From Monomer Containing An Acetylenic Group Patents (Class 526/285)
  • Patent number: 6344523
    Abstract: The invention provides a method for promoting the curing reactions of an acetylenic oligomer or polymer, characterized in that the oligomer or polymer is cured in the presence of sulfur or an organic sulfur derivative which is capable of lowering the temperature of cure of the oligomer or polymer. The invention also provides a process for producing a polyimide oligomer or polymer containing an aliphatic or aromatic disulfide moiety which is covalently bound to, and forms an integral part of the oligomer or polymer and which is capable of lowering the temperature of cure of the oligomer or polymer, characterised in that a suitable amount of a diamino-disulfide or dianhydride-disulfide, or any suitable derivative or precursor thereof, is introduced into the mixture of aromatic diamines, tetracarboxylic dianhydrides, and the phenylethynyl-substituted amine or anhydride normally used for the reparation of the oligo-imide.
    Type: Grant
    Filed: December 10, 1999
    Date of Patent: February 5, 2002
    Assignees: Commonwealth Scientific and Industrial Research Organization of Campbell, The Boeing Company
    Inventors: David Geoffrey Hawthorne, Jonathan Howard Hodgkin
  • Patent number: 6344286
    Abstract: A diacetylene-based polymer of the following formula (I): wherein, Ar represents a light emitting group. The present invention also provides an electroluminescence device having a structure of anode/luminescent layer/cathode added with a transfer layer and/or a reflection layer, if necessary, in which the luminescent layer is made of the diacetylene-based polymer containing the light emitting group. The polymer of the present invention can be easily blended with a variety of macromolecules for general use.
    Type: Grant
    Filed: August 19, 1999
    Date of Patent: February 5, 2002
    Assignees: Hanwha Chemical Corporation, Korea Institute of Science and Technology
    Inventors: Chung Yup Kim, Hyun Nam Cho, Dong Young Kim, Young Chul Kim, Jae-Min Hong, Jai Kyeong Kim, Jae-Woong Yu
  • Publication number: 20020001734
    Abstract: An organic EL device employing polymer material includes a structure in which a luminous layer formed of a polymer indicated by 1
    Type: Application
    Filed: April 26, 2001
    Publication date: January 3, 2002
    Inventors: Kota Yoshikawa, Masashi Kijima, Hideki Shirakawa, Ikuo Kinoshita
  • Patent number: 6331602
    Abstract: This invention relates to a monomer shown by the general formula [1] (wherein X′ is a cyclic hydrocarbon residue containing polymerizable double bond(s), which may have a substituent, Z is a spacer or a direct bond and R is a substituted alkyl or alkenyl group having one or two protected hydroxyl groups as substituent) and a polymer containing a segment derived from the above monomer. The said polymer is useful for a resist composition, etc. utilized in the production of semiconductor elements, etc. and the said monomer is useful as a starting material for the polymer, and a resist composition using the said polymer can remarkably advantageously be used as a resist material for ArF excimer laser beams which has been considered to be a valuable technology for exposure belonging to the coming generation.
    Type: Grant
    Filed: September 6, 2000
    Date of Patent: December 18, 2001
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventor: Motoshige Sumino
  • Patent number: 6291606
    Abstract: The present invention provides methods for obtaining highly stereoregular polyacetylenes from organorhodium catalysts in aqueous media in high yield. These methods afford substantial advantages in that they are rapid, economical, and utilize environmentally benign solvents. The present invention further provides methods for making thin films of polyphenylacetylenes that are tough and transparent.
