公开(公告)号：US07595373B2

公开(公告)日：2009-09-29

申请号：US11314877

申请日：2005-12-20

申请人： Joyce Hung ,  Hongyi Zhou ,  Marianne Elisabeth Harmon ,  Daniel Joseph Brunelle ,  Hongwei Liu ,  David Roger Moore ,  Daniel Steiger

发明人： Joyce Hung ,  Hongyi Zhou ,  Marianne Elisabeth Harmon ,  Daniel Joseph Brunelle ,  Hongwei Liu ,  David Roger Moore ,  Daniel Steiger

IPC分类号： C08G2/00

CPC分类号： C08G75/23

摘要： Sulfonated block copolymer suitable for use as proton exchange membranes for fuel cells comprise sulfonated polyaryletherketone blocks and polyethersulfone blocks. The sulfonated polyaryletherketone blocks comprise structural units of formula the polyethersulfone blocks comprising structural units of formula wherein R1, R2, R3 and R4 are independently C1-C10 alkyl, C3-C12 cycloalkyl, C6-C14 aryl, allyl, alkenyl, alkoxy,halo, or cyano; Z and Z1 are independently a direct bond or O, S, (CH2)r; (CF2)r, C(CH3)2, C(CF3)2, or a combination thereof; M is H, a metal cation, a non-metallic inorganic cation, an organic cation or a mixture thereof a is 0 or an integer from 1 to 3; b, c and d are independently 0 or an integer from 1 to 4; m and n are independently 0 or 1; and r is an integer from 1 to 5.

摘要翻译： 适用于燃料电池质子交换膜的磺化嵌段共聚物包括磺化聚芳醚酮嵌段和聚醚砜嵌段。 所述磺化聚芳醚酮嵌段包含结构式的结构单元，所述结构单元包括结构单元，其中R 1，R 2，R 3和R 4独立地为C 1 -C 10烷基，C 3 -C 12环烷基，C 6 -C 14芳基，烯丙基，烯基，烷氧基， 或氰基; Z和Z1独立地是直接键或O，S，（CH 2）r; （CF 2）r，C（CH 3）2，C（CF 3）2或其组合; M为H，金属阳离子，非金属无机阳离子，有机阳离子或其混合物a为0或1〜3的整数; b，c和d独立地为0或1〜4的整数; m和n独立地为0或1; r为1〜5的整数。

公开(公告)号：US07547756B2

公开(公告)日：2009-06-16

申请号：US11263166

申请日：2005-10-31

申请人： Joyce Hung ,  Hongyi Zhou ,  Daniel Joseph Brunelle ,  Marianne Elisabeth Harmon ,  Daniel Steiger ,  Hongwei Liu ,  David Roger Moore

发明人： Joyce Hung ,  Hongyi Zhou ,  Daniel Joseph Brunelle ,  Marianne Elisabeth Harmon ,  Daniel Steiger ,  Hongwei Liu ,  David Roger Moore

IPC分类号： C08G75/23 ,  C08G75/20

CPC分类号： C08G65/4037 ,  C08G65/4043 ,  C08G65/4056 ,  C08L79/04

摘要： Sulfonated polyethersulfones and polymer compositions comprising sulfonated polyethersulfones and at least one inorganic heteropolyacid are useful as proton exchange membranes for fuel cells. The polyethersulfones include structural units derived from at least one biphenol monomer and a monomer of formula I wherein X is O, S or NR1; Y is N or CR5; R1, R2, R3 and R4 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl or substituted arylalkyl, or R3 and R4, taken together, form a 5- or 6-membered substituted or unsubstituted aliphatic or aromatic ring; R5 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl or substituted arylalkyl; and L is a direct bond or a divalent aromatic linker containing 6-12 carbons.

