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51. 发明授权

US06180707B2 Stabilizer for tin-coupled elastomers 有权
标题翻译：锡偶合弹性体稳定剂
公开(公告)号：US06180707B2
公开(公告)日：2001-01-30
申请号：US09452228
申请日：1999-12-01
申请人： Wen-Liang Hsu , Adel Farhan Halasa
发明人： Wen-Liang Hsu , Adel Farhan Halasa
IPC分类号： C08K505
CPC分类号： C08K5/057 , C08L15/00
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 metal salt of a cyclic alcohol 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 metal salt of a cyclic alcohol to the tin-coupled rubbery polymer subsequent to the time at which the tin-coupled rubbery polymer is coupled. The use of metal salts of cyclic alcohols does not lead to recycle stream contamination because they do not co-distill with hexane or form compounds during steam-stripping which co-distill with hexane. In other words, the boiling points of these metal salts of cyclic alcohols are very high, so they do not co-distill with hexane and contaminate recycle streams. Additionally, metal salts of cyclic alcohols are considered to be environmentally safe. In fact, sodium mentholate is used as a food additive.
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环状醇的金属盐。本发明更具体地公开了一种改善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，向锡偶合的橡胶状聚合物中加入环状醇的金属盐。使用环醇的金属盐不会导致再循环流污染，因为它们在与己烷共蒸馏的蒸汽汽提过程中不与己烷共蒸馏或形成化合物。换句话说，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。事实上，薄荷酸钠被用作食品添加剂。

52. 发明授权

US6103842A Process and catalyst system for synthesizing random trans SBR with low vinyl microstructure 失效
标题翻译：用于合成具有低乙烯基显微组织的随机反式SBR的工艺和催化剂体系
公开(公告)号：US6103842A
公开(公告)日：2000-08-15
申请号：US72492
申请日：1998-05-04
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Laurie Elizabeth Austin
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Laurie Elizabeth Austin
IPC分类号： B60C1/00 , C08F4/54 , C08F4/56 , C08F236/10 , C08F4/50 , C08F36/06
CPC分类号： C08F236/10 , C08F4/565
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 exothermal polymerizations which consists essentially of (a) an organolithium compound, (b) a barium 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 barium alkoxide and (c) a lithium alkoxide.
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一种用于放热聚合的催化剂体系，其基本上由（a）有机锂化合物，（b）烷氧基钡和（c）醇盐锂组成。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）钡醇盐和（c）醇锂。

53. 发明授权

US5906956A Lithium initiator system 失效
标题翻译：锂引发剂体系
公开(公告)号：US5906956A
公开(公告)日：1999-05-25
申请号：US834787
申请日：1997-04-03
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F4/48 , C08F136/06 , C08F136/08
CPC分类号： C08F136/08 , C08F136/06
摘要： This invention reveals an initiator system which is comprised of (a) a lithium initiator, (b) a sodium alkoxide and (c) a polar modifier; wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 3:1; and wherein the molar ratio of the polar modifier to the lithium initiator is within the range of about 0.25:1 to about 5:1. The subject invention also discloses a process for preparing 3,4-polyisoprene rubber which comprises polymerizing isoprene monomer with a lithium initiator at a temperature which is within the range of about 30.degree. C. to about 100.degree. C. in the presence of a sodium alkoxide and a polar modifier, wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 3:1; and wherein the molar ratio of the polar modifier to the lithium initiator is within the range of about 0.25:1 to about 5:1.
摘要翻译：本发明揭示了一种引发剂体系，其包括（a）锂引发剂，（b）醇钠和（c）极性改性剂; 其中所述醇钠与所述锂引发剂的摩尔比在约0.05:1至约3:1的范围内; 并且其中极性改性剂与锂引发剂的摩尔比在约0.25:1至约5:1的范围内。本发明还公开了一种制备3,4-聚异戊二烯橡胶的方法，该方法包括在钠存在下，在约30℃至约100℃的温度范围内用锂引发剂聚合异戊二烯单体醇盐和极性改性剂，其中烷氧基钠与锂引发剂的摩尔比在约0.05:1至约3:1的范围内; 并且其中极性改性剂与锂引发剂的摩尔比在约0.25:1至约5:1的范围内。

