Contains P, S, Or N Atom Other Than As Elemental Nitrogen Patents (Class 526/198)
  • Patent number: 11732156
    Abstract: A primer is useful for adhering cured silicones to low energy plastic substrates. The primer is prepared from starting materials including a) an organoboron compound capable of forming a free radical generating species, and at least one of b) an organosilicon compound having, per molecule, at least one free radical reactive group and at least one other reactive group, and/or c) an organoborane liberating compound capable of reacting with starting material a) to liberate the free radical generating species. The method for forming the primer may further include use of d) an organic solvent, and e) a free radical polymerizable monomer, oligomer, macromonomer, or polymer.
    Type: Grant
    Filed: March 9, 2018
    Date of Patent: August 22, 2023
    Assignee: DOW SILICONES CORPORATION
    Inventor: Bizhong Zhu
  • Patent number: 10995240
    Abstract: An acrylic adhesive composition includes a first part including an aminoborane initiator and acrylate or/and methacrylate monomers, and a second part including inert microcapsules of a cure activator and acrylate monomers, wherein the microcapsules are breakable, such that when broken, the first part reacts with the second part and the acrylic adhesive begins to cure. A two-part structural adhesive includes a suspension component containing an aminoborane initiator, and microcapsules containing an encapsulated component, wherein the microcapsules are dispersed in the suspension component. A method of activating an aminoborane initiator suspension to form a structural adhesive includes adding microcapsules containing an encapsulated component, to the aminoborane initiator suspension at a predetermined ratio, and breaking the microcapsules to activate curing.
    Type: Grant
    Filed: July 20, 2018
    Date of Patent: May 4, 2021
    Assignee: PALO ALTO RESEARCH CENTER INCORPORATED
    Inventors: Gabriel Iftime, Jessica Louis Baker Rivest
  • Patent number: 9482896
    Abstract: The invention relates to an acrylic adhesive composition, more particularly, to an adhesive composition which: specifies the contents of a (meth)acrylic ester-based monomer and an aromatic group-containing monomer of an acrylic copolymer as a composition having little or no difference of birefringence; has excellent durability; and can reduce light leakage due to flexure by mixing a crosslinkable functional group-containing acrylic copolymer (A) and an acrylic copolymer (B) which does not contain the crosslinkable functional group, in a ratio of 1:9 to 5:5.
    Type: Grant
    Filed: January 12, 2009
    Date of Patent: November 1, 2016
    Assignee: LG Chem, Ltd.
    Inventors: Se Ra Kim, Kee Young Kim, Sung Soo Yoon, Min Ki Lee, No Ma Kim, In Cheon Han
  • Patent number: 9018326
    Abstract: A two-part acrylic adhesive composition comprising at least one organoborane-amine complex initiator and at least one multifunctional maleimide crosslinker.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: April 28, 2015
    Assignee: IPS Corporation
    Inventor: Xiaoyi Xie
  • Patent number: 8840965
    Abstract: In various embodiments, provided are silicon-containing coatings; silicon-containing coatings comprising microstructures that are responsive to one or more stimuli; oxidized products of said silicon-containing coatings; bulk solids; oxidized solids and powders; methods of preparing such coatings, solids, and powders; and substrates comprising the provided coatings.
    Type: Grant
    Filed: October 14, 2011
    Date of Patent: September 23, 2014
    Assignee: Dow Corning Corporation
    Inventors: Dongchan Ahn, Jeremy M. Beebe
  • Patent number: 8829127
    Abstract: The invention relates to a continuous polymerization process for preparing a random ethylene interpolymer which comprises: (A) polymerizing ethylene, and an ?-olefin comonomer selected from propylene and/or 1-butene, and mixtures thereof, under continuous random polymerization conditions in the presence of single site catalyst system employing an ionic activator having cyclic ligands shielding a central charge bearing atom, at a temperature of 140° C. to 250° C. at a conversion of ethylene of 80 to 99% and a comonomer conversion of from at least 20%; and (B) devolatilizing the polymer to provide an ethylene copolymer having a density of from 0.85 to 0.92 g/cm3, an MI of from 0.01 to 100 g/10 min and an I21/I2 of from 30 to 400.
