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1. 发明授权

US08198461B2 Process for the preparation of 3-cyano-1,2,4-triazoles 有权
标题翻译：制备3-氰基-1,2,4-三唑的方法
公开(公告)号：US08198461B2
公开(公告)日：2012-06-12
申请号：US12437711
申请日：2009-05-08
申请人： Der-Shing Huang , Benjamin Mendoza , Aslam A. Malik
发明人： Der-Shing Huang , Benjamin Mendoza , Aslam A. Malik
IPC分类号： C07D249/10
CPC分类号： C07D233/12 , C07D241/24 , C07D249/10
摘要： The present invention provides compounds and methods that can be used to convert 1,2,4-triazole-3-carboxamides to the corresponding 3-cyano-1,2,4-triazoles reliably in one step, with high yields and without the need for elaborate purification.
摘要翻译：本发明提供可以以高产率和不需要在一个步骤中可靠地将1,2,4-三唑-3-甲酰胺转化为相应的3-氰基-1,2,4-三唑的化合物和方法精心制作纯化。

2. 发明授权

US07414135B2 Process for halomethyl ethers of hydroxyiminomethyl quaternary pyridinium salts 有权
标题翻译：羟基亚氨基甲基季吡啶盐的卤代甲基醚的方法
公开(公告)号：US07414135B2
公开(公告)日：2008-08-19
申请号：US11133740
申请日：2005-05-19
申请人： Der-Shing Huang , George R. Gettys , Olivier Dapremont , Aslam A. Malik
发明人： Der-Shing Huang , George R. Gettys , Olivier Dapremont , Aslam A. Malik
IPC分类号： C07D401/02
CPC分类号： C07D213/53 , C07D213/81
摘要： A halide salt of a 1-(hydroxyiminomethyl-1-pyridino)-3-(halomethyl)-2-oxapropane is prepared by adding a pyridinealdoxime to a bis-halomethylether in such a manner that the bis-halomethylether is maintained in excess throughout the addition. This procedure produces the halide salt of a 1-(hydroxyiminomethyl-1-pyridino)-3-(halomethyl) -2-oxapropanein high yield and purity, which facilitates its use as an intermediate in the manufacture of an asymmetrically substituted 1,3-di (1-pyridino)-2-oxapropane, a class of compounds that are generally useful antidotes to various toxic agents. A prominent member of the class is the dimethylsulfonate salt of 1-(2-hydroxyiminomethyl-1-pyridino)-3 -(4-carbamoyl-1-pyridino)-2-oxapropane. The use of mercaptoalkyl-functionalized polymers is disclosed as a preferred metal ion scavenger for a final purification step in the manufacture of these compounds.
摘要翻译：通过向双卤代甲醚中加入吡啶醛肟制备1-（羟基亚氨基甲基-1-吡啶基）-3-（卤代甲基）-2-氧杂丙烷的卤化物盐，使双 - 卤代甲醚在整个过程中保持过量加成。该方法产生1-（羟基亚氨基甲基-1-吡啶基）-3-（卤代甲基）-2-氧杂丙烷的卤化物盐，其产率和纯度高，这有助于其用作制备不对称取代的1,3- 二（1-吡啶基）-2-氧杂丙烷，一类通常用于各种毒性剂的解毒剂的化合物。该类的突出成员是1-（2-羟基亚氨基甲基-1-吡啶基）-3-（4-氨基甲酰基-1-吡啶基）-2-氧杂丙烷的二甲基磺酸盐。公开了使用巯基烷基官能化聚合物作为优选的金属离子清除剂，用于制造这些化合物的最终纯化步骤。

3. 发明授权

US5668251A Preparation of co-prepolymers from mono-substituted fluorinated monomers and tetrahydrofuran 失效
标题翻译：由单取代氟化单体和四氢呋喃制备共预聚物
公开(公告)号：US5668251A
公开(公告)日：1997-09-16
申请号：US539405
申请日：1995-10-05
申请人： Aslam A. Malik , Roland P. Carlson
发明人： Aslam A. Malik , Roland P. Carlson
IPC分类号： C07B61/00 , C07D305/06 , C08G18/10 , C08G18/50 , C08G18/66 , C08G65/00 , C08G65/18 , C08G65/20 , C08G65/22 , C09D175/06 , C07C41/01
CPC分类号： C08G65/226 , C07D305/06 , C08G18/10 , C08G18/5015 , C08G18/6677 , C08G65/00 , C08G65/18 , C08G65/20
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。

