Contains Boron Or Silicon Atom Patents (Class 526/178)
  • Patent number: 6284905
    Abstract: A Group 4 transition metal complex containing a boron or aluminum bridging group containing a nitrogen containing electron donating group, especially an amido group.
    Type: Grant
    Filed: March 10, 2000
    Date of Patent: September 4, 2001
    Assignees: The Dow Chemical Company, The Regents of the University of Michigan
    Inventors: Arthur J. Ashe, III, David D. Devore, Xinggao Fang, Kevin A. Frazier, D. Patrick Green, Jasson T. Patton, Francis J. Timmers
  • Publication number: 20010018397
    Abstract: The present invention relates to an initiation system composed of the reaction product of at least one cyclic siloxane and at least one organometalic compound of sufficient reactivity to open the siloxane ring.
    Type: Application
    Filed: April 10, 1998
    Publication date: August 30, 2001
    Inventors: THOMAS ZUNDEL, PHILIPPE TEYSSIE, ROBERT JEROME, CHRISTOPHE NAVARRO
  • Patent number: 6221991
    Abstract: Polar polymers having the following formula: FG-(Q)d-Rn-Z-J-[A(R1R2R3)]x   (I) wherein FG is H or a protected or non-protected functional group; Q is a polar hydrocarbyl group derived by incorporation of a polar compound selected from group consisting of esters, amides, and nitrites of acrylic and methacrylic acid, and mixtures thereof; d is an integer from 10 to 2000; R is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof; n is an integer from 0 to 5; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; J is oxygen, sulfur, or nitrogen; [A(R1R2R3)]x is a protecting group, in which A is an element selected from Group IVa of the Periodic Table of Elements; R1, R2, and R3 are each independently selected from the group consisting
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: April 24, 2001
    Assignee: FMC Corporation
    Inventors: Robert J. Letchford, James A. Schwindeman, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6162853
    Abstract: Described is a process for preparing a molding suitable for optical purposes, which process comprises the conjoint free-radical polymerization of a precondensate (A) which is derived from at least one hydrolytically condensable silane (a) having at least one free-radically polymerizable group X, and of a monomer (B) having at least two free-radically polymerizable groups Y, the numerical ratio of groups X to groups Y being not greater than 5:1. The moldings obtainable by this process are characterized by high transparency and homogeneity, freedom from stress, scratch and abrasion resistance, high mechanical strength, etc.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: December 19, 2000
    Assignee: Institut fuer Neue Materialien Gemeinnuetzige GmbH
    Inventors: Bert Braune, Elisabeth Geiter, Herbert Krug, Peter Mueller, Helmut Schmidt
  • Patent number: 6160054
    Abstract: Hetero-telechelic polymers having the formula:FG--(Q).sub.d --Z--J--[A(R.sup.1 R.sup.2 R.sup.3)].sub.x (I)wherein FG is a protected or non-protected functional group; Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof; d is an integer from 10 to 200; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; J is oxygen, sulfur, or nitrogen; [A(R.sup.1 R.sup.2 R.sup.3)].sub.x is a protecting group, wherein A is an element selected from Group IVa of the Periodic Table of Elements; R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: December 12, 2000
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6153706
    Abstract: This invention provides novel protected, multi-functionalized multi-arm polymers, their optionally hydrogenated analogues and optionally deprotected analogues thereof, and processes for making these compounds. In the invention, monomers are polymerized using a protected functionalized initiator to form living polymer anions, the living anions coupled to form multi-arm polymers, additional monomer added to form additional polymer arms, and the multi-arm polymer functionalized using electrophiles.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: November 28, 2000
    Assignee: FMC Corporation
    Inventors: Robert James Letchford, James Anthony Schwindeman
  • Patent number: 6150487
    Abstract: This invention relates to a multifunctional organic alkali metal initiator for the preparation of various kinds of star polymers by anionic polymerization, a process for making the initiator, a process using said initiator for making star polymers and the polymers obtained. The initiator can be represented by the formula: M.sub.a (RMe).sub.b, wherein M is selected from Sn, Ti, Al, Si and/or B; R is a hydrocarbyl group containing 8-100 carbon atoms, a=1-3, b=2.5-6.5, Me is an alkali metal which may be selected from Na and Li. The initiator was synthesized by reacting an organic alkali metal with a conjugated diene and/or a mono-olefin monomer, and then adding hetero-atom containing halide. The star polymer obtained has a radial molecular structure consisting of several macromolecular chain arms radiating from the initiator core, and its molecular weight distribution expressed by GPC presents a uniform singlet.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: November 21, 2000
    Assignee: China Petrochemical Corporation
    Inventors: Xingying Zhang, Guantai Jin, Suhe Zhao
  • Patent number: 6103846
    Abstract: The preparation of di- or polyfunctional polymers by anionic polymerization using functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--A--B, wherein each R is methyl and A is a hydrocarbon bridging group containing from 1 to 25 carbon atoms, and B is an alkali metal, is improved when polymerization occurs in the presence of a polymerization termination inhibitor which is a metal alkyl which has been added at a concentration to afford a molar ratio of the termination inhibitor to living polymer chain ends of about 0.1:1 to about 10:1.
