Carboxylic Acid Or Derivative Is A Reactant Patents (Class 528/173)
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Patent number: 5399655Abstract: This invention concerns positive-working photodefinable polyimide precursors which make use of chemical amplification based on photoacid catalyzed cleavage of acid labile-poly(amic acetal esters).Type: GrantFiled: October 29, 1993Date of Patent: March 21, 1995Assignee: E. I. du Pont de Nemours and CompanyInventor: Howard E. Simmons, III
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Patent number: 5399664Abstract: The invention relates generally to polymers exhibiting second order nonlinear optical properties, and characterized by high thermal stability. Disclosed are polymers prepared by a polycondensation reaction between an aromatic dianhydride and a compound selected from the group consisting of a di(alkylamino)amine and an aromatic diamine. Most preferred are polymers that are the products of a polycondensation reaction between 1,2,4,5-benzenetetracarboxylic dianhydride and nitro(N,N-diethylamino)stilbene, wherein the polymer is imidized by further heat treatment.Type: GrantFiled: November 10, 1993Date of Patent: March 21, 1995Assignee: Arch Development CorporationInventors: Zhonghua Peng, Luping Yu
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Patent number: 5395918Abstract: The invention describes new biphenyl dianhydrides, and new polyimides and copolyimides made from the dianhydrides. The synthesized polyimides exhibit significantly enhanced solubility when the biphenyl dianhydrides are substituted, particularly at the 2 and 2' positions on the phenyl rings.Type: GrantFiled: April 21, 1994Date of Patent: March 7, 1995Assignee: The University of AkronInventors: Frank W. Harris, Sheng-Hsien Lin
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Patent number: 5393864Abstract: A random polyimide copolymer, based on a rigid dianhydride, a rigid diamine and an additional diamine and/or dianhydride containing one or more flexibilizing linkages. Soft-baked coatings of the poly(amic acid) precursor are readily processed using conventional aqueous base developers, such as tetramethylammonium hydroxide. The polyimide and soft-baked coatings are useful as a dielectric layer In multichip module applications or as a stress buffer coating.Type: GrantFiled: April 26, 1993Date of Patent: February 28, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: John D. Summers
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Patent number: 5386002Abstract: Polyetherimides, polyesterimides, poly(ester etherimides) and poly(carbonate imides) which are thermoplastic, polymeric materials contain divalent bisimides of formula ##STR1## wherein R is independently in each occurrence hydrogen, alkyl of from 1 to 20 carbons, aryl or aralkyl of from 1 to 20 carbons, halogen or NO.sub.2. Novel monomeric bisimides corresponding to the above formula are also disclosed.Type: GrantFiled: December 3, 1993Date of Patent: January 31, 1995Assignee: The Dow Chemical CompanyInventors: Muthiah N. Inbasekaran, Daniel J. Murray, Michael N. Mang, James L. Brewbaker
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Patent number: 5384390Abstract: There are disclosed flame-retardant, high temperature resistant polyimide fibers of the general formula ##STR1## wherein n is an integer larger than 1, A is a tetravalent aromatic group and R is at least one divalent aromatic group. These polyimide fibers have been heat-treated in the unstretched state and have a maximum shrinkage of 14% when heated to a temperature of 400.degree. C. These polyimide fibers are produced by initially spinning crude fibers from a solution of the appropriate polyimide in an aprotic organic solvent, preferably according to the dry-spinning method, which solution optionally contains additives. The crude fibers obtained are washed with water to remove the solvent. The washed crude fibers are dried to a moisture content of less than 5% by mass, are subjected to a heat treatment at a temperature of between 315.degree. C and 450.degree. C, are cooled and, if desired, are crimped and cut to staple fibers.Type: GrantFiled: September 23, 1991Date of Patent: January 24, 1995Assignee: Lenzing AktiengesellschaftInventors: Claus Schobesberger, Klaus Weinrotter, Herbert Griesser, Sigrid Seidl