    Type: Grant
    Filed: April 16, 1999
    Date of Patent: September 18, 2001
    Assignee: The Hong Kong University of Science and Technology
    Inventors: Ben Zhong Tang, Wa Hong Poon
  • Patent number: 6288188
    Abstract: An oligomer, uncured polymer or cured polymer comprising the reaction product of one or more polyfunctional compounds containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic acetylene groups wherein at least some of the polyfunctional compounds contain three or more reactive groups. Such oligomers and uncured polymers may be cured to form cured polymers which are useful as dielectrics in the microelectronics industry, especially for dielectrics in integrated circuits.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: September 11, 2001
    Assignee: The Dow Chemical Company
    Inventors: James P. Godschalx, Duane R. Romer, Zenon Lysenko, Michael E. Mills
  • Patent number: 6271280
    Abstract: Intermediate compositions comprising ethynylorgano polyorganosiloxanes are prepared by hydrosilylation of an olefinic hydroxy compound followed by reaction with a propargyl halide, or by hydrosilylation of a diethynyl compound. The intermediate compositions may be oxidatively coupled to form poly(conjugated diacetylenic)polyorganosiloxanes. The latter may be cured thermally or by radiation to form cured compositions useful as release coatings or conformal coatings.
    Type: Grant
    Filed: April 19, 2000
    Date of Patent: August 7, 2001
    Assignee: General Electric Company
    Inventors: Sylvie Louise Boileau, Anna Elzbieta Kowalewska, Laurent Bouteiller, Matthew David Butts, Slawomir Rubinsztajn
  • Publication number: 20010007009
    Abstract: Polymers based on monomers having a C-C double bond and/or C-C triple bond are prepared by polymerization of these monomers in the presence of a catalyst system comprising as active constituents
    Type: Application
    Filed: December 5, 2000
    Publication date: July 5, 2001
    Inventors: Lambertus Manders, Marc Oliver Kristen, Alexander Haunschild, Michael Geprags
  • Patent number: 6194529
    Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the characteristic optical and other properties of polyacetylenes.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: February 27, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6180728
    Abstract: The present invention relates to apparatus for the semi-continuous polymerization of monomers with the use of a chain initiator. This apparatus is characterized in that it comprises a reactor (1) arranged with its axis substantially vertical and defining a lower, frustoconical part (III), an upper atonization part (I) and an intermediate part (II), the reactor (1) having monomer and initiator inlet apertures (8, 10, 20, 21) at least one outlet aperture (12), a recycling duct (15) connected at one end to the outlet aperture (12) and at the other end to the upper part (I) through at least one atomizer (9), and a stirrer (25). The apparatus according to the invention has the particular advantage of being usable for reactions with any type of chain initiator and catalyst, whether they are solid, liquid or in suspension.
    Type: Grant
    Filed: October 5, 1999
    Date of Patent: January 30, 2001
    Assignee: Linde Aktiengesellschaft
    Inventor: Pasquale Fanelli
  • Patent number: 6160068
    Abstract: This invention relates to a monomer shown by the general formula [1] ##STR1## (wherein X' is a cyclic hydrocarbon residue containing polymerizable double bond(s), which may have a substituent, Z is a spacer or a direct bond and R is a substituted alkyl or alkenyl group having one or two protected hydroxyl groups as substituent) and a polymer containing a segment derived from the above monomer.The said polymer is useful for a resist composition, etc. utilized in the production of semiconductor elements, etc. and the said monomer is useful as a starting material for the polymer, and a resist composition using the said polymer can remarkably advantageously be used as a resist material for ArF excimer laser beams which has been considered to be a valuable technology for exposure belonging to the coming generation.
    Type: Grant
    Filed: November 18, 1998
    Date of Patent: December 12, 2000
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventor: Motoshige Sumino
  • Patent number: 6114463
    Abstract: The present invention relates to (co)polymers which contain at least one repeating structural chain unit of the general formula (1) and/or (2) and optionally repeating units of the general formula (3) ##STR1## in which L.sup.1 and L.sup.2, independently of each other, represent a photoluminescent grouping, a process for their preparation, their use in electroluminescent devices and the electroluminescent devices.
