Boron Bonded To Hydrogen Or Carbon Atom Compound Patents (Class 526/196)
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Patent number: 6949603Abstract: In one embodiment the invention is a polymerizable composition comprising a) an organoborane amine complex; b) one or more of monomers, oligomers or polymers having olefinic unsaturation which is capable of polymerization by free radical polymerization; c) one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization; and d) a catalyst for the polymerization of the one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization. This composition may further comprise a compound which causes the organoborane amine complex to disassociate.Type: GrantFiled: June 1, 2004Date of Patent: September 27, 2005Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel R. Harrington
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Patent number: 6936672Abstract: A catalyst system and a process for the bulk addition polymerization or of polycyclic olefins, such as norbornene, methylnorbornene, ethylnorbornene, butylnorbornene or hexylnorbornene, 1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonapthalene, 5,5?-(1,2-ethanediyl)bisbicyclo[2.2.1]hept-2-ene, and 1,4,4a,4b,5,8,8a,8b-octahydro-1,4:5,8-dimethanobiphenylene are disclosed. The catalyst includes an organonickel or organopalladium transition metal procatalyst and an activator compound. Polymerization can be carried out in a reaction injection molding process to yield thermoplastic and thermoset molded polymeric articles possessing high glass transition temperatures.Type: GrantFiled: August 2, 2001Date of Patent: August 30, 2005Assignee: Sumitomo Bakelite Co., Ltd.Inventors: Andrew Bell, Larry F. Rhodes, Brian L. Goodall, John C. Fondran, Lester H. Mclntosh, III, Dennis A. Barnes
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Patent number: 6911509Abstract: Functional fluoro-monomers are polymerized with an organoborane initiator to yield functional fluoro-polymers and copolymers including functional polymers prepared from monomers having allylic protons, Si—H groups, and olefinic groups.Type: GrantFiled: February 17, 2004Date of Patent: June 28, 2005Assignees: The Penn State Research Foundation, Daikin Institute of Advanced Chemistry and Technology, Inc.Inventors: Tze-Chiang Chung, Han Hong, Masahiko Oka, Katsuyoshi Kubo
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Patent number: 6867271Abstract: This invention relates to (meth)acrylate based polymerizable compositions and multipart adhesive systems prepared therefrom, which include an aziridine-containing compound in a carrier material with which the aziridine-containing compound is unreactive. The inventive composition demonstrates a flash point above 140° F., desirably above 200° F., for each of the parts of the adhesive system. To achieve the physical properties of the inventive compositions and adhesive systems, it is desirable for the carrier material to have such flash points; however, provided that in their entirety the inventive compositions and adhesive systems have such flash points, it is not necessary for the carrier material itself to have such flash points. The inventive compositions and adhesive systems also include a package for controlling the rate of cure and indicating the extent of cure.Type: GrantFiled: May 14, 2003Date of Patent: March 15, 2005Assignees: Henkel Corporation, Loctite (R&D) LimitedInventors: Eerik Maandi, Brendan J. Kneafsey
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Patent number: 6844080Abstract: Metal alkyl borohydrides are used as initiators of polymerisation, particularly in adhesive compositions for bonding a wide range of substrates including low surface energy substrates such as polyolefins. As described, the metal alkyl borohydrides are of the formula I or II. wherein R1 is C1-C10 alkyl, R2 and R3, which may be the same or different, are H, D, C1-C10 alkyl or C3-C10 cycloalkyl, phenyl, or phenyl-substituted C1-C10 alkyl or C3-C10 cycloalkyl, provided that any two of R1-R3 may optionally be part of a carbocyclic ring, and M+ is a metal ion. In particular, alkali metal trialkyl borohydrides are used, the alkali metal salt being selected from: Lithium triethylborohydride, Sodium triethylborohydride, Potassium triethylborohydride, Lithium tri-sec-butylborohydride, Sodium tri-sec-butylborohydride, Potassium tri-sec-butylborohydride, and Lithium triethylborodeuteride. Other exemplified compounds which are less effective on low surface energy substrates include Lithium 9-borabicyclo [3.3.Type: GrantFiled: October 23, 2001Date of Patent: January 18, 2005Assignee: Loctite (R&D) LimitedInventors: Brendan J. Kneafsey, Gerry Coughlan