    Type: Grant
    Filed: August 7, 2012
    Date of Patent: September 9, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Narayanaswami Raja Dharmarajan, Rui Zhao, Bruce Allan Harrington, George James Pehlert, Periagaram S. Ravishankar, Kent L. Chasey
  • Patent number: 8652578
    Abstract: A method of forming a cured coating composition on an automobile component is provided. The method utilizes a coating compound including a radical polymerizable compound and an organoborane initiator and includes the step of applying the coating composition to the automobile component. The organoborane initiator is complexed with a bi-functional noncyclic blocking agent that has a carbon backbone and two organoborane complexing moieties. The two moieties are different from each other and are selected from the group of an amine moiety, a thiol moiety, and a phosphine moiety. In addition, the two moieties are separated from each other by two to four carbon atoms to increase the nucleophilicity of the blocking agent towards the organoborane initiator. The organoborane initiator is decomplexed from the blocking agent thereby forming a radical that is used to polymerize the radical polymerizable compound and cure the coating composition on the automobile component.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: February 18, 2014
    Assignee: BASF SE
    Inventors: David Cranfill, Keith E. Gutowski
  • Publication number: 20130267670
    Abstract: A two-part acrylic adhesive composition comprising at least one organoborane-amine complex initiator and at least one multifunctional maleimide crosslinker.
    Type: Application
    Filed: March 12, 2013
    Publication date: October 10, 2013
    Applicant: IPS CORPORATION
    Inventor: Xiaoyi Xie
  • Patent number: 8501886
    Abstract: The invention is a two part polymerizable composition comprising in one part an organoboron compound capable of forming free radical generating species amine complex and in the second part one or more compounds capable of free radical polymerization and a cure accelerator comprising a) at least one compound containing a quinone structure or b) at least one compound containing at least one aromatic ring and one or more, preferably two substituents on the aromatic ring selected from hydroxyl, ether and both, where there are two substituents they are located either ortho or para with respect to one another and a peroxide containing compound. The second part may further contain an agent capable of causing the organoboron compound to form free radical generating species upon contacting the two parts. The first part may further comprises one or more compounds capable of free radical polymerization. This facilitates formulating compositions that have commercially desirable volumetric ratios of the two parts.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: August 6, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Gary L. Jialanella, Dean A. Johnson
  • Publication number: 20130035460
    Abstract: The invention relates to a continuous polymerization process for preparing a random ethylene interpolymer which comprises: (A) polymerizing ethylene, and an ?-olefin comonomer selected from propylene and/or 1-butene, and mixtures thereof, under continuous random polymerization conditions in the presence of single site catalyst system employing an ionic activator having cyclic ligands shielding a central charge bearing atom, at a temperature of 140° C. to 250° C. at a conversion of ethylene of 80 to 99% and a comonomer conversion of from at least 20%; and (B) devolatilizing the polymer to provide an ethylene copolymer having a density of from 0.85 to 0.92 g/cm3, an MI of from 0.01 to 100 g/10 min and an I21/I2 of from 30 to 400.
    Type: Application
    Filed: August 7, 2012
    Publication date: February 7, 2013
    Inventors: Narayanaswami R. DHARMARAJAN, Rui Zhao, Bruce Allan Harrington, George James Pehlert, Periagaram S. Ravishankar, Kent L. Chasey
  • Patent number: 8236910
    Abstract: Cycloolefin copolymers which are distinguished by the presence of racemic diads of repeating polycyclic units and additionally by racemic triads of repeating polycyclic units are described. These copolymers can be prepared by copolymerization of polycyclic olefins with linear olefins in the presence of metallocene catalysts which have no Cs symmetry in relation to the centroid-M-centroid plane. The novel copolymers can be used for the production of shaped articles, in particular of films.
    Type: Grant
    Filed: March 19, 2008
    Date of Patent: August 7, 2012
    Assignee: Topas Advanced Polymers GmbH
    Inventors: Dieter Ruchatz, Anne-Meike Schauwienold, Peter Jörg
  • Patent number: 8138286
    Abstract: Cycloolefin copolymers which are distinguished by the presence of racemic diads of repeating polycyclic units and additionally by racemic triads of repeating polycyclic units are described. These copolymers can be prepared by copolymerization of polycyclic olefins with linear olefins in the presence of metallocene catalysts which have no Cs symmetry in relation to the centroid-M-centroid plane. The novel copolymers can be used for the production of shaped articles, in particular of films.
