Nitrogen-containing Reactant Contains An Amine Group Patents (Class 528/229)
  • Patent number: 6927274
    Abstract: Polyimide precursors contained in resin compositions of the present invention have a polymer structure unit represented by formula (1) below: wherein chemical structure A2 includes an alicyclic compound but not an aromatic compound such as a benzene ring so that they provide excellent light transmission over a wide wavelength range. The polyimide precursors are imidized at 7.5% or more and 36% or less so that they are less soluble in developing solutions and therefore are not dissolved in the developing solutions at unexposed parts. Thus, the resin compositions of the present invention can be used to form a resin film having a precise pattern by exposure and development.
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: August 9, 2005
    Assignee: Sony Chemicals Corp.
    Inventors: Mamiko Nomura, Masatoshi Hasegawa, Junichi Ishii, Tadashi Akamatsu
  • Patent number: 6924348
    Abstract: A polyimide excelling in heat resistance, chemical resistance, water repellency, dielectric characteristics, electrical characteristics, and optical characteristics and a polyamide acid useful as the raw material therefor are provided. Specifically, a polyamide acid containing a chlorine atom and a fluorine atom and comprising a repeating unit represented by the following formula (1): (wherein X and X? independently denote a divalent organic group; Y and Y? independently denote a chlorine, bromine, or iodine atom; p and p? denote independently denote the number of fluorine atom {F in the formula (1)} bonded to the relevant benzene ring, representing an integer of 0-3; q and q? independently denote an integer of 0-3; and p+q total 3, and p?+q? total 3).
    Type: Grant
    Filed: July 11, 2002
    Date of Patent: August 2, 2005
    Assignees: Nippon Shokubai Co., Ltd., NTT Advanced Technology Corporation
    Inventors: Kozo Tajiri, Masayoshi Kuwabara, Yasunori Okumura, Tohru Matsuura, Noriyoshi Yamada
  • Patent number: 6919422
    Abstract: A polyimide composition and a process to prepare polyimide resins with reduced plate out and mold deposits is described. During resin molding operations the low plate out resins show a longer period of operation between cleaning of equipment leading to more efficient operation.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: July 19, 2005
    Assignee: General Electric Company
    Inventors: Robert R Gallucci, Roy Ray Odle, William A. Kernick, III, Mark Alan Sanner
  • Patent number: 6919418
    Abstract: Methods of reducing the amount of undesirable cyclic oligomer by-products in the production of polyetherimides are disclosed. The resulting polyetherimides have enhanced thermomechanical properties.
    Type: Grant
    Filed: August 25, 2003
    Date of Patent: July 19, 2005
    Inventors: Farid Fouad Khouri, Daniel Joseph Brunelle, Donald Scott Johnson
  • Patent number: 6916898
    Abstract: A process of preparing a polyimide of the present invention comprises effecting an imidization reaction of a diamine and a tetracarboxylic dianhydride in a solvent containing 50 to 100% by weight of an equimolar composition of a nitrogen-containing cyclic compound indicated by chemical formula (1) below and a phenol indicated by chemical formula (2) below: in formula (1), X represents —CH2— or —N(CH3)—, and in formula (2), R1 and R2 may be the same as, or different from, each other and represent each any one of —H, —OH, —CH3, —C2H5, —C3H7, —C4H9, —C5H11, —C6H13, —C7H15, —C8H17, —C9H19, —C10H21, —OCH3, —O(C6H5), —NO2, —Cl, —Br and —F.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: July 12, 2005
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Takashi Kuroki, Atsushi Shibuya, Shoji Tamai
  • Patent number: 6911296
    Abstract: The present invention also includes an imageable element, comprising a substrate and a thermally imageable composition comprising a thermally sensitive polymer which exhibits an increased solubility in an aqueous developer solution upon heating. The thermally sensitive polymer includes at least one covalently bonded unit and at least one thermally reversible non-covalently bonded unit, which includes a two or more centered H-bond within each of the non-covalently bonded unit. The present invention also includes a method of producing the imaged element. The present invention still further includes a thermally imageable composition comprising comprising a thermally sensitive polymer according to the present invention and a process for preparing the thermally sensitive polymer, which is a supramolecular polymer.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: June 28, 2005
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Peter S. Pappas, Alan Monk, Shashikant Saraiya, Jianbing Huang
  • Patent number: 6911519
    Abstract: A series of low melting and low viscosity phenylethynyl end-capped polyimides (PETIs) possessed of long term thermal and mechanical stability useful as films, melt coatings, adhesives, matrix and RTM resins and particular as coatings for optical fibers and phenylethynyl end-capped bismides blended with PETIs are disclosed. Processes for their production including: 1) modification of PETI-5 oligomer by molecular weight adjustments by blending with reactive low melting phenylethynyl end-capped imide monomers, 2) modification of the PETI-5 backbone structure with other diamine components, and 3) modification of the PETI-5 backbone with bulky fluorinated groups are also disclosed.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: June 28, 2005
    Assignee: University of Connecticut
    Inventors: Daniel A. Scola, Christopher D. Simone
  • Patent number: 6908685
    Abstract: The invention provides a polyimide film manufactured from a polyamic acid prepared from pyromellitic dianhydride in combination with 10 to 60 mol % of phenylenediamine and 40 to 90 mol % of 3,4?-oxydianiline, based on the overall diamine. The polyimide film, when used as a metal interconnect board substrate in flexible circuits, chip scale packages (CSP), ball grid arrays (BGA) or tape-automated bonding (TAB) tape by providing metal interconnects on the surface thereof, achieves a good balance between a high elastic modulus, a low thermal expansion coefficient, alkali etchability and film formability.