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Patent number: 5380820Abstract: In one aspect, the present invention relates to polyimides having excellent thermal resistance and process for preparing the same comprising carrying out condensation of 4,4'-bis(3-aminophenoxy)biphenyl with pyromellitic dianhydride in the presence of a different diamine compound and optionally with a different tetracarboxylic acid dianhydride.In a second aspect, the present invention relates to a heat resistant resin composition consisting essentially of an aromatic polyetherimide and a defined polyimide.In a third aspect, the present invention relates to a polyimide resin composition comprised on a defined polyimide and a separate high-temperature engineering polymer.In a fourth aspect, the present invention relates to a resin composition comprised of a defined polyimide and an aromatic polyamideimide.Type: GrantFiled: December 7, 1993Date of Patent: January 10, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masahiro Ohta, Masao Yoshikawa
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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: 5374708Abstract: Polyimide filaments and polyimide films having great strength, high elastic modulus and high crystallinity and comprising a novel polyimide which can be melt-processed without impairing high crystallinity and which essentially consists of recurring structural units represented by the formula (I): ##STR1## more than 85 mol % the polyimide consists of recurring structural units of the formula (II): ##STR2## and from 0.5 to 15 mol % of the polyimide consists of recurring structural units represented by the formula (III), the formula (II) exclusive, the formula (IV) and/or the formula (V).Type: GrantFiled: August 8, 1991Date of Patent: December 20, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi, Masumi Saruwatari
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Patent number: 5371168Abstract: Amorphous polyimide powder which has recurring structural units of the formula (I): ##STR1## as a fundamental skeleton, is blocked at the polymer chain end with dicarboxylic anhydride represented by the formula (II) ##STR2## wherein Z is a divalent radical having from 6 to 27 carbon atoms and selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected to each other with a direct bond or a bridge member, and essentially has no reactive radical at the polymer chain end, preparation process of the amorphous polyimide powder, heat-resistant adhesive comprising the polyimide, and bonding method using the adhesive.Type: GrantFiled: June 5, 1992Date of Patent: December 6, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Wataru Yamashita, Shoji Tamai, Akihiro Yamaguchi
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Patent number: 5371173Abstract: The synthesis of a nonlinear chromophoric co-monomer 3,5-diamino-4'-nitrodiphenylamine and use as a reactive component in combination with a bismaleimide monomer in a NLO-active polyimide matrix is disclosed. After concurrent corona or contact poling and thermal polymerization, thin films of these chromophoric polyimides exhibit high second harmonic generation efficiencies and high DSC-determined glass transition temperatures. These poled polyimides also exhibit excellent SHG temporal stability, retaining 85-90% of the initial second harmonic efficiency after more than one month in air at 85.degree. C.Type: GrantFiled: November 25, 1992Date of Patent: December 6, 1994Assignee: Northwestern UniversityInventors: Tobin J. Marks, Michael A. Hubbard, Jiann T. Lin
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Patent number: 5362837Abstract: Macrocyclic polyetherimide oligomer compositions are prepared by a displacement reaction at a temperature in the range of about 200.degree.-225.degree. C. between at least one fluorinated aromatic phthalimide and at least one phenolic trialkylsilyl ether compound. Preferably, a bis-fluoroimide and a bis-trialkylsilyl ether of a dihydroxyaromatic compound such as resorcinol are employed. The reaction is conducted by maintaining reagents A and B in high dilution in a dipolar aprotic organic liquid such as N-methylpyrrolidone, and in the presence of a catalytic amount of at least one substantially soluble fluoride. Preferably, a mixture of reagents A and B is added to solvent containing the catalyst.Type: GrantFiled: July 26, 1993Date of Patent: November 8, 1994Assignee: General Electric CompanyInventors: Tohru Takekoshi, Jane M. Terry