    Type: Grant
    Filed: March 19, 2008
    Date of Patent: March 20, 2012
    Assignee: Topas Advanced Polymers GmbH
    Inventors: Dieter Ruchatz, Anne-Meike Schauwienold, Peter Jörg
  • Patent number: 8114947
    Abstract: The invention is a two part polymerizable composition comprising in one part an organoboron compound capable of forming free radical generating species amine complex and in the second part one or more compounds capable of free radical polymerization and a cure accelerator comprising a) at least one compound containing a quinone structure or b) at least one compound containing at least one aromatic ring and one or more, preferably two substituents on the aromatic ring selected from hydroxyl, ether and both, where there are two substituents they are located either ortho or para with respect to one another and a peroxide containing compound. The second part may further contain an agent capable of causing the organoboron compound to form free radical generating species upon contacting the two parts. The first part may further comprises one or more compounds capable of free radical polymerization. This facilitates formulating compositions that have commercially desirable volumetric ratios of the two parts.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: February 14, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: Gary L. Jialanella, Dean A. Johnson
  • Publication number: 20110294958
    Abstract: A non-random copolymer is formed, and its structure controlled, using a method including the step of combining a mixture of a first radical polymerizable compound and an organoborane initiator, a second radical polymerizable compound, and an organoborane decomplexing agent, at a rate sufficient to form the non-random copolymer. The non-random copolymer may be a silicon gradient polymer. To form the silicon gradient copolymer, the first and second radical polymerizable compounds are polymerized in the presence of the organoborane initiator and the organoborane decomplexing agent. The silicon gradient copolymer has a polymer backbone consisting of organic moieties and has at least one silicon containing pendent group.
    Type: Application
    Filed: February 2, 2010
    Publication date: December 1, 2011
    Inventors: Dongchan Ahn, Corissa K. Lee, Christopher L. Wong
  • Publication number: 20110129683
    Abstract: A radical polymerizable composition includes a radical polymerizable compound and an organoborane-azole complex. The organoborane-azole complex includes an azole having at least two nitrogen atoms wherein at least one nitrogen atom is an sp3 nitrogen atom and is substituted. A method of forming the composition includes the step of combining the radical polymerizable compound and the organoborane-azole complex to form the composition. The method also includes the step of polymerizing the composition. A composite article which includes a substrate and a cured composition disposed on the substrate is also provided. The cured composition is formed from polymerization of the composition.
    Type: Application
    Filed: July 27, 2009
    Publication date: June 2, 2011
    Inventors: Dongchan Ahn, Gang Lu
  • Patent number: 7928174
    Abstract: Organosilicon functional boron amine catalyst complexes have an organosilicon functional organoborane portion of the complex that contains at least one silicon atom. The complexes can be used as components in curable compositions containing (i) a free radical polymerizable monomer, oligomer or polymer; (ii) the organosilicon functional boron amine catalyst complex; and (iii) an amine reactive compound having amine reactive groups. The curable compositions may contain a component capable of generating a gas, as well as various other optional ingredients. These curable compositions can be used as rubbers, tapes, adhesives, protective coatings, thin films, thermoplastic monolithic molded parts, thermosetting monolithic molded parts, sealants, foams, gaskets, seals, o-rings, pressure sensitive adhesives, die attachment adhesives, lid sealants, encapsulants, potting compounds, conformal coatings, and electronic components.
    Type: Grant
    Filed: December 13, 2005
    Date of Patent: April 19, 2011
    Assignee: Dow Corning Corporation
    Inventors: Dongchan Ahn, Mohamed Mustafa, Patricia Olney
  • Publication number: 20110028654
    Abstract: Disclosed is a method of producing a polyolefin composition comprising contacting a metallocene pre-catalyst, co-catalyst, and a stoichiometric excess of a metal alkyl; adding a first olefin monomer; and polymerizing the first monomer for a time sufficient to form the polyolefin. The method allows for the use of minimum amounts of activating co-catalyst and metallocene pre-catalyst. Also disclosed is a method of producing a block polyolefin composition comprising contacting a metallocene pre-catalyst, a co-catalyst, and a stoichiometric excess of a metal alkyl; adding a first olefin monomer; polymerizing the first monomer for a time sufficient to form the polyolefin; adding a second monomer; and polymerizing the second olefin monomer for a time sufficient to form said block polyolefin composition. Also disclosed are amorphous atactic polymer and copolymer compositions made according to the present invention.
