Halogen-containing Material Is A Reactant Patents (Class 528/174)
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Patent number: 5516875Abstract: 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: December 15, 1994Date of Patent: May 14, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Howard E. Simmons, III
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Patent number: 5516566Abstract: Low molecular weight cyclic oligomers of formula (I) ##STR1## in which n is an integer of 2 to 20, and each C in the oligomer is a radical of formula (II): ##STR2## and each X in the oligomer is --O--R--O-- or --S--R--S--, B and D are both carbonyl groups CO, or together represent a divalent radical of formula ##STR3## in which A.sub.1, A.sub.2, A.sub.3 A.sub.4, Ar.sub.1, Ar.sub.2 and Ar.sub.3 are selected from a variety of aromatic radicals, A.sub.1, A.sub.2, Ar.sub.3 and Ar.sub.4 also possibly being hydrogen, are useful in the production of high molecular weight, linear, polyketones, polyphthalazines and polyisoquinolines; the cyclic oligomers have low melt viscosities when heated above their softening temperatures and can be readily molded, whereafter they can be ring-open polymerized to form molded high molecular weight polymer products with excellent properties.Type: GrantFiled: January 3, 1995Date of Patent: May 14, 1996Inventors: Allan S. Hay, Kwok P. Chan
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Patent number: 5508377Abstract: This invention relates to a novel polyimide or polyimide copolymer having excellent heat resistance and greatly improved processability, and has a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the polyimide or polyimide copolymer and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition.The polyimide comprise a requisite structural unit having one or more recurring structural units of the formula: ##STR1## wherein L is an oxygen atom, carbonyl, isopropylidene or hexafluoroisopropylidene, and X is ##STR2## and Ar is a tetravalent radical having 6 to 27 carbon atoms and being selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed polyaromatic radical having aromatic radicals connected to each other with a direct bond or a bridge member.Type: GrantFiled: December 13, 1994Date of Patent: April 16, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Wataru Yamashita, Yuichi Okawa, Shoji Tamai, Akihiro Yamaguchi
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Patent number: 5500479Abstract: A block copolymer resin containing structural units conforming to ##STR1## and a method for its preparation are disclosed. Accordingly, the block copolymer is prepared by reactive blending of an ester-containing polyether sulfone with a polyester. The block copolymer resin thus produced is characterized by its homogeneous morphology. The high level of its mechanical properties makes the resin suitable for a variety of applications.Type: GrantFiled: September 23, 1994Date of Patent: March 19, 1996Assignees: Bayer Corporation, Bayer AktiengesellschaftInventors: Aaron D. Meltzer, Alexander Karbach
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Patent number: 5498691Abstract: Disclosed are bis-meta-benzotrifluoride compounds having the general formula ##STR1## where each A is independently selected from the group consisting of NO.sub.2, NH.sub.2, and NH.sub.3.sup.+ Z.sup.-, Z.sup.- is an anion and B is selected from the group consisting of O, CO, S, SO, and SO.sub.2. The diamine compounds are useful as monomers in making polyimides, polyamide-imides, and polyamides.Type: GrantFiled: October 9, 1990Date of Patent: March 12, 1996Assignee: Occidental Chemical CorporationInventors: Jeffrey S. Stults, Henry C. Lin, Robert A. Buchanan, Robert L. Ostrozynski
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Patent number: 5496915Abstract: Polyimides are obtainable by reacting a dianhydride component with a diamine component, at least one diamine containing cycloaliphatic units, with the proviso that the dianhydride component is a mixture of different dianhydrides if the diamine component consists only of one diamine containing cycloaliphatic units and the diamine component is a mixture of different diamines if the dianhydride component consists of only one dianhydride.Type: GrantFiled: February 13, 1995Date of Patent: March 5, 1996Assignee: BASF AktiengesellschaftInventors: Christian Fischer, Karin Elbl-Weiser, Ju/ rgen Koch
