Plural Chalcogens Bonded Directly To Ring Carbons Of Each Of The Two Five Membered Hetero Rings (e.g., Bisphthalimides, Etc.) Patents (Class 548/461)
  • Patent number: 11674045
    Abstract: A three-dimensional printing ink that has a viscosity suitable for three-dimensional printing, and improved performance.
    Type: Grant
    Filed: September 20, 2019
    Date of Patent: June 13, 2023
    Assignee: LG CHEM, LTD
    Inventors: Youngdae Kim, Bu Gon Shin, Sang Woo Kim, Seunghee Lee, Eun Ho Kho
  • Patent number: 10752603
    Abstract: A process for the purification of an oxydiphthalic anhydride includes contacting a mixture of an oxydiphthalic anhydride and at least one of the corresponding oxydiphthalic diacid, a corresponding oxydiphthalic tetraacid, a halophthalic anhydride, and a catalyst with a solvent to provide a slurry. The solvent is capable of solubilizing the corresponding oxydiphthalic diacid, the corresponding oxydiphthalic tetraacid, the halophthalic anhydride, and the catalyst at a temperature of 15 to 50° C., and the oxydiphthalic anhydride is substantially insoluble in the solvent at this temperature. The oxydiphthalic anhydride can be isolated from the slurry. A purified oxydiphthalic anhydride and a polyetherimide prepared therefrom are also disclosed.
    Type: Grant
    Filed: February 8, 2019
    Date of Patent: August 25, 2020
    Assignee: SABIC GLOBAL TECHNOLOGIES, B.V.
    Inventors: Hariharan Ramalingam, Tarun Kumar Pal, Meerakani Mohamed Ali Sait, Thomas Link Guggenheim, Lioba Maria Kloppenburg
  • Patent number: 9371426
    Abstract: Disclosed herein is a composition comprising a crosslinked organic polymer; wherein the composition has a coefficient of friction that is in a range of ±30% of a coefficient of friction for a composition comprising the same organic polymer that is not crosslinked; and wherein the composition has a lower K factor than a K factor of the composition comprising the same organic polymer that is not crosslinked; the coefficient of friction and the K factor being measured in a thrust washer apparatus as per ASTM D-3702, where the counter stationary surface in the thrust washer apparatus comprises carbon steel having a Rockwell C hardness of 18 to 22 and a 12 to 16 micro-inch surface finish.
    Type: Grant
    Filed: December 8, 2008
    Date of Patent: June 21, 2016
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Domenico La Camera, Alexis Chopin, Andre Kijkuit
  • Patent number: 8969590
    Abstract: Classes of compounds that exhibit effective inhibition of autotaxin enzymes are provided. Such classes include thioureas, diphenyldiazerenes, xanthenes, and isoindoles and exhibit reactivity with autotaxin to ultimately reduce the size of the reactive sites thereon to prevent conversion of lysophosphatidyl choline to lysophophatidic acid. Furthermore, such compounds can be incorporated within delivery forms for human ingestion. As such, these compounds accord an excellent manner of potentially reducing generation of certain cancers attributable to the presence of naturally occurring autotaxin within the human body. Methods of inactivating autotaxin to certain degrees therewith such compounds are encompassed within invention as well.
    Type: Grant
    Filed: September 18, 2012
    Date of Patent: March 3, 2015
    Inventors: Abby Louise Parrill-Baker, Daniel Lee Baker
  • Patent number: 8895963
    Abstract: An organic semiconductor material is represented by the following formula (F): wherein A represents a cyclic conjugated skeleton structure formed of one or more aromatic rings, and R1 and R2 each independently represent a substituted or unsubstituted alkyl group. The organic semiconductor material has high electron mobility and high on/off ratio, and can form an organic semiconductor thin film by a solution process making use of its solution.
    Type: Grant
    Filed: May 11, 2010
    Date of Patent: November 25, 2014
    Assignees: Dainichiseika Color & Chemicals Mfg. Co., Ltd.
    Inventors: Ken-ichi Nakayama, Junji Kido, Yong-Jin Pu, Yohei Hashimoto, Naomi Oguma, Naoki Hirata
  • Patent number: 8785690
    Abstract: A thioamide compound represented by the following general formula (1): wherein, in the general formula (1), R1 represents one of —OR11 and —NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure.
