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1. 发明授权

US07354985B2 Fluorinated thermoset polyurethane elastomers prepared from polyether prepolymers formed from mono-substituted fluorinated oxetane monomers 有权
标题翻译：由由单取代的氟代氧杂环丁烷单体形成的聚醚预聚物制备的氟化热固性聚氨酯弹性体
公开(公告)号：US07354985B2
公开(公告)日：2008-04-08
申请号：US10678663
申请日：2003-10-03
申请人： Aslam A. Malik , Thomas G. Archibald
发明人： Aslam A. Malik , Thomas G. Archibald
IPC分类号： C08G18/28 , C07D305/00
CPC分类号： C08G65/226 , C07D305/06 , C08G18/10 , C08G18/5015 , C08G18/6677 , C08G65/00 , C08G65/18 , C08G65/20 , C08G18/32
摘要： This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains. Additionally, the fluorinated oxetane monomers can be copolymerized with non-fluorinated monomers such as tetrahydrofuran to give polyether prepolymers with improved hydrocarbon compatibility. These prepolymers are polydisperse and exhibit number average molecular weights from 5,000 to about 50,000. These prepolymers are amorphous oils with primary hydroxy end-groups and thus function efficiently as the soft block for the synthesis of a variety of thermoset/thermoplastic elastomers and plastics having the characteristics of very low surface energy, high hydrophobicity, low glasss transition temperature and low coefficient of friction. The polyurethanes derived from the prepolymers of this invention are elastomeric and, in addition to the above characteristics, exhibit high moisture resistance, high tear strength and excellent adhesion to a variety of substrates.
摘要翻译：本申请涉及由具有氟化烷氧基亚甲基侧链的单取代的氧杂环丁烷单体衍生的新的氟化聚合物和预聚物以及制备这些组合物的方法。具有氟化烷氧基亚甲基侧链的单取代氟化氧杂环丁烷单体通过氟化烷氧化物与3-卤代甲基-3-甲基氧杂环丁烷预先单体或3-羟甲基-3-甲基氧杂环丁烷预先单体的芳基磺酸酯衍生物的反应以高收率制备。还公开了通过易于商业化的简单高产率工艺制备单取代的3-溴甲基-3-甲基环氧乙烷预先单体。本发明的氟化氧杂环丁烷单体可以在路易斯酸和多羟基化合物的存在下容易地均相/共聚，得到具有氟化烷氧基亚甲基侧链的羟基封端的聚醚预聚物。此外，氟化氧杂环丁烷单体可以与非氟化单体如四氢呋喃共聚，得到具有改进的烃相容性的聚醚预聚物。这些预聚物是多分散体，其数均分子量为5,000至约50,000。这些预聚物是具有初级羟基端基的无定形油，因此作为用于合成各种具有非常低的表面能，高疏水性，低玻璃化转变温度和低的特性的各种热固性/热塑性弹性体和塑料的软块有效地起作用摩擦系数。衍生自本发明的预聚物的聚氨酯是弹性体的，并且除了上述特征之外，还显示出高耐湿性，高撕裂强度和对各种基材的优异粘合性。

2. 发明授权

US06825316B2 Amorphous polyether glycols based on bis-substituted oxetane and tetrahydrofuran monomers 失效
标题翻译：基于双取代的氧杂环丁烷和四氢呋喃单体的无定形聚醚二醇
公开(公告)号：US06825316B2
公开(公告)日：2004-11-30
申请号：US10291139
申请日：2002-11-08
申请人： Aslam A. Malik , Thomas G. Archibald , Roland P. Carlson , Kenneth J. Wynne , Edward N. Kresge
发明人： Aslam A. Malik , Thomas G. Archibald , Roland P. Carlson , Kenneth J. Wynne , Edward N. Kresge
IPC分类号： C08G6522
CPC分类号： C08G18/5015 , C08G65/18 , C08G65/226
摘要： This invention is directed to mono- and bis-substituted oxetane monomers having fluorinated alkoxymethylene side chains, hydroxy-terminated prepolymers derived from these mono- and bis-substituted oxetane monomers and tetrahydrofuran (THF), and polymers produced from these prepolymers, as well as the synthesis processes associated with each, and the use of the monomers, prepolymers and ultimate polymers, both directly and as components of numerous compositions.
摘要翻译：本发明涉及具有氟化烷氧基亚甲基侧链的单取代和双取代的氧杂环丁烷单体，由这些单取代和双取代的氧杂环丁烷单体衍生的羟基封端的预聚物和四氢呋喃（THF），以及由这些预聚物制备的聚合物与各自相关的合成方法，以及单体，预聚物和极性聚合物的使用，直接地和作为许多组合物的组分。