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Publication number: 20040242812Abstract: In one embodiment the invention is a polymerizable composition comprising a) an organoborane amine complex; b) one or more of monomers, oligomers or polymers having olefinic unsaturation which is capable of polymerization by free radical polymerization; c) one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization; and d) a catalyst for the polymerization of the one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization. This composition may further comprise a compound which causes the organoborane amine complex to disassociate.Type: ApplicationFiled: June 9, 2004Publication date: December 2, 2004Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel R. Harrington
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Patent number: 6825298Abstract: In one embodiment the invention is a polymerizable composition comprising a) an organoborane amine complex; b) one or more of monomers, oligomers or polymers having olefinic unsaturation which is capable of polymerization by free radical polymerization; c) one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization; and d) a catalyst for the polymerization of the one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization. This composition may further comprise a compound which causes the organoborane amine complex to disassociate.Type: GrantFiled: June 1, 2004Date of Patent: November 30, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel R. Harrington
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Patent number: 6815470Abstract: A dental catalyst for chemical polymerization comprising an acidic compound, an organic peroxide such as cumene hydroperoxide, and aryl borate compound such as sodium tetraphenylborate, but without substantially containing amine compound. This catalyst is chemically highly stable, is easy to handle, is highly active, is less likely to be impaired by polymerization, and does not cause the cured product to be tinted or discolored, and is very useful for the dental restorative.Type: GrantFiled: July 2, 2003Date of Patent: November 9, 2004Assignee: Tokuyama CorporationInventors: Kazuya Ibaragi, Hideki Kazama, Makoto Oguri
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Publication number: 20040220363Abstract: In one embodiment the invention is a polymerizable composition comprising a) an organoborane amine complex; b) one or more of monomers, oligomers or polymers having olefinic unsaturation which is capable of polymerization by free radical polymerization; c) one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization; and d) a catalyst for the polymerization of the one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization. This composition may further comprise a compound which causes the organoborane amine complex to disassociate.Type: ApplicationFiled: June 1, 2004Publication date: November 4, 2004Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel R. Harrington
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Patent number: 6812308Abstract: Initiator systems of the present invention include both a complexed initiator and a carboxylic acid decomplexer. For example, dicarboxylic acid decomplexer, carboxylic acid ester decomplexers, and monocarboxylic acid decomplexers (preferably those comprising an alkyl group having at least nine carbon atoms for low odor compositions) are useful in the present invention.Type: GrantFiled: January 21, 2003Date of Patent: November 2, 2004Assignee: 3M Innovative Properties CompanyInventors: Edward J. Deviny, Dean M. Moren
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Publication number: 20040210015Abstract: In one embodiment the invention is a polymerizable composition comprising a) an organoborane amine complex; b) one or more of monomers, oligomers or polymers having olefinic unsaturation which is capable of polymerization by free radical polymerization; c) one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization; and d) a catalyst for the polymerization of the one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization. This composition may further comprise a compound which causes the organoborane amine complex to disassociate.Type: ApplicationFiled: June 1, 2004Publication date: October 21, 2004Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel R. Harrington
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Patent number: 6806330Abstract: The invention is an amine-organoborane complex wherein the organoborane is a trialkyl borane and the amine is an amine having an amidine structural component; an aliphatic heterocycle having at least one nitrogen in the heterocyclic ring wherein the heterocyclic compound may also contain one or more nitrogen atoms, oxygen atoms, sulfur atoms, or double bonds in the heterocycle; a primary amine which in addition has one or more hydrogen bond accepting groups wherein there is at least two carbon atoms, preferably three, between the primary amine and the hydrogen bond accepting group, such that due to inter- or intramolecular interactions within the complex the strength of the