摘要翻译： 包含磺化聚醚砜和至少一种无机杂多酸的磺化聚醚砜和聚合物组合物可用作燃料电池的质子交换膜。 聚醚砜包括衍生自至少一种联苯酚单体的结构单元和式I的单体，其中X是O，S或NR1; Y为N或CR5; R 1，R 2，R 3和R 4独立地为氢，烷基，取代的烷基，芳基，取代的芳基，烷基芳基，取代的烷基芳基，芳烷基或取代的芳基烷基，或者R 3和R 4一起形成5-或6-元取代或未取代的 脂肪族或芳香环; R5是氢，烷基，取代的烷基，芳基，取代的芳基，烷基芳基，取代的烷基芳基，芳基烷基或取代的芳基烷基; L是直接键或含有6-12个碳原子的二价芳族连接体。

公开(公告)号：US07635744B2

公开(公告)日：2009-12-22

申请号：US11397109

申请日：2006-04-05

申请人： David Roger Moore ,  Hongyi Zhou ,  Christoph Georg Erben ,  Marianne Elisabeth Harmon ,  Joyce Hung ,  Hongwei Liu ,  Daniel Steiger ,  Daniel Joseph Brunelle

发明人： David Roger Moore ,  Hongyi Zhou ,  Christoph Georg Erben ,  Marianne Elisabeth Harmon ,  Joyce Hung ,  Hongwei Liu ,  Daniel Steiger ,  Daniel Joseph Brunelle

IPC分类号： C08G64/00 ,  C08G63/02

CPC分类号： C08G75/23

摘要： Reactive monomers containing the trifluorovinyloxy group may be copolymerized to form polymers useful as membranes, especially polymer electrolyte membranes for fuel cells. The monomers have the formula ((CF2CFO(R1)p)nArX2 wherein Ar is a trivalent, tetravalent or pentavalent, substituted or unsubstituted, aromatic or heteroaromatic, monocyclic or polycyclic group having from 5 to 50 carbon atoms; X is OH, SH, NR2aR2b, F or Br; p is 0 or 1; n is 1, 2 or 3; R1 is substituted or unsubstituted phenyl and R2a and R2b are independently H, C1-C8 alkyl or C1-C8 perfluoroalkyl.

摘要翻译： 含有三氟乙烯基氧基的反应性单体可以共聚以形成可用作膜的聚合物，特别是用于燃料电池的聚合物电解质膜。 单体具有式（（CF 2 CFO（R 1）p）nArX 2，其中Ar是具有5至50个碳原子的三价，四价或五价，取代或未取代的芳族或杂芳族单环或多环基团; X是OH，SH， NR2aR2b，F或Br; p是0或1; n是1,2或3; R1是取代或未取代的苯基，R2a和R2b独立地是H，C1-C8烷基或C1-C8全氟烷基。

公开(公告)号：US07393914B2

公开(公告)日：2008-07-01

申请号：US11193552

申请日：2005-07-29

申请人： David Roger Moore ,  Hongyi Zhou ,  Daniel Steiger ,  Joyce Hung ,  Daniel Joseph Brunelle ,  Hongwei Liu ,  Marianne Elisabeth Harmon

发明人： David Roger Moore ,  Hongyi Zhou ,  Daniel Steiger ,  Joyce Hung ,  Daniel Joseph Brunelle ,  Hongwei Liu ,  Marianne Elisabeth Harmon

IPC分类号： C08G75/00 ,  C08G8/02

CPC分类号： G11B7/22 ,  G11B7/1356 ,  G11B7/1362 ,  G11B2007/0006

摘要： Novel polyethersulfone compositions have been discovered which incorporate structural subunits derived from sulfonated bis(halophenyl)sulfones, dihydroxy terphenyls, and/or bis(hydroxyphenyl)pyridines. The sulfonated polyethersulfones show promise as materials for use in polymer electrolyte membranes (PEMs) in fuel cells owing to their high proton conductivities (0.02-0.07 S/cm at 20° C. and 100 percent humidity). In addition, a novel unsulfonated thermoplastic polyethersulfone comprising structural subunits derived from a non-sulfonated bis(halophenyl)sulfone bis4-fluorophenyl)sulfone and 4,4′-dihydroxyphenyl-2,6-pyridine (CAS No. 171820-16-9) is disclosed.

