Plural Bicyclo Ring Systems Each Having The Cyclic Anhydride As One Of The Cyclos Patents (Class 549/241)
  • Patent number: 10065969
    Abstract: A method for producing a carboxylic acid anhydride includes heating a composition containing a specific compound in a solvent to yield the carboxylic acid anhydride. The solvent is an aprotic polar solvent having a boiling point of 50° C. or more.
    Type: Grant
    Filed: June 22, 2016
    Date of Patent: September 4, 2018
    Assignee: CANON KABUSHIKI KAISHA
    Inventors: Kei Tagami, Akihito Saitoh, Kunihiko Sekido, Michiyo Sekiya, Masashi Nishi
  • Patent number: 9228118
    Abstract: An object of the present invention is to provide a method for producing polyamide acid particles which is used as a raw material for polyimide particles with a small average particle diameter having high heat resistance. Other objects of the present invention are to provide a method for producing polyimide particles using the method for producing polyamide acid particles, and polyimide particles produced by the method for producing polyimide particles. Yet another object of the present invention is to provide a bonding material for an electronic component, which has a low linear expansion coefficient and a low elastic modulus after being cured in the temperature range equal to or less than the glass transition temperature, so that a joined body with high reliability can be produced.
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: January 5, 2016
    Assignee: SEKISUI CHEMICAL CO., LTD.
    Inventor: Satoshi Hayashi
  • Patent number: 9074051
    Abstract: A dianhydride monomer having a large side chain R is provided. The large side chain would interrupt the symmetry and regularity of diamine monomer. The diamine monomer has the general formula shown as formula (I) below: The functional group R includes ?-substitution cycloalkene having at least a tertiary carbon atom, cycloalkene having at least a tertiary carbon atom, cycloalkane having at least a tertiary carbon atom, ?-substitution phenyl, phenyl, ?-substitution naphthalyl, naphthalyl, ?-substitution phenanthrenyl, phenanthrenyl, ?-substitution anthracenyl, anthracenyl, ?-substitution adamantyl, adamantyl, ?-substitution adamantyl and adamantyl.
    Type: Grant
    Filed: March 18, 2013
    Date of Patent: July 7, 2015
    Assignee: Unimicron Technology Corp.
    Inventor: Han-Pei Huang
  • Patent number: 9018401
    Abstract: A process for obtaining (ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione) is disclosed. In the disclosed process chloro-, bromo-, or iodoisobenzofuran-1,3-dione is reacted with ethyne in a solvent in the presence of a dissolved homogenous palladium catalyst, optionally a copper salt, a base, and optionally a solvent distinct from said base. Subsequently the obtained (ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione) may be washed with a washing agent, such as a carboxylic acid, a polar aprotic solvent, or chloroform.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: April 28, 2015
    Assignee: Nexam Chemical AB
    Inventors: Jan-Erik Rosenberg, Daniel Rome, Erik Lager, Dane Momcilovic
  • Publication number: 20150080586
    Abstract: A process for obtaining (ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione) is disclosed. In the disclosed process chloro-, bromo-, or iodoisobenzofuran-1,3-dione is reacted with ethyne in a solvent in the presence of a dissolved homogenous palladium catalyst, optionally a copper salt, a base, and optionally a solvent distinct from said base. Subsequently the obtained (ethyne-1,2-diyl)bis(isobenzofuran-1,3-dione) may be washed with a washing agent, such as a carboxylic acid, a polar aprotic solvent, or chloroform.
    Type: Application
    Filed: March 8, 2013
    Publication date: March 19, 2015
    Inventors: Jan-Erik Rosenberg, Daniel Röme, Erik Lager, Dane Momcilovic
  • Publication number: 20140275470
    Abstract: A dianhydride monomer having a large side chain R is provided. The large side chain would interrupt the symmetry and regularity of diamine monomer. The diamine monomer has the general formula shown as formula (I) below: The functional group R includes ?-substitution cycloalkene having at least a tertiary carbon atom, cycloalkene having at least a tertiary carbon atom, cycloalkane having at least a tertiary carbon atom, ?-substitution phenyl, phenyl, ?-substitution naphthalyl, naphthalyl, ?-substitution phenanthrenyl, phenanthrenyl, ?-substitution anthracenyl, anthracenyl, ?-substitution adamantyl, adamantyl, ?-substitution adamantyl and adamantyl.
    Type: Application
    Filed: March 18, 2013
    Publication date: September 18, 2014
    Applicant: UNIMICRON TECHNOLOGY CORP.