    Type: Grant
    Filed: August 11, 1997
    Date of Patent: September 5, 2000
    Assignee: Bayer AG
    Inventors: Yun Chen, Burkhard Kohler, Rolf Wehrmann, Andreas Elschner, Ralf Dujardin
  • Patent number: 6093779
    Abstract: Compositions comprising at least one nonvolatile acetylene alone or together with a strained cycloolefin and catalytic amounts of a catalyst for metathesis polymerization, which comprise at least one one-component catalyst from the group molybdenum compounds, tungsten compounds, niobium compounds and tantalum compounds which comprise (a) either at least two methyl groups or two monosubstituted methyl groups without .alpha. hydrogen atoms in the substituent or (b) at least one halogen and only one silylmethyl group attached to the metal. The storage-stable compositions can be polymerized by the action of actinic radiation or by short-term irradiation and subsequent thermal curing. The polymers can be used to prepare shaped articles, films, coatings and relief images.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: July 25, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Muhlebach
  • Patent number: 5986011
    Abstract: The present invention provides a method for the polymerization of free-radically polymerizable vinyl monomers in a batch reactor under essential adiabatic conditions.
    Type: Grant
    Filed: June 6, 1997
    Date of Patent: November 16, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Mark F. Ellis
  • Patent number: 5973033
    Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.
    Type: Grant
    Filed: October 26, 1998
    Date of Patent: October 26, 1999
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Hilmar Koerner
  • Patent number: 5973092
    Abstract: A thermosetting resin is formed from cyclopentadiene and a propargyl halide. The resin can be used with carbon fibers to form a carbon-carbon composite.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: October 26, 1999
    Assignee: The University of Southern Mississippi
    Inventors: Lon J. Mathias, Gregory J. Tregre
  • Patent number: 5968640
    Abstract: The morphology of multidimensional, thermally stable oligomers is combined with the inclusion of charge carrier linkages within the polymer arms to produce thermally stable advanced composites from cured oligomers that are conductive or semiconductive if suitably doped.
    Type: Grant
    Filed: September 5, 1985
    Date of Patent: October 19, 1999
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard, Larry P. Torre
  • Patent number: 5965679
    Abstract: An oligomer, uncured polymer or cured polymer comprising the reaction product of one or more polyfunctional compounds containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic acetylene groups wherein at least some of the polyfunctional compounds contain three or more reactive groups. Such oligomers and uncured polymers may be cured to form cured polymers which are useful as dielectrics in the microelectronics industry, especially for dielectrics in integrated circuits.
    Type: Grant
    Filed: April 1, 1997
    Date of Patent: October 12, 1999
    Assignee: The Dow Chemical Company
    Inventors: James P. Godschalx, Duane R. Romer, Ying Hung So, Zenon Lysenko, Michael E. Mills, Gary R. Buske, Paul H. Townsend, III, Dennis W. Smith, Jr., Steven J. Martin, Robert A. DeVries
  • Patent number: 5885717
    Abstract: A composite tack-free film having a film substrate with opposing surfaces, bearing on at least one of said surfaces a highly crosslinked, film-forming acrylate composition containing from about 25 to about 78 of at least one lower alkyl (meth)acrylate ester and from about 10 to about 60 percent vinyl acetate and at least about 1 percent of a polar monomer, wherein the acrylate composition is capable of attaching temporarily to polyimide film surface to provide a substantially air-tight seal and being cleanly removable from said polyimide film surface leaving no visible residue, even after being subjected to elevated temperatures.