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Patent number: 5357032Abstract: A diamine compound of the general formula ##STR1## wherein the arrows denote isomerism, R.sub.1 is a divalent aromatic group selected from the group consisting of ##STR2## R.sub.2 is a tetravalent aromatic group selected from the group consisting of ##STR3## and R.sub.4 is a monovalent aliphatic group selected from the group consisting of ethyl and isopropyl; and, a process for preparing same.Type: GrantFiled: August 17, 1992Date of Patent: October 18, 1994Assignee: Korea Research Institute of Chemical TechnologyInventors: Suh Bong Rhee, Ji Y. Chang, Bong S. Moon, Ji-Woong Park
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Patent number: 5357031Abstract: An aromatic copolyamide which is soluble in organic copolyamide solvents and contains recurring structural units of formulae I, II and III ##STR1## in which at least some of the radicals R.sup.1 are a group of formula --OC--R.sup.2 --CO--, in which R.sup.2 is a divalent aromatic radical having valence bonds in the para-position or in a comparable coaxial of parallel position to one another, and in which the remaining radicals are as defined.Type: GrantFiled: July 6, 1993Date of Patent: October 18, 1994Assignee: Hoechst AktiengesellschaftInventors: Georg-Emerich Miess, Karl Heinrich, Peter Klein
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Patent number: 5357033Abstract: Film forming aromatic organic polymers are provided having a dielectric constant greater than 3 resulting from the polymerization of aromatic organic monomers having orientable organic dipolar groups with a net dipole moment of at least 0.5 Debye. Among the aromatic organic polymers are included polyimides and polyetherimides having repeat main chain groups with orientable organic dipolar groups with non-symmetrically positioned polar radicals, such as fluoro and nitrile.Type: GrantFiled: April 1, 1993Date of Patent: October 18, 1994Assignee: General Electric CompanyInventors: John T. Bendler, Tohru Takekoshi, Clive W. Reed
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Patent number: 5354839Abstract: A polyimide comprising a requisite structural unit having one or more recurring structural units of the formula: ##STR1## such as the structural units of the formula ##STR2## The polyimide can have an extremely low dielectric constant and is colorless, transparent and excellent in processability and heat resistance, and also provides an aromatic diamine which is useful as a raw material monomer of the polyimide or a raw material of other various engineering plastics.Type: GrantFiled: March 31, 1993Date of Patent: October 11, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Wataru Yamashita, Yoshihiro Sakata, Toshiyuki Kataoka, Yuichi Okawa, Hideaki Oikawa, Tadashi Asanuma, Mitsunori Matsuo, Tsutomu Ishida, Keizaburo Yamaguchi, Akihiro Yamaguchi
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Patent number: 5349039Abstract: Disclosed is a polyester-imide prepared from a condensation polymerization of aromatic diacid, diimide diacid, and diol, having a carboxy to hydroxy equivalent molar ratio of 0.9:1 to 1.1:1. The disclosed polyester-imide has outstanding heat-resistance, remarkable filming ability, and high solubility in both phenol series and amide series solvents.Type: GrantFiled: October 20, 1992Date of Patent: September 20, 1994Assignee: Industrial Technology Research InstituteInventors: Chien-Hui Li, Tzong-Ming Lee, Jyh-Chien Chen
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Patent number: 5346982Abstract: A polyimide-based heat-resistant adhesive having excellent peel strength and heat resistance comprising polyimide composed of 10 to 99% by mole of structural units having the formula (1) and 1 to 90% by mole of structural units having the formula (2) or comprising polyamic acid precursor which corresponds to the polyimide.Type: GrantFiled: June 7, 1993Date of Patent: September 13, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Katsuaki Iiyama, Akihiro Yamaguchi
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Patent number: 5344914Abstract: A new method for preparing commercially valuable polymeric ketones is described. The method employs an .alpha.-amiononitrile as a monomeric unit whereby an amorphous, soluble polymer having protected carbonyl moiety is obtained. Upon deprotecting the carbonyl moiety, a crystalline polymeric ketone is obtained. The method allows production of polymeric ketone materials having aromatic, aliphatic or mixed aromatic/aliphatic backbones.Type: GrantFiled: October 5, 1992Date of Patent: September 6, 1994Assignee: The Center for Innovative Technology*Inventors: Harry W. Gibson, Ashish Pandya