54. 发明授权

US09587060B2 Functionalized rubbery polymers 有权
标题翻译：官能化橡胶聚合物
公开(公告)号：US09587060B2
公开(公告)日：2017-03-07
申请号：US11603719
申请日：2006-11-22
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Jin-Ping Zhou , Teresa Diane Martter
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Jin-Ping Zhou , Teresa Diane Martter
IPC分类号： C08F236/10 , C08F236/12 , C08F212/08 , C08F212/14 , C08K5/548 , C08K3/36 , B60C1/00 , C07C211/27 , C07F7/10 , C08L21/00 , C08L97/00
CPC分类号： C08F236/12 , B60C1/0016 , C07C211/27 , C07F7/10 , C08F212/08 , C08F212/14 , C08F236/10 , C08K3/36 , C08K5/548 , C08L21/00 , C08L97/00 , C08L15/00 , C08F236/06 , C08L2666/26
摘要： This invention discloses a process for the synthesis of a rubbery polymer by emulsion polymerization that comprised polymerizing (1) a conjugated diolefin monomer and (2) a functionalized monomer having the structural formula: wherein the R1 groups can be the same or different and represent hydrogen atoms or alkyl groups containing from 1 to about 8 carbon atoms, wherein R2 represents a hydrogen atom or an alkyl group containing from 1 to about 8 carbon atoms, wherein R3 represents a hydrogen atom or an alkyl group containing from 1 to about 8 carbon atoms, and wherein R4 represents a hydrogen atom or an alkyl group containing from 1 to about 8 carbon atoms, with the proviso that if R3 represent an alkyl group then R4 represents a hydrogen atom, and with the proviso that R4 represents an alkyl group then R3 represents a hydrogen atom, wherein said polymerization is conducted in an aqueous medium, and wherein said polymerization is initiated with a free radical initiator.
摘要翻译：本发明公开了一种功能单体，其用于聚合物，橡胶组合物，轮胎以及制备这种橡胶组合物的方法。所述官能单体具有选自由以下组成的组的结构式：其中R 1基可以相同或不同，表示氢原子或含有1至8个碳原子的烷基，其中R 2表示氢原子或烷基含有1至8个碳原子的基团，其中R 3表示氢原子或含有1至8个碳原子的烷基，其中R 4表示氢原子或含有1至8个碳原子的烷基，条件是如果R 3表示烷基，则R 4表示氢原子，条件是R 4表示烷基，则R 3表示氢原子，并且其中R 5可以相同或不同，表示烷基含有1至8个碳原子的基团。

55. 发明授权

US07825202B2 Potassium based catalyst systems for synthesizing rubbery polymers 有权
标题翻译：用于合成橡胶状聚合物的钾基催化剂体系
公开(公告)号：US07825202B2
公开(公告)日：2010-11-02
申请号：US12248601
申请日：2008-10-09
申请人： John Robert Zuppo, III , Adel Farhan Halasa , Wen-Liang Hsu , Leh-Yeh Hsu, legal representative
发明人： John Robert Zuppo, III , Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： C08F4/44 , C08F4/56 , C08F4/52 , B01J31/14
CPC分类号： B60C1/0016 , C08F36/06 , C08F4/52
摘要： The present invention is directed to a catalyst system for synthesizing rubbery polymers, such as styrene-butadiene rubber, that can be utilized in tire tread rubbers. The catalyst system, in one embodiment, includes an organolithium compound and a potassium alkyl borohydride or potassium alkyl aluminum hydride defined by: (R)3A−(H)K+, wherein A is boron or aluminum, H is hydrogen, K is potassium, and R, which is the same or different, is either H, a C1-C10 alkyl, a C3-C10 cycloalkyl, phenyl, or phenyl substituted C1-C10 alkyl, or a C3-C10 cycloalkyl, with the proviso that at least one R is a C1-C10 alkyl, and further wherein any two R's may optionally be part of a carbocyclic ring. The rubbery polymers can have low to medium vinyl microstructure content, i.e., from about 10% to about 40%, and are useful in tire tread rubber compounds which can exhibit improved wear and tear characteristics.
摘要翻译：本发明涉及可用于轮胎胎面橡胶中的用于合成橡胶状聚合物如丁苯橡胶的催化剂体系。催化剂体系在一个实施方案中包括有机锂化合物和烷基硼氢化钾或烷基氢化铝钾，其定义为：（R）3A-（H）K +，其中A是硼或铝，H是氢，K是钾，和R相同或不同，为H，C 1 -C 10烷基，C 3 -C 10环烷基，苯基或苯基取代的C 1 -C 10烷基或C 3 -C 10环烷基，条件是至少一个 R是C 1 -C 10烷基，并且其中任何两个R可以任选地是碳环的一部分。橡胶状聚合物可以具有低至中等乙烯基微结构含量，即约10％至约40％，并且可用于可显示改善的磨损和撕裂特性的轮胎胎面橡胶化合物。