3. 发明授权

US06548706B2 Preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl) -p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines 有权
标题翻译：制备2S，3S-N-异丁基-N-（2-羟基-3-氨基-4-苯基丁基） - 对硝基苯磺酰胺盐酸盐和2-羟基-1,3-二胺的其它衍生物
公开(公告)号：US06548706B2
公开(公告)日：2003-04-15
申请号：US09747372
申请日：2000-12-22
申请人： Aslam A. Malik , Hasan Palandoken , Joy A. Stringer , Roland P. Carlson , John Leach , Thomas G. Archibald , Robert G. Miotke
发明人： Aslam A. Malik , Hasan Palandoken , Joy A. Stringer , Roland P. Carlson , John Leach , Thomas G. Archibald , Robert G. Miotke
IPC分类号： C07C20908
CPC分类号： C07C269/06 , C07C303/40 , C07C311/18 , C07C271/20
摘要： The present invention provides a new process for the preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride, wherein this compound is prepared directly from the chloromethylalcohol. Importantly, the process of the present invention results in higher yields of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride without sacrificing its purity. The processes of the present inventin can be used to prepare not only the 2S,3S-derivative, but also the 2R,3S-, 2S,2R- and the 2R,3R-derivatives.
摘要翻译：本发明提供了制备2S，3S-N-异丁基-N-（2-羟基-3-氨基-4-苯基丁基） - 对硝基苯磺酰胺盐酸盐的新方法，其中该化合物直接由氯甲基醇制备。重要的是，本发明的方法导致2S，3S-N-异丁基-N-（2-羟基-3-氨基-4-苯基丁基） - 对硝基苯磺酰胺盐酸盐的产率较高，而不牺牲其纯度。本发明的方法不仅可以制备2S，3S-衍生物，还可以制备2R，3S-，2S，2R-和2R，3R-衍生物。

4. 发明授权

US5824807A Preparations of azabicylobutane precursors and related compositions 失效
标题翻译：氮杂丁烷前体和相关组合物的制备
公开(公告)号：US5824807A
公开(公告)日：1998-10-20
申请号：US441512
申请日：1995-05-15
申请人： Paritosh R. Dave , Thomas G. Archibald
发明人： Paritosh R. Dave , Thomas G. Archibald
IPC分类号： C07D205/04 , C07D205/00
CPC分类号： C07D205/04
摘要： Azabicylobutane can be produced by reacting azetidines under aqueous conditions to eliminate aza and 3-position substituents to effect cyclization. New azetidinyl compounds are described which can be intermediates in the preparation of the azabicyclobutane.
摘要翻译：氮杂丁烷可以通过在水性条件下使氮杂环丁烷反应以除去氮杂和3-位取代基以实现环化来制备。描述了新的氮杂环丁烷基化合物，其可以是制备氮杂双环丁烷的中间体。

