Patents Assigned to Materia, Inc.
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Patent number: 8754249Abstract: 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.Type: GrantFiled: July 5, 2012Date of Patent: June 17, 2014Assignee: Materia, Inc.Inventors: Richard L. Pederson, Jason K. Woertink, Christopher M. Haar, David E. Gindelberger, Yann Schrodi
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Publication number: 20140147688Abstract: A vacuum-assisted resin transfer molding (VARTM) method is disclosed, the method comprising: providing a vacuum-assisted resin transfer mold assembly comprising a mold having a first mold surface and a second mold surface arranged to enclose a laminate assembly within a space between the first and second mold surfaces when the laminate assembly is placed on the first mold surface; providing a laminate assembly comprising a laminate pre-form, a peel ply, and a resin distribution media pervious to the flow of a resin, the laminate pre-form having first and second surfaces, the first surface of the pre-form positioned to be in contact with the first mold surface, the peel ply positioned such that the second surface of the laminate pre-form is in contact with the peel ply, and the resin distribution media positioned to be contained within the first and second mold surfaces; positioning at least one resin flow control structure to modify the flow of resin within the resin distribution media; providing at least oneType: ApplicationFiled: August 23, 2011Publication date: May 29, 2014Applicant: MATERIA, INC.Inventors: Sergio Corral, Stephen Crane, Anthony R. Stephen, Christopher J. Cruce, Everado Garcia Flores
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Patent number: 8703965Abstract: Methods for the preparation of saturated imidazolinium salts and related compounds that comprises reaction of formamidines with compounds such as dihaloethane and an optional base are disclosed. Alternatively, the imidazolinium salts and related compounds can be prepared in a one-step process without purification of the formamidine reactant. These methods make it possible to obtain numerous imidazolinium salts and related compounds under solvent-free reaction conditions and in excellent yields.Type: GrantFiled: November 10, 2008Date of Patent: April 22, 2014Assignees: Materia, Inc., California Institute of TechnologyInventors: Kevin Kuhn, Robert H. Grubbs
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Publication number: 20140088260Abstract: The invention discloses an adhesion agent composition comprising at least one C3-C200 olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and at least one compatibilizing functionality for interacting with a substrate surface. The substrate surface can be any surface, for example, silicate glasses, silicate minerals, metals, metal alloys, ceramics, natural stones, plastics, carbon, silicon, and semiconductors. The invention also discloses articles of manufacture utilizing these adhesion agents as well as methods for adhering a polyolefin to a substrate surface.Type: ApplicationFiled: March 15, 2013Publication date: March 27, 2014Applicant: MATERIA, INC.Inventor: MATERIA, INC.
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Patent number: 8597794Abstract: The invention discloses an adhesion agent composition comprising at least one C3-C200 olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and at least one compatibilizing functionality for interacting with a substrate surface. The substrate surface can be any surface, for example, silicate glasses, silicate minerals, metals, metal alloys, ceramics, natural stones, plastics, carbon, silicon, and semiconductors. The invention also discloses articles of manufacture utilizing these adhesion agents as well as methods for adhering a polyolefin to a substrate surface.Type: GrantFiled: June 21, 2011Date of Patent: December 3, 2013Assignee: Materia, Inc.Inventors: Michael A. Giardello, Christopher M. Haar
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Publication number: 20130261312Abstract: Supported olefin metathesis catalysts are disclosed, and more particularly, a supported catalyst complex comprising a catalyst composed of a Group 8 transition metal complex comprising a labile ligand and a non-labile ligand and a support, wherein the metal complex and the support are linked together by one or more linkers, in which one of the linkers connects the labile ligand of the complex to the support and the same or a different linker connects the non-labile ligand of the complex to the support. A method for preparing a supported catalyst complex is further disclosed. The invention further relates to the use of the supported olefin metathesis catalyst in performing metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.Type: ApplicationFiled: June 4, 2012Publication date: October 3, 2013Applicant: MATERIA, INC.Inventors: DARYL ALLEN, MICHAEL GIARDELLO
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Publication number: 20130204026Abstract: Synthetic methods for the in-situ formation of olefin metathesis catalysts are disclosed, as well as the use of such catalysts in metathesis reactions of olefins and olefin compounds.Type: ApplicationFiled: March 24, 2011Publication date: August 8, 2013Applicant: MATERIA, INC.Inventor: Yann Schrodi
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Publication number: 20130172568Abstract: 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.Type: ApplicationFiled: July 5, 2012Publication date: July 4, 2013Applicant: Materia, Inc.Inventors: Richard L. Pederson, Jason K. Woertink, Christopher M. Haar, David E. Gindelberger, Yann Schrodi
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Patent number: 8361922Abstract: The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.Type: GrantFiled: August 30, 2011Date of Patent: January 29, 2013Assignees: Materia, Inc., California Institute of TechnologyInventors: Jacob Berlin, Robert H. Grubbs, Yann Schrodi, Ian C. Stewart
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Patent number: 8324334Abstract: Olefin metathesis polymerization reactions are disclosed, and more particularly ring-opening metathesis polymerization of cyclic olefins with olefinic compounds, such as are derived from seed oils and the like, to form telechelic polymers. In one aspect, a method is provided for carrying out a catalytic ring-opening metathesis polymerization reaction, comprising contacting at least one olefinic compound with at least one cyclic olefin, in the presence of a ruthenium alkylidene olefin metathesis catalyst under conditions effective to allow ring-opening metathesis polymerization of the cyclic olefin, whereby the cyclic olefin polymer formed is terminated with the olefinic compound. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial chemistry.Type: GrantFiled: August 21, 2009Date of Patent: December 4, 2012Assignee: Materia, Inc.Inventors: Simon C. Jones, Farshad J. Motamedi, Li-Sheng Wang, Brian Edgecombe, Michael A. Giardello