    Type: Grant
    Filed: August 23, 2001
    Date of Patent: June 21, 2005
    Assignees: E. I. du Pont de Nemours and Company, DuPont-Toray Co. Ltd.
    Inventors: Kenji Uhara, Kouichi Sawasaki, Naofumi Yasuda, Brian C. Auman, John D. Summers
  • Patent number: 6891067
    Abstract: The present invention provides an optical polyimide precursor for use in making a polyimide. The precursor is defined by the following formula: wherein X is Cl, Br, oxo-halide, or fully halogenated alkyl, and A is a divalent aromatic or halogenated aromatic moiety. The present invention provides a method of preparing a diamine compound for use as an optical polyimide precursor. The method includes the steps of dissolving 2-chloro-5-nitrobenzotrifluoride and a diol in N,N-dimethylacetamide to form a solution, adding potassium carbonate, tert-butylammonium chloride and copper powder to said solution and heating the resulting mixture, removing the copper, precipitating and recrystallizing a dinitro-compound resulting from heating the mixture, and dissolving the dinitro-compound and reducing the dinitro-compound to yield a diamine compound.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: May 10, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kyung-Hee You, Kwan-Soo Han, Tae-Hyung Rhee, Eun-Ji Kim, Jung-Hee Kim, Woo-Hyeuk Jang
  • Patent number: 6887580
    Abstract: An adhesive polyimide resin which comprises a siloxane polyimide resin obtained from (A) an aromatic tetracarboxylic dianhydride and (B) a diamine ingredient comprising (B1) a diamine having a phenolic hydroxyl group, carboxyl group, or vinyl group as a crosslinkable reactive group and (B2) a siloxanediamine and has a glass transition temperature of 50 to 250?C and a Young's modulus (storage modulus) at 250?C of 105 Pa or higher; and a laminate which comprises a substrate comprising a conductor layer and an insulating supporting layer having at least one polyimide resin layer and, disposed on a surface of the substrate, an adhesive layer comprising a layer of the adhesive polyimide resin. The adhesive polyimide resin and the laminate have satisfactory adhesion strength even after exposure to a high temperature of up to 270?C and further have excellent heat resistance in reflow ovens. They are hence suitable for use in the bonding of electronic parts.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: May 3, 2005
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Kiwamu Tokuhisa, Akira Tokumitsu, Kazuaki Kaneko
  • Patent number: 6887967
    Abstract: A thermosetting polyimide resin composition is provided which comprises a polyimide resin and an epoxy resin, which has excellent heat resistance, low dielectric constant and low dielectric loss tangent and also yields a cured article having good mechanical properties such as tensile strength and tensile elongation. Also, a process for producing a polyimide resin used in the polyimide resin composition is provided. The thermosetting polyimide resin composition comprises a polyimide resin (X), which has a carboxyl group and a linear hydrocarbon structure having a number-average molecular weight of 300 to 6,000, and an epoxy resin (Y).
    Type: Grant
    Filed: January 23, 2003
    Date of Patent: May 3, 2005
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Eiju Ichinose, Yohzoh Yamashina, Hidenobu Ishikawa
  • 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
  • Patent number: 6861497
    Abstract: A polyimide is disclosed of the formula: CG1 and CG2 are independently electron-accepting and/or electron-donating groups; x is an integer from about 3 to about 3000; ODAH is any of a number of known dianhydride residues; ODAM is any of a number of known diamine residues; and m, n, o, and p cumulatively add to 1.0, with the sum of m and n ranging from about 0.05 to about 1.0, the sum of o and p ranging from about 0 to about 0.95, the sum of m and o being about 0.5 and the sum of n and p being about 0.5. In addition, a film structure comprising the polyimide and devices utilizing the film structure are disclosed.
