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11. 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。

12. 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.

13. 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

14. 发明授权

US06825306B2 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：US06825306B2
公开(公告)日：2004-11-30
申请号：US10661914
申请日：2003-09-12
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F21214
CPC分类号： C08C19/44 , C08F236/10 , C08F236/14 , Y10T152/10495
摘要： The present invention relates to a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer of the structural formula: wherein the R′ groups in repeat units and in different repeat units can be the same or different and represent hydrogen atoms or alkyl groups containing from 1 to about 4 carbon atoms, wherein x represents an integer from 1 to about 10, and wherein the R groups in repeat units and in different repeat units can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms or alkoxy groups containing from 1 to about 10 carbon atoms.
摘要翻译：本发明涉及一种橡胶状聚合物，其由衍生自（1）至少一种共轭二烯烃单体的重复单元和（2）至少一种具有以下结构式的官能化单体组成：其中重复单元中的R'基团并且不同的重复单元可以相同或不同，并且表示氢原子或含有1至约4个碳原子的烷基，其中x表示1至约10的整数，并且其中R基以重复单元和不同重复单元可以相同或不同，表示含有1至约10个碳原子的烷基或含有1至约10个碳原子的烷氧基。

15. 发明授权

US06753447B2 Functionalized monomers for synthesis of rubbery polymers 有权
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：US06753447B2
公开(公告)日：2004-06-22
申请号：US10370969
申请日：2003-02-20
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Naoya Ogata
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Naoya Ogata
IPC分类号： C07C20908
CPC分类号： C07D295/03 , C07D227/04 , C08C19/44 , C08F36/04 , C08F236/10 , C08F236/14 , C08F4/48 , C08F4/50
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，制备含有仲胺的乙烯基卤化物，其具有选自R和R' 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）使包含乙烯基卤的仲胺与乙烯基卤化镁反应以制备具有结构式R的R 1和R 2的单体可以相同或不同，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。

16. 发明授权

US06515087B2 Synthesis of elastomers having low hysteresis 失效
标题翻译：具有低滞后性的弹性体的合成
公开(公告)号：US06515087B2
公开(公告)日：2003-02-04
申请号：US10016069
申请日：2001-12-06
申请人： Wen-Liang Hsu , Adel Farhan Halasa , Scott McDowell Christian , Michael Lester Kerns
发明人： Wen-Liang Hsu , Adel Farhan Halasa , Scott McDowell Christian , Michael Lester Kerns
IPC分类号： C08F448
CPC分类号： C08F36/04 , C08F4/48
摘要： It is important for rubbery polymers that are used in tires, hoses, power transmission belts and other industrial products to have good compatibility with fillers, such as carbon black, silica, clay (including organoclays), and mixtures thereof. To attain improved interaction with fillers such rubbery polymers can be functionalized with various compounds, such as amines. The present invention discloses a process for synthesizing a rubbery polymer that is functionalized to attain improved compatibility with fillers. The present invention more specifically disclosed a process for synthesizing a rubbery polymer that comprises (1) continuously charging (a) a conjugated diolefin monomer, (b) an organolithium compound, and (c) an amine compound into a polymerization zone, wherein the amine compound is selected from the group consisting of alkyl, dialkyl, cycloalkyl or dicycloalkyl amine compounds of the general formula: wherein R represents an alkyl group, a cycloalkyl group, or an alkaryl group containing from 1 to about 12 carbon atoms, and cyclic amine compounds of the general formula: wherein R2 represents a divalent alkylene, bicycloalkane, substituted alkylene, oxy- or N-alkylamino-alkylene group containing from about 3 to about 16 methylene groups; (2) allowing the conjugated diolefin monomer to polymerize in the polymerization zone to produce the rubbery polymer; and (3) continuously withdrawing the rubbery polymer from the polymerization zone.
摘要翻译：用于轮胎，软管，动力传动带和其他工业产品中的橡胶状聚合物与炭黑，二氧化硅，粘土（包括有机粘土）等填料具有良好的相容性是重要的，以及它们的混合物。为了获得与填料的改善的相互作用，这种橡胶状聚合物可以用各种化合物如胺官能化。本发明公开了一种合成橡胶状聚合物的方法，其被官能化以获得与填料相容性的改善。本发明更具体地公开了一种合成橡胶状聚合物的方法，其包括（1）将共轭二烯烃单体，（b）有机锂化合物和（c）胺化合物连续地加入到聚合区中，其中胺化合物选自以下通式的烷基，二烷基，环烷基或二环烷基胺化合物：其中R表示烷基，环烷基或含有1至约12个碳原子的烷芳基，以及环胺化合物其中R2表示含有约3至约16个亚甲基的二价亚烷基，双环烷烃，取代的亚烷基，氧基或N-烷基氨基 - 亚烷基; （2）使共轭二烯烃单体在聚合区中聚合以产生橡胶状聚合物; 和（3）从聚合区域连续取出橡胶状聚合物。

