With Free Oxygen Or Peroxy Compound Patents (Class 526/197)
  • Patent number: 10889687
    Abstract: A polymerizable composition includes an organoborane-base complex that is a complex of an organoborane and a base, a decomplexing agent that at least partially liberates the organoborane from the organoborane-base complex, a polymerizable thiol-containing component comprising at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon, a hydroperoxide, and a polymerizable ethylenically-unsaturated component comprising at least one polymerizable ethylenically-unsaturated compound having a plurality of ethylenically-unsaturated groups. The combined amounts of the thiol-containing and ethylenically-unsaturated compounds total at least 50 percent by weight of all polymerizable material in the polymerizable composition. The composition may be provide as a two-part composition. Polymerized reaction product of the composition and methods of making the composition are also disclosed.
    Type: Grant
    Filed: September 9, 2016
    Date of Patent: January 12, 2021
    Assignee: 3M Innovative Properties Company
    Inventors: Robert S. Clough, Susan E. DeMoss, Michael A. Kropp
  • Patent number: 8937138
    Abstract: The present invention discloses an initiating system for cationic polymerization and a polymerization process. The present application relates to an initiating system for cationic polymerization of cationic-polymerizable monomers, and a process for cationic polymerization of cationic-polymerizable monomers by using the initiating system. The present invention particular involves an initiating system for cationic polymerization of cationic-polymerizable monomers in an aqueous reaction medium, and a process for cationic polymerization of cationic-polymerizable monomers by using the initiating system in an aqueous reaction medium.
    Type: Grant
    Filed: September 21, 2010
    Date of Patent: January 20, 2015
    Assignees: China Petroleum & Chemical Corporation, Beijing University of Chemical Technology
    Inventors: Yixian Wu, Qiang Huang, Han Zhou, Ruting Jin, Ping He
  • Patent number: 8883943
    Abstract: The present invention relates to isoolefin polymers and process for preparing the same. The present invention especially discloses a polymerization process for the cationic polymerization of isoolefin monomers in an aqueous reaction medium, and isoolefin polymers obtained by such process. In one embodiment, the present invention relates to a polymerization process for the cationic polymerization of isoolefin monomers in an aqueous reaction medium, and isoolefin polymers obtained therefrom. In another embodiment, the present invention relates to a dispersion polymerization process for the cationic copolymerization of isoolefins with conjugated or non-conjugated diolefins and/or vinyl aromatic compounds, and copolymers obtained therefrom.
    Type: Grant
    Filed: September 21, 2010
    Date of Patent: November 11, 2014
    Assignees: China Petroleum & Chemical Corporation, Beijing University of Chemical Technology
    Inventors: Yixian Wu, Qiang Huang, Han Zhou, Ruting Jin, Ping He
  • 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: 8501887
    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: Grant
    Filed: July 27, 2009
    Date of Patent: August 6, 2013
    Assignee: Dow Corning Corporation
    Inventors: Dongchan Ahn, Gang Lu
  • 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
  • Patent number: 8034851
    Abstract: The present invention relates to new cure accelerator systems for anaerobic curable compositions. These anaerobic cure systems include tetraalkyl ammonium oxidizing salts that are soluble in the (meth)acrylate component of the composition.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: October 11, 2011
    Assignee: Henkel Corporation
    Inventor: Philip T. Klemarczyk
  • 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
  • Patent number: 7850870
    Abstract: Conductive curable compositions contain a free radical polymerizable monomer, oligomer or polymer (i); an organoborane amine complex (ii), and an electrically or thermally conductive filler (iii). The conductive curable compositions can also contain an amine reactive compound having amine reactive groups (iv); and (v) a component capable of generating a gas when mixed with a compound bearing active hydrogen and a catalyst. The electrically conductive curable compositions can be used in composite articles of manufacture in which substrates are coated or bonded together with the composition and cured; and as electrically conductive rubbers, electrically conductive tapes, electrically conductive adhesives, electrically conductive foams, and electrically conductive pressure sensitive adhesives.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: December 14, 2010
    Assignee: Dow Corning Corporation
    Inventors: Dongchan Ahn, Mark David Fisher, Andrew Anthony Mojica
  • 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: 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: 20080081195
    Abstract: Chain end functionalized fluoropolymers are disclosed exhibiting good chemical reactivity high breakdown electric field (E>100 MV/m) and high dielectric constants (i.e., ?>10). The polymers can be prepared by functional initiators and from a variety of fluoromonomers including vinylidene difluoride together with one or more additional monomers. The polymers can be combined with other dielectric materials to form composites having uniform composition and morphology.