B—N bond is increased; or a conjugated imine. Preferred hydrogen bond accepting groups include the following: a secondary amine, a tertiary amine, an ether, a halogen, a polyether group or a polyamine group.Type: GrantFiled: December 17, 1999Date of Patent: October 19, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Publication number: 20040198935Abstract: The invention is a two part composition useful for initiating cure of one or more polymerizable monomers which cure when exposed to free radicals comprising in one part an organoboraneamine complex and in a second part an isocyanate which is capable of decomplexing the organoborane complex wherein the ratio of amine nitrogen atoms to boron atoms is greater than 4.0:1.0.Type: ApplicationFiled: April 19, 2004Publication date: October 7, 2004Inventors: Steven F. Webb, Mark F. Sonnenschein
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Patent number: 6777512Abstract: In one embodiment the invention is a polymerizable composition comprising a) an organoborane amine complex; b) one or more of monomers, oligomers or polymers having olefinic unsaturation which is capable of polymerization by free radical polymerization; c) one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization; and d) a catalyst for the polymerization of the one or more compounds, oligomers or prepolymers having a siloxane backbone and reactive moieties capable of polymerization. This composition may further comprise a compound which causes the organoborane amine complex to disassociate.Type: GrantFiled: February 28, 2003Date of Patent: August 17, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel R. Harrington
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Patent number: 6762256Abstract: Initiator systems of the invention comprise a complexed initiator comprising a complex of an amidine complexing agent and an initiator; and a decomplexer. The initiator systems are useful for initiating polymerization of at least one monomer to form polymerized compositions. Kits of the invention useful for forming the polymerized compositions comprise a polymerizable composition and an initiator component, wherein the initiator component comprises a complexed amidine initiator. Bonding compositions can be prepared by mixing the polymerizable composition of the kit with the respective initiator component.Type: GrantFiled: May 3, 2002Date of Patent: July 13, 2004Assignee: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Patent number: 6762260Abstract: The invention is a two part polymerizable composition comprising in one part an organoborane amine complex and one or more compounds containing ring opening heterocyclic moieties, and in a second part, compounds capable of being polymerized by free radical polymerization, a catalyst capable of polymerizing compounds containing ring opening heterocyclic moieties and optionally a component that will decomplex the organoborane amine complex. In one embodiment the invention is a two phase system comprising a first phase containing one or more polymers prepared from the compounds which polymerize by free radical polymerization and a second phase comprising polymerized or partially polymerized compounds derived from one or more compounds containing ring opening heterocyclic moieties.Type: GrantFiled: March 5, 2002Date of Patent: July 13, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel D. Harrington
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Patent number: 6740716Abstract: The invention is a two part composition useful for initiating cure of one or more polymerizable monomers which cure when exposed to free radicals comprising in one part an organoboraneamine complex and in a second part an isocyanate which is capable of decomplexing the organoborane complex wherein the ratio of amine nitrogen atoms to boron atoms is greater than 4.0:1.0.Type: GrantFiled: October 30, 2001Date of Patent: May 25, 2004Assignee: Dow Global Technologies Inc.Inventors: Steven P. Webb, Mark F. Sonnenschein
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Patent number: 6740717Abstract: Initiator systems of the invention comprise a complexed initiator comprising a complex of an amidine complexing agent and an initiator; and a decomplexer. The initiator systems are useful for initiating polymerization of at least one monomer to form polymerized compositions. Kits of the invention useful for forming the polymerized compositions comprise a polymerizable composition and an initiator component, wherein the initiator component comprises a complexed amidine initiator. Bonding compositions can be prepared by mixing the polymerizable composition of the kit with the respective initiator component.Type: GrantFiled: February 14, 2003Date of Patent: May 25, 2004Assignee: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Publication number: 20040097673Abstract: Metal alkyl borohydrides are used as initiators of polymerisation, particularly in adhesive compositions for bonding a wide range of substrates including low surface energy substrates such as polyolefins. As described, the metal alkyl borohydrides are of the formula I or II.Type: ApplicationFiled: April 14, 2003Publication date: May 20, 2004Inventors: Brendan J. Kneafsey, Gerry Coughlan