    Inventor: HAN-PEI HUANG
  • Patent number: 8492565
    Abstract: To provide a process for producing BPDA whereby high productivity is attained while high purity is maintained. A process for producing biphenyltetracarboxylic acid dianhydride, which comprises heating biphenyltetracarboxylic acid to produce biphenyltetracarboxylic acid dianhydride, characterized in that the heating is carried out at a pressure of from 1×102 Pa to 1.1×105 Pa to a maximum temperature in a range of from 210° C. to 250° C. in such a manner that the temperature rising rate is higher than 50° C./hr for a period of at least ¼ of the time for the temperature rise from 60° C. to 210° C., and the temperature is maintained to be from 150° C. to 250° C. for from 0.5 to 10 hours.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: July 23, 2013
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hiroshi Mikami, Makoto Nitta, Naoki Noguchi
  • Publication number: 20130012682
    Abstract: To provide a process for producing BPDA whereby high productivity is attained while high purity is maintained. A process for producing biphenyltetracarboxylic acid dianhydride, which comprises heating biphenyltetracarboxylic acid to produce biphenyltetracarboxylic acid dianhydride, characterized in that the heating is carried out at a pressure of from 1×102 Pa to 1.1×105 Pa to a maximum temperature in a range of from 210° C. to 250° C. in such a manner that the temperature rising rate is higher than 50° C./hr for a period of at least ¼ of the time for the temperature rise from 60° C. to 210° C., and the temperature is maintained to be from 150° C. to 250° C. for from 0.5 to 10 hours.
    Type: Application
    Filed: September 14, 2012
    Publication date: January 10, 2013
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Hiroshi Mikami, Makoto Nitta, Naoki Noguchi
  • Patent number: 8299273
    Abstract: To provide a process for producing BPDA whereby high productivity is attained while high purity is maintained. A process for producing biphenyltetracarboxylic acid dianhydride, which comprises heating biphenyltetracarboxylic acid to produce biphenyltetracarboxylic acid dianhydride, characterized in that the heating is carried out at a pressure of from 1×102 Pa to 1.1×105 Pa to a maximum temperature in a range of from 210° C. to 250° C. in such a manner that the temperature rising rate is higher than 50° C./hr for a period of at least ¼ of the time for the temperature rise from 60° C. to 210° C., and the temperature is maintained to be from 150° C. to 250° C. for from 0.5 to 10 hours.
    Type: Grant
    Filed: August 12, 2010
    Date of Patent: October 30, 2012
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hiroshi Mikami, Makoto Nitta, Naoki Noguchi
  • Patent number: 8168796
    Abstract: There are provided novel fluorescent agents, such as pyrazoline compounds represented by formula (I): (wherein R1, R2 and R3 are as defined in the specification), having an ethynyl group in the molecule, which have high absorptivity in the ultraviolet-visible short wavelength range (for example, 350 nm-420 nm).
    Type: Grant
    Filed: January 19, 2009
    Date of Patent: May 1, 2012
    Assignee: Nippon Chemical Works Co., Ltd.
    Inventors: Kazuhiko Mizuno, Hideyuki Takagaki, Hirokazu Iwahashi, Kaname Inoue
  • Publication number: 20110319620
    Abstract: When phthalic acid is heated in heptane under azeotropic reflux conditions in the presence of a catalytic amount of an arylboronic acid compound (such as 2,6-(diisopropylaminomethyl)phenylboronic acid or 2,6-bis(diisopropylaminomethyl)phenylboronic acid), phthalic anhydride is obtained in high yield.
