Reactant Contains Three Or More Carboxylic Acid Groups Or Is Derivative Thereof Patents (Class 528/188)
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Patent number: 5317081Abstract: A method and apparatus are disclosed for conducting a physical process and a chemical reaction by exposing a material containing a volatile substance to microwave radiation where the morphology of said material will change when exposed to such radiation. The power of said radiation is adjusted over time as the morphology of the material changes to maximize the effect of the radiation in order to produce a product in a minimum amount of time that is substantially free of said volatile substance.The method and apparatus can also be used to conduct such a process or reaction with materials that do not contain a volatile material.In one embodiment a method and apparatus are disclosed for manufacturing a polyimide from a precursor in a solvent by exposing the precursor to microwave radiation in a tuneable microwave resonant cavity that is tuned during imidization to achieve critical coupling of the system. Microwave power is controlled to remove the solvent and obtain the desired level of reaction.Type: GrantFiled: November 27, 1991Date of Patent: May 31, 1994Assignee: International Business Machines CorporationInventors: Jeffrey D. Gelorme, David A. Lewis, Jane M. Shaw
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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: 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: 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: 5308569Abstract: A process for the preparation of an aromatic polyimide film includes the steps of casting a polyamide acid solution containing an imidization agent on a support in the form of a film, heating the filmy cast solution on the support at a temperature of 80.degree. to 200.degree. C. to obtain a self-supportable film; peeling the self-supportable film from the support; and further heating the film at a temperature of not lower than 300.degree. C. The polyamide acid solution includes a polyamide acid obtained by polymerization reaction of 3,4,3',4'-biphenyltetracarboxylic dianhydride and p-phenylenediamine in a mixture of a polar organic solvent and a small amount of an imidization agent selected from imidazole, a substituted imidazole, benzimidazole, a substituted benzimidazole, isoquinoline, and a substituted pyridine.Type: GrantFiled: November 26, 1991Date of Patent: May 3, 1994Assignee: Ube Industries, Ltd.Inventors: Toshikazu Hamamoto, Hiroshi Inoue, Yoshiyuki Miwa, Tetsuji Hirano, Katsuo Imatani, Kenji Matsubara, Takashi Kohno
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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: 5304625Abstract: Phosphazene-containing amines having at least one amine or substituted amine moiety reactive with nitrile groups of the phthalonitrile monomers or oligomeric resins are useful curing agents for phthalonitriles. Typically, the phosphazene-containing amines useful as curing agents in the present invention have the formula: ##STR1## wherein each of X.sub.1-6 is a hydrogen, an unsubstituted amine group, or an amine group substituted with C.sub.1 -C.sub.12 alkyl groups or aromatic groups, at least one of X.sub.1-6 includes an amine group, and each of R'.sub.1-6 is an alkyl, aromatic, or alkyl-substituted aromatic moiety, or a linear polymer of the phosphazene-based amine monomer. The curing agents enhance the speed of cure and also add flame retardancy to the cured polymers.Type: GrantFiled: February 19, 1993Date of Patent: April 19, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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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: 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: 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: 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: 5298601Abstract: A high temperature fluorinated polyimide is made by forming a solution that includes a 3F-monomer and an aromatic or aliphatic diamine such that the solution has a ratio of 3F-monomer to diamine of greater than 1.05. The 3F-monomer is 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 solution is mixed so the 3F-monomer reacts with the diamine to form a 3F-polyimide.Type: GrantFiled: December 4, 1992Date of Patent: March 29, 1994Assignee: United Technologies CorporationInventor: Daniel A. Scola
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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: 5294696Abstract: The present invention provides a dehydrating agent which is less poisonous and which can be easily handled in producing a polyisoimide by dehydrating a polyamic acid. A process is also provided for producing a polyisoimide without requiring the separation of by-products.That is, the process for producing the polyisoimide of the present invention includes the step of using a dihyroquinoline derivative represented by the formula ##STR1## (wherein each R.sup.1 and R.sup.2 is independently a monovalent organic group having 1 to 8 carbon atoms) as the dehydrating agent in producing the polyisoimide by dehydrating the polyamic acid.Type: GrantFiled: December 11, 1991Date of Patent: March 15, 1994Assignee: Chisso CorporationInventors: Hirotoshi Maeda, Kouichi Kunimune
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Patent number: 5290908Abstract: Aromatic polyimides with acetylenic end groups are cured by coupling together thermally or catalytically using cuprous salts as catalysts to increase molecular weight with little or no by-product formation. These polyimides can be shaped and formed prior to the coupling.The acetylenic end-capped aromatic polyimides are formed by the reaction of an aromatic dianhydride, an acetylenic organic monoamine compound which will provide the reactive end groups and optionally an aromatic diamine.Type: GrantFiled: January 24, 1975Date of Patent: March 1, 1994Assignee: The University of Notre Dame du LacInventor: Gaetano F. D'Alelio
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Patent number: 5290909Abstract: A polyimide composition for use in making polyimide/copper foil laminate that does not require an adhesive layer between the polyimide substrate and the copper foil. A polyimide precursor is first prepared from a monomer composition, which comprises a dianhydride and an imidazole-containing or benzimidazole-containing compound, or mixture thereof The polyimide precursor is then coated onto a copper foil and subsequently subject to an imidization reaction to form a polyimide/copper foil laminate, which exhibits excellent peel strength and flatness while retaining all the advantageous properties that are characteristic of polyimide resins, such as excellent mechanical strength and heat and chemical resistance. Because the polyimide/copper foil laminates disclosed in the present invention are made without the need to apply an adhesive layer, the process of manufacturing the same is greatly simplified and the cost of production therefor can be substantially reduced.Type: GrantFiled: May 28, 1993Date of Patent: March 1, 1994Assignee: Industrial Technology Research InstituteInventors: Han L. Chen, Syh-Ming Ho, Tsung H. Wang, Jing-Pin Pan
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Patent number: 5288843Abstract: 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: November 5, 1990Date of Patent: February 22, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoji Tamai, Masahiro Ohta, Saburo Kawashima, Katsuaki Iiyama, Hideaki Oikawa, Akihiro Yamaguchi, Kouji Ohkoshi, Masao Yoshikawa
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Patent number: 5286840Abstract: A thermally stable polyimide which is blocked at the polymer terminal with a dicarboxylic acid anhydride represented by the formula (III): ##STR1## wherein Z is a divalent radical selected from the group consisting of a monoaromatic radical which is substantially unsubstituted or substituted with a radical having no reactivity with amine or dicarboxylic acid anhydride and has from 6 to 15 carbon atoms, a condensed polyaromatic radical or a noncondensed aromatic radical connected each other with a direct bond or a bridge member, and has a fundamental skeleton represented by recurring structural units of the formula (IV): ##STR2## and a process of preparing the polyimide.Type: GrantFiled: November 21, 1991Date of Patent: February 15, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Hideaki Oikawa, Nobuhito Koga, Akihiro Yamaguchi, Shoji Tamai
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Patent number: 5286841Abstract: This invention concerns novel fluorine-containing diamines, polyamides and polyimides. The compounds are useful in the formation of moisture resistant films, fibers and shaped articles.Type: GrantFiled: September 14, 1992Date of Patent: February 15, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Brian C. Auman, Andrew E. Feiring
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Patent number: 5283313Abstract: A readily processable polyimide being blocked at the terminal of a polymer molecule with a divalent radical derived from dicarboxylic acid anhydride represented by the formula (IV): ##STR1## wherein Z is a divalent radical selected from the group consisting of a monoaromatic radical which is substantially unsubstituted or substituted with a radical having no reactivity with amine or carboxylic acid anhydride and has from 5 to 15 carbons atoms, condensed polyaromatic radical or noncondensed aromatic radical connected each other with a direct bond or a bridge member, and having a fundamental skeleton represented by recurring structural units of the formula (III): wherein X and Y are --O-- or --CO-- and differ each other; preparation process of the polyimide; and resin composition containing the polyimide and fibrous reinforcement.Type: GrantFiled: November 21, 1991Date of Patent: February 1, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Wataru Yamashita, Shoji Tamai, Akihiro Yamaguchi
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Patent number: 5281690Abstract: Base-soluble release layer compositions for microlithographic processing, comprising nonamic acid functionalized polyamic acid/imide resins are disclosed. These materials permit concurrent lithographic development of photoresist and release layers. They also afford effective lift-off, by alkaline media, even after high imidization.Type: GrantFiled: March 30, 1989Date of Patent: January 25, 1994Assignee: Brewer Science, Inc.Inventors: Tony Flaim, James E. Lamb, III, Gregg Barnes, Terry Brewer
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Patent number: 5280102Abstract: Heat-resistant bonding materials are composed of a polyimide precursor end-capped at molecule ends thereof and/or an imide compound formed from the polyimide precursor. They may also contain fine particles of at least one material selected from metals, metal oxides, metal carbides and metal nitrides.Type: GrantFiled: March 28, 1990Date of Patent: January 18, 1994Assignees: Hitachi, Ltd., Hitachi Chemical Co.Inventors: Haruhiko Matsuyama, Fusaji Shoji, Atsushi Honda, Teruki Aizawa
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Patent number: 5280103Abstract: 1-[2,2-bis(trifluoromethyl)-3,3,4,4,5,5,5-heptafluoropentyl]-3,5-diaminoben zene and 1-[2,2-bis(trifluoromethyl)-3,3,4,4,5,5,5-heptafluoropentyl]-4-aminobenzen e, as well as fluorinated polymers, preferably polyimides. The perfuuoroalkyl group of these amines is connected to the benzene ring through a tertiary carbon atom followed by a methylene group. This renders the amines more reactive than other amines, where the perfluoroalkyl group is connected directly to the benzene ring. The absence of hydrogen from the group containing the tertiary carbon atom which is adjacent to the perfluorinated groups, prohibits dehydrofluorination.Type: GrantFiled: June 17, 1992Date of Patent: January 18, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Brian C. Auman, David P. Higley, Kirby V. Scherer
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Patent number: 5280101Abstract: The invention relates to a polyimide substantially built up from monomeric units of 3,3',4,4'-benzophenonetetracarboxylic dianhydride and monomeric units of a primary aliphatic diamine. The polyimide according to the invention is characterized in that the primary aliphatic diamine is substantially 1,4-diaminobutane. The thermal stability of the polyimide according to the invention has surprisingly been found to be very good. Owing to this very good thermal stability, the polyimides according to the invention can very well be processed at--relatively--high processing temperatures without any appreciable thermal degradation of the polyimide. As a result, the polyimides processing potential has increased considerably. Also, articles made of the polyimides according to the invention can be used at significantly higher temperatures. Said articles have very good mechanical properties. Articles containing a polyimide are suited for being used in the most diverse applications.Type: GrantFiled: July 10, 1992Date of Patent: January 18, 1994Assignee: DSM N.V.Inventors: Cornelis E. Koning, Lilian M. J. Teuwen, Egbert W. Meijer
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Patent number: 5278277Abstract: Phenylquinoxaline copolymers of the general formula: ##STR1## are described where R* signifies a polar unit. The application of these copolymers for producing highly heat-resistant dielectrics is also described.Type: GrantFiled: November 25, 1992Date of Patent: January 11, 1994Assignee: Siemens AktiengesellschaftInventors: Hellmut Ahne, Lothar Zapf
