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91. 发明授权

US06693160B1 Functionalized monomers for synthesis of rubbery polymers 失效
公开(公告)号：US06693160B1
公开(公告)日：2004-02-17
申请号：US10384020
申请日：2003-03-07
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F23814
CPC分类号： C08F236/14 , 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.

92. 发明授权

US06559240B2 Process for tin/silicon coupling functionalized rubbers 失效
标题翻译：锡/硅偶联官能化橡胶的工艺
公开(公告)号：US06559240B2
公开(公告)日：2003-05-06
申请号：US10001567
申请日：2001-11-15
申请人： Wen-Liang Hsu , Adel Farhan Halasa
发明人： Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： C08F800
CPC分类号： C08C19/44 , C08F36/04 , C08F4/48
摘要： Rubbery polymers made by anionic polymerization can be coupled with both tin halides and silicon halides to improve the characteristics of the rubber for use in some applications, such as tire treads. In cases where the rubbery polymer is synthesized by anionic polymerization utilizing a polar modifier it is difficult to attain a high level of coupling. This invention is based upon the unexpected finding that the coupling efficiency of rubbery polymers made with polar modifiers can be significantly improved by initiating the anionic polymerization with an alkylsilyloxy protected functional lithium initiator having a structural formula selected from the group consisting of: (a): wherein X represents a group IVa element selected from the group consisting of carbon, silicon, germanium, and tin, wherein Y represents phosphorous or nitrogen, wherein R represents alkyl groups that can be the same or different, wherein the alkyl groups contain from 1 to about 8 carbon atoms, and wherein A represents an alkylene group containing from 1 to about 12 carbon atoms.
摘要翻译：通过阴离子聚合制备的橡胶聚合物可与锡卤化物和硅卤化物结合，以改善用于某些应用中的橡胶的特性，例如轮胎胎面。在通过使用极性改性剂的阴离子聚合合成橡胶状聚合物的情况下，难以获得高水平的偶联。本发明基于意想不到的发现，通过用具有选自以下的结构式的烷基甲硅烷氧基保护的官能锂引发剂引发阴离子聚合，可以显着改善由极性改性剂制备的橡胶状聚合物的偶联效率：（a）：其中X表示选自碳，硅，锗和锡的IVa族元素，其中Y表示磷或氮，其中R表示可以相同或不同的烷基，其中烷基含有1〜约8个碳原子，并且其中A表示含有1至约12个碳原子的亚烷基。

93. 发明授权

US06489415B2 Process for synthesizing trans-1,4-polybutadiene 失效
公开(公告)号：US06489415B2
公开(公告)日：2002-12-03
申请号：US09730257
申请日：2000-12-05
申请人： Wen-Liang Hsu , Adel Farhan Halasa
发明人： Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： C08F446
CPC分类号： C08F136/06 , C08F4/50 , C08F4/48
摘要： The process and catalyst system of this invention can be utilized to synthesize polybutadiene rubber having a high trans content and a low melting point by solution polymerization. The trans-polybutadiene rubber made by the process of this invention can be utilized in tire tread rubbers that exhibit outstanding wear characteristics. More importantly, the trans-polybutadiene rubber of this invention can be easily processed because of its low level of crystallinity. In fact, the trans-polybutadiene made by the process of this invention does not need to be heated in a “hot-house” before being used in making rubber compounds. This invention more specifically reveals a process for synthesizing trans-polybutadiene rubber which comprises polymerizing 1,3-butadiene in an organic solvent in the presence of a catalyst system which comprises (a) an organolithium compound, (b) a barium compound selected from the group consisting of (i) barium salts of cyclic alcohols, such as barium mentholate, and (ii) barium thymolate, and (c) an organoaluminum compound. The trans-polybutadiene made with the catalyst system of this invention typically has a glass transition temperature that is within the range of about -97° C. to about -90° C., a melting point that is within the range of about -30° C. to about 30° C., and a number average molecular weight that is within the range of about 50,000 to about 400,000.