5. 发明授权

US5663289A Preparation and polymerization of initiators containing multiple oxetane rings: new routes to star polymers 失效
标题翻译：含有多个氧杂环丁烷环的引发剂的制备和聚合：新的星形聚合物途径
公开(公告)号：US5663289A
公开(公告)日：1997-09-02
申请号：US330480
申请日：1994-10-28
申请人： Thomas G. Archibald , Roland P. Carlson , Aslam A. Malik , Gerald E. Manser
发明人： Thomas G. Archibald , Roland P. Carlson , Aslam A. Malik , Gerald E. Manser
IPC分类号： C07D305/06 , C08G65/12 , C08G65/18 , C08G65/22 , C08G65/26 , C08G65/04
CPC分类号： C08G65/12 , C07D305/06 , C08G65/18 , C08G65/22 , C08G65/2645
摘要： This invention relates to novel multifunctional oxetanes, i.e., compounds having multiple oxetane groups, which are useful as initiators in the preparation of star polymers and polymer cascades containing energetic groups. In addition, this invention relates to a process for the preparation of star polymers and polymer cascades, whereby novel multifunctional oxetanes act as initiators in the formation of theses polymers. The reaction of these initiators with various propagating, high-energy oxetanes, such as 3,3-bis-(azidomethyl)oxetane (BAMO) and 3-nitratomethyl-3-methyloxetane (NMMO), gives star polymers with varying molecular weights and functionalities. The star polymers and polymer cascades of the present invention are useful as binders in high-energy formulations.
摘要翻译：本发明涉及新的多官能氧杂环丁烷，即具有多个氧杂环丁烷基团的化合物，其可用作制备包含能量基团的星形聚合物和聚合物级联的引发剂。此外，本发明涉及一种制备星形聚合物和聚合物级联的方法，由此新颖的多官能氧杂环丁烷在形成这些聚合物时用作引发剂。这些引发剂与各种繁殖的高能氧杂环丁烷如3,3-双（叠氮甲基）氧杂环丁烷（BAMO）和3-硝基甲基-3-甲基氧杂环丁烷（NMMO）的反应得到具有不同分子量和官能度的星形聚合物。本发明的星形聚合物和聚合物级联可用作高能量制剂中的粘合剂。

6. 发明授权

US5463019A Polymers and copolymers from 3-azidomethyl-3-nitratomethyloxetane 失效
标题翻译： 3-叠氮基甲基-3-硝基甲基氧杂环丁烷的聚合物和共聚物
公开(公告)号：US5463019A
公开(公告)日：1995-10-31
申请号：US377572
申请日：1995-01-23
申请人： Gerald E. Manser , Aslam A. Malik , Thomas G. Archibald
发明人： Gerald E. Manser , Aslam A. Malik , Thomas G. Archibald
IPC分类号： C07D305/06 , C08G65/22 , C07C43/10
CPC分类号： C08G65/22 , C07D305/06
摘要： 3-Azidomethyl-3-nitratomethyloxetane, a novel oxetane compound, is used as a monomer for the formation of homopolymers and copolymers with other known energetic oxetane monomers. The polyethers of the present invention can be subsequently cured to form elastomers suitable for use as energetic binders in propellant formulations or the like.
摘要翻译： 3-叠氮基甲基-3-硝基甲基氧杂环丁烷是新型的氧杂环丁烷化合物，用作与其它已知的能量大的氧杂环丁烷单体形成均聚物和共聚物的单体。本发明的聚醚可随后固化以形成适合用作推进剂配方等中的高能粘合剂的弹性体。

7. 依法登记的发明

USH1223H Method of making fluorodinitroethanol (FDNE) 失效
标题翻译：氟代丁醇（FDNE）制备方法
公开(公告)号：USH1223H
公开(公告)日：1993-08-03
申请号：US702215
申请日：1991-05-17
申请人： Thomas G. Archibald , Nghi Van Nguyen , Kurt Baum
发明人： Thomas G. Archibald , Nghi Van Nguyen , Kurt Baum
IPC分类号： C07C205/26 , C07C31/34 , C07C205/00
CPC分类号： C07C201/10 , C07C201/12 , C07C205/51 , C07C205/08 , C07C205/26
摘要： A method of producing FDNE using readily available fluoroolefins as a fluorine source.

