Reactant Contains Three Or More Carboxylic Acid Groups Or Is Derivative Thereof Patents (Class 528/188)
  • 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: 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: 4980447
    Abstract: The present invention provides polyamide-polyimide and polybenzoxazole-polyimide polymers derived therefrom with improved processing and film characteristics having incorporated into the polymeric backbone the polymeric condensation residuum of novel aromatic diamino compounds having the formula: ##STR1## wherein A is selected from the group consisting of SO.sub.2, O, S, CO, C.sub.1 to C.sub.6 alkyl, perfluoroalkyl or perfluoroarylalkyl having from 1 to 10 carbon atoms and a carbon-carbon double bond directly linking the two aromatic groups, and R is selected from the group consisting of hydrogen, hydroxy and C.sub.1 to C.sub.4 alkoxy.The polyamide-polyimide polymers of this invention are prepared by reacting compounds of the above formula, alone or admixed with other aromatic diamines, with one or more aromatic tetarcarboxylic acids or anhydrides thereof. Polybenzoxazole-polyimide derivatives of such polyamide-polyimide polymers are prepared utilizing compounds of the above formula wherein R is hydroxy or C.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: December 25, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Dinesh N. Khanna
  • Patent number: 4978573
    Abstract: Disclosed herein are free-standing, pinhole-free, ultrathin polyimide films having thickness of about 400 angstroms or less and a process to prepare them. The films find particular utility in separatory applications.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: December 18, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Rachel S. Kohn
  • Patent number: 4978737
    Abstract: Polyimides derived from the reaction product of 3,3'-6 F diamine or 4,4'-6 F diamine and pyromellitic dianhydride (PMDA) can be rendered solvent soluble while at the same time exhibiting an improvement in both mechanical and electrical properties by the inclusion of at least one other dianhydride having a diaryl nucleus in the reaction media. Suitable such dianhydrides include bis (3,4 dicarboxy phenyl) ether dianhydride (ODPA), 3,3'4,4' benzophenone tetracarboxylic dianhydride (BTDA), 3,3',4,4' diphenyl tetracarboxylic acid dianhydride (BPDA) and 2,2 bis(3,4 dicarboxyphenyl) hexafluoropropane dianhydride (6F-DA). Such polyimides are soluble in common organic solvents such as methyl ethyl ketone or N methyl pyrrolidone, and exhibit excellent film forming properties with improved mechanical and electrical properties as compared to the corresponding homopolyimides. They possess excellent heat stability (Tg's in excess of about 350.degree. C.
    Type: Grant
    Filed: July 12, 1988
    Date of Patent: December 18, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Rohitkumar H. Vora
  • Patent number: 4978738
    Abstract: High molecular weight polyimides are formed by polycondensation of 2,2-bis(4-aminophenyl) hexafluoropropane or 2,2-bis(3-aminophenyl) hexafluoropropane with one or more of bis-(3,4 dicarboxyphenyl) ether dianhydride; 3,3', 4,4' benzophenone tetracarboxylic acid dianhydride; 3,3', 4,4' diphenyl tetracarboxylic acid dianhydride and 2,2-bis(3,4 dicarboxyphenyl) hexafluoropropane dianhydride. Generally, the polymers of the present invention are characterized by a molecular weight of more than about 90,000.