    Type: Application
    Filed: November 10, 2008
    Publication date: February 3, 2011
    Applicant: University of Maryland, college Park Office of Technology Commercialization
    Inventors: Lawrence R. Sita, Wei Zhang
  • Patent number: 7816562
    Abstract: The invention is amido-borate compounds containing one or more anionic amido-borate moieties comprising an organoborate anion wherein the boron atom is bonded to a nitrogen atom of ammonia or an organic compound containing one or more nitrogen atoms, such as a hydrocarbyl amine, a hydrocarbyl polyamine, or an aromatic heterocycle containing one or more nitrogen atoms, and a cationic counter ion.
    Type: Grant
    Filed: October 6, 2006
    Date of Patent: October 19, 2010
    Assignee: Dow Global Technologies Inc.
    Inventors: Shaoguang Feng, Gary L. Jialanella, Peter Nickias, Toni Ristoski
  • Patent number: 7737241
    Abstract: The invention is a system for initiating free radical polymerization comprising: a) in one part, one or more amido-borate compounds containing one or more anionic amido-borate moieties comprising an organoborate wherein the boron atom is bonded to a nitrogen atom of ammonia or an organic compound containing one or more nitrogen atoms, such as a hydrocarbyl amine, a hydrocarbyl polyamine, or an aromatic heterocycle containing one or more nitrogen atoms and optionally containing one or more heteroatoms or heteroatom containing functional moieties, and one or more cationic counter ions and b) in a second part, a liberating compound which reacts with the nitrogen atom(s) bound to the boron atom(s) upon contact with the amido-borate to form an organoborane radical.
    Type: Grant
    Filed: October 6, 2006
    Date of Patent: June 15, 2010
    Assignee: Dow Global Technologies Inc.
    Inventors: Shaoguang Feng, Gary L. Jialanella, Peter Nickias, Toni Ristoski
  • Patent number: 7649068
    Abstract: A polymerized product is obtained from a mixture containing (i) a free radical polymerizable monomer, oligomer or polymer; (ii) an organoborane amine complex, (iii) a poor or non-solvent for the polymerized product of (i); and (iv) an amine reactive compound. The mixture may include (v) an active ingredient to be encapsulated by the polymerized product, and (vi) an optional component(s). Polymer particles are obtained by (A) forming a composition containing components (i)-(iv); (B) agitating components (i)-(iv) in the presence of oxygen to initiate polymerization, at a rate and for a time sufficient to provide a uniform dispersion and reaction of the components; (C) allowing the reaction to proceed to completion at room temperature; and (D) recovering the polymer particles by removing component (iii). The composition may include (v) the active ingredient to be encapsulated by the polymer particles.
    Type: Grant
    Filed: January 11, 2006
    Date of Patent: January 19, 2010
    Assignee: Dow Corning Corporation
    Inventor: Dongchan Ahn
  • Patent number: 7595369
    Abstract: A method of copolymerizing cyclic olefins and polar vinyl olefins, a copolymer produced by the method, and an optical anisotropic film including the copolymer are provided. According to the copolymerization method, a cyclic olefin and a polar vinyl olefin can be effectively copolymerized using a catalyst system composed of a compound containing a group 13 element and a radical initiator. The resulting copolymer is transparent, and has high adhesion, thermal stability, optical anisotropy and strength, and a low dielectric constant. The optical film including the copolymer can be used as a plastic lens, a polarizer protective film, an adhesive film, and a compensation film, and in a LCD display.
    Type: Grant
    Filed: November 9, 2005
    Date of Patent: September 29, 2009
    Assignee: LG Chem, Ltd.
    Inventors: Sung Cheol Yoon, Sung Ho Chun, Heon Kim, Tae Sun Lim, Jung Min Lee
  • Publication number: 20080295961
    Abstract: The invention is a two part polymerizable composition comprising in one part an organoboron compound capable of forming free radical generating species and in the second part one or more compounds capable of free radical polymerization and from about 20 to about 30 parts by weight based on the weight of the second part of i) a halogenated polyolefin having halosulfonyl groups or ii) a mixture of a halogenated polyolefin and an organic sulfonyl halide. The second part may further contain a compound capable of causing the organoboron compound to form free radical generating species upon contacting the two parts. The first part may further comprise one or more compounds capable of free radical polymerization.
    Type: Application
    Filed: July 30, 2008
    Publication date: December 4, 2008
    Applicant: DOW GLOBAL TECHNOLOGIES INC.
