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1. 发明授权

US07285605B1 Batch process for synthesizing rubbery polymers having a high trans microstructure content 失效
标题翻译：用于合成具有高反式微结构含量的橡胶状聚合物的分批方法
公开(公告)号：US07285605B1
公开(公告)日：2007-10-23
申请号：US11468427
申请日：2006-08-30
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Jean Steininger Clites , Timothy John Wolfgang
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Jean Steininger Clites , Timothy John Wolfgang
IPC分类号： C08F4/52 , C08F236/10
CPC分类号： C08F236/10 , C08F4/52
摘要： The present invention is directed to a batch process for synthesizing rubbery polymers, such as styrene-butadiene rubber, having a high trans microstructure. In one embodiment, the batch process involves mixing a catalyst system with styrene and butadiene monomers in a single reactor, with additional butadiene monomer being added after a desired period of time to further drive styrene conversion and, thus, provide a desirable high trans rubbery polymer, e.g., styrene-butadiene rubber. The copolymerization process can be conducted at a temperature in the range of about 20° C. to about 180° and over a period of about 1 to about 4 hours. The catalyst system can include (a) an organolithium compound, (b) a group IIa metal salt, and (c) an organoaluminum compound. The catalyst system may further optionally include an amine compound and/or an organomagnesium compound.
摘要翻译：本发明涉及用于合成橡胶状聚合物（例如苯乙烯 - 丁二烯橡胶）的间歇法，其具有高的反相微观结构。在一个实施方案中，间歇方法包括在单个反应器中将催化剂体系与苯乙烯和丁二烯单体混合，在所需的时间段内加入另外的丁二烯单体以进一步驱动苯乙烯转化，从而提供期望的高反式橡胶状聚合物，例如丁苯橡胶。共聚方法可以在约20℃至约180℃的温度和约1至约4小时的时间内进行。催化剂体系可以包括（a）有机锂化合物，（b）IIa族金属盐和（c）有机铝化合物。催化剂体系还可以任选地包括胺化合物和/或有机镁化合物。

2. 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。

3. 发明授权

US07906682B2 Synthesis of soluble functionalized lithium initiators 有权
标题翻译：可溶性官能化锂引发剂的合成
公开(公告)号：US07906682B2
公开(公告)日：2011-03-15
申请号：US12686768
申请日：2010-01-13
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C07C221/00 , C07C225/00 , C08F8/00 , C08F32/00 , C08F132/00 , C08F232/00
CPC分类号： B60C1/0016 , C07F1/005 , C07F1/02 , C08C19/44 , C08F36/04 , C08F4/488
摘要： This invention discloses a process for making dilithium initiators in high purity. This process can be conducted in the absence of amines which is desirable since amines can act as modifiers for anionic polymerizations. The dilithium compounds made are highly desirable because they are soluble in aromatic solvents. The present invention also discloses a tire which is comprised of a generally toroidal-shaped carcass with an outer circumferential tread, two spaced beads, at least one ply extending from bead to bead and sidewalls extending radially from and connecting said tread to said beads, wherein said tread is adapted to be ground-contacting, and wherein said tread is a cured the rubber formulation which is comprised of (a) at least one rubbery polymer containing functional groups of the structural formula: wherein R, R′ and R″ can be the same or different, wherein R is selected from the group consisting of hydrogen atoms, alkyl groups, aryl groups, alkaryl groups, and amino aryl groups, and wherein R′ and R″ represent alkyl groups alkyl groups that contain from 1 to 8 carbon atoms, and (b) at least one member selected from the group consisting of carbon black and silica.
摘要翻译：本发明公开了一种制备高纯度二锂引发剂的方法。该方法可以在不存在胺的情况下进行，因为胺可以用作阴离子聚合的改性剂。所制备的二锂化合物是非常需要的，因为它们可溶于芳族溶剂。本发明还公开了一种轮胎，其包括具有外圆周胎面的大致环形胎体，两个间隔开的胎圈，从胎圈到胎圈延伸的至少一个帘布层和从所述胎面径向延伸并将所述胎面连接到所述胎圈的侧壁，其中所述胎面适于与地面接触，并且其中所述胎面是固化的橡胶配方，其由（a）至少一种含有以下结构式的官能团的橡胶状聚合物组成：其中R，R'和R“可以是相同或不同，其中R选自氢原子，烷基，芳基，烷芳基和氨基芳基，其中R'和R“表示含有1至8个碳的烷基基团原子，和（b）选自碳黑和二氧化硅中的至少一种。