    Type: Grant
    Filed: May 5, 1999
    Date of Patent: August 15, 2000
    Assignee: Shell Oil Company
    Inventors: Carl Lesley Willis, Robert Charles Bening, Michael Wayne Potter, Grant Wesley Haddix, David Karl Schisla, Thomas Carl Semple, Daniel Earl Goodwin
  • Patent number: 5900464
    Abstract: Polar polymers having the following formula:FG--(Q).sub.d --R.sub.n --Z--J--?A(R.sup.1 R.sup.2 R.sup.3)!.sub.x(I)wherein FG is H or a protected or non-protected functional group; Q is a polar hydrocarbyl group derived by incorporation of a polar compound selected from group consisting of esters, amides, and nitriles of acrylic and methacrylic acid, and mixtures thereof; d is an integer from 10 to 2000; R is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof; n is an integer from 0 to 5; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; J is oxygen, sulfur, or nitrogen; ?A(R.sup.1 R.sup.2 R.sup.3)!.sub.x is a protecting group, in which A is an element selected from Group IVa of the Periodic Table of Elements; R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: May 4, 1999
    Assignee: FMC Corporation
    Inventors: Robert J. Letchford, James A. Schwindeman, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 5849847
    Abstract: Polyalkenylaromatic-polyethylene copolymers are prepared using protected functional organolithium initiators. Polymerization of an alkenylsubstituted aromatic monomer followed by ethylene, results in a protected functional block polystyrene-co-polyethylenyllithium. Termination with a functionalizing agent followed by deprotection produces polymeric products with high functionalization at the initiating chain-end and at least partial functionalization at the terminal chain-end.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: December 15, 1998
    Assignee: FMC Corporation
    Inventor: Roderic P. Quirk
  • Patent number: 5780551
    Abstract: This invention concerns novel, unsymmetrically protected, telechelically functionalized linear and star or multi-arm polymers, their optionally hydrogenated analogues, the polymers produced by selective removal of the protecting groups, the segmented block polymers produced by further reaction of these selectively deprotected polymers with selected comonomers, and the processes to prepare these polymers.
    Type: Grant
    Filed: June 3, 1996
    Date of Patent: July 14, 1998
    Assignee: FMC Corporation
    Inventors: John F. Engel, James A. Schwindeman, Roderic P. Quirk, Conrad W. Kamienski
  • Patent number: 5741869
    Abstract: Addition polymers derived from norbornene-functional monomers are terminated with an olefinic moiety derived from a chain transfer agent selected from a compound having a terminal olefinic double bond between adjacent carbon atoms, excluding styrenes, vinyl ethers, and conjugated dienes and at least one of said carbon atoms has two hydrogen atoms attached thereto. The addition polymers of this invention are prepared from a single or multicomponent catalyst system including a Group VIII metal ion source. The catalyst systems are unique in that they catalyze the insertion of the chain transfer agent exclusively at a terminal end of the polymer chain.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 21, 1998
    Assignee: The B.F. Goodrich Company
    Inventors: Brian Leslie Goodall, George Martin Benedikt, Lester Howard McIntosh, III, Dennis Allen Barnes, Larry Funderburk Rhodes
  • Patent number: 5728782
    Abstract: There is provided a process comprising polymerizing a compound selected from the group consisting of a conjugated diene, a vinyl-substituted aromatic compound, and mixtures thereof in a gas phase fluidized polymerization vessel under polymerization conditions in the presence of at least one anionic initiator, optionally in the presence of an inert particulate material. A novel resin particle produced by the process is also provided.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: March 17, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Monika Brady, Kevin Joseph Cann, David Joseph Dovedytis
  • Patent number: 5717043
    Abstract: In a polymerization process of at least one of monomers selected from the group consisting of conjugated diene compounds such as butadiene and vinylaromatic compounds such as styrene, an organolithium compound such as butyllithium is added to the polymerization system first in the presence of the monomer, and thereafter a secondary amine compound such as saturated cyclic imine is added thereto to produce a soluble initiator by bringing the both compound into contact with each other. Polymerization is carried out with the soluble initiator formed. The obtained high molecular weight polymer is modified with a coupling agent such as tin tetrachloride. The polymer obtained has a high molecular weight, a narrow molecular weight distribution, and controlled molecular weight, and exhibits remarkable coupling property, low hysteresis loss. The process provides a polymer having a consistent characteristic, regardless of production scale and procedures of adding materials.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: February 10, 1998