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Patent number: 5276132Abstract: A liquid crystal aligning agent containing a polymer selected from the group consisting of a polyamic acid having a steroidal skeleton and an imidized product thereof; and a liquid crystal display device to which the liquid crystal aligning agent is applied.Type: GrantFiled: March 4, 1992Date of Patent: January 4, 1994Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Michinori Nishikawa, Tsuyoshi Miyamoto, Yasuaki Yokoyama, Yasuo Matsuki
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Patent number: 5276133Abstract: A favorably processable polyimide which has recurring structural units represented by the formula (I): ##STR1## wherein R is a tetravalent radical having from 2 to 27 carbon atoms and is selected from the group consisting of an aliphatic radical, alicyclic radical, monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected to each other with a direct bond or a bridge member, and is blocked at the polymer chain end with aromatic dicarboxylic anhydride represented by the formula (II): ##STR2## wherein X is a divalent radical selected from the group consisting of a monoaromatic radical having from 6 to 27 carbon atoms, condensed polyaromatic radical and noncondensed aromatic radical connected to each other with a direct bond or a bridge member.Type: GrantFiled: June 4, 1992Date of Patent: January 4, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yuichi Okawa, Shoji Tamai, Akihiro Yamaguchi
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Patent number: 5272248Abstract: A process for preparing polyamides having enhanced melt flow properties is described. The process consists of heating a mixture of a high molecular weight poly(amic acid) or polyimide with a low molecular weight amic acid or imide additive in the range of 0.05 to 15% by weight of additive. The polyimide powders so obtained show improved processability, as evidenced by lower melt viscosity by capillary rheometry. Likewise, films prepared from mixtures of polymers with additives show improved processability with earlier onset of stretching by TMA.Type: GrantFiled: May 22, 1992Date of Patent: December 21, 1993Assignee: The United States of America as Represented by the United States National Aeronautics and Space AdministrationInventors: J. Richard Pratt, Terry L. St. Clair, Diane M. Stoakley, Harold D. Burks
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Patent number: 5272247Abstract: The present invention provides a polyimide having all of small dielectric constant, small thermal expansion coefficient, high heat resistance, high glass transition temperature and high mechanical properties, a precursor of the polyimide, and processes for producing them. A polyimide precursor whose molecular chain comprises repeating units represented by the following general formula (1) and repeating units represented by the following general formula (2): ##STR1## wherein R.sup.1 is at least one kind of tetravalent organic group selected from the group consisting of ##STR2## R.sup.2 is at least one kind of divalent organic group having a linear structure which is selected from the group consisting of ##STR3## m is an integer of 1 to 4, and R.sup.3 is a divalent organic group having a non-linear structure which contains at least two aromatic rings.Type: GrantFiled: October 21, 1991Date of Patent: December 21, 1993Assignee: Hitachi, Ltd.Inventors: Hideo Sotokawa, Fusaji Shoji, Fumio Kataoka, Hidetaka Satou
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Patent number: 5270438Abstract: A fluorine-containing polyimide having a low dielectric constant, low water absorption and excellent heat resistance and moisture resistance and a precursor thereof such as a fluorine-containing polyamide-acid, can be prepared by reacting an acid anhydride with an aromatic diamine having perfluoroalkyl group.Type: GrantFiled: April 3, 1991Date of Patent: December 14, 1993Assignee: Hitachi Chemical Company, Ltd.Inventors: Masami Yusa, Shinji Takeda, Yasuo Miyadera
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Patent number: 5268446Abstract: A readily melt-processable polyimide obtained by reacting diamino-diphenyl ether with 3,3',4,4'-biphenyltetracarboxylic dianhydride in the presence of phthalic anhydride and thermally or chemically imidizing the resultant polyamic acid.Type: GrantFiled: August 9, 1991Date of Patent: December 7, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