4. 发明授权

US5668250A Polyether coprepolymers formed from mono-substituted fluorinated oxetane monomers and tetrahydrofuran 失效
标题翻译：由单取代的氟代氧杂环丁烷单体和四氢呋喃形成的聚醚共聚物
公开(公告)号：US5668250A
公开(公告)日：1997-09-16
申请号：US483219
申请日：1995-06-07
申请人： Aslam A. Malik
发明人： Aslam A. Malik
IPC分类号： C07B61/00 , C07D305/06 , C08G18/10 , C08G18/50 , C08G18/66 , C08G65/00 , C08G65/18 , C08G65/20 , C08G65/22 , C09D175/06 , C07C43/12 , C07C43/13
CPC分类号： C08G65/226 , C07D305/06 , C08G18/10 , C08G18/5015 , C08G18/6677 , C08G65/00 , C08G65/18 , C08G65/20
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。

5. 发明授权

US5637772A Fluorinated diamines and polymers formed therefrom 失效
标题翻译：氟化二胺和由其形成的聚合物
公开(公告)号：US5637772A
公开(公告)日：1997-06-10
申请号：US532382
申请日：1995-09-22
申请人： Aslam A. Malik , Roland P. Carlson
发明人： Aslam A. Malik , Roland P. Carlson
IPC分类号： C07C217/42 , C08G18/38 , C08G59/30 , C08G59/50 , C07C211/10
CPC分类号： C07C217/42 , C08G18/3814 , C08G59/30 , C08G59/504
摘要： The present invention provides fluorinated diamines and polymers formed therefrom, such as polyureas, polyurethane ureas, polyamides, polyimides, etc. The fluorinated diamines of the present invention are highly nucleophilic and are structured to provide polymeric materials having optimum surface properties. In the fluorinated diamines of the present invention, the end groups are primary amino groups which are substantially removed from the perfluoroalkyl groups. Moreover, the fluorine is present in the side chains which allows the fluorocarbon segments to migrate to the polymer/air interface, thereby providing polymer surfaces with high fluorine concentrations. As such, the polymers formed from the fluorinated diamines of the present invention have a variety of commercial applications as stain and oil resistant coatings, fouling release coatings, encapsulants for electrical devices, curing agents for epoxies, etc.
摘要翻译：本发明提供氟化二胺和由其形成的聚合物，例如聚脲，聚氨酯脲，聚酰胺，聚酰亚胺等。本发明的氟化二胺是高度亲核的并且被构造成提供具有最佳表面性质的聚合物材料。在本发明的氟化二胺中，端基是从全氟烷基基本上除去的伯氨基。此外，在侧链中存在氟，这允许碳氟化合物链段迁移到聚合物/空气界面，由此提供具有高氟浓度的聚合物表面。因此，由本发明的氟化二胺形成的聚合物具有各种商业用途，如防污涂料，防污涂料，电气装置用密封剂，环氧树脂固化剂等。