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Patent number: 6734268Abstract: The invention provides bonding compositions and reactive two-part bonding compositions that are useful, for example, in bonding low surface energy substrates (e.g., polyethylene, polypropylene and polytetrafluoroethylene). Bonding compositions of the invention include an organoborane, a polymerizable monomer, and a metal salt which modifies the cure kinetics of the bonding composition to provide a favorable balance of long bonding composition worklife and fast rate of strength build.Type: GrantFiled: December 31, 2001Date of Patent: May 11, 2004Assignee: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Patent number: 6730759Abstract: The invention is polymerizable composition comprising a) an organoborane/amine complex wherein the organoborane is a trialkyl borane or an alkyl cycloalkyl borane and the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; and, b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and optionally c) an effective amount of a compound which causes the complex to disassociate wherein the compound which causes disassociation of the complex is kept separate from the complex until initiation of polymerizatType: GrantFiled: June 15, 2001Date of Patent: May 4, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6713579Abstract: A method of modifying the surface of a low surface energy polymer by contacting the surface with a composition comprising a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and optionally, c) an effective amount of a compound which causes the complex to disassociate.Type: GrantFiled: June 15, 2001Date of Patent: March 30, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6713578Abstract: A method of bonding two or more substrates together which comprises I. contacting the components of the composition comprising a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and, c) optionally an effective amount of a compound which causes the complex to disassociate or heating the composition to a temperature at which the complex dissassociates; II.Type: GrantFiled: June 15, 2001Date of Patent: March 30, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6710145Abstract: A method of coating a substrate which comprises coating a substrate with the composition comprising a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group, and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation, and c) an effective amount of a compound which causes the complex to disassociate; together under conditions such that polymerization is initiated.Type: GrantFiled: June 15, 2001Date of Patent: March 23, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6706831Abstract: The invention is a method of polymerization comprising contacting the components of the polymerizable composition of a) an organoborane/amine complex wherein the amine is selected from the group of amines having an amidine structural component; aliphatic heterocycles having at least one nitrogen in the heterocyclic ring; an alicyclic compound having bound to the ring a substituent having an amine moiety; primary amines which in addition to a primary amine have one or more hydrogen bond accepting groups of an ether, polyether, thioether or halogen wherein there is an alkylene chain of at least two carbon atoms between the primary amine and the hydrogen bond accepting group; and conjugated imines; b) one or more of monomers, oligomers or polymers having olefinic unsaturation; and c) in the presence of an effective amount of a compound which causes the complex to disassociate or at a temperature at which causes the complex to disassociate.Type: GrantFiled: June 15, 2001Date of Patent: March 16, 2004Assignee: Dow Global Technologies Inc.Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
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Patent number: 6699949Abstract: An in situ controlled oxidation reaction of trialkylborane (BR3) in the presence of polyolefin and maleic anhydride produces mono-oxidized trialkylborane adducts, i.e., peroxyldialkylborane (R—O—O—BR2), that can undergo homolytic cleavage to form (R—O* *O—BR2) and activate the polyolefin chain by alkoxyl radical (R—O*) hydrogen-abstraction at ambient temperature. The formed polymeric radical (C*), associated with the oxidized borane moiety (*O—BR2), then reacts with maleic anhydride by addition reaction, without side reactions, to form functional polyolefins that contain incorporated maleic anhydride side groups.Type: GrantFiled: May 30, 2002Date of Patent: March 2, 2004Assignee: Penn State Research FoundationInventor: Tze-Chiang Chung