94. 发明授权

US06359088B1 Calcium-based catalyst system 失效
标题翻译：钙基催化剂体系
公开(公告)号：US06359088B1
公开(公告)日：2002-03-19
申请号：US09389507
申请日：1999-09-03
申请人： Adel Farhan Halasa , Wen-Liang Hsu , John Robert Zuppo, III
发明人： Adel Farhan Halasa , Wen-Liang Hsu , John Robert Zuppo, III
IPC分类号： C08F800
CPC分类号： C08F136/08 , C08F236/10 , C08F4/54
摘要： The process and catalyst system of this invention can be utilized to synthesize a highly random styrene-butadiene rubber having a high trans content by solution polymerization. The styrene-butadiene rubber made by the process of this invention can be utilized in tire tread rubbers that exhibit improved wear characteristics. This invention more specifically reveals a catalyst system for use in isothermal polymerizations which consists essentially of (a) an organolithium compound, (b) a calcium alkoxide and (c) a lithium alkoxide. The subject invention further discloses a process for synthesizing a random styrene-butadiene rubber having a low vinyl content by a process which comprises copolymerizing styrene and 1,3-butadiene under isothermal conditions in an organic solvent in the presence of a catalyst system which consists essentially of (a) an organolithium compound, (b) a calcium alkoxide and (c) a lithium alkoxide. An amine can also be added to the catalyst system to increase the molecular weight (Mooney viscosity) of the rubber.
摘要翻译：本发明的方法和催化剂体系可用于通过溶液聚合合成具有高反式含量的高度无规的苯乙烯 - 丁二烯橡胶。通过本发明方法制备的苯乙烯 - 丁二烯橡胶可用于表现出改善的磨损特性的轮胎胎面橡胶。本发明更具体地揭示了用于等温聚合的催化剂体系，其基本上由（a）有机锂化合物，（b）醇盐和（c）醇锂组成。本发明还公开了一种合成具有低乙烯基含量的无规苯乙烯 - 丁二烯橡胶的方法，该方法包括在等温条件下在有机溶剂中在催化剂体系存在下共聚苯乙烯和1,3-丁二烯的方法，所述催化剂体系基本上组成（a）有机锂化合物，（b）烷氧基钙和（c）醇锂。还可以向催化剂体系中加入胺以提高橡胶的分子量（门尼粘度）。

95. 发明授权

US06329467B1 Coupled rubbery polymers 有权
标题翻译：偶联的橡胶聚合物
公开(公告)号：US06329467B1
公开(公告)日：2001-12-11
申请号：US09467861
申请日：1999-12-20
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Charles John Pearson , Yi Feng
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Charles John Pearson , Yi Feng
IPC分类号： C08F842
CPC分类号： C08C19/44 , B60C1/0016 , C08F8/42
摘要： It has been unexpectedly found that greatly improved properties for tire rubbers, such as lower hysteresis, can be attained by coupling the rubber with both a tin halide, such as tin tetrachloride, and a silicon halide, such as silicon tetrachloride. Even better characteristics for use in tire tread compounds can be realized by asymmetrically coupling the rubbery polymer. This invention more specifically discloses a coupled rubbery polymer which is particularly valuable for use in manufacturing tire tread compounds, said coupled rubbery polymer being comprised of (1) tin atoms having at least three polydiene arms covalently bonded thereto and (2) silicon atoms having at least three polydiene arms covalently bonded thereto.
摘要翻译：已经意外地发现，通过将橡胶与卤化锡如四氯化锡和卤化硅如四氯化硅二者相结合，可以获得轮胎橡胶的较好的性能，例如较低的滞后性。用于轮胎胎面胶料的更好的特性可以通过不对称地偶合橡胶状聚合物来实现。本发明更具体地公开了一种特别有价值地用于制造轮胎胎面胶料的偶联橡胶状聚合物，所述连接的橡胶状聚合物包括（1）具有至少三个与其共价连接的聚二烯臂的锡原子和（2）共价键合至少三个聚二烯臂。

