Solid Polymer Derived From Reactant Containing A Phenolic Group Patents (Class 525/219)
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Patent number: 6265490Abstract: The invention relates to novolac resins obtained by condensation (A) of an aromatic compound containing at least two hydroxyl groups and (B) of an unconjugated diene in an (A)/(B) molar ratio of between 0.7 and 1.75 in the presence of an acidic catalyst, which are characterized in that the content of free aromatic compound is lower than 5% by weight. Also disclosed are a process for the preparation of the resins, and rubber-based compositions including from 0.5 to 20 parts by weight of the above mentioned novolac resins per 100 parts by weight of rubber. The invention also relates to the use of the resins or rubber-based compositions in the field of vulcanization, especially of tires and of conveyor belts.Type: GrantFiled: March 28, 1997Date of Patent: July 24, 2001Assignee: Ceca, S.A.Inventors: Christophe Morel-Fourrier, Thierry Dreyfus, Messaoud Bekhiekh, Bonnie L. Stuck
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Patent number: 6211328Abstract: The present invention relates to a phenol resin, in particular a phenol resin for resists suitable for forming resist patterns. The phenol resin of the present invention is obtained by reacting at least two components, i.e., a compound (A) such as 4-hydroxymethyl-2,6-dimethylphenol and a polymerizable phenol compound such as parahydroxystyrene or a polymer (B), which is a polymer of the polymerizable phenol compound, in a ratio of 1 to 50 moles of the compound (A) to 100 moles of the polymerizable phenol compound or 100 moles of structural unit of the polymerizable phenol compound contained in the polymer (B) in the presence of an acid and having a molecular weight of 2,000 to 20,000. Such a phenol resin provides good pattern shape, heat resistance, resolution, and sensitivity in resists for lithography.Type: GrantFiled: June 1, 2000Date of Patent: April 3, 2001Assignee: Gun Ei Chemical Industry Co., LTDInventors: Yoshiaki Kurimoto, Katsuhiro Maruyama, Akira Yoshitomo, Satoru Yoshida, Satoru Kitano
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Patent number: 6133403Abstract: Disclosed are acid hardenable phenolic resin compositions and novolac compositions modified with about 5 to about 15% by weight of at least one reactive diluent selected from the group consisting of benzylic alcohol, benzylic ether, ethylene glycol, 1,3-butylene glycol, monoallyl or methylallyl ethers of poly(methylol) alkanes, monoallyl ether of glycerine, allyl or methallyl glycidyl ether, N-acylated arylamine, N-acylated naphthylamine, N-substituted arylsulfonamide, and N-substituted arylamine. The reactive diluent can be used to improve impact resistance and flexibility of the acid hardenable phenolic resin. Preferably, the methods for modifying mix life of acid hardenable phenolic resin by use of aryl phosphite and benzylic alcohol, and methods for modifying novolac resins, as well as methods for making the present compositions and products, such as coiled filament pipe and laminate panels, employing the compositions are also disclosed.Type: GrantFiled: October 7, 1998Date of Patent: October 17, 2000Assignee: Borden Chemical, Inc.Inventor: Arthur H. Gerber
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Patent number: 6114462Abstract: A chemically amplified positive resist composition contains (A) an organic solvent, (B) a base resin in the form of a polymer having at least one acid labile group and crosslinked within a molecule and/or between molecules with a crosslinking group having a C--O--C linkage, the polymer having a weight average molecular weight of 1,000-500,000, (C) a photoacid generator, (D) a basic compound, and (E) an aromatic compound having a group .tbd.C--COOH in a molecule. The composition has a high alkali dissolution contrast, high sensitivity and high resolution.Type: GrantFiled: April 30, 1999Date of Patent: September 5, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Osamu Watanabe, Tomoyoshi Furihata, Yoshihumi Takeda, Shigehiro Nagura, Toshinobu Ishihara, Tsuguo Yamaoka
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Patent number: 6033826Abstract: A polymer of polyhydroxystyrene derivative containing an acetal or ketal group which can easily be eliminated in the presence of an acid in the molecule and having a very narrow molecular weight distribution gives a resist material suitable for forming ultrafine patterns excellent in resolution, heat resistance, mask linearity, and other properties without causing problems of delay time and the like.Type: GrantFiled: December 19, 1996Date of Patent: March 7, 2000Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono
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Patent number: 5998566Abstract: The improved phenol derivatives having a phenolic structure as part of the molecular backbone are produced by reacting condensed polycyclic aromatic hydrocarbons, either individually or in combination with unsaturated cyclic aliphatic hydrocarbons, with phenols in the presence of Friedel-Crafts catalysts and have softening points of no more than 150.degree. C., number average molecular weights of 250-800 and phenolic hydroxyl equivalents of 140-850 g/eq. These phenol derivatives are useful either as starting materials for the manufacture of heat-resistant thermosetting resins or as modifiers thereof. They can be produced by reacting the indicated components in the presence of Friedel-Crafts catalysts, typically a mixture of hydrogen fluoride and boron trifluoride, at temperature of 0-350.degree. C.Type: GrantFiled: November 30, 1995Date of Patent: December 7, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takashi Kojima, Takafumi Yoshimura
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Patent number: 5976759Abstract: A polymer composition comprising (i) a polymer (a) having a monomer unit containing a functional group A which becomes alkali-soluble by heating in the presence of an acid, (ii) a polymer (b) having a monomer unit containing a functional group B which also becomes alkali-soluble, but less easily than the functional group A, by heating in the presence of an acid, and if necessary in addition to (i) and (ii) or in place of (ii), (iii) a phenolic compound having a weight-average molecular weight of 300 to 15,000 gives together with an photoacid generator a resist material suitable for forming a pattern excellent in sensitivity, resolution, mask linearity and other properties.Type: GrantFiled: December 19, 1996Date of Patent: November 2, 1999Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono
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Patent number: 5905118Abstract: Disclosed herein are terpolymers of styrene, acrylonitrile and dimethyl styrene phosphonate and blends thereof with poly(styrene acrylonitrile) polymers and polymers and copolymers of methylmethacrylate.Type: GrantFiled: April 24, 1998Date of Patent: May 18, 1999Assignee: Bayer Antwerpen S.A./N.V.Inventor: Allen Robert Padwa
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Patent number: 5580929Abstract: An interpenetrating gel and a method of forming an interpenetrating gel which undergoes a significantly large volume change in response to a physical or chemical stimululs is disclosed.Type: GrantFiled: April 4, 1995Date of Patent: December 3, 1996Assignee: Massachusetts Institute of TechnologyInventors: Toyoichi Tanaka, Franck Ilmain, Etsuo Kokufuta, Masahiko Annaka
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Patent number: 5548029Abstract: Graft copolymers which are isoolefin/para-alkylstyrene copolymer represented by the formula ##STR1## in which R and R' can be hydrogen, alkyl, and the primary and secondary alkyl halides, "a" ranges from about 14 to about 70,000, "b" ranges from 0 to about 70,000, "c" ranges from 0 to about 70,000, "d" ranges from about 1 to about 70,000, X is a halogen, and Nu is a nucleophilic residue provided by a polymeric nucleophile.Type: GrantFiled: March 15, 1995Date of Patent: August 20, 1996Assignee: Exxon Chemical Patents Inc.Inventors: Kenneth W. Powers, Hsien-Chang Wang, T-C. Chung, Anthony J. Dias, Joseph A. Olkusz
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Patent number: 5475043Abstract: A material with variable viscoelasticity is composed of an electrically insulating polymeric material, and fine particles dispersed therein and capable of electric polarization under an applied electric field. The particles may, for example, be of a conjugated and unsaturated organic compound, a polyelectrolyte, or an organometallic complex salt. The material is capable of a reversible change of viscoelasticity depending on the intensity of the applied electric field.Type: GrantFiled: August 4, 1994Date of Patent: December 12, 1995Assignee: Kabushiki Kaisha Toyota Chuo KenkyushoInventors: Tohru Shiga, Norio Sato, Yoshiharu Hirose, Akane Okada, Takashi Ohta, Toshio Kurauchi