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Patent number: 5484879Abstract: Polyimide polymers of the following recurring structure and the corresponding polyamic acids are disclosed: ##STR1## wherein AR.sub.1 is ##STR2## where X is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2, or a single bond, wherein AR.sub.2 may be pyromellitic dianhydride, a substituted pyromellitic dianhydride, naphthanoic dianhydride, or ##STR3## where Y is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2 --O--AR--O--, or a single bond, where AR is an aromatic nucleus.Type: GrantFiled: December 17, 1990Date of Patent: January 16, 1996Assignee: Occidental Chemical CorporationInventors: Robert A. Buchanan, Jeffrey S. Stults, Ronald F. Spohn
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Patent number: 5484880Abstract: The present invention relates to an amorphous polyimide or a polyimide copolymer having a requisite structural unit consisting of one or more recurring structural units represented by the formula (1): ##STR1## wherein X is a direct bond, oxygen atom or sulfur atom, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are individually a hydrogen atom or methyl, and Ar is a tetravalent radical having 6 to 27 carbon atoms and being selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed polyaromatic radical having aromatic radicals connected to each other with a direct bond or a bridge member.Polyimide and the polyimide copolymer of the invention has excellent heat resistance, is outstanding in melt-flow stability, has greatly improved processability, and can be applied to structural materials, and electric- electronic appliances.Type: GrantFiled: December 13, 1994Date of Patent: January 16, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Wataru Yamashita, Yuichi Okawa, Shoji Tamai, Mitsunori Matsuo, Tsutomu Ishida, Keizaburo Yamaguchi, Akihiro Yamaguchi
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Patent number: 5480965Abstract: This invention relates to a novel thermoplastic and amorphous polyimide which is readily soluble in organic solvent, a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the thermoplastic polyimide and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition, a polyimide-based composite obtained by molding the above soluble and thermoplastic polyimide in combination with a fibrous reinforcement, and a fibrous reinforcement having a surface modified with the above polyimide.Type: GrantFiled: July 26, 1994Date of Patent: January 2, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Wataru Yamashita, Yuichi Okawa, Hideaki Oikawa, Tadashi Asanuma, Yuko Ishihara, Mitsunori Matsuo, Keizaburo Yamaguchi, Akihiro Yamaguchi, Shoji Tamai
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Patent number: 5480964Abstract: 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: April 21, 1994Date of Patent: January 2, 1996Assignee: The University of AkronInventors: Frank W. Harris, Stephen Z. D. Cheng
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Patent number: 5478915Abstract: Polyimide oligomers are described which comprise the condensation product of: at least one phenylindane diamine and at least one aromatic bis(ether anhydride). The polyimide oligomers of the invention are readily processed to form solution prepregable polyimide composites having high glass transition temperatures and high temperature and oxidative stability. More particularly, the present invention provides for crosslinkable polyimide oligomers prepared by reacting, in a suitable solvent under an inert atmosphere, a mixture of monomers comprising: (A) an aromatic diamine component comprising from about 25 to 100 mole % of at least one phenylindane diamine; (B) a dianhydride component comprising from about 25 to 100 mole % of at least one aromatic his(ether anhydride); and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and aromatic amines, wherein each end-cap monomer contains at least one crosslinkable functional group in the molecule.Type: GrantFiled: December 30, 1993Date of Patent: December 26, 1995Assignee: Ciba-Geigy CorporationInventors: Michael Amone, Mark R. Southcott
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Patent number: 5478918Abstract: A polyimide precursor composition solution includes a tetracarboxylic acid component containing not less than 70 mol % of at least one selected from the group consisting of benzenetetracarboxylic acid and its reactive derivatives; a maleimide compound; and a diamine component containing not less than 70 mol % of 2,2'-substituted-4,4'-benzidine represented by the general formula (I) and siloxydiamine amounting to from 1 to 10 mol %. The tetracarboxylic acid component, the maleimide compound and the diamine component are dissolved in a solvent which is consisting essentially of .gamma.-butyrolactone. The amount of the tetracarboxylic acid component is substantially equivalent to that of the diamine component. The amount of the maleimide compound is from 5 to 30 wt % of the total weight of the tetracarboxylic acid and the diamine component.Type: GrantFiled: February 1, 1994Date of Patent: December 26, 1995Assignee: Central Glass Company, LimitedInventors: Masamichi Maruta, Hidehisa Nanai, Yoshihiro Moroi, Hiroshi Takahashi, Seiji Hasegawa