    Type: Grant
    Filed: January 15, 1998
    Date of Patent: March 23, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jack L. Price, James N. Kellen
  • Patent number: 5866665
    Abstract: Substantially random ethylene copolymers containing at least 3.0 mole percent of geminally disubstituted olefin monomers are described. The geminally disubstituted olefin monomers can be represented by the generic formula R.sub.1 =R.sub.2 (R.sub.3)(R.sub.4), where R.sub.1 is CH.sub.2, R.sub.2 is C, and R.sub.3 and R.sub.4 are, independently, essentially linear hydrocarbyl groups having from 1 to 30 carbon atoms, or more, and containing one carbon atom bound directly to R.sub.2. The copolymers can be prepared by coordination polymerization by means of contacting at least one geminally disubstituted olefin monomer and ethylene, optionally with one or more other coordination polymerizable monomers, with a catalyst system comprising a monocyclopentadienyl, heteroatom-containing Group 4 transition metal catalyst component.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: February 2, 1999
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Timothy Daniel Shaffer, Jo Ann Marie Canich, Kevin Richard Squire
  • Patent number: 5864050
    Abstract: The present invention provides a curable resin compound which is soluble in organic solvents and easy to use, and a method for producing the same. The curable resin compound comprises a structure and crosslinkable groups which end-cap the structure, the structure comprising three or four non-substituted benzene rings each of which is joined with each adjacent benzene ring by an ether or ketone linkage so that both types of linkages are present in the structure. Though the curable resin compound exhibits satisfactory solubilities in organic solvents, a composition comprising the compound can be cured by a crosslinking reaction to be insoluble in the organic solvents while being provided with improved solvent resistance and chemical resistance. Accordingly, the present invention also provides a cured-resin material derived from the aforementioned curable resin compound, the cured-resin material being excellent in solvent resistance, chemical resistance and thermal resistance.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: January 26, 1999
    Assignee: Alps Electric Co., Ltd. and Shiro Koayashi
    Inventors: Yoshihiro Taguchi, Shiro Kobayashi, Hiroshi Uyama, Atsushi Nakamura
  • Patent number: 5807953
    Abstract: The present invention is a thermoset having the repeating unit: ##STR1## where R.sup.1 and R.sup.2 are independently selected from the group consing of hydrogen, unsubstituted alkyl groups, substituted alkyl groups, unsubstituted aryl groups, and substituted aryl groups, where Ae.sup.1 and Ae.sup.2 are independently selected groups with one or more unsaturated carbon-carbon bond and at least two crosslinking moieties, where Ar.sup.1 and Ar.sup.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: September 15, 1998
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Daniel Bucca, Teddy M. Keller
  • Patent number: 5756597
    Abstract: Thermomechanical and thermo-oxidative stabilities in resin composites across the range of aerospace "engineering thermoplastic" resins are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities of the general formula: ##STR1## in the oligomers, wherein ##STR2## .beta.=the residue an organic radical selected from the group consisting of: ##STR3## R.sub.8 =a divalent organic radical; X=halogen;Me=methylT=allyl or methallyl,G=--CH.sub.2 --, --S--, --CO--, --SO--, --O--, --CHR.sub.3 --, or --C(R.sub.3).sub.2 --;i=1 or 2;R.sub.3 =hydrogen, lower alkyl, lower alkoxy, aryl, or aryloxy; and.THETA.=--C.tbd.N, --O--C.tbd.N, --S--C.tbd.N, or --CR.sub.3 .dbd.C(R.sub.3).sub.2.
    Type: Grant
    Filed: February 12, 1997
    Date of Patent: May 26, 1998
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowtiz, Clyde H. Sheppard
  • Patent number: 5753768
    Abstract: The present invention provides a method for the polymerization of free-radically polymerizable vinyl monomers in a batch reactor under essential adiabatic conditions.
    Type: Grant
    Filed: January 14, 1997
    Date of Patent: May 19, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Mark F. Ellis
  • Patent number: 5747618
    Abstract: The invention features linear copolymers prepared from mixtures of allenes and alkynes. The new copolymers have the formula: ##STR1## wherein R.sub.1 through R.sub.6 are, independently, H, an alkyl, an aryl, a phenyl or substituted phenyl, an alkoxy, or an aryloxyl, x+n is 1 to 10,000, and m is 1 to 10,000. The invention also features efficient methods of preparing the new copolymers using nickel or palladium catalysts.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: May 5, 1998
    Inventors: Bruce M. Novak, Mitsuru Nakano
  • Patent number: 5705503
    Abstract: Addition polymers containing functionally substituted polycyclic repeat units are prepared in the presence of a single or multicomponent catalyst system containing a palladium metal ion source. The catalysts are not poisoned by functional substituents and show good catalytic activity for polymerizing both endo and exo isomers of the substituted monomers. Optionally, the polymers are terminated with olefinic end groups.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: January 6, 1998
    Inventors: Brian Leslie Goodall, Wilhelm Risse, Joice P. Mathew
  • Patent number: 5686027
    Abstract: A novel polyphenylene resin is formed by the polycyclotrimerization of vinylethynylbenzene, diethynylbenzene and phenylacetylene. Polymerization is carried out under conditions which result in the retention of unreacted vinyl groups from the vinylethynylbenzene component, which are then susceptible to crosslinking. The polymer is useful in the formation of high-performance carbon-carbon composites, producing an unusually high char yield with advantageous handling and processing characteristics.