17. 发明授权

US06350807B1 Silica-reinforced tire tread rubber 失效
标题翻译：二氧化硅增强轮胎胎面橡胶
公开(公告)号：US06350807B1
公开(公告)日：2002-02-26
申请号：US09616270
申请日：2000-07-14
申请人： Edward John Blok , Paul Harry Sandstrom , Wen-Liang Hsu , Adel Farhan Halasa , John Joseph Andre Verthe , Raymond Robert DiRossi
发明人： Edward John Blok , Paul Harry Sandstrom , Wen-Liang Hsu , Adel Farhan Halasa , John Joseph Andre Verthe , Raymond Robert DiRossi
IPC分类号： C08K334
CPC分类号： C08L9/00 , B60C1/0016 , C08K3/04 , C08K3/36 , C08K5/0016 , C08L7/00 , C08L15/00 , Y02T10/862 , C08L2666/08
摘要： The present invention relates to a tire tread compound that is highly loaded with silica. This compound offers the advantages of silica compounding without the need for solution SBR. More specifically, the tire tread rubber formulations of this invention offer an excellent combination of traction, treadwear and rolling resistance characteristics. The subject invention 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; wherein the tread is comprised of (1) 5 phr to 40 phr of a polyisoprene rubber selected from the group consisting of natural rubber and synthetic polyisoprene, (2) 20 phr to 60 phr of high vinyl polybutadiene rubber having a glass transition temperature which is within the range of −40° C. to 10° C., (3) 20 phr to 60 phr of tin-coupled isoprene-butadiene rubber having a glass transition temperature which is within the range of −90° C. to −70° C., (4) 30 phr to 90 phr of silica, (5) 5 phr to 50 phr of carbon black, (6) 2 phr to 50 phr of processing oil and (7) 0.5 phr to 15 phr of a silica coupling agent.
摘要翻译：本发明涉及高度负载二氧化硅的轮胎胎面胶。该化合物具有二氧化硅复合的优点，无需溶液SBR。更具体地，本发明的轮胎胎面橡胶配方提供牵引力，胎面磨损和滚动阻力特性的优异组合。本发明公开了一种轮胎，其由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以及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构成; 其中所述胎面适于与地面接触; 其中胎面由（1）5phr至40phr的选自天然橡胶和合成聚异戊二烯的聚异戊二烯橡胶，（2）20phr至60phr的玻璃化转变温度为20phr至60phr的高乙烯基聚丁二烯橡胶在-40℃至10℃的范围内，（3）20phr至60phr的锡偶合异戊二烯 - 丁二烯橡胶，其玻璃化转变温度在-90℃至-70℃的范围内（4）30phr至90phr的二氧化硅，（5）5phr至50phr的炭黑，（6）2phr至50phr的加工油和（7）0.5phr至15phr的二氧化硅偶联剂。