    Assignee: Bridgestone Corporation
    Inventors: Atushi Nakayama, Koichi Morita, Masaaki Izuchi
  • Patent number: 5708092
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from carbon and silicon; R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: January 13, 1998
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
  • Patent number: 5700887
    Abstract: A process for producing a branched polymer from a vinyl aromatic monomer comprising:A) contacting a vinyl aromatic monomer with a difunctional anionic initiator under conditions such that a dianion macromer is formed,B) contacting the dianion macromer with a multifunctional coupling agent having at least 3 reactive sites under polymerization conditions such that branches form during polymerization, andC) contacting the product of step B with a terminating agent under conditions such that the reactive sites are terminated.
    Type: Grant
    Filed: February 2, 1996
    Date of Patent: December 23, 1997
    Assignee: The Dow Chemical Company
    Inventors: Jerry L. Hahnfeld, Timothy G. Bee, Donald E. Kirkpatrick, Lu Ho Tung, William C. Pike
  • Patent number: 5700888
    Abstract: The present invention provides a method of anionic synthesis of stable macrocyclic polymers that are compounded to form vulcanizable elastomeric compounds exhibiting reduced hysteresis properties. Cyclic organometallic compounds containing divalent metal atoms of Groups IIA and IIB of the Periodic System are employed as initiators of anionic polymerization of conjugated diene, vinyl aromatic and/or triene monomers. Coupling of the living ends of the resulting macrocyclic polymers or copolymers with a coupling agent or a coupling agent that is also a functionalizing agent results in stable macrocyclic polymers with improved hysteresis properties.
    Type: Grant
    Filed: November 10, 1996
    Date of Patent: December 23, 1997
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 5665829
    Abstract: Siloxy-terminated hydrocarbon polymers containing at least one polymer chain per molecule of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from saturated and unsaturated aliphatic and aromatic radicals, A is a saturated hydrocarbon bridging group optionally containing at least one aromatic group and --(M)n -- represents a polymer of an olefinic monomer, n having a value such that the average molecular weight of the polymeric chain is from about 1000 to about 5,000,000, together with telechelic polymers and radial polymers containing this unit.
    Type: Grant
    Filed: April 12, 1995
    Date of Patent: September 9, 1997
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Gt. Britain & Northern Ireland
    Inventors: Neil Shepherd, Malcolm John Stewart
  • Patent number: 5663250
    Abstract: Protected functional initiator initiated elastomer solutions are deprotected and optionally ionic impurities removed by contact with a molten component such as sodium bisulphate monohydrate. This allows deprotection and removal of metal contaminants such as the initiator or residue from hydrogenation catalysts without the introduction of significant amounts of additional water which cause emulsion formation. In accordance with this invention, better metal removal is achieved and the process of metal removal operates more smoothly because of the absence of emulsion formation. Separation of the molten component containing the extracted metal contaminants can easily be carried out by simple liquid-liquid phase separation on either a continuous or batch basis.
    Type: Grant
    Filed: May 16, 1996
    Date of Patent: September 2, 1997
    Assignee: Shell Oil Company
    Inventors: Michael Wayne Potter, William Charles Malven, Cary Alan Veith
  • Patent number: 5654371
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3) (II)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is defined as a branched or straight chain hydrocarbon tether or connecting group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from Group IVa of the periodic table and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, aryl or substituted aryl groups, and n is an integer from 1 to 5.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 5, 1997
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
  • Patent number: 5612435
    Abstract: The anionic polymerization of unsaturated monomers with functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li is improved by selecting A' from the structures --CH.sub.2 --CH.sub.2 --CH.sub.2 -- (1,3-propyl), --CH.sub.2 --CH(CH.sub.3)--CH.sub.2 -- (2-methyl-1,3-propyl), --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --(2,2-dimethyl-1,3-propyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,8-octyl). This narrow class of polymerization initiators operate at surprisingly higher polymerization temperatures with surprisingly lower amounts of dead initiator than similar initiators wherein A' is --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,4-butyl), --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,5-pentyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,6-hexyl).