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Patent number: 5344916Abstract: A negative birefringent film, useful in liquid crystal displays, and a method for controlling the negative birefringence of a polyimide film is disclosed which allows the matching of an application to a targeted amount of birefringence by controlling the degree of in-plane orientation of the polyimide by the selection of functional groups within both the diamine and dianhydride segments of the polyimide which affect the polyimide backbone chain rigidity, linearity, and symmetry. The higher the rigidity, linearity and symmetry of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film.Type: GrantFiled: June 4, 1993Date of Patent: September 6, 1994Assignee: The University of AkronInventors: Frank W. Harris, Stephen Z. D. Cheng
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Patent number: 5344910Abstract: Polycarbonate resins containing repeating or recurring polymer chain units of the formula: ##STR1## wherein R represents alkyl are useful in high temperature applications, when thermoplastically molded into articles.Type: GrantFiled: March 23, 1993Date of Patent: September 6, 1994Assignee: General Electric CompanyInventor: Paul D. Sybert
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Patent number: 5342905Abstract: A two step process for the preparation of an ester group-containing polyether sulfone is disclosed. In the first step a dihalogenodiphenyl sulfone is reacted with excess amount of an aromatic dihydroxy compound and in a second step the reaction product is reacted with a dicarboxylic acid derivative. The excess amount of the aromatic dihydroxy compound is that amount which is sufficient to react with said derivative to form the corresponding ester. The process of the invention is characterized by its economics and good yield and by the high purity of the product. The thus produced polyether sulfone is useful as a thermoplastic resin and as a reactant in the melt blending process for the preparation of block copolymers.Type: GrantFiled: January 29, 1993Date of Patent: August 30, 1994Assignee: Miles Inc.Inventors: Robert J. Kumpf, Aaron D. Meltzer, Harald Pielartzik
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Patent number: 5340904Abstract: A compound or polymer having a bis(phenoxy)naphthalene structure, a high molecular weight, and very good mechanical performance and heat-resistivity is provided. The polymer can be polyamides, polyimides or poly(amide-imide)s and can have a basic structure of ##STR1## wherein R1 is a naphthalene ring.Type: GrantFiled: December 29, 1992Date of Patent: August 23, 1994Assignee: National Science CouncilInventors: Chin-Ping Yang, Wen-Tung Chen
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Patent number: 5338821Abstract: Benzofuran-ether-sulphone monomers of formula ##STR1## and ether ketone polymers derived therefrom of formula ##STR2##Type: GrantFiled: April 26, 1993Date of Patent: August 16, 1994Assignee: Raychem LimitedInventor: Ian D. H. Towle
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Patent number: 5338826Abstract: A structure which is effective as an electrical insulator or as a transmitter-receiver of electromagnetic energy is prepared by providing a suitable substrate and covering the substrate with an adhering layer of a low dielectric, high temperature, linear aromatic polyimide.Type: GrantFiled: September 28, 1992Date of Patent: August 16, 1994Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministationInventors: Anne K. St. Clair, Terry L. St. Clair, William P. Winfree
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Patent number: 5334696Abstract: A thermosetting resin is comprised of (a) a bisimide, particularly a bismaleimide, (b) a reactive brominated aromatic compound, particularly a member of the group consisting of group consisting of tribromophenyl maleimide, tribromostyrene, and pentabromobenzyl acrylate; and(c) a multifunctional nitrogen compound, particularly dicyandiamide, and optionally(d) ethylene bistetrabromophthalimide.Type: GrantFiled: December 18, 1992Date of Patent: August 2, 1994Assignee: Allied Signal Inc.Inventors: Larry D. Olson, Jeffrey R. Kamla, Henry R. Johnson
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Patent number: 5334697Abstract: A polyimide gas separation membrane containing repeating units derived from 9,9-disubstituted xanthene dianhydride is disclosed.Type: GrantFiled: October 4, 1993Date of Patent: August 2, 1994Assignee: L'Air Liquide, S.A.Inventor: John W. Simmons