    Type: Grant
    Filed: July 12, 1988
    Date of Patent: December 18, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Werner H. Mueller, Rohitkumar H. Vora, Dinesh N. Khanna
  • Patent number: 4978733
    Abstract: The present invention provides polyamide-polyamide-polyimide and polybenzoxazole-polyamide-polyimide polymers derived therefrom with improved processing and film characteristics having incorporated into the polymeric backbone the polymeric condensation residuum of novel aromatic diamino compounds having the formula: ##STR1## wherein A is selected from the group consisting of SO.sub.2, O, S, CO, C.sub.1 to C.sub.6 alkylene, perfluoroalkylene or perfluoroarylalkylene having from 1 to 10 carbon atoms and a bond directly linking the two aromatic groups, and R is selected from the group consisting of hydrogen, hydroxy and C.sub.1 to C.sub.4 alkoxy.The PA-PA-PI polymers of this invention are prepared by reacting compounds of the above formula alone or admixed with other aromatic diamines, with carboxyphenyl trimellitimide or the acid halide or ester derivatives thereof, alone or admixed with one or more aromatic diacid chlorides and/or one or more aromatic tetracarboxylic acids or anhydrides thereof.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: December 18, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Dinesh N. Khanna
  • Patent number: 4978734
    Abstract: The present invention provides polyamide-polyamide and polybenzoxazole-polyamide polymers derived therefrom with improved processing and film characteristics having incorporated into the polymeric backbone the polymeric condensation residuum of novel aromatic diamino compounds having the formula: ##STR1## wherein A is selected from the group consisting of SO.sub.2, O, S, CO, C.sub.1 to C.sub.6 alkylene, perfluoroalkylene or perfluoroalkylene having from 1 to 10 carbon atoms and a bond directly linking the two aromatic groups and R is selected from the group consisting of hydrogen, hydroxy and C.sub.1 to C.sub.4 alkoxy.The polyamide-polyamide polymers of this invention are prepared by reacting compounds of the above formula, alone or admixed with othr aromatic diamines, with one or more aromatic or aliphatic dicarboxylic acid or amide-forming derivatives thereof.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: December 18, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Dinesh N. Khanna
  • Patent number: 4978742
    Abstract: Polyimides and polyamide-acids having improved solubility and processing characterisitcs are provided having incorporated into the polymeric chain as a novel aromatic diamine compound, 2-(3-aminophenyl)-2-(4-aminophenyl) hexafluoropropane (3,4'-6F Diamine). The polyamide-acids and polyimides are prepared by reacting the 3,4'-6F Diamine with aromatic tetracarboxylic acids or anhydrides thereof. It has been found that the polyimides of this invention have improved solubility characterisitics, low dielectric constants and improved thermal flow properties as a consequence of the meta/para positioning of the amino groups on the diamine, which renders these polymers more readily melt spinnable for the production of fibers. The polymers may also be compression molded and fabricated into composites at moderate temperatures and pressures. Solutions of the polyimides may be cast into films.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: December 18, 1990
    Assignee: Hoechst Celanese Corp.
    Inventors: Rohitkumar H. Vora, Werner H. Mueller
  • Patent number: 4975521
    Abstract: Soluble, film-forming, polyamides, polyimides, and polyamide-imides and their copolymers made using 3,5-diamino-t-butylbenzene are described. These polymers have some solubility in organic solvents such as N-methylpyrrolidone, a high Tg, excellent thermal stability, lower density and lower moisture uptake and are useful in films, fibers and composites, and in the electronics industry as electrical component substrates, protective coatings, interlevel dielectrics and the like.
    Type: Grant
    Filed: April 16, 1990
    Date of Patent: December 4, 1990
    Assignee: Amoco Corporation
    Inventors: Douglas E. Fjare, Neal R. Nowicki
  • Patent number: 4973651
    Abstract: The present invention provides novel heat stable polyimide and polyamic acid precursor 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 aromatic dianhydride monomers, at least one of said diamine monomers having the structure: ##STR1## wherein R is CF.sub.3 or phenyl. The polyimides of this invention exhibit improved solubility and low temperature flow characteristics, low moisture uptake, high thermal stability, low dielectric constant and good hydrolytic stability.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: November 27, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Rohitkumar H. Vora
  • Patent number: 4968757
    Abstract: There is provided a siloxane-imide copolymer composition having at least one polymeric block with a low glass transition temperature and at least one polymeric block with a high glass transition temperature.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: November 6, 1990
    Assignee: MicroSi, Inc.
    Inventor: Chung J. Lee
  • 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: 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: 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: 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: 4962181
    Abstract: The present invention provides novel heat stable polyamide polymer 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 aromatic dibasic acid monomers or amide-forming derivatives thereof, at least one of said diamine monomers having the structure: ##STR1## where R is CF.sub.3 or phenyl. The polyamides of this invention exhibit improved solubility and low temperature flow characteristics, low moisture uptake, high thermal stability, low dielectric constant and good hydrolytic stability.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: October 9, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Rohitkumar H. Vora
  • Patent number: 4960824
    Abstract: Storage stable polyimide precursors are prepared from diesters of certain tetracarboxylic acids, including pyromellitic acid and 2,2-bis[4-(3,4-dicarboxyphenoxy)-phenyl]propane, and m-phenylenediamine, p-phenylenediamine, 4-aminophenyl ether or mixtures thereof. These polyimide precursors may be cured to form flexible polyimides useful in composite preparation.