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Patent number: 5475079Abstract: A (co)polycarbonate composition mainly comprising a (co)polycarbonate having a limiting viscosity number [.eta.] of 0.2 to 1.0 dl/g and terminal hydroxyl groups in an amount of 20 mole % or below, based on all the terminal groups of the (co)polycarbonate, and is substantially free from any branched structure which might otherwise be formed by a side reaction. The (co)polycarbonate contains chlorine (causasive of discoloration) in an amount of 10 ppm or below and an alkali metal ion and/or an alkaline earth metal ion in an amount of 1 ppm or below. A process for preparing the above (co)polycarbonate composition by the melt transesterification process involves the reaction of a dihydroxy compound such as bisphenol A and a carbonic diester such as diphenyl carbonate with a nitrogen-containing basic compound (a), and/or, a compound (b) containing an element selected from the group consisting of elements belonging to Groups I, II, IV and V of the periodic table as a catalyst.Type: GrantFiled: April 15, 1994Date of Patent: December 12, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Yoshimichi Okano, Michiyo Tanigawa, Yutaka Fukuda
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Patent number: 5472823Abstract: A photosensitive resin composition comprising, as its main ingredient, a poly(amic acid) resin constituted of a diamino compound represented by formula: ##STR1## and optionally used other diamino compound and a tetracarboxylic acid dianhydride as its constituent monomers and/or a poly(amic acid) ester resin obtained by esterifying said poly(amic acid) resin and/or a polyimide resin obtained by a dehydrating or alcohol-eliminating ring-closure reaction of said poly(amic acid) resin or poly(amic acid) ester resin has an excellent developability and a high film strength and can form a relief patter of low thermal expansion.Type: GrantFiled: January 15, 1993Date of Patent: December 5, 1995Assignee: Hitachi Chemical Co., Ltd.Inventors: Hideo Hagiwara, Makoto Kaji, Hiroshi Nishizawa, Kenji Suzuki, Yasunori Kojima
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Patent number: 5473010Abstract: The present invention relates to a polyimide based resin composition comprises 1 to 50 parts by weight of polyetherimide for 100 parts by weight a resin composition comprising 50 to 99 parts by weight of polyarylether ketone and 50 to 1 parts by weight of polyimide having specific structural units.The polyimide based resin compositions have excellent fatigue characteristics and creep resistance and are expected widely to apply in field of machine and automobile parts which is required permanence for mechanical strength.Type: GrantFiled: August 30, 1994Date of Patent: December 5, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Atsushi Morita, Tomohito Koba, Toshiaki Takahashi, Katsunori Shimamura, Toshiyuki Kataoka, Hiroyuki Furukawa, Hiroaki Tomimoto
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Patent number: 5470939Abstract: A polycarbonate copolymer having a desirable heat resistance and impact resistance, which comprises a carbonate structural unit of the formula (I): ##STR1## wherein A is alkylidene, alkylene, arylene, arylalkylene, --O--, --S--, --SO.sub.2 -- or a single bond, and a carbonate structural unit of formula (II): ##STR2## wherein X.sup.1 and Y.sup.1 are hydrogen, halogen or an organic group and m and n are 1 to 4, wherein the proportion of the carbonate structural unit of the formula (II) being 2 to 15 mole % based on the amount of the carbonate structural unit of the formulas (I) and (II), and the viscosity average molecular weight of the copolymer being 15,000 to 40,000.Type: GrantFiled: October 13, 1994Date of Patent: November 28, 1995Assignee: Idemitsu Petrochemical Co., Ltd.Inventor: Mitsugu Nakae
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Patent number: 5470943Abstract: This invention relates to a novel fluorine-containing polyimide or polyimide copolymer being colorless and having transparency and very low dielectric characteristics, and has a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the polyimide or polyimide copolymer and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition.Type: GrantFiled: December 21, 1994Date of Patent: November 28, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshihiro Sakata, Wataru Yamashita, Yuichi Okawa, Shoji Tamai, Tsutomu Ishida, Mitsunori Matsuo, Keizaburo Yamaguchi, Akihiro Yamaguchi