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Patent number: 5403893Abstract: An interpenetrating gel and a method of forming an interpenetrating gel which undergoes a significantly large volume change in response to a physical or chemical stimululs is disclosed.Type: GrantFiled: November 10, 1993Date of Patent: April 4, 1995Assignee: Massachusetts Institute of TechnologyInventors: Toyoichi Tanaka, Franck Ilmain, Etsuo Kokufuta, Masahiko Annaka
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Patent number: 5349019Abstract: New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils.Copolymers comprising as comonomers therein from 50 to 99.9% by weight of a C.sub.14 -C.sub.22 -alkyl(meth)acrylate and 50 to 0.1% by weight of a comonomer derived from a compound comprising a single polymerizable C.dbd.C group and these copolymers or their mixture with C.sub.14 -C.sub.22 -alkyl poly(meth)acrylates having enhanced pour point depressant properties.Type: GrantFiled: September 2, 1993Date of Patent: September 20, 1994Assignee: HoechstInventors: Herbert Wirtz, Sigmar-Peter von Halasz, Michael Feustel, Juliane Balzer
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Patent number: 5306774Abstract: A miscible blend comprising (a) a poly(alkylene oxide) vinyl carboxylic ester polymer and (b) a polymer bearing acidic functional groups has been discovered, with the blend being employable as a protective coating, membrane or film exhibiting good mechanical stablility and chemical resistance.Type: GrantFiled: December 2, 1991Date of Patent: April 26, 1994Assignee: Eastman Kodak CompanyInventors: Christine J. T. Landry, David M. Teegarden, Bradley K. Coltrain, Wayne T. Ferrar
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Patent number: 5264526Abstract: Light-stabilized acrylonitrile polymer fiber and polyurethane elastomer fiber are made by incorporating a copolymer of 20-80 weight % of a benzophenone compound of the formula: ##STR1## wherein R is hydrogen or methyl and X is --O--, --OCH.sub.2 CH.sub.2 O-- or --OCH.sub.2 CH(OH)CH.sub.2 O--, and 80-20 weight % of an ethylenically unsaturated monomer with an acrylonitrile polymer or a polyurethane elastomer; and a dope of the polymer mixture in an organic solvent is wet-spun into a fiber.Type: GrantFiled: November 20, 1991Date of Patent: November 23, 1993Assignee: Ipposha Oil Industries Co., Ltd.Inventors: Kazuto Kashiwai, Michihira Endoh, Shinichi Kumagae
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Patent number: 5237012Abstract: Novel stabilized compositions comprise organic material normally subject to oxidative degradation stabilized by the presence therein of a stabilizing quantity of a novel, at least partial ester of poly(vinylphenol) and a 3,5-dialkyl-4-hydroxybenzoic acid wherein at least one of the alkyl groups is a bulky alkyl.Type: GrantFiled: October 2, 1992Date of Patent: August 17, 1993Assignee: Shell Oil CompanyInventor: Pui K. Wong
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Patent number: 5185407Abstract: Novel stabilized compositions comprise organic material normally subject to oxidative degradation stabilized by the presence therein of a stabilizing quantity of a novel, at least partial ester of poly(vinylphenol) and a 3,5-dialkyl-4-hydroxybenzoic acid wherein at least one of the alkyl groups is a bulky alkyl.Type: GrantFiled: August 29, 1991Date of Patent: February 9, 1993Assignee: Shell Oil CompanyInventor: Pui K. Wong
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Patent number: 5173547Abstract: Copolymers and graft copolymers of perfluoroalkylacrylates or methacrylates and esters of the general formula (I) or (II) ##STR1## wherein R, R.sub.1 and R.sub.2 denote hydrogen or methyl,p denotes 2 to 6,q denotes 2 to 200 andx and y denote 3-30,are outstandingly suitable for finishing textile materials, leather and paper.Type: GrantFiled: October 2, 1990Date of Patent: December 22, 1992Assignee: Bayer AktiengesellschaftInventors: Jutta Rottger, Wilfried Kortmann, deceased, Karl-Erwin Piejko, Gerd F. Renner
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Patent number: 5081183Abstract: The present invention provides a poly(alpha-ketoester) compound represented by the formula (1); ##STR1## wherein G is a residue of an active hydrogen-containing compound G--(X--H).sub.n, or an alkyl, aryl, aralkyl, alkenyl, alkynyl group having 3 to 20 carbon atoms which may contain oxygen or nitrogen atoms, or a polymeric compound residue, X is an oxygen atom or --CH.sub.2, n is an integer of 3 to 1,000, R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or an aryl group, and a production thereof.Type: GrantFiled: January 12, 1990Date of Patent: January 14, 1992Assignee: Nippon Paint Co., Ltd.Inventors: Aoki Kei, Takagawa Ryozo, Tomita Nobuaki, Mori Hirohiko