56. 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。

57. 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。

58. 发明授权

US07528186B2 Silica reinforced rubber composition containing an ionic compound and article having a component thereof 失效
标题翻译：含有离子性化合物的硅橡胶组合物及其成分的制品
公开(公告)号：US07528186B2
公开(公告)日：2009-05-05
申请号：US11455608
申请日：2006-06-19
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Aaron Scott Puhala
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Aaron Scott Puhala
IPC分类号： C08K5/3445 , C08K5/17 , C08K5/50 , C08K5/3432 , B60C5/00
CPC分类号： B60C1/0016 , B60C1/0025 , B60C11/0058 , B60C19/08 , C08K5/19 , C08K5/3445 , C08K5/50 , C08K2201/001 , C08L21/00
摘要： This invention relates to a silica reinforced rubber composition containing an ionic compound and article having a component thereof. The invention particularly relates to an article such as a rubber tire having a component of such rubber composition. Said ionic compound is composed of a combination of an organic cation moiety and an organic or inorganic anion moiety. Said ionic compound is desirably an ionically conductive ionic compound. The invention particularly relates to improvement of one or more physical properties of a rubber composition by an inclusion of such ionic compound and/or providing a path of least electrical resistance for a electrically resistive component of an article such as a tire by an inclusion in the rubber composition of said component of an ionically conductive ionic compound composed of a combination of an organic cation moiety and an organic or inorganic anion moiety.
摘要翻译：本发明涉及一种含有离子化合物的二氧化硅增强橡胶组合物及其组分。本发明特别涉及具有这种橡胶组合物成分的橡胶轮胎的制品。所述离子化合物由有机阳离子部分和有机或无机阴离子部分的组合构成。所述离子化合物理想地是离子导电的离子化合物。本发明特别涉及通过包含这种离子化合物来改善橡胶组合物的一种或多种物理性能和/或通过包含在轮胎中的方式为轮胎制品的电阻部件提供最小电阻的路径由有机阳离子部分和有机或无机阴离子部分的组合构成的离子导电离子化合物的所述组分的橡胶组合物。