    Type: Grant
    Filed: August 20, 2013
    Date of Patent: July 22, 2014
    Assignee: Microbial Chemistry Research Foundation
    Inventors: Masakatsu Shibasaki, Naoya Kumagai
  • Publication number: 20130338313
    Abstract: The invention is based on the discovery that a remarkable improvement in the performance of maleimide thermosets can be achieved by incorporating amide-extended maleimides into an adhesive formulation. Amide-extended maleimides described herein can be used to toughen bismaleimide thermosetting materials without sacrificing any thermal stability. Amide-extended maleimides are readily prepared by reacting a bismaleimide with an appropriate amine via the well-known Michael addition reaction. Acylation of the resulting secondary amines provides the amide-extended maleimide. The acylating agent can also be used to introduce polymerizable functional groups into the backbones of these thermoset monomers. Amide-extended acrylate and methacrylate monomers can also be prepared.
    Type: Application
    Filed: August 19, 2013
    Publication date: December 19, 2013
    Applicant: Designer Molecules, Inc.
    Inventors: Stephen M. Dershem, Farhad G. Mizori
  • Patent number: 8513375
    Abstract: The invention is directed to maleimide thermosets incorporating imide-extended mono-, bis-, or polymaleimide compounds. These imide-extended maleimide compounds are prepared by the condensation of appropriate anhydrides with appropriate diamines to give amine terminated compounds. These compounds are then condensed with excess maleic anhydride to yield imide-extended maleimide compounds.
    Type: Grant
    Filed: February 4, 2011
    Date of Patent: August 20, 2013
    Inventors: Farhad G Mizori, Stephen M Dershem
  • Publication number: 20130199724
    Abstract: The invention provides epoxy and oxetane compositions including the novel acyloxy and N-acyl curing agents described herein. Use of invention curing agents result in cured adhesive compositions with remarkably increased adhesion and reduced hydrophilicity when compared to resins cured with other types of curing agents. Furthermore, the curatives of this invention do not interfere with free-radical cure and are thus suited for use in hybrid cure thermoset compositions.
    Type: Application
    Filed: March 15, 2013
    Publication date: August 8, 2013
    Applicant: Designer Molecules, Inc.
    Inventor: Designer Molecules, Inc.
  • Patent number: 8497296
    Abstract: The invention is directed to a compound of Formula (I), wherein R is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; R1 is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; X is selected from the group consisting of hydrogen atom or halogen atom; and Y is selected from the group consisting of hydrogen atom, halogen atom, C1-C4 alkyl group, nitro group, and —OCF3 group, as well as for its use in therapy, preferably for the treatment of cancer, and to a related pharmaceutical composition, the use of the compound for the manufacture of a medicament for the respective medical indication, and a method of synthesis of the compounds of the invention.
    Type: Grant
    Filed: March 16, 2012
    Date of Patent: July 30, 2013
    Assignee: King Saud University
    Inventors: Tarek Aboul-Fadl Mohamed Hassan, Adnan Ahmed Kadi, Hatem Abdel-Khader Abdel-Aziz
  • Patent number: 8404795
    Abstract: Polymers for photoresists and monomers for incorporation into those polymers are disclosed. The polymers comprise a photoacid generator (PAG) component and at least a second component that is photolytically stable and acid-stable. The polymers may also contain a third, acid-labile component. The photoacid generator is based on N-sulfoxyimides and related moieties that contain photolabile oxygen-heteroatom and oxygen-aromatic carbon bonds.
    Type: Grant
    Filed: August 26, 2010
    Date of Patent: March 26, 2013
    Assignee: The Research Foundation for the State University of New York
    Inventor: Robert L. Brainard
  • Publication number: 20120252860
    Abstract: The invention is directed to a compound of Formula (I), wherein R is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; R1 is selected from the group consisting of hydrogen atom and unsubstituted or substituted phenyl group; X is selected from the group consisting of hydrogen atom or halogen atom; and Y is selected from the group consisting of hydrogen atom, halogen atom, C1-C4 alkyl group, nitro group, and —OCF3 group, as well as for its use in therapy, preferably for the treatment of cancer, and to a related pharmaceutical composition, the use of the compound for the manufacture of a medicament for the respective medical indication, and a method of synthesis of the compounds of the invention.