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Patent number: 6689852Abstract: The present invention is for a transition metal-free catalyst system for synthesizing high molecular weight, linear polymers. The system comprises a catalyst composition having: (a) a neutral compound having the formula AlR3, wherein R is an alkyl or hydride group; (b) a Lewis acid or Lewis acid derivative cocatalyst different from the neutral compound, wherein the cocatalyst reacts with the neutral compound to form an initiator; and (c) an activity-enhancing modifier, wherein the modifier reacts with the initiator to form the catalyst composition. The instant invention is also directed to a method for polymerizing at least one olefinic monomer comprising the step of contacting a feed containing the olefinic monomer under polymerization conditions with the transition metal-free catalyst composition.Type: GrantFiled: January 15, 2002Date of Patent: February 10, 2004Assignee: ExxonMobil Research and Engineering CompanyInventors: Lisa Saunders Baugh, Joseph Anthony Sissano
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Patent number: 6645903Abstract: The present invention provides catalyst components comprising a compound having a weakly coordinating anion salt and a reactive cation, in particular a compound of the formula MxQy. Preferably, each M is independently a cation with at least one M being a reactive cation as defined herein. Q is a fluorinated polyhedral borate moiety. And x and y are absolute values of the oxidation states of Q and M, respectively. The present invention also provides processes for using the catalyst components defined herein.Type: GrantFiled: July 25, 2002Date of Patent: November 11, 2003Assignee: Colorado State University Research FoundationInventors: Steven H. Strauss, Sergei V. Ivanov
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Patent number: 6646076Abstract: Disclosed are internally blocked borates useful for polymerizable compositions, and polymerizable adhesives made therewith. The internally blocked borates have general structures: wherein X represents —CHR6—, oxygen or sulfur; n is an integer; R1, R2, R3, R4, R5, and R6 are independently selected, for example, from unsubstituted and substituted C1-C10 alkyl, alkylene groups, or aryl groups, including other embodiments further defined, and M is a counter ion with positive charge m.Type: GrantFiled: March 25, 2003Date of Patent: November 11, 2003Assignee: Lord CorporationInventors: Jonathan L. Kendall, Robin F. Righettini, Kirk J. Abbey
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Publication number: 20030199651Abstract: Disclosed are internally blocked borates useful for polymerizable compositions, and polymerizable adhesives made therewith.Type: ApplicationFiled: March 25, 2003Publication date: October 23, 2003Inventors: Jonathan L. Kendall, Robin F. Righettini, Kirk J. Abbey
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Patent number: 6632908Abstract: The present invention is directed to (meth)acrylate compositions useful for bonding substrates including metals, plastics, and glass to similar or different substrates, in particular, low energy surfaces. The invention also provides an initiator system for (meth)acrylate based adhesives; a kit for bonding substrates, at least one of which includes a low energy surface; a resultant bonded assembly; and a method of bonding low energy substrates. A (meth)acrylate composition within the present invention includes a (meth)acrylate component and an initiator system including an organometallic compound, a peroxy compound, an aziridine functionalized compound, and a compound having an acid functional group.Type: GrantFiled: March 12, 2002Date of Patent: October 14, 2003Assignee: Henkel Loctite CorporationInventor: Eerik Maandi
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Publication number: 20030176607Abstract: Initiator systems of the invention comprise a complexed initiator comprising a complex of an amidine complexing agent and an initiator; and a decomplexer. The initiator systems are useful for initiating polymerization of at least one monomer to form polymerized compositions. Kits of the invention useful for forming the polymerized compositions comprise a polymerizable composition and an initiator component, wherein the initiator component comprises a complexed amidine initiator. Bonding compositions can be prepared by mixing the polymerizable composition of the kit with the respective initiator component.Type: ApplicationFiled: February 14, 2003Publication date: September 18, 2003Applicant: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Publication number: 20030144136Abstract: The present invention is for a transition metal-free catalyst system for synthesizing high molecular weight, linear polymers. The system comprises a catalyst composition having: (a) a