From Monomer Containing An Acetylenic Group Patents (Class 526/285)
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Patent number: 5374701Abstract: Diarylacetylenes and diarylenamines are synthesized from a Schiff's base and an N-arylmethylheterocycle; these compounds are useful as intermediates for a variety of polymers; in particular an efficient process is provided for producing diaryl acetylenes useful in the efficient production of acetylene group-containing polymers which can be cross-linked to produce high strength polymers free of structural defects such as conventionally arise as a result of liberation of volatiles during the cross-linking.Type: GrantFiled: May 4, 1993Date of Patent: December 20, 1994Inventors: Allan S. Hay, Martino Paventi
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Patent number: 5373071Abstract: A process for the polymerization of actylenically unsaturated compounds by contacting the monomer(s) under polymerization conditions with a catalyst system comprising:a) a source of cations of one or more Group VIII metals;b) a bidentate ligand containing phosphorus, arsenic and/or antimony; andc) a source of anions.Type: GrantFiled: June 14, 1993Date of Patent: December 13, 1994Assignee: Shell Oil CompanyInventors: Eit Drent, Dennis H. L. Pello
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Patent number: 5359018Abstract: The present invention relates to a method of controlling the polymerization of acrylates using a catalyst which is selected from at least one of zinc, cadmium, or mercury halides in combination with free iodine to give acrylate polymers having narrow molecular weight distributions, via group transfer polymerization.Type: GrantFiled: January 10, 1994Date of Patent: October 25, 1994Assignee: Dow Corning CorporationInventor: Ming-Hsiung Yeh
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Patent number: 5304583Abstract: This invention relates to production of a super long conjugated polymer to be used for a molecular device, etc. According to this invention, an acetylene derivative is previously oriented and formed into a monomolecular film on the surface of a substrate and its acetylenic group is polymerized by a catalyst or by irradiation of an energy beam while keeping the orientation. Since the respective molecules are oriented and aligned on the substrate surface, the polymerization reaction readily proceeds, and after the polymerization the resulting polyacetylene molecules are prevented from the breakage of conjugated bonds caused by thermal agitation or twisting of the polyacetylene molecules. Accordingly, a polyacetylene or polyacene type polymer having long conjugated bonds can be obtained easily.Type: GrantFiled: October 13, 1992Date of Patent: April 19, 1994Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Kazufumi Ogawa
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Patent number: 5290908Abstract: Aromatic polyimides with acetylenic end groups are cured by coupling together thermally or catalytically using cuprous salts as catalysts to increase molecular weight with little or no by-product formation. These polyimides can be shaped and formed prior to the coupling.The acetylenic end-capped aromatic polyimides are formed by the reaction of an aromatic dianhydride, an acetylenic organic monoamine compound which will provide the reactive end groups and optionally an aromatic diamine.Type: GrantFiled: January 24, 1975Date of Patent: March 1, 1994Assignee: The University of Notre Dame du LacInventor: Gaetano F. D'Alelio
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Patent number: 5286413Abstract: A polymer mixture, including at least one conductive polymer which has been dedoped to provide at least one dedoped conductive polymer; and at least one polar polymer. The polymer mixture has outstanding dielectric properties so that the polymer mixture is useful for producing electronic, optoelectrical, electrical and electromechanical devices.Type: GrantFiled: August 20, 1991Date of Patent: February 15, 1994Assignee: Solvay & Cie (Societe Anonyme)Inventors: Etienne Hannecart, Claude Franquinet
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Patent number: 5281672Abstract: A method for producing acetylide polymers substantially without charring or decomposition comprises heating a mixture comprising an acetylene terminated monomer and a prepolymer of said monomer, resulting in a lower reaction exotherm.Type: GrantFiled: September 10, 1992Date of Patent: January 25, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventor: Thomas Diberardino