    Type: Application
    Filed: March 16, 2012
    Publication date: October 4, 2012
    Applicant: King Saud University
    Inventors: Tarek Aboul-Fadl Mohamed Hassan, Adnan Ahmed Kadi, Hatem Abdel-Khader Abdel-Aziz
  • Publication number: 20120056166
    Abstract: An organic semiconductor material is represented by the following formula (F): wherein A represents a cyclic conjugated skeleton structure formed of one or more aromatic rings, and R1 and R2 each independently represent a substituted or unsubstituted alkyl group. The organic semiconductor material has high electron mobility and high on/off ratio, and can form an organic semiconductor thin film by a solution process making use of its solution.
    Type: Application
    Filed: May 11, 2010
    Publication date: March 8, 2012
    Applicants: Dainichiseika Color & Chemicals Mfg. Co., Ltd.
    Inventors: Ken-ichi Nakayama, Junji Kido, Yong-Jin Pu, Yohei Hashimoto, Naomi Oguma, Naoki Hirata
  • Publication number: 20110130538
    Abstract: Polymers for photoresists and monomers for incorporation into those polymers are disclosed. The polymers comprise a photoacid generator (PAG) component and at least a second component that is photolytically stable and acid-stable. The polymers may also contain a third, acid-labile component. The photoacid generator is based on N-sulfoxyimides and related moieties that contain photolabile oxygen-heteroatom and oxygen-aromatic carbon bonds.
    Type: Application
    Filed: August 26, 2010
    Publication date: June 2, 2011
    Applicant: The Research Foundation of the State University of New York
    Inventor: Robert L. BRAINARD
  • Publication number: 20110003955
    Abstract: To provide an imide oligomer, excellent in thermal moldability, having excellent heat resistance as a thermally-cured polyimide resin, and that is obtainable easily and inexpensively. An imide oligomer including a nonaxisymmetric site derived from one nonaxisymmetric aromatic diamine molecule represented by below formula (1), only at a central portion of the oligomer chain, in the formula (1), W is a direct bond, —O—, —CH2—, —C2H4—, —C(CH3)2—, —CF2—, —C2F4—, —C(CF3)2—, —C(?O)—, —NH—, —NH—C(?O)—, —S—, —S(?O)—, or —S(?O)2—.
    Type: Application
    Filed: July 28, 2008
    Publication date: January 6, 2011
    Applicant: DAIWA CAN COMPANY
    Inventors: Hideo Nishino, Yasuyo Watanabe, Yoichiro Inoue
  • Publication number: 20080277622
    Abstract: The invention relates to compounds of the structure of formula I and II: where X is selected from the group consisting of O, S and NH; Y, A and B are independently selected from the group consisting of N and CH; D, E and F are independently selected from the group consisting of CH, N, O and S; the symbol — represents a single or a double bond; and R1, R2 and R3 are independently selected from the group consisting of H, electron withdrawing groups and electron releasing groups. In other embodiments, the compounds are used as oxygen scavengers and in barrier compositions and articles.
    Type: Application
    Filed: May 9, 2008
    Publication date: November 13, 2008
    Inventors: Girish Nilkanth Deshpande, Paul David Weipert, Michael W. Ensley
  • Patent number: 7408070
    Abstract: A method for purifying bisimides is provided. In one aspect, purified oxybisphthalimides, intermediates useful in the preparation of polyetherimides are provided. In one embodiment, a first solution containing a bisimide 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 bisimide compound is then separated from the solid inorganic adsorbent material to provide a purified bisimide compound which is substantially free of the phase transfer catalyst. The purification technique is especially valuable for preparing high purity oxybisphthalimides, such as 4,4?-oxybis(N-methylphthalimide), which are substantially free of residual phase transfer catalyst.