    Type: Application
    Filed: October 3, 2006
    Publication date: April 3, 2008
    Inventors: Tze-Chiang Chung, Zhicheng Zhang, Shangtao Chen, Katsuyoshi Kubo, Koji Kigawa
  • Patent number: 7220807
    Abstract: Functional fluoro-monomers are polymerized with an organoborane functional initiator in the presence of oxygen to yield functional fluoropolymers and copolymers to produce functional polymers having functional groups at the beginning of the polymer chain.
    Type: Grant
    Filed: June 24, 2005
    Date of Patent: May 22, 2007
    Assignees: Penn State Research Foundation, Daikin Institute of Advanced Chemistry and Technology, Inc.
    Inventors: Tze-Chiang Chung, Han Hong, Masahiko Oka, Katsuyoshi Kubo
  • Patent number: 6911509
    Abstract: 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: Grant
    Filed: February 17, 2004
    Date of Patent: June 28, 2005
    Assignees: The Penn State Research Foundation, Daikin Institute of Advanced Chemistry and Technology, Inc.
    Inventors: Tze-Chiang Chung, Han Hong, Masahiko Oka, Katsuyoshi Kubo
  • 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: 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
  • Patent number: 6699949
    Abstract: 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: Grant
    Filed: May 30, 2002
    Date of Patent: March 2, 2004
    Assignee: Penn State Research Foundation
    Inventor: Tze-Chiang Chung
  • 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
  • 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: 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
  • Patent number: 6355749
    Abstract: 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: Grant
    Filed: December 5, 2000
    Date of Patent: March 12, 2002
    Assignee: The Penn State Research Foundation
    Inventors: Tze-Chiang Chung, Atitsa Petchsuk
  • Patent number: 6117961
    Abstract: The present invention provides a process for producing a crosslinkable styrene or styrene derivative polymer having narrow molecular weight distribution by radical polymerization of a styrene or styrene derivative monomer and other comonomer, wherein the polymerization is conducted in the presence of a catalyst system composed of a free radical compound and a radical polymerization initiator. With the present process, a heat- or photo-crosslinkable styrene or styrene derivative polymer having excellent rheology controlling ability and excellent reaction efficiency of a functional group can be obtained.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: September 12, 2000
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Tetsuo Ogawa
  • Patent number: 6093778
    Abstract: A composition comprises organoborane polyamine complex and polyol. The composition can form a part of a polymerization initiator system that also includes polyisocyanate. The system can be used to initiate polymerization of acrylic monomer and to form a polyurethane/polyurea acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.
    Type: Grant
    Filed: September 8, 1999
    Date of Patent: July 25, 2000
    Assignee: 3M Innovative Properties Company
    Inventor: Alphonsus V. Pocius
  • Patent number: 6008308
    Abstract: A composition comprises organoborane polyamine complex and polyol. The composition can form a part of a polymerization initiator system that also includes polyisocyanate. The system can be used to initiate polymerization of acrylic monomer and to form a polyurethane/polyurea acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: December 28, 1999
    Assignee: 3M Innovative Properties Company
    Inventor: Alphonsus V. Pocius
  • Patent number: 5994484
    Abstract: A composition comprises organoborane polyamine complex and polyol. The composition can form a part of a polymerization initiator system that also includes polyisocyanate. The system can be used to initiate polymerization of acrylic monomer and to form a polyurethane/polyurea acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: November 30, 1999
    Assignee: 3M Innovative Properties Company
    Inventor: Alphonsus V. Pocius
  • Patent number: 5686544
    Abstract: A composition comprises organoborane polyamine complex and polyol. The composition can form a part of a polymerization initiator system that also includes polyisocyanate. The system can be used to initiate polymerization of acrylic monomer and to form a polyurethane/polyurea acrylic adhesive that has exceptionally good adhesion to low surface energy polymers.
    Type: Grant
    Filed: August 11, 1995
    Date of Patent: November 11, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Alphonsus V. Pocius
  • Patent number: 5376746
    Abstract: A two-part initiator system useful in acrylic adhesive compositions comprising in one part a stable organoboron amine complex and in the second part an aldehyde destabilizer or activator. This initiator is particularly useful in elastomeric acrylic adhesive compositions and provides room temperature, relatively slow curing systems with good adhesive properties making them useful in applications where longer open times are required.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: December 27, 1994
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Martin M. Skoultchi
  • Patent number: 5286821
    Abstract: A two-part initiator system useful in acrylic adhesive compositions comprising in one part a stable organoboron amine complex and in the second part an aldehyde destabilizer or activator. This initiator is particularly useful in elastomeric acrylic adhesive compositions and provides room temperature, relatively slow curing systems with good adhesive properties making them useful in applications where longer open times are required.