4. 发明授权

US07884168B2 Heterogeneous rubbery polymers having random, tapered, and block portions therein and methods of making same 有权
标题翻译：具有随机，锥形和嵌段部分的非均相橡胶状聚合物及其制备方法
公开(公告)号：US07884168B2
公开(公告)日：2011-02-08
申请号：US12371122
申请日：2009-02-13
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Leh-Yeh Hsu, legal representative , Warren James Busch , David Michael Smith, Sr. , Jennifer Elizabeth Labbe , Scott Edwards Johnson
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Warren James Busch , David Michael Smith, Sr. , Jennifer Elizabeth Labbe , Scott Edwards Johnson
IPC分类号： C08F236/10 , C08F2/04 , C08F4/48
CPC分类号： B60C1/0016 , C08F212/08 , C08F236/10 , Y10S152/905 , C08F2/001
摘要： A heterogeneous rubbery polymer is provided that includes a polymer chain derived from a vinyl aromatic monomer and a conjugated diolefin monomer, wherein from greater than 20 weight percent to about 40 weight percent of units in the rubbery polymer are derived from the vinyl aromatic monomer and from about 60 weight percent to about 80 weight percent of units in the rubbery polymer are derived from the conjugated diolefin monomer. The polymer chain is further characterized by having greater than zero and less than about 30 weight percent of the vinyl aromatic units in sequences containing 1 vinyl aromatic unit, from about 5 weight percent to about 20 weight percent of the vinyl aromatic units in sequences containing 5 to 8 vinyl aromatic units, and greater than zero and less than about 5 weight percent of the vinyl aromatic units in sequences containing 9 or more vinyl aromatic units.
摘要翻译：提供了一种异相橡胶状聚合物，其包括衍生自乙烯基芳族单体和共轭二烯烃单体的聚合物链，其中橡胶状聚合物中大于20重量％至约40重量％的单元衍生自乙烯基芳族单体和橡胶状聚合物中约60重量％至约80重量％的单元衍生自共轭二烯单体。聚合物链的特征还在于具有大于零且小于约30重量％的含有乙烯基芳族单元的乙烯基芳族单元，约5重量％至约20重量％的乙烯基芳族单元，其序列包含5 至8个乙烯基芳族单元，并且大于零且小于约5重量％的含有9个或更多个乙烯基芳族单元的乙烯基芳族单元。

5. 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。

6. 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。

7. 发明申请

US20080161519A1 Catalyst System for Synthesizing Amine Functionalized Rubbery Polymers 有权
标题翻译：用于合成胺官能化橡胶聚合物的催化剂体系
公开(公告)号：US20080161519A1
公开(公告)日：2008-07-03
申请号：US11616986
申请日：2006-12-28
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F2/00
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 or high vinyl microstructure. The catalyst system, in one embodiment, includes an organolithium amine compound, and one or more of (a) a group IIa metal salt of an amino glycol or a glycol ether, (b) an organoaluminum compound, or (c) 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：本发明涉及用于合成胺官能化并具有高反式或高乙烯基显微组织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，催化剂体系包括有机锂化合物和（a）氨基二醇或二醇醚的IIa族金属盐，（b）有机铝化合物或（c）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。

8. 发明授权

US07222650B2 Tire with a tread comprising a rubbery polymer of a functionalized monomer 有权
标题翻译：具有包含官能化单体的橡胶状聚合物的胎面的轮胎
公开(公告)号：US07222650B2
公开(公告)日：2007-05-29
申请号：US10429382
申请日：2003-05-05
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Kenneth Allen Bates , Shingo Futamura
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Kenneth Allen Bates , Shingo Futamura
IPC分类号： B60C1/00 , C08F26/06
CPC分类号： B60C1/0016 , C08K3/013 , Y10S152/905 , C08L19/006
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 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，所述仲胺具有选自下组的结构式：其中R和R' 可以相同或不同，表示含有1至约10个碳原子的烯丙基，烷氧基或烷基，其中X表示卤素原子，其中m表示4至约10的整数，并且其中X表示卤素原子 ; 和（2）使含有乙烯基卤的仲胺与乙烯基卤化镁反应以制备具有结构的单体，其中R和R'可以相同或不同并且表示含有1至约10个碳原子的烷基，烯丙基或烷氧基，并且其中m表示约4至约10的整数。

9. 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。

10. 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.

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