    Type: Application
    Filed: March 3, 2010
    Publication date: December 29, 2011
    Applicant: NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY
    Inventors: Kazuaki Ishihara, Akira Sakakura
  • Patent number: 8013173
    Abstract: A method for purifying an oxydiphthalic anhydride comprises diluting a first mixture comprising an oxydiphthalic anhydride, a solvent, a catalyst, and an inorganic salt with a solvent, to provide a second mixture having a solids content of 10 to 30 percent based on total weight of the second mixture; filtering and washing the solids of the second mixture at a temperature below the crystallization point temperature of the oxydiphthalic anhydride to provide a third mixture; hydrolyzing the third mixture by adding water and a water-soluble acid to form a fourth mixture; heating the fourth mixture; then cooling to provide a solid-liquid mixture, optionally decanting a portion of the liquid, rediluting the remaining solid-liquid mixture, then filtering to provide a solid component; washing the solid component with water to provide a fifth mixture of oxydiphthalic tetraacid and water; ring closing the oxydiphthalic tetraacid to provide oxydiphthalic anhydride, and filtering the oxydiphthalic anhydride.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: September 6, 2011
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Beatriz Penalver Bernabe, Vijay Gopalakrishnan, Lioba Maria Kloppenburg, Matt Kuhlman, Roy Ray Odle, Eric Pressman, Narayan Ramesh, Harpreet Singh
  • Patent number: 7863463
    Abstract: Disclosed herein is a method for purification of dianhydrides comprising a substantial amount (10000 ppm or more) of at least one metal salt. In one aspect the method is useful for the purification of dianhydrides prepared by the reaction of a halophthalic anhydride with a metal carbonate and may be optionally catalyzed by a phase transfer catalyst. The purification of the dianhydrides may be accomplished by hydrolyzing the dianhydride metal salt mixture directly to a tetraacid with an inorganic acid, followed by separating the impurities from an aqueous phase, and subsequently heating the tetraacid to effect ring closure to form a purified dianhydride having less than 50 parts per million metal halide and lower levels of other residual impurities. In one aspect the method is highly effective in removing phase transfer catalyst impurities such as hexalkylguanidinium halides initially present in the dianhydride undergoing purification.
    Type: Grant
    Filed: November 22, 2005
    Date of Patent: January 4, 2011
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Eric James Pressman, Albert Santo Stella, Beatriz Peñalver Bernabe, Lioba Maria Kloppenburg, Lee Harris Bergman
  • Publication number: 20100305299
    Abstract: To provide a process for producing BPDA whereby high productivity is attained while high purity is maintained. A process for producing biphenyltetracarboxylic acid dianhydride, which comprises heating biphenyltetracarboxylic acid to produce biphenyltetracarboxylic acid dianhydride, characterized in that the heating is carried out at a pressure of from 1×102 Pa to 1.1×105 Pa to a maximum temperature in a range of from 210° C. to 250° C. in such a manner that the temperature rising rate is higher than 50° C./hr for a period of at least ¼ of the time for the temperature rise from 60° C. to 210° C., and the temperature is maintained to be from 150° C. to 250° C. for from 0.5 to 10 hours.
    Type: Application
    Filed: August 12, 2010
    Publication date: December 2, 2010
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Hiroshi Mikami, Makoto Nitta, Naoki Noguchi
  • Patent number: 7842824
    Abstract: To provide a process for producing BPDA whereby high productivity is attained while high purity is maintained. A process for producing biphenyltetracarboxylic acid dianhydride, which comprises heating biphenyltetracarboxylic acid to produce biphenyltetracarboxylic acid dianhydride, characterized in that the heating is carried out at a pressure of from 1×102 Pa to 1.1×105 Pa to a maximum temperature in a range of from 210° C. to 250° C. in such a manner that the temperature rising rate is higher than 50° C./hr for a period of at least ¼ of the time for the temperature rise from 60° C. to 210° C., and the temperature is maintained to be from 150° C. to 250° C. for from 0.5 to 10 hours.
    Type: Grant
    Filed: June 28, 2005
    Date of Patent: November 30, 2010
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hiroshi Mikami, Makoto Nitta, Naoki Noguchi
  • Patent number: 7674920
    Abstract: A method for preparing an oxydiphthalic anhydride comprises contacting, under reactive and substantially anhydrous conditions in a reactor, at least one halophthalic anhydride containing more than 250 ppm chlorophthalide impurity with a carbonate of the formula M2CO3, wherein M is an alkali metal, in the presence of a catalytic proportion of at least one phase transfer catalyst selected from the group consisting of hexaalkylguanidinium halides and alpha,omega-bis(pentaalkylguanidinium)alkane salts, phosphonium salts, phosphazenium salts, pyridinium salts, phosphazenium salts, ammonium salts, and combinations thereof. The phase transfer catalyst is present in a sufficient amount to prepare the oxydiphthalic anhydride when the chlorophthalide is present in an amount that is more than 250 ppm, and the oxydiphthalic anhydride is produced in a yield, based on the carbonate, of at least 70%.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: March 9, 2010
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Beatriz Penalver Bernabe, Lioba Maria Kloppenburg, Matt Kuhlman, Roy Ray Odle, Eric Pressman, Narayan Ramesh, Harpreet Singh
  • Publication number: 20090247727
    Abstract: A method for purifying an oxydiphthalic anhydride comprises diluting a first mixture comprising an oxydiphthalic anhydride, a solvent, a catalyst, and an inorganic salt with a solvent, to provide a second mixture having a solids content of 10 to 30 percent based on total weight of the second mixture; filtering and washing the solids of the second mixture at a temperature below the crystallization point temperature of the oxydiphthalic anhydride to provide a third mixture; hydrolyzing the third mixture by adding water and a water-soluble acid to form a fourth mixture; heating the fourth mixture; then cooling to provide a solid-liquid mixture, optionally decanting a portion of the liquid, rediluting the remaining solid-liquid mixture, then filtering to provide a solid component; washing the solid component with water to provide a fifth mixture of oxydiphthalic tetraacid and water; ring closing the oxydiphthalic tetraacid to provide oxydiphthalic anhydride, and filtering the oxydiphthalic anhydride.