摘要翻译： 已经发现新的聚醚砜组合物掺入衍生自磺化双（卤代苯基）砜，二羟基三联苯和/或双（羟基苯基）吡啶的结构亚单位。 磺化聚醚砜由于其高质子电导率（在20℃和100％湿度下为0.02-0.07S / cm），在燃料电池中用作聚合物电解质膜（PEM）的材料显示出希望。 另外，包含衍生自非磺化双（卤代苯基）砜双-4-氟苯基）砜和4,4'-二羟基苯基-2,6-吡啶（CAS号171820-16-9）的结构亚单位的新型未磺化热塑性聚醚砜， 被披露。

公开(公告)号：US20080114183A1

公开(公告)日：2008-05-15

申请号：US11598947

申请日：2006-11-14

申请人： David Roger Moore ,  Hongyi Zhou ,  Daniel Joseph Brunelle ,  Joyce Hung ,  Hongwei Liu ,  Daniel Steiger

发明人： David Roger Moore ,  Hongyi Zhou ,  Daniel Joseph Brunelle ,  Joyce Hung ,  Hongwei Liu ,  Daniel Steiger

IPC分类号： C07C309/19 ,  C07C309/65

CPC分类号： C07C309/11 ,  C07C309/10 ,  C07C309/24 ,  C07C309/68 ,  C07C317/22 ,  C07C323/66 ,  C07C2603/94 ,  C08G75/23 ,  H01M8/1025 ,  H01M2300/0082

摘要： The invention relates generally to monomers comprising superacidic functional groups. The superacidic functional groups comprise fluorinated sulfonate moieties. Monomers provided by the present invention include dihydroxy aromatic compounds, aromatic diamines, aromatic dicarboxylic acids, aromatic diacarboxylic acid esters, aromatic dithiols, and monomers comprising mixed functionalities, for example monomers comprising an aromatic amine group and an aromatic hydroxyl group. The monomers provided by the present invention are useful in the preparation of novel polymers comprising superacidic functional groups, materials useful in membrane applications. The superacidic functional groups present in the polymer compositions impart excellent proton conductivities. In one embodiment, the present invention provides monomers which may be used to prepare polymers useful as materials for polymer electrolyte fuel cell membranes.

摘要翻译： 本发明一般涉及包含超酸官能团的单体。 超酸性官能团包括氟化磺酸盐部分。 由本发明提供的单体包括二羟基芳族化合物，芳族二胺，芳族二羧酸，芳族二羧酸酯，芳族二硫醇和包含混合官能团的单体，例如包含芳族胺基和芳族羟基的单体。 由本发明提供的单体可用于制备包含超酸性官能团的新型聚合物，可用于膜应用的材料。 存在于聚合物组合物中的超酸性官能团赋予优异的质子电导率。 在一个实施方案中，本发明提供可用于制备用作聚合物电解质燃料电池膜材料的聚合物的单体。

公开(公告)号：US20070142614A1

公开(公告)日：2007-06-21

申请号：US11314877

申请日：2005-12-20

申请人： Joyce Hung ,  Hongyi Zhou ,  Marianne Harmon ,  Daniel Brunelle ,  Hongwei Liu ,  David Moore ,  Daniel Steiger

发明人： Joyce Hung ,  Hongyi Zhou ,  Marianne Harmon ,  Daniel Brunelle ,  Hongwei Liu ,  David Moore ,  Daniel Steiger

IPC分类号： C08G16/00 ,  C08G75/00

CPC分类号： C08G75/23

摘要： Sulfonated block copolymer suitable for use as proton exchange membranes for fuel cells comprise sulfonated polyaryletherketone blocks and polyethersulfone blocks. The sulfonated polyaryletherketone blocks comprise structural units of formula the polyethersulfone blocks comprising structural units of formula wherein R1, R2, R3 and R4 are independently C1-C10 alkyl, C3-C12 cycloalkyl, C6-C14 aryl, allyl, alkenyl, alkoxy, halo, or cyano; Z and Z1 are independently a direct bond or O, S, (CH2)r, (CF2)r, C(CH3)2, C(CF3)2, or a combination thereof; M is H, a metal cation, a non-metallic inorganic cation, an organic cation or a mixture thereof a is 0 or an integer from 1 to 3; b, c and d are independently 0 or an integer from 1 to 4; m and n are independently 0 or 1; and r is an integer from 1 to 5.