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: March 18, 1997
    Assignee: Shell Oil Company
    Inventors: Robert C. Bening, Carl L. Willis
  • Patent number: 5605991
    Abstract: A multifunctional initiator is prepared by contacting an organo-alkali metal compound with a silane represented by the formula: ##STR1## wherein the R' are generally lower alkyl groups such as methyl and the R" is generally an .paren open-st.CH.sub.2 .paren close-st..sub.n group with n=2. Superior results are obtained presumably because of the separation of the vinyl groups and the greater solubility of the compound because of the R' groups. The resulting catalyst initiates polymerization of monomers such as conjugated dienes and monovinyl substituted aromatic compounds to give relatively monodispersed polymers with little or no crosslinking.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: February 25, 1997
    Assignee: Shell Oil Company
    Inventors: Linda R. Chamberlain, Ronald J. Hoxmeier, Philip A. DeFriend
  • Patent number: 5571881
    Abstract: Addition polymers derived from norbornene-functional monomers are terminated with an olefinic moiety derived from a chain transfer agent selected from a compound having a terminal olefinic double bond between adjacent carbon atoms, excluding styrenes, vinyl ethers, and conjugated dienes and at least one of said carbon atoms has two hydrogen atoms attached thereto. The addition polymers of this invention are prepared from a single or multicomponent catalyst system including a Group VIII metal ion source. The catalyst systems are unique in that they catalyze the insertion of the chain transfer agent exclusively at a terminal end of the polymer chain.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 5, 1996
    Assignee: The B. F. Goodrich Company
    Inventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes, Larry F. Rhodes
  • Patent number: 5569730
    Abstract: Addition polymers derived from norbornene-functional monomers are terminated with an olefinic moiety derived from a chain transfer agent selected from a compound having a terminal olefinic double bond between adjacent carbon atoms, excluding styrenes, vinyl ethers, and conjugated dienes and at least one of said carbon atoms has two hydrogen atoms attached thereto. The addition polymers of this invention are prepared from a single or multicomponent catalyst system including a Group VIII metal ion source. The catalyst systems are unique in that they catalyze the insertion of the chain transfer agent exclusively at a terminal end of the polymer chain.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: October 29, 1996
    Assignee: The B. F. Goodrich Company
    Inventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes, Larry F. Rhodes
  • Patent number: 5565526
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3) (II)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is defined as a branched or straight chain hydrocarbon tether or connecting group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from Group IVa of the periodic table and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, aryl or substituted aryl groups, and n is an integer from 1 to 5.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: October 15, 1996
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
  • Patent number: 5468819
    Abstract: A single component ionic catalyst consists essentially of an organonickel complex cation, and a weakly coordinating neutral counteranion. The cation is a neutral bidentate ligand removably attached to a Group VIII transition metal in an organometal complex. The ligand is easily displaced by a norbornene-type (NB-type) monomer in an insertion reaction which results in an unexpectedly facile addition polymerization. A NB-type monomer includes NB or substituted NB, or a multi-ringed cycloolefin having more than three rings in which one or more of the rings has a structure derived from NB, and a ring may have an alicyclic alkyl, alkylene or alkylidene substituent. The insertion reaction results in the formation of a unique propagating species more soluble in a polar than in a non-polar solvent and devoid of an available .beta.-hydrogen for termination. The ensuing propagation of a polymer chain proceeds without measurable unsaturation.