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Patent number: 4937291Abstract: Thermoplastic elastomer blends containing polyvinyl chloride having improved oil resistance and low compression set are made by blending a crosslinked nitrile rubber with a polyvinyl chloride-acrylate copolymer. The amount of nitrile rubber can vary over a wide range as from about 1 part to about 400 parts by weight for every 100 parts by weight of the polyvinyl chloride-acrylate copolymer. The polyvinyl chloride-acrylate copolymer has an inherent viscosity of from about 0.3 to about 4.0 and is made from a vinyl chloride monomer with an optional vinyl component comonomer and one or more acrylate monomers having the formula ##STR1## wherein R.sup.1 is an aliphatic, an aromatic, or combinations thereof, having from 1 to 18 carbon atoms, or a halogen derivative thereof, or hydrogen, and R.sup.Type: GrantFiled: September 9, 1988Date of Patent: June 26, 1990Assignee: The B.F. Goodrich CompanyInventors: William S. Greenlee, Josef C. Vyvoda
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Patent number: 4935468Abstract: Thermoplastic elastomer blends containing polyvinyl chloride having improved oil resistance, exceptionally low compression set and softness are made by mixing a polyvinyl chloride-acrylate copolymer with effective amounts of cured acrylate elastomers. The polyvinyl chloride-acrylate copolymer has an inherent viscosity of from about 0.3 to about 4.0 and is made from a vinyl constituent which is a vinyl chloride monomer with an optional vinyl component comonomer and one or more acrylate monomers having the formula ##STR1## wherein R.sup.1 is an aliphatic, an aromatic, or combinations thereof, having from 1 to 18 carbon atoms, or a halogen derivative thereof, or hydrogen, and R.sup.Type: GrantFiled: September 9, 1988Date of Patent: June 19, 1990Assignee: The B. F. Goodrich CompanyInventors: William S. Greenlee, Josef C. Vyvoda, Fred R. Wolf
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Patent number: 4912169Abstract: Adhesive compositions containing a polymeric additive which is polymerized from monomers selected from C.sub.1 -C.sub.20 alkyl and cycloalkyl acrylate, C.sub.1 -C.sub.20 alkyl and cycloalkyl methacrylate, free-radical polymerizable olefinic acids, and optionally other ethylenically unsaturated monomers wherein said polymeric additive has a number average molecular weight less than about 35,000 and a softening point greater than about 40.degree. C.Type: GrantFiled: April 27, 1989Date of Patent: March 27, 1990Assignee: Rohm and Haas CompanyInventors: Judith L. Whitmire, Patricia M. Lesko, Timothy G. Wood
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Patent number: 4861821Abstract: Copolymers produced from 0.5-20% by weight mono-, bis- or trismethylolphenyl allyl ether (I) of formula: ##STR1## n being from 1 to 3, and from 80-99.5 % by weight ethylenic monomers, at least one being a (meth)acrylic monomer are useful in the preparation of coatings, particularly in the field of paints, varnishes, inks and adhesives. Radical polymerization is employed with different stages of polymerization.Type: GrantFiled: June 26, 1987Date of Patent: August 29, 1989Assignee: Societe Chimique Des Charbonnages S.A.Inventors: Jean Aubry, Serge Cassiani-Ingoni, Remi Hauschild
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Patent number: 4855359Abstract: A thermosetting coating composition useful as a primer for metal automobile and truck bodies having excellent chip resistance which contains a binder, a liquid carrier for the binder and pigments; wherein the binder contains(1) a hydroxyl terminated copolymer of styrene/allyl alcohol polymer chain extended with caprolactone;(2) a hydroxy functional polyester urethane and(3) an alkylated melamine resin or blocked poly-isocyanate crosslinking agent.Type: GrantFiled: January 20, 1988Date of Patent: August 8, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Rose A. Ryntz, Karen A. Surcina, Kenneth R. Kurple
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Patent number: 4812522Abstract: A molecularly miscible blend of a linear alternating polymer of carbon monoxide and an ethylenically unsaturated hydrocarbon and a polyvinyl phenol.Type: GrantFiled: December 4, 1987Date of Patent: March 14, 1989Assignee: Shell Oil CompanyInventor: Dale L. Handlin, Jr.