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Patent number: 5464927Abstract: Copolyamic acid is obtained from tetracarboxylic acid dianhydride, diamine and a fluorinated diamine and/or fluorinated tetracarboxylic acid dianhydride; and optionally ester or amine salt derivative thereof to obtain radiation sensitive polymer; and low optical high thermally stable polyimide from curing the above polyamic acid and/or derivative thereof.Type: GrantFiled: May 10, 1993Date of Patent: November 7, 1995Assignee: International Business Machines CorporationInventors: Marie Angelopoulos, Jeffrey D. Gelorme, Jeffrey W. Labadie, David A. Lewis, Sally A. Swanson, Nancy C. Labianca
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Patent number: 5464925Abstract: The present invention is an oligomer represented by the formula: ##STR1## wherein X is a moiety selected from the group consisting of: ##STR2## where each Y is independently S, O, CH.sub.2, C.dbd.O, CH.sub.3 --C--CH.sub.3, O.dbd.S.dbd.O, or CF.sub.3 --C--CF.sub.3.In another aspect, the present invention is a polymer of the above-described oligomer.Type: GrantFiled: May 25, 1994Date of Patent: November 7, 1995Assignee: The Dow Chemical CompanyInventors: Eric S. Moyer, Denise J. D. Moyer
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Patent number: 5453482Abstract: Provided is a new process useful for preparing arylsulfonyl halides, which comprises the addition or drowning of halosulfonation reaction products, produced by the reaction of aromatic compounds (arenes), with excess halosulfonic acid, into C.sub.3 -C.sub.6 aliphatic ketones, preferably acetone, isopropyl alcohol, or mixtures thereof, instead of drowning into water as is known in the art of aromatic sulfonyl chloride preparation. Less heat of reaction is observed, thus making the drowning of the halosulfonation reaction mixture safer and more controllable. Further, less hydrogen chloride gas is evolved from the drowning mixture and generally more highly pure arylsulfonyl chlorides are produced.Type: GrantFiled: March 18, 1994Date of Patent: September 26, 1995Assignee: Eastman Chemical CompanyInventors: Max A. Weaver, William W. Parham, James J. Krutak, Kim S. Chamberlin
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Patent number: 5449742Abstract: 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: February 15, 1994Date of Patent: September 12, 1995Assignee: Amoco CorporationInventors: Allyson J. Beuhler, David A. Wargowski
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Patent number: 5449741Abstract: A polyimide optical material, composed of a perfluorinated polyimide having a perfluorinated repeating unit represented by general formula (1) ##STR1## wherein R.sub.1 is a tetravalent perfluorinated organic group; and R.sub.2 is a divalent perfluorinated organic group.Type: GrantFiled: October 25, 1993Date of Patent: September 12, 1995Assignee: Nippon Telegraph and Telephone CorporationInventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
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Patent number: 5442030Abstract: Polyimides are made from the novel diamines 1,2-bis(3-aminophenyl)perfluorocyclobutane, 1,2-bis(3- or 4-aminophenyl)perfluorocyclobutene, -cyclopentene and -cyclohexene, by reaction with aromatic carboxylic anhydrides. The polyimides are useful for coatings and films.Type: GrantFiled: October 14, 1993Date of Patent: August 15, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Zhenyu Yang
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Patent number: 5434240Abstract: Disclosed herein are novel poly(imide-ethers) containing ortho substitution in the main chain of the polymer. These polymers are made from novel aromatic bis-carboxylic anhydrides which contain two ether groups attached to an aromatic ring in ortho positions to each other. The polymers are particularly useful for films, fibers and encapsulation, as well as thermoplastics.Type: GrantFiled: April 29, 1994Date of Patent: July 18, 1995Assignee: The University of LiverpoolInventors: Geoffrey C. Eastmond, Jerzy Paprotny
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Patent number: 5432256Abstract: The present invention provides a liquid crystal aligning film having a reduced after image and a good liquid crystal aligning property caused by a rubbing treatment of a thin film consisting of organics, and its liquid crystal display device.Type: GrantFiled: June 7, 1993Date of Patent: July 11, 1995Assignee: Chisso CorporationInventors: Yukino Abe, Minoru Nakayama, Shizuo Murata