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Patent number: 5264511Abstract: Monomers, B-stage polymers, C-stage polymers, cured polymers and electricy conducting polymers of acetylene-terminated aromatic monomers containing three benzene rings separated by ethylene groups are disclosed. These new polymers can withstand aggressive environments and are particularly adapted for use in high temperature composites in addition to the utilization of their electrical conducting properties. Preparation of these materials is accomplished by melt polymerization and heat treatment at high temperatures.Type: GrantFiled: June 30, 1992Date of Patent: November 23, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Theordore R. Walton
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Patent number: 5262515Abstract: A curable fluorine-containing polyimide of the formula: ##STR1## wherein R.sup.1 is a group derived from an aromatic tetracarboxylic acid dianhydride by the removal of two acid anhydride groups,R.sup.2 is a group derived from an aromatic diamine by the removal of two amino groups,A.sup.1 is a residue of the formula: ##STR2## (wherein R.sup.2 is the same as defined above, and Z is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms),A.sup.2 is a residue of the formula: ##STR3## (wherein R.sup.1 and Z are the same as defined above), and n is a number of 0 to 90, and at least one of the groups R.sup.1 and R.sup.Type: GrantFiled: July 10, 1990Date of Patent: November 16, 1993Assignee: Daikin Industries, Ltd.Inventors: Motonobu Kubo, Tsutomu Kobayashi
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Patent number: 5248758Abstract: Compounds containing at least one cyanate group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then cyanating the resulting phenolic functional maleimide.Type: GrantFiled: July 7, 1992Date of Patent: September 28, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5248526Abstract: This invention relates to production of a super long conjugated polymer to be used for a molecular device, etc. According to this invention, an acetylene derivative is previously oriented and formed into a monomolecular film on the surface of a substrate and its acetylenic group is polymerized by a catalyst or by irradiation of an energy beam while keeping the orientation. Since the respective molecules are oriented and aligned on the substrate surface, the polymerization reaction readily proceeds, and after the polymerization the resulting polyacetylene molecules are prevented from the breakage of conjugated bonds caused by thermal agitation or twisting of the polyacetylene molecules. Accordingly, a polyacetylene or polyacene type polymer having long conjugated bonds can be obtained easily.Type: GrantFiled: August 10, 1992Date of Patent: September 28, 1993Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Kazufumi Ogawa
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Patent number: 5248757Abstract: Compounds containing at least one cyanate group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then cyanating the resulting phenolic functional maleimide.Type: GrantFiled: July 7, 1992Date of Patent: September 28, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5248748Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group,(b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b) , which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.Type: GrantFiled: December 19, 1990Date of Patent: September 28, 1993Assignee: Dir. General of Agency of Industrial Science and TechnologyInventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
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Patent number: 5248749Abstract: A homopolymer or a copolymer comprises a polymerizable compound represented by formula (I):A--X--COCOOR.sub.1 (I)whereinR.sub.1 represents a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or an aryl group;X represents an oxygen atom, a sulfur atom, --COO-- or --NR.sub.5 --whereinR.sub.5 is a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group;A represents a C.sub.3 -C.sub.18 alkenyl, alkynyl, alkenylaryl or alkenylaralkyl group, or a group represented by: ##STR1## wherein R.sub.2 and R.sub.3, which may be the same or different, independently represent a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group;Y represents an oxygen atom or --NR.sub.4 -- wherein R.sub.4 represents a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group; n is an integer of 1 to 5; m is an integer of 1 to 10; and l is 0 or an integer of 1 to 20;with the proviso that if Y is present, X is not --NR.sub.5 --. Additionally, disclosed are processes of preparing the homopolymer or copolymer as well as the polymerizable compound.Type: GrantFiled: April 1, 1992Date of Patent: September 28, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Urano Satoshi, Aoki Kei, Tomita Nobuaki, Mori Hirohiko
