Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts

    公开(公告)号:US09598531B2

    公开(公告)日:2017-03-21

    申请号:US14843448

    申请日:2015-09-02

    Applicant: MATERIA, INC.

    Abstract: This invention relates to olefin metathesis catalysts and methods for controlling olefin metathesis reactions. More particularly, the present invention relates to methods and compositions for catalyzing and controlling ring opening metathesis polymerization (ROMP) reactions and the manufacture of polymer articles via ROMP. This invention also relates to olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts, wherein the at least two metal carbene olefin metathesis catalysts are structurally different, are chemically different, are distinct compounds, are not isomers, are not structural isomers, are not diastereoisomers, are not stereoisomers, are not enantiomers, or are not cis/trans isomers of each other, or any combinations thereof. This invention also relates to a ROMP composition comprising a resin composition comprising at least one cyclic olefin, and an olefin metathesis catalyst composition comprising at least two metal carbene olefin metathesis catalysts, wherein the at least two metal carbene olefin metathesis catalysts are structurally different, are chemically different, are distinct compounds, are not isomers, are not structural isomers, are not diastereoisomers, are not stereoisomers, are not enantiomers, or are not cis/trans isomers of each other, or any combinations thereof. This invention also relates to a method of making an article comprising combining an olefin metathesis catalyst composition comprising at least two metal carbene olefin metathesis catalysts with a resin composition comprising at least one cyclic olefin, thereby forming a ROMP composition, and subjecting the ROMP composition to conditions effective to polymerize the ROMP composition, wherein the at least two metal carbene olefin metathesis catalysts are structurally different, are chemically different, are distinct compounds, are not isomers, are not structural isomers, are not diastereoisomers, are not stereoisomers, are not enantiomers, or are not cis/trans isomers of each other, or any combinations thereof. Polymer products produced via the metathesis reactions of the invention may be utilized for a wide range of materials and composite applications. The invention has utility in the fields of catalysis, organic synthesis, and polymer and materials chemistry and manufacture.

    Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
    26.
    发明授权
    Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts 有权
    螯合卡宾配体前体及其在复分解催化剂合成中的应用

    公开(公告)号:US09504997B2

    公开(公告)日:2016-11-29

    申请号:US14272859

    申请日:2014-05-08

    Applicant: Materia, Inc.

    Abstract: Chelating ligand precursors for the preparation of olefin methathesis catalysts are disclosed. The resulting catalysts are air stable monomeric species capable of promoting various methathesis reactions efficiently, which can be recovered from the reaction mixture and reused. Internal olefin compounds, specifically beta-substituted styrenes, are used as ligand precursors. Compared to terminal olefin compounds such as unsubstituted styrenes, the beta-substituted styrenes are easier and less costly to prepare, and more stable since they are less prone to spontaneous polymerization. Methods of preparing chelating-carbene methathesis catalysts without the use of CuCl are disclosed. This eliminates the need for CuCl by replacing it with organic acids, mineral acids, mild oxidants or even water, resulting in high yields of Hoveyda-type methathesis catalysts. The invention provides an efficient method for preparing chelating-carbene metathesis catalysts by reacting a suitable ruthenium complex in high concentrations of the ligand precursors followed by crystallization from an organic solvent.

    Abstract translation: 公开了用于制备烯烃复合催化剂的螯合配体前体。 得到的催化剂是能够有效促进各种复合反应的空气稳定的单体物质,其可以从反应混合物中回收并重复使用。 使用内部烯烃化合物,特别是β-取代的苯乙烯作为配体前体。 与末端烯烃化合物如未取代的苯乙烯相比,β-取代的苯乙烯更容易制备成本更低,更稳定,因为它们不易于自发聚合。 公开了不使用CuCl制备螯合 - 卡宾络合催化剂的方法。 这通过用有机酸,无机酸,温和氧化剂甚至水代替它来消除对CuCl的需要,导致Hoveyda型复分解催化剂的高产率。 本发明提供了一种制备螯合碳烯复分解催化剂的有效方法,该方法是通过在高浓度配体前体中合适的钌络合物,然后从有机溶剂中结晶而制备。

    LIQUID MOLDING COMPOSITIONS
    28.
    发明申请
    LIQUID MOLDING COMPOSITIONS 有权
    液体成型组合物

    公开(公告)号:US20160257779A1

    公开(公告)日:2016-09-08

    申请号:US14899165

    申请日:2014-07-03

    Applicant: MATERIA, INC.