    Type: Grant
    Filed: October 28, 2002
    Date of Patent: March 1, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Geoffrey A. Lindsay, Richard A. Hollins, Peter Zaras, Andrew J. Guenthner, Andrew P. Chafin, Mathew C. Davis, Stephen Fallis
  • Patent number: 6855776
    Abstract: Improved amine-terminated polybutadienes (ATPBs) having one or two terminal groups of the formula —CHRNH2 wherein R is C1-C20 alkyl, are prepared by aminating a secondary hydroxyl-terminated polybutadiene having no ether groups. The ATPBs may be hydrogenated or partially hydrogenated, either prior to or after the animation, to saturate or partially saturate the polymers. Preferred ATPBs are of the formula H2NCHR-(polybutadiene)-CHRNH2 wherein R is C1-C20 alkyl. Polyureas, polyurethanes, crosslinked epoxies, polyamides, and other derivatives with improved properties can be prepared from the ATPBs. The resultant derivatives are useful in liquid binders for braking systems, electric potting compositions, coatings, adhesives, sealants, and water proofing membranes, for example.
    Type: Grant
    Filed: November 20, 2002
    Date of Patent: February 15, 2005
    Assignee: Sartomer Technology Company, Inc.
    Inventors: Herbert Shin-I Chao, John Schmidhauser, Alain Robert Drexler, Nan Tian
  • Patent number: 6852826
    Abstract: In a step of polymerizing polyamic acid by mixing tetracarboxylic acid dianhydride and diamine and polycondensating the tetracarboxylic acid dianhydride and diamine under the presence of a polymerization-use solvent, a tetracarboxylic acid dianhydride slurry in which a tetracarboxylic acid dianhydride is dispersed in a dispersion medium is used. According to this, it is possible to directly manufacture a polyamic acid solution having a high concentration of polyamic acid more than or equal to 10% by weight. Especially, even if a tetracarboxylic acid dianhydride having low solubility in the polymerization-use solvent, it is possible to effectively manufacture a polyamic acid solution having high solids content, by a simple process and in a short time.
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: February 8, 2005
    Assignee: Kanera Corporation
    Inventors: Kan Fujihara, Kazuhiro Ono, Kiyokazu Akahori
  • Patent number: 6849706
    Abstract: Copolyetherimides comprise phthalimide structural units comprising both 3- and 4-linkages, wherein the designations 3-linkage and 4-linkage refer to the isomeric positions on the phthalimide ring in the totality of phthalimide-comprising structural units in the copolymer. The products have excellent properties, including high glass transition and heat distortion temperatures, high ductility and good melt flow properties, and low polydispersity.
    Type: Grant
    Filed: August 25, 2003
    Date of Patent: February 1, 2005
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, Havva Yagci Acar, Farid Fouad Khouri, William David Richards
  • Patent number: 6808818
    Abstract: A fusible polyimide showing a fusion endothermic peak in a differential scanning calorimeter has a recurring unit of the following formula (1): in which Ar1 is a mixture of residues of tetracarboxylic dianhydrides composed of 12-25 mol. & of a residue of pyromellitic dianhydride, 5-15 mol. % of a residue of 3,3′4,4′-benzophenonetetracarboxylic dianhydride, and a remaining mol. % of a residue of 3,3′,4,4′-biphenyltetracarboxylic dianhydride, and Ar2 is an aromatic diamine residue composed of 1,3-bis(4-aminophenoxy)benzene.
    Type: Grant
    Filed: October 11, 2002
    Date of Patent: October 26, 2004
    Assignee: Ube Industries, Ltd.
    Inventors: Hideki Ozawa, Shigeru Yamamoto
  • Patent number: 6784276
    Abstract: This invention is a highly concentrated stable solution of polyimide precursors (monomers) having a solids content ranging from about 80 to 98 percent by weight in lower aliphatic alcohols i.e. methyl and/or ethyl alcohol. The concentrated polyimide precursor solution comprises effective amounts of at least one aromatic diamine, at least one aromatic dianhydride or a lower molecular weight alkyl ester of said dianhydride, and a monofunctional endcap including monoamines, monoanhydrides and the lower alkyl esters of said monoanhydrides. These concentrated polyimide precursor solutions are particularly useful for the preparation of fibrous prepregs and composites for use in structural materials for military and civil applications.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: August 31, 2004
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventor: Chun-Hua Chuang
  • Patent number: 6780960
    Abstract: A method of making a solution of a polyimide from a diamine monomer and a dianhydride monomer is disclosed. A solution or slurry of one of the monomers in a solvent that boils at a temperature between about 80° C. and about 160° C. is prepared. The solution or slurry is heated to a temperature between about 80° C. and about 160° C. and the other monomer is slowly added to the solution or slurry. Polyamic acid that is formed quickly imidizes to form the polyimide.
    Type: Grant
    Filed: July 22, 2002
    Date of Patent: August 24, 2004
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Michael C. Hausladen, Jin-O Choi
  • Patent number: 6777525
    Abstract: Polyimides having a desired combination of high thermo-oxidative stability, low moisture absorption and excellent chemical and corrosion resistance are prepared by reacting a mixture of compounds including (a) 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (BTDA), (b) 3,4′-oxydianiline (3,4′-ODA), and (c) 5-norbornene-2,3-dicarboxylic anhydride (NA) in a high boiling, aprotic solvent to give 5 to 35% by weight of polyamic acid solution. The ratio of (a), (b), and (c) is selected to afford a family of polyimides having different molecular weights and properties. The mixture first forms a polyamic acid precursor. Upon heating at or above 300° C., the polyamic acids form polyimides, which are particularly suitable for use as a high temperature coating, adhesive, thin film, or composite matrix resin.
    Type: Grant
    Filed: April 1, 2002
    Date of Patent: August 17, 2004
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Ruth H. Pater
  • Patent number: 6770733
    Abstract: A film-formable polyimide copolymer, which comprises two kinds of tetracarboxylic acid dianhydride consisting of (A) pyromellitic acid dianhydride and (B) 3,3′,4,4′-benzophenonetetracarboxylic acid dianhydride, and (C) 6-amino-2-(p-aminophenyl)benzimidazole has a heat-resistant dimensional stability without any deterioration of mechanical properties inherent in the polyimide resin when used as a film.
    Type: Grant
    Filed: January 3, 2003
    Date of Patent: August 3, 2004
    Assignee: Nippon Mektron, Limited
    Inventors: Min Zuo, Jenq-Tain Lin
  • Patent number: 6756418
    Abstract: New polymers, compositions comprising these polymers, and methods of using these compositions are provided. The polymers comprise styrene and maleic anhydride monomers with at least some of the maleic anhydride monomers having certain functional groups bonded thereto. Preferred functional groups include those derived from adhesion promoters (e.g., 2-aminophenol), photoinitiators (e.g., 4-aminoacetophenone), and solubilizers (e.g., 4-aminobenzoic acid). The polymers can be incorporated according to conventional processes into compositions which are then used to form a color filter to be used in a liquid crystal display. The final color filter has a high resolution, is highly resistant to solvents typically used in the color filter manufacturing process, is strongly adhered to the color filter substrate, has superior optical clarity, is highly soluble in a wide range of alkali developers, and has excellent heat and UV light stability.
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: June 29, 2004
    Assignee: Brewer Science Inc.
    Inventors: Gu Xu, Dan W. Brewer, Timothy Limmer, Mike Stroder, Shelly Fowler, Jonathon Mayo
  • Patent number: 6740371
    Abstract: An alkyldiamine having excellent polymerization reactivity, a polyimide comprising it as a constituting element, and a liquid crystal alignment film excellent in uniformity of liquid crystal alignment, are presented. Namely, the present invention relates to a diaminobenzene derivative represented by the following general formula (1) and to a polyimide obtained by reacting a diamine containing at least 1 mol % of the diaminobenzene derivative represented by the general formula (1), with at least one compound selected from a tetracarboxylic. dianhydride and its derivatives, to obtain a polyimide. precursor having a reduced viscosity of from 0.05 to 5.0 dl/g (in N-methylpyrrolidone at a temperature of 30° C., concentration: 0.5 g/dl) and ring-closing it, and having a repeating unit represented by the general formula (2). Further, the present invention relates to a liquid crystal alignment film containing at least 1 mol % of the above repeating unit.
    Type: Grant
    Filed: December 26, 2001
    Date of Patent: May 25, 2004
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kazuyoshi Hosaka, Hideyuki Nawata, Takayasu Nihira, Hideyuki Isogai, Hideyuki Endou, Hiroyoshi Fukuro
  • Patent number: 6737502
    Abstract: A solvent-free, catalyst-free and contamination-free method of synthesis of polyimides is disclosed. The method includes polymerizing a diamine with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) at a pressure of 0.1-760 mm Hg, preferably a reduced pressure at about 36 mm Hg, and a temperature of 90-400° C., preferably 10-240° C.
    Type: Grant
    Filed: June 6, 2002
    Date of Patent: May 18, 2004
    Assignee: Chung-Shan Institute of Science & Technology
    Inventor: Shean-Jeng Jong
  • Patent number: 6737503
    Abstract: The aromatic diamine compound of the present invention is represented by the following formula (1), and from the aromatic diamine compound a polyimide having a repeating unit represented by the following formula (4), which has low-temperature adherability, can be obtained. In the formulas (1) and (4), n is an integer of 3 to 7, each R is independently an atom or a group selected from the group consisting of a hydrogen atom, a halogen atom and a hydrocarbon group, the same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on at least one benzene ring, and when n is 3, the hetero atoms are at the ortho- or meta-positions to each other on all the benzene rings. In the formula (4), Y is a tetravalent organic group.
    Type: Grant
    Filed: September 3, 2002
    Date of Patent: May 18, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yoichi Kodama, Minehiro Mori, Naoshi Nagai, Masaru Kawaguchi
  • Patent number: 6734276
    Abstract: The invention is a polyimide, random copolymer having repeating units of the formula (1): wherein R1 and R2 each represent a divalent group selected from and R1 and R2 may be the same or different; and x=0.60 to 0.80, y+z=0.40 to 0.20, and x+y+z=1.00, and a linear expansion coefficient at 100 to 200° C. is in the range of from 10 to 20 ppm/K. This is a useful polyimide that can be a polyimide circuit substrate material capable of keeping flat, neither shrinking nor expanding in its laminate.
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: May 11, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Wataru Yamashita, Katsuji Watanabe, Takahisa Oguchi
  • Patent number: 6713597
    Abstract: A process for the preparation of a reactive friable polyimide powder comprises dissolving an aromatic dianhydride and an organic diamine in a high-boiling, aprotic organic solvent to form a reaction solution; heating the reaction solution under imidization conditions to form an insoluble reactive polyimide and to effect substantially complete distillation of the water of reaction out of the reaction solution; and separating the insoluble reactive polyimide from the reaction solution to form a reactive friable polyimide powder.
    Type: Grant
    Filed: March 19, 2002
    Date of Patent: March 30, 2004
    Assignee: General Electric Company
    Inventor: Martin John Lindway
  • Patent number: 6710160
    Abstract: Disclosed are a polyamic acid having repeating units represented by the formula (1): wherein the norbornane skeleton of comprises four components of and their contents satisfy the following: 1%≦2,5-[diexo]≦90%, 1%≦2,5-[exo,endo]≦90%, 1%≦2,6-[diexo]≦90%, 1% ≦2,6-[exo,endo]≦90%, provided that (2,5-[diexo])+(2,5-[exo,endo])+(2,6-[diexo])+(2,6-[exo,endo])=100%, R represents from 4 to 27 carbon atoms, and represents a tetravalent group selected from the group consisting of an aliphatic group, a monocyclic aliphatic group, a condensed polycyclic aliphatic group, a monocyclic aromatic group, a condensed polycyclic aromatic group, and a non-condensed polycyclic aliphatic or aromatic group which is composed of cycloaliphatic or aromatic groups mutually bonded to each other either directly or via a crosslinking member; and a polyimide
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: March 23, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Wataru Yamashita, Katsuji Watanabe, Hideaki Oikawa, Hisato Ito
  • Patent number: 6693162
    Abstract: The present invention provides a polyimide resin, a resin composition, an adhesive solution, a film-state joining component, and an adhesive laminate film soluble in a solvent having excellent heat resistance and adhesion, capable of bonding and curing at relatively low temperatures.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: February 17, 2004
    Assignee: Kaneka Japan Corporation
    Inventors: Hiroyuki Tsuji, Hiroyuki Furutani, Koichiro Tanaka, Takeshi Kikuchi
  • Patent number: 6680363
    Abstract: An acid dianhydride, together with a diamine, is heated in an organic polar solvent in the presence of &ggr;-caprolactone or &bgr;-butyrolactone as an acid catalyst to prepare a polyimide having an average molecular weight of 10,000 to 300,000. This production process can realize the production of a polyimide which is soluble in a solvent and has high processability and stability.
    Type: Grant
    Filed: January 23, 2002
    Date of Patent: January 20, 2004
    Assignee: Hitachi Cable, Ltd.
    Inventors: Katsumoto Hosokawa, Yuuki Honda, Seiji Kamimura, Yoshiyuki Ando, Kenji Asano
  • Patent number: 6673890
    Abstract: A zwitterionic polyamine comprising a linear or branched hydrophobic polyamine backbone having 2 to 10 tertiary amino nitrogen atoms and a spacer between two tertiary nitrogen atoms wherein the spacer is, for example selected from C8-C16-alkylene, C5-C15-cyloalkylene, wherein in formula (IV) R═C1- to C22-alkyl or C7-C22-aralkyl and n=3 to 6, at least one tertiary amine end group of the polyamine backbone contains two groups having formula (V) or (VI), wherein A means an ethylene oxide unit, a propylene oxide unit, a unit of butylene oxides and a tetrahydrofuran unit, n is a number of from 1 to 50, X is an anionic group such as —SO3M, with the proviso that in formula (VI) one X may also be hydrogen and M is hydrogen, alkai metal or ammonium, or contains one group of formula (V) or (VI) and one group selected from radicals consisting of formula (VII), C1- to C22-alkyl and C7-C22-aralkyl the meaning of A and n is the same as in formula (V) or (VI), said zwitterionic polyetherpolyamine having a
    Type: Grant
    Filed: January 16, 2002
    Date of Patent: January 6, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Boeckh, Oliver Borzyk, Michael Ehle, Ralf Nöerenberg, Eugene P. Gosselink, Jeffrey S. DuPont, Robert H. Rohrbaugh, Kenneth N. Price, Randall S. Deinhammer
  • Patent number: 6673851
    Abstract: Self-photoinitiating liquid oligomeric compositions having tertiary amine groups are provided by Michael Addition reaction of: A) an uncrosslinked Michael Addition reaction product of a multifunctional acrylate acceptor and a Michael Donor; and B) a primary and/or secondary amine. The compositions can be crosslinked to make coatings, laminates and adhesives.
    Type: Grant
    Filed: October 12, 2001
    Date of Patent: January 6, 2004
    Assignee: Ashland Inc.
    Inventors: Thomas Michael Moy, R. Scott Harvey
  • Patent number: 6667382
    Abstract: The present invention provides an amine or polyamine, which has a surface activity not inferior to a solid tallow-based amine and an excellent workability. A salt of the amine is suited for emulsifying asphalt and the like, and also provides an asphalt emulsion composition which is obtained by using the salt and which has a quick setting property. Namely, the prevent invention provides a polyamine represented by the formula (1), a process for producing the amine, and an asphalt emulsion composition containing a water-soluble salt of the amine. wherein R is a straight or branched hydrocarbon group having 8 to 22 carbon atoms; x is a number of 1 to 5; and each of y and z is a number of 0 to 5 with the proviso that both of y and z are not 0 at the same time.
    Type: Grant
    Filed: November 1, 2000
    Date of Patent: December 23, 2003
    Assignee: Kao Corporation
    Inventors: Kazuo Isobe, Ryoichi Tamaki, Keiichiro Tomioka, Wataru Yoshida, Tetsuaki Fukushima, Uichiro Nishimoto
  • Patent number: 6653433
    Abstract: A polyimide film that exhibits improved peel strength when clad with a metal layer is prepared by reacting a polyamic acid polymer and an esterified polyamic acid oligomer. The esterified oligomer has from two to twenty repeating units and at least two crosslinkable groups selected from the group consisting of carbonyl, cyano, hydroxy, alkyne, maleimide, norbornene and sulfonyl groups. The polyamic acid is dissolved in a solvent to form a polyamic acid solution, which has a minimum gel-film forming temperature, or a minimum green film forming temperature, associated therewith. The esterified polyamic acid oligomer has an imidization temperature, which is higher than the minimum gel-film forming temperature, or the minimum green film forming temperature, of the polyamic acid solution.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: November 25, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: James Richard Edman, Meredith Lynn White
  • Patent number: 6642348
    Abstract: The present invention provides PMR-type polyimides that exhibit lower melt viscosities than PMR-type polyimides of the prior art. These PMR-type polyimides are created by incorporating flexible linkages, such as kinked structures and twisted or non-coplanar moietes into the backbone structure of the PMR. Specifically, the present invention provides for the production of PMR-type polyimides having 2,2′-disubstituted biaryls in the polymer backbone.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: November 4, 2003
    Assignee: The University of Akron
    Inventors: Ronald Eby, Michael Meador, Christopher Gariepy
  • Patent number: 6639042
    Abstract: New hyperbranched polymers having repeating units of the formula The polymer is prepared by the polymerization of the AB2 monomer N-{3,5-bis(4-hydroxybenzoyl)benzene}-4-fluoroisophthalimide.