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Patent number: 5332799Abstract: In solutions of polyimide-forming starting materials, containing diamines and tetracarboxylic diesters, at least 2 mol % of the ester groups in the tetracarboxylic diesters are derived from alcohols of the general formulaHO--Z--O--X IorHO--Z--X IIwhere Z is a straight-chain or branched aliphatic radical of from 1 to 15 carbon atoms which can be interrupted by from 1 to 4 ether groups --O-- and X is an aromatic radical of from 5 to 20 carbon atoms which can also contain nitrogen, oxygen or sulfur as hetero atoms in the aromatic ring system, excepting benzyl alcohol as compound of the formula II in the case of the use of diamines having a basicity constant of less than or equal to 10.sup.-11.Type: GrantFiled: November 2, 1992Date of Patent: July 26, 1994Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Rainer Blum, Hans J. Heller, Klaus Lienert
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Patent number: 5328979Abstract: Copolyimide compositions and methods for their preparation which are melt-processible at relative low pressures, i.e. less than 1000 psi, and are suited for laminating and molding, are described. The invention additionally encompasses copolyimide precursors, reinforced polyimide composites and laminates made from said polyimides where the composite is reinforced by fibrous materials. This is achieved by reacting at least one aromatic dianhydride where each anhydride group is located on an aromatic ring with the carbonyl units in an ortho orientation relative to one another, with at least one diamine which is capable of a transmidization reaction upon incorporation into the polyimide backbone, and with at least one other diamine which is not capable of undergoing such reaction, the diamine which is capable of undergoing the transimidization reaction being present in an amount of from about 1-50 mole percent in relation to the diamine that is not susceptable to transimidization.Type: GrantFiled: November 16, 1992Date of Patent: July 12, 1994Assignee: The University of AkronInventors: Frank Harris, Patricia A. Gabori
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Patent number: 5324813Abstract: Low dielectric constant polyimides formed from an optionally fluorinated dianhydride and a fluorinated diamine are described. The fluorine containing constituents are sterically disposed so that the dipole moment of the constituents tend to cancel out. Since fluorine containing diamines are generally nonreactive, to achieve a polyimide of high enough molecular weight to be practically useful, a method of fabrication of a high molecular weight polymer from monomers of low reactivity is provided. The monomers, such as a diamine and dianhydride are provided in a solution within which a low molecular weight polyamic acid is formed. The solution is dried. The polyamic acid used is cured to a low molecular weight polyimide. The polyimide is redisolved, redryed and recured enough times to build up the molecular weight to a useful level. The method is applicable to fabricating other polymers of high molecular weight, such as polyamides, polyesters and polyurethanes.Type: GrantFiled: July 22, 1992Date of Patent: June 28, 1994Assignee: International Business Machines CorporationInventors: Gareth G. Hougham, Jane M. Shaw, Alfred Viehbeck
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Patent number: 5322924Abstract: Addition polyimide resins having improved thermo-oxidative stability and enhanced processability are prepared by the reaction of a mixture of monomers comprising a non-planar polyphenyl diamine (a), a diester of tetracarboxylic acid or the corresponding dianhydride (b) and an end-capping agent (c), or a diamine (d), a non-planar polyphenyl diester or dianhydride of a tetracarboxylic acid (e) and an end-capping agent (c).Type: GrantFiled: October 7, 1991Date of Patent: June 21, 1994Assignee: The United States of America as represented by the United States National Aeronautics and Space AdministrationInventors: Chun-Hua K. Chuang, Raymond D. Vannucci
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Patent number: 5322916Abstract: A polyamide precursor of a polybenzazole polymer is prepared by reacting an aromatic bis(alkenyl)ester with a ring forming, aromatic diamine. The precursor can be prepared in an organic solvent for the monomers to form a soluble polyamide precursor which can be subsequently cyclocondensed to form a PBX polymer. A polybenzoxazole precursor is prepared by the reaction of a bis(alkenyl)ester and a bis(ortho-hydroxyamine). A polybenzazole polymer is easily prepared by heating the polyamide, PBX precursor.Type: GrantFiled: March 16, 1993Date of Patent: June 21, 1994Assignee: The Dow Chemical CompanyInventors: James J. O'Brien, Edmund P. Woo
