With Sulfur-containing Reactant Patents (Class 528/226)
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Patent number: 5328981Abstract: A poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resin having improved handling characteristics is prepared by a process comprising preparing in a first enclosed vessel a slurry comprising a solid poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resin and a liquid polar organic compound, and optionally water; then substantially liquifying the resin to form a mixture comprising substantially liquified resin and polar organic compound; then flashing the mixture into a second vessel having a pressure lower than the first vessel, thereby removing a portion of the polar organic compound and solidifying the resin.When the slurry further comprises water, the invention method optionally includes a venting step prior to the substantial liquification of the resin and/or a concentration step after the substantial liquification of the resin.Type: GrantFiled: November 19, 1991Date of Patent: July 12, 1994Inventors: Afif M. Nesheiwat, Jon F. Geibel
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Patent number: 5322922Abstract: Mixtures of salts of organic carboxylic acids and organic compounds of non-salt character, dissolved in a C.sub.1 -C.sub.4 alkanol, can be concentrated or separated with a semipermeable membrane made from a copolyamide or copolyimide-amide which contains (a) a first aromatic diamine radical and (b) a second aromatic diamine radical which carries --SO.sub.3 M groups, where M is H.sup..sym., a monovalent to polyvalent metal cation or an ammonium cation. Provided the first diamine radical contains C.sub.1 -C.sub.4 alkyl groups in the o-positions to the amino groups, the copolymers are radiation-sensitive and can be used for producing protective layers or relief images, development being carried out in an aqueous alkaline medium.Type: GrantFiled: December 3, 1992Date of Patent: June 21, 1994Assignee: Ciba-Geigy CorporationInventors: Joseph Berger, Wolfgang Wernet
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Patent number: 5321096Abstract: A thermoplastic resin composition comprise 99.9.about.50 parts by weight of one or more thermoplastic resin selected from the group consisting of aromatic polyimide, aromatic polyetherimide, aromatic polyamideimide, aromatic polyethersulfone and aromatic polyether ketone and 0.1.about.50 parts by weight of one or more liquid crystal type aromatic polyimide having recurring structural units represented by the formula (1): ##STR1## wherein R.sub.1 .about.R.sub.5 is a hydrogen atom, fluorine atom, trifluoromethyl, methyl, ethyl or cyano and may be the same or different, and R is a tetravalent radical having 6.about.27 carbon atoms and being selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected each other with a direct bond or a bridge member.Type: GrantFiled: March 22, 1993Date of Patent: June 14, 1994Assignee: Mitsui Toatsu Chemical, IncorporatedInventors: Yuichi Okawa, Nobuhito Koga, Hideaki Oikawa, Tadashi Asanuma, Akihiro Yamaguchi
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Patent number: 5312894Abstract: A granular, high-melt-stable poly(arylene thioetherketone) has a solution viscosity (.eta..sub.inh) of at least 0.30 dl/g, a retention (400.degree. C./20 min) of melt crystallization enthalpy (.DELTA.Hmc) of at least 60%, a melting point of 340.degree.-360.degree. C., a glass transition temperature of at least 125.degree. C. and an average particle diameter of 0.1-2 mm. A production process of a granular, high-melt-stable poly(arylene thioether-ketone) comprises reacting an alkali metal sulfide and a dihalogenated aromatic compound consisting principally of a 4,4'-dihalobenzophenone in an organic amide solvent containing water. In the first step, (1) the ratio of the amount of the charged dihalogenated aromatic compound to the amount of the charged alkali metal sulfide is controlled to 0.95-1.2 (mole/mole), (2) the ratio of the water content to the amount of the charged organic amide solvent is controlled to 1-15 (mole/kg), and (3) the reaction is conducted for 3-30 hours at 180.degree.-260.degree. C.Type: GrantFiled: April 27, 1993Date of Patent: May 17, 1994Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yukichika Kawakami, Zenya Shiiki
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Patent number: 5306789Abstract: Amorphous polymers which are soluble in organic solvents and can thus be cast as films have high glass transition temperatures which make them suitable for numerous high temperature applications; the polymers comprise ortho aromatic polyketones, polyphthalazines and polyisoquinolines, the polyphthalazines and polyisoquinolines being readily formed from the polyketones.Type: GrantFiled: October 31, 1990Date of Patent: April 26, 1994Inventors: Allan S. Hay, Rina Singh