96. 发明授权

US06293325B1 Technique for reducing the cold flow of rubbers 失效
标题翻译：降低橡胶冷流的技术
公开(公告)号：US06293325B1
公开(公告)日：2001-09-25
申请号：US09640215
申请日：2000-08-16
申请人： Wen-Liang Hsu , Adel Farhan Halasa
发明人： Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： B60C500
CPC分类号： C08F236/10 , B60C1/0016 , C08F297/04 , C08L7/00 , C08L9/00 , C08L9/06 , C08L21/00 , C08L53/02 , Y10T152/10495 , C08F4/48 , C08L2666/02 , C08L2666/24
摘要： Cold flow is a problem that is commonly encountered in the handling and storage of low molecular weight linear rubbers, such as low vinyl polybutadiene rubber and isoprene-butadiene rubber. This invention is based upon the unexpected discovery that the cold flow of such rubbery polymers can be greatly reduced by incorporating a small block of polystyrene therein. The rubbery polymers of this invention which exhibit a low level of cold flow can be synthesized by simply terpolymerizing 1,3-butadiene, isoprene and from about 0.5 phm to about 3 phm of styrene under anionic polymerization conditions in the absence of a polar modifier. It is preferred to utilize batch .polymerization techniques. However, continuous polymerization techniques can also be utilized. This invention more specifically disclosed a rubbery polymer which is comprised of polymer chains containing repeat units which are derived from 1,3-butadiene, isoprene and from about 0.5 weight percent to about 3 weight percent styrene, wherein the repeat units which are derived from styrene are in blocks at the ends of the polymer chains, wherein the rubbery polymer has a glass transition temperature which is within the range of about −105° C. to about −65° C. and wherein the rubbery polymer has a number average molecular weight which is within the range of about 50,000 to about 600,000.
摘要翻译：冷流是在低分子量线性橡胶（例如低乙烯基聚丁二烯橡胶和异戊二烯 - 丁二烯橡胶）的处理和储存中通常遇到的问题。本发明基于意想不到的发现，通过在其中加入一小块聚苯乙烯可以大大降低这种橡胶状聚合物的冷流。表现出低水平冷流的本发明的橡胶状聚合物可以在不存在极性改性剂的阴离子聚合条件下简单地将1,3-丁二烯，异戊二烯和约0.5phm至约3phm的苯乙烯进行三聚合而合成。优选使用批量聚合技术。然而，也可以使用连续聚合技术。本发明更具体地公开了由聚合物链组成的橡胶状聚合物，该聚合物链含有衍生自1,3-丁二烯，异戊二烯和约0.5重量％至约3重量％苯乙烯的重复单元，其中衍生自苯乙烯的重复单元在聚合物链的末端处是嵌段，其中橡胶状聚合物的玻璃化转变温度在约-105℃至约-65℃的范围内，并且其中橡胶状聚合物具有数均分子量其在约50,000至约600,000的范围内。

97. 发明授权

US06204320B1 Liquid isoprene-butadiene rubber 有权
标题翻译：液体异戊二烯 - 丁二烯橡胶
公开(公告)号：US06204320B1
公开(公告)日：2001-03-20
申请号：US09249470
申请日：1999-02-12
申请人： Edward John Blok , Mark Leslie Kralevich, Jr. , Paul Harry Sandstrom , Wen-Liang Hsu , Adel Farhan Halasa
发明人： Edward John Blok , Mark Leslie Kralevich, Jr. , Paul Harry Sandstrom , Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： C08J2700
CPC分类号： C08F236/08 , B60C1/0016 , C08F236/06 , C08L21/00 , Y10T152/10495 , C08L2666/08
摘要： The subject invention discloses a liquid isoprene-butadiene rubber (IBR) which is particularly valuable for use in making treads for high performance automobile tires, including race tires, that exhibit superior dry traction characteristics and durability. The isoprene-butadiene rubber of this invention is a liquid at room temperature and is comprised of repeat units which are derived from about 5 weight percent to about 95 weight percent isoprene and from about 5 weight percent to about 95 weight percent 1,3-butadiene, wherein the repeat units derived from isoprene and 1,3-butadiene are in essentially random order. The IBR of this invention also has a low number average molecular weight which is within the range of about 3,000 to about 50,000 and has a glass transition temperature which is within the range of about −50° C. to about 20° C. This invention more specifically discloses a tire tread compound which is comprised of (a) a rubbery elastomer, (b) about 20 phr to about 80 phr of an aromatic process oil, (c) about 35 phr to about 130 phr of a filler and (d) about 4 phr to about 40 phr of a liquid isoprene-butadiene rubber having a number average molecular weight which is within the range of about 3,000 to about 50,000 and a glass transition temperature which is within the range of about −50° C. to about 20° C.
摘要翻译：本发明公开了一种特别有价值的液体异戊二烯 - 丁二烯橡胶（IBR），其用于制造具有优异的干牵引特性和耐久性的高性能汽车轮胎（包括赛车轮胎）的胎面。本发明的异戊二烯 - 丁二烯橡胶在室温下为液体，并由衍生自约5重量％至约95重量％的异戊二烯和约5重量％至约95重量％的1,3-丁二烯的重复单元，其中衍生自异戊二烯和1,3-丁二烯的重复单元基本上是随机的。本发明的IBR还具有低于约3,000至约50,000的数均分子量，玻璃化转变温度在约-50℃至约20℃的范围内。本发明更具体地公开了一种轮胎胎面胶，其由（a）橡胶弹性体，（b）约20phr至约80phr的芳族加工油，（c）约35phr至约130phr的填料和（d ）约4phr至约40phr的数均分子量在约3,000至约50,000范围内且玻璃化转变温度在约-50℃至约-50℃范围内的液体异戊二烯 - 丁二烯橡胶约20℃