    Type: Grant
    Filed: December 5, 1989
    Date of Patent: November 11, 1997
    Assignee: Aerojet-General Corporation
    Inventors: Robert Earl Olsen, Harlan Frederick Reese, Stephen John Backlund
  • Patent number: 5686520
    Abstract: Compounds having the formula ##STR1## in which R is a member selected from the group consisting of H, CH.sub.2 .dbd.CH--, and CH.tbd.C--, R' is a member selected from the group consisting of --CH.dbd.CH.sub.2 and --C.tbd.CH, and n is zero, 1, 2, 3 or 4, are useful as fluidizers for polyphenylene prepolymers, rendering the latter sufficiently fluid for processing to form high-performance carbonaceous materials. These compounds are also useful themselves as monomers and prepolymers for the formation of the high-performance carbonaceous materials.
    Type: Grant
    Filed: December 5, 1989
    Date of Patent: November 11, 1997
    Assignee: Aerojet-General Corporation
    Inventors: Robert Earl Olsen, Stephen John Backlund, Harlan Frederick Reese
  • Patent number: 5681870
    Abstract: Novel class of organoboron thermosetting polymer and ceramics that are fod from an organoboron polymer having a backbone with a repeating of at least one alkynyl group, at least one silyl group, at least one boranyl group, optionally at least one siloxyl group, and optionally an aryldisilyl group. The boron containing units in and the silicon containing units can be arranged in either random occurrences between each other or in the form of interdispersed block-type structures of each unit. The thermosetting polymers are useful as high temperature, oxidatively stable thermosetting plastics and for microelectronic applications.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: October 28, 1997
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, Raj A. Sundar
  • Patent number: 5637646
    Abstract: The present invention provides a method for the polymerization of free-radically polymerizable vinyl monomers in a batch reactor under essential adiabatic conditions.
    Type: Grant
    Filed: December 14, 1995
    Date of Patent: June 10, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Mark F. Ellis
  • Patent number: 5616669
    Abstract: A method of manufacturing a soluble conductive poly acetylene derivative represented by the following formula (I) including the steps of synthesizing a propargyl derivative by reacting a propargyl halogenide and an alkyne derivative and polymerizing the propargyl derivative in the presence of a transition metal catalyst. The thus obtained novel soluble conductive polymer can be used in a display device. ##STR1## (wherein, X is oxygen atom or sulfur atom, R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, C.sub.2 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl; or when one of R.sub.1 and R.sub.2 is phenyl, the other is hydrogen or C.sub.1 -C.sub.10 alkyl, n is an integer between 50.about.200). The soluble conductive polymer of the present invention can be easily polymerized and has good stability and electrochromic characteristics when applied to display devices.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 1, 1997
    Assignee: Samsung Display Devices Co., Ltd.
