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1. 发明授权

US06958192B2 Polyimides from 2,3,3′,4′-biphenyltetracarboxylic dianhydride and aromatic diamines 失效
标题翻译：来自2,3,3'，4'-联苯四羧酸二酐和芳族二胺的聚酰亚胺
公开(公告)号：US06958192B2
公开(公告)日：2005-10-25
申请号：US10414562
申请日：2003-04-07
申请人： Paul M. Hergenrother , Joseph G. Smith, Jr. , John W. Connell , Kent A. Watson
发明人： Paul M. Hergenrother , Joseph G. Smith, Jr. , John W. Connell , Kent A. Watson
IPC分类号： C08G73/10 , B32B27/00
CPC分类号： C08G73/1057 , C08G73/1039 , C08G73/105 , Y10T428/31721
摘要： The present invention relates generally to polyimides. It relates particularly to novel polyimides prepared from 2,3,3′,4′-biphenyltetracarboxylic dianhydride and aromatic diamines. These novel polyimides have low color, good solubility, high thermal emissivity, low solar absorptivity and high tensile strength.
摘要翻译：本发明一般涉及聚酰亚胺。特别涉及由2,3,3'，4'-联苯四羧酸二酐和芳族二胺制备的新型聚酰亚胺。这些新型聚酰亚胺具有颜色低，溶解性好，热发射率高，太阳吸收率低，拉伸强度高。

2. 发明授权

US5412059A Polybenzimidazoles via aromatic nucleophilic displacement 失效
标题翻译：聚苯并咪唑通过芳族亲核取代
公开(公告)号：US5412059A
公开(公告)日：1995-05-02
申请号：US45335
申请日：1993-04-05
申请人： John W. Connell , Paul M. Hergenrother , Joseph G. Smith, Jr.
发明人： John W. Connell , Paul M. Hergenrother , Joseph G. Smith, Jr.
IPC分类号： C08G73/18 , C09J179/04 , C08G63/00 , C08G8/02
CPC分类号： C08G73/18 , C09J179/04 , Y10S526/935 , Y10T428/31504
摘要： Novel molecular weight controlled and endcapped polybenzimidazoles (PBI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenylbenzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The PBI are endcapped with mono(hydroxyphenyl)benzimidazoles. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. Mono(hydroxyphenyl)benzimidazoles are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic (o-diamine)s in diphenylsulfone. Molecular weight controlled and endcapped PBI of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties.
摘要翻译：通过二（羟基苯基苯并咪唑）单体与活性芳族二卤化物或活性芳族二硝基化合物的芳族亲核置换反应制备新型分子量控制和封端的聚苯并咪唑（PBI）。 PBI被单（羟基苯基）苯并咪唑封端。聚合在极性非质子溶剂如N-甲基-2-吡咯烷酮或N，N-二甲基乙酰胺中，使用碱金属碱如碳酸钾，在氮气下在升高的温度下进行。通过苯基-4-羟基苯甲酸酯与二苯砜中的芳族（邻二胺）反应合成单（羟基苯基）苯并咪唑。制备新化学结构的分子量控制和封端的PBI，其表现出物理和机械性质的有利组合。