    Inventors: Gary L. Jialanella, Toni Ristoski, Arthur F. Cawley, Eric E. Cole, Dean A. Johnson
  • Publication number: 20080249267
    Abstract: Preparation of highly reactive isobutene homo- or copolymers having Mn=from 500 to 45 000 by polymerizing isobutene in the liquid phase in the presence of a dissolved, dispersed or supported boron-containing catalyst complex, by using, as the catalyst complex, a protic acid compound I [H+]m+1[R1R2R3B—(-Am+—BR5R6—)n—R4](m+1)?.Lx ??(I) R1 to R6 each independently aliphatic, heterocyclic or aromatic, fluorinated hydrocarbon radicals having in each case from 1 to 18 carbon atoms, or silyl groups comprising C1 to C18 hydrocarbon radicals, A nitrogen-containing bridging member which forms covalent bonds to the boron atoms via its nitrogen atoms, L neutral solvent molecules, n=0 or 1, m=0 or 1 and x is ?0.
    Type: Application
    Filed: November 15, 2006
    Publication date: October 9, 2008
    Applicant: BASF SE
    Inventors: Phillip Hanefeld, Volker Bohm, Marcus Sigl, Nina Challand, Michael Roper, Hans-Michael Walter, Brigitte Voit, Fritz Elmar Kuehn, Ahmed Hijazi, Radha Krishnan Narayanan
  • Publication number: 20080132661
    Abstract: A heterogeneous catalyst component obtainable by contacting: (a) a solid Lewis acid of formula MR1a wherein M is a metal of group 1-12 of the Periodic Table of the Elements; R1 is a fluorine, chlorine, bromine or iodine atom; and a is equal to the valence of the metal M; and (b) at least one ionic compound of formula (I) [((T)pR2)nMI(R3)m]?[D]+(I) wherein: MI is an element belonging to group 13 of the Periodic Table of the Elements; R3, equal to or different from each other, are halogen atoms, halogenated C6-C20 aryl and halogenated C7-C20 alkylaryl groups; two R1 groups, can also form with the element M one condensed ring; R2, equal to or different from each other, are hydrocarbon groups; T is a Lewis base in its neutral form; n ranges from 1 to 4; m ranges from 0 to 3; and m+n=4; p ranges from 1 to 10; and [D]+ is a monovalent cation.
    Type: Application
    Filed: February 24, 2004
    Publication date: June 5, 2008
    Applicant: BASELL POLYOLEFINE GmbH
    Inventors: Vincenzo Busico, Mauro Guardasole, Roberta Cipullo, Luigi Resconi, Giampiero Morini
  • Patent number: 7235617
    Abstract: 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: Grant
    Filed: April 19, 2004
    Date of Patent: June 26, 2007
    Assignee: Dow Global Technologies Inc.
    Inventors: Steven P. Webb, Mark F. Sonnenschein
  • Patent number: 7202373
    Abstract: Monocyclopentadienyl complexes in which the cyclopentadienyl system bears at least one uncharged donor bound via a boron-containing bridge and comprising one or more atoms of group 15 and/or 16 of the Periodic Table of the Elements and is bound to a metal selected from the group consisting of titanium in the oxidation state 3, vanadium, chromium, molybdenum and tungsten, a catalyst system comprising at least one of the monocyclopentadienyl complexes, the use of the catalyst system for the polymerization or copolymerization of olefins and a process for preparing polyolefins by polymerization or copolymerization of olefins in the presence of the catalyst system and polymers obtainable in this way.
    Type: Grant
    Filed: August 18, 2003
    Date of Patent: April 10, 2007
    Assignee: Basell Polyolefine GmbH
    Inventor: Shahram Mihan
  • Patent number: 7202317
    Abstract: A method is provided for cationically polymerizing olefin monomer by using a novel coinitiator in the presence of water. More specifically, a method is provided for cationically polymerizing olefin monomer by using a novel coinitiator in an aqueous suspension or aqueous emulsion polymerization process.
    Type: Grant
    Filed: April 2, 2004
    Date of Patent: April 10, 2007
    Assignee: The University of Akron
    Inventors: Joseph P. Kennedy, Scott Collins, Stewart P. Lewis
  • Patent number: 7196149
    Abstract: A method is provided for cationically polymerizing olefin monomer by employing the step of using a novel coinitiator in an organic phase or a neat monomer reaction phase. More specifically, a method is provided for cationically polymerizing olefin monomer by employing the step of using a novel coinitiator in an organic phase or a neat monomer reaction phase, wherein the organic phase is a hydrocarbon solution of the monomer or a halogenated-hydrocarbon solution of the monomer and wherein the neat-monomer reaction phase is a liquid monomer.
