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1. 发明授权

US4629798A Electrically conductive pyrrole polymers and process of preparing the same 失效
标题翻译：导电吡咯聚合物及其制备方法
公开(公告)号：US4629798A
公开(公告)日：1986-12-16
申请号：US767209
申请日：1985-08-19
申请人： Lee Traynor
发明人： Lee Traynor
IPC分类号： C08G61/12 , H01B1/12 , H01M4/60 , C07D207/30 , C07D401/12
CPC分类号： H01M4/60 , C08G61/124 , H01B1/127
摘要： Organic polymers which are "hydroxyphenyl-substituted" and "ether-substituted" polypyrroles ("PP") linked through N-adjacent C atoms, are disclosed which are compactable, extrudable and are also electrical conductors. When such PPs are prepared by electrochemical deposition with an appropriate electrolyte, they are also soluble in commonly available solvents, provided at least one of the 3- or 4-positions of the pyrrole nucleus is substituted with a substituent having either a hydroxyphenyl, or an ether structure. By choice of the hydroxyphenyl and/or ether substituent on one of the substitutable positions (3- or 4-) of the pyrrole nucleus, or both, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm.A method is disclosed for preparing an ether-substituted pyrrole comprising reacting a non-Michael acceptor selected from the group consisting of esters, ketones and nitriles having vinylene carbon atoms, with tosylmethylisocyanide, in the presence of a solvent, so as to form a hydroxyphenyl-substituted or an ether-substituted pyrrole directly without substituting the pyrrole ring in the 2- and 5-positions.
摘要翻译：公开了通过N相邻的C原子连接的“羟基苯基取代的”和“醚取代的”聚吡咯（“PP”）的有机聚合物，其是可压缩的，可挤出的并且也是电导体。当这样的PP通过用适当的电解质的电化学沉积制备时，它们也可溶于常用的溶剂中，只要吡咯核的3-或4-位中的至少一个被具有羟基苯基或醚结构。通过选择吡咯核的一个可取代位置（3-或4-）或两者，可以将PP定制为使用导电性范围为约 10-5至约10-2S / cm，或导电率在约10-2至约102S / cm范围内的相对较好的导体。公开了一种制备醚取代的吡咯的方法，包括在溶剂存在下使选自酯，酮和具有亚乙烯基碳原子的腈的非迈克尔受体与甲苯磺酰基甲基异氰化物反应，从而形成羟基苯基 - 取代的或醚取代的吡咯，而不用2-和5-位的吡咯环。

2. 发明授权

US4543402A Electrically conductive pyrrole polymers 失效
标题翻译：导电吡咯聚合物
公开(公告)号：US4543402A
公开(公告)日：1985-09-24
申请号：US486161
申请日：1983-04-18
申请人： Lee Traynor
发明人： Lee Traynor
IPC分类号： C08G61/12 , H01B1/12 , H01M4/60 , C08F126/06
CPC分类号： C08G61/124 , H01B1/127 , H01M4/60
摘要： Organic polymers which are "hydroxyphenyl-substituted" and "ether-substituted" polypyrroles ("PP") linked through N-adjacent C atoms, are disclosed which are compactable, extrudable and are also electrical conductors. When such PPs are prepared by electrochemical deposition with an appropriate electrolyte, they are also soluble in commonly available solvents, provided at least one of the 3- or 4- positions of the pyrrole nucleus is substituted with a substituent having either a hydroxyphenyl, or an ether structure. By choice of the hydroxyphenyl and/or ether substituent on one of the substitutable positions (3- or 4-) of the pyrrole nucleus, or both, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm. A method is disclosed for preparing an ether-substituted pyrrole comprising reacting a non-Michael acceptor selected from the group consisting of esters, ketones and nitriles having vinylene carbon atoms, with tosylmethylisocyanide, in the presence of a solvent, so as to form a hydroxyphenyl-substituted or an ether-substituted pyrrole directly without substituting the pyrrole ring in the 2- and 5- positions.
摘要翻译：公开了通过N相邻的C原子连接的“羟基苯基取代的”和“醚取代的”聚吡咯（“PP”）的有机聚合物，其是可压缩的，可挤出的并且也是电导体。当这样的PP通过用适当的电解质进行电化学沉积制备时，它们也可溶于常用的溶剂中，只要吡咯核的3-或4-位的至少一个被具有羟苯基或醚结构。通过选择吡咯核的一个可取代位置（3-或4-）或两者，可以将PP定制为使用导电性范围为约 10-5至约10-2S / cm，或导电率在约10-2至约102S / cm范围内的相对较好的导体。公开了一种制备醚取代的吡咯的方法，包括在溶剂存在下使选自酯，酮和具有亚乙烯基碳原子的腈的非迈克尔受体与甲苯磺酰基甲基异氰化物反应，从而形成羟基苯基取代或醚取代的吡咯，而不用2-和5-位置的吡咯环。