neutral compound having the formula AlR3, wherein R is an alkyl or hydride group; (b) a Lewis acid or Lewis acid derivative cocatalyst different from the neutral compound, wherein the cocatalyst reacts with the neutral compound to form an initiator; and (c) an activity-enhancing modifier, wherein the modifier reacts with the initiator to form the catalyst composition. The instant invention is also directed to a method for polymerizing at least one olefinic monomer comprising the step of contacting a feed containing the olefinic monomer under polymerization conditions with the transition metal-free catalyst composition.Type: ApplicationFiled: January 15, 2002Publication date: July 31, 2003Inventors: Lisa Saunders Baugh, Joseph Anthony Sissano
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Patent number: 6515088Abstract: A new class of “living” free radical initiators that are based on alkylperoxydiarylborane and its derivatives and that may be represented by the general formula. R—[O—O—B—&phgr;1(—&phgr;2)]n wherein n is from 1 to 4, R is a hydrogen or a linear, branched or cyclic alkyl radical having a molecular weight from 1 to about 500, and &phgr;1 and &phgr;2, independently, are selected from aryl radicals, based on phenyl or substituted phenyl groups, with the proviso that &phgr;1 and &phgr;2 can be the chemically bridged to each other with a linking group or with a direct chemical bond between the two aryl groups to form a cyclic ring structure that includes a boron atom are disclosed.Type: GrantFiled: May 30, 2002Date of Patent: February 4, 2003Assignee: The Penn State Research FoundationInventor: Tze-Chiang Chung
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Patent number: 6489416Abstract: Ethylene and/or propylene are polymerized to form high molecular weight, linear polymers by contacting ethylene and/or propylene monomer, in the presence of an inert reaction medium, with a catalyst system which consists essentially of (1) an aluminum alkyl component, such as trimethylaluminum, triethylaluminum, triisobutylaluminum, tri-n-octylaluminum and diethylaluminum hydride and (2) a Lewis acid or Lewis acid derivative component, such as _B(C6F5)3, {(CH3)2N(H)(C6H5)}+{B(C6F5)4}−, {(C2H5) 3NH}+{B(C6F5)4}−, {(C6F5)3C}+{B(C6F5)4}−, {(C6F5)3C}+{B(C6F5)3(Cl)−}, (C2H5) 2Al(OCH3), (C2H5)2Al(2,6-di-t-butyl-4-methylphenoxide), (C2H5)Al(2,6-di-t-butylphenoxide)2, (C2H5)2Al(2,6-di-t-butylphenoxide), 2,6-di-t butylphenol.methyl-aluminoxane or an alkylaluminoxane, and which may be completely free any transition metal component(s).Type: GrantFiled: February 7, 2001Date of Patent: December 3, 2002Assignee: The Penn State Research FoundationInventors: Ayusman Sen, Louis M. Wojcinski, II, Shengsheng Liu
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Patent number: 6479602Abstract: Polymerization initiator systems comprising an organoborane and a vinyl aromatic compound are described. The polymerization initiator systems are particularly useful in formulating two-part curable bonding compositions, particularly those that cure to acrylic adhesives, more particularly those that cure to acrylic adhesives capable of bonding low surface energy substrates. Also described are bonding compositions comprising an organoborane, at least one polymerizable monomer, and at least one vinyl aromatic compound.Type: GrantFiled: March 15, 2000Date of Patent: November 12, 2002Assignee: 3M Innovative PropertiesInventor: Dean M. Moren
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Publication number: 20020120054Abstract: Reactive systems for polymerizing ethylenically unsaturated compounds comprising a first component, comprised of ethylenically unsaturated compounds capable of polymerization, and a second component of a hardener system comprised of organoboron compounds which are stabilized with suitable oligomers. An organic peroxide (perester, hydroperoxide, perether and/or peranhydride) is admixed with the compounds. These components are mixed to form a polymer. The reactive system reaches full strength in reduced time with the use of the organic peroxide and are suitable for joining hard body materials in human or animal tissue, in particular in the surgical and/or dental sector, in the production of body-absorbable or body-resistant adhesives, cements, and/or filling compounds and for forming synthetic material moldings.Type: ApplicationFiled: September 10, 1999Publication date: August 29, 2002Inventors: WOLFGANG RITTER, ROBERT WENZ, PETER POKINSKYJ