    Type: Grant
    Filed: September 26, 1988
    Date of Patent: October 2, 1990
    Assignee: General Electric Company
    Inventors: Daniel R. Olson, Elbridge A. O'Neil, Jr.
  • Patent number: 4959437
    Abstract: A process for producing a silicon-containing polyamic acid affording a silicon-containing polyimide having a low thermal expansion coefficient and a process for producing the silicon-containing polyimide are provided, the former process comprising reacting pyromellitic acid dianhydride (A.sup.1 mols) and 3,3',4,4'-biphenyltetracarboxylic acid dianhydride (A.sup.2 mols) with a diamine of the following formula (I) (B mols) and an aminosilicon compound of the formula (II) so as to satisfy the following expressions (III) and (IV): ##STR1## wherein R.sup.1 is methyl, ethyl, methoxy, ethoxy or halogen; R.sup.2 is alkyl or alkyl-substituted phenyl; X is a hydrolyzable alkoxy, acetoxy or halogen; m is 0, 1 or 2; n is 1 or 2; and k is 1, 2 or 3; andthe latter process comprising baking a solution of the above silicon-containing polyamic acid at 50.degree. to 500.degree. C.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: September 25, 1990
    Assignee: Chisso Corporation
    Inventors: Kouichi Kunimune, Yoshiya Kutsuzawa, Shiro Konotsune
  • Patent number: 4959447
    Abstract: A copoly(imidine-imide) consisting of a copolymer of polyimidines and polyimides having, in the basic chain structure of the polymer, imidine structures represented by formula (I) and the imide structures represented by formula (II): ##STR1##
    Type: Grant
    Filed: September 2, 1988
    Date of Patent: September 25, 1990
    Assignee: Nippon Steel Corporation
    Inventors: Mitsuru Arai, Patrick E. Cassidy, James M. Farley
  • Patent number: 4956451
    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 water. The result is the formation of unacceptable coatings due to their irregularity and lack of uniformity. Described are compositions especially adapted for use in spin coating wafers of semiconductive materials, which comprise solutions of these polyimide polymers in a solvent containing at least 10% of a cycloaliphatic ketone (e.g., cyclohexanone) or mixture of cycloaliphatic ketones, 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 up to at least about 55% relative humidity.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: September 11, 1990
    Assignee: Ethyl Corporation
    Inventors: Allan A. Eisenbraun, Wesley C. Blocker
  • 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: 4954606
    Abstract: Thermotropic polyester imides having recurrent units corresponding to the following formulae: ##STR1## have excellent dimensional stability under heat and are suitable for the production of moulded articles, filaments, fibres and films.