98. 发明授权

US6025430A Tire tread compositions containing asymmetrically tin-coupled polybutadiene rubber 失效
公开(公告)号：US6025430A
公开(公告)日：2000-02-15
申请号：US388491
申请日：1999-09-02
申请人： Edward John Blok , Paul Harry Sandstrom , Cheryl Ann Losey , Adel Farhan Halasa , Wen-Liang Hsu , David John Zanzig , John Joseph Andre Verthe
发明人： Edward John Blok , Paul Harry Sandstrom , Cheryl Ann Losey , Adel Farhan Halasa , Wen-Liang Hsu , David John Zanzig , John Joseph Andre Verthe
IPC分类号： B60C1/00 , C08C19/44 , C08J3/26 , C08K5/548 , C08L7/00 , C08L9/00 , C08L15/00 , C08L21/00 , C08K3/36
CPC分类号： C08L15/00 , B60C1/0016 , C08C19/44 , C08K5/548 , C08L15/005 , C08L21/00 , C08L7/00 , C08L9/00
摘要： This invention relates to a tire tread compound that is easily processable which can be used to improve the treadwear, rolling resistance and traction characteristics of tires. The tire tread compounds of this invention are a blend of tin-coupled polybutadiene, high vinyl polybutadiene and natural rubber. This blend of low glass transition temperature rubber and high glass transition temperature rubber is surprisingly easy to process which makes the concept of this invention commercially feasible. Thus, the tire tread compounds of this invention can be utilized in making tires having greatly improved traction characteristics and treadwear without sacrificing rolling resistance. These improved properties may be due, in part, to better interaction and compatibility with carbon black and/or silica fillers. The polybutadiene in the blend can be asymmetrical tin-coupled to further improve the cold flow characteristics of the rubber blend. Asymmetrical tin coupling in general also leads to better processability and other beneficial properties. This invention more specifically discloses a tire tread rubber composition which is comprised of (1) from about 20 phr to about 60 phr of tin-coupled polybutadiene rubber, (2) from about 20 phr to about 60 phr of a rubber selected from the group consisting of natural rubber and synthetic polyisoprene and (3) from about 5 phr to about 40 phr of high vinyl polybutadiene rubber.