3. 发明授权

US5689004A Diamines containing pendent phenylethynyl groups 失效
标题翻译：含有侧基苯乙炔基的二胺
公开(公告)号：US5689004A
公开(公告)日：1997-11-18
申请号：US747472
申请日：1996-11-12
申请人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
发明人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
IPC分类号： C08J5/18 , B32B27/34 , C07C217/90 , C07C225/22 , C08G73/10 , C09J179/08 , C07C317/36
CPC分类号： C07C217/90 , C07C225/22 , C08G73/101 , C08G73/1042 , C08G73/1078 , C09J179/08 , Y10S526/935 , Y10T428/31504 , Y10T428/31721
摘要： Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone and N,N-dimethylacetamide under nitrogen at room temperature. The amide acid oligomers or co-oligomers are subsequently cyclodehydrated either thermally or chemically to the corresponding imide oligomers. The polymers and copolymers prepared from these materials exhibit a unique and unexpected combination of properties that includes higher glass transition temperatures after curing and higher retention of neat resin, adhesive and carbon fiber reinforced mechanical properties at temperatures up to 204.degree. C. under wet conditions without sacrificing melt flow behavior and processability as compared to similar materials. These materials are useful as adhesives, coatings, films, moldings and composite matrices.
摘要翻译：已经通过将含有侧链苯基乙炔基的前体酰胺酸低聚物或共低聚物环状脱水并用非反应性或苯基乙炔基封端而制备了含有侧链苯基乙炔基（PEPI）和封端有非反应性或苯基乙炔基的受控分子量酰亚胺低聚物和共低聚物。胺封端的酰胺酸低聚物或共低聚物由二酐与过量的二胺和含有侧基苯基乙炔基的二胺的反应制备，随后用苯基乙炔基邻苯二甲酸酐或单官能酐封端。酸酐封端的酰胺酸低聚物和共低聚物由二胺和含有侧基苯乙炔基的二胺与过量的二酐的反应制备，随后用苯乙炔胺或单官能胺封端。聚合在极性非质子溶剂如N-甲基-2-吡咯烷酮和N，N-二甲基乙酰胺中，在室温下在氮气下进行。酰胺酸低聚物或共低聚物随后热或化学地与相应的酰亚胺低聚物环化脱水。由这些材料制备的聚合物和共聚物表现出独特和意想不到的性能组合，其包括固化后较高的玻璃化转变温度和更高的纯树脂保留率，粘合剂和碳纤维增强的机械性能在高达204℃的温度下在潮湿条件下没有与类似材料相比，牺牲熔体流动行为和加工性能。这些材料可用作粘合剂，涂料，薄膜，模制品和复合基质。

4. 发明授权

US5410012A Poly(N-arylenebenzimidazoles) via aromatic nucleophilic displacement 失效
标题翻译：聚（N-亚芳基苯并咪唑）通过芳族亲核取代
公开(公告)号：US5410012A
公开(公告)日：1995-04-25
申请号：US45339
申请日：1993-03-05
申请人： John W. Connell , Paul M. Hergenrother , Joseph G. Smith, Jr.
发明人： John W. Connell , Paul M. Hergenrother , Joseph G. Smith, Jr.
IPC分类号： C08G73/18
CPC分类号： C08G73/18
摘要： Novel poly(N-arylenebenzimidazole)s (PNABIs) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl-N-arylene benzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl-N-arylenebenzimidazole) monomers are synthesized by reacting phenyl-4-hydroxybenzoate with bis(2-aminoanilino)arylenes in diphenylsulfone. Moderate molecular weight PNABIs of new chemical structures were prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyl-N-arylenebenzimidazole)s permits a more economical and easier way to prepare PNABIs than previous routes.
摘要翻译：通过新型二（羟基苯基-N-亚芳基苯并咪唑）单体与活性芳族二卤化物或活性芳族二硝基化合物的芳族亲核取代反应制备新型聚（N-亚芳基苯并咪唑）（PNABI）。聚合在极性非质子溶剂如N-甲基-2-吡咯烷酮或N，N-二甲基乙酰胺中，使用碱金属碱如碳酸钾，在氮气下在升高的温度下进行。二（羟基苯基-N-亚芳基苯并咪唑）单体通过苯基-4-羟基苯甲酸酯与二（2-氨基苯胺基）亚芳基在二苯基砜中反应合成。制备中等分子量的新化学结构的PNABI，其表现出物理和机械性能的有利组合。新型二（羟基苯基-N-亚芳基苯并咪唑）的使用允许比以前的路线更经济和更容易地制备PNABI的方法。

5. 发明授权

US06841652B2 Space environmentally durable polyimides and copolyimides 失效
标题翻译：空间环保的聚酰亚胺和共聚酰亚胺
公开(公告)号：US06841652B2
公开(公告)日：2005-01-11
申请号：US10095340
申请日：2002-03-08
申请人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother , Kent A. Watson , Craig M. Thompson
发明人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother , Kent A. Watson , Craig M. Thompson
IPC分类号： C08G73/10 , C08G69/26 , C08G69/72
CPC分类号： C08G73/1071 , C08G73/10 , C08G73/1014 , C08G73/1039 , C08G73/1057 , C08G73/1067
摘要： Polyimides displaying low color in thin films, atomic oxygen resistance, vacuum ultraviolet radiation resistance, solubility in organic solvents in the imide form, high glass transition (Tg) temperatures, and high thermal stability are provided. The poly(amide acid)s, copoly(amide acid)s, polyimides and copolyimides are prepared by the reaction of stoichiometric ratios of an aromatic dianhydride with diamines which contain phenylphosphine oxide groups in polar aprotic solvents. Controlled molecular weight oligomeric (amide acid)s and imides can be prepared by offsetting the stoichiometry according to the Carothers equation using excess diamine and endcapping with aromatic anhydrides The polyimide materials can be processed into various material forms such as thin films, fibers, foams, threads, adhesive film, coatings, dry powders, and fiber coated prepreg, and uses include thin film membranes on antennas, second-surface mirrors, thermal optical coatings, and multi-layer thermal insulation (MLI) blanket materials.
摘要翻译：提供在薄膜中显示低色的聚酰亚胺，原子氧电阻，真空紫外线辐射抗性，在酰亚胺形式的有机溶剂中的溶解度，高玻璃化转变温度和高热稳定性。聚（酰胺酸），共聚（酰胺酸），聚酰亚胺和共聚酰亚胺通过芳族二酐与极性非质子溶剂中含有苯基氧化膦基团的二胺的化学计量比的反应来制备。控制分子量低聚（酰胺酸）和酰亚胺可以通过使用过量的二胺和用芳族酸酐封端根据Carothers方程来抵消化学计量来制备。聚酰亚胺材料可以加工成各种材料形式，例如薄膜，纤维，泡沫，螺纹，粘合剂膜，涂料，干粉和纤维涂层预浸料，并且包括天线上的薄膜膜，第二表面反射镜，热光学涂层和多层保温（MLI）覆盖材料。

6. 发明授权

US06350817B1 Phenylethynyl containing reactive additives 失效
标题翻译：苯基乙炔基含反应性添加剂
公开(公告)号：US06350817B1
公开(公告)日：2002-02-26
申请号：US09290295
申请日：1999-04-13
申请人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
发明人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
IPC分类号： C08F3800
CPC分类号： C08G73/101 , C08F251/00 , C08F281/00 , C08F290/14 , C08G73/10
摘要： Phenylethynyl containing reactive additives were prepared from aromatic diamines containing phenylethynyl groups and various ratios of phthalic anhydride and 4-phenylethynylphthalic anhydride in glacial acetic acid to form the imide in one step or in N-methyl-2-pyrrolidinone to form the amide acid intermediate. The reactive additives were mixed in various amounts (10% to 90%) with oligomers containing either terminal or pendent phenylethynyl groups (or both) to reduce the melt viscosity and thereby enhance processability. Upon thermal cure, the additives react and become chemically incorporated into the matrix and effect an increase in crosslink density relative to that of the host resin. This resultant increase in crosslink density has advantageous consequences on the cured resin properties such as higher glass transition temperature and higher modulus as compared to that of the host resin.
摘要翻译：含苯基乙炔基的反应性添加剂由含苯基乙炔基的芳族二胺和各种比例的邻苯二甲酸酐和4-苯基乙炔基邻苯二甲酸酐在冰醋酸中制备，在一步中形成酰亚胺或在N-甲基-2-吡咯烷酮中形成酰胺酸中间体。将反应性添加剂与含有末端或侧基苯基乙炔基（或两者）的低聚物以各种量（10％至90％）混合，以降低熔融粘度，从而提高加工性。热固化后，添加剂反应并化学掺入基质中，相对于主体树脂的交联密度增加。这种交联密度的增加对固化树脂性能如与主体树脂相比具有更高的玻璃化转变温度和更高的模量是有利的。

7. 发明授权

US5270432A Polybenzoxazole via aromatic nucleophilic displacement 失效
标题翻译：聚苯并恶唑通过芳族亲核取代
公开(公告)号：US5270432A
公开(公告)日：1993-12-14
申请号：US867864
申请日：1992-04-10
申请人： Paul M. Hergenrother , John W. Connell , Joseph G. Smith, Jr.
发明人： Paul M. Hergenrother , John W. Connell , Joseph G. Smith, Jr.
IPC分类号： C08G73/22 , C08G73/08
CPC分类号： C08G73/22
摘要： Polybenzoxazoles (PBO) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl)benzoxazole monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents, such as N-methylpyrrolidine or N,N-dimethylacetamide, using alkali metal bases, such as potassium carbonate, at elevated temperatures under nitrogen. The novel di(hydroxyphenyl)benzoxazole monomers are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic bis(o-aminophenol)s in the melt. High molecular weight PBO of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyl)benzoxazoles permits a more economical and easier way to prepare PBO than previous routes.
摘要翻译：通过新型二（羟基苯基）苯并唑单体与活性芳族二卤化物或活性芳族二硝基化合物的芳族亲核取代反应制备聚苯并恶唑（PBO）。在极性非质子溶剂如N-甲基吡咯烷或N，N-二甲基乙酰胺中，使用碱金属碱如碳酸钾，在氮气升高下进行聚合。新型二（羟基苯基）苯并唑单体通过苯基-4-羟基苯甲酸酯与芳族双（邻氨基苯酚）在熔体中反应而合成。制备新化学结构的高分子量PBO，其表现出物理和机械性能的有利组合。使用新的二（羟基苯基）苯并恶唑可以比以前的路线更经济，更容易地制备PBO。

8. 发明授权

US07109287B2 Space environmentally durable polyimides and copolyimides 失效
标题翻译：空间环保的聚酰亚胺和共聚酰亚胺
公开(公告)号：US07109287B2
公开(公告)日：2006-09-19
申请号：US10988407
申请日：2004-11-08
申请人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother , Kent A. Watson , Craig M. Thompson
发明人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother , Kent A. Watson , Craig M. Thompson
IPC分类号： C08G69/26
CPC分类号： C08G73/1071 , C08G73/10 , C08G73/1014 , C08G73/1039 , C08G73/1057 , C08G73/1067
摘要： Polyimides displaying low color in thin films, atomic oxygen resistance, vacuum ultraviolet radiation resistance, solubility in organic solvents in the imide form, high glass transition (Tg) temperatures, and high thermal stability are provided. The poly(amide acid)s, copoly(amide acid)s, polyimides and copolyimides are prepared by the reaction of stoichiometric ratios of an aromatic dianhydride with diamines which contain phenylphosphine oxide groups in polar aprotic solvents. Controlled molecular weight oligomeric (amide acid)s and imides can be prepared by offsetting the stoichiometry according to the Carothers equation using excess diamine and endcapping with aromatic anhydrides. The polyimide materials can be processed into various material forms such as thin films, fibers, foams, threads, adhesive film, coatings, dry powders, and fiber coated prepreg, and uses include thin film membranes on antennas, second-surface mirrors, thermal optical coatings, and multi-layer thermal insulation (MLI) blanket materials.
摘要翻译：提供在薄膜中显示低色的聚酰亚胺，原子氧电阻，真空紫外线辐射抗性，在酰亚胺形式的有机溶剂中的溶解度，高玻璃化转变温度和高热稳定性。聚（酰胺酸），共聚（酰胺酸），聚酰亚胺和共聚酰亚胺通过芳族二酐与极性非质子溶剂中含有苯基氧化膦基团的二胺的化学计量比的反应来制备。控制分子量的低聚（酰胺酸）和酰亚胺可以通过使用过量的二胺和用芳族酸酐封端根据Carothers方程来抵消化学计量来制备。聚酰亚胺材料可以加工成各种材料形式，如薄膜，纤维，泡沫，线，粘合膜，涂料，干粉和纤维涂层预浸料，其中包括天线薄膜，第二面反光镜，热光学涂层和多层保温（MLI）覆层材料。

9. 发明授权

US6124035A High temperature transfer molding resins 失效
标题翻译：高温传递模塑树脂
公开(公告)号：US6124035A
公开(公告)日：2000-09-26
申请号：US310686
申请日：1999-04-13
申请人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
发明人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
IPC分类号： C07D209/48 , C08G73/12 , C08G8/02 , C08G73/10
CPC分类号： C07D209/48 , C08G73/122 , Y10T428/31504 , Y10T428/31721 , Y10T428/31942
摘要： High temperature resins containing phenylethynyl groups that are processable by transfer molding have been prepared. These phenylethynyl containing oligomers were prepared from aromatic diamines containing phenylethynyl groups and various ratios of phthalic anhydride and 4-phenylethynlphthalic anhydride in glacial acetic acid to form a mixture of imide compounds in one step. This synthetic approach is advantageous since the products are a mixture of compounds and consequently exhibit a relatively low melting temperature. In addition, these materials exhibit low melt viscosities which are stable for several hours at 210-275.degree. C., and since the thermal reaction of the phenylethynyl group does not occur to any appreciable extent at temperatures below 300.degree. C., these materials have a broad processing window. Upon thermal cure at .about.300-350.degree. C., the phenylethynyl groups react to provide a crosslinked resin system. These new materials exhibit excellent properties and are potentially useful as adhesives, coatings, films, moldings and composite matrices.
摘要翻译：已经制备了可通过传递模塑加工的含苯基乙炔基的高温树脂。这些含苯基乙炔基的低聚物由含苯基乙炔基的芳族二胺和各种比例的邻苯二甲酸酐和4-苯基邻苯二甲酸酐在冰醋酸中制备，从而在一个步骤中形成酰亚胺化合物的混合物。这种合成方法是有利的，因为产物是化合物的混合物，因此表现出相对较低的熔融温度。此外，这些材料表现出低熔融粘度，其在210-275℃下稳定数小时，并且由于苯乙炔基的热反应在低于300℃的温度下不会发生任何可察觉的程度，所以这些材料具有一个广泛的处理窗口。在300-350℃的温度下热固化时，苯基乙炔基反应以提供交联的树脂体系。这些新材料表现出优异的性能，并且可能用作粘合剂，涂料，薄膜，模制品和复合基质。

10. 发明授权

US5606014A Imide oligomers and co-oligomers containing pendent phenylethynyl groups and polymers therefrom 失效
标题翻译：含有侧链苯基乙炔基和其聚合物的酰亚胺低聚物和共低聚物
公开(公告)号：US5606014A
公开(公告)日：1997-02-25
申请号：US511422
申请日：1995-08-04
申请人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
发明人： John W. Connell , Joseph G. Smith, Jr. , Paul M. Hergenrother
IPC分类号： C08J5/18 , B32B27/34 , C07C217/90 , C07C225/22 , C08G73/10 , C09J179/08 , C08G69/26
CPC分类号： C07C217/90 , C07C225/22 , C08G73/101 , C08G73/1042 , C08G73/1078 , C09J179/08 , Y10S526/935 , Y10T428/31504 , Y10T428/31721
摘要： Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as under nitrogen at room temperature. The amide acid oligomers or co-oligomers are subsequently cyclodehydrated to the corresponding imide oligomers. The polymers and copolymers prepared from these materials exhibit a unique and unexpected combination of properties.
摘要翻译：已经通过将含有侧链苯基乙炔基的前体酰胺酸低聚物或共低聚物环状脱水并用非反应性或苯基乙炔基封端而制备了含有侧链苯基乙炔基（PEPI）和封端有非反应性或苯基乙炔基的受控分子量酰亚胺低聚物和共低聚物。胺封端的酰胺酸低聚物或共低聚物由二酐与过量的二胺和含有侧基苯基乙炔基的二胺的反应制备，随后用苯基乙炔基邻苯二甲酸酐或单官能酐封端。酸酐封端的酰胺酸低聚物和共低聚物由二胺和含有侧基苯乙炔基的二胺与过量的二酐的反应制备，随后用苯乙炔胺或单官能胺封端。聚合在极性非质子溶剂如氮气下在室温下进行。酰胺酸低聚物或共低聚物随后环化成相应的酰亚胺低聚物。由这些材料制备的聚合物和共聚物表现出独特且意想不到的性能组合。

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