    Type: Grant
    Filed: October 19, 1988
    Date of Patent: September 4, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Rudolf Dicke, Joachim Genz, Volker Eckhardt, Ludwig Bottenbruch
  • 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: 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: 4952669
    Abstract: Coolyimides and copolyamide-acids having improved solubility and processing characteristics are provided having incorporated into the polymeric chain as a novel aromatic diamine compound, 2-(3-aminophenyl)-2-(4-aminophenyl) hexafluoropropane (3,4'-6F Diamine). The copolyamide-acids and copolyimides are prepared by reacting the 3,4'-6F Diamine with a mixture of two or more aromatic tetracarboxylic acids or anhydrides thereof. It has been found that the copolyimides of this invention have improved solubility characteristics, low dielectric constants and improved thermal flow properties as a consequence of the meta/para positioning of the amino groups on the diamine, which renders these copolymers more readily melt sqinnable for the production of fibers. The copolymers may also be compression molded and fabricated into composites at moderate temperatures and pressures. Solutions of the copolyimides may be cast into films.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: August 28, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Rohitkumar H. Vora
  • Patent number: 4952611
    Abstract: Described are flexible polyimide foams having enhanced compression characteristics and softness for use in the manufacture of seat cushions and methods for the production of such foams and precursors therefor. These foams are produced from novel polyimides prepared by reaction of at least one aromatic or heterocyclic primary diamine with a mixture of at least two organic tetracarboxylic acids or derivatives thereof, at least one of which is from 1 to 40 mol percent of a 2-(vicinal-dicarboxycyclohexenyl)succinic acid or derivative thereof and a second of which is an aromatic tetracarboxylic acid or derivative thereof.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: August 28, 1990
    Assignee: Ethyl Corporation
    Inventor: David M. Indyke
  • Patent number: 4950734
    Abstract: In humid 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 at least 40% by weight of one or more liquid aromatic hydrocarbons having a boiling point of at least about 110.degree. C. and at least 5% by weight of one or more dipolar aprotic solvents having a boiling point of at least about 150.degree. C.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: August 21, 1990
    Assignee: Ethyl Corporation
    Inventors: Allan A. Eisenbraun, Wesley C. Blocker
  • Patent number: 4948863
    Abstract: Thermotropic polyester imides having recurrent structural units corresponding to the following formulae: ##STR1##
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: August 14, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Rudolf Dicke, Joachim Genz, Volker Eckhardt, Ludwig Bottenbruch
  • Patent number: 4943471
    Abstract: A patterned thin film suitable for use in electric and electronic devices, prepared from a polymer or a mixture of the polymer and other known compounds capable of forming a thin film by LB technique, said polymer having linear recurring units wherein an organic group R.sup.1 having at least 2 carbon atoms and a valence of at least 2 is combined alternately with an organic group R.sup.2 having at least 2 carbon atoms and a valence of at least 2 through a bivalent group formed by a reaction of an acid group A containing a hetero atom and a basic group B containing a hetero atom, and wherein a hydrocarbon-containing group R.sup.3 having 10 to 30 carbon atoms which may contain a substituent group, is linked by covalent or ionic bond to said recurring units, the number of groups R.sup.3 being at least 2 per 10 recurring units.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: July 24, 1990
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji, Makoto Murata, Satoshi Mizunuma
  • 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: 4933132
    Abstract: The present invention provides a process for preparing shaped articles and articles prepared by such process based on a polyimide polymer, the polymer prepared by subjecting a mixture of aromatic dianhydride and aromatic diamine monomers, at least one of which contains the group ##STR1## linking two aromatic moieties, wherein R is CF.sub.3 or phenyl, to a low temperature, substantially isothermal solution polymeriazation process wherein the content of the mixed monomers in solvent is maintained within the range of from about 8 to about 12% by weight solids concentration during the polymerization process. The process is conducted for a sufficient length of time and uniformity of temperature, generally below about 35.degree. C., to achieve a weight average polyimide polymer molecular weight within the range of about 80,000 to about 135,000, more preferably of about 90,000 to about 125,000, a polyimide inherent viscosity within the range of from about 0.45 to about 0.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: June 12, 1990
    Assignee: Hoechst Celanese Corp.
    Inventor: Rohitkumar H. Vora
  • Patent number: 4931531
    Abstract: This invention relates to a novel polyimide which is high-temperature resistant and capable of being molded in a fused state. This invention also relates to a high-temperature adhesive using the polyimide.The polyimide consists essentially of recurring units of the formula: ##STR1## where R is a tetra-valent radical selected from the group consisting of an aliphatic radical having 2 or more carbon atoms, alicyclic radical, monoaromatic radical, condensed polyaromatic radical, and non-condensed polyaromatic radical wherein aromatic radicals are linked to one another directly or via a bridge member.The polyimide can be prepared by reacting bis[4-(4-aminophenoxy)phenoxy)phenyl] sulfone with a tetracarboxylic dianhydride in an organic solvent and imidizing the resultant polyamic acid.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: June 5, 1990
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shoji Tamai, Masahiro Ohta, Saburo Kawashima, Katsuaki Iiyama, Hideaki Oikawa, Akihiro Yamaguchi
  • Patent number: 4931539
    Abstract: Highly-soluble, fully-cyclized siloxane polyimides, which contain at least in part, polymerized units derived from 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl) ethylidene]-bis(1,2-benzenedicarboxylic acid anhydride), (6FDA), are disclosed. The polymeric compositions, their preparation and film/coating products are described.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: June 5, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard A. Hayes
  • Patent number: 4927736
    Abstract: This invention relates to novel hydroxy polyimides and radiation sensitive compositions prepared therefrom. More particularly the invention relates to positive photoresists useful in the preparation of a thermally stable relief pattern on a substrate e.g. a silicon wafer or aluminum plate. The novel hydroxy polyimides of the invention may also be used to provide thermally stable organic protective films and layers e.g. an insulating and/or a passivating layer in a semi-conductor component.The novel hydroxy polyimides of in this invention can be synthesized by the condensation of a hydroxy-substituted aminophenol and a dianhydride. Radiation sensitive compositions prepared from the novel hydroxy polyimides of the invention can be developed in aqueous base developer or organic solvent developer; preferably aqueous base developer. Also, the base developer dissolution properties of the polyimides can be controlled by incorporating a non-hydroxyl diamine into the polyimide.