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Patent number: 5247039Abstract: A method of making silethynyl polymers having units of the general formula--(R.sub.2 SiC.tbd.C)-- wherein each R independently denotes a hydrogen atom, an alkyl, aryl or alkenyl group or a substituted alkyl, aryl or alkenyl group having up to 18 carbon atoms comprises adding a lithium salt of one or more diethynylsilanes of the general formula R.sub.2 Si(C.tbd.CH).sub.2 to one or more dihalosilanes of the general formula R.sub.2 SiX.sub.2 where X is a halogen atom and allowing the components to react. Copolymers with alternating units can be made. Linear polymers are made preferentially. Limiting the use of solvent increases the percentage of linear polymers produced.Type: GrantFiled: February 22, 1993Date of Patent: September 21, 1993Assignee: Dow Corning LimitedInventors: Roberto Bortolin, Scott S. D. Brown, Bhukandas Parbhoo
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Patent number: 5242996Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.Type: GrantFiled: May 22, 1991Date of Patent: September 7, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
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Patent number: 5239046Abstract: Sizing for carbon fibers with uncapped or capped linear polyamideimides.The uncapped linear polyamideimides useful as carbon fiber sizings generally contain repeating units having the general formula: ##STR1## Wherein R.sub.2 =a trivalent organic radical and generally benzenetriyl;R.sub.3 =a divalent organic radical; andn=an integer sufficiently large to provide a strong, tough coating.Useful capped, linear polyamideimide oligomers may be formed by including end caps with an unsaturated functionality (Y) containing a residue selected from the group consisting of: ##STR2## wherein R.sub.1 =lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;j=0, 1, or 2;i=1 or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;T=methallyl or allyl;Me=methyl; andR=hydrogen, lower alkyl, or phenyl.Prepregs and composites having carbon fibers sized with such polyamideimides are also described.Type: GrantFiled: August 24, 1992Date of Patent: August 24, 1993Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson
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Patent number: 5239032Abstract: A heterofunctional macromer represented by the formula: ##STR1## in which R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is a (poly) lactone or (poly) ether chain; X.sub.1 is --COO--, --COOCH.sub.2 CH.sub.2 OCO--, --CONHCOO--, --COOCH.sub.2 CH.sub.2 NH--COO-- or ##STR2## X.sub.2 is --O--, --COO-- or --OCO--NH--R.sub.3 --NHCOO-- group; R.sub.3 is C.sub.1 -C.sub.6 alkylene, aromatic or alicyclic group; A is --CH.sub.2 --, --C(CH.sub.3).sub.2 -- or ##STR3## and reactive polymers derived from said macromer.Type: GrantFiled: December 29, 1992Date of Patent: August 24, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki
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Patent number: 5239031Abstract: A heterofunctional macromer represented by the formula: ##STR1## in which R.sub.1 is H or C.sub.1 -C.sub.4 alkyl; R.sub.2 is a (poly) lactone or (poly) ether chain; X.sub.1 is --COO--, --COOCH.sub.2 CH.sub.2 OCO--, --CONHCOO--, --COOCH.sub.2 CH.sub.2 NH--COO-- ##STR2## X.sub.2 is --O--, --COO-- or --OCO--NH--R.sub.3 --NHCOO--group; R.sub.3 is C.sub.1 -C.sub.6 alkylene, aromatic or alicyclic group; A is --CH.sub.2 --, --C(CH.sub.3).sub.2 -- or ##STR3## and reactive polymers derived from said macromer.Type: GrantFiled: December 29, 1992Date of Patent: August 24, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki
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Patent number: 5232820Abstract: This invention relates to novel thermochromic quaternized polyacetylene salt derivatives which are visually imageable by exposure to a light source generating energy in a wavelength of from about 400 nm to about 1500 nm said salt derivative having a thermosensitivity of at least 50.degree. C. and defined by the formula ##STR1## or a homopolymer thereof wherein X is the N-quaternized monovalent radical of a dye having an optical absorbance in a wavelength of from about 400 nm to about 1500 nm; V is the cationic residue of a carboxyl, sulfonate, thioate, thiolic, thionic or phosphonate radical; n has a value of from 2 to 4 and X' is hydrogen, C.sub.4 to C.sub.25 alkyl, a polar hydrophilic group which promotes hydrogen bonding containing a radical of the group of an amino, amido, hydroxy, ester, ether, phenol, carboxy, halo, sulfonyl, sulfoxy, sulfinyl, silyl, silyoxy, phosphoro, phosphate, keto, carbamate, aldehyde, urea, urethane, a metal salt group or X' is selected from the group defined for X.Type: GrantFiled: March 9, 1992Date of Patent: August 3, 1993Assignee: ISP Investments Inc.Inventors: David F. Lewis, John C. Hornby
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Patent number: 5216102Abstract: The present invention provides a process for producing a polyacetylene.In the present process for producing a polyacetylene, acetylene is polymerized with a Ziegler-Natta catalyst consisting of a trialkylaluminum and an alkyl titanate, wherein there is used, as the trialkylaluminum, a trialkylaluminum having an alkyl group of 6 or more carbon atoms, or, as the alkyl titanate, an alkyl titanate having an alkyl group of 6 or more carbon atoms.The polyacetylene obtained according to the present invention is superior in mechanical properties, particularly stretchability.Type: GrantFiled: September 30, 1991Date of Patent: June 1, 1993Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Mamoru Soga, Shu Hotta, Nobuo Sonoda, Hideki Shirakawa, Kazuo Akagi
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Patent number: 5208306Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.Type: GrantFiled: August 7, 1992Date of Patent: May 4, 1993Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 5206321Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.Type: GrantFiled: October 3, 1991Date of Patent: April 27, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5204415Abstract: Novel dipropargyl ether of alpha, alpha'-bis(4-hydroxyphenyl)-para-diisopropylbenzene is useful in preparing resins having desirable properties as laminates and the like.Type: GrantFiled: November 26, 1991Date of Patent: April 20, 1993Assignee: Shell Oil CompanyInventor: Anthony M. Pigneri
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Patent number: 5198477Abstract: The invention relates to contact lenses made from a polymer comprising macrocycles that are made up of units of formula I--(--CR.sup.1 .dbd.CR.sup.2 --A--)-- (I)wherein A is alkylene or alkenylene each having from 3 to 10 carbon atoms and each of which may be substituted by one or more R.sup.3 radicals, each of R.sup.1 and R.sup.2, independently of the other, is hydrogen or lower alkyl, and R.sup.3 is lower alkyl, fluorinated lower alkyl or a siloxane radical.They exhibit a combination of a high degree of hardness and oxygen permeability. They can be produced in an especially advantageous manner, that is to say by hot compression moulding.Type: GrantFiled: February 25, 1992Date of Patent: March 30, 1993Assignee: Ciba-Geigy CorporationInventors: Harro M. von der Haegen, Bernhard Seiferling
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Patent number: 5196257Abstract: The invention relates to bidimensional organic membranes or diaphragms and to their preparation processes.These diaphragms have at least one monomolecular layer of organic molecules A, such as porphyrins, phthalocyanines and porphyrazines. In a layer, each molecule A is directly or indirectly bonded to n (n.gtoreq.3) identical molecules A by n bonds arranged symmetrically with respect to the center of the molecule A.Therefore there diaphragms have microscopic physical properties identical in at least two directions of the plane of the diaphragm. They can be used as conductive diaphragms.Type: GrantFiled: August 20, 1991Date of Patent: March 23, 1993Assignee: Commissariat a l'Energie AtomiqueInventors: Andre Barraud, Serge Palacin, Florence Porteu, Annie Ruaudel
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Patent number: 5194548Abstract: Disclosed is an organic nonlinear optical material comprising a compound having a conjugate main chain in the molecule and having donor groups D and acceptor groups A added onto the conjugate main chain in the sequence of . . . , D, D, A, A, D, D, . . . , in which the distance between adjacent D's and the distance between adjacent A's are shorter than the distance between adjacent D and A with respect to the distance between the atoms on the main chain to which the respective groups are bonded.In this organic nonlinear optical material, since electron wave functions are modified, enhanced quadratic and cubic nonlinear optical effects can be attained. Accordingly, the organic nonlinear optical material can be advantageously utilized for an electro-optical element and an optical-to-optical element.Type: GrantFiled: January 26, 1990Date of Patent: March 16, 1993Assignee: Fujitsu LimitedInventor: Tetsuzo Yoshimura