    Type: Grant
    Filed: April 2, 2004
    Date of Patent: March 27, 2007
    Assignee: The University of Akron
    Inventors: Scott Collins, Warren E. Piers, Stewart P. Lewis
  • Patent number: 7189303
    Abstract: 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: Grant
    Filed: August 31, 2004
    Date of Patent: March 13, 2007
    Assignee: 3M Innovative Properties Company
    Inventors: Edward J. Deviny, Dean M. Moren
  • Patent number: 7151072
    Abstract: The invention provides initiator systems capable of initiating polymerization. More specifically, the invention relates to initiator systems comprising a complexed initiator and a ?-ketone compound decomplexer. The invention further relates to the use of these initiator systems for initiating polymerization, as well as kits, bonding compositions, and polymerized compositions made therewith, and coated substrates and bonded articles prepared therefrom.
    Type: Grant
    Filed: October 21, 2004
    Date of Patent: December 19, 2006
    Assignee: 3M Innovative Properties Company
    Inventor: Dean M. Moren
  • Patent number: 7030169
    Abstract: Compositions are provided that that can be used as an initiator system for free radical polymerization reactions. More specifically, the initiator systems include an electron acceptor and an electron donor. The electron donors are arylsulfinate salts having a cation that contains at least one carbon atom and either a positively charged nitrogen atom or a positively charged phosphorus atom. Methods of polymerization are also provided that can be used to prepare polymeric material with the initiator systems. The initiator systems can be thermal initiator systems, photoinitiator systems, or combinations thereof.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: April 18, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Rajdeep S. Kalgutkar, Michael C. Palazzotto
  • Patent number: 6951909
    Abstract: The present invention is directed to a polymerizable system. The polymerizable system comprises an organoborane, at least one polymerizable monomer, and a work-life extending agent.
    Type: Grant
    Filed: May 25, 2004
    Date of Patent: October 4, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: E. John Deviny, Virginia C. Marhevka
  • Patent number: 6939932
    Abstract: Use of an initiator system comprising: a combination of an organoborane and a polyaziridine, in a ratio of aziridine groups to boron atoms of greater than 1.3:1, as an initiator of polymerisation in an adhesive composition for bonding a low surface energy substrate; provided that the initiator system does not contain more than a trace amount of a complex of organoborane with a complexing agent selected from: an amine other than a polyaziridine; a complexing agent comprising at least one hydroxide; a complexing agent comprising at least one alkoxide; or amidine complexing agent.
    Type: Grant
    Filed: April 21, 2003
    Date of Patent: September 6, 2005
    Assignee: Loctite (R&D) Limited
    Inventors: Brendan J. Kneafsey, Gerry Coughlan
  • Patent number: 6806330
    Abstract: 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: Grant
    Filed: December 17, 1999
    Date of Patent: October 19, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Mark F. Sonnenschein, Steven P. Webb, Nelson G. Rondan
  • Publication number: 20040198935
    Abstract: 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: Application
    Filed: April 19, 2004
    Publication date: October 7, 2004
    Inventors: Steven F. Webb, Mark F. Sonnenschein
  • Patent number: 6762260
    Abstract: 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: Grant
    Filed: March 5, 2002
    Date of Patent: July 13, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Mark F. Sonnenschein, Steven P. Webb, Benjamin L. Wendt, Daniel D. Harrington
  • Patent number: 6762261
    Abstract: The present invention is directed to a polymerizable system. The polymerizable system comprises an organoborane, at least one polymerizable monomer, and a work-life extending agent.
    Type: Grant
    Filed: February 21, 2002
    Date of Patent: July 13, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: E. John Deviny, Virginia C. Marhevka
  • Patent number: 6740716
    Abstract: 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: Grant
    Filed: October 30, 2001
    Date of Patent: May 25, 2004
    Assignee: Dow Global Technologies Inc.