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Patent number: 6437065Abstract: Reactive systems for polymerizing ethylenically unsaturated compounds comprising a first component, comprised of ethylenically unsaturated compounds capable of polymerization, and a second component of a hardener system comprised of organoboron compounds which are stabilized with suitable oligomers. An organic peroxide (perester, hydroperoxide, perether and/or peranhydride)is admixed with the compounds. These components are mixed to form a polymer. The reactive system reaches full strength in reduced time with the use of the organic peroxide and are suitable for joining hard body materials in human or animal tissue, in particular in the surgical and/or dental sector, in the production of body-absorbable or body-resistant adhesives, cements, and/or filling compounds and for forming synthetic material moldings.Type: GrantFiled: September 10, 1999Date of Patent: August 20, 2002Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Wolfgang Ritter, Robert Wenz, Peter Pokinskyj
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Patent number: 6420502Abstract: A new class of “living” free radical initiators that are based on alkylperoxydiarylborane and its derivatives and that may be represented by the general formula. R—[O—O—B-&phgr;1(-&phgr;2)]n wherein n is from 1 to 4, R is a hydrogen or a linear, branched or cyclic alkyl radical having a molecular weight from 1 to about 500, and &phgr;1 and &phgr;2, independently, are selected from aryl radicals, based on phenyl or substituted phenyl groups, with the proviso that &phgr;1 and &phgr;2 can be the chemically bridged to each other with a linking group or with a direct chemical bond between the two aryl groups to form a cyclic ring structure that includes a boron atom are disclosed.Type: GrantFiled: June 25, 2001Date of Patent: July 16, 2002Assignee: The Penn State Research FoundationInventor: Tze-Chiang Chung
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Publication number: 20020091211Abstract: A new class of “living” free radical initiators that are based on alkylperoxydiarylborane and its derivatives and that may be represented by the general formula.Type: ApplicationFiled: June 25, 2001Publication date: July 11, 2002Inventor: Tze-Chiang Chung
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Patent number: 6410667Abstract: Initiator systems of the invention comprise a complexed initiator comprising a complex of an amidine complexing agent and an initiator; and a decomplexer. The initiator systems are useful for initiating polymerization of at least one monomer to form polymerized compositions. Kits of the invention useful for forming the polymerized compositions comprise a polymerizable composition and an initiator component, wherein the initiator component comprises a complexed amidine initiator. Bonding compositions can be prepared by mixing the polymerizable composition of the kit with the respective initiator component.Type: GrantFiled: November 4, 1999Date of Patent: June 25, 2002Assignee: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Patent number: 6395847Abstract: The invention is directed to organometallic catalysts prepared by a process comprising a) combining nucleophilic group-containing particulate support material with an arylboron or arylaluminum Lewis acid compound in the presence of a Lewis base compound; b) contacting the product of a) with a trialkylaluminum compound before combining said product with a metal precursor compound capable of activation for olefin polymerization by said product a); and, c) combining the product of b) with said metal precursor compound. These catalyst compositions are suitable for addition reactions of ethylenically and acetylenically unsaturated monomers. The invention includes a polymerization process of combining or contacting olefinically unsaturated monomers with the invention catalyst composition. Use of the invention catalyst to polymerize &agr;-olefins is exemplified.Type: GrantFiled: November 19, 1999Date of Patent: May 28, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventor: Main Chang
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Patent number: 6384165Abstract: A composition comprises organoborane amine complex and 1,4-dioxo-2-butene-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: GrantFiled: February 15, 2001Date of Patent: May 7, 2002Assignee: 3M Innovative Properties Co.Inventor: Dean M. Moren
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Publication number: 20020040116Abstract: A composition comprises organoborane amine complex and 1,4-dioxo-2-butene-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: ApplicationFiled: February 15, 2001Publication date: April 4, 2002Applicant: 3M Innovative Properties CompanyInventor: Dean M. Moren