    Type: Application
    Filed: March 28, 2008
    Publication date: October 1, 2009
    Inventors: Beatriz Penalver Bernabe, Vijay Gopalakrishnan, Lioba Maria Kloppenburg, Matt Kuhlman, Roy Ray Odle, Eric Pressman, Narayan Ramesh, Harpreet Singh
  • Patent number: 7585984
    Abstract: The present invention relates to a deuterated polyimide, the backbone of which comprises an alternation between: at least one repeat unit corresponding to the following formula (I): in which: Y represents a single bond or a spacer group; and at least one repeat unit corresponding to the following formula (II): -A1-Z-??(II) in which: A1 represents a perdeuterated aromatic group comprising from 6 to 10 carbon atoms; Z represents a single bond or a group chosen from —O—C6D4—, —CO—C6D4— and —C6D4—. These polyimides are used in particular as materials which are transparent within the region from 2500 to 3500 cm?1, for example in laser devices.
    Type: Grant
    Filed: April 5, 2007
    Date of Patent: September 8, 2009
    Assignee: Commissariat a l'Energie Atomique
    Inventors: Elsa Anselmi, Jacques Raby, Alexia Balland-Longeau, Marc Calonne
  • Publication number: 20090156834
    Abstract: There is provided a continuous process for making 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane. The process has the following steps: a) continuously feeding 2,2-bis(3,4-dimethylphenyl)hexafluoropropane and aqueous nitric acid into a reactor cell and b) heating the mixture to a temperature sufficient to effect reaction between the 2,2-bis(3,4-dimethylphenyl)hexafluoropropane and the nitric acid.
    Type: Application
    Filed: December 3, 2008
    Publication date: June 18, 2009
    Inventors: Andreas Kanschik-Conradsen, Bjoern Oliver Jackisch, Ralph Lonsky
  • Publication number: 20090018349
    Abstract: 2,3,3?,4?-biphenyltetracarboxylic acid is heat-dehydrated in a molten state at a temperature not lower than 200° C. in a flow of an inert gas in a reactor 10 having at least one reaction vessel 11 by stirring the molten material to produce 2,3,3?,4?-biphenyltetracarboxylic dianhydride. Thus obtained 2,3,3?,4?-biphenyltetracarboxylic dianhydride in the molten state is subsequently cooled and solidified in an inert gas or dry air, or cooled and solidified in the ambient air at a temperature of 40° C. or lower or 100° C. or higher.
    Type: Application
    Filed: July 10, 2008
    Publication date: January 15, 2009
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Kenichiro Sasaki, Tatsushi Nakayama
  • Patent number: 7446214
    Abstract: A method for purifying dianhydrides is provided. In one aspect, purified oxybisphthalic anhydrides, intermediates useful in the preparation of polyetherimides are provided. In one embodiment, a first solution containing a dianhydride compound, a solvent, and a phase transfer catalyst is contacted with a solid inorganic adsorbent material having a total pore volume of about 0.5 milliliters/gram or greater and a cumulative pore volume distribution of about 20 percent or greater of particles having a pore diameter in a range between about 3 nanometers and about 20 nanometers. The solution containing the dianhydride compound is then separated from the solid inorganic adsorbent material to provide a purified dianhydride compound which is substantially free of the phase transfer catalyst. The purification technique is especially valuable for preparing high purity oxybisphthalic anhydrides, such as 4,4?-oxybisphthalic anhydride (4,4?-ODPA), which are substantially free of residual phase transfer catalyst.
    Type: Grant
    Filed: November 22, 2006
    Date of Patent: November 4, 2008
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Albert Santo Stella, David Bruce Hall
  • Publication number: 20080214841
    Abstract: There is provided biphenyltetracarboxylic dianhydride containing biphenyltetracarboxylic monoanhydride in an amount of not more than 0.4%. By using the biphenyltetracarboxylic dianhydride as a raw material, it is possible to produce polyimide or polyamic acid having an increased molecular weight.
    Type: Application
    Filed: April 10, 2008
    Publication date: September 4, 2008
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Hiroshi Mikami, Takeshi Sano, Makoto Nitta
  • Patent number: 7268237
    Abstract: This invention is related to a method for making diether dianhydrides by the reaction of halophthalic anhydride and a metal salt of an aromatic dihydroxy compound in the presence of a solvent and a phase transfer catalyst. Typical phase transfer catalyst include guanidium salts, aminopyridinium salts, or phosphazenium salts.
    Type: Grant
    Filed: March 11, 2005
    Date of Patent: September 11, 2007
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, James Anthony Cella, Qing Ye, Kwok Pong Chan
  • Patent number: 7217827
    Abstract: The present invention relates to halogen-containing aromatic compounds and methods thereof. The present invention relates a halogen-containing aromatic acid dianhydride, halogen-containing aromatic tetranitrile compound, halogen-containing m-phenylenediamine compound and fluorine compound, and a method thereof.
    Type: Grant
    Filed: November 23, 2004
    Date of Patent: May 15, 2007
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Masayoshi Kuwabara, Yasunori Okumura
  • Patent number: 6881815
    Abstract: A method for the synthesis of poly(etherimide)s comprises the reaction of 4-halotetrahydrophthalic anhydride with an activating primary amine to yield an activated 4-halotetrahydrophthalimide. Activated 4-halotetrahydrophthalimide may then be aromatized and treated with the disodium salt of a bis(phenol) to yield an activated bisimide. The activated bisimide may then be directly treated with a diamine to yield poly(etherimide)s.
    Type: Grant
    Filed: September 25, 2002
    Date of Patent: April 19, 2005
    Assignee: General Electric Company
    Inventors: Roy Ray Odle, Thomas Link Guggenheim
  • Publication number: 20040258852
    Abstract: An acid anhydride of the formula (4), and a polyimide using the acid anhydride, 1
    Type: Application
    Filed: June 17, 2004
    Publication date: December 23, 2004
    Inventors: Daisuke Ohno, Kenji Ishii, Yasumasa Norisue, Masamichi Mizukami, Atsushi Hirashima
  • Patent number: 6727370
    Abstract: Oxydiphthalic anhydrides such as 4-oxydiphthalic anhydride are prepared by the reaction of a halophthalic anhydride with an alkali metal carbonate such as potassium carbonate in the presence of a catalyst system comprising an alkali metal bicarbonate such as potassium bicarbonate and a phase transfer catalyst, preferably a tetraarylphosphonium halide.
    Type: Grant
    Filed: February 24, 2003
    Date of Patent: April 27, 2004
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, Qing Ye
  • Patent number: 6710187
    Abstract: A process to isolate dianhydride from an exchange reaction comprises extracting a bisimide/anhydride exchange reaction aqueous phase with an organic solution comprising an exchange catalyst at a first temperature and pressure to form an extracted aqueous phase comprising water, exchange catalyst and a dianhydride precursor; removing water from the extracted aqueous phase at a second temperature and pressure to form a molten phase, wherein the second pressure is less than the first pressure; removing water and exchange catalyst from the molten phase at a third temperature and pressure to form an isolation mixture; and converting the dianhydride precursor in the isolation mixture to dianhydride at a fourth temperature and pressure, wherein the fourth temperature is greater than the second and third temperatures and the fourth pressure is less than the second and third pressures.
    Type: Grant
    Filed: May 14, 2002
    Date of Patent: March 23, 2004
    Assignee: General Electric Company
    Inventors: Thomas Link Guggenheim, David Anthony Mongilio
  • Patent number: 6706897
    Abstract: Oxydiphthalic anhydrides such as 4-oxydiphthalic anhydride are prepared by the reaction of a halophthalic anhydride with an alkali metal carbonate such as potassium carbonate. The reaction proceeds in the presence of a hexaalkylguaninium halide or &agr;,&ohgr;-bis(pentaalkylguanidinium)alkane halide as a phase transfer catalyst.
    Type: Grant
    Filed: February 24, 2003
    Date of Patent: March 16, 2004
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, Qing Ye
  • Publication number: 20030220510
    Abstract: A process to isolate dianhydride from an exchange reaction comprises extracting a bisimide/anhydride exchange reaction aqueous phase with an organic solution comprising an exchange catalyst at a first temperature and pressure to form an extracted aqueous phase comprising water, exchange catalyst and a dianhydride precursor; removing water from the extracted aqueous phase at a second temperature and pressure to form a molten phase, wherein the second pressure is less than the first pressure; removing water and exchange catalyst from the molten phase at a third temperature and pressure to form an isolation mixture; and converting the dianhydride precursor in the isolation mixture to dianhydride at a fourth temperature and pressure, wherein the fourth temperature is greater than the second and third temperatures and the fourth pressure is less than the second and third pressures.