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Patent number: 5320886Abstract: This invention relates primarily to organofunctional monomers, predominantly dimethacrylates and/or diacrylates containing one or more (predominantly two carboxyl groups, with moieties that provide sufficient affinity with water to allow any desired amount of water and/or miscible fugitive solvents to be mixed homogeneously with these monomers and formulations containing them. The activity of water in the monomer formulations can be adjusted so that it is equal to the water activity in biological tissues. This promotes biocompatibility and enhances the adhesive characteristics of polymers prepared from these formulations. Probability statistics are disclosed that optimize the compositions of polymer reaction products.Type: GrantFiled: November 14, 1991Date of Patent: June 14, 1994Assignee: American Dental Association Health FoundationInventor: Rafael L. Bowen
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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: 5317082Abstract: Polyimide optical waveguide structures comprising a core within a cladding wherein at least one of the core and the cladding is a polyimide containing 6FDA, BTDA, an aromatic diamine having bulky methyl groups ortho to the amine, and a co-diamine wherein the polyimides have the properties of low optical loss, low optical absorbance, controllable refractive index, and high thermal stability, and wherein the polyimides are photosensitive and solvent resistant.Type: GrantFiled: December 22, 1992Date of Patent: May 31, 1994Assignee: Amoco CorporationInventors: Allyson J. Beuhler, David A. Wargowski
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Patent number: 5314988Abstract: A process for forming a polymer (and the polymer formed thereby) for passivation, resist and bonding uses, for example, that is thermally stable at relatively high temperatures in excess of 400.degree. C., but is sensitive to electromagnetic radiation. The process includes forming a heteroatom ring polymer that includes a chain formed of a large number of closed aromatic rings such as polyimide groups. According to the present teaching, intervening moieties, (that is, chemical groupings) in the form of open ring precursors of the aromatic rings, such as polyamic acid groups are introduced between the successive closed aromatic rings, which destroy and/or delimit the colinear character and the coplanar character typical of the successive aromatic rings, thus rendering the aromatic rings sensitive to structural change by electromagnetic radiation exposure, and soluble in common organic solvents, but with the exposed HRP insoluble in resist developers.Type: GrantFiled: July 1, 1991Date of Patent: May 24, 1994Assignee: Academy of Applied Science, Inc.Inventor: James C. W. Chien
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Patent number: 5312896Abstract: The present invention relates to porphyrins and to metal ion-containing monomers and polymers. The monomer ##STR1## wherein A, R.sup.1,R.sup.2,R.sup.3, and R.sup.4 defined herein, is used with dianhydride to produce a porphyrin polymer or a metal ion containing porphyrin polymer. These polymers are useful as electrical conductors and as liquid crystal polymers, non-linear (NLO) materials, magnetic materials, electrochromic polymers photo-and electrocatalysts and advanced materials.Type: GrantFiled: October 9, 1992Date of Patent: May 17, 1994Assignee: SRI InternationalInventors: Tilak R. Bhardwaj, Susanna C. Ventura, Subhash C. Narang
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Patent number: 5312895Abstract: Para-ordered aromatic heterocyclic polymers having repeating units of the formula: ##STR1## wherein n has a value of 0.05 to 1.00 and Q is a benzobisazole of the formula ##STR2## wherein X is --S-- or --O--, are soluble in aprotic solvents.Type: GrantFiled: March 12, 1993Date of Patent: May 17, 1994Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Thuy D. Dang, Fred E. Arnold
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Patent number: 5310863Abstract: Copolyamic acids carrying -CF3 group functionalized aromatic segments in the polymer chain derived from aromatic diamines and dianhydrides with linear-rigid-planar structure interrupted by linear-rigid-noncoplanar segments structure and the corresponding copolyimides films are provided. These copolyimides have low in-plane thermal coefficient of expansion, reduced anisotropy in the optical and dielectric properties, low moisture uptake, and improved polyimide-to-polyimide adhesion.Type: GrantFiled: January 8, 1993Date of Patent: May 10, 1994Assignee: International Business Machines CorporationInventor: Krishna G. Sachdev
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Patent number: 5310856Abstract: A heat-resistant and high-transparence polyesterimide composition is disclosed which is prepared from the reaction of: (a) an imidihydroxycarboxylic acid represented by the following formula: ##STR1## (b) at least one dicarboxylic, such as terephthalic acid or isophthalic acid, or mixture thereof, and (c) at least one dihydroxy compound represented by the following formula: ##STR2## Wherein Y can be --C(CH.sub.3).sub.2 --, --SO.sub.2 --, --CH(CH.sub.3)--, --(CH.sub.2).sub.m --, where m in an integer of 1 to 10, --O--, or --S--; X can be H, Cl, or Br; and n is an integer of 0 to 4. The polyesterimide resins disclosed in this invention also exhibit improved fabricability due to their improved solubility in organic solvents, and improved mechanical strength.Type: GrantFiled: January 11, 1993Date of Patent: May 10, 1994Assignee: Industrial Technology Research InstituteInventor: Chien-Hui Li
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Patent number: 5310862Abstract: A photosensitive polyimide precursor composition containing as main ingredients a poly(amic acid) wherein at least one molecular end is esterified with an alcohol, a compound containing carbon-carbon unsaturation having photoreactivity, and a photopolymerization initiator.The photosensitive polyimide precursor composition of the present invention can be prepared without the formation of any harmful by-product. When film formed from this composition is masked for patterning and then subjected to exposure and development using a developer, the amount of exposed portion dissolved in the developer until unexposed portion is dissolved off by the developer, is small and so it is possible to obtain a thick pattern. Further, by heat-treating this pattern, there can be obtained a thick polyimide pattern.Type: GrantFiled: August 6, 1992Date of Patent: May 10, 1994Assignee: Toray Industries, Inc.Inventors: Hideshi Nomura, Masuichi Eguchi, Masaya Asano
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Patent number: 5306741Abstract: An improved method of laminating a metal foil or sheet to a polyimide material is provided. A solution of a precursor of an intractable (i.e. thermosetting) polyimide is applied to a substrate and the solvent is removed to form a dry tack-free film. Thereafter, a solution of a precursor of a thermoplastic polyimide is applied onto the first film of polyimide and the solvent is removed to form a dry tack-free second film. Both films are then cured concomitantly at a sufficiently rapid rate and low temperature to effect substantial imidization of the polyimide precursors of both films without substantial crosslinking or densification of the polyimides in either of the films. Thereafter, a metal sheet or foil is laminated onto the thermoplastic polyimide film according to the following process. The thermoplastic film is contacted with the sheet or foil of metal to be laminated thereto.Type: GrantFiled: June 23, 1992Date of Patent: April 26, 1994Assignee: International Business Machines CorporationInventors: Pei C. Chen, Thomas E. Kindl, Paul G. Rickerl, Mark J. Schadt, John G. Stephanie
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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: 5304627Abstract: Novel polyimides containing pendent siloxane groups (PISOX) were prepared by the reaction of functionalized siloxane compounds with hydroxy containing polyimides (PIOH). The pendent siloxane groups on the polyimide backbone offer distinct advantages such as lowering the dielectric constant and moisture resistance and enhanced atomic oxygen resistance. The siloxane containing polyimides are potentially useful as protective silicon oxide coatings and are useful for a variety of applications where atomic oxygen resistance is needed.Type: GrantFiled: November 2, 1992Date of Patent: April 19, 1994Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: John W. Connell, Terry L. St. Clair, Paul M. Hergenrother