59. 发明授权

US07429549B2 Process for improved coupling of rubbery polymers 失效
标题翻译：改进橡胶状聚合物偶联的方法
公开(公告)号：US07429549B2
公开(公告)日：2008-09-30
申请号：US10966192
申请日：2004-10-15
申请人： Adel Farhan Halasa , Wen-Liang Hsu
发明人： Adel Farhan Halasa , Wen-Liang Hsu
IPC分类号： B01J31/00
CPC分类号： C08F297/04 , C08F297/044
摘要： Rubbery polymers made by anionic polymerization can be coupled with tin halides or silicon halides to improve the characteristics of the rubber for use in some applications, such as fire treads. In cases where the rubbery polymer was synthesized utilizing a polar modifier it is difficult to attain a high level of coupling. This invention is based upon the unexpected finding that coupling efficiency can be significantly improved by conducting the coupling reaction in the presence of a lithium salt of a saturated aliphatic alcohol, such as lithium t-amylate. This invention discloses a process for coupling a living rubbery polymer that comprises reacting the living rubbery polymer with coupling agent selected from the group consisting of tin halides and silicon halides in the presence of a lithium salt of a saturated aliphatic alcohol. The lithium salt of the saturated aliphatic alcohol can be added immediately prior to the coupling reaction or it can be present throughout the polymerization and coupling process. Lithium t-amylate reacts with water to form t-amyl alcohol during steam stripping. Since t-amyl alcohol forms an azeotrope with hexane, it co-distills with hexane and can contaminate recycle feed streams. This problem of recycle stream contamination can be solved by using metal salts of cyclic alcohols that do not co-distill with hexane or form compounds during steam stripping which co-distill with hexane. Thus, the use of metal salts of cyclic alcohols is preferred for this reason and because they are considered to be environmentally safe.
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或卤化硅偶联，以改善用于某些应用中的橡胶的特性，例如防火踏面。在使用极性改性剂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，通过在饱和脂肪醇的锂盐如叔戊醇锂的存在下进行偶联反应可以显着改善偶联效率。本发明公开了一种使活性橡胶状聚合物偶合的方法，其包括在饱和脂肪醇的锂盐存在下使活性橡胶状聚合物与选自锡卤化物和卤化硅的偶联剂反应。饱和脂肪醇的锂盐可以在偶联反应之前立即加入，或者可以在整个聚合和偶联过程中存在。在蒸汽汽提期间，叔戊醇钠与水反应形成叔戊醇。由于叔戊醇与己烷形成共沸物，因此与己烷共蒸馏，可能污染再循环进料流。循环流污染的这个问题可以通过使用在与汽油共蒸馏的汽提过程中不与己烷共蒸馏或形成化合物的环醇的金属盐来解决。因此，由于这个原因，优选使用环状醇的金属盐，并且因为它们被认为是环境安全的。

60. 发明申请

US20070293610A1 Silica reinforced rubber composition containing an ionic compound and article having a component thereof 失效
标题翻译：含有离子性化合物的硅橡胶组合物及其成分的制品
公开(公告)号：US20070293610A1
公开(公告)日：2007-12-20
申请号：US11455608
申请日：2006-06-19
申请人： Adel Farhan Halasa , Wen-Liang Hsu , Aaron Scott Puhala
发明人： Adel Farhan Halasa , Wen-Liang Hsu , Aaron Scott Puhala
IPC分类号： C08K5/52
CPC分类号： B60C1/0016 , B60C1/0025 , B60C11/0058 , B60C19/08 , C08K5/19 , C08K5/3445 , C08K5/50 , C08K2201/001 , C08L21/00
摘要： This invention relates to a silica reinforced rubber composition containing an ionic compound and article having a component thereof. The invention particularly relates to an article such as a rubber tire having a component of such rubber composition. Said ionic compound is composed of a combination of an organic cation moiety and an organic or inorganic anion moiety. Said ionic compound is desirably an ionically conductive ionic compound. The invention particularly relates to improvement of one or more physical properties of a rubber composition by an inclusion of such ionic compound and/or providing a path of least electrical resistance for a electrically resistive component of an article such as a tire by an inclusion in the rubber composition of said component of an ionically conductive ionic compound composed of a combination of an organic cation moiety and an organic or inorganic anion moiety.
摘要翻译：本发明涉及一种含有离子化合物的二氧化硅增强橡胶组合物及其组分。本发明特别涉及具有这种橡胶组合物成分的橡胶轮胎的制品。所述离子化合物由有机阳离子部分和有机或无机阴离子部分的组合构成。所述离子化合物理想地是离子导电的离子化合物。本发明特别涉及通过包含这种离子化合物来改善橡胶组合物的一种或多种物理性能和/或通过包含在轮胎中的方式为诸如轮胎的制品的电阻部件提供最小电阻的路径由有机阳离子部分和有机或无机阴离子部分的组合构成的离子导电离子化合物的所述组分的橡胶组合物。

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