative group, and copolymer and proton-conductive membrane comprising same 有权
标题翻译：含有吸电子基团和给电子基团的单体，以及包含其的共聚物和质子传导膜
公开(公告)号：US06794480B2
公开(公告)日：2004-09-21
申请号：US10105316
申请日：2002-03-26
申请人： Kohei Goto , Masayuki Takahashi , Yoshitaka Yamakawa , Makoto Higami
发明人： Kohei Goto , Masayuki Takahashi , Yoshitaka Yamakawa , Makoto Higami
IPC分类号： C08G1400
CPC分类号： C08J5/2256 , C07C45/71 , C07C49/84 , C08G61/12 , C08G65/48 , C08J2371/12
摘要： A monomer containing an electron-withdrawing group and an electron-donative group which can be easily controlled in the upper limit of the amount of a sulfonic acid, which impairs the mechanical properties of a copolymer, and can provide a sulfonated polymer that forms a proton-conductive membrane having a high proton conductivity over a wide temperature range, an excellent mechanical strength and an excellent proton conductivity and showing inhibited swelling in hot water and an aqueous solution of methanol, and a copolymer obtained from the monomer. A monomer containing an electron-withdrawing group and an electron-donative group represented by the following general formula (1): wherein Y represents a iodine atom, chlorine atom or bromine atom; X represents an electron-withdrawing group; B represents an electron-donative group; and Z represents an aryl group having a specific structure or a monovalent condensed ring hydrocarbon group such as naphthyl group.
摘要翻译：含有吸电子基团和电子给予基团的单体可以容易地控制在磺酸的上限的上限，这损害了共聚物的机械性能，并且可以提供形成质子的磺化聚合物导电膜在宽温度范围内具有高质子传导性，优异的机械强度和优异的质子传导性，并且在热水和甲醇水溶液中显示出抑制的溶胀，以及由单体获得的共聚物。含有由以下通式（1）表示的吸电子基团和给电子基团的单体：其中Y表示碘原子，氯原子或溴原子; X表示吸电子基团; B代表给电子基团; Z表示具有特定结构的芳基或萘基等单价稠环烃基。

3. 发明授权

US06833426B2 Halogenated aromatic compound, (co)polymer thereof, and proton-conductive membrane comprising same 有权
标题翻译：卤化芳香族化合物，（共）聚合物和包含其的质子传导膜
公开(公告)号：US06833426B2
公开(公告)日：2004-12-21
申请号：US10347336
申请日：2003-01-21
申请人： Yoshitaka Yamakawa , Masayuki Takahashi , Kohei Goto
发明人： Yoshitaka Yamakawa , Masayuki Takahashi , Kohei Goto
IPC分类号： C08G6500
CPC分类号： C07C49/84 , C07C45/46 , C07C45/71 , C07C317/22 , C08G61/12 , C08G65/38 , C08G65/4018 , C08G65/48 , C08G75/23 , C08J5/2256 , C08J2371/12
摘要： A halogenated aromatic compound, a polyarylene (co)polymer obtained by the polymerization of such a halogenated aromatic compound as a monomer component, and a proton-conductive membrane made of a sulfonation product of such a (co)polymer are disclosed. The halogenated aromatic compound is represented by the following general formula (1bm): wherein As′ independently represent an electron-withdrawing group; Bs′ independently represent an electron-donating atom or divalent group; Xs′ independently represent a chlorine atom, an iodine atom, or a bromine atom; Z represents an aryl group; R1 to R19 may be the same or different and each represents a hydrogen atom, a fluorine atom, an alkyl group, or a fluoroalkyl group; and a and b each represents an integer of 1 to 20.
摘要翻译：公开了通过使这种卤化芳族化合物作为单体成分聚合得到的聚亚芳基（共）聚合物和由这种（共）聚合物的磺化产物制成的质子传导膜的卤代芳族化合物。卤代芳族化合物由以下通式（1bm）表示：其中As'独立地表示吸电子基团; Bs'独立地表示给电子原子或二价基团; X'独立地表示氯原子，碘原子或溴原子; Z表示芳基; R 1至R 19可以相同或不同，各自表示氢原子，氟原子，烷基或氟代烷基; a和b各自表示1〜20的整数。