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Patent number: 5191047Abstract: Enamine ketone and enonesulfide polymeric solids are prepared by reacting liquid or low-melting propynone terminated enamine ketone and enonesulfide prepolymers in one-step, or more preferably, in two-step processes. Properties of the resulting polymers are determined by the nature of the reactant selected and by the relative amounts of reactants employed. Where the prepolymers formed possess terminal propynone groups, the prepolymers can subsequently be cross-linked. Copolymers can also be formed by reacting the prepolymers of the invention with vinyl-type monomers to form polymers with cross-linked networks. The polymerization techniques disclosed can be employed to produce thermoplastic, thermoset, and elastomeric products, and they are especially useful in reaction injection molding processes, in adhesive systems, in composite formations, for linings, and gaskets which require chemical resistance.Type: GrantFiled: October 21, 1991Date of Patent: March 2, 1993Assignee: Edison Polymer Innovation CorporationInventor: Frank W. Harris
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Patent number: 5189127Abstract: The compound N-(3-ethynylphenyl)maleimide (NEPMI) was used to prepare thermally stable, glassy polyimides which did not exhibit glass transition temperatures below 500.degree. C. NEPMI was blended with the maleimide of methylene dianiline (BMI) and heated to form the polyimide. NEPMI was also mixed with Thermid 600.RTM., a commercially available bisethynyl oligomeric material, and heated to form a thermally stable, glassy polyimide. Lastly, NEPMI was blended with both BMI and Thermid 600.RTM. to form thermally stable, glassy polyimides.Type: GrantFiled: December 3, 1991Date of Patent: February 23, 1993Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Margaret K. Gerber, Terry L. St. Clair
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Patent number: 5189129Abstract: Thermally stable, glassy polymeric materials were prepared from maleimideacetylene terminated monomeric materials by several methods. The monomers were heated to self-polymerize. The A-B structure of the monomer allowed it to polymerize with either bismaleimide monomers/oligomers or bis-acetylene monomers/oligomers. Copolymerization can also take place by mixing bismaleimide and bisacetylene monomers/oligomers with the maleimide-acetylene terminated monomers to yield homogenous glassy polymers.Type: GrantFiled: December 3, 1991Date of Patent: February 23, 1993Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Margaret K. Gerber, Terry L. St. Clair
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Patent number: 5187237Abstract: The epoxy resins according to the invention demonstrate the following structure: ##STR1## The cross-linked epoxy resins exhibit non-linear optical properties.Type: GrantFiled: September 17, 1991Date of Patent: February 16, 1993Assignee: Siemens AktiengesellschaftInventors: Jens Nordmann, Heinz Hacker
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Patent number: 5169896Abstract: A curable composition comprises a compound having at least two hydroxyl groups and a homopolymer or a copolymer of a polymerizable compound represented by formula (I):A--X--COCOOR.sub.1 (I)wherein R.sub.1 represents a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or an aryl group; X represents an oxygen atom, a sulfur atom, --COO-- or --NR.sub.5 -- wherein R.sub.5 is a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group; A represents a C.sub.3 -C.sub.18 alkenyl, alkynyl, alkenylaryl or alkenylaralykyl group, or a group represented by: ##STR1## wherein R.sub.2 and R.sub.3, which may be the same or different, independently represent a hydrogen atom or a C.sub.1 -C.sub.5 alkyl groups; Y represents an oxygen atom or --NR.sub.4 -- wherein R.sub.4 represents a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group; n is an integer of 1 to 5;m is an integer of 1 to 10; and 1 is 0 or an integer of 1 to 20;with the proviso that if Y is present, X is not --NR.sub.5 --.Type: GrantFiled: April 1, 1992Date of Patent: December 8, 1992Assignee: Nippon Paint Co., Ltd.Inventors: Satoshi Urano, Kei Aoki, Nobuaki Tomita, Hirohiko Mori