摘要翻译： 适用于燃料电池质子交换膜的磺化嵌段共聚物包括磺化聚芳醚酮嵌段和聚醚砜嵌段。 所述磺化聚芳醚酮嵌段包括式的结构单元，所述聚醚砜嵌段包含下式的结构单元：其中R 1，R 2，R 3和R 3， SUP> 4独立地为C 1 -C 10烷基，C 3 -C 12环烷基 C 6 -C 14芳基，烯丙基，烯基，烷氧基，卤素或氰基; Z和Z 1独立地是直接键或O，S，（CH 2）n，（CF 2）2 C（CH 3）2，C（CF 3）2，C（CH 3）2， 或其组合; M为H，金属阳离子，非金属无机阳离子，有机阳离子或其混合物a为0或1〜3的整数; b，c和d独立地为0或1〜4的整数; m和n独立地为0或1; r为1〜5的整数。

公开(公告)号：US20070100131A1

公开(公告)日：2007-05-03

申请号：US11263166

申请日：2005-10-31

申请人： Joyce Hung ,  Hongyi Zhou ,  Daniel Brunelle ,  Marianne Harmon ,  Daniel Steiger ,  Hongwei Liu ,  David Moore

发明人： Joyce Hung ,  Hongyi Zhou ,  Daniel Brunelle ,  Marianne Harmon ,  Daniel Steiger ,  Hongwei Liu ,  David Moore

IPC分类号： C08G75/00

CPC分类号： C08G65/4037 ,  C08G65/4043 ,  C08G65/4056 ,  C08L79/04

摘要： Sulfonated polyethersulfones and polymer compositions comprising sulfonated polyethersulfones and at least one inorganic heteropolyacid are useful as proton exchange membranes for fuel cells. The polyethersulfones include structural units derived from at least one biphenol monomer and a monomer of formula I wherein X is O, S or NR1; Y is N or CR5; R1, R2, R3 and R4 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl or substituted arylalkyl, or R3 and R4, taken together, form a 5- or 6-membered substituted or unsubstituted aliphatic or aromatic ring; R5 is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl or substituted arylalkyl; and L is a direct bond or a divalent aromatic linker containing 6-12 carbons

摘要翻译： 包含磺化聚醚砜和至少一种无机杂多酸的磺化聚醚砜和聚合物组合物可用作燃料电池的质子交换膜。 聚醚砜包括衍生自至少一种联苯酚单体的结构单元和式I的单体，其中X是O，S或NR 1; Y是N或CR 5; R 1，R 2，R 3和R 4独立地是氢，烷基，取代的烷基，芳基， 取代的芳基，烷基芳基，取代的烷基芳基，芳烷基或取代的芳烷基，或R 3和R 4一起形成5-或6-元取代或未取代的脂族基或 芳香环 R 5是氢，烷基，取代的烷基，芳基，取代的芳基，烷基芳基，取代的烷基芳基，芳烷基或取代的芳基烷基; L是直接键或含有6-12个碳原子的二价芳族连接体

公开(公告)号：US20070238856A1

公开(公告)日：2007-10-11

申请号：US11397109

申请日：2006-04-05

申请人： David Moore ,  Hongyi Zhou ,  Christoph Erben ,  Marianne Harmon ,  Joyce Hung ,  Hongwei Liu ,  Daniel Steiger ,  Daniel Brunelle

发明人： David Moore ,  Hongyi Zhou ,  Christoph Erben ,  Marianne Harmon ,  Joyce Hung ,  Hongwei Liu ,  Daniel Steiger ,  Daniel Brunelle

IPC分类号： C08G75/14

CPC分类号： C08G75/23

摘要： Reactive monomers containing the trifluorovinyloxy group may be copolymerized to form polymers useful as membranes, especially polymer electrolyte membranes for fuel cells. The monomers have the formula ((CF2CFO(R1)p)nArX2 wherein Ar is a trivalent, tetravalent or pentavalent, substituted or unsubstituted, aromatic or heteroaromatic, monocyclic or polycyclic group having from 5 to 50 carbon atoms; X is OH, SH, NR2aR2b, F or Br; p is 0 or 1; n is 1, 2 or 3; R1 is substituted or unsubstituted phenyl and R2a and R2b are independently H, C1-C8 alkyl or C1-C8 perfluoroalkyl.

摘要翻译： 含有三氟乙烯基氧基的反应性单体可以共聚以形成可用作膜的聚合物，特别是用于燃料电池的聚合物电解质膜。 这些单体具有式（（CF 2）CFO（R 1））N 2 Ar 2 其中Ar是具有5至50个碳原子的三价，四价或五价，取代或未取代的芳族或杂芳族单环或多环基团; X是OH，SH，NR 2a R F或Br; p为0或1; n为1,2或3; R 1为取代或未取代的苯基且R 2a为H 2 O >和R 2b独立地为H，C 1 -C 8烷基或C 1 -C 3 - 8 全氟烷基。

公开(公告)号：US20060030683A1

公开(公告)日：2006-02-09

申请号：US11193552

申请日：2005-07-29

申请人： David Moore ,  Hongyi Zhou ,  Daniel Steiger ,  Joyce Hung ,  Daniel Brunelle ,  Hongwei Liu ,  Marianne Harmon

发明人： David Moore ,  Hongyi Zhou ,  Daniel Steiger ,  Joyce Hung ,  Daniel Brunelle ,  Hongwei Liu ,  Marianne Harmon

IPC分类号： C08L81/06 ,  C08L81/00

CPC分类号： G11B7/22 ,  G11B7/1356 ,  G11B7/1362 ,  G11B2007/0006

摘要： Novel polyethersulfone compositions have been discovered which incorporate structural subunits derived from sulfonated bis(halophenyl)sulfones, dihydroxy terphenyls, and/or bis(hydroxyphenyl)pyridines. The sulfonated polyethersulfones show promise as materials for use in polymer electrolyte membranes (PEMs) in fuel cells owing to their high proton conductivities (0.02-0.07 S/cm at 20° C. and 100 percent humidity). In addition, a novel unsulfonated thermoplastic polyethersulfone comprising structural subunits derived from a non-sulfonated bis(halophenyl)sulfone bis4-fluorophenyl)sulfone and 4,4′-dihydroxyphenyl-2,6-pyridine (CAS No. 171820-16-9) is disclosed.

摘要翻译： 已经发现新的聚醚砜组合物掺入衍生自磺化双（卤代苯基）砜，二羟基三联苯和/或双（羟基苯基）吡啶的结构亚单位。 磺化聚醚砜由于其高质子电导率（在20℃和100％湿度下为0.02-0.07S / cm），在燃料电池中用作聚合物电解质膜（PEM）的材料显示出希望。 另外，包含衍生自非磺化双（卤代苯基）砜双-4-氟苯基）砜和4,4'-二羟基苯基-2,6-吡啶（CAS号171820-16-9）的结构亚单位的新型未磺化热塑性聚醚砜， 被披露。

公开(公告)号：US08623971B2

公开(公告)日：2014-01-07

申请号：US13361684

申请日：2012-01-30

申请人： Daniel Joseph Brunelle ,  Daniel Steiger

发明人： Daniel Joseph Brunelle ,  Daniel Steiger

IPC分类号： C08G75/23 ,  C08F283/06 ,  C08L81/00

CPC分类号： C08G75/23 ,  C08L81/06

摘要： Polyethersulfones having Tg greater than about 225° C. and a notched Izod value greater than about 1 ft-lb/in, as measured by ASTM D256, comprise from about 5 mol % to less than about 40 mol % structural units of formula 1; and from greater than about 60 mol % to about 95 mol % structural units of formula 2 wherein R1, R2, and R3 are independently at each occurrence a halogen atom, a nitro group, a cyano group, a C1-C12aliphatic radical, C3-C12cycloaliphatic radical, or a C3-C12aromatic radical; n, m, q are independently at each occurrence integers from 0 to 4; and Q is a C3-C20cycloaliphatic radical, or a C3-C20aromatic radical.

摘要翻译： Tg大于约225℃的聚醚砜和通过ASTM D256测量的大于约1ft-lb / in的缺口伊佐德值包含约5mol％至小于约40mol％的式1结构单元; 和大于约60mol％至约95mol％的式2的结构单元，其中R 1，R 2和R 3在每次出现时独立地为卤素原子，硝基，氰基，C 1 -C 12脂族基，C 3 -C 12脂族基， C 12环脂族基或C 3 -C 12芳族基; n，m，q各自独立地为0至4的整数; Q为C 3 -C 20环脂族基或C 3 -C 20芳族基。