    Abstract: The present invention relates to methods and compositions for olefin metathesis. More particularly, the present invention relates to methods and compositions for ring opening metathesis polymerization (ROMP) reactions and the manufacture of polymer articles and/or polymer composite articles via ROMP Polymer products produced via the metathesis reactions of the invention may be utilized in a wide range of materials and composite applications. The invention has utility in the fields of polymer and materials chemistry and manufacture.

    Abstract translation: 本发明涉及烯烃复分解的方法和组合物。 更具体地说,本发明涉及用于开环易位聚合(ROMP)反应的方法和组合物以及通过ROMP制备聚合物制品和/或聚合物复合制品通过本发明的复分解反应生产的聚合物产品可用于宽 材料和复合材料应用范围。 本发明在聚合物和材料化学和制造领域具有实用性。

    PREPARATION OF SURFACTANTS VIA CROSS-METATHESIS
    29.
    发明申请
    PREPARATION OF SURFACTANTS VIA CROSS-METATHESIS 有权
    通过跨METASESES制备表面活性剂

    公开(公告)号:US20160186094A1

    公开(公告)日:2016-06-30

    申请号:US14877632

    申请日:2015-10-07

    Applicant: MATERIA, INC.

    Abstract: The present invention relates to compositions comprising alkene benzenes or alkene benzene sulfonates or alkylbenzenes or alkylbenzene sulfonates; methods for making alkene benzenes or alkene benzene sulfonates or alkylbenzenes or alkylbenzene sulfonates; where the benzene ring is optionally substituted with one or more groups designated R*, where R* is defined herein. More particularly, the present invention relates to compositions comprising 2-phenyl linear alkene benzenes or 2-phenyl linear alkene benzene sulfonates or 2-phenyl linear alkylbenzenes or 2-phenyl linear alkylbenzene sulfonates; methods for making 2-phenyl alkene benzenes or 2-phenyl alkene benzene sulfonates or 2-phenyl alkylbenzenes or 2-phenyl alkylbenzene sulfonates; where the benzene ring is optionally substituted with one or more groups designated R*, where R* is defined herein. This invention also relates to compositions, methods of making, use of, and articles of manufacture comprising 2-ethoxylated hydroxymethylphenyl linear alkyl benzenes. This invention also relates to compositions, methods of making, use of, and articles of manufacture comprising 2-propoxylated hydroxymethylphenyl linear alkyl benzenes.

    Abstract translation: 本发明涉及包含烯烃苯或烯烃苯磺酸盐或烷基苯或烷基苯磺酸盐的组合物; 制备烯烃苯或烯烃苯磺酸盐或烷基苯或烷基苯磺酸盐的方法; 其中苯环任选被一个或多个指定为R *的基团取代,其中R *在本文中定义。 更具体地说,本发明涉及包含2-苯基线性烯烃苯或2-苯基直链烯烃苯磺酸盐或2-苯基直链烷基苯或2-苯基直链烷基苯磺酸盐的组合物; 制备2-苯基烯烃苯酚或2-苯基烯烃苯磺酸盐或2-苯基烷基苯或2-苯基烷基苯磺酸盐的方法; 其中苯环任选被一个或多个指定为R *的基团取代,其中R *在本文中定义。 本发明还涉及包含2-乙氧基化羟甲基苯基直链烷基苯的组合物,制备方法,使用方法和制品。 本发明还涉及包含2-丙氧基化羟甲基苯基直链烷基苯的组合物,制备,使用和制品的方法。

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