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Patent number: 5427998Abstract: A polycarbonate resin solution for forming a thermal-sublimating dye-receiving layer film, comprising a random copolycarbonate resin dissolved in an organic solvent, the resin having a structural unit represented by following formula (1) and a structural formula represented by following formula (2) or (3), the molar ratio of the structural unit represented by formula (1) to the structural unit represented by formula (2) or (3) being from 35/65 to 65/35, and having a number average molecular weight of from 5,000 to 50,000. ##STR1## wherein R.sup.1 to R.sup.12 each represents a hydrogen atom, a halogen atom, or an alkyl group having from 1 to 4 carbon atoms and in formula (1), A represents a straight chain, branched, or cyclic alkylidene group having from 1 to 10 carbon atoms, an aryl-substituted alkylidene group, an arylene group, or a sulfonyl group.Type: GrantFiled: June 20, 1994Date of Patent: June 27, 1995Assignee: Mitsubishi Gas Chemical Co., Ltd.Inventors: Toshikazu Umemura, Satoshi Kanayama
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Patent number: 5414070Abstract: Disclosed is a poly(amide-ether-imide) and the preparation of the same. An ether chain-containing aromatic diamine is subject to thermal condensation with trimellitic anhydride (TMA) in a polar solvent to obtain diimide dicarboxylic acid, followed by polycondensing the diimide dicarboxlic acid with diamine to form the poly(amide-ether-imide). The poly(amide-ether-imide) of the present invention has superior strength, heat resistance, and processability. The preparation of the present invention is simple and economic.Type: GrantFiled: December 3, 1993Date of Patent: May 9, 1995Assignee: National Science CouncilInventors: Chin-Ping Yang, Sheng-Huei Hsiao, Jiun-Hung Lin
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Patent number: 5412065Abstract: Polyimide oligomers are described which comprise the intercondensation product of a monomer mixture comprising (A) at least one aromatic bis(ether anhydride), (B) at least one phenylindane diamine, and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and amines, wherein each end-cap monomer (C) contains at least one crosslinkable group in the molecule and wherein the phenylindane diamine component (B) is present in the mixture in a stoichiometric excess. The monomers react in a suitable solvent under an inert atmosphere to form polyimide oligomers having a number average molecular weight of from about 1,000 to about 15,000. The polyimide oligomers of the present invention are readily processed to form polyimide matrix resins with high temperature and oxidative stability.Type: GrantFiled: April 9, 1993Date of Patent: May 2, 1995Assignee: Ciba-Geigy CorporationInventors: Michael Amone, Mark Southcott
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Patent number: 5412059Abstract: Novel molecular weight controlled and endcapped polybenzimidazoles (PBI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenylbenzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The PBI are endcapped with mono(hydroxyphenyl)benzimidazoles. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. Mono(hydroxyphenyl)benzimidazoles are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic (o-diamine)s in diphenylsulfone. Molecular weight controlled and endcapped PBI of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties.Type: GrantFiled: April 5, 1993Date of Patent: May 2, 1995Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
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Patent number: 5412060Abstract: The invention relates to a process for the production of polycarbonates by the two-phase interfacial method in which deviations between measured and estimated variables are continuously minimized by means of a suitably selected observer or filter system on the basis of a process model with an empirical Mark-Houwink relation adapted to the process. The variables estimated by the observer/filter are converted into control variables which are used to set input streams of the production process. Product quality is kept constant, changes in load or set values are quickly intercepted and even disturbances not readily accessible to measurement are taken into account by the process control.Type: GrantFiled: January 31, 1994Date of Patent: May 2, 1995Assignee: Bayer AktiengesellschaftInventors: Claus Wulff, Uwe Hucks, Rolf Bachmann, Gunther Weymans, Jurgen Kadelka, Wolfgang Herrig
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Patent number: 5412066Abstract: Four phenylethynyl amine compounds--3 and 4-aminophenoxy-4'-phenylethynylbenzophenone, and 3 and 4-amino-4'-phenylethynylbenzophenone--were readily prepared and were used to endcap imide oligomers. Phenylethynyl-terminated amide acid oligomers and phenylethynyl-terminated imide oligomers with various molecular weights and compositions were prepared and characterized. These oligomers were cured at 300.degree. C. to 400.degree. C. to provide crosslinked polyimides with excellent solvent resistance, high strength and modulus and good high temperature properties. Adhesive panels, composites, films and moldings from these phenylethynyl terminated imide oligomers gave excellent mechanical performance.Type: GrantFiled: March 3, 1994Date of Patent: May 2, 1995Assignee: Ther United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Paul M. Hergenrother, Robert G. Bryant, Brian J. Jensen, Stephen J. Havens
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Patent number: 5410013Abstract: Poly(arylene ether) sulfones that contain thiophene rings within the aromatic polymer backbone are disclosed, along with fibers, films, and other articles of manufacture formed therefrom.Type: GrantFiled: June 1, 1994Date of Patent: April 25, 1995Assignee: The University of North Carolina at Chapel HillInventors: Joseph M. DeSimone, Edward T. Samulski, Robert S. Archibald, Valeria V. Sheares
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Patent number: 5410012Abstract: Novel poly(N-arylenebenzimidazole)s (PNABIs) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl-N-arylene benzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl-N-arylenebenzimidazole) monomers are synthesized by reacting phenyl-4-hydroxybenzoate with bis(2-aminoanilino)arylenes in diphenylsulfone. Moderate molecular weight PNABIs of new chemical structures were prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyl-N-arylenebenzimidazole)s permits a more economical and easier way to prepare PNABIs than previous routes.Type: GrantFiled: March 5, 1993Date of Patent: April 25, 1995Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
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Patent number: 5405933Abstract: The present invention provides copolymerized polycarbonates having improved flow and formability, in addition to excellent mechanical properties, heat resistance, transparency, and water resistance obtained by copolymerization of two or more aromatic dihydroxy compounds and a compound capable of reacting with those aromatic dihydroxy compounds to form carbonate linkages, characterized in that, of all the constituent repeating units derived from aromatic dihydroxy compounds, 2-40 mole % are derived from resorcin and/or substituted resorcins.Type: GrantFiled: September 9, 1993Date of Patent: April 11, 1995Assignee: General Electric CompanyInventors: Takeshi Sakashita, Tomoaki Shimoda, Takashi Nagai
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Patent number: 5405956Abstract: Low molecular weight cyclic oligomers of formula (I) ##STR1## in which n is an integer of 2 to 20, and each C in the oligomer is a radical of formula (II): ##STR2## and each X in the oligomer is --O--R--O-- or --S--R--S--, B and D are both carbonyl groups CO, or together represent a divalent radical of formula ##STR3## in which A.sub.1, A.sub.2, A.sub.3 A.sub.4, Ar.sub.1, Ar.sub.2 and Ar.sub.3 are selected from a variety of aromatic radicals, A.sub.1, A.sub.2, Ar.sub.3 and Ar.sub.4 also possibly being hydrogen, are useful in the production of high molecular weight, linear, polyketones, polyphthalazines and polyisoquinolines; the cyclic oligomers have low melt viscosities when heated above their softening temperatures and can be readily molded, whereafter they can be rings-open polymerized to form molded high molecular weight polymer products with excellent properties.Type: GrantFiled: March 1, 1994Date of Patent: April 11, 1995Inventors: Allan S. Hay, Kwok P. Chan
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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: 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: 5395914Abstract: Polyarylene ethers that contain xanthone units and have a very high heat resistance can be prepared from inexpensive, readily accessible monomers by polycondensation in a basic medium under essentially anhydrous conditions in the presence or absence of an aromatic solvent at temperatures of from 150.degree. to 400.degree. C. Xanthone monomers and also hydroxyhalogen-substituted benzophenone compounds may be used as starting materials.Type: GrantFiled: May 26, 1993Date of Patent: March 7, 1995Assignee: Hoechst AktiengesellschaftInventors: Peter Wilharm, Thomas Weller, Michael Meier
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Patent number: 5391691Abstract: A process for producing an aromatic polycarbonate with improved heat resistance comprising melt polycondensing an aromatic diol compound and a carbonic acid diester compound in the presence of an interesterification catalyst and in the co-presence of an organosilicon compound.Type: GrantFiled: October 22, 1993Date of Patent: February 21, 1995Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Masuzo Yokoyama, Kazuhide Takakura, Junji Takano