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Patent number: 5268447Abstract: A readily melt processable polyimide obtained by reacting diamine represented by the formula: 4,4' ##STR1## wherein n is an integer of 1 or 2, with 3,3'4,4' -diphenylethertetracarboxylic dianhydride and/or 4,4' -(p-phenylenedioxy)diphthalic dianhydride or a mixture of these tetracarboxylic acid dianhydrides and pyromellitic dianhydride in the presence of phthalic anhydride.Type: GrantFiled: July 15, 1992Date of Patent: December 7, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
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Patent number: 5268519Abstract: Polyetherimide oligomers having crosslinking end cap moieties which provide improved solvent-resistance to cured composites are generally represented by the formula: ##STR1## wherein X=--O-- or --S--; ##STR2## n=1 or 2; ##STR3## E=allyl or methallyl; R=a trivalent C.sub.(6-13) aromatic organic radical;R.sub.1 =any of lower alkyl, lower alkoxy, aryl, or substituted aryl;R'=a divalent C.sub.(6-30) aromatic organic radical;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --Blends generally comprise substantially equimolar amounts of the oligomers and a comparable, compatible, noncrosslinking, etherimide polymer of substantially the same backbone. The crosslinkable oligomers are made by reacting substituted phthalic anhydrides with hydroxyaryl amines and suitable crosslinking end cap reactants, or by self-condensation of phthalimide salts followed by capping the polymers.Type: GrantFiled: September 25, 1990Date of Patent: December 7, 1993Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5264545Abstract: Solutions of polyimide-forming starting materials are provided containing diamines and tetracarboxylic diesters; the tetracarboxylic diesters comprise a mixture of from 0.05 to 0.95 mol % of oxydiphthalic diesters and from 0.05 to 0.95 mol % of benzophenonetetracarboxylic diesters, biphenyltetracarboxylic diesters or mixtures thereof.Type: GrantFiled: November 2, 1992Date of Patent: November 23, 1993Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Rainer Blum, Hans J. Heller, Klaus Lienert
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Patent number: 5264534Abstract: Processes for producing oriented films of semicrystalline thermoplastic polymers, such as polyimides, and films produced thereby are disclosed. One process includes partial crystallization or imidization, orientation and further crystallization or imidization. Another process includes rendering a film of semicrystalline thermoplastic polymer amorphous, orienting the film and introducing crystallinity.Type: GrantFiled: October 31, 1991Date of Patent: November 23, 1993Assignee: Foster-Miller, Inc.Inventors: Robert F. Kovar, Richard W. Lusignea, R. Ross Haghighat
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Patent number: 5262516Abstract: A process for preparing a polyetherimide-polyimide copolymer by (a) reacting a bis (ether anhydride) with a stoichiometric excess of an organic diamine in an inert, non-polar solvent to form an amine-terminated oligomer-solvent mixture; (b) removing unreacted organic diamine from the oligomer-solvent mixture; and (c) reacting the oligomer with an aromatic dianhydride.Type: GrantFiled: November 26, 1991Date of Patent: November 16, 1993Assignee: General Electric CompanyInventor: Brent A. Dellacoletta
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Patent number: 5262511Abstract: A compound of the formula ##STR1## wherein R is a hydrocarbon of three to about 50 carbon atoms and the residue of the reaction of triol R(OH).sub.3 with the anhydride of Formula II;Y is CR.sub.5 R.sub.6, O,S,NCH.sub.3 wherein R.sub.5 and R.sub.6 are the same or different and are hydrogen, alkyl of one to three carbon atoms, inclusive, or phenyl;x is O or 1;R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are selected from the group consisting of hydrogen, phenyl or aliphatic of one to about twenty carbon atoms, inclusive, and R.sub.2 and R.sub.4 joined together form a normal alkylene or alkenylene chain of two to about six carbon atoms, inclusive, unsubstituted or substituted with one to six alkyl groups having from one to about four carbon atoms, inclusive.a process to make the compounds;and branched aromatic carbonate polymers having incorporated therein in the branching component a compound of the above formula.Type: GrantFiled: March 3, 1992Date of Patent: November 16, 1993Assignee: General Electric Co.Inventors: Joseph J. Caringi, Luca P. Fontana, John R. Campbell
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Patent number: 5262515Abstract: A curable fluorine-containing polyimide of the formula: ##STR1## wherein R.sup.1 is a group derived from an aromatic tetracarboxylic acid dianhydride by the removal of two acid anhydride groups,R.sup.2 is a group derived from an aromatic diamine by the removal of two amino groups,A.sup.1 is a residue of the formula: ##STR2## (wherein R.sup.2 is the same as defined above, and Z is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms),A.sup.2 is a residue of the formula: ##STR3## (wherein R.sup.1 and Z are the same as defined above), and n is a number of 0 to 90, and at least one of the groups R.sup.1 and R.sup.Type: GrantFiled: July 10, 1990Date of Patent: November 16, 1993Assignee: Daikin Industries, Ltd.Inventors: Motonobu Kubo, Tsutomu Kobayashi
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Patent number: 5260408Abstract: Polyimide compositions, films, and electronic devices using polyimides, based on 9,9-bis(perfluoroalkyl)xanthene-2,3,6,7-tetracarboxylic dianhydride or 9-aryl-9(perfluoroalkyl)xanthene-2,3,6,7-tetracarboxylic dianhydride and 3,3',4,4'-biphenyl tetracarboxylic dianhydride or 2,2-bis(3,4-carboxyphenyl)hexafluoropropane dianhydride and benzidine derivatives which offer a combination of desirable properties including, low linear coefficient of thermal expansion, low moisture absorption, high glass transition temperature, low dielectric constant, and improved tensile elongation.Type: GrantFiled: October 29, 1991Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Brian C. Auman
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Patent number: 5260404Abstract: Polyetherketoneimides and copolymers thereof having an imide repeat unit of formula ##STR1## wherein Ri is ##STR2## in which A is a direct bond or --O--or another substantially non-electron-withdrawing group, and/or Ra is an at least partly arylene moiety other than m- or P-phonylene.These polymers tend to have improved melt stability and other properties, especially when made from a pre-existing imide monomer, instead of by the known amic acid route which results in uncyclised amic acid residues in the polymer.Type: GrantFiled: July 24, 1992Date of Patent: November 9, 1993Assignee: Raychem LimitedInventors: Richard Whiteley, Christopher Borrill
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Patent number: 5260388Abstract: A heat-resistant and thermoplastic polyimide which has low dielectric characteristics and recurring structural units of the following formula ##STR1## wherein R is a tetravalent radical having from 2 to 27 carbon atoms and selected from the group consisting of an aliphatic radical, alicyclic radical, monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected each other with a direct bond or a bridge member; aromatic diamines which are useful for the raw material monomers of the polyimide and have following formulas: ##STR2## and ##STR3## and a process for preparing the polyimide of the above formula by reacting these aromatic diamines with a tetracarboxylic dianhydride in the presence of an aromatic dicarboxylic anhydride or aromatic monoamine, and successively thermally or chemically imidizing the resultant polyamic acid.Type: GrantFiled: June 8, 1992Date of Patent: November 9, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Wataru Yamashita, Yuichi Okawa, Yuko Ishihara, Keizaburo Yamaguchi, Akihiro Yamaguchi
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Patent number: 5260412Abstract: A terminal-modified imide oligomer composition, comprising(A) 100 parts by weight of a terminal-modified imide oligomer obtained by a reaction in a solvent of a biphenyltetracarboxylic acid compound with an aromatic diamine compound and a monoamine compound containing a carbon-carbon triple bond, and having an unsaturated terminal group at the terminal of the oligomer and an imide bond in the oligomer, and having a logarithmic viscosity number at 30.degree. C., as determined at a concentration of 0.5 g/100 ml of N-methyl-2-pyrrolidone as a solvent, of from 0.1 to 1 and;(B) 5 to 180 parts by weight of an unsaturated imide compound obtained by a reaction in a solvent of a substituent-containing nadic anhydride with a monoamine compound having a carbon-carbon triple bond in an equimolar ratio, and having an unsaturated terminal group at the terminal thereof and an imide bond therein.Type: GrantFiled: September 24, 1990Date of Patent: November 9, 1993Assignee: Ube Industries, Ltd.Inventors: Shinji Yamamoto, Hideho Tanaka, Kazuyoshi Fujii
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Patent number: 5260407Abstract: A polyimide film essentially consisting of polyimide having recurring units of the formula (I): ##STR1## which has a density of 1.335 to 1.390 g/cm.sup.3 at 23.degree. C. and/or a refractive index of 1.605 to 1.680 at 23.degree. C. in the direction of thickness and is transparent; and a preparation process of the polyimide film by extruding the polyimide having recurring units of the above formula (I) through a common melt-extrusion process, casting in a chill-roller to obtain an unstretched film, uniaxially or biaxially stretching the unstretched film to cause molecular orientation, and successively setting the stretched film through heat-treatment.Type: GrantFiled: July 9, 1990Date of Patent: November 9, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masumi Saruwatari, Yasuhiko Ohta, Yasuhiro Fujii, Yasuko Honji, Shoichi Tsuji, Shinobu Moriya
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Patent number: 5260413Abstract: An aromatic polyimide film coated with a thermally stable, heat-sealable thermoplastic polyimide for use as a wire insulation for superconducting magnets is disclosed. The inclusion of inorganic particles in the film improves compressive strength of the coated polyimide film.Type: GrantFiled: March 12, 1992Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: James P. Ochsner, Darrell J. Parish
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Patent number: 5248760Abstract: The invention comprises curing polyamic acid solutions into polyimide solutions by adding a hydrophilic reagent to a polyamic acid solution. The hydrophilic reagent is selected to have little or no reactivity with amines or carboxylic acids, and is of the type that will react with water to form by-products that shift the equilibrium between polyamic acid as a reactant and polyimide and water as products toward the production of polyimide.Type: GrantFiled: January 25, 1991Date of Patent: September 28, 1993Assignees: UNC at Charlotte, MCNCInventors: Thomas D. DuBois, Farid M. Tranjan, Stephen M. Bobbio
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Patent number: 5247060Abstract: Curing of phthalonitrile monomers and prepolymers is accelerated by inclusion of an acid curing agent. Cured phthalonitrile polymers have high thermal oxidative stability and are useful as resins in various compositions and as adhesives.Type: GrantFiled: January 9, 1992Date of Patent: September 21, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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Patent number: 5247057Abstract: A polymer which can undergo thermally-induced transformation to provide a reinforcing component and a matrix component. This polymer has repeating units of the formula: ##STR1## wherein Z is selected from the group consisting of dialkyl amino thermoplastic moieties and dialkyl amino moieties which can undergo insitu reaction to form a thermoset. Dialkyl amino moieties which can undergo insitu reaction to form thermosets include the following: ##STR2## wherein Q is ##STR3## R is --CH.sub.3 or Q and a has a value of 1 to 3. Dialkyl amino thermoplastic moieties include the following: ##STR4##The invention described herein may be manufactured and used by or for the Government of the United States for all governmental purposes without the payment of any royalty.Type: GrantFiled: March 23, 1992Date of Patent: September 21, 1993Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Loon-Seng Tan, Fred E. Arnold
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Patent number: 5243024Abstract: Improved imide-containing copolymers comprising, in the aromatic diamine component, p-phenylene diamine and at least one additional aromatic diamine have increased rigidity and useful processability. The copolymers of this invention also may exhibit improved resistance to the detrimental effects of humid environments and retain mechanical properties at elevated temperatures after exposure to humid environments.Type: GrantFiled: December 21, 1990Date of Patent: September 7, 1993Assignee: Amoco CorporationInventors: Ronald E. Bockrath, Edward J. Gordon