    Type: Grant
    Filed: July 21, 1987
    Date of Patent: May 22, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Werner H. Mueller, Dinesh N. Khanna
  • 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: 4914182
    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: 4912197
    Abstract: Highly soluble, optically transparent to clear aromatic polyimides in the visible range are disclosed. The dianhydrides from which the polyimides are prepared are 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl) ethylidene] bis(1,2-benzenedicarboxylic anhydride) which can be partially replaced with either pyromellitic dianhydride or 3,3',4,4'-benzophenone tetracarboxylic dianhydride. The diamines from which the polyimides are prepared are m- or p- phenylene diamines which are substituted ortho to the amino groups with primary or secondary alkyl groups having 1 to 6 carbon atoms preferably methyl or ethyl.
    Type: Grant
    Filed: April 19, 1988
    Date of Patent: March 27, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard A. Hayes
  • Patent number: 4908409
    Abstract: Polyimide of this invention is almost colorless and has remarkably high light transmittance as well as excellent processability and adhesive properties at high temperatures in addition to its substantial high-temperature stability.The polyimide is a novel polyimide capable of being used for space and aeronautical materials, electric and electronic members, automotive parts, and furthermore for high-temperature adhesives.The polyimide has recurring units of the following formula ##STR1## wherein X is a radical selected from the group consisting of a bond, divalent hydrocarbon radical having from 1 to 10 carbons, hexafluorinated isopropylidene radical, carbonyl radical, sulfonyl radical and thio radical, and each nitrogen atom of imide ring is located simultaneously at meta- or para-position to ether linkage.
    Type: Grant
    Filed: November 10, 1987
    Date of Patent: March 13, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hideaki Oikawa, Katsuaki Liyama, Nobuhito Koga, Saburo Kawashima, Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
  • Patent number: 4906731
    Abstract: Extraction of polyamic acid-polyimide gel in bipolymerized polyimide manufacturing process with a solvent containing an extraction-enhancing agent, which is a pyridine, picoline, or quinoline, leads to a polyimide film having increased molecular weight. Polyimides are valuable materials used in fabricating articles which must withstand high temperatures, especially in aerospace applications, and in the manufacture of electronic circuit boards.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: March 6, 1990
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Richard F. Sutton, Jr.
  • Patent number: 4904758
    Abstract: The present invention is connected with a low-melting polyimide copolymer containing 30 to 90 mole % of an imide repeating unit represented by the following formula (I) and 10 to 70 mole % of an imide repeating unit represented by the following formula (II), and having a logarithmic viscosity number of 0.1 to 4 dl/g: ##STR1## wherein R.sup.1 is at least one of ##STR2## Furthermore, the present invention is connected with a method of preparing the low-melting polyimide copolymer.Since having a melting point of about 300.degree. to about 400.degree. C., the polyimide copolymer of the present invention has heat resistance and enables melt-moldings such as extrusion and injection molding.
    Type: Grant
    Filed: January 5, 1989
    Date of Patent: February 27, 1990
    Assignee: Chisso Corporation
    Inventors: Kouichi Kunimune, Hirotoshi Maeda
  • 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