8. 发明授权

US6011177A Process for 4-sulfonamidolphenyl hydrazines 失效
标题翻译： 4-磺酰氨基苯基肼的方法
公开(公告)号：US6011177A
公开(公告)日：2000-01-04
申请号：US978965
申请日：1997-11-26
申请人： Thomas G. Archibald , James C. Barnard
发明人： Thomas G. Archibald , James C. Barnard
IPC分类号： C07C303/40 , C07C311/39
CPC分类号： C07C303/40
摘要： 4-Sulfonamidophenyl hydrazines are prepared by reaction between the hydrazine, optionally substituted, and the corresponding 4-substituted benzenesulfonamides, where the 4-substitution is an appropriate leaving group, in the presence of water and the absence of dimethyl sulfoxide as a solvent. The result is a product of unusually high purity.
摘要翻译：通过在任选取代的肼和相应的4-取代的苯磺酰胺（其中4-取代是合适的离去基团）在水和不存在二甲基亚砜作为溶剂的条件下反应来制备4-磺酰胺基苯肼。结果是异常高纯度的产品。

9. 发明授权

US5489700A 3-Azidomethyl-3-nitratomethyloxetane 失效
标题翻译： 3-叠氮基甲基-3-硝基甲基氧杂环丁烷
公开(公告)号：US5489700A
公开(公告)日：1996-02-06
申请号：US469329
申请日：1995-06-05
申请人： Gerald E. Manser , Aslam A. Malik , Thomas G. Archibald
发明人： Gerald E. Manser , Aslam A. Malik , Thomas G. Archibald
IPC分类号： C07D305/06 , C08G65/22 , C07D305/00
CPC分类号： C08G65/22 , C07D305/06
摘要： 3-Azidomethyl-3-nitratomethyloxetane, a novel oxetane compound, is used as a monomer for the formation of homopolymers and copolymers with other known energetic oxetane monomers. The polyethers of the present invention can be subsequently cured to form elastomers suitable for use as energetic binders in propellant formulations or the like.
摘要翻译： 3-叠氮基甲基-3-硝基甲基氧杂环丁烷是新型的氧杂环丁烷化合物，用作与其它已知的能量大的氧杂环丁烷单体形成均聚物和共聚物的单体。本发明的聚醚可随后固化以形成适合用作推进剂配方等中的高能粘合剂的弹性体。

10. 发明授权

US5468841A Polymerization of energetic, cyclic ether monomers using boron trifluoride tetrahydrofuranate 失效
标题翻译：使用三氟化硼四氢化物聚合能量较高的环醚单体
公开(公告)号：US5468841A
公开(公告)日：1995-11-21
申请号：US226919
申请日：1994-04-13
申请人： Aslam A. Malik , Thomas G. Archibald , Roland P. Carlson , Gerald E. Manser
发明人： Aslam A. Malik , Thomas G. Archibald , Roland P. Carlson , Gerald E. Manser
IPC分类号： C08G65/22
CPC分类号： C08G65/22
摘要： The present invention provides an improved method of carrying out cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO). Such cyclic ether monomers are polymerized with an initiator precursor (i.e., an alcohol) and boron trifluoride tetrahydrofuranate (BF.sub.3 .cndot.THF). It has been discovered that when boron trifluoride tetrahydrofuranate is used as a catalyst in the cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO), polymers are produced that have improved functionality and low poly-dispersity. The polymers formed using the method of the present invention are useful for forming cross-linked elastomers which, in turn, are useful for forming elastomeric binders for high-energy compositions, such as propellants, explosives, gasifiers or the like.
摘要翻译：本发明提供了用高能吸电子侧基（例如BAMO和NMMO）取代的环醚单体进行阳离子聚合的改进方法。这种环醚单体与引发剂前体（即醇）和三氟化硼四氢硼酸酯（BF 3，THF）聚合。已经发现，当用高能吸电子侧基（例如BAMO和NMMO）取代的环醚单体的阳离子聚合中使用四氟化硼作为催化剂时，产生具有改进的官能度和低的聚合物多分散性使用本发明的方法形成的聚合物可用于形成交联的弹性体，其又可用于形成用于高能组合物的弹性体粘合剂，例如推进剂，爆炸物，气化器等。

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