    Type: Grant
    Filed: November 16, 1993
    Date of Patent: November 21, 1995
    Assignee: The B.F. Goodrich Company
    Inventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes
  • Patent number: 5416168
    Abstract: The anionic polymerization of unsaturated monomers with functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li is improved when each R is methyl and A' is --CH.sub.2 --C.sub.6 H.sub.10 --CH.sub.2 -- or --CH.sub.2 --CR'R"--CH.sub.2 -- wherein R' is a linear alkyl having from 1 to 10 carbon atoms and R" is hydrogen or a linear alkyl having from 1 to 10 carbon atoms. This initiator provides process and product advantages over all other known initiators of the same type.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: May 16, 1995
    Assignee: Shell Oil Company
    Inventors: Carl L. Willis, Robert C. Bening
  • Patent number: 5391663
    Abstract: The anionic polymerization of unsaturated monomers with functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li is improved by selecting A' from the structures --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,3-propyl), --CH.sub.2 --CH(CH.sub.3)--CH.sub.2 --(2-methyl-1,3-propyl), --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --(2,2-dimethyl-1,3-propyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,8-octyl). This narrow class of polymerization initiators operate at surprisingly higher polymerization temperatures with surprisingly lower amounts of dead initiator than similar initiators wherein A' is --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,4-butyl), --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --(1,5-pentyl), or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 13 CH.sub.2 --(1,6-hexyl).
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: February 21, 1995
    Assignee: Shell Oil Company
    Inventors: Robert C. Bening, Carl L. Willis
  • Patent number: 5376745
    Abstract: The anionic polymerization of isoprene with monolithium initiators and functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--O--A'--Li wherein R.sup.1, R.sup.2, and R.sup.3 are preferably alkyl, alkoxy, aryl, or alkaryl groups having from 1 to 10 carbon atoms, and A' is preferably a branched or straight chain bridging group having at least 2 carbon atoms produces unsaturated and hydrogenated isoprene polymers having high 1,4-addition of the isoprene, from about one to two terminal functional groups per molecule, and low viscosity.
    Type: Grant
    Filed: December 1, 1993
    Date of Patent: December 27, 1994
    Assignee: Shell Oil Company
    Inventors: Dale L. Handlin, Jr., Robert C. Bening, Carl L. Willis
  • Patent number: 5373073
    Abstract: A process for the preparation of 1-monoalkyl(C.sub.1 -C.sub.4) dimethylsilyl-1-propyne polymers which comprises polymerizing a 1-monoalkyl (C.sub.1 -C.sub.4)dimethylsilyl-1-propyne monomer in the presence of a compound of a transition metal and a member selected from .alpha.,.omega.-dihydropolydialkylsiloxanes and polyalkylhydrosiloxanes in a solvent inert to the polymerization. The polymerization reaction proceeds at low temperatures in an efficient manner. Membranes of the resultant polymer have a high gas transmission and suffer but little degradation when placed under severe temperature conditions.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: December 13, 1994
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yukihiro Saito, Katsunori Waragai, Shiro Asakawa
  • Patent number: 5331058
    Abstract: Process for anionically polymerising a conjugated 1,3-diene monomer consists of contacting the monomer in an inert hydrocarbon solvent with a monofunctional silyl ether initiator of general formula R.sup.1 R.sup.2 R.sup.3 Si--O--A--Li where R.sup.1 to R.sup.3 are independently selected from monovalent organic substituent groups and A is a short chain hydrocarbon bridging group, to yield a polydiene having a molecular weight of typically 1,000-10,000, a high 1.4 content of typically 90% and a low polydispensity of typically 1.15. The reactive ends of the living polymer chains may be terminated with a reactive group such as hydroxyl by treating the polymer with ethylene oxide. Subsequent removal of the polymer's relatively unreactive silyl end groups by reaction with tetra-n-butylammonium fluoride produces a difunctional, chain-extendable, hydroxy-terminated polydiene useful as a rubbery binder prepolymer.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: July 19, 1994
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Neil Shepherd, Malcolm J. Stewart
  • Patent number: 5328936
    Abstract: A process for making porous polymeric particles having high surface area includes suspending a discontinuous organic phase in an continuous aqueous phase, wherein the organic phase includes an ethylenically unsaturated monomer, a water soluble phase extender and a surfactant in an amount effective to solubilize the water soluble phase extender in the monomer and wherein the aqueous phase includes a diffusion barrier agent for limiting mass transfer of the phase extender from the organic phase to the aqueous phase, and then polymerizing the ethylenically unsaturated monomer to form the porous polymeric particles.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: July 12, 1994
    Assignee: Rohm and Haas Company
    Inventors: Paul J. Leifholtz, Thomas E. Meteyer
  • Patent number: 5317058
    Abstract: A microwave-absorbing material composed of blends of polar icosahedral molecular units with a variety of host matrices, or with polymers with the units covalently bonded in a pendant manner to the polymer chain. Both blends and polymers must impart a high degree of orientational mobility to the units so that they can absorb microwave radiation. These materials employ orientationally mobile, polar icosahedral molecular units as the source of dielectric loss at microwave frequencies. Examples of these units are the polar carboranes (ortho- and meta-carborane), polar carboranes with electronegative and/or electropositive substitutes, and polar "buckminsterfullerenes.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: May 31, 1994
    Assignee: Hughes Aircraft Company
    Inventors: Thomas K. Dougherty, Norman H. Harris, James R. Chow, Brian M. Pierce, David A. Whelan
  • Patent number: 5270396
    Abstract: A method for preparing resinous copolymers by sequential charge copolymerization of at least two charges, at least one being a conjugated diene and at least one being a monovinylarene; followed by a charge of a polyfunctional coupling agent; and the final charge being an essentially difunctional coupling agent. The copolymer made by this method and articles made from this copolymer are also provided.