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Patent number: 5304626Abstract: A chemical resistant copolymer useful in electronic applications, said copolymer is a polyimide containing a 3,3',4,4'-tetracarboxybiphenyl dianhydride (BPDA) moiety, at least one other dianhydride moiety, and at least one diamine.Type: GrantFiled: September 13, 1991Date of Patent: April 19, 1994Assignee: Amoco CorporationInventors: Marvin J. Burgess, Douglas E. Fjare, Herbert J. Neuhaus
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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: 5266674Abstract: An arylene sulfide copolymer and a process for preparing same by contacting a mixture of two structurally different dihaloromatic compounds, at least one organic amide, at least one sulfur-containing compound, and water, and continuous long fiber reinforced plastics containing arylene sulfide copolymer as the polymer matrix or containing arylene sulfide copolymer in a thermoplastic resin matrix.Type: GrantFiled: December 24, 1990Date of Patent: November 30, 1993Assignee: Phillips Petroleum CompanyInventor: Michael C. Yu
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Patent number: 5264520Abstract: This invention is a process for the preparation of poly(aryl ethers) from cyclic poly(aryl ether) oligomers. These low melt viscosity cyclic oligomers undergo ring opening and chain extension upon heating in the presence of a catalyst, forming high molecular weight linear polymers with no coproduct formation. Finished thermoplastic parts and composites may be prepared using this technology with processing techniques normally restricted to thermosetting monomers.Type: GrantFiled: July 3, 1990Date of Patent: November 23, 1993Assignee: The Dow Chemical CompanyInventors: Michael J. Mullins, Edmund P. Woo
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Patent number: 5264538Abstract: Cyclic poly(aryl ether) oligomers and mixtures thereof, and methods for the preparation thereof in a highly dilute reaction medium under reaction conditions favorable for ring closure at low degrees of polymerization. These oligomers are represented by the general formula ##STR1## where each Y is divalent oxygen or divalent sulfur, each Ar is an aromatic diradical which comprises one or more C.sub.6 to C.sub.20 arylene groups and has at least one electron withdrawing group attached to an aromatic ring, and n is an integer from 1 to about 20 with the proviso that for integer values of n equal to 1 or 2 all linkages between independent aromatic rings comprise at least one atom.Type: GrantFiled: June 27, 1990Date of Patent: November 23, 1993Assignee: The Dow Chemical CompanyInventors: Michael J. Mullins, Edmund P. Woo, Kimberly E. Balon, Daniel J. Murray, Cheng-Cheng C. Chen
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Patent number: 5264176Abstract: An aromatic sulfide/ketone polymer is prepared from a dihaloaromatic ketone, alkali metal sulfide, water and a polar organic compound. The polymerization reaction mixture is subjected to a heat soak at an elevated temperature, then a separation agent is added under controlled conditions and the mixture is subsequently cooled to provide a mixture comprising particulate aromatic sulfide/ketone polymer. Biaxially-oriented film is made from the recovered particles of aromatic sulfide/ketone polymer by (1) washing the polymer particles with an aqueous calcium salt, (2) heating the washed particles to remove water, (3) molding the heated particles to form a sheet of polymer, (4) biaxially stretching the sheet above the glass transition temperature of the polymer to form a film, and (5) heat-setting the biaxially-oriented film under stretching tension for a time and at a temperature to increase strength properties and density.Type: GrantFiled: November 26, 1991Date of Patent: November 23, 1993Assignee: Phillips Petroleum CompanyInventors: Michael D. Cliffton, Jerry O. Reed, Rex L. Bobsein, Jon F. Geibel
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Patent number: 5258440Abstract: Disclosed herein is a resin composition of high heat resistance, comprising 100 parts by weight of at least one arylene thioether ketone polymer and 0.05-30 parts by weight of strontium carbonate.Type: GrantFiled: April 30, 1992Date of Patent: November 2, 1993Assignee: Kureha Kagaku Kogyo K. K.Inventors: Yoshiyuki Inaguma, Ken Kashiwadate, Yoshikatsu Satake