    Type: Application
    Filed: May 14, 2002
    Publication date: November 27, 2003
    Inventors: Thomas Link Guggenheim, David Anthony Mongilio
  • Patent number: 6600053
    Abstract: A 6,6′-dialkyl-3,3′,4,4′-biphenyltetracarboxylic dianhydride is prepared by brominating a 4-alkylphthalic anhydride at its 5-position, and coupling the bromination product in the presence of a nickel catalyst; A photosensitive resin composition containing a polyimide precursor having repetitive units of general formula (7) is applied onto a substrate, exposed to i-line, developed and heated to form a polyimide relief pattern. wherein Y is a divalent organic group, R7 and R8 are OH or a monovalent organic group, R9 and R10 are a monovalent hydrocarbon group, R11, R12 and R13 are a monovalent hydrocarbon group, a and b are an integer of 0 to 2, c is an integer of 0 to 4, and m is an integer of 0 to 3.
    Type: Grant
    Filed: August 30, 2001
    Date of Patent: July 29, 2003
    Assignees: Hitachi Chemical DuPont Microsystems Ltd., Hitachi Chemical DuPont Microsystems L.L.C.
    Inventors: Noriyoshi Arai, Makoto Kaji, Akihiro Sasaki, Toshiki Hagiwara
  • Patent number: 6590108
    Abstract: A method for the synthesis of a dianhydride comprises transimidation of bis (imide) (IV) in the presence of a substituted phthalic anhydride or 4-substituted tetrahydrophthalic anhydride to yield dianhydride (V)
    Type: Grant
    Filed: October 22, 2002
    Date of Patent: July 8, 2003
    Assignee: General Electric Company
    Inventors: Roy Ray Odle, Thomas Link Guggenheim, William James Swatos, Michael J. Vollmer
  • Publication number: 20020037991
    Abstract: A 6,6′-dialkyl-3,3′,4,4′-biphenyltetracarboxylic dianhydride is prepared by brominating a 4-alkylphthalic anhydride at its 5-position, and coupling the bromination product in the presence of a nickel catalyst; A photosensitive resin composition containing a polyimide precursor having repetitive units of general formula (7) is applied onto a substrate, exposed to 1-line, developed and heated to form a polyimide relief pattern.
    Type: Application
    Filed: August 30, 2001
    Publication date: March 28, 2002
    Applicant: Hitachi Chemical DuPont MicroSystems Ltd.
    Inventors: Noriyoshi Arai, Makoto Kaji, Akihiro Sasaki, Toshiki Hagiwara
  • Patent number: 6204394
    Abstract: Disclosed is a method for preparing oxy-diphthalic anhydrides, which comprises reacting a halo-phthalic anhydride represented by the formula (1): where Hal represents F, Cl, Br or I, with a carbonate salt selected from the group consisting of lithium carbonate, sodium carbonate, magnesium carbonate and calcium carbonate in a solvent to prepare oxy-diphthalic anhydrides represented by the formula (2):
    Type: Grant
    Filed: July 14, 1999
    Date of Patent: March 20, 2001
    Assignee: Manac Inc.
    Inventors: Junichi Sakata, Shinsuke Inoue, Shinichi Kadono
  • Patent number: 6060575
    Abstract: The present invention provides a series of easily processable poly(ether-imide)s that are organic-soluble and can afford colorless films, their organic solutions and their manufacturing process. The poly(ether-imide) is prepared from a dianhydride and a diamine, wherein the dianhydride is a bis(ether anhydride) having tert-butyl group, i. e. 1,4-bis(3,4-dicarboxyphenoxy)-2-tert-butylbenzene dianhydride.
    Type: Grant
    Filed: April 27, 1999
    Date of Patent: May 9, 2000
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Sheng-Huei Hsiao
  • Patent number: 6031061
    Abstract: A bis(trisubstitutedtrimellitic anhydride) derivative and a polyesterimide for optical communications, the polyesterimide being formed therefrom. The polyesterimide has a high refractive index, so that when using such polyesterimide as a material for a core of an optical fiber, the range of materials that can be selected for the cladding becomes wide. Also, a coating property and adhesion to a substrate are improved, thereby providing a good film forming property and thermal stability. Also, because the polyesterimide can minimize optical loss at a near infrared wavelength range, the polyesterimide is very useful as an optical material in the optical communications field adopting the light of near infrared wavelength.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: February 29, 2000
    Assignee: SamSung Electronics Co., Ltd.
    Inventors: Dong-hack Suh, Sun-young Chung, Tae-hyung Rhee
  • Patent number: 6028203
    Abstract: Oxybisphthalic compounds such as 4,4'-oxybis(N-methylphthalimide) and 4,4'-oxybis(phthalic anhydride) are prepared from the corresponding nitro- or halo-substituted phthalic compounds by reaction with an alkanoate or carbonate salt in a non-polar solvent and in the presence of a hexaalkylguanidinium salt as phase transfer catalyst. A carboxylic acid such as 4-chlorobenzoic acid may be used as an additional catalyst. Reaction rates and yields are higher than with other phase transfer catalysts.
    Type: Grant
    Filed: December 14, 1998
    Date of Patent: February 22, 2000
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, Thomas Link Guggenheim
  • Patent number: 5849934
    Abstract: A perfluorinated polyimide comprising a repeating unit represented by general formula (1): ##STR1## and a perfluorinated poly(amic acid) comprising a repeating unit represented by general formula (6): ##STR2## wherein R.sub.1 is a tetravalent organic group; and R.sub.2 is a divalent organic group, provided that chemical bonds between carbon atoms and monovalent elements contained in R.sub.1 and R.sub.2 are exclusively carbon-to-fluorine bonds; methods for preparing them; and optical material including the perfluorinated polyimide. 1,4-Bis(3,4-dicarboxytrifluorophenoxy)-tetrafluorobenzene dianhydride, 1,4-difluoropyromellitic anhydride, 1,4-bis(3,4-dicarboxytrifluorophenoxy)-tetrafluorobenzene, 1,4-difluoropyromellitic acid, and 1,4-bis(3,4-dicyanotrifluorophenoxy)-tetrafluorobenzene as well as methods preparing them. The perfluorinated polyimide has a thermal stability and has a low optical loss in an optical communication wavelength region (0.8 to 1.7 .mu.m).
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: December 15, 1998
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
  • Patent number: 5750731
    Abstract: A perfluorinated aromatic compound represented by general formula (7): ##STR1## wherein R.sub.3 is a tetravalent perfluorinated aromatic group represented by formula (8): ##STR2## wherein (R.sub.4)s are the same, each being a carboxyl group or a cyano group, or two adjacent (R.sub.4)s combine to form a divalent group represented by formula (10): ##STR3## provided that when R.sub.4 is a cyano group, R.sub.3 denotes said tetravalent perfluorinated aromatic group represented by formula (9).
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: May 12, 1998
    Assignee: Nippon Telegraph & Telephone Corporation
    Inventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
  • Patent number: 5675020
    Abstract: Disclosed herein are novel poly(imide-ethers) containing ortho substitution in the main chain of the polymer. These polymers are made from novel aromatic bis-carboxylic anhydrides which contain two ether groups attached to an aromatic ring in ortho positions to each other. The polymers are particularly useful for films, fibers and encapsulation, as well as thermoplastics.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: October 7, 1997
    Assignee: The University of Liverpool
    Inventors: Geoffrey Charles Eastmond, Jerzy Paprotny
  • Patent number: 5412009
    Abstract: The invention provides a compound of general formula I ##STR1## in which X represents a direct bond or a ##STR2## group.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: May 2, 1995
    Assignee: FMC Corportion (UK) Limited
    Inventors: Michael J. Schneider, James Gainer
  • Patent number: 5342968
    Abstract: A process for making relatively high purity eulfonylbis(phthalic anhydride) is provided. 3,3',4,4'-tetramethyl diphenyl sulfone is catalytically oxidized in a solvent under liquid phase elevated temperature and pressure conditions. The catalyst is constituted by cobalt, manganese, zirconium, and bromine. Sulfonylbis(phthalic) acid is recovered by crystallization and is then heated to produce the anhydride. Preferably, the acid is purified prior to dehydration.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: August 30, 1994
    Assignee: Amoco Corporation
    Inventors: Stephen P. Brugge, Juergen K. Holzhauer, Thomas E. Wolff
  • Patent number: 5336788
    Abstract: Disclosed is a method of making oxydiphthalic anhydride from oxydiphthalic acid. The oxydiphthalic acid is mixed with an organic liquid that codistills with water and the resulting slurry is heated to the boiling point of the slurry to remove any water. About 1 to about 4 moles of acetic anhydride per mole of oxydiphthalic acid are added to the slurry and the slurry is heated to a temperature between 50.degree. and 160.degree. C. until the oxydiphthalic acid content thereof is less than 0.1 weight percent. The slurry is filtered and the filter cake is heated to a temperature between about 180.degree. C. and below its melting point for about 12 to about 24 hours.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: August 9, 1994