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Patent number: 6355749Abstract: A new class of ferroelectric terpolymers having an exceptionally large electrostrictive response (>3%) induced by external electric field at ambient temperature comprise 50-80 mole % of vinylidene fluoride (VDF), 15-40 mole % of trifluoroethylene (TrFE) and 2-20 mole % of at least one bulky monomer, such as chlorotrifluoroethylene (CTFE) or hexafluoropropene (HFP). These semicrystalline terpolymers behave like a ferroelectric relaxor having a rapid electric field-induced mechanical response, due to a low Curie temperature (phase transition between polar and nonpolar crystalline domains at or near ambient temperature) and high dielectric constant. A combination of bulk polymerization and free radical polymerization using oxidation adducts of an organoborane as the free radical initiator may be used to prepare the terpolymers, such that the terpolymers are characterized by good processibility, high purity and uniform molecular structure.Type: GrantFiled: December 5, 2000Date of Patent: March 12, 2002Assignee: The Penn State Research FoundationInventors: Tze-Chiang Chung, Atitsa Petchsuk
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Patent number: 6350834Abstract: In a process for the homopolymerization of vinylaromatic monomers or the copolymerization of vinylaromatic monomers and dienes in the presence of at least one alkali metal compound and at least one compound of an element of group 3a of the Periodic Table of the elements, the compounds contain, based on the sum of molar equivalents of alkali metal and elements of group 3a, in each case a) from 0.1 to 3.9 molar equivalents of oxygen, sulfur, nitrogen or phosphorus and b) from 0.1 to 3.9 molar equivalents of an organyl ligand.Type: GrantFiled: August 14, 2000Date of Patent: February 26, 2002Assignee: BASF AktiengesellschaftInventors: Christian Schade, Wolfgang Fischer, Hermann Gausepohl, Konrad Knoll, Volker Warzelhan, Michel Fontanille, Alain Deffieux, Philippe Desbois
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Publication number: 20010031844Abstract: Ethylene and/or propylene are polymerized to form high molecular weight, linear polymers by contacting ethylene and/or propylene monomer, in the presence of an inert reaction medium, with a catalyst system which consists essentially of (1) an aluminum alkyl component, such as trimethylaluminum, triethylaluminum, triisobutylaluminum, tri-n-octylaluminum and diethylaluminum hydride and (2) a Lewis acid or Lewis acid derivative component, such as B(C6F5)3, {(CH3)2N(H)(C6H5)}+{B(C6F5)4}−, {(C2H5) 3NH}+{B(C6F5)4}−, {(C6F5)3C}+{B(C6F5)4}−, {(C6F5)3C}+{B(C6F5)3(Cl)−}, (C2H5) 2Al(OCH3), (C2H5)2Al(2,6-di-t-butyl-4-methylphenoxide), (C2H5)Al(2,6-di-t-butylphenoxide)2, (C2H5)2Al(2,6-di-t-butylphenoxide), 2,6-di-t butylphenol.methyl-aluminoxane or an alkylaluminoxane, and which may be completely free any transition metal component(s).Type: ApplicationFiled: February 7, 2001Publication date: October 18, 2001Inventors: Ayusman Sen, Louis M. Wojcinski, Shengsheng Liu
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Patent number: 6294626Abstract: A single-site olefin polymerization catalyst is described. The catalyst comprises an activator and an organometallic compound that includes a Group 3 to 10 transition or lanthanide metal, M, and a modified boraaryl ligand. We surprisingly found that the catalyst is more active in olefin polymerization compared to other catalysts containing non-modified boraaryl ligands. Most surprisingly, the supported catalyst gives polyolefins with a multimodal molecular weight distribution having separate components of distinct molecular weight.Type: GrantFiled: November 15, 1999Date of Patent: September 25, 2001Assignee: Equistar Chemicals, LPInventors: Shaotian Wang, Jean A. Merrick-Mack
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Patent number: 6284381Abstract: A polymerizable acrylic composition comprises: (a) at least one acrylic monomer; (b) an effective amount of an organoborane amine complex having the structure: wherein: R1 is an alkyl group having 1 to 10 carbon atoms; R2 and R3 are independently selected from phenyl-containing groups and alkyl groups having 1 to 10 carbon atoms; R4 is selected from the group consisting of CH2CH2OH and (CH2)xNH2 wherein x is an integer greater than 2; R5 is hydrogen or an alkyl group having 1 to 10 carbon atoms; and the nitrogen atom to boron atom ratio is about 1:1 to 1.5:1; and (c) an effective amount of an acid for initiating polymerization of the acrylic monomer. The polymerizable acrylic compositions are especially useful for bonding low surface energy substrates.Type: GrantFiled: November 14, 1997Date of Patent: September 4, 2001Assignee: 3M Innovative Properties CompanyInventors: Jury V. Zharov, Jury N. Krasnov
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Patent number: 6252023Abstract: A composition comprises organoborane amine complex and 1,4-dioxo-2-butene-functional material. The composition can form a part of a polymerization initiator system that also includes a compound that is reactive with the amine portion of the complex. The system can be used to initiate polymerization of acrylic monomer and to form an acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.Type: GrantFiled: March 19, 1999Date of Patent: June 26, 2001Assignee: 3M Innovative Properties CompanyInventor: Dean M. Moren