    Type: Grant
    Filed: May 18, 1992
    Date of Patent: December 14, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Ralph C. Farrar, Jr., George A. Moczygemba, William J. Trepka
  • Patent number: 5268436
    Abstract: The invention relates to moldable, radically polymerizable multicomponent mixtures containingethylenically unsaturated, polymerizable compounds, if desired in admixture with soluble and/or insoluble fillers andan activator system initiatable by contact with oxygen,and is characterized in that these multicomponent mixtures contain an activator system based on the following principal components which can be initiated by contact with oxygen and water and, in particular, by contact with ambient air:N-alkyl-substituted tert-arylamines containing at least one aliphatic CH bond in the .alpha.-positionmetal compounds at least partly soluble in the system to accelerate the drying of unsaturated oils andcompounds of weakly acidic carboxylic acids having pK.sub.a values of no less than about 0.9 which can be hydrolyzed to the free carboxylic acid on contact with moisture.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: December 7, 1993
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Thomas Huver, Herbert Fischer, Winfried Emmerling
  • Patent number: 5266667
    Abstract: This system for priming the animic polymerization of (meth)acrylates includes at least one primer of the formula R--M (I) in which M represents a metal selected from alkaline and alkaline earth metals and R represents an alkyl radical with a straight or branched chain containing 2 to 6 atoms of carbon or an aryl radical or an arylalkyl radical. H is characterized in that it further contains at least one organic derivative of an alkaline metal, with the proviso that said organic derivative is neither an alcoholate nor a carboxyl acid ester substituted in position .alpha. by said metal. Applications in the anionic polymerization of (meth)acrylates.
    Type: Grant
    Filed: November 29, 1991
    Date of Patent: November 30, 1993
    Assignee: Elf Atochem S.A.
    Inventors: Philippe Teyssie, Roger Fayt, Sunil K. Varshney
  • Patent number: 5180799
    Abstract: A process for addition polymerization of vinylic (in particular methacrylic) monomers at a temperature in the range of -20.degree. to 60.degree. c., in the presence of a catalyst comprising:(a) a first component of empirical formula (I):MT (I)whereinM is an alkali metal atom; andT is bulky hydrocarbyl which contains at least 4 carbon atoms and is optionally substituted by one or more pendent substituents, or hetero-substituted hydrocarbyl, each of which is inert in the process conditions; and(b) a (co-catalyst) second component comprising a compound of empirical formula (II):Q(X.sub.m) (Y.sub.n) Zp (II)whereinQ is Al, B or Zn;m, n and p are each 0 or an integer such that (m+n+p)=2 or 3 (depending on the appropriate valency of Q; andX, Y and Z are each independently optionally substituted bulky hydrocarbyl, orX and Y together are optionally substituted hydrocarbadiyl, and Z is optionally substituted bulky hydrocarbyl,all of which groups are inert in the process conditions.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: January 19, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Denis G. H. Ballard, David M. Haddleton, David L. Twose
  • Patent number: 5149751
    Abstract: A process for the preparation of 1-monoalkyl (C.sub.1 -C.sub.4)dimethylsilyl-1-propyne polymers which comprises polymerizing a 1-monoalkyl (C.sub.1 -C.sub.4)dimethylsilyl-1-propyne monomer in the presence of a compound of a transition metal and a member selected from .alpha.,.omega.-dihydropolydialkylsiloxanes and polyalkyldihydrosiloxanes in a solvent inert for the polymerization. The polymerization reaction proceeds at low temperatures in an efficient manner. The membrane of the resultant polymer has a high gas transmission and suffers little degradation when placed under severe temperature conditions.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: September 22, 1992
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yukihiro Saito, Katsunori Waragai, Shiro Asakawa
  • Patent number: 5063190
    Abstract: Liquid telechelic polymers are made from dienes and are produced via anionic polymerization. While having low molecular weight, for example less than 15,000, the telechelic polymers are generally gel-free, have high amounts of trans-1,4 structure, low vinyl unsaturation and low bulk viscosities. The liquid telechelic polymers are made utilizing a trimetallic initiator comprised of (1) an organopolylithium compound and (2) a complex of a trialiphatic substituted aluminum compound or derivative thereof and a barium salt of an organic alcohol.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: November 5, 1991
    Assignee: GenCorp Inc.
    Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
  • Patent number: 4889900
    Abstract: A process is disclosed for treatment of alkyl methacrylate monomers for subsequent polymerization by an anionic initiator to produce a polymer with a molecular weight distribution between about 1.20 and about 1.01. The process involves treatment of the monomer with an aluminum hydrocarbyl or boron hydrocarbyl in quantities which permit polymerization in the presence of the by-products of the reaction between the impurities and the aluminum hydrocarbyl or boron hydrocarbyl.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: December 26, 1989
    Assignee: Shell Oil Company
    Inventor: Donn A. DuBois
  • Patent number: 4843120
    Abstract: It has been determined that certain rubbery polymers having multiple glass transition temperatures can be utilized in making tires which have improved rolling resistance, improved wet skid resistance, and outstanding tread wear. These rubbery polymers are derived from at least one conjugated diolefin monomer, have a first glass transition temperature which is between -110.degree. C. and -20.degree. C. and have a second glass transition temperature which is between -50.degree. C. and 0.degree. C. These rubber polymers can be homopolymers of conjugated diolefin monomers, copolymers of more than one conjugated diolefin monomer, or copolymers derived from at least one conjugated diolefin monomer and at least one vinyl aromatic monomer.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: June 27, 1989
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, Bill B. Gross, Joel L. Cox, George F. Balogh
  • Patent number: 4638092
    Abstract: The invention concerns new organo-boron compounds with strong aerobic initiator action to start polymerizations but with improved stability when in contact with atmospheric oxygen. The boron is connected to the molecule predominantly by boron to carbon and optionally boron to hydrogen bonds. The organo-boron compounds are characterized by the fact that the boron containing radicals are connected to an organic polymer matrix that is at least largely nonreactive when exposed to atmospheric oxygen. The boron containing radicals are preferably directly connected to a carbon atom of the polymer matrix by at least one valence of the respective boron atom. The advantageously viscous-fluid to solid masses that are preferably largely free of solvents contain especially hydro-boron radicals and/or organic boron radicals that can have alkyl, cycloalkyl and/or aryl radicals as substituents.
    Type: Grant
    Filed: May 29, 1985
    Date of Patent: January 20, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Wolfgang Ritter
  • Patent number: 4518753
    Abstract: A process for the anionic polymerization of a conjugated 1,3-diene in a polar solvent consists of contacting the 1,3-diene with an organo alkali or alkaline earth metal initiator and a sterically hindered Lewis acid, allowing the 1,3-diene to polymerize in the polar solvent and terminating the polymerization reaction. Preferably the Lewis acid is a substituted triaryl derivative of a Group III element, especially boron. However in certain cases (e.g. where the aryl derivative itself is large) the Lewis acid may be an unsubstituted triaryl derivative of a Group III element. Suitable Lewis acids include trimesityl boron and tri (2,6-dimethylphenyl) boron. In preferred embodiments of the present process the 1,3-diene is butadiene, the polar solvent is tetrahydrofuran and the initiator is a difunctional initiator, especially an electron transfer reagent.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: May 21, 1985
    Assignee: National Research Development Corporation
    Inventors: David H. Richards, Malcolm J. Stewart
  • Patent number: 4311803
    Abstract: A continuous solution polymerization process for polymerizing conjugated dienes alone or with a copolymerizable monovinylarene in the presence of a gel inhibitor employing a first stirred reactor in series with a following plug-flow tube reactor.
