Patents Assigned to Michigan Molecular Institute
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Patent number: 6995215Abstract: Hyperbranched polymers having a plurality of at least two different types of functional groups are described. Specific embodiments include hyperbranched polymers having functional groups of a first type that are substantially uniformly distributed throughout the hyperbranched polymer molecule and a second type of functional group that is substantially uniformly distributed at the terminals of the hyperbranched polymer molecule. The hyperbranched polymers having different types of functional groups are synthesized by reacting one or more monomers having functional groups that are capable of reacting during a set of polymerization conditions to form a hyperbranched polymer, wherein at least one of the monomers contains latent functional groups that are not reactive during polymerization.Type: GrantFiled: June 2, 2003Date of Patent: February 7, 2006Assignee: Michigan Molecular InstituteInventors: Petar R. Dvornic, Jin Hu, Dale J. Meier, Robert M. Nowak
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Patent number: 6866764Abstract: An inexpensive process for depositing an electrically conductive material on selected surfaces of a dielectric substrate may be advantageously employed in the manufacture of printed wiring boards having high quality, high density, fine-line circuitry, thereby allowing miniaturization of electronic components and/or increased interconnect capacity. The process may also be used for providing conductive pathways between opposite sides of a dielectric substrate and in decorative metallization applications.Type: GrantFiled: February 21, 2002Date of Patent: March 15, 2005Assignee: Michigan Molecular InstituteInventors: David A. Dalman, Petar R. Dvornic
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Patent number: 6812298Abstract: Hyperbranched polymers are prepared by a process in which a monomer having the form Ax is reacted with another monomer of the form By, where A and B are functional groups that do not react with themselves, but do react with each other. The process allows synthesis of hyperbranched polymers having a single type of terminal functional group from comonomers, each of which has a single type of functional group. The invention allows greater flexibility in the preparation of a larger variety of different hyperbranched polymers and enables hyperbranched polymers to be prepared at a lower cost as compared with conventional processes using monomers having two types of functional groups that react during polymerization.Type: GrantFiled: October 29, 2002Date of Patent: November 2, 2004Assignee: Michigan Molecular InstituteInventors: Petar R. Dvornic, Jin Hu, Dale J. Meier, Robert M. Nowak, Paul L. Parham
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Patent number: 6646089Abstract: Hyperbranched polymers having a plurality of at least two different types of functional groups are described. Specific embodiments include hyperbranched polymers having functional groups of a first type that are substantially uniformly distributed throughout the hyperbranched polymer molecule and a second type of functional group that is substantially uniformly distributed at the terminals of the hyperbranched polymer molecule. The hyperbranched polymers having different types of functional groups are synthesized by reacting one or more monomers having functional groups that are capable of reacting during a set of polymerization conditions to form a hyperbranched polymer, wherein at least one of the monomers contains latent functional groups that are not reactive during polymerization.Type: GrantFiled: October 3, 2001Date of Patent: November 11, 2003Assignee: Michigan Molecular InstituteInventors: Petar R. Dvornic, Jin Hu, Dale J. Meier, Robert M. Nowak
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Patent number: 6534600Abstract: Hyperbranched polymers are prepared by a process in which a monomer having the form Ax is reacted with another monomer of the form By, where A and B are functional groups that do not react with themselves, but do react with each other. The process allows synthesis of hyperbranched polymers having a single type of terminal functional group from comonomers, each of which has a single type of functional group. The invention allows greater flexibility in the preparation of a larger variety of different hyperbranched polymers and enables hyperbranched polymers to be prepared at a lower cost as compared with conventional processes using monomers having two types of functional groups that react during polymerization.Type: GrantFiled: March 26, 2001Date of Patent: March 18, 2003Assignee: Michigan Molecular InstituteInventors: Petar R. Dvornic, Jin Hu, Dale J. Meier, Robert M. Nowak, Paul L. Parham