18. 发明授权

US6140434A Synthesis of high vinyl rubber 有权
标题翻译：高乙烯基橡胶的合成
公开(公告)号：US6140434A
公开(公告)日：2000-10-31
申请号：US227367
申请日：1999-01-08
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F2/38 , C08F4/46 , C08F4/48 , C08F36/04 , C08F136/04
CPC分类号： C08F36/04
摘要： Metal salts of saturated aliphatic alcohols can be used as modifiers in lithium initiated solution polymerizations of diene monomers into rubbery polymers. Sodium t-amylate is a preferred modifiers because of its exceptional solubility in non-polar aliphatic hydrocarbon solvents that are employed as the medium for such solution polymerizations. However, using sodium t-amylate as the polymerization modifier in commercial operations where recycle is required can lead to certain problems. These problems arise due to the fact that sodium t-amylate reacts with water to form t-amyl alcohol during steam stripping in the polymer finishing step. Since t-amyl alcohol forms an azeotrope with hexane, it co-distills with hexane and thus contaminates the feed stream. The present invention solves the problem of recycle stream contamination. This invention is based upon the discovery of highly effective modifiers that do not co-distill with hexane or-form-compounds during steam stripping which co-distill with hexane. The modifiers of this invention are metal salts of cyclic alcohols. Since the boiling points of these metal salts of cyclic alcohols are very high, they do not co-distill with hexane and contaminate recycle streams. Additionally, metal salts of cyclic alcohols are considered to be environmentally safe. The, subject invention more specifically discloses an initiator system which is comprised of (a) a lithium initiator, (b) a metal salt of a cyclic alcohol, and (c) a polar modifier.
摘要翻译：饱和脂族醇的金属盐可用作二烯单体进入橡胶状聚合物的锂引发溶液聚合中的改性剂。由于在用于这种溶液聚合的介质的非极性脂族烃溶剂中具有优异的溶解度，因此，叔戊醇钠是优选的改性剂。然而，在需要再循环的商业操作中使用叔戊醇钠作为聚合改性剂可能导致某些问题。这些问题是由于在聚合物整理步骤中的蒸汽汽提期间，叔戊醇钠与水反应形成叔戊醇的事实。由于叔戊醇与己烷形成共沸物，因此与己烷共蒸馏，从而污染进料流。本发明解决了循环流污染的问题。本发明基于在蒸汽汽提过程中与己烷共沸蒸馏而不与己烷或形式化合物共蒸馏的高效改性剂的发现。本发明的改性剂是环醇的金属盐。由于这些环状醇的金属盐的沸点非常高，因此它们不与己烷共蒸馏并污染再循环物流。此外，环醇的金属盐被认为是环境安全的。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，（b）环状醇的金属盐和（c）极性改性剂。