99. 发明授权

US5686530A Tire tread compound 失效
标题翻译：轮胎胎面复合
公开(公告)号：US5686530A
公开(公告)日：1997-11-11
申请号：US782841
申请日：1997-01-13
申请人： Adel Farhan Halasa , David John Zanzig , Wen-Liang Hsu , Paul Harry Sandstrom , Laurie Elizabeth Austin
发明人： Adel Farhan Halasa , David John Zanzig , Wen-Liang Hsu , Paul Harry Sandstrom , Laurie Elizabeth Austin
IPC分类号： B60C1/00 , C08L9/00 , C08L21/00 , C08L53/00 , C08L53/02 , C08L52/03 , C08F297/04
CPC分类号： C08L21/00 , B60C1/0016 , C08F297/04 , C08L53/00 , C08L9/00 , C08L9/06
摘要： The subject invention discloses a pneumatic tire having an outer circumferential tread wherein said tread is a sulfur-cured rubber composition comprised of (a) an isoprene-butadiene diblock rubber, said isoprene-butadiene diblock rubber being comprised of a butadiene block and an isoprene-butadiene block, wherein said butadiene block has a number average molecular weight which is within the range of about 25,000 to about 350,000, wherein said isoprene-butadiene block has a number average molecular weight which is within the range of about 25,000 to about 350,000, wherein said isoprene-butadiene diblock rubber has essentially one glass transition temperature which is within the range of about -100.degree. C. to about -70.degree. C., wherein said isoprene-butadiene diblock polymer has a Mooney ML-4 viscosity at 100.degree. C. which is within the range of about 50 to about 140, wherein the repeat units derived from isoprene and 1,3-butadiene in the isoprene-butadiene block are in essentially random order, and wherein said isoprene-butadiene diblock polymer does not contain any blocks which are derived solely from isoprene; and (b) a second rubber selected from the group consisting of high vinyl polybutadiene rubber, styrene-isoprene-butadiene rubber, solution styrene-butadiene rubber and emulsion styrene-butadiene rubber.
摘要翻译：本发明公开了一种具有外周胎面的充气轮胎，其中所述胎面是由（a）异戊二烯 - 丁二烯二嵌段橡胶组成的硫固化橡胶组合物，所述异戊二烯 - 丁二烯二嵌段橡胶由丁二烯嵌段和异戊二烯 - 丁二烯嵌段，其中所述丁二烯嵌段的数均分子量在约25,000至约350,000的范围内，其中所述异戊二烯 - 丁二烯嵌段的数均分子量在约25,000至约350,000的范围内，其中所述异戊二烯 - 丁二烯二嵌段橡胶具有基本上一个玻璃化转变温度，其在约-100℃至约-70℃的范围内，其中所述异戊二烯 - 丁二烯二嵌段聚合物在100℃下具有门尼ML-4粘度其在约50至约140的范围内，其中衍生自异戊二烯和1,3-丁二烯在异戊二烯 - 丁二烯嵌段中的重复单元基本上是随机的并且其中所述异戊二烯 - 丁二烯二嵌段聚合物不包含仅由异戊二烯衍生的任何嵌段; 和（b）选自高乙烯基聚丁二烯橡胶，苯乙烯 - 异戊二烯 - 丁二烯橡胶，溶剂苯乙烯 - 丁二烯橡胶和乳液丁苯橡胶的第二橡胶。

100. 发明授权

US06812277B2 Tire with component comprised of a blend of polybutadiene-rich rubber composition which contains a minor portion of styrene-rich styrene/isoprene elastomer 失效
标题翻译：轮胎与由富含聚丁二烯的橡胶组合物的混合物组成，其含有少部分富含苯乙烯的苯乙烯/异戊二烯弹性体
公开(公告)号：US06812277B2
公开(公告)日：2004-11-02
申请号：US10000730
申请日：2001-10-31
申请人： David John Zanzig , Adel Farhan Halasa , Chad Aaron Jasiunas
发明人： David John Zanzig , Adel Farhan Halasa , Chad Aaron Jasiunas
IPC分类号： C08L906
CPC分类号： C08L9/00 , C08L9/06 , C08L2666/08
摘要： Pneumatic rubber tire having at least one component or a rubber composition comprised of a major portion of relatively low Tg high cis 1,4-polybutadiene elastomer (BR) and a minor portion of a relatively high Tg, styrene-rich, styrene/isoprene elastomer (SIR) wherein the Tg of said BR is at least 60° C. lower than the Tg of said SIR. Said SIR has a styrene content of at least 30 weight percent. The styrene based units of said SIR are present substantially without large blocks of styrene units. Said BR is a high cis 1,4-polybutadiene having a cis 1,4-content of at least 96 percent and preferably has a branched macrostructure. In one aspect of the invention, said tire component is a tire tread, particularly a circumferential tire tread.
摘要翻译：具有至少一种组分或橡胶组合物的气动橡胶轮胎，其由大部分相对低Tg的高顺式1,4-聚丁二烯弹性体（BR）和少部分相对高的，富含苯乙烯的苯乙烯/异戊二烯弹性体（SIR），其中所述BR的Tg比所述SIR的Tg低至少60℃。所述SIR具有至少30重量％的苯乙烯含量。所述SIR的基于苯乙烯的单元基本上不存在苯乙烯单元的大块。所述BR是具有至少96％的顺式1,4-含量的高顺式1,4-聚丁二烯，优选具有支链宏观结构。在本发明的一个方面，所述轮胎部件是轮胎胎面，特别是周向轮胎胎面。

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