    Assignee: Occidental Chemical Corporation
    Inventor: Viesturs Lesins
  • Patent number: 5336787
    Abstract: A process of making poly(dianhydride) compounds having formulae (I) and (II): ##STR1## where m is 0 to 50. ##STR2## wherein n is 0 to 20 and X is bond junction, oxygen atom, sulfur atom, SO.sub.2, C(CF.sub.3), CO, C(CH.sub.3).sub.2, CF.sub.2 --O--CF.sub.2, CH.sub.2, and CHOH.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: August 9, 1994
    Assignee: Olin Corporation
    Inventors: Murray A. Ruggiero, Renata C. Stegmeier, Bruce A. Marien, Keith O. Wilbourn
  • Patent number: 5274126
    Abstract: A compound of the formula ##STR1## and the dianhydride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of at least 2 heavy metal salts and also bromine in an acid organic medium. The compounds can be employed for the preparation of partially fluorinated polycondensates, such as polyimides, polycarboxamides, esters of polyamidecarboxylic acids, polyamides and imide-oligomers.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: December 28, 1993
    Assignee: Hoechst AG
    Inventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
  • Patent number: 5258530
    Abstract: A process for producing a biphenyltetracarboxylic dianhydride which comprises the step of: heating phthalic anhydride at a temperature of from 135.degree. to 300.degree. C. in the presence of a palladium catalyst thereby to allow the phthalic anhydride to undergo a dimerization reaction. According to the process, biphenyltetracarboxylic dianhydride can be synthesized by the direct dimerization of phthalic anhydride.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: November 2, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Yoshio Katsuro, Hitoshi Matsuda
  • Patent number: 5235070
    Abstract: A method for reducing the formation of dust produced by solid aromatic anhydrides, and aromatic anhydride compositions that have a reduced tendency to emit aromatic anhydride dust, are disclosed. The method comprises treating the aromatic anhydride with low levels of suitable organic compounds.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: August 10, 1993
    Assignee: Amoco Corporation
    Inventors: Michael R. Green, Chang M. Park, Adel B. Abdul-Malek
  • Patent number: 5206335
    Abstract: Poly(dianhydride) compounds having formulae (I) and (II): ##STR1## where m is 0 to 50. ##STR2## wherein n is 0 to 20 and X is bond junction, oxygen atom, sulfur atom, SO.sub.2, C(CF.sub.3), CO, C(CH.sub.3).sub.2, CF.sub.1 --O--CF.sub.2, CH.sub.2, and CHOH.The compounds are intermediates for certain resins.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: April 27, 1993
    Assignee: Olin Corporation
    Inventors: Bruce A. Marien, Keith O. Wilbourn
  • Patent number: 5198555
    Abstract: The invention relates to the preparation of novel dianhydrides of the formula: ##STR1## wherein R is a polyalkylated mononuclear aromatic radical, preferably a phenylene radical. The mononuclear aromatic radical may be substituted with from three to four lower alkyl radicals, preferably C.sub.1 -C.sub.4 alkyl radicals. The dianhydrides are preferably made by the reaction of a monoanhydride monoacid halide and a polyalkylated mononuclear aromatic in the presence of a Friedel-Crafts catalyst under Friedel-Crafts reaction conditions. These dianhydrides ae useful reactants in the preparation of polyimides and epoxy curing agents.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: March 30, 1993
    Assignee: Amoco Corporation
    Inventors: Vincent F. Smith, Jr., Gary J. Gudac
  • Patent number: 5194633
    Abstract: A process for preparing 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl) propane anhydride is disclosed. 1,1,1,3,3,3-hexafluoro-2,2-di(3,4 -dimethylphenyl) propane is oxidized under liquid phase conditions in the presence of an oxygen-containing gas, bromine and heavy metal catalyst components to 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl) propane in high yield. Addition of an anhydride of a low molecular weight carboxylic acid to the oxidation reaction mixture converts the 1,1,1-hexafluoro-2,2-di(3,4-dicarboxyphenyl)propane to 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl) propane anhydride.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: March 16, 1993
    Assignee: Amoco Corporation
    Inventors: Walter Partenheimer, Douglas E. Fjare, Gayle G. Chany