    Type: Grant
    Filed: November 22, 2006
    Date of Patent: August 5, 2008
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Albert Santo Stella, David Bruce Hall
  • Patent number: 7208566
    Abstract: The invention is based on the discovery that a remarkable improvement in the performance of maleimide thermosets can be achieved through the incorporation of imide-extended mono-, bis-, or polymaleimide compounds. These imide-extended maleimide compounds are readily prepared by the condensation of appropriate anhydrides with appropriate diamines to give amine terminated compounds. These compounds are then condensed with excess maleic anhydride to yield imide-extended maleimide compounds.
    Type: Grant
    Filed: April 30, 2004
    Date of Patent: April 24, 2007
    Assignee: Designer Molecules, Inc.
    Inventors: Farhad G. Mizori, Stephen M. Dershem
  • Patent number: 7173140
    Abstract: A process composed of: reacting a reaction mixture comprised of one or more optionally substituted indolocarbazoles, a reaction medium, and a coupling agent at a reaction temperature to form a compound composed of a plurality of optionally substituted indolocarbazole moieties which are the same or different from each other.
    Type: Grant
    Filed: December 14, 2004
    Date of Patent: February 6, 2007
    Assignee: Xerox Corporation
    Inventors: Yuning Li, Yiliang Wu, Beng S. Ong
  • Patent number: 7157587
    Abstract: The invention is based on the discovery that a remarkable improvement in the performance of bismaleimide thermosets can be achieved through the incorporation of an imide-extended liquid bismaleimide monomer. This imide-extended liquid bismaleimide monomer is readily prepared by the condensation of an appropriate dianhydride with two equivalents of an appropriate diamine to give an amine terminated compound. This compound is then condensed with an excess of maleic anhydride to yield an imide-extended liquid bismaleimide monomer.
    Type: Grant
    Filed: April 30, 2004
    Date of Patent: January 2, 2007
    Assignee: Designer Molecules, Inc.
    Inventors: Farhad G. Mizori, Stephen M. Dershem
  • 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: 6835212
    Abstract: The agent for dyeing keratin fibers contains one or more aryl and/or benzyl alcohols, one or more oxidizing enzymes, especially vanillyl oxidase, derivatives of vanillyl oxidase or galactose oxidase, and a nucleophilic compound that forms a dye for dyeing keratin fibers in the presence of the alcohols and enzymes. A method for dyeing keratin fibers with this agent is also disclosed. Two-component kits for performing the method of dyeing keratin fibers include a first compenent (A) and a second component (B) separate from the first component. The first component (A) includes the nucleophilic compound, the alcohol and optionally the oxidizing enzyme. The second component (B) includes the oxidizing enzyme when it is not included in the first component or more alcohol.
    Type: Grant
    Filed: July 18, 2002
    Date of Patent: December 28, 2004
    Assignee: Wella Aktiengesellschaft
    Inventors: David Rozzell, Guido Sauter, Hans-Juergen Braun
  • Patent number: 6433184
    Abstract: The present invention relates to polyamide-imides having head-to-tail backbone and more particularly, to polyamide-imimdes having head-to-tail ragularity to provide excellent heat and chemical resistance, physical and mechanical properties, processability, and gas permeability and selectivity.
    Type: Grant
    Filed: June 28, 2000
    Date of Patent: August 13, 2002
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Jae Heung Lee, Young-Taik Hong, Moon Young Jin, Kyoung-Su Choi, Ho-Jin Park
  • Patent number: 6218536
    Abstract: 1,2-Bis-adducts of stable hindered nitroxide compounds with substituted ethylenes are prepared by reacting two equivalents of nitroxyl compound with an ethylenically unsaturated compound such as styrene or an acrylate ester. These adducts are very effective inhibitors to prevent the premature polymerization of ethylenically unsaturated monomers when such monomers are distilled, processed or stored.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: April 17, 2001
    Assignee: Ciba Specialty Chemcials Corporation
    Inventors: Glen Thomas Cunkle, Thomas F. Thompson, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 6177570
    Abstract: Bisimides of the formula I where R1, R2, R3 and R4 have the meanings stated in the description, are prepared in a process in which the corresponding dicarboxylic anhydrides of the formulae II and III R1—CO—O—CO—R2  (II) R3—CO—O—CO—R4  (III), are reacted with an amine of the formula H2N—R—NH2 in the presence of a tertiary amine.