    Type: Grant
    Filed: March 17, 1992
    Date of Patent: February 15, 1994
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Martin M. Skoultchi
  • Patent number: 5153283
    Abstract: An improved process for producing a vinyl or vinylidene polymer comprising polymerizing a monomer having a vinyl or vinylidene group in the presence of(a) a radical polymerization initiator,(b) an organic phosphorous compound of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen atom, chlorine atom, bromine atom, an alkyl, an aralkyl, or an aryl,(c) an amine hydrohalide or a quaternary ammonium halide, and(d) a copper-containing compound, which can be carried out rapidly and can give the vinyl or vinylidene polymer having excellent mechanical strength without coloring.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: October 6, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Takanori Fujita, Masashi Mori
  • Patent number: 4921921
    Abstract: Hotmelt adhesives which, after heating, are capable of polymerization under the effect of atmospheric oxygen and which essentially consist of a solid reactive component containing at least one polymerizable ethylenic C.dbd.C double bond and a polymerization-initiating organoboron compound and, if desired, other standard auxiliaries.
    Type: Grant
    Filed: May 23, 1986
    Date of Patent: May 1, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Wolfgang Ritter
  • Patent number: 4920188
    Abstract: A curable composition is provided, comprising a monofunctional (meth)arcylate monomer, a poly functional (meth)acrylate monomer, a (meth)acrylate monomer containing an acidic group and at least one (meth)acryloyloxyl group in its molecule, a monofunctional (meth)acrylamide monomer, and a trialkylboron and/or a partial oxide thereof. The composition has improved low-temperature curability at approximately room temperature and water-resistant adherence, and excellent adhesiveness to tooth substances including enamel and dentin and dental alloys, and gives no adverse influence of stimulation to dental pulp. Most preferably, the composition is used as a bonding agent for dental composite resins.
    Type: Grant
    Filed: March 3, 1989
    Date of Patent: April 24, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Takeshi Sakashita, Narimichi Honda, Masami Arata
  • Patent number: 4639498
    Abstract: The aerobically hardenable compositions which comprise polymerizable systems containing components having some degree of ethylenic unsaturation and an oxygen-stable polymerization initiator of at least one organo-boron compound containing at least a major portion of boron to carbon bonds and possibly some boron to hydrogen bonds in the molecule and the boron containing radials are bound to an organic polymer matrix which is oxygen stable, the compositions being useful as casting resins, fillers and adhesives.
    Type: Grant
    Filed: May 29, 1985
    Date of Patent: January 27, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Wolfgang Ritter
  • Patent number: 4167616
    Abstract: Polymerizable monomers are polymerized in a reaction mixture containing as catalysts (A) an oxygen source and (B) an organic boron compound which is soluble in the reaction mixture, the boron compound being (1) a diborane adduct wherein the boron atoms are linked by a hydrocarbyl group having an aliphatic carbon atom bonded to at least one of the boron atoms, or (2) oligomers based on repeating units containing at least two boron atoms linked by hydrocarbyl groups having an aliphatic carbon atom bonded to at least one of the boron atoms. The diborane adducts include the adduct of borane or a dialkylborane and 1,3-butadiene. The oligomers include polymers of diborane/propadiene adducts. The organoboron catalysts provide rapid initiation of polymerization and the polymerization is relatively insensitive to oxygen concentration, thereby permitting polymerization at ambient temperatures.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: September 11, 1979
    Assignee: Rohm and Haas Company
    Inventor: Joseph M. Bollinger
  • Patent number: 4121032
    Abstract: An alternating copolymer of an olefinic unsaturated compound and a conjugated vinyl compound is produced by contacting said monomers with at least one organoboron halide or/and a mixture of at least one organo-compound of metal from Groups IIb, IIIb and IVb of the Mendeleev Periodic Table and at least one halogeno-compound of metal from Groups IIIb and IVb of the Mendeleev Periodic Table. A typical catalyst is ethylboron dichloride or a combination of triethylaluminum and tin tetrachloride.
    Type: Grant
    Filed: April 15, 1975
    Date of Patent: October 17, 1978
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kohei Nakaguchi, Shohachi Kawasumi, Masaaki Hirooka, Hiroshi Yabuuchi, Hiroyoshi Takao
  • Patent number: 3989882
    Abstract: An alternating copolymer of an olefinic unsaturated compound and a conjugated vinyl compound is produced by contacting said monomers with at least one organoboron halide or/and a mixture of at least one organo-compound of metal from Groups IIb, IIIb and IVb of the Mendeleev Periodic Table and at least one halogeno-compound of metal from Groups IIIb and IVb of the Mendeleev Periodic Table. A typical catalyst is ethylboron dichloride or a combination of triethylaluminum and tin tetrachloride.
    Type: Grant
    Filed: January 9, 1975
    Date of Patent: November 2, 1976
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kohei Nakaguchi, Shohachi Kawasumi, Masaaki Hirooka, Hiroshi Yabuuchi, Hiroyoshi Takao