3. 发明授权

US4487667A Polymethylene pyrroles and electrically conductive polymers thereof 失效
标题翻译：聚亚甲基吡咯及其导电聚合物
公开(公告)号：US4487667A
公开(公告)日：1984-12-11
申请号：US494752
申请日：1983-05-16
申请人： Lee Traynor
发明人： Lee Traynor
IPC分类号： C08G61/12 , H01B1/12 , C25B1/00
CPC分类号： H01B1/127 , C08G61/124
摘要： Cycloalk-2-enes and cycloalk-2-ene-dienes are found to be Michael acceptors which react with tosylmethylisocyanide to form bicyclo fused-ring compounds. A wide variety of substituents may be introduced on the alkylene ring with the aid of the carbonyl group(s) on the fused-ring compound.These carbonyl-containing bicyclo fused-ring compounds may be reduced to provide monomers which may be electrodeposited as substituted polypyrroles ("PP") which are electrically conductive, compactable and extrudable organic polymers. By choice of substituents on the alkylene ring which bridges the 3- and 4- carbon atoms of the pyrrole ring, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm.A method is disclosed for preparing a polymethylene-substituted pyrrole comprising reacting a cyclic mono- or di-ketone Michael acceptor selected from the group consisting of cycloalk-2-enes and cycloalk-2-dienes, with tosylmethylisocyanide, in the presence of a solvent, so as to form an azabicycloalkylene(di)one, directly, without substituting the N-adjacent carbon atoms on the pyrrole ring.
摘要翻译：发现环烯-2-烯和环烯-2-烯二烯是与甲苯磺酰甲基异氰化物反应形成双环稠环化合物的迈克尔受体。借助于稠环化合物上的羰基，可以在亚烷基环上引入多种取代基。这些含羰基的双环稠环化合物可以被还原以提供可以作为导电，可压缩和可挤出的有机聚合物的取代聚吡咯（“PP”）电沉积的单体。通过选择桥接吡咯环的3-和4-碳原子的亚烷基环上的取代基，PP可以被定制用作导电率在约10-5至约10-2范围内的半导体 S / cm，或导电率在约10-2至约102S / cm范围内的相对较好的导体。公开了一种制备聚亚甲基取代的吡咯的方法，其包括在溶剂存在下使选自环烷-2-烯和环烯-2-二烯的环状单酮或二酮迈克尔受体与甲苯磺酰基甲基异氰化物反应，以直接形成氮杂二环烷基（二），而不用吡咯环上的N-相邻的碳原子。