    Type: Grant
    Filed: September 14, 1999
    Date of Patent: January 23, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Viergutz, Stefan Koser
  • Patent number: 6114156
    Abstract: Polymer encapsulated metal oxide particles are prepared by combining a polyamide acid in a polar aprotic solvent with a metal alkoxide solution. The polymer was imidized and the metal oxide formed simultaneously in a refluxing organic solvent. The resulting polymer-metal oxide is an intimately mixed commingled blend, possessing synergistic properties of both the polymer and preceramic metal oxide. The encapsulated metal oxide particles have multiple uses including, being useful in the production of skin lubricating creams, weather resistant paints, as a filler for paper, making ultraviolet light stable filled printing ink, being extruded into fibers or ribbons, and coatings for fibers used in the production of composite structural panels.
    Type: Grant
    Filed: October 31, 1996
    Date of Patent: September 5, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Patricia R. McDaniel, Terry L. St. Clair
  • 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: 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: 6008374
    Abstract: A process for making bis(ether anhydrides) employs alkylamines having low melting temperatures thus allowing for novel intermediate process steps for preparing bis(ether anhydrides). The alkylamines have alkyl groups which contain at least three carbon atoms and have boiling temperatures in the range of 48 to 250.degree. C. at atmospheric pressure. As a result of using these amines, liquid alkylamines now can be employed in the imidization process step. The N-alkyl nitrophthalimides prepared from the recovered imidization product according to this invention can now be purified using liquid/liquid extraction or vacuum distillation. The alkyl nitrophthalimides prepared according to this invention provide for displacement reactions which now can be run at a high solids level. Likewise, the exchange reaction can be run at a higher solids level, and thus achieves an efficiency level which is higher than conventional processes.
    Type: Grant
    Filed: March 15, 1999
    Date of Patent: December 28, 1999
    Assignee: General Electric Company
    Inventors: Brent Dellacoletta, Roy Ray Odle, Thomas L. Guggenheim, Ronald A. Greenberg, James P. Barren, Joseph A. King, Sunita Singh Baghel, Deborah A. Haitko, David G. Hawron
  • Patent number: 5977379
    Abstract: The invention relates to the preparation of halogenated imides derived from hydrazine, a halogen and a dicarboxylic acid anhydride and capable of being employed as fireproofing agents for plastics.A dicarboxylic acid anhydride is halogenated with bromine, chlorine or a mixture thereof and then the product thus obtained is subsequently reacted with hydrazine. No prior purification or isolation of the intermediate halogenated anhydride is required.
    Type: Grant
    Filed: March 19, 1992
    Date of Patent: November 2, 1999
    Assignee: Atochem
    Inventors: Evelyne Bonnet, Bernard Gurtner
  • Patent number: 5977289
    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. The present invention is also directed to synthesis of this special dianhydride.
    Type: Grant
    Filed: August 18, 1998
    Date of Patent: November 2, 1999
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Sheng-Huei Hsiao
  • Patent number: 5760165
    Abstract: Monoallyloxyimides, diallyloxyimides and polyallyloxyimides of general Formula I. ##STR1## wherein: X is an integer from 1 to 4 inclusive;R.sup.1, R.sup.2, and R.sup.3 are independently selected from the group comprising hydrogen, alkyl, arylalkyl or halogen; andA is all or part of an aromatic, alicyclic or mixed aromatic/alicyclic ring system optionally substituted with one or more alkyl, alkoxy, alkylthio, aryl, heteroaryl, aryloxy, carboxy, alkylamino, dialkylamino, amino, nitro, cyano, halo or haloalkyl groups.This new class of reactive monomer can be used as co-reactants in themosetting matrix resins. The reactive monomers, either alone or with other comonomers, can give rise to cured resin matrix materials with high thermal stability. Mixed with suitable bismaleimide monomers, they can be cured into useful composites having substantially improved thermal stabilities.
