Phosphorus- Or Sulfur-containing Reactant Patents (Class 528/352)
  • Patent number: 5025084
    Abstract: 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: Grant
    Filed: July 10, 1990
    Date of Patent: June 18, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Bryan Dobinson, Mark R. Southcott
  • Patent number: 5004575
    Abstract: 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: Grant
    Filed: October 21, 1988
    Date of Patent: April 2, 1991
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Norman J. Johnston, Terry L. St. Clair, Robert M. Baucom, John R. Gleason
  • Patent number: 4997869
    Abstract: 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: Grant
    Filed: October 11, 1988
    Date of Patent: March 5, 1991
    Assignee: Ethyl Corporation
    Inventors: Allan A. Eisenbraun, Wesley C. Blocker
  • Patent number: 4996293
    Abstract: 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: Grant
    Filed: October 12, 1988
    Date of Patent: February 26, 1991
    Assignee: New Japan Chemical Co., Ltd.
    Inventor: Ikeda Tsuyoshi
  • Patent number: 4996254
    Abstract: 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: Grant
    Filed: October 11, 1988
    Date of Patent: February 26, 1991
    Assignee: Ethyl Corporation
    Inventors: Allan A. Eisenbraun, Wesley C. Blocker
  • Patent number: 4994544
    Abstract: 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: Grant
    Filed: November 6, 1989
    Date of Patent: February 19, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Taizo Nagahiro, Masahiro Ohta, Shuichi Morikawa, Nubohito Koga, Shoji Tamai
  • Patent number: 4988795
    Abstract: 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: Grant
    Filed: September 7, 1989
    Date of Patent: January 29, 1991
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 4987197
    Abstract: 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: Grant
    Filed: April 24, 1989
    Date of Patent: January 22, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masahiro Ohta, Saburo Kawashima, Katsuaki Iiyama, Shoji Tamai, Hideaki Oikawa, Akihiro Yamaguchi
  • Patent number: 4987219
    Abstract: 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: Grant
    Filed: April 22, 1987
    Date of Patent: January 22, 1991
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 4980453
    Abstract: 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: Grant
    Filed: January 20, 1988
    Date of Patent: December 25, 1990
    Assignee: General Electric Company
    Inventors: 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
  • Patent number: 4973662
    Abstract: 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: Grant
    Filed: September 8, 1988
    Date of Patent: November 27, 1990
    Assignee: Director General of Agency of Industrial Science and Technology
    Inventors: Nobuyuki Odagiri, Kuniaki Tobukuro
  • Patent number: 4966954
    Abstract: 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: Grant
    Filed: May 23, 1988
    Date of Patent: October 30, 1990
    Assignee: Rensselaer Polytechnic Institute
    Inventors: James A. Moore, Douglas Robello
  • Patent number: 4963645
    Abstract: 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: Grant
    Filed: August 24, 1988
    Date of Patent: October 16, 1990
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroshi Inoue, Tadao Muramatsu, Tetsuji Hirano
  • Patent number: 4963647
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: October 16, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Rohitkumar H. Vora, Paul N. Chen, Sr., Jeffrey S. Devolve
  • Patent number: 4962183
    Abstract: 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: Grant
    Filed: May 8, 1989
    Date of Patent: October 9, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
  • Patent number: 4959454
    Abstract: 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: Grant
    Filed: May 19, 1989
    Date of Patent: September 25, 1990
    Assignee: General Electric Company
    Inventor: James M. Fukuyama
  • Patent number: 4954608
    Abstract: 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: Grant
    Filed: June 1, 1987
    Date of Patent: September 4, 1990
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 4954610
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: September 4, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
  • Patent number: 4954611
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: September 4, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
  • Patent number: 4954612
    Abstract: 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: Grant
    Filed: February 14, 1989
    Date of Patent: September 4, 1990
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Yoshihiro Nomura, Kazuhito Hanabusa, Hiroshi Minamisawa, Takashi Morinaga, Toichi Sakata, Yoshiyuki Mukoyama, Hiroshi Nishizawa, Hiromu Miyajima
  • Patent number: 4952666
    Abstract: 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: Grant
    Filed: May 6, 1988
    Date of Patent: August 28, 1990
    Assignee: Hughes Aircraft Company
    Inventor: Abraham L. Landis
  • Patent number: 4939214
    Abstract: 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: Grant
    Filed: November 17, 1986
    Date of Patent: July 3, 1990
    Assignees: Mitsubishi Kasei Corporation, Yoshio Imai, Taro Hino
    Inventors: Yoshio Imai, Taro Hino, Mitsumasa Iwamoto, Masa-aki Kakimoto, Masa-aki Suzuki, Toru Konishi
  • Patent number: 4935490
    Abstract: 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: Grant
    Filed: April 13, 1988
    Date of Patent: June 19, 1990
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Richard A. Hayes
  • Patent number: 4931540
    Abstract: 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: Grant
    Filed: November 24, 1987
    Date of Patent: June 5, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Werner H. Mueller, Dinesh N. Khanna, Rohitkumar H. Vora, Ruediger J. Erckel
  • Patent number: 4923968
    Abstract: 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: Grant
    Filed: July 11, 1988
    Date of Patent: May 8, 1990
    Assignee: Chisso Corporation
    Inventors: Kouichi Kunimune, Kazutsune Kikuta, Takao Kawamoto, Shiro Konotsune