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Patent number: 5302692Abstract: The diamine, 1,3-diamino-5-pentafluorosulfanylbenzene (DASP), was reacted with various dianhydrides to form polyimides containing an SF.sub.5 moiety. These polyimides exhibit high glass transition temperatures, high density, low solubility, and low dielectric properties. These polymers were used to prepare semi-permeable membranes, wire coatings, and films and are useful for electronic, space and piezoelectric applications.Type: GrantFiled: May 27, 1993Date of Patent: April 12, 1994Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdminstrationInventors: Anna K. St. Clair, Terry L. St. Clair
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Patent number: 5300627Abstract: A silicon-modified, adhesive polyimide film composed mainly of the repetition units of the formula (I) and a process for producing a polyimide film composite product using the above film are provided, the formula (I) being ##STR1## the above process for producing a polyimide film composite product comprising subjecting the above-silicon-modified polyimide film to contact-bonding on heating to a material to be adhered, at an ultimate curing temperature of 130.degree.-230.degree. C.The above polyimide film is highly adhesive and heat-resistant in spite of heating at a relatively low temperature.Type: GrantFiled: September 15, 1992Date of Patent: April 5, 1994Assignee: Chisso CorporationInventors: Kouichi Kunimune, Yoshihiro Soeda, Setsuo Itami, Kazutsune Kikuta
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Patent number: 5300620Abstract: The heat resistant adhesive of the invention comprises polyamic acid and/or polyimide which are prepared by using 1,3-bis(3-aminophenoxy)benzene as an aromatic diamine component and 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride and/or 3,3',4,4'-diphenylethertetracarboxylic dianhydride as tetracarboxylic acid dianhydrides, and further by blocking the polymer chain end with dicarboxylic anhydride or a monoamine compound; or comprises a polyimide solution containing the polyimide in a good solvent.The adhesive of the invention is a heat-resistant adhesive capable of adhering under mild temperature/mild pressure conditions. The adhesive of polyimide solution can provide desired adhesion by simple procedures such as applying to the adherend and heating under pressure and exhibits excellent adhesive strength.Type: GrantFiled: June 22, 1993Date of Patent: April 5, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hideaki Okikawa, Shoji Tamai, Katsuaki Iiyama, Saburo Kawashima, Akihiro Yamaguchi, Tadashi Asanuma
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Patent number: 5298600Abstract: A fluorinated condensation copolyimide has repeating polymer units that include: ##STR1## in which X and Y are diamines. The copolyimide can be made by reacting a 3F-monomer and a 6F-monomer with an aromatic or aliphatic diamine. The 3F-monomer includes 4,4'-(2,2,2-trifluoro-1-phenylethylidene) diphthalic anhydride, a dialkylester of 4,4'-(2,2,2-trifluoro-1-phenylethylidene) diphthalic anhydride, 4,4'-(2,2,2-trifluoro-1-phenylethylidene) diphthalic acid, or mixtures thereof. The 6F-monomer includes 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene] diphthalic anhydride, a dialkylester of 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene] diphthalic anhydride, 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene] diphthalic acid, or mixtures thereof.Type: GrantFiled: December 4, 1992Date of Patent: March 29, 1994Assignee: United Technologies CorporationInventor: Daniel A. Scola
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Patent number: 5298590Abstract: The present invention relates to a liquid crystal alignment treating agent which comprises a polyimide resin prepared from a diamine including an aromatic diamine having at least one linear alkyl group of at least 6 carbon atoms per benzene ring as the essential component and a tetracarboxylic acid and its derivative.The liquid crystal alignment treating agent obtained in accordance with the present invention comprises a polyimide resin having an alkyl group on a side chain, and accordingly provides a liquid crystal-aligned film containing liquid crystal molecules stably having an enhanced inclined alignment angle (tilt angle) to a substrate.Type: GrantFiled: August 13, 1992Date of Patent: March 29, 1994Assignee: Nissan Chemical Industries Ltd.Inventors: Hideyuki Isogai, Toyohiko Abe, Yoshihiro Tsuruoka, Hiroyoshi Fukuro
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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