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Patent number: 4725503Abstract: Wires of poly-.epsilon.-caprolactam with a diameter of from 2 to 8 mm and a strength of from 35 to 45 cN/tex containing from 0.1 to 10% by weight, based on poly-.epsilon.-caprolactam, of titanium dioxide pigment are useful as anchoring wires in the cultivation of wine and fruit and for fences around pasture land.Type: GrantFiled: August 29, 1985Date of Patent: February 16, 1988Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Gelhaar, Rudolf Braeckeler, Robert McDonald, Richard Buechele
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Patent number: 4310650Abstract: Photostable and weather stable absorping copolymers have been prepared from acrylic esters such as methyl methacrylate containing 0.1 to 5% of an 2-hydroxy-allyl benzophenone, preferably the 4,4' dimethoxy derivative thereof. The pendant benzophenone chromophores protect the acrylic backbone and when photoexcited do not degrade the ester side chain, nor abstract hydrogen from the backbone.Type: GrantFiled: March 3, 1980Date of Patent: January 12, 1982Assignee: California Institute of TechnologyInventors: Amitava Gupta, Andre H. Yavrouian
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Patent number: 4281080Abstract: Age resistant resin which comprises a composition selected from (A) a composition having a softening point in the range of 0.degree. C. to about 140.degree. C. comprising units derived from selected aliphatic diolefins and aliphatic monoolefins, which can be modified with units derived from dicyclopentadiene, and certain vinyl aromatic compounds, and selected phenol or amine type compounds and (B) a composition having a softening point in the range of about 60.degree. C. to about 110.degree. C. comprising units derived from monoolefins and vinyl aromatic compounds, which can be modified with aliphatic diolefins, and selected phenol and amine type compounds. Such age resistant resins have particular utility when admixed with various rubbery materials and thermoplastics to create pressure sensitive adhesives and hot melt adhesives.Type: GrantFiled: February 17, 1977Date of Patent: July 28, 1981Assignee: The Goodyear Tire & Rubber CompanyInventors: Herbert L. Bullard, Robert A. Osborn
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Patent number: 4221700Abstract: A stabilized synthetic polymer composition comprising(1) 100 parts by weight of a synthetic polymer,(2) 0.001 to 5 parts by weight of a poly(alkylated alkenylphenol) composed substantially of monomeric units represented by the following formula (I) ##STR1## wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sub.1 represents an alkyl group having 1 to 18 carbon atoms; and R.sub.2 represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; and(3) 0.001 to 5 parts by weight of an auxiliary stabilizer selected from the group consisting of polyhydric alcohol esters of alkylthioalkanoic acids, polyesters of thiodipropionic acid and organic phosphite compounds.Type: GrantFiled: July 5, 1978Date of Patent: September 9, 1980Assignee: Maruzen Oil Co., Ltd.Inventors: Motomobu Minagawa, Mitsuo Akutsu, Hiroshi Fujiwara, Masayuki Kashiki
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Patent number: 4187259Abstract: Polymer blends having improved hydrolytic stability comprise, in admixture, (1) a linear aromatic polyester prepared from an aromatic dicarboxylic acid and a bisphenol, and (2) a cross-linked acrylate-methacrylate copolymer. The blends are useful in preparation of films and molded articles.Type: GrantFiled: June 30, 1978Date of Patent: February 5, 1980Assignee: Hooker Chemicals & Plastics Corp.Inventor: Gideon Salee
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Patent number: 4181635Abstract: A pressure-sensitive adhesive composition having excellent tackiness and improved thermal resistance comprises (A) a low molecular weight polyisoprene, which may be obtained by polymerizing isoprene monomer with the aid of a lithium-type catalyst, said polyisoprene having a cis-1,4 content of not less than 75%, a viscosity average molecular weight of 8,000 to 77,000 and an Mw/Mn value (Mw: weight average molecular weight; Mn: number average molecular weight) of 1.0 to 2.7 and (B) an elastomer.Type: GrantFiled: February 17, 1978Date of Patent: January 1, 1980Assignee: Kuraray Co., Ltd.Inventors: Hideo Takamatsu, Shobu Minatono, Katsuyoshi Terao, Junnosuke Yamauchi
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Patent number: RE34640Abstract: Block copolymers compose a polyisobutylene rubbery soft segment of M.sub.n of about 5,000 to above 500,000 and glassy hard segments of M.sub.n of about 5,000 or higher and usually about 10,000 to 35,000 or more, are made by preparing a living polymer block of the polyisobutylene and then polymerizing on said living polyisobutylene block the glassy hard segments by adding thereto an electron donor having a donor number of 15 to 50 and then adding and polymerizing the monomers for the glassy hard segments. The monomers for the glassy hard segments are styrene and its derivatives and indene and its derivatives and mixtures thereof.Type: GrantFiled: April 28, 1992Date of Patent: June 14, 1994Assignee: University of AkronInventors: Joseph P. Kennedy, Judit E. Puskas, Gabor Kaszas, William G. Hager