19. 发明授权

US5994448A High performance tire tread rubber composition 失效
标题翻译：高性能轮胎胎面胶组成
公开(公告)号：US5994448A
公开(公告)日：1999-11-30
申请号：US133503
申请日：1998-08-12
申请人： Edward John Blok , Paul Harry Sandstrom , Wen-Liang Hsu , Adel Farhan Halasa
发明人： Edward John Blok , Paul Harry Sandstrom , Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： B60C1/00 , C08C19/44 , C08L9/00 , C08K3/00
CPC分类号： C08C19/44 , B60C1/0016 , C08L9/00 , C08K3/36 , C08L7/00 , C08L9/06
摘要： This invention relates to a tire tread compound that can be used in manufacturing tires having outstanding traction characteristics without compromising treadwear and rolling resistance. The tire tread compounds of this invention are made utilizing an isoprene-butadiene rubber having a high glass transition temperature and having SnR.sub.3 end groups, wherein R represents an alkyl group, such as a tertiary-butyl group. These isoprene-butadiene rubbers are made by reacting an isoprene-butadiene rubber having a glass transition temperature which is within the range of about -50.degree. C. to about 0.degree. C. with a tin compound of the formula SnR.sub.3 X, wherein R represents an alkyl group and wherein X represents a halogen. This invention more specifically discloses a tire tread rubber composition which is comprised of (1) about 60 phr to about 95 phr of an isoprene-butadiene rubber having a glass transition temperature which is within the range of about -50.degree. C. to about 0.degree. C. and having --SnR.sub.3 end groups, (2) about 5 phr to about 30 phr of natural rubber and (3) up to about 25 phr of a rubbery polymer having a low glass transition temperature which is within the range of about -85.degree. C. to about -55.degree. C., with the proviso that the total amount of the natural rubber and the rubbery polymer having a low glass transition temperature does not exceed about 40 phr. The rubbery polymer having a low glass transition temperature will typically be high cis-1,4-polybutadiene, isoprene-butadiene rubber, styrene-butadiene rubber or styrene-isoprene-butadiene rubber.
摘要翻译：本发明涉及一种轮胎胎面胶，其可用于制造具有优异牵引特性的轮胎，而不损害胎面和滚动阻力。本发明的轮胎胎面胶料采用高玻璃化转变温度的异戊二烯 - 丁二烯橡胶制成，并具有SnR 3端基，其中R表示烷基，如叔丁基。这些异戊二烯 - 丁二烯橡胶通过使玻璃化转变温度在约-50℃至约0℃范围内的异戊二烯 - 丁二烯橡胶与式SnR 3 X的锡化合物反应制备，其中R表示烷基，其中X表示卤素。本发明更具体地公开了一种轮胎胎面橡胶组合物，其包含（1）约60phr至约95phr的玻璃化转变温度在约-50℃至约0的范围内的异戊二烯 - 丁二烯橡胶具有-SnR 3端基，（2）约5phr至约30phr的天然橡胶和（3）至多约25phr的玻璃化转变温度低于约 - 约25phr的橡胶状聚合物， 85℃至约-55℃，条件是具有低玻璃化转变温度的天然橡胶和橡胶状聚合物的总量不超过约40phr。具有低玻璃化转变温度的橡胶状聚合物通常是高顺式-1,4-聚丁二烯，异戊二烯 - 丁二烯橡胶，苯乙烯 - 丁二烯橡胶或苯乙烯 - 异戊二烯 - 丁二烯橡胶。

20. 发明授权

US5981639A Stabilization of tin-coupled polymers 失效
标题翻译：锡偶合聚合物的稳定化
公开(公告)号：US5981639A
公开(公告)日：1999-11-09
申请号：US58572
申请日：1998-04-10
申请人： Wen-Liang Hsu , Adel Farhan Halasa
发明人： Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： C08C19/44 , C08K5/04 , C08K5/17 , C08K5/34 , C08K5/35 , C08K5/09
CPC分类号： C08C19/44 , C08K5/17 , C08K5/34
摘要： The process of this invention can be utilized to stabilize tin-coupled rubbery polymers. This process involves adding a chelating diamine or a sodium alkoxide to the rubbery polymer after the tin coupling has been carried out. This invention more specifically discloses a process for improving the stability of a tin-coupled rubbery polymer which comprises adding a sodium alkoxide to the tin-coupled rubbery polymer subsequent to the time at which the tin-coupled rubbery polymer is coupled. Sodium alkoxide is a representative example of a sodium alkoxide that can be used to stabilize the tin-coupled rubbery polymer.
摘要翻译：本发明的方法可用于稳定锡偶联的橡胶状聚合物。该方法包括在进行锡偶合之后向橡胶状聚合物中加入螯合二胺或醇钠。本发明更具体地公开了一种改进锡偶合橡胶状聚合物的稳定性的方法，该方法包括在锡偶合的橡胶状聚合物偶合的时间之后向锡偶联的橡胶状聚合物中加入醇钠。烷氧基钠是可用于稳定锡偶联橡胶状聚合物的烷醇钠的代表性实例。

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