4. 发明授权

US07163988B2 Aromatic sulfonic acid ester derivative, polyarylene, polyarylene having sulfonic acid group and process for producing the same, and polymer solid electrolyte and proton-conductive membrane 有权
标题翻译：芳族磺酸酯衍生物，聚亚芳基，具有磺酸基的聚亚芳基及其制备方法，以及聚合物固体电解质和质子传导膜
公开(公告)号：US07163988B2
公开(公告)日：2007-01-16
申请号：US10642694
申请日：2003-08-19
申请人： Igor Rozhanskii , Masayuki Takahashi , Kohei Goto , Yousuke Konno , Toshihiro Ohtsuki , Yoshitaka Yamakawa , Toshiaki Kadota
发明人： Igor Rozhanskii , Masayuki Takahashi , Kohei Goto , Yousuke Konno , Toshihiro Ohtsuki , Yoshitaka Yamakawa , Toshiaki Kadota
IPC分类号： C08F283/08 , C08G61/10
CPC分类号： C08G61/12 , C07C309/73 , C07C309/75
摘要： Disclosed is an aromatic sulfonic acid ester derivative represented by the formula (1); in the formula, X is an atom or a group selected from a halogen atom excluding fluorine, —OSO3CH3 and —OSO3CF3, A is a divalent electron attractive group, B is a divalent electron donating group or a direct bonding, Ra is a hydrocarbon group of 1 to 20 carbon atoms, Ar is an aromatic group having a substituent of —SO3Rb (wherein Rb is a hydrocarbon group of 1 to 20 carbon atoms), m is an integer of 0 to 10, n is an integer of 0 to 10 and k is an integer of 1 to 4. Also disclosed is a process for producing a polyarylene having a sulfonic acid group, which process comprises the steps of coupling polymerization of an aromatic compound containing the derivative of the formula (1), to prepare a polyarylene and hydrolysis of the polyarylene, and which process has high safety and is easily capable of controlling the amount of sulfonoc acid group introduced into a polymer and the introducing position thereof.
摘要翻译：公开了由式（1）表示的芳族磺酸酯衍生物; 在该式中，X是选自除氟以外的卤素原子的原子或基团，-OSO 3 CH 3和-OSO 3 CF A是二价吸电子基团，B是二价给电子基团或直接键合，R a是1-20个碳原子的烃基，Ar 是具有-SO 3 R b的取代基的芳香族基团（其中R b为1〜20个碳原子的烃基）， m为0〜10的整数，n为0〜10的整数，k为1〜4的整数。还公开了具有磺酸基的聚亚芳基的制造方法，该方法包括使聚合的含有式（1）的衍生物的芳族化合物，以制备聚亚芳基并且聚亚芳基的水解，并且该方法具有高安全性并且易于控制引入聚合物的磺酸基团的量和引入位置那里 F。

5. 发明申请

US20060269655A1 Process for producing electrolyte membrane-bonded electrode and varnish composition used therein 审中-公开
公开(公告)号：US20060269655A1
公开(公告)日：2006-11-30
申请号：US11498173
申请日：2006-08-03
申请人： Makoto Higami , Kohei Goto , Nagayuki Kanaoka , Ryoichiro Takahashi , Yoichi Asano , Osamu Kakutani , Gen Okiyama
发明人： Makoto Higami , Kohei Goto , Nagayuki Kanaoka , Ryoichiro Takahashi , Yoichi Asano , Osamu Kakutani , Gen Okiyama
IPC分类号： B05D5/12
CPC分类号： H01M8/1023 , H01M4/8605 , H01M4/92 , H01M4/926 , H01M8/1004 , H01M8/1039 , H01M8/1053 , Y02P70/56
摘要： The present invention is intended to provide a process for producing an electrolyte membrane-bonded electrode having excellent power generation property when constitutes an electrode assembly, and a varnish composition for an electrolyte, by the use of which an electrolyte membrane-electrode bonded structure capable of retaining excellent power generation property is obtained. A process for producing a first electrolyte membrane-bonded electrode comprises applying, onto an electrode, a water-containing dispersion containing a perfluorosulfonic acid polymer, an organic solvent A and water and having a perfluorosulfonic acid polymer content of 0.5 to 20% by weight and then applying, onto the resulting film, a solution of sulfonated polyarylene in an organic solvent B, to form an electrolyte membrane. A process for producing a second electrolyte membrane-bonded electrode comprises applying, onto an electrode, a solution or dispersion containing a proton-conductive polymer, an organic solvent B and water and having a water content of 25 to 50% by weight and then applying, onto the resulting film, a solution or dispersion containing a proton-conductive polymer, an organic solvent B and water and having a water content of less than 25% by weight, to form an electrolyte membrane. A process for producing a third electrolyte membrane-bonded electrode comprises applying, onto an electrode, a varnish composition 6 obtained by dissolving a sulfonated polymer in a solvent containing an organic solvent C, an organic solvent D and water to form an electrolyte membrane, said organic solvent C being a good solvent for the sulfonated polymer and having a higher boiling point than that of other solvent components, said organic solvent D having a boiling point of not lower than 50° C. and being not a good solvent for the sulfonated polymer when used alone but causing a solubility region of the sulfonated polymer to appear when mixed with the organic solvent C and/or the water. The varnish composition 6 of the invention is a varnish composition obtained by dissolving the sulfonated polymer in a solvent containing an organic solvent C, an organic solvent D and water.