4. 发明授权

US4663402A Non-catalytic process for the preparation of difunctionalized polyarylene polyethers 失效
标题翻译：用于制备双官能化聚亚芳基聚醚的非催化方法
公开(公告)号：US4663402A
公开(公告)日：1987-05-05
申请号：US814749
申请日：1985-12-30
申请人： Virgil Percec , Gary S. Huvard , Floyd L. Ramp , Lee Traynor
发明人： Virgil Percec , Gary S. Huvard , Floyd L. Ramp , Lee Traynor
IPC分类号： C08G65/48 , C08G75/02 , C08G75/23
CPC分类号： C08G75/02 , C08G65/48
摘要： A non-catalytic process converts oligomers of polyarylene polyethers (PAPE) having a mol wt Mn in the range from 1000 to about 10,000 to difunctionalized oligomers so as, in the first instance, to provide a reactive double bond (for example, a vinylbenzyl group) at each end of the PAPE; and, in the second instance to provide a triple bond (benzylethynyl group) at each end of the PAPE. The solubility of intermediate bisphenolates of (i) a dihydric phenol, and of (ii) the PAPE oligomer in particular solvents which allow (a) water of reaction to be removed without being degraded, and (b) essentially complete end-capping of the oligomer chains with vinyl chain ends, are the keys to the novel process. The PAPE most preferably has a repeating unit which is the residuum of two dihydric phenols or thiophenols ("DHP") linked through a C.dbd.O, --S--S--, or --SO.sub.2 - group, or a Si or C atom, and/or ether O, or thioether S atoms. The preferred repeating unit is formed by reaction of a DHP such as bisphenol A (BPA) with a halogenated DHP such as dichlorophenyl sulfone (DCPS) so as to provide an alternating configuration. The repeating unit may also include a linking residue of a reactive solvent which residue provides chain extension in the backbone. An oligomer which is a homopolymer having a repeating unit in which at least four benzenoid rings are connected through ether O atoms, may also be difunctionalized. In particular, .alpha..omega.-di(phenol)aromatic polyether sulfone oligomers ("APS") are esterified so as to have terminal methacrylyl groups; and, etherified so as to have styryl end groups which are thermally crosslinkable.
摘要翻译：非催化方法将具有1000至10,000的mol wt＆Upbar＆M的聚亚芳基聚醚（PAPE）的低聚物转化为二官能化低聚物，以便首先提供反应性双键（例如，乙烯基苄基组）; 并且在第二种情况下在PAPE的每一端提供三键（苄基乙炔基）。（i）二元酚和（ii）PAPE低聚物的中间体双酚体在特定溶剂中的溶解度，其允许（a）反应水被除去而不被降解，和（b）基本上完全封端的具有乙烯基链末端的低聚物链是新型方法的关键。 PAPE最优选具有重复单元，其是通过C = O，-SS-或-SO 2 - 基团或Si或C原子连接的两个二元酚或苯硫酚（“DHP”）的残基，和/或醚O或硫醚S原子。优选的重复单元通过DHP如双酚A（BPA）与卤代DHP如二氯苯基砜（DCPS）的反应形成，以提供交替配置。重复单元还可以包括反应性溶剂的连接残基，该残基在骨架中提供链延伸。作为具有通过醚O原子连接至少四个苯环的重复单元的均聚物的低聚物也可以是双官能化的。特别地，αω-二（苯酚）芳族聚醚砜低聚物（“APS”）被酯化以具有末端甲基丙烯酰基; 并进行醚化以具有可热交联的苯乙烯基端基。

5. 发明授权

US4602090A Polymethylene pyrroles 失效
标题翻译：聚亚甲基吡咯
公开(公告)号：US4602090A
公开(公告)日：1986-07-22
申请号：US679846
申请日：1984-12-10
申请人： Lee Traynor
发明人： Lee Traynor
IPC分类号： C25B3/10 , H01B1/12 , C07D401/06 , C07D209/52
CPC分类号： C25B3/10 , H01B1/127
摘要： Cycloalk-2-enes and cycloalk-2-ene-dienes are found to be Michael acceptors which react with tosylmethylisocyanide to form bicyclo fused-ring compounds. A wide variety of substituents may be introduced on the alkylene ring with the aid of the carbonyl group(s) on the fused-ring compound.These carbonyl-containing bicyclo fused-ring compounds may be reduced to provide monomers which may be electrodeposited as substituted polypyrroles ("PP") which are electrically conductive, compactable and extrudable organic polymers. By choice of substituents on the alkylene ring which bridges the 3- and 4-carbon atoms of the pyrrole ring, the PP may be tailored for use either as a semiconductor having a conductivity in the range from about 10.sup.-5 to about 10.sup.-2 S/cm, or a relatively good conductor having a conductivity in the range from about 10.sup.-2 to about 10.sup.2 S/cm.A method is disclosed for preparing a polymethylene-substituted pyrrole comprising reacting a cyclic mono- or di-ketone Michael acceptor selected from the group consisting of cycloalk-2-enes and cycloalk-2-dienes, with tosylmethylisocyanide, in the presence of a solvent, so as to form an azabicycloalkylene(di)one, directly, without substituting the N-adjacent carbon atoms on the pyrrole ring.
摘要翻译：发现环烯-2-烯和环烯-2-烯二烯是与甲苯磺酰甲基异氰化物反应形成双环稠环化合物的迈克尔受体。借助于稠环化合物上的羰基，可以在亚烷基环上引入多种取代基。这些含羰基的双环稠环化合物可以被还原以提供可以作为导电，可压缩和可挤出的有机聚合物的取代聚吡咯（“PP”）电沉积的单体。通过选择桥接吡咯环的3-和4-碳原子的亚烷基环上的取代基，PP可以被定制用作导电率在约10-5至约10-2范围内的半导体 S / cm，或导电率在约10-2至约102S / cm范围内的相对较好的导体。公开了一种制备聚亚甲基取代的吡咯的方法，其包括在溶剂存在下使选自环烷-2-烯和环烯-2-二烯的环状单酮或二酮迈克尔受体与甲苯磺酰基甲基异氰化物反应，以直接形成氮杂二环烷基（二），而不用吡咯环上的N-相邻的碳原子。

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