  • Patent number: 4923960
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: May 8, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Paul N. Chen, Sr., Rohitkumar H. Vora
  • Patent number: 4914181
    Abstract: 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: Grant
    Filed: July 6, 1987
    Date of Patent: April 3, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Pfeifer, Rudolf Duthaler
  • Patent number: 4914175
    Abstract: 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: Grant
    Filed: May 10, 1988
    Date of Patent: April 3, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Eui W. Choe
  • Patent number: 4910293
    Abstract: 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: Grant
    Filed: October 11, 1988
    Date of Patent: March 20, 1990
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 4906730
    Abstract: 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: Grant
    Filed: May 6, 1988
    Date of Patent: March 6, 1990
    Assignee: General Electric Company
    Inventors: Tohru Takekoshi, Patricia P. Anderson
  • Patent number: 4902740
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: February 20, 1990
    Assignee: Teijin Limited
    Inventors: Shigeyoshi Hara, Hiroo Inata, Shunichi Matsumura
  • Patent number: 4897461
    Abstract: 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: Grant
    Filed: June 29, 1988
    Date of Patent: January 30, 1990
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 4895972
    Abstract: 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: Grant
    Filed: September 1, 1988
    Date of Patent: January 23, 1990
    Assignee: The United States of American as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Diane M. Stoakley, Anne K. St. Clair
  • Patent number: 4886873
    Abstract: 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: Grant
    Filed: March 7, 1988
    Date of Patent: December 12, 1989
    Assignee: Director-General of Agency of Industrial Science and Technology
    Inventors: Seiichi Mukai, Masatoshi Kimura, Shohachi Morita
  • Patent number: 4883858
    Abstract: 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: Grant
    Filed: August 19, 1988
    Date of Patent: November 28, 1989
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Masayuki Takemoto, Osamu Nagura, Yukio Nomura, Minoru Yasuda
  • Patent number: 4877653
    Abstract: 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: Grant
    Filed: July 12, 1988
    Date of Patent: October 31, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Rohitkumar H. Vora, Dinesh N. Khanna, Suzanne Fontaine
  • Patent number: 4864015
    Abstract: 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: Grant
    Filed: November 21, 1988
    Date of Patent: September 5, 1989
    Assignee: General Electric Company
    Inventors: James A. Cella, Deborah A. Haitko
  • Patent number: 4857079
    Abstract: 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: Grant
    Filed: April 7, 1988
    Date of Patent: August 15, 1989
    Assignee: TOA Nenryo Kogyo K.K.
    Inventor: Yoshiharu Kimura
  • Patent number: 4851506
    Abstract: 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: Grant
    Filed: December 21, 1987
    Date of Patent: July 25, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Ottmar Rohde, Andre-Etienne Perret, Josef Pfeifer
  • Patent number: 4851505
    Abstract: 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: Grant
    Filed: April 13, 1988
    Date of Patent: July 25, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard A. Hayes
  • Patent number: 4847358
    Abstract: 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: Grant
    Filed: August 18, 1987
    Date of Patent: July 11, 1989
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Mitsumasa Kojima, Takayuki Saito, Toul Kikuchi, Shun-ichiro Uchimura, Hidetaka Satou, Daisuke Makino
  • Patent number: 4847359
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: July 11, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Pfeifer, Rudolf Duthaler
  • Patent number: 4845167
    Abstract: 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: Grant
    Filed: October 29, 1986
    Date of Patent: July 4, 1989
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: William B. Alston, Roy F. Gratz
  • Patent number: 4837299
    Abstract: 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: Grant
    Filed: December 31, 1986
    Date of Patent: June 6, 1989
    Assignee: General Electric Company
    Inventors: Edward N. Peters, Michael W. Schultz
  • Patent number: 4837300
    Abstract: 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: Grant
    Filed: July 9, 1987
    Date of Patent: June 6, 1989
    Assignee: The United States of America as represented by the Administration of the National Aeronautics and Space Administration
    Inventors: Terry L. St. Clair, Harold D. Burks, Donald J. Progar
  • Patent number: 4837298
    Abstract: 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: Grant
    Filed: June 22, 1987
    Date of Patent: June 6, 1989
    Assignee: General Electric Company
    Inventors: James A. Cella, Thomas L. Guggenheim
  • Patent number: 4835249
    Abstract: 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: Grant
    Filed: December 31, 1986
    Date of Patent: May 30, 1989
    Assignee: General Electric Company
    Inventors: Patrick E. Gallagher, Ronald A. Greenberg
  • Patent number: 4824932
    Abstract: 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: Grant
    Filed: December 30, 1986
    Date of Patent: April 25, 1989
    Assignee: Huls Aktiengesellschaft
    Inventors: Juergen Finke, Martin Bartmann
  • Patent number: RE33079
    Abstract: 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: Grant
    Filed: March 5, 1979
    Date of Patent: October 3, 1989
    Assignee: Hughes Aircraft Company
    Inventors: Norman Bilow, Abraham L. Landis, Leroy J. Miller
  • Patent number: RE33342
    Abstract: 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: Grant
    Filed: September 1, 1988
    Date of Patent: September 18, 1990
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Noriaki Kohtoh, Toyohiko Abe, Hiroyoshi Fukuro