    Inventors: Sung-ho Jin, Shin-woong Kang
  • Patent number: 5606014
    Abstract: Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as under nitrogen at room temperature.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: February 25, 1997
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Jr., Paul M. Hergenrother
  • Patent number: 5596054
    Abstract: There are disclosed a transition metal compound of the general formula RMX.sub.a-1 L.sub.b (R is as a .pi. ligand, a fused polycyclic cyclopentadienyl group in which at least one of many-membered rings to which cyclopentadienyl groups are fusedly bonded is a saturated ring, M is a transition metal, X is a .sigma. ligand, L is a Lewis base, a is the valency of M, and b is 0, 1 or 2); a polymerization catalyst for styrene, etc. comprising the above transition metal, preferably further comprising an oxygen atom containing compound ionic compound or organoboron compound and optionally a Lewis base; and a process for producing a polymer of a compound containing an ethylenically unsaturated double bond or an acetylenic polymer, especially a syndiotactic polystyrene by using the above polymerization catalyst. The catalyst is particularly effectivive for producing highly syndiotactic polystyrene minimized in residual metals amounts at a low cost in enhanced efficiency.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: January 21, 1997
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventor: Mizutomo Takeuchi
  • Patent number: 5594058
    Abstract: A novel polyphenylene resin is formed by the polycyclotrimerization of vinylethynylbenzene, diethynylbenzene and phenylacetylene. Polymerization is carried out under conditions which result in the retention of unreacted vinyl groups from the vinylethynylbenzene component, which are then susceptible to crosslinking. The polymer is useful in the formation of high-performance carbon--carbon composites, producing an unusually high char yield with advantageous handling and processing characteristics.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: January 14, 1997
    Assignee: Aerojet- General Corporation
    Inventors: Robert E. Olsen, Harlan F. Reese, Stephen J. Backlund
  • Patent number: 5576375
    Abstract: A novel resin is formed by the copolymerization of vinylethynylbenzene and diethynylbenzene. Polymerization is carried out under conditions which result in the retention of both unreacted vinyl groups from the vinylethynylbenzene component and unreacted ethynyl groups from the diethynyl component, both of which are then susceptible to crosslinking. The polymer is useful in the formation of high-performance carbon-carbon composites, producing an unusually high char yield with advantageous handling and processing characteristics.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: November 19, 1996
    Assignee: Aerojet- General Corporation
    Inventors: Robert E. Olsen, Harlan F. Reese, Stephen J. Backlund
  • Patent number: 5559191
    Abstract: This invention relates to a process for functionalising synthetic hydrocarbyl polymers having at least one olefinic group by (i) reacting at elevated temperature the synthetic hydrocarbyl polymer with an alkyne compound substituted with at least one electron withdrawing --C(O)R or a --CN group so that the olefinic group in the polymer reacts with the alkyne group of the alkyne compound to form an intermediate and (ii) reacting the intermediate from step (i) above with a nucleophile to form a functionalised hydrocarbyl polymer. The functionalised polymers are useful as additives for lubricating oils and fuels.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: September 24, 1996
    Assignee: BP Chemicals Limited
    Inventor: John R. Blackborow
  • Patent number: 5556921
    Abstract: This invention is directed to a fast curing polymer composition which does not require baking or thermosetting to provide a cross-linked coating binder. The composition comprises a polymer which is a homopolymer or copolymer of alpha, beta unsaturated monomers having pendent acetylenic groups which cross-link upon air drying to provide a coating binder.
    Type: Grant
    Filed: February 14, 1994
    Date of Patent: September 17, 1996
    Assignee: Eastern Michigan University
    Inventors: Stoil Dirlikov, Zhao Chen
  • Patent number: 5552503
    Abstract: Applicants have discovered an improved photodefined dielectric materials comprising poly(aromatic diacetylenes). The preferred poly(aromatic diacetylenes) are copolymers of aromatic diacetylenes. Specific examples are 1) a copolymer of 4,4'-diethynyldiphenyl ether and m-diethynyl benzene and 2) a copolymer of 4,4'-diethynyldiphenyl ether and 4,4'-bis(3-ethynylphenoxy)-2,2',3,3',5,5',6,6'-octaflurorbiphenyl. These copolymers can be photochemically crosslinked in patterns with exposure of 30 mJ/cm.sup.2 .mu.m and 60 mJ/cm.sup.2 .mu.m, respectively, and patterns have been produced in 10 .mu.m thick films with features as small as 12 .mu.m.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: September 3, 1996
    Assignee: AT&T Corp.