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Patent number: 6384172Abstract: Hyperbranched polycarbosilanes, polycarbosiloxanes, polycarbosilazenes and copolymers thereof are prepared by reacting a difunctional or polyfunctional monomer having functional groups of one type (A) without any other functional groups capable of reacting significantly during polymerization, and a difunctional or polyfunctional monomer having functional groups of another type (B) without any other functional groups capable of reacting significantly during polymerization, wherein each A-functional group is reacted with a B-functional group, and wherein at least one of the monomers has a functionality of at least three. The process enables hyperbranched polycarbosilanes, polycarbosiloxanes, polycarbosilazenes and copolymers thereof to be prepared at a lower cost than with conventional synthesis processes, and provides greater flexibility in the preparation of a larger variety of different types of hyperbranched polycarbosilanes, polycarbosiloxanes, polycarbosilazenes and copolymers thereof.Type: GrantFiled: January 2, 2001Date of Patent: May 7, 2002Assignee: Michigan Molecular InstituteInventors: Petar R. Dvornic, Jin Hu, Dale J. Meier, Robert M. Nowak
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Patent number: 6177510Abstract: An aqueous dispersion comprising a copolymer which is the polymerization product of a mixture of vinylic monomers wherein from about 5% to about 90% by weight of the vinylic monomers are selected from co-esters of a drying oil acid and an unsaturated &agr;, &bgr;-polymerizable unsaturated carboxylic acid, contains from about 0.5% to about 50% by weight based on the weight of the copolymer of a hydrophobic ester or partial ester of a drying oil acid and a polyol. The copolymer polymerized in the presence of the hydrophobic ester or partial ester is characterized by a relatively low gel content, and by a relatively broad, multi-nodal, molecular weight distribution, including a low molecular weight component which acts as a transient plasticizer and coalescing agent. The aqueous dispersions can be formulated into quick drying coating compositions which form smooth protective films on various substrates, without requiring volatile coalescing agents.Type: GrantFiled: April 12, 1999Date of Patent: January 23, 2001Assignee: Michigan Molecular InstituteInventor: John C. Saam
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Patent number: 5902863Abstract: Dendrimer-based networks are prepared from copolydendrimer precursors having well defined hydrophilic polyamidoamine (PAMAM) or polypropyleneimine (PPI) interiors, and organosilicon outer layers ending with .tbd.Si--OCH.sub.3 surface groups. These networks have precisely controllable size, shape, and spatial distribution, of nanoscopic hydrophilic and hydrophobic domains. Such constructs are prepared by crosslinking one type of copolydendrimer precursor, or by crosslinking mixtures of different copolydendrimers having different generations of PAMAM or PPI dendrimers in the interior, surrounded by different organosilicon exteriors. Crosslinking can be controlled by adding difunctional, trifunctional, or polyfunctional low molecular weight or oligomeric crosslinking agents; or by exposing a copolydendrimer having hydrolyzable surface groups to atmospheric moisture. Elastomeric dendrimer-based networks have low glass temperatures of -15.degree. C.Type: GrantFiled: July 21, 1997Date of Patent: May 11, 1999Assignees: Dow Corning Corporation, Michigan Molecular InstituteInventors: Petar R. Dvornic, Agnes M. deLeuze-Jallouli, Michael James Owen, Susan Victoria Perz
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Patent number: 5750751Abstract: Glycol co-esters of drying-oil fatty acids and polymerizable unsaturated carboxylic acids are formed by a novel bi-phase catalysis in liquid-liquid or liquid-solid dispersions. The co-esters form directly from drying-oil acids and partial glycol esters of vinylic carboxylic acids, or vice versa. Complete removal of the by-produced water by distillation is unnecessary and the commonly encountered side reactions of direct esterification are suppressed since reaction temperatures can be as low as ambient. The expensive acid chlorides or anhydrides combined with acid acceptors, previously used to prepare such co-esters, are circumvented along with the by-produced hydrochlorides or carboxylates which must be recovered and disposed in an environmentally acceptable way. The co-esters formed here are useful in free radical copolymerizations that provide novel film-forming polymers capable of cross-linig when dried in air. They can be formed in bulk, solution or as latexes.Type: GrantFiled: November 1, 1996Date of Patent: May 12, 1998Assignee: Michigan Molecular InstituteInventor: John C. Saam