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Patent number: 5166283Abstract: A polymer having dihydropyridine rings or dihydrotriazine rings as main constitutional units, an ethynyl- or cyanato-terminated Schiff's compound which is a starting material for producing the polymer, and applications of the polymer.Type: GrantFiled: June 14, 1991Date of Patent: November 24, 1992Assignee: Hitachi Ltd.Inventors: Akio Nishikawa, Tohru Koyama, Hideki Asano, Toshikazu Narahara
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Patent number: 5164464Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.Type: GrantFiled: June 7, 1991Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 5164111Abstract: The invention relates to polymerizable liquid-crystal materials and to polymer materials which exhibit liquid-crystal phases and which contain, attached directly or via a spacer, mesogenic groups in which at least one transversely polarizing structural element of the formulae I to X, defined in claim 1, is present.Type: GrantFiled: July 13, 1990Date of Patent: November 17, 1992Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Dieter Dorsch, Rudolf Eidenschink, Andreas Wachtler, Bernhard Rieger, Heino Finkelmann
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Patent number: 5159030Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.Type: GrantFiled: March 25, 1991Date of Patent: October 27, 1992Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 5137964Abstract: This invention relates to novel thermochromic quaternized polyacetylene salt derivatives which are visually imageable by exposure to a light source generating energy in a wavelength of from about 400 nm to about 1500 nm said salt derivatives having a thermosensitivity of at least 50.degree. C. and defined by the formulaXV--C.tbd.C).sub.n X'or a homopolymer thereof wherein X is the N-quaternized monovalent radical of a dye having an optical absorbance in a wavelength of from about 400 nm to about 1500 nm; V is the cationic residue of a carboxyl, sulfonate, thioate, thiolic, thionic or phosphonate radical; n has a value of from 2 to 4 and X' is hydrogen, C.sub.4 to C.sub.25 alkyl, a polar hydrophilic group which promotes hydrogen bonding containing a radical of the group of an amino, amido, hydroxy, ester, ether, phenol, carboxy, halo, sulfonyl, sulfoxy, sulfinyl, silyl, silyoxy, phosphoro, phosphate, keto, carbamate, aldehyde, urea, urethane, a metal salt group or X' is selected from the group defined for X.Type: GrantFiled: March 18, 1991Date of Patent: August 11, 1992Assignee: ISP Investments Inc.Inventors: David F. Lewis, John C. Hornby
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Patent number: 5117044Abstract: The invention provides a polymerizable compound represented by the formula (I):A--X--COCOOR.sub.1wherein A represents a C.sub.1 -C.sub.18 alkenyl, alkynyl, alkenylaryl or alkenylaralkyl group, or a group represented bywherein R.sub.2 and R.sub.3, which are the same or different, represent a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group, Y represents an oxygen atom or --NR.sub.4 --, in which R.sub.4 represents a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group, n is an integer of 1 to 5, m is an integer of 1 to 10 and 1 is 0 or an integer of 1 to 20;R.sub.1 represents a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or an aryl group; andX represents an oxygen atom, a sulfur atom, --COO-- or --NR.sub.5 --, in which R.sub.5 is a hydrogen atom or a C.sub.1 -C.sub.5 alkyl group, provided that if Y is present, X is not --NR.sub.5 --,its production and polymers prepared therefrom.Type: GrantFiled: January 12, 1990Date of Patent: May 26, 1992Assignee: Nippon Paint Co., Ltd.Inventors: Satoshi Urano, Kei Aoki, Nobuaki Tomita, Hirohiko Mori
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Patent number: 5114612Abstract: The present invention provides (1) curable liquid crystalline polyester monomers represented by the formula:R.sup.1 --A.sup.1 --B.sup.1 --A.sup.2 --B.sup.2 --A.sup.3 --R.sup.2where R.sup.1 and R.sup.2 are radicals selected from the group consisting of maleimide, substituted maleimide, nadimide, substituted naimide, ethynyl, and (C(R.sup.3).sub.2).sub.2 where R.sup.3 is hydrogen with the proviso that the two carbon atoms of (C(R.sup.3).sub.2).sub.2 are bound on the aromatic ring of A.sup.1 or A.sup.3 to adjacent carbon atoms, A.sup.1 and A.sup.3 are 1,4-phenylene and the same where said group contains one or more substituents selected from the group consisting of halo, e.g., fluoro, chloro, bromo, or iodo, nitro lower alkyl, e.g., methyl, ethyl, or propyl, alkoxy, e.g., methoxy, ethoxy, or propoxy, and fluoroalkyl, e.g., trifluoromethyl, pentafluoroethyl and the like, A.sup.Type: GrantFiled: January 22, 1991Date of Patent: May 19, 1992Assignee: The United States of America as represented by the Department of EnergyInventors: Brian C. Benicewicz, Andrea E. Hoyt