    Inventors: Elizabeth W. Kwock, Timothy M. Miller
  • Patent number: 5494989
    Abstract: Acetylenic copolymers especially suitable for fabrication of gas and vapor separation membranes are disclosed.
    Type: Grant
    Filed: May 24, 1994
    Date of Patent: February 27, 1996
    Assignee: Bend Research, Inc.
    Inventors: Warren K. Miller, Dwayne T. Friesen
  • Patent number: 5478915
    Abstract: Polyimide oligomers are described which comprise the condensation product of: at least one phenylindane diamine and at least one aromatic bis(ether anhydride). The polyimide oligomers of the invention are readily processed to form solution prepregable polyimide composites having high glass transition temperatures and high temperature and oxidative stability. More particularly, the present invention provides for crosslinkable polyimide oligomers prepared by reacting, in a suitable solvent under an inert atmosphere, a mixture of monomers comprising: (A) an aromatic diamine component comprising from about 25 to 100 mole % of at least one phenylindane diamine; (B) a dianhydride component comprising from about 25 to 100 mole % of at least one aromatic his(ether anhydride); and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and aromatic amines, wherein each end-cap monomer contains at least one crosslinkable functional group in the molecule.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: December 26, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael Amone, Mark R. Southcott
  • Patent number: 5475133
    Abstract: The present invention provides (1) curable bispropargyl-containing monomers represented by the formula: B.sup.1 --A.sup.1.sub.m --R--A.sup.2.sub.n --B.sup.2 wherein R is a radical selected from the group consisting of 1,4-phenylene, 4,4'-biphenyl, 2,6-naphthalene, --C.sub.6 H.sub.4 --CR.sup.2 .dbd.CR.sup.2 --C.sub.6 H.sub.4 -- wherein R.sup.2 is H or CH.sub.3, and the same where said groups contain one or more substituents selected from the group consisting of halo, nitro, lower alkyl, lower alkoxy, fluoroalkyl or fluoroalkoxy, A.sup.1 and A.sup.2 are selected from the group consisting of --C.sub.6 H.sub.4 --C(O)--O-- and --C.sub.6 H.sub.4 --O--C(O)--, m and n are 0 or 1, m+n is 0, 1 or 2, and B.sup.1 and B.sup.2 are --OCH.sub.2 --C.tbd.C--H, (2) thermoset compositions comprised of cured segments derived from monomers represented by the formula: B.sup.1 --A.sup.1.sub.m --R--A.sup.2.sub.n --B.sup.2 as described above, and (3) curable blends of at least two of the monomers.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: December 12, 1995
    Assignee: The Regents of the University of California
    Inventors: Elliot P. Douglas, David A. Langlois, Brian C. Benicewicz
  • Patent number: 5464549
    Abstract: The dispersants are formed by reacting (a) at least one dispersant having at least one primary or secondary amino group and/or at least one hydroxyl group, with (b) at least one polyolefinic compound substituted at each terminal position by a succinic group. Suitable substances for use as reactant (b) include compounds derived from at least one telechelic compound having up to 5000 carbon atoms and at least two terminal methylene groups by reaction with maleic anhydride or the like. The products are deemed to be effective dispersant/detergents for use in fuels and lubricants. In fuels the products are deemed to exhibit the property of inhibiting and/or reducing deposit formation such as intake valve deposits. In crankcase lubricants, the products are deemed to provide desirable viscosity index improving properties.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: November 7, 1995
    Assignee: Ethyl Corporation
    Inventor: John F. Sieberth
  • Patent number: 5461132
    Abstract: An organic magnetic member comprises repetition units represented by the following general formula [I]: ##STR1## having at least one of R.sub.1 and R.sub.2 which is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring, and being spontaneously magnetized.
    Type: Grant
    Filed: March 3, 1994
    Date of Patent: October 24, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masayoshi Tabata, Kazuaki Yokota, Yoko Yoshinaga, Fumio Kishi, Norio Kaneko, Nobuo Kushibiki
  • Patent number: 5444136
    Abstract: Nonlinearly optically active monomer species comprising at least two carbon-carbon activated double bonds, i.e., the polymerization of which is facilitated by the presence of an electron attracting function, and a non-centrosymmetric system of pi (.pi.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: August 22, 1995
    Assignee: Flamel Technologies
    Inventors: Yves Camberlin, Gerard Mignani, Remi Meyrueix, Gilles Tapolsky
  • Patent number: 5442039
    Abstract: Novel polycyanate and polycyanamide compositions containing one or more rodlike mesogenic moieties, when cured, result in products having improved properties.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: August 15, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5437821
    Abstract: Carbon-carbon composites of acceptable shrinkage and with negligible voids re prepared in a single casting step from acetylene-terminated Schiff's base monomers by melting a selected monomer, polymerizing it within a mold to form a green casting, and heating the casting to a carbonizing temperature. Blends of monomers may be used. Graphite may be admixed with the melted monomer to form a slurry before molding. Graphite in the form of woven graphite fiber may alternatively be positioned within the mold before the melted monomer is added thereto.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: August 1, 1995
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Thomas Diberardino, Vincent J. Castelli
  • Patent number: 5428125
    Abstract: Novel polycyanate and polycyanamide compositions containing one or more rodlike mesogenic moieties, when cured, result in products having improved properties.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: June 27, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5412144
    Abstract: The present invention is directed to organic materials that have the ability to double or triple the frequency of light that is directed through the materials. Particularly, the present invention is directed to the compound 4-[4-(2R)-2-cyano-7-(4'-pentyloxy-4-biphenylcarbonyloxy)phenylheptylidene) phenylcarbonyloxy]benzaldehyde, which can double the frequency of light that is directed through the compound. The invention is also directed to the compound (12-hydroxy-5,7-dodecadiynyl) 4'-[(4'-pentyloxy-4-biphenyl)carbonyloxy]-4-biphenylcarboxylate, and its polymeric form. The polymeric form can triple the frequency of light directed through it.
    Type: Grant
    Filed: January 12, 1994
    Date of Patent: May 2, 1995
    Assignee: The Board of Trustees of the Univ. of Illinois
    Inventors: Samuel I. Stupp, Sehwan Son, Hong-Cheu Lin
  • Patent number: 5412065
    Abstract: Polyimide oligomers are described which comprise the intercondensation product of a monomer mixture comprising (A) at least one aromatic bis(ether anhydride), (B) at least one phenylindane diamine, and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and amines, wherein each end-cap monomer (C) contains at least one crosslinkable group in the molecule and wherein the phenylindane diamine component (B) is present in the mixture in a stoichiometric excess. The monomers react in a suitable solvent under an inert atmosphere to form polyimide oligomers having a number average molecular weight of from about 1,000 to about 15,000. The polyimide oligomers of the present invention are readily processed to form polyimide matrix resins with high temperature and oxidative stability.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: May 2, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael Amone, Mark Southcott
  • Patent number: RE36563
    Abstract: There are disclosed a transition metal compound of the general formula RMX.sub.a-1 L.sub.b (R is a .pi. ligand, a fused polycyclic cyclopentadienyl group in which at least one of many-membered rings to which cyclopentadienyl groups are fusedly bonded is a saturated ring, M is a transition metal, X is a .sigma. ligand, L is a Lewis base, a is the valency of M, and b is 0, 1 or 2); a polymerization catalyst for styrene, etc. comprising the above transition metal, preferably further comprising an oxygen atom containing compound ionic compound or organoboron compound and optionally a Lewis base; and a process for producing a polymer of a compound containing an ethylenically unsaturated double bond or an acetylenic polymer, especially a syndiotactic polystyrene by using the above polymerization catalyst. The catalyst is particularly effective for producing highly syndiotactic polystyrene minimized in residual metals amounts at a low cost in enhanced efficiency.
    Type: Grant
    Filed: June 3, 1998
    Date of Patent: February 8, 2000
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventor: Mizutomo Takeuchi