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Patent number: 5391693Abstract: A polycarbonate copolymer having a desirable heat resistance and impact resistance, and a process for producing the copolymer. The polycarbonate copolymer comprises a carbonate structural unit of the formula (I): ##STR1## wherein A is alkylidene, alkylene, arylene, arylalkylene, --O--, --S--, --SO.sub.2 -- or a single bond, and a carbonate structural unit of formula (II): ##STR2## wherein X.sup.1 and Y.sup.1 are hydrogen, halogen or an organic group and m and n are 1 to 4, wherein the proportion of the carbonate structural unit of the formula (II) being 2 to 15 mole % based on the amount of the carbonate structural unit of the formulas (I) and (II), and the viscosity average molecular weight of the copolymer being 15,000 to 40,000.Type: GrantFiled: October 1, 1993Date of Patent: February 21, 1995Assignee: Idemitsu Petrochemical Co., Ltd.Inventor: Mitsugu Nakae
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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: 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: 5373081Abstract: Polyether ketones and polyether sulfones based on phenylindane and the use thereof for optical systemsPolymeric ethers containing phenylindane units, of the formula ##STR1## in which X=CO or SO.sub.2,Y=a divalent heteroarylene radical or an arylene radical or a divalent group of two aryl radicals which are bonded to one another via a bridge,R.sup.1 =CH.sub.3 ; R.sup.2 =R.sup.3 =H, orR.sup.2 =CH.sub.3 ; R.sup.1 =R.sup.3 =(C.sub.1 to C.sub.16)-alkyl or aryl, orR.sup.1 =CH.sub.3 ; R.sub.3 =H; R.sup.2 =(C.sub.1 to C.sub.16)-alkyl or aryl,are transparent and are suitable for optical systems.Type: GrantFiled: February 24, 1993Date of Patent: December 13, 1994Assignee: Hoechst AktiengesellschaftInventors: Dazhong Yang, Gerhard Maier, Oskar Nuyken, Michael-Joachim Brekner, Freddy Helmer-Metzmann
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Patent number: 5362841Abstract: A process for preparing halogenated polycarbonate wherein the total amount of base the end pH of the aqueous phaser and the amount of coupling catalyst employed in the reaction are controlled to selected levels.Type: GrantFiled: May 17, 1993Date of Patent: November 8, 1994Assignee: The Dow Chemical CompanyInventors: Sarat Munjal, Clark J. Cummings, Che-I Kao
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Patent number: 5362838Abstract: There are disclosed carbonate polymers having ethenyl aryl moieties. Such carbonate polymers are prepared from one or more multi-hydric compounds and have an average degree of polymerization of at least about 1 based on multi-hydric compound. These polymers, including blends thereof, can be easily processed and shaped into various forms and structures according to the known techniques. During or subsequent to the processing, the polymers can be crosslinked, by exposure to heat or radiation, for example, to provide crosslinked polymer compositions. These compositions have a good combination of properties, including for example, processability into shaped articles having unexpectedly good combinations of toughness, solvent resistance, ignition resistance, modulus and resistance to thermal linear expansion.Type: GrantFiled: February 19, 1993Date of Patent: November 8, 1994Assignees: Virginia Polytechnic Institute and State University, The Dow Chemical CompanyInventors: James E. McGrath, Stephen E. Bales, Daniel M. Knauss, Thomas A. Chamberlin, Michael J. Mullins, Maurice J. Marks
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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: 5362836Abstract: Polymer electrolytes are described that comprise a sulfonated aromatic polyether ketone, e.g. of the formula II ##STR1## where A is from 0.2 to 1,c is from 0 to 0.8, anda+c=1.The polymer electrolytes are prepared by dissolving an aromatic polyether ketone in 94-97% by weight sulfuric acid and adding a sulfonating agent, e.g. oleum, to the solution until the sulfuric acid concentration is from 98 to 99.9% by weight.Type: GrantFiled: June 9, 1993Date of Patent: November 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Freddy Helmer-Metzmann, Frank Osan
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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: 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: 5354836Abstract: Poly(arylene ether)ketones, polyamides, and poly(benzoxazoles) that contain thiophene rings within the aromatic polymer backbone are disclosed, along with fibers, films, and other articles of manufacture formed therefrom.Type: GrantFiled: September 2, 1993Date of Patent: October 11, 1994Assignee: The University of North Carolina at Chapel HillInventors: Edward T. Samulski, Joseph M. DeSimone