6. 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。

7. 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。

8. 发明授权

US5204441A Polyfluorinated, branched-chain diols and diisocyanantes and fluorinated polyurethanes prepared therefrom 失效
标题翻译：由其制备的多氟，支链二醇和二异氰酸酯和氟化聚氨酯
公开(公告)号：US5204441A
公开(公告)日：1993-04-20
申请号：US491972
申请日：1990-03-12
申请人： Kurt Baum , Thomas G. Archibald , Aslam A. Malik
发明人： Kurt Baum , Thomas G. Archibald , Aslam A. Malik
IPC分类号： C07C19/16 , C07C31/42 , C07C211/15 , C07C265/04 , C08G18/38 , C08G18/77
CPC分类号： C07C31/42 , C07C19/16 , C07C211/15 , C07C265/04 , C08G18/3812 , C08G18/773
摘要： Branched-chain diols and a method of forming them by reacting 1,4-diiodoperfluorobutane and perfluoropropylene to obtain branched-chain diiodide adducts thereof, reacting the diiodide adducts with ethylene to obtain I--CH.sub.2 CH.sub.2 --R--CH.sub.2 CH.sub.2 --I, wherein R is a branched-chain perfluoroalkyl radical, and hydrolysing the iodo groups to alcohols to obtain HO--CH.sub.2 CH.sub.2 --R--CH.sub.2 CH.sub.2 --OH. These diols can be reacted with branched-chain diisocyanates to form polyurethanes of better processability and lower glass transition temperatures than polyurethanes prepared from linear fluorinated monomers.
摘要翻译：支链二醇和通过1,4-二碘全氟丁烷和全氟丙烯反应形成它们的方法，得到其支链二碘化物加合物，使二碘化物加合物与乙烯反应，得到I-CH 2 CH 2 -R-CH 2 CH 2 -I，其中R为支链全氟烷基，并将碘基水解成醇，得到HO-CH 2 CH 2 -R-CH 2 CH 2 -OH。这些二醇可以与支链二异氰酸酯反应形成与由线性氟化单体制备的聚氨酯相比具有更好加工性和较低玻璃化转变温度的聚氨酯。

9. 发明授权

US08163933B2 Clean, high-yield preparation of S,S and R,S amino acid isosteres 有权
标题翻译：清洁，高产量制备S，S和R，S氨基酸等离子体
公开(公告)号：US08163933B2
公开(公告)日：2012-04-24
申请号：US11956515
申请日：2007-12-14
申请人： Aslam A. Malik , Todd E. Clement , Hasan Palandoken , James Robinson, III , Joy A. Stringer
发明人： Aslam A. Malik , Todd E. Clement , Hasan Palandoken , James Robinson, III , Joy A. Stringer
IPC分类号： C07D263/00
CPC分类号： C07C271/22 , C07B2200/09 , C07C213/00 , C07D263/20 , C07D303/36 , C07C215/08
摘要： The present invention provides compounds and methods that can be used to convert the intermediate halomethyl ketones (HMKs), e.g., chloromethyl ketones, to the corresponding S,S- and R,S-diastereomers. More particularly, the present invention provides: (1) reduction methods; (2) inversion methods; and (3) methods involving the epoxidation of alkenes. Using the various methods of the present invention, the R,S-epoxide and the intermediary compounds can be prepared reliably, in high yields and in high purity.
摘要翻译：本发明提供可用于将中间卤代甲基酮（HMK）如氯甲基酮转化成相应的S，S-和R，S-非对映异构体的化合物和方法。更具体地说，本发明提供：（1）还原方法; （2）反演方法; 和（3）涉及烯烃环氧化的方法。使用本发明的各种方法，可以高产率和高纯度可靠地制备R，S-环氧化物和中间体化合物。

10. 发明授权

US07807850B2 Preparation of 2R,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2R，3S-N-异丁基-N-（2-羟基-3-氨基-4-苯基丁基）-P-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：US07807850B2
公开(公告)日：2010-10-05
申请号：US12190713
申请日：2008-08-13
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： C07C303/36 , C07C303/40 , C07C303/00 , C07C209/08 , C07C271/20
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 2R,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbuty1)-p-nitrobenzenesulfonylamide hydrochloride, wherein this compound is prepared directly from the chloromethylalcohol. Importantly, the process of the present invention results in higher yields of 2R,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride without sacrificing its purity. The processes of the present invention can be used to prepare not only the 2R,3S-derivative, but also the 2S,3S-, 2S,2R- and the 2R,3R-derivatives.
摘要翻译：本发明提供了制备2R，3S-N-异丁基-N-（2-羟基-3-氨基-4-苯基丁-1-） - 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2R，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，而不损及其纯度。本发明的方法不仅可用于制备2R，3S-衍生物，而且可制备2S，3S-，2S，2R-和2R，3R-衍生物。

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