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Patent number: 5739218Abstract: Radially layered copoly-dendrimers having unusual surface properties and novel applications have been synthesized and characterized. These are the first copolymeric dendrimers composed of a hydrophilic poly(amidoamine) (PAMAM) interior with hydrophobic organosilicon surfaces. These dendrimers have been prepared by surface modifications of an ethylene diamine core PAMAM dendrimer with (3-acryloxypropyl)methyldimethoxysilane, (3-acryloxypropyl)bis(vinyldimethylsiloxy)methylsilane, (3-acryloxypropyl)tris(trimethylsiloxy)silane, chloromethyltrimethylsilane, and chloromethyldimethylvinylsilane, to varying degrees of surface coverage. The obtained products were characterized by .sup.1 H, .sup.13 C, and .sup.29 Si NMR, and by DSC and TGA. The dendrimers with less completely covered organosilicon surfaces are water soluble, and have considerable surface activity, the best of which lowered the surface tension of water to less than 30 mN/m.Type: GrantFiled: June 2, 1997Date of Patent: April 14, 1998Assignees: Dow Corning Corporation, Michigan Molecular InstituteInventors: Petar R. Dvornic, Agnes M. deLeuze-Jallouli, Douglas Swanson, Michael James Owen, Susan Victoria Perz
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Patent number: 5705573Abstract: A novel process for preparing poly(2-isopropenyl-2-oxazoline or oxazine) and its methyl methacrylate copolymer, which are useful as water borne curing agents, particularly in the non-stick coating industry. The process converts commercially available poly(methyl methacrylate) into poly(2-isopropenyl-2-oxazoline or oxazine) polymers or copolymers with methyl methacrylate, while circumventing the use of the highly toxic monomer, 2-isopropenyl-2-oxazoline or oxazine. The process involves converting a poly(methacrylic ester) to the corresponding poly(.beta.-hydroxy-N-ethyl or propyl methacrylamide) and activating the ring-forming .beta.-hydroxy-N-ethyl or propyl methacrylamide moiety to form an oxazoline or oxazine ring.Type: GrantFiled: September 5, 1996Date of Patent: January 6, 1998Assignee: Michigan Molecular InstituteInventors: Douglas R. Swanson, Donald A. Tomalia
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Patent number: 4374957Abstract: A tacky thermoplastic elastomeric linear triblock polymer corresponding to the formula A-B-A is made from a monovinyl aromatic hydrocarbon and myrcene. A is a polymer block of a monovinyl aromatic hydrocarbon, e.g. styrene, having an average molecular weight between 2,000 and 100,000 and a glass transition temperature above 25.degree. C. B is a polymeric block of myrcene (7-methyl-3-methylene-1,6-octadiene, C.sub.10 H.sub.16) having an average molecular weight between 10,000 and 1,000,000 and a glass transition temperature below -40.degree. C. B constitutes from 40 to 80 percent of the total. The products are made by sequential polymerization with an organolithium initiator.Type: GrantFiled: October 29, 1981Date of Patent: February 22, 1983Assignee: Michigan Molecular InstituteInventor: Roderic P. Quirk
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Patent number: 4354018Abstract: A resinous linear polyester, poly(oxy-1,4-phenylene-3-oxotrimethylene), is made by the self-condensation of 3-(parahydroxyphenyl)propionic acid. The process is carried out interfacially or in an inert solvent by mixing 3-(parahydroxyphenyl)propionic acid with at least an equimolar proportion of thionyl chloride and maintaining the mixture at a reaction temperature for a time sufficient to allow substantially complete autocondensation. A base may be added in proportion at least about equivalent to the thionyl chloride. The autocondensate when purified is a white solid linear polyester not melting up to 360.degree. C. and may exhibit an intrinsic viscosity of at least 75 ml/g. It may be molded or pressed into a film.Co-condensed polyesters of 3-(parahydroxyphenyl)propionic acid with up to an equimolar proportion of parahydroxyphenylacetic acid may similarly be prepared.Type: GrantFiled: February 1, 1982Date of Patent: October 12, 1982Assignee: Michigan Molecular InstituteInventors: Hans-G. Elias, Robert J. Warner
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Patent number: 4348350Abstract: A solid crystalline organic polymer is made into a filament, rod, or film by ultra-drawing it at a temperature within 70.degree. C. of but below its melting point at the operating pressure while subjecting the polymer during and immediately after drawing to a hydrostatic pressure of at least about 500 atmospheres applied by a fluid medium inert to the polymer. High-density polyethylene and isotactic propylene are preferred polymers. A draw ratio of at least 20:1, and as high as 60:1, may be used. Pressure may be up to 2500 atmospheres or more. The rate of drawing for polyethylene is above 500 percent per minute. The ultra-drawn products are transparent, essentially free of internal voids, and exhibit very high tensile moduli of elasticity, up to 65 to 70 Giga-Pascals in the case of polyethylene.Type: GrantFiled: September 26, 1980Date of Patent: September 7, 1982Assignee: Michigan Molecular InstituteInventors: Dale J. Meier, Leszek Jarecki