Romp polymers having improved resistance to hydrocarbon fluids

    公开(公告)号:US10344118B2

    公开(公告)日:2019-07-09

    申请号:US15547930

    申请日:2016-02-11

    Applicant: MATERIA, INC.

    Abstract: The present invention relates to compositions comprising at least one cyclic olefin, at least one metal carbene olefin metathesis catalyst, and dicumyl peroxide. The present invention relates to a method of making ROMP polymers and articles of manufacture with improved resistance to hydrocarbon fluids. Particularly the invention relates to ROMP polymer compositions with improved resistance to hydrocarbon fluids. Such ROMP polymers and ROMP polymer compositions can be used in a variety of materials and composite applications.

    ADHESION PROMOTERS AND GEL-MODIFIERS FOR OLEFIN METATHESIS COMPOSITIONS

    公开(公告)号:US20220089481A1

    公开(公告)日:2022-03-24

    申请号:US17365433

    申请日:2021-07-01

    Applicant: MATERIA, INC.

    Abstract: This invention relates to compositions and methods for improving the adhesion of resin compositions to substrate materials, pre-treating substrate materials to improve the adhesion of resin compositions to the substrate materials, and/or controlling gel formation of resin compositions. More particularly, the invention relates to compositions and methods for improving the adhesion of ring opening metathesis polymerization (ROMP) compositions to substrate materials using adhesion promoters containing isocyanate groups in a resin composition. The invention also relates to methods for improving the adhesion of resin compositions to substrate materials by pre-treating substrate materials with adhesion promoters containing isocyanate groups. The invention further relates to a method of providing a gel-modified ROMP composition, in which a hydroperoxide is added to a ROMP polymerizable resin composition in order to control gel formation of the polymerizing resin. An improved ROMP composition is further disclosed, comprising a cyclic olefin, a ROMP metathesis catalyst, an adhesion promoter, and an added hydroperoxide gel modifier. The polymer products produced via ROMP 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.

    Adhesion promoter compositions for cyclic olefin resin compositions

    公开(公告)号:US10907018B2

    公开(公告)日:2021-02-02

    申请号:US15120554

    申请日:2015-02-25

    Applicant: MATERIA, INC.

    Abstract: This invention relates to compositions and methods for improving the adhesion of resin compositions to substrate materials. More particularly, the invention relates to compositions and methods for improving the adhesion of ROMP compositions to substrate materials using an adhesion promoter composition, where the adhesion promoter composition comprises a pre-reacted mixture comprising at least one compound containing at least two isocyanate groups and at least one compound comprising a heteroatom-containing functional group and a metathesis active olefin, where the adhesion promoter composition is storage stable and/or possesses in-resin storage stability when added to a resin composition, particularly a cyclic olefin resin composition, such as a ROMP composition. The polymer products produced via ROMP reactions of the invention may be utilized for a wide range of materials and composite applications. The invention has utility in the fields of polymer and materials chemistry and manufacture.

    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.

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