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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: 5239049Abstract: Poly(dianhydride) compounds having formulae (I) and (II): ##STR1## where m is 0 to 50. ##STR2## wherein n is 0 to 20 and X is bond junction, oxygen atom, sulfur atom, SO.sub.2, C(CF.sub.3), CO, C(CH.sub.3).sub.2, CF.sub.2 --O--CF.sub.2, CH.sub.2, and CHOH.Type: GrantFiled: November 23, 1992Date of Patent: August 24, 1993Assignee: Olin CorporationInventors: Bruce A. Marien, Keith O. Wilbourn
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Patent number: 5237046Abstract: The invention relates to a process for stabilizing the molecular weight of high molecular weight, optionally branched polyarylene sulfides prepared by reaction of aromatic dihalogen compounds and, optionally, aromatic trihalogen or tetrahalogen compounds and, optionally, polymer-chain-terminating monomers with alkali metal sulfides and/or alkali metal hydrogen sulfides at elevated temperature in aprotic polar solvents, characterized in that, after the desired molecular weight has been reached, alkali metal sulfides and/or alkali metal hydrogen sulfides present in excess are at least partly reacted with acids to form the alkali metal salts of the acids and hydrogen sulfide.Type: GrantFiled: March 2, 1992Date of Patent: August 17, 1993Assignee: Bayer AktiengesellschaftInventors: Manfred Schmidt, Gabriel Denecker, Wolfgang Jakob, Wolfgang Arlt
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Patent number: 5233018Abstract: A perfluorinated polyimide comprising a repeating unit represented by general formula (1): ##STR1## and a perfluorinated poly(amic acid) comprising a repeating unit represented by general formula (6): ##STR2## wherein R.sub.1 is a tetravalent organic group; and R.sub.2 is a divalent organic group, provided that chemical bonds between carbon atoms and monovalent elements contained in R.sub.1 and R.sub.2 are exclusively carbon-to-fluorine bonds; methods for preparing them; and optical material including the perfluorinated polyimide. 1,4-Bis(3,4-dicarboxytrifluorophenoxy)tetrafluorobenzene dianhydride, 1,4-difluoropyromellitic anhydride, 1,4-bis(3,4-dicarboxytrifluorophenoxy)tetrafluorobenzene, 1,4-difluoropyromellitic acid, and 1,4-bis(3,4-dicyanotrifluorophenoxy)tetrafluorobenzene as well as methods preparing them. The perfluorinated polyimide has a thermal stability and has a low optical loss in an optical communication wavelength region (0.8 to 1.7 .mu.m).Type: GrantFiled: September 26, 1991Date of Patent: August 3, 1993Assignee: Nippon Telegraph and Telephone CorporationInventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
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Patent number: 5232630Abstract: The polymers are prepared by using the new intermediate product which forms a polymeric precursor, and which is converted into the desired heterocyclic polymer by ring closure.Type: GrantFiled: April 17, 1989Date of Patent: August 3, 1993Assignee: U.S. Philips CorporationInventors: Kornelis L. Pouwer, Ton R. Vries, Egbert W. Meijer, Edsko E. Havinga, Hans Wijnberg
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Patent number: 5231160Abstract: A novel aromatic diamine; a polyimide comprising 1,3-bis(3-aminobenzoyl)benzene or 4,4'-bis(3-aminobenzoyl)biphenyl as a diamine component and having recurring structural units represented by the formula (III): ##STR1## wherein R is a tetravalent radical selected from the group consisting of an aliphatic radical having from 2 to 27 carbon atoms, alicyclic radical, monoaromatic radical, condensed polyaromatic radical, and noncondensed aromatic radical connected each other with a direct bond or a bridge member, and X is a divalent radical of ##STR2## and a polyimide having a terminal aromatic group which is essentially unsubstituted or substituted with a radical having no reactivity with amines or dicarboxylic acid anhydrides or a composition comprising said polyimide.Type: GrantFiled: August 29, 1991Date of Patent: July 27, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Keizaburo Yamaguchi, Yuko Ishihara, Saburo Kawashima, Hideaki Oikawa, Toshiyuki Kataoka, Akihiro Yamaguchi
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Patent number: 5227455Abstract: Premix for the production of mouldings, containingA) from 40-99.95% by weight of polymer granules A based on a polyaryl ether sulfone, polyaryl ether ketone, polyimide, polyamide imide or polyether imide, or a mixture thereof,B) up to 50% by weight of fillers B in fiber or particle form, or a mixture thereof,C) from 0.05-10% by weight of a compound C ether of the general formula X ##STR1## where A1 to A7 are identical or different and, independently of one another, are a radical of the formula --CO--, --O--, --S--, --SO.sub.2 --, --C(CH.sub.3).sub.2 --, a chemical bond, ##STR2## and k, l, m, n, p and q are each 0 or 1, or a C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy or cyano derivative thereof which is substituted on the aromatic ring, or of the general formula Y ##STR3## where R is C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy or cyano, A8 to A11 are as defined for A1 to A7, r, s and t are 0 or 1, and x is 2, 3 or 4, or a mixture thereof,is described.Type: GrantFiled: September 4, 1992Date of Patent: July 13, 1993Assignee: BASF AktiengesellschaftInventors: Peter Ittemann, Gerhard Heinz
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Patent number: 5225515Abstract: Polybenzazole polymers may contain perfluorocyclobutane rings to provide a flexible moiety which is stable at high temperatures.Type: GrantFiled: April 17, 1991Date of Patent: July 6, 1993Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, William J. Harris
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Patent number: 5212279Abstract: A hot-melt adhesive comprising a special polyamideimide or polyamide is excellent in heat resistance and adhesive strength and usable for providing substrates for printed circuit boards.Type: GrantFiled: October 22, 1990Date of Patent: May 18, 1993Assignee: Hitachi Chemical Co., Ltd.Inventors: Yoshihiro Nomura, Takashi Morinaga, Toshiaki Fukushima, Hiroshi Minamisawa, Kazuhito Hanabusa
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Patent number: 5212278Abstract: The invention relates to polyarylene ethers which contain, based on the total amount of structural elements present in the polyether resin, 5-100 mol % of a recurring structural element of the formula I ##STR1## and 0-95 mol % of a recurring structural element of the formula II ##STR2## in which X and X' independently of one another are --SO--, --SO.sub.2 -- or --CO--, one of the radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is phenyl or phenyl which is substituted by one to three (C.sub.1 -C.sub.4)alkyl groups and the remaining radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, (C.sub.1 -C.sub.4)alkyl, phenyl or phenyl which is substituted by one to three (C.sub.1 -C.sub.4)alkyl groups, and A is an aromatic radical, at least 25% of the bonds X and/or Y and/or the bridge members contained in A being --SO.sub.2 --.These industrial materials are distinguished by very good mechanical properties and good solubility.Type: GrantFiled: March 13, 1990Date of Patent: May 18, 1993Assignee: Ciba-Geigy CorporationInventors: Rudolf Pfaendner, Thomas Kainmuller, Kurt Hoffmann, Andreas Kramer, Friedrich Stockinger
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Patent number: 5210174Abstract: In a process for the preparation of polyimide by reacting a diamine compound with tetracarboxylic dianhydride in a phenol based solvent, an improved process for reacting the diamine compound with tetracarboxylic dianhydride in a solution by forming separate solutions of the tetracarboxylic dianhydride and the diamine compound and mixing the solutions and/or by dissolving tetracarboxylic dianhydride in the phenol-based solvent containing an organic base.Type: GrantFiled: November 14, 1990Date of Patent: May 11, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoji Tamai, Hideaki Oikawa, Masahiro Ohta, Akihiro Yamaguchi
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Patent number: 5198525Abstract: Aromatic polyether sulfones based on 5 to 90 mol-%, based on total bisphenols, of special dihydroxydiphenyl cycloalkanes and 10 to 95 mol-% based on the bisphenols of specific phthaleins, a process for their production and their use as molding compounds.Type: GrantFiled: May 21, 1990Date of Patent: March 30, 1993Assignee: Bayer AktiengesellschaftInventors: Knud Reuter, Wolfgang Jilge, Bernd Pittel, Gunther Weymans
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Patent number: 5198316Abstract: Mixtures of salts of organic dicarboxylic acids and organic compounds of non-salt character, dissolved in a C.sub.1 -C.sub.4 alkanol, can be concentrated or separated with a semipermeable membrane made from a copolyimide which contains a first aromatic diamine radical (1) and a second aromatic diamine radical (2) which carries --SO.sub.3 M groups, wherein M is H.sym., a mono-to trivalent metal cation or an ammonium cation. The first amine radical (1) and/or the second diamine radical (2) contains C.sub.1 -C.sub.4 alkyl groups in both o-positions to at least one amino group. These copolyamides are also radiation-sensitive (self-crosslinking) and can be used for the production of protective layers or relief images, development being carried out in an aqueous alkaline medium.Type: GrantFiled: June 17, 1992Date of Patent: March 30, 1993Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wernet, Joseph Berger
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Patent number: 5194563Abstract: Linear aromatic polymeric species, particularly oligomers and polymers are produced under mild conditions in good yield by reacting an at least binuclear aromatic compound with an alkylidene bisphenol in the presence of a non C-alkylatable hydroxy substituted aromatic compound effective to stabilize a generated carbonium ion intermediate; the alkylidene bisphenol may be formed in situ from a ketone or aldehyde in the presence of a catalytic amount of a hydroxy substituted aromatic compound effective to generate a carbonium ion with the ketone or aldehyde; carrying out the reaction under reduced pressure, particularly high vacuum permits direct production of high polymers; the oligomers are useful in the manufacture of high molecular weight engineering or industrial plastics; the polymers may be used directly as such plastics.Type: GrantFiled: April 2, 1991Date of Patent: March 16, 1993Inventor: Allan S. Hay
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Patent number: 5194562Abstract: Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rob PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.Type: GrantFiled: January 10, 1992Date of Patent: March 16, 1993Assignee: The Dow Chemical CompanyInventors: Muthiah N. Inbasekaran, Michael J. Mullins
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Patent number: 5175234Abstract: Polyimide oligomers include (1) linear, monofunctional crosslinking oligomers prepared by condensing a monoanhydride end cap with a diamine that includes alternating ether and "Sulfone" (--SO.sub.2 --, --S--, --CO--, --(CF.sub.3).sub.2 C--, or --(CH.sub.3).sub.2 C--) linkages connecting alternating aromatic radicals and with a dianhydride (or dianhydride mixture), particularly the unsaturated, aliphatic dianhydride commonly known as MCTC; (2) linear, mono- or difunctional crosslinking oligomers prepared by condensing an amine end cap with a diamine and a dianhydride; and (3) multidimensional, crosslinking oligomers having an aromatic hub and at least three radiating arms connected to the hub, each arm including a crosslinking end cap at its distal end and at least one imide linkage.Blends, prepregs, and composites can be prepared from the oligomers.Type: GrantFiled: November 7, 1989Date of Patent: December 29, 1992Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5164476Abstract: Soluble and/or fusible polyimides or polyamidoimides of the general formula I ##STR1## in which R denotes a divalent radical of the formula II ##STR2## Ar denotes trivalent or tetravalent aromatic radicals or mixtures thereof, X denotes the amide radical, if Ar is trivalent, and if Ar is tetravalent denotes the imide radical and R.sub.1 denotes divalent aromatic radicals, and a process for their preparation.Type: GrantFiled: June 12, 1990Date of Patent: November 17, 1992Assignee: Chemie Linz Gesellschaft m.b.H.Inventors: Gerd Greber, Heinrich Gruber, Marcel Sychra
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Patent number: 5155206Abstract: The thermooxidative stability and thermomechanical properties of advanced composites which use high performance resin matrices such as polyimides and high strength carbon fibers may be improved by sizing the 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 alkyl, 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.Type: GrantFiled: April 28, 1989Date of Patent: October 13, 1992Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson
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Patent number: 5145940Abstract: Mixtures of salts of organic dicarboxylic acids and organic compounds of non-salt character, dissolved in a C.sub.1 -C.sub.4 alkanol, can be concentrated or separated with a semipermeable membrane made from a copolyimide which contains a first aromatic diamine radical (1) and a second aromatic diamine radical (2) which carries --SO.sub.3 M groups, wherein M is H.sym., a mono- to trivalent metal cation or an ammonium cation. The first amine radical (1) and/or the second diamine radical (2) contains C.sub.1 -C.sub.4 alkyl groups in both o-positions to at least one amino group. These copolyamides are also radiation-sensitive (self-crosslinking) and can be used for the production of protective layers or relief images, development being carried out in an aqueous alkaline medium.Type: GrantFiled: August 12, 1991Date of Patent: September 8, 1992Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wernet, Joseph Berger
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Patent number: 5130411Abstract: An improved process for preparing increased molecular weight polyarylene sulfides is disclosed. The process comprises at least two stages: a first polymerization stage in which a polymer of a relatively low molecular weight is prepared and a second polymerization stage in which the molecular weight is substantially increased. The increased molecular weight permits the polymer to be used in a wide range of molding and shaping applications.Type: GrantFiled: March 6, 1991Date of Patent: July 14, 1992Assignee: Tosoh CorporationInventors: Shinji Tanaka, Hiroshi Inoue
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Patent number: 5126430Abstract: A process for preparing a polyarylene sulfide involves contacting a sulfur source with a metallic salt of an aliphatic .omega.-hydroxycarboxylic acid and a dihalogen aromatic compound in an organic polar solvent, thereby carrying out polycondensation with stability in a polymerization system in which a water content is large. the polyarylene sulfide prepared has a high degree of whiteness and with a sufficiently high molecular weight. The use of the metallic salt of .omega.-hydroxycarboxylic acid in a particular range can provide a novel polyarylene sulfide.Type: GrantFiled: August 1, 1989Date of Patent: June 30, 1992Assignee: Idemitsu Petrochemical Company LimitedInventors: Minoru Senga, Satoshi Ikeuchi
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Patent number: 5116935Abstract: A preferred class of polyimide oligomers include (1) linear, difunctional crosslinking oligomers prepared by condensing an imidophenylamine end cap with a lower alkylene diamine or a polyaryldiamine such as 3,3'-phenoxyphenylsulfone diamine and with a dianhydride, particularly 4,4'-phenoxyphenylsulfone dianhydride; and (2) multidimensional, crosslinking, polyimide oligomers having an aromatic hub and at least two radiating arms connected to the hub, each arm including a crosslinking imidophenylamine end cap at its distal end and at least two imide linkages.Blends, prepregs, and composites can be prepared from the oligomers.Type: GrantFiled: May 18, 1989Date of Patent: May 26, 1992Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard
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Patent number: 5115091Abstract: A novel class of poly(arylene thioether) copolymers which are not only thermoplastic but thermosetting in nature. The copolymer may be prepared by copolymerizing a combination of dihalogenobenzonitrile, dihalogenobenzophenone and thioetherifying agent in a organic solvent.The copolymers are highly resistant to heat and solvents and exhibit excellent mechanical properties at raised temperatures.Type: GrantFiled: July 7, 1989Date of Patent: May 19, 1992Assignee: Tosoh CorporationInventors: Tomoji Tamai, Tetsuya Asahi, Yozo Kondo
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Patent number: 5112941Abstract: An aromatic polyimide separation membrane prepared by subjecting an aromatic polyimide membrane to fluorine treatment with an active fluorine is described. The aromatic polyimide separation membrane according to the present invention has an extremely high selectivity and gas permeability, and therefore, is useful as a membrane for separation of gas mixtures or liquid mixtures.Type: GrantFiled: June 27, 1990Date of Patent: May 12, 1992Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Kasai, Yoshiteru Kobayashi
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Patent number: 5110681Abstract: Disclosed herein is a melt-stable poly(arylene thioether-ketone) prepreg, which comprises in integral combination (A) 20-90 wt. % of a fibrous reinforcing material which comprises long fibers and/or at least one shaped long fiber body, said fibers and/or body being formed of inorganic fibers and/or organic fibers; and (B) 10-80 wt. % of a a thermoplastic matrix material composed principally of a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C/10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree.C./10 min) of at least 210.degree. C. and a reduced viscosity of 0.2-2 dl/g. A melt-stable molded or formed product can also be obtained by shaping the above prepreg or an arrangement or laminate of prepregs of the same type as the above prepreg at 140.degree.-450.degree. C. under stresses.Type: GrantFiled: October 21, 1988Date of Patent: May 5, 1992Assignee: Kureha Kagaku Kogyo K. K.Inventors: Yoshikatsu Satake, Ken Kashiwadate, Yasuo Sakaguchi, Takayuki Katto, Zenya Shiiki
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Patent number: 5109102Abstract: This invention relates to making an arylene sulfide ketone polymer. In accordance with this invention, a diahloaromatic ketone, a polar organic compound, and an alkali metal sulfide are mixed together to form a first reaction mixture. This first reaction mixture is subjected to a first set of polymerization conditions effective to produce a polymerization mixture. This polymerization mixture is then dehydrated to form a dehydrated polymerization mixture. Additional dihaloaromatic ketone and polar organic compound is then mixed with the dehydrated polymerization mixture to form a second reaction mixture. This second reaction mixture is then subjected to a second set of polymerization conditions such that an arylene sulfide ketone polymer is formed.Type: GrantFiled: October 31, 1990Date of Patent: April 28, 1992Assignee: Phillips Petroleum CompanyInventor: Jon F. Geibel
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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: 5098990Abstract: A new process for making polyesters, polyamides and polyketones which comprises reacting a dihydric alcohol, a diamine or a diacylaromatic compound with a bis(trichloromethylketone) compound and in the presence of a basic catalyst, as necessary.Type: GrantFiled: September 23, 1987Date of Patent: March 24, 1992Assignee: The Dow Chemical CompanyInventor: Marlin E. Walters
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Patent number: 5097003Abstract: A process for producing a polyphenylene sulfide ketone polymer comprising reacting a dihalogen compound of the general formula ##STR1## wherein X and X', which may be the same or different, each represents a fluorine, chlorine, bromine or iodine atom, with an alkali metal sulfide in a polar solvent in such a way that the alkali metal sulfide is not deprived of free water or the water of hydration in the polar solvent before polymerization is started, and that the reaction is performed at a temperature in the range of from 80.degree. to 170.degree. C. in the initial period of polymerization until the percentage of residual unreacted dihalogen compound is reduced to 2% or below, with the subsequent reaction being performed at a temperature in the range of from 200.degree. to 345.degree. C.Type: GrantFiled: June 7, 1989Date of Patent: March 17, 1992Assignee: Tosoh CorporationInventors: Satoshi Tomagou, Toshikazu Kato, Kensuke Ogawara
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Patent number: 5093467Abstract: An improved process for producing poly(arylene sulfide sulfone) of increased molecular weight is provided. The process employs an Li salt of C.sub.1 -C.sub.20 carboxylic acid as a polymerization auxiliary and is carried out in an organic amide solvent by reacting a dihalogenated aromatic sulfone with an alkali metal sulfide in the presence of 10-15 moles of water per mole of the alkali metal sulfide at temperatures within the range of from 160.degree. C. to 230.degree. C.Type: GrantFiled: June 22, 1989Date of Patent: March 3, 1992Assignee: Tosoh CorporationInventors: Takehiko Sakane, Toshikazu Kato, Kensuke Ogawara
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Patent number: 5093468Abstract: The invention relates to high molecular weight, substantially linear copolyarylene sulfides predominantly containing biphenylene sulfide units, which are produced by reaction of aromatic halogen compounds and halobiphenylenes with sulfur donors in dipolar aprotic solvents, and to their use for moldings, films and fibers exposed to high temperatures and--preferably in reinforced form--as injection molding compounds.Type: GrantFiled: September 4, 1990Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventor: Karl-Heinz Kohler
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Patent number: 5091509Abstract: A poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resin having improved handling characteristics is prepared by a process comprising preparing in a first enclosed vessel a slurry comprising a solid poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resin and a liquid polar organic compound, and optionally water; then substantially liquifying the resin to form a mixture comprising substantially liquified resin and polar organic compound; then flashing the mixture into a second vessel having a pressure lower than the first vessel, thereby removing a portion of the polar organic compound and solidifying the resin.When the slurry further comprises water, the invention method optionally includes a venting step prior to the substantial liquification of the resin and/or a concentration step after the substantial liquification of the resin.Type: GrantFiled: December 29, 1989Date of Patent: February 25, 1992Assignee: Phillips Petroleum CompanyInventors: Afif M. Nesheiwat, Jon F. Geibel
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Patent number: 5091502Abstract: The present invention relates to a tetraketone of the structure ##STR1##wherein M is a metal atom and R is selected from phenyl, alkyl substituted phenyl or halogen substituted phenyl. The process to prepare this tetraketone is disclosed. The present invention also relates to a process to produce the tetraketone structure(I). The present invention also relates to the novel polymer of the structure: ##STR2##and to the process to produce this novel polymer. R is as defined hereinabove, and Ar is a tetraamine substituted organic moiety having at least one aromatic ring. These polymers are useful as liquid crystals and in non-linear optical devices.Type: GrantFiled: March 12, 1990Date of Patent: February 25, 1992Assignee: General Petrochemical Industries LtdInventors: Subhash C. Narang, Susanna Ventura, Tilak R. Bhardwaj
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Patent number: 5091500Abstract: Polybenzazole polymers contain perfluorocyclobutane rings to provide a flexible moiety which is stable at high temperatures.Type: GrantFiled: September 21, 1990Date of Patent: February 25, 1992Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, William J. Harris
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Patent number: 5089596Abstract: Aromatic sulfide/ketone polymer is prepared from dihaloaromatic ketone, alkali metal sulfide, water and a polar organic compound. The polymerization reaction mixture comprising the aromatic sulfide/ketone polymer is subjected to a heat soak at elevated temperature then a separation agent (non-solvent) is added under controlled conditions and subsequently cooled to provide a mixture comprising particulate aromatic sulfide/ketone polymer.Type: GrantFiled: May 22, 1990Date of Patent: February 18, 1992Assignee: Phillips Petroleum CompanyInventors: Michael D. Cliffton, Jerry O. Reed, Rex L. Bobsein, Jon F. Geibel
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Patent number: 5089597Abstract: The invention is a process to provide more granular, higher bulk density particulate poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resins having associated therewith improved handling.The process for treating a first slurry comprising a solid particulate poly(arylene sulfide ketone) or poly(arylene sulfide diketone) resin dispersed in a liquid medium comprising a polar organic compound, comprises: (a) liquifying the first solid particulate resin in the first slurry to form a first mixture comprising a liquified resin and the polar organic compound; (b) adding, to the first mixture, a sufficient amount of at least one separaton agent to produce a second mixture, and (c) reducing the temperature of the second mixture sufficiently to solidify the liquified resin to form a second slurry comprising a polar organic compound and a second solid particulate resin having a bulk density greater than the first solid particulate resin would if recovered.Type: GrantFiled: December 29, 1989Date of Patent: February 18, 1992Assignee: Phillips Petroleum CompanyInventors: Afif M. Nesheiwat, John E. Geibel
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Patent number: 5081214Abstract: A process for the preparation of an aromatic polyether by condensation of dihydric phenols with activated aromatic dihalo compounds or by self-condensation of polynuclear activated halophenols employs a mixture of sodium carbonate and sodium hydrogen carbonate as a condensation auxiliary.By this means, the relatively low reactivity of the sodium carbonate is enhanced and the reaction rate is significantly increased.Type: GrantFiled: August 7, 1990Date of Patent: January 14, 1992Assignee: Hoechst AktiengesellschaftInventor: Arnold Schneller
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Patent number: 5077380Abstract: Compounds containing at least one cyanate group, at least one maleimide group and at least one mesogenic or rodlike moiety are prepared by reacting one or more aminophenols containing one or more mesogenic or rodlike moieties with a stoichimetric quantity of a maleic anhydride per amine group of said aminophenol and then cyanating the resulting phenolic functional maleimide.Type: GrantFiled: October 11, 1990Date of Patent: December 31, 1991Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls