Phosphorus- Or Sulfur-containing Reactant Patents (Class 528/352)
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Patent number: 5025084Abstract: A polyimide-forming composition comprising(A) a polycarboxylic acid partial ester of formulaHOOC--R.sup.1 --COOR.sup.2 Iwhere R.sup.1 denotes a divalent ethylenically unsaturated aliphatic or cycloaliphatic group of 2 to 20 carbon atoms, and R.sup.2 denotes the residue, after removal of a hydroxyl group, of an alcohol having from 4 to 20 carbon atoms which has a cycloaliphatic, aromatic or heterocyclic ring and is polymerizable on heating in the presence of an acid,(B) a partial ester of formula I above in which R.sup.1 denotes a group of formula II ##STR1## where Ar.sup.1 denotes a tetravalent aromatic group of 6 to 20 carbon atoms linked through aromatic carbon atoms thereof to the indicated carbon atoms, and R.sup.2 is as defined above,(C) an aromatic primary polyamine and(D) a heat-activable substance which releases an acid at a temperature of 100.degree. C. or above.Type: GrantFiled: July 10, 1990Date of Patent: June 18, 1991Assignee: Ciba-Geigy CorporationInventors: Bryan Dobinson, Mark R. Southcott
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Patent number: 5004575Abstract: Composite materials with matrices of tough, thermoplastic aromatic polyimides are obtained by blending semi-crystalline polyimide powders with polyamic acid solutions to form slurries, which are used in turn to prepare prepregs, the consolidation of which into finished composites is characterized by excellent melt flow during processing.Type: GrantFiled: October 21, 1988Date of Patent: April 2, 1991Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Norman J. Johnston, Terry L. St. Clair, Robert M. Baucom, John R. Gleason
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Patent number: 4997869Abstract: In humid atmospheres (e.g., 40% relative humidity or above) solutions of 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride/2,2-bis[4-(aminophenoxy)phenyl]hexafluoropropane polyimides tend to be unstable in the sense that during spin coating operations undesirable precipitate formation occurs on the rotating surface of the wafer. The result is the formation of unacceptable coatings due to their irregularity and lack of uniformity. Described are solutions of these polyimide polymers in a solvent containing one or more liquid aromatic hydrocarbons having a boiling point of at least about 110.degree. C. and one or more dipolar aprotic solvents having a boiling point of at least about 150.degree. C., such that the solution (a) contains on a weight basis from about 5% to about 50% of the polyimide, and (b) does not undergo precipitate formation during spin coating in an atmosphere of at least up to about 55% relative humidity.Type: GrantFiled: October 11, 1988Date of Patent: March 5, 1991Assignee: Ethyl CorporationInventors: Allan A. Eisenbraun, Wesley C. Blocker
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Patent number: 4996293Abstract: This invention provides:A. A polyimide resin composition which comprises at least one polyimide having a repeating unit of the general formula ##STR1## wherein Z is --S--, ##STR2## in which X is --O--, --S-- or ##STR3## Y is a single chemical bond or a bivalent group selected from the group consisting of --O--, --S--, --SO.sub.2 --, ##STR4## and --CO--, and R.sup.1 and R.sup.2 are the same or different and each independently is a hydrogen atom, a halogen atom or a lower alkyl group which may optionally be substituted by a halogen atom or atoms, and having an inherent viscosity (.eta..sub.inh) of about 0.3- about 5.0 dl/g, the polyimide being dissolved in an organic solvent, and a method of producing such composition andB. A polyimide resin composition which is otherwise the same as the above composition but further contains a silane coupling agent added thereto, and a method of producing such composition.Type: GrantFiled: October 12, 1988Date of Patent: February 26, 1991Assignee: New Japan Chemical Co., Ltd.Inventor: Ikeda Tsuyoshi
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Patent number: 4996254Abstract: In human atmospheres (e.g., 55% relative humidity or above) solutions of 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride/2,2-bis[4-(aminophenoxy)phenyl]hexafluoropropane polyamic acid polymers tend to be unstable in the sense that during spin coating operations undesirable precipitate formation may occur on the rotating surface of a semiconductor wafer. The result is the formation of unacceptable coatings due to their irregularity and lack of uniformity. Described are solutions of these polyamic acid polymers in a solvent containing one or more cycloaliphatic ketones, such that the solution (a) contains on a weight basis from about 5% to about 40% of the polyamic acid and (b) does not undergo precipitate formation during spin coating in an atmosphere of up to at least about 55% relative humidity.Type: GrantFiled: October 11, 1988Date of Patent: February 26, 1991Assignee: Ethyl CorporationInventors: Allan A. Eisenbraun, Wesley C. Blocker
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Patent number: 4994544Abstract: A process for the production of polyimide fibers and polyimide fibers obtained by the process. The process includes thermal or chemical imidation of a polyamic acid which has been obtained by reacting a specific diamine and a particular tetracarboxylic dianhydride in the presence of a dicarboxylic anhydride represented by the following formula: ##STR1## wherein Z represents a divalent group selected from the group consisting of monocyclic aromatic groups, fused polycyclic aromatic groups and non-fused polycyclic aromatic groups with aromatic rings bonded together directly or via a crosslinking member.Type: GrantFiled: November 6, 1989Date of Patent: February 19, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Taizo Nagahiro, Masahiro Ohta, Shuichi Morikawa, Nubohito Koga, Shoji Tamai
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Patent number: 4988795Abstract: An amphiphilic polyimide precursor having at least 70% by mole of the recurring unit of the formula (1): ##STR1## wherein R.sup.1 is a tetravalent group having at least 2 carbon atoms, R.sup.2 is a bivalent group having at least 2 carbon atoms, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen atom or a monovalent group having 1 to 30 carbon atoms selected from an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an alicyclic group or an aromatic group, and their groups substituted by a halogen atom, nitro group, amino group, cyano group, methoxy group or acetoxyl group, provided that at least one, preferably at least two, of R.sup.3, R.sup.4, R.sup.5 and R.sup.Type: GrantFiled: September 7, 1989Date of Patent: January 29, 1991Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4987197Abstract: This invention relates to molding resin compositions, and more particularly relates to polyimide resin compositions having markedly improved molding ability in addition to excellent high temperature stability, chemical resistance and mechanical strength.The polyimide resin compositions of this invention comprises 99.9 to 50.0% by weight of the polyimide and 0.1 to 50.0% by weight of aromatic polyamideimide.Type: GrantFiled: April 24, 1989Date of Patent: January 22, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masahiro Ohta, Saburo Kawashima, Katsuaki Iiyama, Shoji Tamai, Hideaki Oikawa, Akihiro Yamaguchi
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Patent number: 4987219Abstract: A copolymeric amphiphilic polyimide precursor having the recurring unit of the formula (1): ##STR1## wherein R.sup.1 is a tetravalent group having at least 2 carbon atoms, R.sup.2 is a bivalent group having at least 2 carbon atoms, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen atom or a monovalent group having 1 to 30 carbon atoms selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an aromatic group, or an alicyclic group, and their groups substituted by a halogen atom, nitro group, amino group, cyano group, methoxy group or acetoxyl group, provided that at least one of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is neither hydrogen atom nor the above-mentioned group which has 1 to 11 carbon atoms; a part of at least one of said R.sup.1 and said R.sup.2 being substituted with a group having a valence different therefrom.Type: GrantFiled: April 22, 1987Date of Patent: January 22, 1991Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4980453Abstract: Macrocyclic oligomers, including polycarbonates, polyesters, polyamides, polyimides, polyetherketones and polyethersulfones, are conveniently prepared from various spiro(bis)indane compounds, especially the 6,6'-difunctional 3,3',3'-tetramethylspiro(bis)indanes. The macrocyclic oligomers may be conveniently converted to linear polymers.Type: GrantFiled: January 20, 1988Date of Patent: December 25, 1990Assignee: General Electric CompanyInventors: Daniel J. Brunelle, Thomas L. Guggenheim, James A. Cella, Thomas L. Evans, Luca P. Fontana, Gary R. Faler, James M. Fukuyama, Eugene P. Boden, Jonathan D. Rich, Thomas G. Shannon, Sharon J. McCormick, Philip J. McDermott, Alice M. Colley, Joseph W. Guiles
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Patent number: 4973662Abstract: A compound represented by the following general formula [1]: ##STR1## wherein R.sub.3 and R.sub.4 are independently selected from hydrogen and alkyl groups having 1 to 4 carbon groups,is valuable as an endcapping agent for a polyimide. Namely, a PMR polyimide varnish comprising this compound, a dialkyl tetracarboxylate represented by the following general formula [2]: ##STR2## wherein R.sub.1 is a direct bond or stands for CH.sub.2, O, CO, SO.sub.2, S or C(CH.sub.3).sub.2 and X stands for an alkyl group having 1 to 4 carbon atoms,and a diamine represented by the following general formula [3]: ##STR3## wherein R.sub.2 is a direct bond or stands for CH.sub.2, O, CO, SO.sub.2 S or C(CH.sub.3).sub.2,has a good storage stability and is especially valuable as a matrix resin to be incorporated in a fiber-reinforced composite material.Type: GrantFiled: September 8, 1988Date of Patent: November 27, 1990Assignee: Director General of Agency of Industrial Science and TechnologyInventors: Nobuyuki Odagiri, Kuniaki Tobukuro
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Patent number: 4966954Abstract: Production of polyenaminonitriles including those which can be cyclized to very stable poly(aminoquinolines) without the evolution of any small molecules and thus in a manner free of volatiles. The polyenaminonitriles are polymers which have desirable dielectric properties, and include those which can be cyclized to poly(aminoquinolines) without the evolution of volatiles to make defect-free films and composites of similar dielectric properties because of this characteristic.Type: GrantFiled: May 23, 1988Date of Patent: October 30, 1990Assignee: Rensselaer Polytechnic InstituteInventors: James A. Moore, Douglas Robello
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Patent number: 4963645Abstract: A terminal-modified imide oligomer having an unsaturated group as a terminal group and an imide bond inside of the oligomer which is produced by reacting 2,3,3',4'-or 3,3',4,4'-biphenyltetracarboxylic acid or its derivative, a diamine compound, and an unsaturated dicarboxylic acid or its derivative and/or an unsaturated monoamine in an organic solvent is disclosed. This oligomer has a logarithmic viscosity of not more than 1.0. This logarithmic viscosity is measured under the conditions of concentration of 0.5 g/100 ml-solvent (N-methyl-2-pyrrolidone) and a temperature of 30.degree. C., and has a melting point of 50.degree. to 300.degree. C.Type: GrantFiled: August 24, 1988Date of Patent: October 16, 1990Assignee: Ube Industries, Ltd.Inventors: Hiroshi Inoue, Tadao Muramatsu, Tetsuji Hirano
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Patent number: 4963647Abstract: The present invention provides novel heat stable polyamide-imide polymers having excellent flow properties which render them more readily processible into fibers, films, sheets and other molded articles. The polymers are prepared by forming the polycondensation product of one or more aromatic diamines and one or more trifunctional acid anhydride monomers, wherein at least one of said diamine monomers is a 12F-Diamine or 12F-Oxydiamine containing at least two CF.sub.3 ##STR1## R groups linking two aromatic moieties, wherein R is CF.sub.3 or phenyl. In addition to improved flow properties, the polyamide-imide polymers of this invention also exhibit improved solubility properties in most organic solvents, improved resistance to attack by chlorinated solvents such as trichloroethylene as compared with polyimides, improved hydrophobic properties as well as excellent thermal properties including resistance to thermooxidative degredation.Type: GrantFiled: February 27, 1989Date of Patent: October 16, 1990Assignee: Hoechst Celanese Corp.Inventors: Rohitkumar H. Vora, Paul N. Chen, Sr., Jeffrey S. Devolve
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Patent number: 4962183Abstract: The present invention provides novel heat stable polyamide-imide polymers having excellent flow properties and moisture stability which render them more readily processible into fibers, films, sheets and other molded articles. The polymers are prepared by forming the polycondensation product of one or more aromatic diamines, one or more tetrafunctional aromatic dianhydrides, and a difunctional aromatic carboxylic acid or amide-forming derivative thereof containing the groups ##STR1## linking two aromatic moieties, wherein R is CF.sub.3 or phenyl. In addition to improved flow properties, the polyamide-imide polymers of this invention also exhibit improved solubility properties in most organic solvents, improved resistance to attack by chlorinated solvents such as trichloroethylene as compared with polyimides, improved hydrophobic properties as well as excellent thermal properties, including resistance to thermooxidative degradation.Type: GrantFiled: May 8, 1989Date of Patent: October 9, 1990Assignee: Hoechst Celanese Corp.Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
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Patent number: 4959454Abstract: Linear polyethersulfones are prepared by ring-opening of a macrocyclic spirobiindane polyethersulfone oligomer composition. The ring-opening reaction is conducted in the presence of a basic reagent such as an alkali metal bisphenol salt, at a temperature in the range of about 300.degree.-400.degree. C.Type: GrantFiled: May 19, 1989Date of Patent: September 25, 1990Assignee: General Electric CompanyInventor: James M. Fukuyama
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Patent number: 4954608Abstract: A copolymerized polyamic acid salt having a recurring unit represented by following formula (I) and (II) and the process for preparing thereof. ##STR1## wherein (A) or (A') represents a formula ##STR2## wherein, R.sup.1 represents a tetravalent group having at least 2 carbon atoms; R.sup.2 represents a divalent group having at least 2 carbon atoms; and R.sup.31, R.sub.32, R.sup.33, R.sup.41, R.sup.42, R.sup.43, R.sup.5, and R.sup.6 each represents a monovalent group having 1 to 30 carbon atoms selected from an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an alicyclic group or an aromatic group, each of these groups substituted by a halogen atom, a nitro group, an amino group, a cyano group, a methoxy group, or an acetoxy group, or a hydrogen atom; at least one of said R.sup.31, R.sup.32, R.sup.33, R.sup.41, R.sup.42, R.sup.43, R.sup.5 and R.sup.Type: GrantFiled: June 1, 1987Date of Patent: September 4, 1990Assignee: Kanegafuchi Kagaku Kogyo KabushikiInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4954610Abstract: The present invention provides novel heat stable polyamide-imide polymers having excellent flow properties which render them more readily processible into fibers, films, sheets and other molded articles. The polymers are prepared by forming the polycondensation product of one or more aromatic diamines and one or more trifunctional acid anhydride monomers, at least one of said diamine monomers containing the group ##STR1## linking two aromatic moieties, wherein R is CF.sub.3 or phenyl. In addition to improved flow properties, the polyamide-imide polymers of this invention also exhibit improved solubility properties in most organic solvents, improved resistance to attack by chlorinated solvents such as trichloroethylene as compared with polyimides, improved hydrophobic properties as well as excellent thermal properties including resistance to thermooxidative degradation.Type: GrantFiled: February 27, 1989Date of Patent: September 4, 1990Assignee: Hoechst Celanese Corp.Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
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Patent number: 4954611Abstract: The present invention provides for shaped articles made from novel heat stable polyamide-imide polymers having excellent flow properties which render them more readily processible into fibers, films, sheets and other molded articles. The polymers are prepared by forming the polycondensation product of one or more aromatic diamines, one or more trifunctional acid anhydride monomers, and one or more tetrafunctional aromatic dianhydrides, at least one of said monomers containing the groups ##STR1## linking two aromatic moieties, wherein R is CF.sub.3 or phenyl. In addition to improved flow properties, the polyamide-imide polymers of this invention also exhibit improved solubility properties in most organic solvents, improved resistance to attach by chlorinated solvents such as trichloroethylene as compared with polyimides, improved hydrophobic properties as well as excellent thermal properties including resistance to thermooxidative degradation.Type: GrantFiled: February 27, 1989Date of Patent: September 4, 1990Assignee: Hoechst Celanese Corp.Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
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Patent number: 4954612Abstract: A solvent-soluble polyimide obtained from an exo-form dicarboxylic acid anhydride with an aromatic diamine, e.g. 2,2,-bis[4-(4-aminophenoxy)phenyl]propane is improved in film-forming properties and transparency, and particularly suitable for producing an orientation controlling film in a liquid crystal display device.Type: GrantFiled: February 14, 1989Date of Patent: September 4, 1990Assignee: Hitachi Chemical Co., Ltd.Inventors: Yoshihiro Nomura, Kazuhito Hanabusa, Hiroshi Minamisawa, Takashi Morinaga, Toichi Sakata, Yoshiyuki Mukoyama, Hiroshi Nishizawa, Hiromu Miyajima
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Patent number: 4952666Abstract: Polyimide polymers having a relatively low dielectric constant and good solvent resistance, are formed by polymerization of a polyimide oligomer having the formula ##STR1## wherein R is selected from the group consisting of: --C.tbd.CH,--CH.dbd.CH.sub.2,--CN, and ##STR2## wherein R.sub.1 is --H or --CH.sub.3, and n=1-20. Preferably R is an acetylene group. These polymers may also be formed from the corresponding polyamic acid oligomers.These polymers are useful for forming dielectric layers, particularly in multilayer semiconductor devices.Type: GrantFiled: May 6, 1988Date of Patent: August 28, 1990Assignee: Hughes Aircraft CompanyInventor: Abraham L. Landis
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Patent number: 4939214Abstract: A film comprised of at least one monomolecular layer composed essentially of a polyimide having repeating units of the formula: ##STR1## wherein R.sup.1 is a tetravalent organic group and R.sup.2 is a bivalent organic group.Type: GrantFiled: November 17, 1986Date of Patent: July 3, 1990Assignees: Mitsubishi Kasei Corporation, Yoshio Imai, Taro HinoInventors: Yoshio Imai, Taro Hino, Mitsumasa Iwamoto, Masa-aki Kakimoto, Masa-aki Suzuki, Toru Konishi
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Patent number: 4935490Abstract: Aromatic polyimides of the formula: ##STR1## where --Ar-- is ##STR2## --Ar'-- is ##STR3## --Ar"-- is ##STR4## where --Z, and --Z.sub.1, independently are --Cl, --Br or --I; where --X, --X.sub.1, --X.sub.2 and --X.sub.3 independently are --CH.sub.3 or --C.sub.2 H.sub.5 ; and --Y,--Y.sub.1,--Y.sub.2 and --Y.sub.3 are primary or secondary alkyl groups having 3 to 12 carbon atoms, provided that when m is greater than 0, r is 0 and that when L is greater than 0, r and s are 0, are disclosed. These polyimides are very soluble, even in weak solvents such as toluene.Type: GrantFiled: April 13, 1988Date of Patent: June 19, 1990Assignee: E. I. DuPont de Nemours and CompanyInventor: Richard A. Hayes
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Patent number: 4931540Abstract: This invention relates to new fluorine-containing polyimides, polyamide-acids/esters, polyamides, addition polyimides and imide oligomers which exhibit low melting points, better solubilities, low dielectric constants, superior thermal and thermal oxidative stability, and improved processing characteristics.The products of this invention are characterized by the fact that they are derived from 4,4'-bis[2-(3,4-(dicarboxyphenyl)hexafluoroisopropyl]diphenyl ether dianhydride.Type: GrantFiled: November 24, 1987Date of Patent: June 5, 1990Assignee: Hoechst Celanese CorporationInventors: Werner H. Mueller, Dinesh N. Khanna, Rohitkumar H. Vora, Ruediger J. Erckel
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Patent number: 4923968Abstract: A crystalline polyimide polymer having a practical effectiveness that extrusion or injection molding which has so far been applied to thermoplastic resins, but could not have been achieved by conventional polyimides, are possible due to its melting point in the range of 300.degree. C. to 450.degree. C., and a process for producing the polymer, are provided, which polyimide polymer contains the following imide repetition unit (I) in 30% by mol based on the polymer and containing or not containing at least one of other imide repetition units and also having an inherent viscosity of 0.1 to 5 dl/g in conc. sulfuric acid at 30.+-.0.01.degree. C.: ##STR1## wherein X is divalent CO, divalent SO.sub.2 group, S, O or a single bond.Type: GrantFiled: July 11, 1988Date of Patent: May 8, 1990Assignee: Chisso CorporationInventors: Kouichi Kunimune, Kazutsune Kikuta, Takao Kawamoto, Shiro Konotsune
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Patent number: 4923960Abstract: The present invention provides novel heat stable polyamide-imide polymers having excellent flow properties which render them more readily processible into fibers, films, sheets and other molded articles. The polymers are prepared by forming the polycondensation product of one of more aromatic diamines, one or more trifunctional acid anhydride monomers, and one or more tetrafunctional aromatic dianhydrides, at least one of said monomers containing the groups ##STR1## linking two aromatic moieties, wherein R is CF.sub.3 or phenyl. In addition to improved flow properties, the polyamide-imide polymers of this invention also exhibit improved solubility properties in most organic solvents, improved resistance to attack by chlorinated solvents such as trichloroethylene as compared with polyimides, improved hydrophobic properties as well as excellent thermal properties including resistance to thermooxidative degradation.Type: GrantFiled: February 27, 1989Date of Patent: May 8, 1990Assignee: Hoechst Celanese Corp.Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
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Patent number: 4914181Abstract: Polyimides which essentially consist of 0.1 to 100 mol % of at least one structural element of the formula I ##STR1## and 99.9 to 0 mol % of at least one structural element of the formula II and/or III ##STR2## in which Z and Z' are a tetravalent aromatic radical, Q' is a trivalent aromatic radical, X and X' are a divalent radical of an organic amine, are autophotocrosslinkable. They are suitable for the production of protective films and photographic relief images.Type: GrantFiled: July 6, 1987Date of Patent: April 3, 1990Assignee: Ciba-Geigy CorporationInventors: Josef Pfeifer, Rudolf Duthaler
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Patent number: 4914175Abstract: In one embodiment this invention provides injection moldable polyimides, as exemplified by the condensation and imidization product of a aromatic dianhydride such as 2,2-bis(3,4-dicarboxyphenyl)propane dianhydride with a novel aromatic diamine such as 2,2-bis[p,p'-(m-aminophenoxy)phenylsulfonyl(p-phenyleneoxy)phenyl]propane.Type: GrantFiled: May 10, 1988Date of Patent: April 3, 1990Assignee: Hoechst Celanese Corp.Inventor: Eui W. Choe
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Patent number: 4910293Abstract: An amphiphilic high polymer comprises a linear recurring unit containing at least divalent organic group (R.sub.1) having at least two carbon atoms, at least divalent organic group (R.sub.2) having at least two carbon atoms, and at least one C.sub.10-30 hydrocarbon-containing group (R.sub.3) which may have one or more substituent groups, said organic groups R.sub.1 and R.sub.2 being connected to each other by a divalent connecting group, and said hydrocarbon-containing group R.sub.3 being boned to said recurring unit by a covalent bond, and the method for producing the same comprises polycondensating a combination of monomers containing R.sub.1 and R.sub.2.Type: GrantFiled: October 11, 1988Date of Patent: March 20, 1990Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4906730Abstract: A method is provided for enhancing the crystallization rate of certain polyetherimide to provide an improved molding mehod for making solvent resistant shaped thermoplastics. Polyetherimide blends containing crystallization rate enhancing agents such as bisimides or imide oligomers also are provided.Type: GrantFiled: May 6, 1988Date of Patent: March 6, 1990Assignee: General Electric CompanyInventors: Tohru Takekoshi, Patricia P. Anderson
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Patent number: 4902740Abstract: A polyamideimide having an inherent viscosity of above 0.48 which comprises a unit of the following formula (II) ##STR1## and a unit of the following formula (IV) ##STR2## as main units forming the molecular chains of the polyamideimide, and an intimate mixture of the polyamideimide and a plasticizing material for the polyamideimide.Type: GrantFiled: November 8, 1988Date of Patent: February 20, 1990Assignee: Teijin LimitedInventors: Shigeyoshi Hara, Hiroo Inata, Shunichi Matsumura
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Patent number: 4897461Abstract: An amphiphilic polyimide precursor having at least 70% by mole of the recurring unit of the formula (1): ##STR1## wherein R.sup.1 is a tetravalent group having at least 2 carbon atoms, R.sup.2 is a bivalent group having at least 2 carbon atoms, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen atom or a monovalent group having 1 to 30 carbon atoms selected from an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an alicyclic group or an aromatic group, and their groups substituted by a halogen atom, nitro group, amino group, cyano group, methoxy group or acetoxyl group, provided that at least one, preferably at least two, of R.sup.3, R.sup.4, R.sup.5 and R.sup.Type: GrantFiled: June 29, 1988Date of Patent: January 30, 1990Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4895972Abstract: Linear aromatic polyimides with low dielectric constants are produced by adding a diamic acid additive to the polyamic acid resin formed by the condensation of an aromatic dianhydride with an aromatic diamine. The resulting modified polyimide is a better electrical insulator than state-of-the-art commercially available polyimides.Type: GrantFiled: September 1, 1988Date of Patent: January 23, 1990Assignee: The United States of American as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Diane M. Stoakley, Anne K. St. Clair
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Patent number: 4886873Abstract: An aromatic hetero ring-containing polyimide comprising substantially equal equivalent amount of (1) structural units of Group 1 and (2) structural units of Group 2, wherein the structural units of Group 1 comprise (i) from 30 to 100 mol % of a unit of the formula: ##STR1## wherein X is S, O or NH, and (ii) from 0 to 70 mol % of a unit of the formula: ##STR2## wherein Ar.sub.1 is ##STR3## wherein each of y, y.sub.1, and y.sub.2 and y.sub.3 is a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and each of Z, Z.sub.1 and Z.sub.2 is a single bond, --O--, --CH.sub.2 --, ##STR4## --C--, --SO.sub.2 --, --C(CH.sub.3).sub.2 -- or --C(CF.sub.3).sub.2, and the structural units of Group 2 comprise (i) from 70 to 100 mol % of a unit of the formula: ##STR5## and (ii) from 0 to 30 mol % of a unit of the formula: ##STR6## wherein Ar.sub.2 is ##STR7## wherein Z, y and y.sub.Type: GrantFiled: March 7, 1988Date of Patent: December 12, 1989Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Seiichi Mukai, Masatoshi Kimura, Shohachi Morita
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Patent number: 4883858Abstract: A premix, an origomeric prepolymer obtainable from a limited addition polymerization effected with the premix and a thermosetting resin obtainable from such premix or prepolymer as well as fiber reinforced plastics made of such thermosetting resin which are excellent in the heat resistance, impact resistance and flexibility and exhibit a high toughness, wherein said premix comprises, as a first essential component, an amine-terminated amic acid expressed by the formula, ##STR1## in which R.sup.1 stands for a tetravalent aromatic residue having 6 to 20 carbon atoms and R.sup.2 denotes a divalent organic residue having 2 to 20 carbon atoms, said amic acid being produced by reacting a tetracarboxylic dianhydride with a diamine compound, and, as a second essential component, an N,N'-bis maleimide of the formula, ##STR2## wherein R.sup.3 denotes a divalent organic residue having 2 to 20 carbon atoms, the mole ratio of [N,N'-bismaleimide]/[amine-terminated amic acid] being in the range from 1 to 3.Type: GrantFiled: August 19, 1988Date of Patent: November 28, 1989Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Masayuki Takemoto, Osamu Nagura, Yukio Nomura, Minoru Yasuda
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Patent number: 4877653Abstract: A method of insolubilizing solvent soluble polyimides comprising the imidized condensation products of an aromatic dianhydride and a primary aromatic diamine wherein at least one of said dianhydride or diamine is selected from the group consisting of 2,2-hexafluoro-bis(3,4-dicarboxyphenyl)propane dianhydride; 2,2-hexafluoro-bis(3-aminophenyl) propane; 2,2-hexafluoro-bis(4-aminophenyl)propane; 2,2-hexafluoro-bis-[4-(3-aminophenoxy)phenyl]propane; 2,2-hexafluoro-bis[4-(4-aminophenoxy)phenyl]propane; 1,1-bis(4-aminophenyl)-1-phenyl-2,2,2-trifluoroethane; 1,1-bis-[4-(1,2-dicarboxyphenyl)]-1-phenyl-2,2,2-trifluoroethane dianhydride and mixtures thereof.The method comprises forming a shaped article or film comprising the polyimides and subjecting same to a heat annealing process at a temperature of at least 325.degree. C. and for a period of time sufficient to insolubilize the polyimide. Preferred temperatures range from 350.degree. C. to 400.degree. C. for a period of time of at least 45 minutes to about 2 hours.Type: GrantFiled: July 12, 1988Date of Patent: October 31, 1989Assignee: Hoechst Celanese CorporationInventors: Rohitkumar H. Vora, Dinesh N. Khanna, Suzanne Fontaine
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Patent number: 4864015Abstract: A method is provided for making 9,10-dithiaanthracene-2,3,6,7-tetracarboxylic acid dianhydride. Polyimides having improved oxidative stability also are provided which can be made intercondensing organic diamine and the aforementioned dianhydride or a dianhydride mixture.Type: GrantFiled: November 21, 1988Date of Patent: September 5, 1989Assignee: General Electric CompanyInventors: James A. Cella, Deborah A. Haitko
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Patent number: 4857079Abstract: A novel co-poly (imide ether) copolymer consisting essentially of an organic acid dianhydride, a diamine, and a diaminated polyether, wherein the percentage of the diaminated polyether in the total amount of the diamine and the diaminated polyether is 5 to 40% by weight.Type: GrantFiled: April 7, 1988Date of Patent: August 15, 1989Assignee: TOA Nenryo Kogyo K.K.Inventor: Yoshiharu Kimura
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Patent number: 4851506Abstract: The present invention relates to compositions comprising(a) at least one polyimide having an inherent viscosity of at least 0.1 dl/g (measured at 25.degree. C. on a 0.5% by weight solution in N-methylpyrrolidone) and containing at least 50 mol % of structural units of the formula I ##STR1## in which m and p independently of one another are integers from 0 to 4, n is an integer from 0 to 3, R.sup.1 and R.sup.2 independently of one another are C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy and R.sup.3 is a divalent radical of an aromatic diamine which is substituted in at least one ortho-position relative to at least one N atom by alkyl, alkoxy, alkoxyalkyl, cycloalkyl or aralkyl or in which two adjacent C atoms of the aromatic radical are substituted by alkylene, and(b) at least one aromatic polyimide which is soluble in organic solvents and photocrosslinkable and which contains at least 50 mol %, relative to the total quantity of diamine units, of radicals R.sup.Type: GrantFiled: December 21, 1987Date of Patent: July 25, 1989Assignee: Ciba-Geigy CorporationInventors: Ottmar Rohde, Andre-Etienne Perret, Josef Pfeifer
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Patent number: 4851505Abstract: Highly soluble, optically transparent aromatic polyimides of the following formula are disclosed: ##STR1## where --X and --X.sub.1 are independently primary or secondary alkyl groups having 1 to 6 carbon atoms,--X is different than --X.sub.1,--Y is independently --H, or --Z,--Z is independently --Cl, --Br or --I,r=0-100% of r+t, ands=100%t=100% -r of r+t are disclosed.Type: GrantFiled: April 13, 1988Date of Patent: July 25, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard A. Hayes
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Patent number: 4847358Abstract: There are disclosed a process for producing a polyamide acid having at least one siloxane bond, which comprises carrying out the reaction of:(a) a tetracarboxylic dianhydride having at least one siloxane bond of the formula: ##STR1## wherein R represents a monovalent hydrocarbon group and m is an integer of 1 or more;(b) a diamine; and(c) a diaminoamide compound of the formula (II): ##STR2## wherein Ar represents an aromatic residue, Y represents SO.sub.2 or CO, and one amino group and Y--YNH.sub.Type: GrantFiled: August 18, 1987Date of Patent: July 11, 1989Assignee: Hitachi Chemical Company, Ltd.Inventors: Mitsumasa Kojima, Takayuki Saito, Toul Kikuchi, Shun-ichiro Uchimura, Hidetaka Satou, Daisuke Makino
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Patent number: 4847359Abstract: Compounds containing at least 5 mol % of structural units of the formulae I and/or II ##STR1## in which Q is an unsubstituted or substituted tetravalent aromatic radical to which in each case two carbonyl groups are bonded in the ortho- or peri-position, R.sup.1 is selected from the radicals of the formulae III, IV and V ##STR2## R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are hydrogen, alkyl, cycloalkyl or substituted or unsubstituted aryl or aralkyl, R.sup.6 and R.sup.7 are aryl or halogen, m and n are 0, 1 or 2 and o is 0, 1, 2, 3 or 4, are described.The compounds are distinguished by an increased resistance to oxidation by heat. They can be used to produce coatings and relief structures.Type: GrantFiled: June 19, 1987Date of Patent: July 11, 1989Assignee: Ciba-Geigy CorporationInventors: Josef Pfeifer, Rudolf Duthaler
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Patent number: 4845167Abstract: A condensation polyimide containing a 1,1,1-triaryl-2,2,2-trifluoroethane structure, other related condensation polyimides and process for their preparation, which comprises polymerization of a cyclic dianhydride with a diamine.Type: GrantFiled: October 29, 1986Date of Patent: July 4, 1989Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: William B. Alston, Roy F. Gratz
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Patent number: 4837299Abstract: A process for making thermoplastic polyimides which involves reacting an aromatic dianhydride with an organic diamine in the presence of a tertiary amine in an inert solvent to form a polyamide acid salt; separating the polyamide acid salt from the solvent; and heating the polyamide acid salt under imidization conditions to form the desired polyimide.Type: GrantFiled: December 31, 1986Date of Patent: June 6, 1989Assignee: General Electric CompanyInventors: Edward N. Peters, Michael W. Schultz
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Patent number: 4837300Abstract: Novel copolyimides are prepared by reacting one or more aromatic dianhydrides with a meta-substituted phenylene diamine and an aromatic bridged diamine. The incorporation of meta-substituted phenylene diamine derived units and bridged aromatic diamine derived units into the linear aromatic polymer backbone results in a copolyimide of improved flexibility, processability, and melt-flow characteristics. The novel copolyimides are especially useful as thermoplastic hot-melt adhesives.Type: GrantFiled: July 9, 1987Date of Patent: June 6, 1989Assignee: The United States of America as represented by the Administration of the National Aeronautics and Space AdministrationInventors: Terry L. St. Clair, Harold D. Burks, Donald J. Progar
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Patent number: 4837298Abstract: Cyclic imides are prepared by the reaction of a bis(dicarboxyphenyl) sulfide or functional derivative thereof, and optionally a second tetracarboxylic acid or functional derivative thereof such as 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride, with a diamine having a spirobiindane nucleus. The cyclic imides may be converted to linear polyimides by reaction with a basic alkali metal sulfide.Type: GrantFiled: June 22, 1987Date of Patent: June 6, 1989Assignee: General Electric CompanyInventors: James A. Cella, Thomas L. Guggenheim
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Patent number: 4835249Abstract: A process for making certain polyimides involves dissolving substantially equimolar amounts of an aromatic dianhydride and an organic diamine in a high-boiling, aprotic solvent, heating the reaction solution to form an insoluble polyimide prepolymer and to distill out water of reaction, separating the solid polyimide prepolymer and melt polymerizing the polyimide prepolymer to form the desired polyimide.Type: GrantFiled: December 31, 1986Date of Patent: May 30, 1989Assignee: General Electric CompanyInventors: Patrick E. Gallagher, Ronald A. Greenberg
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Patent number: 4824932Abstract: The invention relates to aromatic polyamides and polyamidimides, and a method of manufacturing these by transamidation of aromatic biasmides of carboxylic acids, using aromatic di- and/or tricarboxylic acids or their anhydrides, in the melt, at temperatures between 220.degree. to 390.degree. C.Type: GrantFiled: December 30, 1986Date of Patent: April 25, 1989Assignee: Huls AktiengesellschaftInventors: Juergen Finke, Martin Bartmann
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Patent number: RE33079Abstract: Polyimides are prepared from acetylene substituted polyimide oligomers via an addition polymerization reaction which involves homopolymerization. These polymers exhibit low void content when cured and possess superior thermal stability characteristics and physical properties such as structural strength. One of their unique properties is their ability to be processed into useful articles at moderate pressures and temperatures.Type: GrantFiled: March 5, 1979Date of Patent: October 3, 1989Assignee: Hughes Aircraft CompanyInventors: Norman Bilow, Abraham L. Landis, Leroy J. Miller
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Patent number: RE33342Abstract: A liquid crystal aligning agent consisting essentially of a polyimide resin obtained by the polymerization of a diamine, a tetracarboxylic acid dianhydride and a monoamine of the formula:R.sup.2 (R.sup.1).sub.n NH.sub.2 (I)wherein R.sup.1 is a divalent organic group, R.sup.2 is an alkyl group having from 6 to 20 carbon atoms, and n is 0 or 1.Type: GrantFiled: September 1, 1988Date of Patent: September 18, 1990Assignee: Nissan Chemical Industries Ltd.Inventors: Noriaki Kohtoh, Toyohiko Abe, Hiroyoshi Fukuro