    Type: Grant
    Filed: May 6, 1997
    Date of Patent: June 2, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organization (CSIRO)
    Inventors: Buu Dao, Trevor Morton
  • Patent number: 5756740
    Abstract: A process for the preparation of photographic binary sensitizing dyes, which comprise two separate, nonconjugated chromophores, one of which has the capability of adsorbing to a silver halide grain surface, the other of which is substantially non-adsorbing to silver halide. The process comprises reacting two dye compounds in a solvent in the presence of a 2-halo-1-alkylpyridinium salt and a 4-dialkylaminopyridine.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: May 26, 1998
    Assignee: Eastman Kodak Company
    Inventors: Lal Chand Vishwakarma, Chin Hsin Chen
  • Patent number: 5744615
    Abstract: Disclosed is a process for producing an ultra-white N,N'-ethylene-bis(tetrabromophthalimide) product useful as a flame retardant. Also disclosed is a flame retardant composition predominantly comprised of N,N'-ethylene-bis(tetrabromophthalimide) and having unprecedented color and high purity.
    Type: Grant
    Filed: January 19, 1996
    Date of Patent: April 28, 1998
    Assignee: Great Lakes Chemical
    Inventors: Brian Tarbit, Brian Adger, Paul Willett
  • Patent number: 5719295
    Abstract: A process for making bis(ether anhydrides) employs alkylamines having low melting temperatures thus allowing for novel intermediate process steps for preparing bis(ether anhydrides). The alkylamines have alkyl groups which contain at least three carbon atoms and have boiling temperatures in the range of 48.degree. to 250.degree. C. at atmospheric pressure. As a result of using these amines, liquid alkylamines now can be employed in the imidization process step. The N-alkyl nitrophthalimides prepared from the recovered imidization product according to this invention can now be purified using liquid/liquid extraction or vacuum distillation. The alkyl nitrophthalimides prepared according to this invention provide for displacement reactions which now can be run at a high solids level. Likewise, the exchange reaction can be run at a higher solids level, and thus achieves an efficiency level which is higher than conventional processes.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: February 17, 1998
    Assignee: General Electric Company
    Inventors: Brent Dellacoletta, Roy Ray Odle, Thomas L. Guggenheim, Ronald A. Greenberg, James P. Barren, Joseph A. King, Sunita Singh Baghel, Deborah A. Haitko, David G. Hawron
  • Patent number: 5709947
    Abstract: A method for the preparation of a diaminobisimide compound of the formula (I) substantially free of oligomers: ##STR1## wherein Ar.sup.1 is an optionally substituted aromatic residue which provides for good conjugation between the nitrogen containing groups; andAr is an optionally substituted aromatic residue characterized in that at least two molar proportions of an aromatic diamine of the formula (II)H.sub.2 N--Ar.sup.1 --NH.sub.2 (II)wherein Ar.sup.1 is as defined above,are heated with one molar proportion of an aromatic tetracarboxylic acid of the formula (III) or the corresponding dianhydride,(HOOC).sub.2 Ar(COOH).sub.2 (III)wherein Ar is as defined above,optionally in the presence of a polar solvent and optionally including 0.1 to 2 molar proportions of a tertiary amine.The compounds of formula (I) are useful curing agents in epoxy resin formulations.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: January 20, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
  • Patent number: 5693797
    Abstract: A process for the preparation of brominated phthalimides that involves mixing tetrabromophthalic anhydride, an organic acid, and an organic dispersing agent in water at approximately 110.degree. C. under 1 bar pressure is disclosed. An amine is added and the reaction mixture is stirred for six hours under approximately 5 bar pressure and heated at least to 120.degree. C. The reactant mass is washed in water and then methanol. The process decreases production time, increases whiteness and purity, and decreases yellowness and particle size of the resulting product.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: December 2, 1997
    Assignee: Unitex Chemical Corporation
    Inventor: James F. Day
  • Patent number: 5672662
    Abstract: Active esters of PEG acids and related polymers are provided that have a single propionic or butanoic acid moiety and no other ester linkages. These polymer acids have a half life in water of from about 10 to 25 minutes. For example, alpha-methoxy, omega-propionic acid succinimidyl ester of PEG ("methoxy-PEG-SPA") has a nearly ideal reactivity with amino groups on proteins and other biologically active substances. The half life of methoxy-PEG-SPA is about 16.5 minutes in water. The invention also provides conjugates with proteins, enzymes, polypeptides, drugs, dyes, nucleosides, oligonucleotides, lipids, phospholipids, liposomes, and surfaces of solid materials that are compatible with living organisms, tissue, or fluid.