    Inventors: Steven P. Webb, Mark F. Sonnenschein
  • Patent number: 6734268
    Abstract: 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: Grant
    Filed: December 31, 2001
    Date of Patent: May 11, 2004
    Assignee: 3M Innovative Properties Company
    Inventor: Dean M. Moren
  • Publication number: 20040030073
    Abstract: An optically active poly(N-&agr;-methylbenzylmaleimide) represented by the following formula (1): 1
    Type: Application
    Filed: August 6, 2003
    Publication date: February 12, 2004
    Applicant: TOSOH CORPORATION
    Inventor: Tsutomu Oishi
  • Publication number: 20040019163
    Abstract: Control agents that have a nitrogen-nitrogen bond covalently bonded to a thiocarbonyl moiety are provided for living-type free radical polymerization of a wide variety of monomers. These control agents provide superior properties for control of the polymerization and/or the properties of the polymers obtained and/or the monomers that may be polymerized. In some embodiments, a bulky group is pendant off the activated thiocarbonyl portion of the control agents. Multifunctional control agents provide the opportunity for a variety of structurally unique polymers, including block copolymers, stars and hyper-branched polymers.
    Type: Application
    Filed: April 3, 2003
    Publication date: January 29, 2004
    Applicant: Symyx Technologies, Inc.
    Inventors: Dominique Charmot, Han Ting Chang, Wenyue Wang
  • Patent number: 6652281
    Abstract: Dental materials containing monomers and/or prepolymers can be subjected to a polymer-forming reaction. The dental materials comprise at least one initiating system and optionally comprise fillers, colorants, flow modifiers, stabilizers, ion-releasing substances as well as compounds which increase X-ray capacity or other modifiers. The dental materials are characterized in that the initiating system is proportioned such that the dental materials are sufficiently capable of flowing for at least 10 seconds after exposure to oxygen, whereupon they subsequently harden into a solid material.
    Type: Grant
    Filed: February 5, 2002
    Date of Patent: November 25, 2003
    Assignee: 3M ESPE AG
    Inventors: Gunther Eckhardt, Thomas Luchterhandt, Thomas Klettke
  • Publication number: 20030199652
    Abstract: 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: Application
    Filed: January 21, 2003
    Publication date: October 23, 2003
    Applicant: 3M Innovative Properties Company
    Inventors: Edward J. Deviny, Dean M. Moren
  • Patent number: 6632908
    Abstract: 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: Grant
    Filed: March 12, 2002
    Date of Patent: October 14, 2003
    Assignee: Henkel Loctite Corporation
    Inventor: Eerik Maandi
  • Patent number: 6602970
    Abstract: A 2-cyanoacrylate composition comprising a cyclic phenol sulfide derivative. The composition has a high curing rate and is excellent in moist-heat resistance, surface curability and clearance curability.
    Type: Grant
    Filed: June 13, 2001
    Date of Patent: August 5, 2003
    Assignees: Toagosei Co., Ltd., Cosmo Oil Co., Ltd.
    Inventors: Yushi Ando, Seitaro Tajima, Yoshiharu Ohashi, Haruhiko Takeya, Setsuko Miyanari, Toshihiro Kobori
  • Patent number: 6515088
    Abstract: 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: Grant
    Filed: May 30, 2002
    Date of Patent: February 4, 2003
    Assignee: The Penn State Research Foundation
    Inventor: Tze-Chiang Chung
  • Patent number: 6489416
    Abstract: 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: Grant
    Filed: February 7, 2001
    Date of Patent: December 3, 2002
    Assignee: The Penn State Research Foundation
    Inventors: Ayusman Sen, Louis M. Wojcinski, II, Shengsheng Liu
  • Patent number: 6420502
    Abstract: 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: Grant
    Filed: June 25, 2001
    Date of Patent: July 16, 2002
    Assignee: The Penn State Research Foundation
    Inventor: Tze-Chiang Chung
  • Publication number: 20020091211
    Abstract: 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: Application
    Filed: June 25, 2001
    Publication date: July 11, 2002
    Inventor: Tze-Chiang Chung
  • Patent number: 6383655
    Abstract: Low odor polymerizable compositions comprise monomer blends having a average monomer fluorophilicity of at least 3.25, an average boiling point of at least about 160° C., and wherein the monomer blend is polymerizable to a polymer having a glass transition temperature of at least about −20° C. The polymerizable compositions are useful in kits further comprising an aerobic initiator. Also disclosed are bonding compositions, polymerized compositions, coated substrates, and methods of bonding in which the polymerizable compositions are especially useful.
    Type: Grant
    Filed: November 21, 2000
    Date of Patent: May 7, 2002
    Assignee: 3M Innovative Properties Company
    Inventor: Dean M. Moren