    Type: Grant
    Filed: February 27, 2002
    Date of Patent: October 28, 2003
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Jong-Beom Baek, Loon-Seng Tan
  • Patent number: 6605688
    Abstract: This invention concerns low viscosity aldimine and ketimine reactive diluents having multi-imine functionality, which are useful in automotive refinish coating compositions, including a process for making them and the coatings that contain them.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: August 12, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Marko Strukelj
  • Patent number: 6600006
    Abstract: A polyamic ester prepared by partially substituting hydrogen atoms of carboxylic groups of a polyamic acid with acid labile groups, the polyamic ester comprising one or more repeating units represented by Formula 1, and each of at least one terminal of the polyamic ester molecule terminates with the same or different reactive end-capping monomer: wherein in Formula 1, R1 and R2 are independently a hydrogen atom, or an acid labile group; X is a tetravalent, an aromatic or an aliphatic organic group; Y is a divalent, an aromatic or an aliphatic organic group; and m is an integer equal to or greater than 1.
    Type: Grant
    Filed: December 31, 2001
    Date of Patent: July 29, 2003
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Myung Sup Jung, Sung Kyung Jung, Yong Young Park, Bong Seok Moon, Bong Kyu Kim
  • Patent number: 6596838
    Abstract: The invention relates to a semi-permeable membrane separation process and device in which the said membranes comprise sulphonated polyimides. The present invention also relates to the use of sulphonated polyimide membranes in separation processes and devices using semi-permeable membranes.
    Type: Grant
    Filed: August 17, 2001
    Date of Patent: July 22, 2003
    Assignees: Commissariat A l'Energie Atomique, Centre National de la Recherche
    Inventors: Michel Pinery, Gérald Pourcelly, Régis Mercier
  • Patent number: 6586555
    Abstract: This invention provides processes of the preparation of polyamides, polyimides, and polyamideimides, which are easy to purify after reactions, from polycarboxylic acids and polyamines in high yield without side reactions such as a change of color to black by direct polycondensation reaction with heat, especially processes of preparing aromatic polyamides (aramids), aromatic polyimides, and aromatic polyamideimides, which are difficult to synthesize in direct polycondensation reaction. Polyamides, polymides, and polyamideimides are prepared in high yield by the polycondensation of aromatic dicarboxylic acids, aromatic tetracarboxylic acids or aromatic tricarboxylic acids and aromatic diamines, using arylboric acids such as 3,4,5-trifluorophenylboric acids as polycondensation catalysts, in a mixed solvent of pentamethylbenzene and N-methylpyrrolidinone or a mixed solvent of m-terphenyl and N-butylpyrrolidinone.
    Type: Grant
    Filed: September 12, 2001
    Date of Patent: July 1, 2003
    Assignee: Japan Science and Technology Corporation
    Inventors: Kazuaki Ishihara, Hisashi Yamamoto
  • Patent number: 6586561
    Abstract: Sulfonated polyimide polymers incorporating bulky monomers are disclosed. The polymers have a liquid crystalline structure and exhibit high conductivity, high water uptake and water stability over a range of relative humidities and temperatures. The polymers are particularly adapted for use as a polymer electrolyte membrane in fuel cells.
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: July 1, 2003
    Assignee: Case Western Reserve University
    Inventors: Morton H. Litt, Robert F. Savinell, Jesse S. Wainright, Yue Zhang
  • Patent number: 6573357
    Abstract: The present invention relates to a process for the production of aliphatic ketimines having a polyalkylenepolyamine content of less than 1% by weight from the corresponding aliphatic ketones and polyalkylenepolyamines comprising the steps of: (a) forming a mixture of said aliphatic ketones and said polyalkylenepolyamines wherein the weight ratio of said ketone to said polyalkylenepolyamine is in the range of about 3.0:1 to about 10:1; (b) heating said mixture to a refluxing temperature between about 170° F. and 230° F. while continuously removing water to form the corresponding aliphatic ketimine; and (c) isolating said aliphatic ketimine.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: June 3, 2003
    Assignee: Resolution Performance Products LLC
    Inventors: Jenny Qinhong Ye, Michael Earl Beasley
  • Patent number: 6569984
    Abstract: The invention is directed to method for making a polyimide by converting the dianhydride to the ester acid and reacting the ester acid with a diamine. The invention allows for the controlled addition of aliphatic diamines resulting in control of the polyimide properties such as the glass transition temperature, solubility, and melt processability.
    Type: Grant
    Filed: April 27, 2001
    Date of Patent: May 27, 2003
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: James E. McGrath, Sue J. Mecham
  • Patent number: 6538100
    Abstract: The object of the present invention is to provide a method capable of producing polyimide resins having excellent heat resistance, which can utilize inexpensive monomers and does not use solvents. The method comprises mixing, in the absence of a solvent, a diamine and at least one tetracarboxylic acid component selected from the group consisting of a tetracarboxylic acid, a tetracarboxylic acid monoanhydride and a tetracarboxylic acid dianhydride capable of forming two imide rings upon cyclization, and then heat-treating the mixture.
    Type: Grant
    Filed: February 14, 2000
    Date of Patent: March 25, 2003
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Yoshiyuki Yamamori, Hiroyuki Yasuda
  • Patent number: 6538097
    Abstract: A process for production of polyimide powder, which comprises reacting a biphenyltetracarboxylic dianhydride and an aromatic diamine in an amide-based solvent optionally containing a water-soluble ketone, in the presence of an imidazole at 1-100 equivalent percent based on the carboxylic acid content of the polyimide precursor, separating and collecting the produced polyimide precursor powder from a water-soluble ketone solvent containing 3-30 wt % of an amide-based solvent, and heating the polyimide precursor powder to an imidation rate of 90% or greater, as well as polyimide powder obtained thereby, molded bodies of the polyimide powder, and a process for production of the molded bodies.
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: March 25, 2003
    Assignee: UBE Industries, Ltd.
    Inventors: Hiroaki Yamaguchi, Fumio Aoki
  • Patent number: 6534622
    Abstract: A process for production of polyimide powder, which comprises reacting an aromatic diamine with a partial ester of a biphenyltetracarboxylic dianhydride, which is a partial ester of a biphenyltetracarboxylic dianhydride with a primary alcohol of 1-5 carbon atoms of which at least 30 mole percent is a 2,3,3′,4′-biphenyltetracarboxylic acid component, in the presence of the primary alcohol, separating out and collecting the resulting solid polyimide precursor and heating for dehydrating ring closure, polyimide powder obtained thereby, molded bodies of the polyimide powder, and a process for production of the molded bodies.
    Type: Grant
    Filed: October 29, 2001
    Date of Patent: March 18, 2003
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroaki Yamaguchi, Fumio Aoki
  • Patent number: 6531568
    Abstract: This invention provides crosslinkable-group-containing polyimides of various known thermoplastic polyimide backbone structures, which are provided with far better heat resistance, chemical resistance and mechanical properties than known polyimides of the structures without impairing excellent moldability or formability, superb sliding property, low water absorption property, outstanding electrical properties, high thermal oxidation stability and high radiation resistance, all of which are inherent to the structures.
    Type: Grant
    Filed: April 9, 2001
    Date of Patent: March 11, 2003
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Atsushi Shibuya, Tomomi Okumura, Hideaki Oikawa, Yoshihiro Sakata, Takashi Kuroki, Yuichi Okawa, Shoji Tamai
  • Patent number: 6518392
    Abstract: A novel dielectric composition is provided that is useful in the manufacture of integrated circuit devices and integrated circuit packaging devices. The dielectric composition is prepared by imidizing and curing an oligomeric precursor compound comprised of a central polybenzoxazole, polybenzothiazole, polyamic acid or polyamic acid ester segment end-capped at each terminus with an aryl-substituted acetylene moiety such as an ortho-bis(arylethynyl)aryl group, e.g., 3,4-bis(phenylethynyl)phenyl. Integrated circuit devices, integrated circuit packaging devices, and methods of synthesis and manufacture are provided as well.
    Type: Grant
    Filed: March 8, 2001
    Date of Patent: February 11, 2003
    Assignee: International Business Machines Corporation
    Inventors: Kenneth R. Carter, James L. Hedrick, Victor Yee-Way Lee, Dale C. McHerron, Robert D. Miller
  • Patent number: 6500913
    Abstract: The present invention relates to a novel polyimide of the general formula (1) and a process for the preparation thereof.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: December 31, 2002
    Assignees: Council of Scientific and Industrial Research, Laboratoire des Materiaux Organiques a Proprietes Speciques
    Inventors: Jinu Suju Mathew, Subhash Pundlik Vernekar, Reges Mercier, Rachid Kerboua
  • Patent number: 6500904
    Abstract: A method for the synthesis of high molecular weight poly(imide)s comprising coupling poly(imide) precursors having complementary functional groups and a weight average molecular weight of less than about 50,000 Daltons to form high molecular weight poly (imides)s having a weight average molecular weight greater than 50,000 Daltons.
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: December 31, 2002
    Assignee: General Electric Company
    Inventor: Robert F. Hayes