6. 发明授权

US06685984B2 Method for the production of multilayers 有权
标题翻译：生产多层膜的方法
公开(公告)号：US06685984B2
公开(公告)日：2004-02-03
申请号：US10447150
申请日：2003-05-29
申请人： Makoto Higami , Kohei Goto , Yoichi Asano , Ryoichiro Takahashi , Osamu Kakutani , Gen Okiyama
发明人： Makoto Higami , Kohei Goto , Yoichi Asano , Ryoichiro Takahashi , Osamu Kakutani , Gen Okiyama
IPC分类号： B05D512
CPC分类号： H01M8/1004 , H01M8/1025 , H01M8/1027 , H01M8/1032 , H01M8/1039 , H01M8/1081 , H01M2300/0082 , Y02P70/56 , Y10T29/49115
摘要： The method for the production of multilayers comprises: applying a coating solution (I) which comprises a dissolved or dispersed proton-conductive polymer and a solvent (Is) containing water in amounts from 25 to 60 wt % and an organic solvent in amounts from 75 down to 40 wt %, on an electrode, applying a coating solution (II) which comprises a dissolved or dispersed proton-conductive polymer and a solvent (IIs) containing water in amounts from 0 to less than 25 wt % and an organic solvent in amounts above 75 wt %, on the wet first coating without any drying of the first coating; and drying the coatings to form an electrolyte membrane. The methods can provide multilayers capable of satisfactory power generation properties as an electrode structure by forming an electrolyte membrane on an electrode without causing any penetration of electrolyte into the electrode.
摘要翻译：制造多层膜的方法包括：将含有溶解或分散的质子传导性聚合物和含量为25〜60重量％的水的溶剂（Is）和有机溶剂的涂布溶液（I）在电极上施加包含溶解或分散的质子传导性聚合物的涂料溶液（II）和含有0至小于25重量％的水的溶剂（IIs）和有机溶剂，含量高于75重量％，在湿的第一涂层上，没有任何干燥第一涂层; 并干燥涂层以形成电解质膜。所述方法可以通过在电极上形成电解质膜而不会使电解质进入电极而使能够具有令人满意的发电性能的多层作为电极结构。

7. 发明申请

US20050026029A1 Process of producing electrode paste and electrode paset compositon 审中-公开
标题翻译：生产电极膏和电极桩组合物的工艺
公开(公告)号：US20050026029A1
公开(公告)日：2005-02-03
申请号：US10901052
申请日：2004-07-29
申请人： Junji Kawai , Makoto Higami , Kohei Goto , Ryoichiro Takahashi , Yoichi Asano
发明人： Junji Kawai , Makoto Higami , Kohei Goto , Ryoichiro Takahashi , Yoichi Asano
IPC分类号： H01M4/86 , H01M4/88 , H01M4/92 , H01M8/10 , H01M4/96
CPC分类号： H01M4/8828 , H01M4/8605 , H01M4/8652 , H01M4/8663 , H01M4/8673 , H01M4/926
摘要： A process of producing an electrode paste having excellent storage stability and capable of forming a catalyst layer that has a sufficient pore volume for high generating performance, and an electrode paste composition having such properties are disclosed. The process comprises mixing and agitating carbon black supporting a catalyst metal, a polymer electrolyte, an organic solvent and at least either carbon fiber or water thereby to finely disperse the carbon black to a predetermined mean particle diameter of particles dispersed in the mixed solution, and admixing a dispersant to the mixed solution and agitating the resultant mixture to obtain an electrode paste in which particles having a predetermined mean particle diameter are uniformly dispersed.
摘要翻译：公开了一种具有优异的储存稳定性并且能够形成具有足够的孔体积以获得高发生性能的催化剂层的电极糊的方法和具有这种性能的电极糊组合物。该方法包括混合和搅拌负载催化剂金属的炭黑，聚合物电解质，有机溶剂和至少一种碳纤维或水，从而将炭黑细分散到分散在混合溶液中的预定颗粒直径的颗粒，以及将分散剂混合到混合溶液中并搅拌所得混合物以获得其中具有预定平均粒径的颗粒均匀分散的电极浆料。

8. 发明授权

US06812290B2 Polyarylene copolymers and proton-conductive membrane 有权
标题翻译：聚亚芳基共聚物和质子传导膜
公开(公告)号：US06812290B2
公开(公告)日：2004-11-02
申请号：US10303821
申请日：2002-11-26
申请人： Kohei Goto , Yoshitaka Yamakawa , Mayumi Kakuta , Igor Rozhanskii
发明人： Kohei Goto , Yoshitaka Yamakawa , Mayumi Kakuta , Igor Rozhanskii
IPC分类号： C08F836
CPC分类号： C08G61/12 , C07C45/46 , C07C49/84
摘要： A polyarylene copolymer which comprises (A) aromatic compound units having a main chain containing one or more electron-withdrawing groups therein and (B) aromatic compound units having a main chain containing no electron-withdrawing groups therein, and a proton-conductive membrane comprising the polyarylene copolymer having sulfonic acid groups.
摘要翻译：一种聚亚芳基共聚物，其包含（A）具有含有一个或多个吸电子基团的主链的芳香族化合物单元和（B）具有不含吸电子基团的主链的芳香族化合物单元，以及质子传导性膜，所述聚亚芳基共聚物具有磺酸基。

9. 发明申请

US20090149625A1 AROMATIC COMPOUND HAVING FLUORENE SKELETON AND POLYARYLENE HAVING SULFONIC ACID GROUP 审中-公开
标题翻译：具有荧光素的芳香族化合物和具有亚磺酸的聚合物
公开(公告)号：US20090149625A1
公开(公告)日：2009-06-11
申请号：US12298443
申请日：2007-04-24
申请人： Yoshitaka Yamakawa , Yousuke Konno , Kohei Goto
发明人： Yoshitaka Yamakawa , Yousuke Konno , Kohei Goto
IPC分类号： C08G14/00 , C07C317/14
CPC分类号： H01B1/122 , C08G65/4012 , H01M8/1025 , H01M8/1027 , H01M8/103 , H01M8/1032 , H01M8/1039
摘要： Sulfonated polyarylenes have excellent processability and methanol resistance.The polyarylene includes a structural unit (S) represented by Formula (2-2) below and a structural unit (T) represented by Formula (2-3) below, the structural unit (S) accounting for a proportion “s” of 95 to 50 mol %, the structural unit (T) accounting for a proportion “t” of 5 to 50 mol % (“s”+“t”=100 mol %): wherein each A independently represents a divalent linking group represented by —CO— or —SO2—; and R1 to R4 each independently represent a hydrogen atom, a fluorine atom, an alkyl group or an aryl group.
摘要翻译：磺化聚亚芳基具有优异的加工性和耐甲醇性。聚亚芳基包括由下式（2-2）表示的结构单元（S）和由下式（2-3）表示的结构单元（T），结构单元（S）占比例“s”为95 至50摩尔％，结构单元（T）的比例“t”为5-50摩尔％（“s”+“t”= 100摩尔％））：其中每个A独立地表示由 - CO-或-SO 2 - ; R 1〜R 4各自独立地表示氢原子，氟原子，烷基或芳基。

10. 发明授权

US06555626B2 Polyarylene copolymers and proton-conductive membrane 有权
标题翻译：聚亚芳基共聚物和质子传导膜
公开(公告)号：US06555626B2
公开(公告)日：2003-04-29
申请号：US09818847
申请日：2001-03-28
申请人： Kohei Goto , Yoshitaka Yamakawa , Mayumi Kakuta , Igor Rozhanskii
发明人： Kohei Goto , Yoshitaka Yamakawa , Mayumi Kakuta , Igor Rozhanskii
IPC分类号： C08F836
CPC分类号： C08G61/12 , C07C45/46 , C07C49/84
摘要： A polyarylene copolymer which comprises (A) from 60 to 3 mol % aromatic compound units having a main chain containing one or more electron-withdrawing groups therein and (B) from 40 to 97 mol % aromatic compound units having a main chain containing no electron-withdrawing groups therein (provided that (A)+(B)=100 mol %), and a proton-conductive membrane comprising the polyarylene copolymer having sulfonic acid groups.
摘要翻译：一种聚亚芳基共聚物，其包含（A）60〜3摩尔％的含有一个或多个吸电子基团的主链的芳族化合物单元和（B）40〜97摩尔％的不含电子的主链的芳族化合物单元（A）+（B）= 100摩尔％）和包含具有磺酸基的聚亚芳基共聚物的质子传导膜。

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