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Patent number: 5115062Abstract: A polymeric material which exhibits nonlinear optical properties if undoped and conductive properties if doped. The polymer is prepared by polymerizing diethynylsilane compositions, the resulting polymeric material having a weight average molecular weight between about 20,000 and about 200,000 grams per mole. The polymer is prepared and catalytically polymerized by exposure to a catalyst, such as MoCl.sub.5 or W(CO).sub.6 /hv.Type: GrantFiled: October 9, 1990Date of Patent: May 19, 1992Assignee: Iowa State University Research Foundation, Inc.Inventors: Thomas J. Barton, Sina Ijadi-Maghsoodi, Yi Pang
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Patent number: 5104967Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimide oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described.Type: GrantFiled: April 13, 1988Date of Patent: April 14, 1992Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5096987Abstract: Novel dipropargyl ether of alpha, alpha'-bis(4-hydroxyphenyl)-para-diisopropylbenzene is useful in preparing resins having desirable properties as laminates and the like.Type: GrantFiled: October 31, 1990Date of Patent: March 17, 1992Assignee: Shell Oil CompanyInventor: Anthony M. Pigneri
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Patent number: 5091488Abstract: A novel polyethynylacetylene derivative represented by the formula ##STR1## wherein R is H, (C1-7) alkyl, phenyl, benzyl, naphthyl, carbazole, (C2-7) vinyl-alkyl --CX.sub.1 X.sub.2 (OH) or --SiX.sub.1 X.sub.2 X.sub.3 in which X.sub.1, X.sub.2 and X.sub.3 are H, (C1-7) alkyl, phenyl or benzyl, with the proviso that the case where all of X.sub.1, X.sub.2 and X.sub.3 are H is excluded and x is a number of 20 to 500. The polyethynylacetylene derivative is prepared by polymerizing a monomer of the formula HC.tbd.C--C.tbd.CR wherein R is as defined above, with the proviso that the case where R is H is excluded, in the presence of a metathesis catalyst or a Ziegler catalyst. A polyethynylacetylene derivative of the above formula (wherein R=H) is prepared by reacting a polyethynylacetylene derivative of the above formula wherein R=Si(C.sub.n H.sub.2n+1).sub.3 with a desilylating agent. The polyethynylacetylene derivative is soluble in organic solvents and can be shaped into various articles.Type: GrantFiled: December 1, 1989Date of Patent: February 25, 1992Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Masaru Ozaki, Yukihiro Ikeda, Tatsumi Arakawa
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Patent number: 5059666Abstract: Enamine ketone and enonesulfide polymeric solids are prepared by reacting liquid or low-melting propynone terminated enamine ketone and enonesulfide prepolymers in one-step, or more preferably, in two-step processes. Properties of the resulting polymers are determined by the nature of the reactant selected and by the relative amounts of reactants employed. Where the prepolymers formed possess terminal propynone groups, the prepolymers can subsequently be cross-linked. Copolymers can also be formed by reacting the prepolymers of the invention with vinyl-type monomers to form polymers with cross-linked networks. The polymerization techniques disclosed can be employed to produce thermoplastic, thermoset, and elastomeric products, and they are especially useful in reaction injection molding processes, in adhesive systems, in composite formations, for linings, and gaskets which require chemical resistance.Type: GrantFiled: June 6, 1990Date of Patent: October 22, 1991Assignee: Edison Polymer Innovation CorporationInventor: Frank W. Harris