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Publication number: 20120123133Abstract: The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.Type: ApplicationFiled: August 30, 2011Publication date: May 17, 2012Applicants: CALIFORNIA INSTITUTE OF TECHNOLOGY, MATERIA, INC.Inventors: Jacob BERLIN, Robert H. GRUBBS, Yann SCHRODI, Ian C. STEWART
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Publication number: 20120058275Abstract: The invention discloses an adhesion agent composition comprising at least one C3-C200 olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and at least one compatibilizing functionality for interacting with a substrate surface. The substrate surface can be any surface, for example, silicate glasses, silicate minerals, metals, metal alloys, ceramics, natural stones, plastics, carbon, silicon, and semiconductors. The invention also discloses articles of manufacture utilizing these adhesion agents as well as methods for adhering a polyolefin to a substrate surface.Type: ApplicationFiled: June 21, 2011Publication date: March 8, 2012Applicant: MATERIA, INC.Inventors: Michael A. Giardello, Christopher M. Haar
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Publication number: 20110294971Abstract: Olefin metathesis polymerization reactions are disclosed, and more particularly ring-opening metathesis polymerization of cyclic olefins with olefinic compounds, such as are derived from seed oils and the like, to form telechelic polymers. In one aspect, a method is provided for carrying out a catalytic ring-opening metathesis polymerization reaction, comprising contacting at least one olefinic compound with at least one cyclic olefin, in the presence of a ruthenium alkylidene olefin metathesis catalyst under conditions effective to allow ring-opening metathesis polymerization of the cyclic olefin, whereby the cyclic olefin polymer formed is terminated with the olefinic compound. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial chemistry.Type: ApplicationFiled: August 21, 2009Publication date: December 1, 2011Applicant: MATERIA, INC.Inventors: Simon C. Jones, Farshad J. Motamedi, Li-Sheng Wang, Brian Edgecombe, Michael A. Giardello
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Patent number: 8008224Abstract: The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.Type: GrantFiled: December 18, 2006Date of Patent: August 30, 2011Assignees: Materia, Inc., California Institute of TechnologyInventors: Jacob Berlin, Robert H. Grubbs, Yann Schrodi, Ian C. Stewart
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Patent number: 7964320Abstract: The invention discloses an adhesion agent composition comprising at least one C3-C200 olefin compound having at least one metathesis active double bond, wherein the olefin is substituted or unsubstituted; and at least one compatibilizing functionality for interacting with a substrate surface. The substrate surface can be any surface, for example, silicate glasses, silicate minerals, metals, metal alloys, ceramics, natural stones, plastics, carbon, silicon, and semiconductors. The invention also discloses articles of manufacture utilizing these adhesion agents as well as methods for adhering a polyolefin to a substrate surface.Type: GrantFiled: March 4, 2008Date of Patent: June 21, 2011Assignee: MATERIA, Inc.Inventors: Michael A. Giardello, Christopher M. Haar
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Publication number: 20110124868Abstract: This invention relates generally to olefin metathesis, more particularly, to tri- or tetra-substituted imidazolinium salts which are precursors to N-heterocyclic carbene (NHC) ligands with tri- or tetra-substituted imidazolinium rings, organometallic ruthenium complexes comprising gem di-substituted imidazolinium NHC ligands, organometallic ruthenium complexes comprising tri- or tetra-substituted imidazolinium NHC ligands, and to olefin metathesis methods using them. The catalysts and methods of the invention have utility in the fields of catalysis, organic synthesis, and industrial chemistry.Type: ApplicationFiled: April 9, 2009Publication date: May 26, 2011Applicants: MATERIA, INC., CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: Robert H. Grubbs, Cheol Keun Chung, Jean-Baptiste Bourg, Kevin Kuhn
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Publication number: 20110112319Abstract: 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.Type: ApplicationFiled: October 26, 2010Publication date: May 12, 2011Applicant: MATERIA, INC.Inventors: Richard L. PEDERSON, Jason K. WOERTINK, Christopher M. HAAR, David E. GINDELBERGER, Yann SCHRODI
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Publication number: 20110087032Abstract: Methods for the preparation of saturated imidazolinium salts and related compounds that comprises reaction of formamidines with compounds such as dihaloethane and an optional base are disclosed. Alternatively, the imidazolinium salts and related compounds can be prepared in a one-step process without purification of the formamidine reactant. These methods make it possible to obtain numerous imidazolinium salts and related compounds under solvent-free reaction conditions and in excellent yields.Type: ApplicationFiled: November 10, 2008Publication date: April 14, 2011Applicants: MATERIA, INC., CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: Kevin Kuhn, Robert H. Grubbs
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Patent number: 7820843Abstract: 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.Type: GrantFiled: December 11, 2008Date of Patent: October 26, 2010Assignee: Materia, Inc.Inventors: Richard L. Pederson, Jason K. Woertink, Christopher M. Haar, David E. Gindelberger, Yann Schrodi
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Publication number: 20090088581Abstract: 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.Type: ApplicationFiled: December 11, 2008Publication date: April 2, 2009Applicant: MATERIA, INC.Inventors: Richard L. PEDERSON, Jason K. WOERTINK, Christopher M. HAAR, David E. GINDELBERGER, Yann SCHRODI