    Type: Grant
    Filed: August 26, 1980
    Date of Patent: January 19, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Richard L. Smith, Ralph C. Farrar, Richard J. Sonnenfeld
  • Patent number: 4254247
    Abstract: An initiator for the anionic polymerization of vinyl monomers and dienic monomers comprises the product from the association of an alkali metal amide and the salt from at least one hydroxylated compound with the same alkali metal in an aprotic solvent. The hydroxylated compound is a primary, secondary, or tertiary alcohol. The hydroxylated compound may be a member selected from the group consisting of an alcohol substituted by an heterocyclic group, alcohols containing ethylenic unsaturation, alcohols substituted by an aromatic group, alicyclic alcohols, aromatic alcohols, polyhydroxy compounds, ether-alcohols, polyether-alcohols, and enols from ketones and amino acids.
    Type: Grant
    Filed: May 24, 1977
    Date of Patent: March 3, 1981
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Sylvie L. Boileau, Paul J. Caubere, Serge L. Lecolier, Serge F. Raynal
  • Patent number: 4243787
    Abstract: The invention relates to a process for the anionic polymerization and copolymerization of vinyl, dienic and heterocyclic monomers.According to the invention, the process consists in carrying out the reaction in the presence of an initiator consisting of a molecular combination of an alkali metal amide and the salt of the same alkali metal with at least one hydroxylic compound and in the absence of solvent. The initiator can be prepared by intimately mixing its constituents or in the presence of a solvent of low polarity which is subsequently evaporated off, or in situ in the monomer.Application to the synthesis of special or widely used polymers and copolymers.
    Type: Grant
    Filed: November 6, 1978
    Date of Patent: January 6, 1981
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Sylvie L. Boileau, Paul J. Caubere, Gilberte Ndebeka, Serge L. Lecolier, Serge F. Raynal
  • Patent number: 4238588
    Abstract: The invention pertains to a method for preparation of polymers, grafted polymers, and copolymers from olefins substituted by polar groups (ester, nitrile, or aryl) or from dienes, wherein the polymerization is initiated by the system formed by mixing of an organic amide of alkaline metal with an alkaline metal alkoxide. The organic amide is derived from primary or secondary amines or polyamines, or from tertiary polyamines containing at least one primary or secondary amino group. These amines contain N-C or N-Si bonds, 1-4000 C atoms and 1-1000 N atoms in a molecula, or have the molecular weight below 100,000. The alkoxides are derived from C.sub.3 -C.sub.16 alcohols. The polymerizations are carried out at -80.degree. to +80.degree. C. (advantageously at +20.degree. C.), at the monomer/organic amide molar ratio 5-1500, at the molar ratio alkoxide/amide 0.5-10, and in hydrocarbon or ether solvents.
    Type: Grant
    Filed: December 19, 1978
    Date of Patent: December 9, 1980
    Assignee: Ceskoslovenska akademie ved
    Inventors: Lubomir Lochman, Jiri Trekoval
  • Patent number: 4152505
    Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with other conjugated dienes or with vinyl aromatic compounds having an elastomeric character are prepared by use of a catalytic system formed of the reaction product of (a) an organometallic compound of a metal of Group IIIA of the Mendeleev periodic table of elements with (b) at least one electron-donor compound containing at least one hetero-atom.
    Type: Grant
    Filed: April 29, 1977
    Date of Patent: May 1, 1979
    Assignee: Compagnie Generale des Etablissements Michelin
    Inventor: Yves de Zarauz
  • Patent number: 4148985
    Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with other conjugated dienes or with vinyl aromatic compounds having an elastomeric character are prepared by use of a catalytic system formed of the reaction product of (a) an organometallic compound of a metal of Group IIIA of the Mendeleev periodic table of elements with (b) at least one electron-donor compound containing at least one hetero-atom.
    Type: Grant
    Filed: April 29, 1977
    Date of Patent: April 10, 1979
    Assignee: Compagnie Generale des Etablissements Michelin
    Inventor: Yves de Zarauz
  • Patent number: 4148986
    Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with other conjugated dienes or with vinyl aromatic compounds having an elastomeric character are prepared by use of a catalytic system formed of the reaction product of (a) an organometallic compound of a metal of Group IIIA of the Mendeleev periodic table of elements with (b) at least one electron-donor compound containing at least one hetero-atom.
    Type: Grant
    Filed: April 29, 1977
    Date of Patent: April 10, 1979
    Assignee: Compagnie Generale des Etablissements Michelin
    Inventor: Yves DeZarauz