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Patent number: 5055537Abstract: A metal-containing organic polymer produced by the step of polymerizing a compound represented by formula (I):(R--C.tbd.C).sub.l).sub.k k (L) (S).sub.m (I)whereinS represents a hydrogen atom, a hydroxy group, an amino group, a mercapto group, a polyoxyether group, a polyaminoether group, a polythioether group, a sulfino group or a salt thereof, a sulfo group or a salt thereof, a carboxyl group or a salt thereof or a polymerizable group;R represents a metallic atom, a hydrogen atom, or a group --COOM wherein M represents a hydrogen atom or a metallic atom;provided that when R represents a carboxyl group or a hydrogen atom, said compound represented by formula (I) is polymerized in the presence of a metallic salt;L represents a chemical bond or a group having a valency of (k+m); andl, k and m each represents an integer of 1 or more.Type: GrantFiled: March 12, 1990Date of Patent: October 8, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Ken Kawata, Kozo Sato, Masayoshi Tsuboi
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Patent number: 5053462Abstract: A modified polyisobutene has the general formula I ##STR1## where R.sup.1 is an olefinically unsaturated divalent radical, R.sup.2 is one of the radicals --CH.sub.2 --C(.dbd.CH.sub.2)--CH.sub.2 -- or --CH.sub.2 --C(CH.sub.3).dbd.CH-- or m and n are each a degree of polymerization in particular from 1 to 1000.Type: GrantFiled: August 15, 1990Date of Patent: October 1, 1991Assignee: BASF AktiengesellschaftInventors: Dietmar Bender, Klaus Bronstert
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Patent number: 5037916Abstract: A family of ionic polyacetylenes containing long sequences of conjugated double bonds in the backbone with ionic charges adjacent to or in conjugation with the backbone, and a synthetic process for preparing them, are disclosed. These polymers, which are soluble in many solvents, including water, are mono- and di-substituted polyacetylenes that are extensively conjugated. The charge density and geometry of charge distribution depends on the number and nature of the substituents.Type: GrantFiled: March 16, 1990Date of Patent: August 6, 1991Assignee: University of LowellInventors: Alexandre Blumstein, Sundar Subramanyam
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Patent number: 5008040Abstract: A polyacetylene film having a high electroconductivity is prepared by (a) heating a Ziegler-Natta catalyst at a temperature not lower than 150.degree. C. in an organic solvent and then, cooling the catalyst-solvent mixture, (b) removing coarse catalyst particles having a diameter of larger than 1 .mu.m from the catalyst-solvent mixture by filtration to form a catalyst dispersion for polymerization, (c) introducing acetylene into the catalyst dispersion to effect polymerization of acetylene, and (d) drawing the formed polymer and treating the drawn polymer with a dopant.Type: GrantFiled: September 29, 1988Date of Patent: April 16, 1991Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Jun Tsukamoto, Akio Takahashi
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Patent number: 5002707Abstract: Disclosed in a method for producing polydiacetylene of superhigh molecular weight (i.e., a superlong conjugated polymer) having continuous conjugated bands and a straight chain by spreading an organic solvent containing diacetylene derivative on a water surface, gathering up by a barrier, and photopolymerizing the derivative while compressing at a constant surface pressure. Also disclosed is a method for producing polydiacetylene comprising the step of improving the arrangement by applying a direct-current field in a specified direction at the time of spreading and collecting the diacetylene derivative molecules.Type: GrantFiled: July 7, 1988Date of Patent: March 26, 1991Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Kazufumi Ogawa, Hideharu Tamura
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Patent number: RE34820Abstract: Sizing for carbon fibers with uncapped or capped linear polyamideimides.The uncapped linear polyamideimides useful as carbon fiber sizings generally contain repeating units having the general formula: ##STR1## Wherein R.sub.2 =a trivalent organic radical and generally benzenetriyl;R.sub.3 =a divalent organic radical; andn=an integer sufficiently large to provide a strong, tough coating.Useful capped, linear polyamideimide oligomers may be formed by including end caps with an unsaturated functionality (Y) containing a residue selected from the group consisting of: ##STR2## wherein R.sub.1 =lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;j=0, 1 or 2;i=1 or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;T=methallyl or allyl;Me=methyl; andR=hydrogen, lower alkyl, or phenyl.Prepregs and composites having carbon fibers sized with such polyamideimides are also described.Type: GrantFiled: November 15, 1993Date of Patent: January 3, 1995Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson