Carboxylic Acid Or Derivative Is A Reactant Patents (Class 528/173)
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Patent number: 5227456Abstract: A melt processable wholly aromatic liquid crystalline polymer capable of forming an anisotropic melt phase at a temperature below approximately 400.degree. C. having enhanced adhesion properties containing from approximately 0.05 to approximately 2.0 mole percent of a recurring sulfonated, ionic moiety in the backbone of the polymer. The polymer is useful for the production of laminate structures.Type: GrantFiled: March 20, 1992Date of Patent: July 13, 1993Assignee: Hoechst Celanese Corp.Inventors: James P. Shepherd, Gerald Farrow, Kurt F. Wissbrun
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Patent number: 5225522Abstract: A multiply-branched aliphatic-aromatic polyester and a method for producing that polymer. The method comprises condensing Z.sup.1 and Z.sup.2 groups of a branching reactant having the general formula Z.sup.1 --Ar--(Z.sup.2)j. In this formula, j is 2 or 3 and Ar is an aryl or heteroaryl group having from 1 to 3, solitary or linked or fused, substituted or unsubstituted, five or six membered rings. One of Z.sup.1 and Z.sup.2 is a group having the ##STR1## general formula in which R.sup.1 is selected from the group consisting of hydroxy, chloro, bromo, monovalent alkoxide having from 1 to about 6 carbons, and --O--(CH.sub.2).sub.d --OH, wherein d is an integer from 1 to 3; and the other is a group having the general formula ##STR2## in which R.sup.2 is a divalent alkyl group having from 1 to about 6 carbon atoms, and g is an integer from 0 to about 100.Type: GrantFiled: July 13, 1992Date of Patent: July 6, 1993Assignee: Eastman Kodak CompanyInventors: S. Richard Turner, Brigitte I. Voit
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Patent number: 5225517Abstract: Polyimides having high glass transition temperature prepared from 2,2-bis(3,4-dicarboxyphenyl) hexafluoropropane dianhydride and 1,5-, 1,6-, 2,6- or 2,7-bis(4-aminophenoxy)napthalene.Type: GrantFiled: October 3, 1991Date of Patent: July 6, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Katherine L. Faron
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Patent number: 5221727Abstract: The new aromatic polyethers containing ester groups, which are distinguished by high dimensional stability, may be used for the production of all kinds of moulded products as well as for the preparation of block copolymers of aromatic polyether segments and segments of other thermoplastic polymers.Type: GrantFiled: February 25, 1991Date of Patent: June 22, 1993Assignee: Bayer AktiengesellschaftInventors: Robert Kumpf, Rolf Wehrmann, Harald Pielartzik, Dittmar Nerger
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Patent number: 5219977Abstract: Tetrapolyimide films derived from oxydiphthalic dianhydride, pyromellitic acid dianhydride, p-phenylene diamine and 4,4'-diaminodiphenyl ether, and their preparation are described. The tetrapolymer films have low water absorption, low coefficients of thermal and hygroscopic expansion, high modulus and are caustic etchable and can be used in flexible printed circuit and tape automated bonding applications.Type: GrantFiled: July 30, 1992Date of Patent: June 15, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: John A. Kreuz
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Patent number: 5218083Abstract: High performance, thermooxidatively stable polyimides are prepared by reacting aromatic diamines with pendant trifluoromethyl groups and dianhydrides in an amide solvent to form a poly(amic acid), followed by cyclizing the poly(amic acid) to form the corresponding polyimide, which has the following general structure: ##STR1##Type: GrantFiled: October 31, 1989Date of Patent: June 8, 1993Assignee: The United States of America as represented by the United States National Aeronautics and Space AdministrationInventors: Margaret K. Gerber, Terry L. St. Clair, J. Richard Pratt, Anne K. St. Clair
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Patent number: 5218077Abstract: A high-temperature stable, highly optically transparent-to-colorless, low dielectric linear aromatic polyimide is prepared by reacting an aromatic diamine with 3,3'bis(3,4-dicarboxyphenoxy)diphenylmethane dianhydride in an amide solvent to form a linear aromatic polyamic acid. This polyamic acid is then cyclized to form the corresponding polyimide, which has the following general structural formula: ##STR1## wherein Ar is any aromatic or substituted aromatic group, and n is 10-100.Type: GrantFiled: August 26, 1991Date of Patent: June 8, 1993Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Anne K. St. Clair, Harold G. Boston, J. Richard Pratt
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Patent number: 5216114Abstract: A method for sulfonating items comprising polybenzazole polymers is described. These sulfonated polybenzazole items are incorporated into composites containing a matrix resin such as an epoxy resin. The interfacial shear strength of these sulfonated polybenzazole fiber-containing composites is significantly improved over the interfacial shear strength of similar composites containing unsulfonated polybenzazole fibers.Type: GrantFiled: February 19, 1991Date of Patent: June 1, 1993Assignee: The Dow Chemical CompanyInventors: William E. Walles, Robert M. Nowak
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Patent number: 5216117Abstract: 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: January 13, 1992Date of Patent: June 1, 1993Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5214122Abstract: A multiply-branched cycloalkyl polyester and a method for producing that polymer. The method comprises condensing Z.sup.1 and Z.sup.2 groups of a branching reactant having the general formula (Z.sup.1)j-CYCLO-(Z.sup.2)k, in which j is 1 or 2, k is 1 or 2, j+k is 3, 4, or 5. CYCLO is selected from the group consisting of non-aromatic ring systems having from 1 to 8, solitary or fused or linked alkyl or heteroalkyl rings. One of Z.sup.1 and Z.sup.2 is a group having the general formula ##STR1## and the other is --OH, --OSi(CH.sub.3).sub.3, or a group having the general formula ##STR2## R.sup.1 is selected from the group consisting of hydroxy, chloro, bromo, monovalent alkoxide having from 1 to about 6 carbons, and --O-- (CH.sub.2).sub.d --OH, wherein d is an integer from 1 to 3. R.sup.2 is a divalent alkyl group having from 1 to about 6 carbon atoms, and g is an integer from 0 to about 100. If CYCLO is a solitary ring then j+k is 3, 4, or 5. If Z.sup.1 is bonded to a linear aliphatic linking group then Z.sup.Type: GrantFiled: July 13, 1992Date of Patent: May 25, 1993Assignee: Eastman Kodak CompanyInventors: S. Richard Turner, Brigitte I. Voit
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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: 5212283Abstract: Linear aromatic polyimides containing the cyclobutene-3,4-dione moiety were produced by reacting 1,2-bis(4-aminoanilino)cyclobutene-3,4-dione with several aromatic dianhydrides. The resulting polymers exhibited glass transition temperatures greater than 500.degree. C., adhered tenaciously to glass, and became more flexible after heating for 1 hour at 300.degree. C.Type: GrantFiled: March 3, 1992Date of Patent: May 18, 1993Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Terry L. St. Clair
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Patent number: 5212277Abstract: The present invention relates to new polyetherimideimides having imideimide group with the following structural formula(I) and inherent viscosity of 0.27.about.0.71 dl/g, which can be made by effecting reaction between an aromatic bis(ether anhydride) and an organic diamine or an aromatic bis(nitro imideimide) and a metal salt of diol.Type: GrantFiled: January 10, 1991Date of Patent: May 18, 1993Assignees: Korea Research Institute of Chemical Technology, Cheil Industries, Inc.Inventors: Kwang-Sup Lee, Kil-Yeong Choi, Jong C. Won, Byoung K. Park, In-Tae Lee
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Patent number: 5212276Abstract: The semicrystalline polyimide prepared by reaction of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA) and 1,3-bis(4-aminophenoxy-4'-benzoyl)benzene (1,3-BABB) is modified so that it can be more readily processed to form adhesive bonds, moldings and composites. The stoichiometric ratio of the two monomers, BTDA and 1,3-BABB is controlled so that the intermediate polyamide acid is of a calculated molecular weight. A polyamide acid with excess anhydride groups is then reacted with the stoichiometrically required amount of monofunctional aromatic or aliphatic amine required for complete endcapping. A polyamide acid with excess amino groups is reacted with the stoichiometrically required amount of monofunctional aromatic anhydride required for complete endcapping. The stoichiometrically offset, endcapped polyimide is processed at lower temperatures and pressures than the unmodified high molecular weight polyimide with the same repeat unit, and exhibits an improved melt stability.Type: GrantFiled: May 8, 1990Date of Patent: May 18, 1993Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Paul M. Hergenrother, Stephen J. Havens, Mark W. Beltz
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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: 5206339Abstract: Polyimide which is obtained by polymerization and consists essentially of recurring structural units of the formula (I): ##STR1## wherein X is a single bond or a hexafluoroisopropylidene group, is processed to a form of pellet, followed by heat-treating to obtain crystallinity of 5% or more, and fed to an extruder to obtain articles.Type: GrantFiled: May 10, 1991Date of Patent: April 27, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masumi Saruwatari, Syoichi Tsuji, Yasuhiro Fujii
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Patent number: 5206340Abstract: Integrated circuit sockets for use in a burn-in test are disclosed. The IC sockets are produced by injection molding of a specific polyimide having an inherent viscosity of 0.35 to 0.65 dl/g and essentially consisting of recurring units represented by the formula (I): ##STR1## wherein X is a radical selected from the group consisting of a bond, divalent hydrocarbon having from 1 to 10 carbon atoms, etc. and R is a tetravalent radical selected from the group consisting of an aliphatic radical having two or more carbon atoms, cycloaliphatic radical, monoaromatic radical etc.Type: GrantFiled: December 19, 1989Date of Patent: April 27, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Toshihiko Tsutsumi, Toshiyuki Nakakura, Taizo Nagahiro, Shuithi Morikawa, Nobuhito Koga
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Patent number: 5202411Abstract: A tri-component polyimide copolymer and the process of preparing the copolymer are disclosed. A mixed reaction medium or solvent system comprising phenol and at least one compound of resorcinol, 1,6-dimethyl phenol and 4-methoxy phenol is used to produce the copolymer by direct imidization without isolating or purifying the imide oligomer as an intermediate.Type: GrantFiled: April 3, 1991Date of Patent: April 13, 1993Assignee: W. R. Grace & Co.-Conn.Inventor: Hiroshi Itatani
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Patent number: 5196500Abstract: Tetrapolyimide films derived from 3,3',4,4'-benzophenone tetracarboxylic dianhydride, pyromellitic acid dianhydride, p-phenylene diamine and 4,4'-diaminodiphenyl ether, and their preparation, are described. The tetrapolymer films have low water absorption, low coefficients of thermal and hygroscopic expansion, high modulus and are caustic etachable and can be used in flexible printed circuit and tape automated bonding applications.Type: GrantFiled: December 17, 1990Date of Patent: March 23, 1993Assignee: E. I. du Pont de Nemours and CompanyInventors: John A. Kreuz, Richard F. Sutton, Jr., Stuart N. Milligan
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Patent number: 5196502Abstract: An improved method for producing multiply-branched polyester comprising condensing a reactant having the general formula Z.sup.1 --Ar--(Z.sup.2).sub.j, wherein j is 2 or 3, Ar is an aryl or heteroaryl group having from 1 to 3, solitary or linked or fused, five or six membered rings, and one of Z.sup.1 and Z.sup.2 is a carboxyl group and the other is a group having the general formula ##STR1## wherein R is an alkyl group having from 1 to 3 carbon atoms, X is selected from the group consisting of fluoro and chloro and g is an integer from 0 to about 7.Type: GrantFiled: November 5, 1991Date of Patent: March 23, 1993Assignee: Eastman Kodak CompanyInventors: S. Richard Turner, Brigitte I. Voit, Ralph B. Nielsen
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Patent number: 5196506Abstract: A polyimide having a high heat-resistance good processability and recurring structural units of the formula (I): ##STR1## wherein R is a tetravalent radical selected from the group consisting of an aliphatic radical having at least two carbon atoms, alicyclic radical, monocyclic aromatic radical, fused polycyclic aromatic radical and polycyclic aromatic radical bonded through a direct bond or a bridge member.Type: GrantFiled: July 15, 1992Date of Patent: March 23, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
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Patent number: 5196505Abstract: A thermoplastically processable aromatic polyamide is prepared by polycondensing diacid monomer A with diamine monomer B: (A) HOOC--Ar--COOH;(B) H.sub.2 N--Ar'--NH.sub.2 ; wherein Ar is 1,3-- or 1,4-phenylene; 1,4--, 1,5--, 2,6-- or 2,7-naphthylene, ##STR1## and Ar' is ##STR2## wherein X is --SO.sub.2 -- or --CO--; Y is --O-- or --S--; Z is --O--, --S--, --SO.sub.2 --, --CO-- or ##STR3## wherein R and R' each is --H or C.sub.1 -- to C.sub.4 -alkyl and n is 0 or 1 in the melt at a temperature in the range of from 200.degree. to 400.degree. C. in the presence of a catalyst selected from the group consisting of alkyl- or aryl-phosphonic acids, -phosphonous acids, -phosphinic acids, esters thereof, halides thereof and mixtures thereof, the catalyst content being 0.01 to 2.0 mol % relative to the total content of components A and B.Type: GrantFiled: December 6, 1990Date of Patent: March 23, 1993Assignee: Huels AktiengesellschaftInventors: Gunter Poll, Jurgen Finke
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Patent number: 5196501Abstract: Preparation of specially substituted aromatic polyamides containing structural units of the formula I mentioned and copolyamides containing at least 10 mol % of structural units of the formula I and structural units of the formula II mentioned and their use as orientation layer in liquid crystal display elements and/or liquid crystal switching elements.Type: GrantFiled: December 17, 1991Date of Patent: March 23, 1993Assignee: Hoechst AktiengesellschaftInventors: Hans-Rolf Dubal, Mikio Murakami, Otto Herrmann-Schonherr, Arnold Schneller
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Patent number: 5191001Abstract: A three-step process for the production of solventless polycarbonate is disclosed. Accordingly, a mixture of two different oligocarbonates each prepared by the interfacial method, is prepared in the first process step. In a second step, the mixture is crystallized. The third step entails polycondensation. In an additional embodiment of the invention the first step uses a mixture of one oligocarbonate with a suitable monomer.Type: GrantFiled: October 10, 1991Date of Patent: March 2, 1993Assignee: Bayer AktiengesellschaftInventors: Steffen Kuhlig, Ralf Pakull, Ulrich Grigo, Peter Tacke, Dieter Freitag, Wolfgang Alewelt
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Patent number: 5189138Abstract: Rigid fluorine-containing compounds, monomers, and polymers based on pentacyclic core systems, such as 12H,14H-5, 7-dioxapentacene with perfluoroalkyl and/or aryl groups in the 12, 14 positions, and 5H,12H-7, 14-dioxapentacene, with perfluoroalkyl and/or aryl groups in the 5,12 positions. These monomers have utility in the preparation of advanced high-performance polymers, particularly polyimides. The rigid pentacyclic core decreases the coefficient of thermal expansion of the polymers, while the fluorinated substituents improve the dielectric constant and water absorption properties. Each monomer unit contains within its pentacyclic core two-O-bridges, and two --CRR.sub.f bridges (where R is aryl, substituted aryl or perfluoroalkyl, and R.sub.f is perfluoroalkyl).Type: GrantFiled: February 20, 1991Date of Patent: February 23, 1993Assignee: E. I. du Pont de Nemours and CompanyInventors: Swiatoslaw Trofimenko, Brian C. Auman
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Patent number: 5177180Abstract: Polyimide intercondensation products are prepared from mixed dianhydrides and aromatic diamines. One of the mixed dianhydrides must be 2,2-bis(3,4-dicarboxyphenyl)-hexafluoropropane dianhydride (6FDA) and the other dianhydride may be oxydiphthalic anhydride (ODPA) or biphenyl dianhydride (BPDA) or mixtures thereof. Preferred aromatic diamines are p-phenylenediamine (PPD) and/or m-phenylenediamine (MPD). The polyimide products have increased glass transition temperatures (Tg), frequently higher than 400.degree. C. Composites made from the polyimides have high thermal and oxidative stability and may be used in aircraft engine hardware.Type: GrantFiled: August 7, 1990Date of Patent: January 5, 1993Assignee: General Electric CompanyInventors: Richard N. Griffin, Robert A. Gray
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Patent number: 5177173Abstract: An aromatic polyestersulfone having improved heat resistance, film-forming property, hydrolysis resistance and mechanical strength which comprises 1 to 100% by mole of recurring units of the general formula: ##STR1## and 99 to 0% by mole of recurring units of the general formula: ##STR2## wherein R and R' are the same or different and each is an alkyl or alkoxyl group having 1 to 4 carbon atoms, Ar is a bivalent aromatic group, and x and y are 0 or an integer of 1 to 4 provided that the sum of x and y is from 1 to 8.Type: GrantFiled: February 27, 1984Date of Patent: January 5, 1993Assignee: Kanegauchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroshi Iwakiri, Masahiro Asada, Kazuya Yonezawa
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Patent number: 5177176Abstract: Polyimide compositions, films, and electronic devices using polyimides, based on 9-aryl-9(perfluoroalkyl)-xanthene-2,3,6,7-dianhydride and one or more diamines from a selected group, which offers to the polyimides a combination of desirable properties including solubility, pseudo rod-like structure, low linear coefficient of thermal expansion, high glass transition temperature, low dielectric constant, and high modulus.Type: GrantFiled: October 29, 1991Date of Patent: January 5, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Brian C. Auman
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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: 5175240Abstract: Aromatic homopolyimide and copolyimide films derived from an aromatic dianhydride and a chlorinated aromatic diamine such as 2-chloro-p-phenylene diamine and 2,2'-dichloro-4,4'-diaminodiphenyl ether are described. The films have low water absorption, high elastic modulus and elongation and can be heat-processed without embrittlement.Type: GrantFiled: December 17, 1990Date of Patent: December 29, 1992Assignee: E.I. Du Pont de Nemours and CompanyInventors: John A. Kreuz, Stuart N. Milligan
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Patent number: 5175241Abstract: Polyimide resins, which have reduced anhydride content when molded, are prepared by a novel reaction process that includes reacting an esterified aromatic tetracarboxylic acid or anhydride monomer with a primary aromatic diamine until substantially no free monomer remains to form a polyamide-acid (the molar ratio of esterified monomer to diamine ranging from 1:1 to 1:2); reacting the polyamide-acid with a low molecular weight end-capping agent to form an end-capped polyamide-acid; and heating the end-capped polyamide-acid to form the polyimide.Type: GrantFiled: December 28, 1989Date of Patent: December 29, 1992Assignee: The Dexter CorporationInventor: David S. Darrow
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Patent number: 5175242Abstract: A new class of soluble phenylated polyimides made from 3,6-diarypyromellitic dianhydride and process for the manufacture of the 3,6-diarypyromellitic dianhydride starting material. The polyimides obtained with said dianhydride are readily soluble in appropriate organic solvents and are distinguished by excellent thermal, electrical and/or mechanical properties making the polyimides ideally suited as coating materials for microelectronic apparatii, as membranes for selective molecular separation or permeation or selective gas separation or permeation, or as reinforcing fibers in molecular composites, or as high modulus, high tensile strength fibers.Type: GrantFiled: February 24, 1989Date of Patent: December 29, 1992Assignee: The University of AkronInventor: Frank W. Harris
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Patent number: 5173561Abstract: The present invention relates to a novel class of aromatic diamine monomers, benzoxazole polymers made from said class of monomers, and polymer-matrix composites which may be produced therefrom. The present invention also relates to methods of producing said polymers and said polymer-matrix composites. The polymer-matrix composites have as one advantage high strength and temperature resistance.Type: GrantFiled: July 24, 1990Date of Patent: December 22, 1992Assignee: Daychem Laboratories, Inc.Inventor: Rakesh K. Gupta
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Patent number: 5171822Abstract: An improved low toxicity polymerization of monomer reactants (PMR) system has 3,4'-oxydianiline as the key monomer reactant. One variation of this system, LaRC-RP46, is prepared by reacting together monomethyl ester or 5-norbornene-2,3-dicarboxylic acid (NE), 3,4'-oxydianiline (3,4'-ODA), and dimethyl ester of 3,3',4,4'-benzophenonetetracarboxylic acid (BTDE); this combination is then treated with heat. This new matrix resin is readily processed into a high quality graphite fiber reinforced composite with excellent reproducibility. The flexibility of the ether linkage in 3,4'-ODA provides high toughness. The composite retains excellent mechanical properties both at 316.degree. C. and at 371.degree. C. The development of LaRC-RP46 will significantly extend the applications of PMR type polyimides.Type: GrantFiled: February 5, 1991Date of Patent: December 15, 1992Assignee: The United States of America as represented by the Administrator of National Aeronautics and Space AdministrationInventor: Ruth H. Pater
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Patent number: 5171828Abstract: Polyimide copolymers are disclosed having the recurring structure ##STR1## wherein AR is AR.sub.1 or AR.sub.2, wherein AR.sub.1 is ##STR2## and wherein AR.sub.2 is ##STR3## provided that the molar ratio of AR.sub.1 to AR.sub.2 is 3:1 to 1:3, and wherein AR.sub.3 is ##STR4## These polyimides have unexpected properties which are useful in various electronic applications.Type: GrantFiled: August 5, 1991Date of Patent: December 15, 1992Assignee: Occidental Chemical CorporationInventors: Timothy A. Meterko, Rudolph F. Mundhenke, Willis T. Schwartz
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Patent number: 5171829Abstract: A copolymeric amphiphilic polyimide precursor having the recurring unit of the formula (1): ##STR1## wherein R.sup.1 is a tetravalent group having at least 2 carbon atoms, R.sup.2 is a bivalent group having at least 2 carbon atoms, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen atom or a monovalent group having 1 to 30 carbon atoms selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an aromatic group, or an alicyclic group, and their groups substituted by a halogen atom, nitro group, amino group, cyano group, methoxy group or acetoxyl group, provided that at least one of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is neither hydrogen atom nor the above-mentioned group which has 1 to 11 carbon atoms; a part of at least one of said R.sup.1 and said R.sup.2 being substituted with a group having a valence different therefrom.Type: GrantFiled: January 16, 1991Date of Patent: December 15, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 5167882Abstract: An improved stereolithography method for building a three-dimensional article including the steps of patternwise curing successive layers of a bath of curable liquid resin formulation until the article has been completely built up, removing the article from the liquid resin bath and then post-curing the article, wherein the liquid resin is a "thiol/nene" formulation including:(a) a first compound having a plurality of norbornene groups thereon;(b) a second compound having a plurality of thiol groups therein; and(c) a free radical photoinitiator,the total functionality of the formulation being greater than 4.Type: GrantFiled: February 5, 1991Date of Patent: December 1, 1992Assignee: Loctite CorporationInventors: Anthony F. Jacobine, Margaret A. Rakas, David M. Glaser
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Patent number: 5166308Abstract: Disclosed is an aromatic copolyimide film prepared by chemical conversion of a copolyamide acid solution obtained by copolymerization of an aromatic tetracarboxylic acid component comprising from 30 to 50 mole % of biphenyltetracarboxylic acid dianhydride, 50 to 70 mole % of pyromellitic acid dianhydride, 60 to 80 mole % of p-phenylenediamine and 20 to 40 mole % of 4,4'-diaminodiphenyl ether. The aromatic copolyimide film has a low coefficient of thermal expansion, low water absorption, a low coefficient of hygroscopic expansion, high mechanical strength and is readily etchable making it suitable for use an advanced electronic substrate.Type: GrantFiled: April 30, 1990Date of Patent: November 24, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: John A. Kreuz, Richard F. Sutton, Jr.
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Patent number: 5162492Abstract: Polyimide prepared from 3,3'4,4'-biphenyltetracarboxylic dianhydride and an aromatic diamine which is at least about 60% meta-phenylene diamine exhibits excellent hydrolytic and oxidative stability.Type: GrantFiled: October 11, 1990Date of Patent: November 10, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mureo Kaku
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Patent number: 5162483Abstract: The invention provides aromatic polyamides having an improved resistance to thermo-oxidation. This is achieved by carrying out the polycondensation in the presence of a catalyst system which comprises a mixture of a phosphorus compound and a tin(II) compound or is a compound which contains both elements. The process according to the invention allows aromatic polyamides to be obtained which are resistant to thermo-oxidation (discoloration).Type: GrantFiled: October 24, 1990Date of Patent: November 10, 1992Assignee: Huels AktiengesellschaftInventors: Gunter Poll, Martin Bartmann, Jurgen Finke
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Patent number: 5159055Abstract: The physical properties of high performance composites can be tailored by using coreactive oligomer blends to make the composites. The blends include a first oligomer having an unsaturated hydrocarbon end cap and a second oligomer having an amine, hydroxyl, sulfhydryl, or ##STR1## functionality. Upon curing, the oligomers homopolymerize (i.e. addition polymerize) and mutually interlink (i.e. copolymerize) to form composites possessing intermediate properties to those exhibited by the pure oligomers. The coreactive oligomer blends may also include noncrosslinking polymers and other coreactants, as desired. Stiffness or toughness can be increased in thermally stable composites without significant loss of other properties through these coreactive oligomer blends that cure to block copolymers.Type: GrantFiled: March 3, 1992Date of Patent: October 27, 1992Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5157018Abstract: Polymers comprising perfluoroalkyl groups, reproduction layers containing these polymers and use thereof for waterless offset printing. The novel perfluoroalkyl group-containing polymers comprise polymers or polycondensates and have, in each case as substituents on different carbon atoms of benzene rings, phenolic OH groups and perfluoroalkyl groups which are optionally attached through intermediate members. In particular, at least 10% of the polymer units carry perfluoroalkyl groups. These polymers are either formed by condensation of substituted phenols (e.g., 4-hydroxybenzoic acid-perfluoroalkyl ester) with an aldehyde, a ketone, or a reactive bismethylene compound or by reacting polymers containing phenolic OH groups (e.g., hydroxypolystyrene) or polycondensates containing reactive OH groups (e.g., phenol-formaldehyde resins) with a perfluoroalkyl group-containing compound (e.g., 2,2-dihydroperfluorodecanoic acid chloride).Type: GrantFiled: February 10, 1992Date of Patent: October 20, 1992Assignee: Hoechst AktiengesellschaftInventor: Werner H. Muller
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Patent number: 5157107Abstract: A polymeric acid is synthesized by the ring-opening poly-addition reaction using a biphenyl tetracarboxylic acid as a tetracarboxylic acid moiety and an aromatic diamine, particularly p-phenylene diamine, as a diamine moiety. An aromatic polyimide resin layer possessing a highly desirable heat-resisting property as a heat-resistant insulating coating material and excelling in adhesive strength relative to a substrate is obtained by adjusting the polymeric acid in viscosity with a suitable organic solvent, applying the resultant polyamic acid on a substrate, and firing the applied layer of the polyamic acid. The substrate, for example, is a conductor layer formed as with copper and used as a multi-layer wiring board for hybrid IC's.Type: GrantFiled: August 29, 1989Date of Patent: October 20, 1992Assignees: Kabushiki Kaisha Toshiba, Toshiba Chemical CorporationInventors: Masaru Nikaido, Hikaru Okunoyama, Katsumi Yanagibashi, Yoshiaki Ouchi
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Patent number: 5157097Abstract: Melt moldable polyamide-imide resins are disclosed which have a glass transition temperature ranging from 120.degree. to 300.degree. C. and have molecule ends blocked with an unsubstituted aromatic group or an aromatic group having a substituent not reactive with amines, isocyanates, carboxylic acids and dicarboxylic acid anhydrides.Type: GrantFiled: August 19, 1991Date of Patent: October 20, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hiroshi Takayanagi, Hirotoshi Katsuoka, Hiromi Nakano, Masumi Ookita, Akihiro Yamaguchi, Masahiko Asano
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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: 5153300Abstract: Aromatic polyester copolymers are provided consisting essentially of dihydroxy-meta-terphenyl units, and bisphenol A units chemically combined with aromatic diacid units such as isophthaloyl units, terephthaloyl units and mixtures thereof. Polyesters have been found to have a high glass transition temperature and stability up to 475.degree. C.Type: GrantFiled: July 17, 1991Date of Patent: October 6, 1992Assignee: General Electric CompanyInventor: Susan A. Nye
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Patent number: 5149761Abstract: The new aromatic ether imides corresponding to the following formula ##STR1## may be used for the production of plastics which in turn may be worked up into moulded articles, films, sheet products and filaments. The plastics produced from the new aromatic ether imides are distinguished by their exceptional dimensional stability under heat.Type: GrantFiled: November 1, 1990Date of Patent: September 22, 1992Assignee: Bayer AktiengesellschaftInventors: Knud Reuter, Dieter Freitag, Gunther Weymans, Rolf Dhein
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Patent number: 5149762Abstract: A silicon-modified thermoplastic resin is prepared by heating a mixture comprised of 10 to 90% by weight of an imide group-containing thermoplastic resin and 90 to 10% by weight of a modified silicon compound having an amino group--NH.sub.2 at one end of the molecule and an alkyl group --C.sub.n H.sub.2n+1 (n is an integer of at least 1) at the other end of the molecule, to chemically bond the imide group-containing thermoplastic resin to the modified silicon compound.Type: GrantFiled: November 8, 1989Date of Patent: September 22, 1992Assignee: Mitsubishi Rayon Company Ltd.Inventors: Yoshio Murashige, Junko Soga
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Patent number: 5147966Abstract: The invention is a novel polyimide prepared from 3,4'-oxydianiline (3,4'-ODA) and 4,4'-oxydiphthalic anhydride (ODPA), in 2-methoxyethyl ether (diglyme). The polymer has been prepared in ultra high molecular weight and in a controlled molecular weight form which has a 2.5 percent offset is stoichiometry (excess diamine) with a 5.0 percent level of phthalic anhydride as an endcap. This controlled molecular weight form allows for greatly improved processing of the polymer for moldings, adhesive bonding, and composite fabrication. The higher molecular weight version affords tougher films and coatings. The overall polymer structure groups in the dianhydride, the diamine, and a metal linkage in the diamine affords adequate flow properties for making this polymer useful as a molding powder, adhesive, and matrix resin.Type: GrantFiled: July 31, 1990Date of Patent: September 15, 1992Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Terry L. St. Clair, Donald J. Progar
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Patent number: 5145943Abstract: Fusible polyimide powders are prepared by the process of this invention. An amic acid amine is first prepared by treating (n+1) moles of a bis(aminophenyl)methane with n mole of aromatic tetracarboxylic anhdride to produce an aromatic amic acid prepolymer. This prepolymer is then mixed with an unsaturated carbocyclic monoanhydride and the mixture heated to form a reactive end-capped polyamic acid precursor. The resulting composition is thermally treated in order to partially imidize the precursor. The resulting fusible polyimide powder is finally separated.Type: GrantFiled: December 17, 1990Date of Patent: September 8, 1992Assignee: Ethyl CorporationInventors: Hsueh M. Li, John Y. Lee