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1. 发明授权

US07943712B2 Catalyst system for synthesizing amine functionalized rubbery polymers having a high trans microstructure 有权
标题翻译：用于合成具有高反向显微组织的胺官能化橡胶状聚合物的催化剂体系
公开(公告)号：US07943712B2
公开(公告)日：2011-05-17
申请号：US11617361
申请日：2006-12-28
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Laurie Elizabeth Austin , Chad Aaron Jasiunas , Steven Kristofer Henning
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Laurie Elizabeth Austin , Chad Aaron Jasiunas , Steven Kristofer Henning
IPC分类号： C08F4/50 , C08F2/06 , C07F7/08
CPC分类号： C08F36/04 , C08F4/48 , C08F4/54
摘要： The present invention is directed to a catalyst system for synthesizing rubbery polymers, such as polybutadiene rubber, styrene-butadiene rubber, isoprene-butadiene rubber, or styrene-isoprene-butadiene rubber, that are amine functionalized and have a high trans microstructure. The catalyst system, in one embodiment, includes (a) an organolithium amine compound, (b) a group IIa metal salt of an amino glycol or a glycol ether, (c) an organoaluminum compound, and optionally (d) an amine compound. The amine functionalized rubbery polymers can be utilized in tire tread rubbers where the rubbery polymers may provide desirable wear properties without substantially sacrificing other performance characteristic(s), e.g., traction properties.
摘要翻译：本发明涉及一种用于合成胺官能化并具有高反相微观结构的橡胶状聚合物如聚丁二烯橡胶，苯乙烯 - 丁二烯橡胶，异戊二烯 - 丁二烯橡胶或苯乙烯 - 异戊二烯 - 丁二烯橡胶的催化剂体系。在一个实施方案中，催化剂体系包括（a）有机锂胺化合物，（b）氨基二醇或二醇醚的IIa族金属盐，（c）有机铝化合物和任选的（d）胺化合物。胺官能化橡胶状聚合物可用于轮胎胎面橡胶中，其中橡胶状聚合物可提供期望的耐磨性，而基本上不会牺牲其它性能特征，例如牵引性能。

2. 发明授权

US07714089B2 Functionalized monomers and functionalized rubbery polymers made therewith 有权
标题翻译：官能化单体和由其制备的官能化橡胶聚合物
公开(公告)号：US07714089B2
公开(公告)日：2010-05-11
申请号：US11955453
申请日：2007-12-13
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Leh-Yeh Hsu, legal representative , Shingo Futamura , Joe Zhou , Chad Aaron Jasiunas
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Shingo Futamura , Joe Zhou , Chad Aaron Jasiunas
IPC分类号： C08F236/14 , C08F226/06 , C08F230/02 , C07C323/25 , C07F7/10 , C08F2/22
CPC分类号： C08F236/14 , C07C323/25 , C07F7/1804 , C07F9/5004 , C07F9/5031 , C08L19/006
摘要： Rubbery polymers can be formed having the general formula: R1R2N—(CH2)n—X—CH2—CHR3R4 wherein R1 and R2 are independently selected from a group consisting of alkyls, cycloalkyls, alkenyls, cycloalkenyls, aryls, phenyls, heterocycles, acyls, and silanes, or R1 in combination with R2 forms a heterocyclic ring; n is an integer from 1 to 20; X is selected from a group consisting of sulfur, a phosphorus moiety, and a silicon moiety; R3 and R4 are one of hydrogen, alkyls, alkenyls, and at least one of which includes reactive unsaturation such as an alkenyl group. Moreover, this invention discloses a process of making functionalized rubbery polymers from the functionalized monomers.
摘要翻译：可以形成具有以下通式的橡胶状聚合物：R1R2N-（CH2）n-X-CH2-CHR3R4，其中R1和R2独立地选自烷基，环烷基，烯基，环烯基，芳基，苯基，杂环，酰基，和硅烷，或R 1与R 2组合形成杂环; n为1〜20的整数， X选自硫，磷部分和硅部分; R3和R4是氢，烷基，烯基之一，并且其中至少一个包括反应性不饱和键如烯基。此外，本发明公开了一种由官能化单体制备官能化橡胶聚合物的方法。

3. 发明授权

US07612147B2 Dendrimers of rubbery polymers 失效
标题翻译：橡胶聚合物的树枝状聚合物
公开(公告)号：US07612147B2
公开(公告)日：2009-11-03
申请号：US11176457
申请日：2005-07-07
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Chad Aaron Jasiunas
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Chad Aaron Jasiunas
IPC分类号： C08C19/25 , C08F8/18 , C08F36/04 , C08J3/24
CPC分类号： C08C19/44 , B60C1/0016 , C08G83/003 , C08L15/00 , C08L101/005 , Y10T152/10 , Y10T152/10495
摘要： This invention discloses a process for synthesizing a dendrimer of a rubbery polymer comprising: (a) reacting a lithium terminated rubbery polymer with a halogenated silicon containing compound to produce a polymer which is terminated with halogenated silicon moieties, wherein the halogenated silicon contain compound has at least four halogen atoms which are bonded directly to silicon atoms, wherein the ratio of the lithium terminated rubbery polymer to halogen atoms in the halogenated silicon containing compound is within the range of 2:n to (n−1):n, wherein n represents the number of halogen atoms that are bonded directly to silicon atoms in the halogenated silicon containing compound, wherein the halogenated silicon containing compound contains at least three halogen atoms which are bonded directly to a silicon atom; (b) reacting the polymer which is terminated with halogenated silicon moieties with a molar excess of a tertiary alcohol to produce a polymer which is terminated with hydroxy silyl moieties; and (c) allowing the polymer which is terminated with the hydroxy silyl moieties to couple under conditions sufficient to produce a dendrimer containing siloxane linkages. It has also be found that similar dendrimers having improved processability can be make utilizing halogenated tin containing compounds in stead of the halogenated silicon containing compound.
摘要翻译：本发明公开了一种用于合成橡胶状聚合物树枝状聚合物的方法，其包括：（a）使锂封端的橡胶状聚合物与含卤化硅的化合物反应以制备用卤化硅部分封端的聚合物，其中卤化硅含有化合物在至少四个与硅原子直接键合的卤素原子，其中锂封端的橡胶状聚合物与含卤化硅化合物中的卤素原子的比例在2：n至（n-1）：n的范围内，其中n表示与卤代硅化合物中的硅原子直接键合的卤素原子数，其中含卤化硅的化合物含有至少三个与硅原子直接键合的卤素原子; （b）将用卤代硅部分封端的聚合物与摩尔过量的叔醇反应，以产生用羟基甲硅烷基部分封端的聚合物; 和（c）使在羟基甲硅烷基部分封端的聚合物在足以产生含有硅氧烷键的树枝状聚合物的条件下偶联。还可以发现，具有改进加工性能的类似树枝状大分子可以利用含卤化锡的化合物代替含卤化硅的化合物。

4. 发明授权

US07189792B2 Catalyst for synthesizing high trans polymers 失效
标题翻译：用于合成高反式聚合物的催化剂
公开(公告)号：US07189792B2
公开(公告)日：2007-03-13
申请号：US11311495
申请日：2005-12-19
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Chad Aaron Jasiunas , Laurie Elizabeth Austin
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Chad Aaron Jasiunas , Laurie Elizabeth Austin
IPC分类号： C08F4/50 , C08F36/06
CPC分类号： C08F36/06 , C08F4/484 , C08F4/52 , C08F4/48 , C08F4/50
摘要： The process and catalyst of this invention can be utilized to synthesize homo and copolymers of conjugated diene monomers and vinyl aromatic monomers having high trans contents of greater than 60% with low melting points. These homo and copolymers of conjugated diene monomers and vinyl aromatic monomers can be utilized in tire tread and sidewall rubbers that exhibit outstanding wear and tear characteristics in the tread and excellent flexing properties in the sidewall. The rubber polymers of this invention are made utilizing an improved catalyst system. This catalyst system is comprised of (a) organo aluminum compounds, (b) organo lithium compounds, (c) a barium compound selected from barium salts of (i) di(ethylene glycol) ethyl ether, (ii) di(ethylene glycol) propyl ether, (iii) di(ethylene glycol) hexyl ether, (iv) di(N,N-dimethyl amino glycol) ethyl ether, (v) menthol and thymol in the presence of polar modifier consisting of water, alcohols, amines, thiols, phosphates and phosphites. The trans polymers and copolymers of this invention made with the above catalyst system typically have a glass transition temperature ranging from −97° C. to −40° C., a melt temperature ranging from −30° C. to +30° C., and a number average molecular weight from 20,000 to 250,000. The inclusion of such polar modifiers in the barium catalyst system results in a high styrene content in copolymerization, a high trans content, and high molecular weight. Copolymers of conjugated diolefin monomers and vinyl aromatic monomers made with the catalyst system of this invention also have a tapered macrostructure.
摘要翻译：本发明的方法和催化剂可用于合成共轭二烯单体和具有高反式含量大于60％的低熔点的乙烯基芳族单体的均聚物和共聚物。共轭二烯单体和乙烯基芳族单体的这些均聚物和共聚物可以用于轮胎胎面和侧壁橡胶，其在胎面中表现出优异的耐磨性和优异的弯曲性能。使用改进的催化剂体系制备本发明的橡胶聚合物。该催化剂体系包括（a）有机铝化合物，（b）有机锂化合物，（c）选自（i）二（乙二醇）乙醚的钡盐，（ii）二（乙二醇）丙基醚，（iii）二（乙二醇）己基醚，（iv）二（N，N-二甲基氨基乙二醇）乙醚，（v）薄荷醇和百里酚在由水，醇，胺，硫醇，磷酸盐和亚磷酸盐。用上述催化剂体系制备的本发明的反式聚合物和共聚物通常具有-97℃至-40℃的熔融温度范围为-30℃至+ 30℃的玻璃化转变温度。，数均分子量为20,000〜250,000。在钡催化剂体系中包含这种极性改性剂导致共聚反应中苯乙烯含量高，反式含量高，分子量高。用本发明的催化剂体系制得的共轭二烯烃单体和乙烯基芳族单体的共聚物也具有锥形宏观结构。

5. 发明授权

US07153805B2 Group III-B metal catalyst system 有权
公开(公告)号：US07153805B2
公开(公告)日：2006-12-26
申请号：US11240862
申请日：2005-09-30
申请人： Wen-Liang Hsu , Adel Farhan Halasa , Chad Aaron Jasiunas
发明人： Wen-Liang Hsu , Adel Farhan Halasa , Chad Aaron Jasiunas
IPC分类号： C08F4/52 , C08F236/06 , C08F236/08
CPC分类号： C08F36/04 , C08F136/06 , C08F136/08 , C08F4/58 , C08F4/545 , C08F236/06 , C08F236/08
摘要： The subject invention relates to a process for preparing a catalyst system that comprises the sequential steps of (I) reacting an organometalic compound that contains a metal from Group III-B of the Periodic System with an organoaluminum compound at a temperature which is within the range of 50° C. to 100° C. to produce an aluminum modified Group III-B metal containing catalyst component, and (II) mixing the aluminum modified Group III-B metal containing catalyst component with a halogen containing compound to produce the Group III-B metal containing catalyst system, wherein the catalyst system is void of compounds selected from the group consisting of aliphatic alcohols, cycloaliphatic alcohols, aliphatic thiols, cycloaliphatic thiols, trialkyl silanols, and triaryl silanols, wherein the organometalic compound that contains a metal from Group III-B of the Periodic System is reacted with the organoaluminum compound in the absence of conjugated diene monomers, and wherein the catalyst system is prepared in the absence of compounds that contain labile halogen atoms.

6. 发明授权

US06995224B2 Functionalized monomers for synthesis of rubbery polymers 失效
标题翻译：用于合成橡胶状聚合物的官能化单体
公开(公告)号：US06995224B2
公开(公告)日：2006-02-07
申请号：US11043589
申请日：2005-01-26
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Jin-Ping Zhou , Chad Aaron Jasiunas
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Jin-Ping Zhou , Chad Aaron Jasiunas
IPC分类号： C08F126/06
CPC分类号： C08F236/14 , C08C19/44 , C08F236/10
摘要： This invention discloses a process for synthesizing an amine functionalized monomer that comprises (1) reacting a secondary amine with a 2,3-dihalopropene to produce a vinyl halide containing secondary amine having a structural formula selected from the group consisting of wherein R and R′ can be the same or different and represent allyl, alkoxyl or alkyl groups containing from 1 to about 10 carbon atoms, and wherein X represents a halogen atom, and wherein m represents an integer from 4 to about 10, and wherein X represents a halogen atom; and (2) reacting the vinyl halide containing secondary amine with a vinyl magnesium halide to produce the monomer having a structural formula wherein R and R′ can be the same or different and represent alkyl, allyl or alkoxyl groups containing from 1 to about 10 carbon atoms, and wherein m represents an integer from about 4 to about 10.
摘要翻译：本发明公开了一种用于合成胺官能化单体的方法，其包括（1）使仲胺与2,3-二卤代丙烯反应以制备含有仲胺的乙烯基卤化物，所述仲胺具有选自以下的结构式：化学式id =“ CHEM-US-00001“num =”000

7. 发明申请

US20100043938A1 DENDRIMERS OF RUBBERY POLYMERS 失效
标题翻译：橡胶聚合物胶粘剂
公开(公告)号：US20100043938A1
公开(公告)日：2010-02-25
申请号：US12611807
申请日：2009-11-03
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Chad Aaron Jasiunas
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Chad Aaron Jasiunas
IPC分类号： B60C1/00 , C08G77/06 , C08G79/12
CPC分类号： C08C19/44 , B60C1/0016 , C08G83/003 , C08L15/00 , C08L101/005 , Y10T152/10 , Y10T152/10495
摘要： This invention discloses a process for synthesizing a dendrimer of a rubbery polymer comprising: (a) reacting a lithium terminated rubbery polymer with a halogenated silicon containing compound to produce a polymer which is terminated with halogenated silicon moieties, wherein the halogenated silicon contain compound has at least four halogen atoms which are bonded directly to silicon atoms, wherein the ratio of the lithium terminated rubbery polymer to halogen atoms in the halogenated silicon containing compound is within the range of 2:n to (n-1):n, wherein n represents the number of halogen atoms that are bonded directly to silicon atoms in the halogenated silicon containing compound, wherein the halogenated silicon containing compound contains at least three halogen atoms which are bonded directly to a silicon atom; (b) reacting the polymer which is terminated with halogenated silicon moieties with a molar excess of a tertiary alcohol to produce a polymer which is terminated with hydroxy silyl moieties; and (c) allowing the polymer which is terminated with the hydroxy silyl moieties to couple under conditions sufficient to produce a dendrimer containing siloxane linkages. It has also be found that similar dendrimers having improved processability can be make utilizing halogenated tin containing compounds in stead of the halogenated silicon containing compound.
摘要翻译：本发明公开了一种用于合成橡胶状聚合物树枝状聚合物的方法，包括：（a）使锂封端的橡胶状聚合物与含卤化硅的化合物反应以制备用卤化硅部分封端的聚合物，其中卤化硅含有化合物在至少四个与硅原子直接键合的卤素原子，其中锂封端的橡胶状聚合物与含卤化硅化合物中的卤素原子的比例在2：n至（n-1）：n的范围内，其中n表示与卤代硅化合物中的硅原子直接键合的卤素原子数，其中含卤化硅的化合物含有至少三个与硅原子直接键合的卤素原子; （b）将用卤代硅部分封端的聚合物与摩尔过量的叔醇反应，以产生用羟基甲硅烷基部分封端的聚合物; 和（c）使在羟基甲硅烷基部分封端的聚合物在足以产生含有硅氧烷键的树枝状聚合物的条件下偶联。还可以发现，具有改进加工性能的类似树枝状大分子可以利用含卤化锡的化合物代替含卤化硅的化合物。

8. 发明申请

US20090156769A1 FUNCTIONALIZED MONOMERS AND FUNCTIONALIZED RUBBERY POLYMERS MADE THEREWITH 有权
标题翻译：功能性单体和功能性橡胶聚合物
公开(公告)号：US20090156769A1
公开(公告)日：2009-06-18
申请号：US11955453
申请日：2007-12-13
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Leh-Yeh Hsu , Shingo Futamura , Joe Zhou , Chad Aaron Jasiunas
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Leh-Yeh Hsu , Shingo Futamura , Joe Zhou , Chad Aaron Jasiunas
IPC分类号： C08F4/28 , C07C381/00 , C07F9/28 , C07F7/08 , C08F230/02 , C08F26/00 , C08F26/06
CPC分类号： C08F236/14 , C07C323/25 , C07F7/1804 , C07F9/5004 , C07F9/5031 , C08L19/006
摘要： Rubbery polymers can be formed having the general formula: R1R2N—(CH2)n—X—CH2—CHR3R4 wherein R1 and R2 are independently selected from a group consisting of alkyls, cycloalkyls, alkenyls, cycloalkenyls, aryls, phenyls, heterocycles, acyls, and silanes, or R1 in combination with R2 forms a heterocyclic ring; n is an integer from 1 to 20; X is selected from a group consisting of sulfur, a phosphorus moiety, and a silicon moiety; R3 and R4 are one of hydrogen, alkyls, alkenyls, and at least one of which includes reactive unsaturation such as an alkenyl group. Moreover, this invention discloses a process of making functionalized rubbery polymers from the functionalized monomers.
摘要翻译：可以形成具有以下通式的橡胶状聚合物：<？in-line-formula description =“In-line formula”end =“lead”？> R1R2N-（CH2）nX-CH2-CHR3R4 <？in-line-formula description 其中R 1和R 2独立地选自烷基，环烷基，烯基，环烯基，芳基，苯基，杂环，酰基和硅烷，或R 1与 R2形成杂环; n为1〜20的整数， X选自硫，磷部分和硅部分; R3和R4是氢，烷基，烯基之一，并且其中至少一个包括反应性不饱和键如烯基。此外，本发明公开了一种由官能化单体制备官能化橡胶聚合物的方法。

9. 发明授权

US07022783B2 Group III-B metal catalyst system 有权
标题翻译： III-B族金属催化剂体系
公开(公告)号：US07022783B2
公开(公告)日：2006-04-04
申请号：US10765485
申请日：2004-01-27
申请人： Wen-Liang Hsu , Adel Farhan Halasa , Chad Aaron Jasiunas
发明人： Wen-Liang Hsu , Adel Farhan Halasa , Chad Aaron Jasiunas
IPC分类号： C08F4/52 , C08F236/06 , C08F236/08
CPC分类号： C08F36/04 , C08F136/06 , C08F136/08 , C08F4/58 , C08F4/545 , C08F236/06 , C08F236/08
摘要： The subject invention relates to a technique for synthesizing rubbery non-tapered, random, copolymers of 1,3-butadiene and isoprene. These rubbery copolymers exhibit an excellent combination of properties for utilization in tire sidewall rubber compounds for truck tires. By utilizing these isoprene-butadiene rubbers in tire sidewalls, tires having improved cut growth resistance can be built without sacrificing rolling resistance. Such rubbers can also be employed in tire tread compounds to improve tread wear characteristics and decrease rolling resistance without sacrificing traction characteristics. This invention more specifically discloses a process for the synthesis of isoprene-butadiene rubber which comprises copolymerizing isoprene monomer and 1,3-butadiene monomer in an organic solvent in the presence of a Group III-B metal containing catalyst system that is made by the sequential steps of (I) reacting an organometalic compound that contains a metal from Group III-B of the Periodic System with an organoaluminum compound at a temperature which is within the range of 50° C. to 100° C. to produce an aluminum modified Group III-B metal containing catalyst component, and (II) mixing the aluminum modified Group III-B metal containing catalyst component with a halogen containing compound, wherein the catalyst system is void of compounds selected from the group consisting of aliphatic alcohols, cycloaliphatic alcohols, aliphatic thiols, cycloaliphatic thiols, trialkyl silanols, and triaryl silanols.
摘要翻译：本发明涉及一种用于合成1,3-丁二烯和异戊二烯橡胶状非渐变，无规共聚物的技术。这些橡胶状共聚物表现出用于卡车轮胎的轮胎胎侧橡胶化合物中的优异的性能组合。通过在轮胎侧壁中使用这些异戊二烯 - 丁二烯橡胶，可以在不牺牲滚动阻力的情况下构建具有改善的耐切割生长性的轮胎。这种橡胶也可以用在轮胎胎面胶料中以改善胎面磨损特性并降低滚动阻力而不牺牲牵引特性。本发明更具体地公开了一种用于合成异戊二烯 - 丁二烯橡胶的方法，该方法包括在含有III-B族金属的催化剂体系存在下，将异戊二烯单体和1,3-丁二烯单体在有机溶剂中共聚，步骤（I）使含有周期性体系的III-B族金属的有机金属化合物与有机铝化合物在50℃至100℃的温度范围内反应，生成铝改性基团含有III-B族金属的催化剂组分，和（II）将含有铝的改性的含III-B族金属的催化剂组分与含卤素化合物混合，其中催化剂体系没有选自脂族醇，脂环族醇，脂族硫醇，脂环族硫醇，三烷基硅烷醇和三芳基硅烷醇。

10. 发明授权

US06583244B1 Synthesis of rubber having a low vinyl content 失效
标题翻译：低乙烯基含量的橡胶的合成
公开(公告)号：US06583244B1
公开(公告)日：2003-06-24
申请号：US09999854
申请日：2001-10-31
申请人： Chad Aaron Jasiunas , John Robert Zuppo, III , Adel Farhan Halasa , Wen-Liang Hsu
发明人： Chad Aaron Jasiunas , John Robert Zuppo, III , Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F446
CPC分类号： C08F4/48 , C08C19/44 , C08F36/04
摘要： Metal salts of cyclic alcohols can be used as modifiers in lithium initiated solution polymerizations of diene monomers into rubbery polymers having a low vinyl content. For instance, such initiator systems can be used in the copolymerization of styrene and isoprene to produce low vinyl styrene-isoprene rubber having a random distribution of repeat units that are derived from styrene. It is important for such polymerizations to be conducted in the absence of polar modifiers, such as Lewis bases. The subject invention more specifically discloses an initiator system which is comprised of (a) a lithium initiator and (b) a metal salt of a cyclic alcohol, wherein said initiator system is void of polar modifiers. The present invention also discloses a process for preparing a rubbery polymer having a low vinyl content which comprises: polymerizing at least one diene monomer with a lithium initiator at a temperature which is within the range of about 5° C. to about 100° C. in the presence of a metal salt of a cyclic alcohol, wherein the molar ratio of the metal salt of the cyclic alcohol to the lithium initiator is within the range of about 0.05:1 to about 10:1, and wherein the process is conducted in the absence of polar modifiers.
摘要翻译：环醇的金属盐可以用作二烯单体的锂引发溶液聚合成具有低乙烯基含量的橡胶状聚合物中的改性剂。例如，这种引发剂体系可以用于苯乙烯和异戊二烯的共聚合以制备具有衍生自苯乙烯的重复单元的随机分布的低乙烯基苯乙烯 - 异戊二烯橡胶。在没有极性改性剂如路易斯碱的情况下进行这种聚合是重要的。本发明更具体地公开了一种引发剂体系，其包括（a）锂引发剂和（b）环状醇的金属盐，其中所述引发剂体系没有极性改性剂。本发明还公开了一种制备低乙烯基含量的橡胶状聚合物的方法，该方法包括：在约5℃至约100℃范围内的温度下，用锂引发剂聚合至少一种二烯单体。在环醇的金属盐的存在下，其中环醇与锂引发剂的金属盐的摩尔比在约0.05:1至约10:1的范围内，并且其中所述方法在没有极性改性剂。

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