    Type: Grant
    Filed: October 2, 1995
    Date of Patent: September 30, 1997
    Assignee: Shearwater Polymers, Inc.
    Inventors: J. Milton Harris, Antoni Kozlowski
  • Patent number: 5610317
    Abstract: Thermomechanical and thermo-oxidative stabilities in resin composites across the range of aerospace "engineering thermoplastic" resins are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities of the general formula: ##STR1## .beta.=the residue an organic radical selected from the group consisting of: ##STR2## R.sub.8 =a divalent organic radical; X=halogen;Me=methylT=allyl or methallyl.G=--CH.sub.2 --, --S--, --CO--, --SO--, --O--, --CHR.sub.3 --, or --C(R.sub.3).sub.2 --;i=1 or 2;R.sub.3 =hydrogen, lower alkyl, lower alkoxy, aryl, or aryloxy; and.THETA.=--C.tbd.N, --O--C.tbd.N, --S--C.tbd.N, or --CR.sub.3 .dbd.C(R.sub.3).sub.2.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: March 11, 1997
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowtiz, Clyde H. Sheppard
  • Patent number: 5483008
    Abstract: The present invention relates to a bifunctional polyether having groups different from each other at both ends, with a polymerization degree of 5 to 10000 and consisting of repeating units each represented by the following formula (I): ##STR1## (wherein R.sub.1, represents a hydrogen atom, halogen atom, or a lower alkyl group optionally substituted by a halogen atom, and R.sub.1 in each repeating unit may be the same or different), as well as to a process for the preparation thereof and a polymerization initiator therefor. The process of production and polymerization initiator of the present invention enable 100% introduction of a primary amino group into one of the ends of polyether.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 9, 1996
    Assignee: Research Development Corporation of Japan
    Inventors: Yasuhisa Sakurai, Teruo Okano, Masayuki Yokoyama, Kazunori Kataoka, Yukio Nagasaki, Nobuyuki Ohsako, Masao Kato
  • Patent number: 5464861
    Abstract: 2-Thioindoles (2-selenoindoles) and analogous 2-indolinethione (2-indolineselenone) and polysulfide (selenide) compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds, and methods for inhibiting protein kinase dependent disease in a mammal or treating aberrant cell growth in a mammal, using said compositions, are disclosed.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: November 7, 1995
    Assignee: Warner-Lambert
    Inventors: Ellen M. Dobrusin, Howard D. H. Showalter, William A. Denny, Brian D. Palmer, Gordon W. Rewcastle, Moana Tercel, Andrew M. Thompson
  • Patent number: 5420234
    Abstract: Bis-N-aminoimides of formula (III): ##STR1## wherein m is 0 or 1 and ##STR2## is a mono- or polycyclic aromatic radical, can be employed to produce a variety of polymers of the type produced from diamines, including polyimides having an N--N linkage; polymers can be produced having exceptionally high glass transition temperatures, but which are also soluble in organic solvents; colored polymers and electroconductive polymers and photoconductive polymers can also be produced.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: May 30, 1995
    Inventors: Allan S. Hay, Hossein Ghassemi
  • Patent number: 5374740
    Abstract: Polyimides can be obtained by reacting a dianhydride component comprising 3,4,3',4'-bisphenyltetracarboxylic dianhydride, oxydiphthalic dianhydride and in addition further aromatic dianhydrides, and a diamine component comprising diamines of the formula ##STR1## and in addition further aromatic diamines.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: December 20, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Karin Elbl-Weiser, Juergen Koch
  • Patent number: 5367083
    Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --0--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimde oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: November 22, 1994
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5359084
    Abstract: A method for preparing an aromatic ether bisimide is provided. The mixture obtained from reacting a substituted phthalimide with a metal salt of a hydroxy aromatic compound in a non-polar solvent is extracted with about 4% to about 6% by weight aqueous alkali hydroxide solution to remove the reaction's by-products and thus provide substantially pure aromatic ether bisimide. The method is particularly suitable for extracting aromatic ether bisimide by-products from a continuous process preparing aromatic ether bisimide.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: October 25, 1994
    Assignee: General Electric Company
    Inventors: Brent Dellacoletta, Roy R. Odle
  • Patent number: 5359092
    Abstract: Bis-N-aminoimides of formula (III): ##STR1## wherein m is 0 or 1 and is a mono- or polycyclic aromatic radical, can be employed to produce a variety of polymers of the type produced from diamines, including polyimides having an N--N linkage; polymers can be produced having exceptionally high glass transition temperatures, but which are also soluble in organic solvents; coloured polymers and electroconductive polymers and photoconductive polymers can also be produced.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: October 25, 1994
    Inventors: Allan S. Hay, Hossein Ghassemi
  • Patent number: 5310933
    Abstract: Polyimides useful in electronic applications are prepared by the reaction of at least one aromatic tetracarboxylic acid or functional derivative thereof with at least one diamine in benzonitrile solution. The preferred tetracarboxylic acid derivative and diamine are 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride and bis(4-aminophenyl) sulfone, respectively. A second organic liquid, such as toluene, which is miscible with and has a lower boiling point than benzonitrile and which preferably forms an azeotropic mixture with water, is preferably also present.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: May 10, 1994
    Assignee: General Electric Company
    Inventors: John H. Lupinski, Paul E. Howson
  • Patent number: 5304655
    Abstract: Compounds of the formula ##STR1## in which X is the radical ##STR2## where R.sub.1 and R.sub.2 are in each case a hydrogen atom, an alkyl-(C.sub.1 -C.sub.10) group, aryl group, alkyl(C.sub.1 -C.sub.6)-CO group or aryl-CO group, where the aryl or aryl-CO group in the case of R.sub.1 and R.sub.2 can be substituted on the aromatic ring by fluorine and/or chlorine atoms and/or alkyl(C.sub.1 -C.sub.4) groups, or R.sub.1 and R.sub.2 together are a phthaloyl radical which can be substituted on the aromatic ring by 4 chlorine atoms or 4 fluorine atoms, or where X is the radical ##STR3## which can be substituted on the aromatic ring by fluorine and/or chlorine atoms and/or alkyl(C.sub.1 -C.sub.4) groups, and processes for their preparation.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 19, 1994
    Assignee: Hoechst AG
    Inventors: Theodor Papenfuhs, Ralf Pfirmann
  • Patent number: 5288876
    Abstract: Benzophenone iminodiimides of the formula I ##STR1## in which Y denotes hydroxyl or carboxyl, R.sub.1 denotes the optionally substituted radicals alkylene, phenylene or benzylidene, R.sub.2 denotes the radicals OH, substituted or unsubstituted alkyl or NH--CO--NHR.sub.3 and R.sub.3 denotes the radicals H, alkyl, phenyl or benzyl, processes for their preparation and polymers prepared therefrom.
    Type: Grant
    Filed: July 22, 1992
    Date of Patent: February 22, 1994
    Assignee: Chemie Linz Gesellschaft G.m.b.H.
    Inventors: Gerd Greber, Heinrich Gruber, Afschin Hassanein
  • Patent number: 5274115
    Abstract: Compounds of the formula ##STR1## in which X is the radical ##STR2## where R.sub.1 and R.sub.2 are in each case a hydrogen atom, an alkyl-(C.sub.1 -C.sub.10) group, aryl group, alkyl(C.sub.1 -C.sub.6)-CO group or aryl-CO group, where the aryl or aryl-CO group in the case of R.sub.1 and R.sub.2 can be substituted on the aromatic ring by fluorine and/or chlorine atoms and/or alkyl(C.sub.1 -C.sub.4) groups, or R.sub.1 and R.sub.2 together are a phthaloyl radical which can be substituted on the aromatic ring by 4 chlorine atoms or 4 fluorine atoms, or where X is the radical ##STR3## which can be substituted on the aromatic ring by fluorine and/or chlorine atoms and/or alkyl(C.sub.1 -C.sub.4) groups, and processes for their preparation.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: December 28, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Theodor Papenfuhs, Ralf Pfirmann