Phenolic Reactant Contains A Fused-or Bridged-ring Other Than As A 1,2 Epoxy Group Fused To Carbocyclic Or Aromatic Ring Patents (Class 528/97)
  • Patent number: 5418266
    Abstract: An epoxy resin composition comprising (A) a naphthalene ring-containing epoxy resin, (B) a specific phenolic resin preferably in admixture with a conventional phenolic resin, especially naphthalene ring-containing phenolic resin, and (C) an inorganic filler shows good flow and cures to products having low modulus of elasticity, a low coefficient of expansion, high Tg irrespective of low stresses, and minimized water absorption. Then semiconductor devices encapsulated with the present composition remain highly reliable even after being subject to thermal shocks upon surface mounting.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: May 23, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Shiobara, Takayuki Aoki, Kazutoshi Tomiyoshi
  • Patent number: 5414125
    Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5412057
    Abstract: Anhydride compounds which contain at least one rodlike mesogenic moiety and at least two anhydride groups per molecule, wherein each of said aromatic anhydride groups is linked to the mesogen via an ester linkage are prepared. These anhydride compounds are useful in curing epoxy resins to provide the cured products with one or more improved properties.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: May 2, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5412002
    Abstract: An epoxy resin composition contains an epoxy resin represented by the formula (I) and a curing accelerator: ##STR1## wherein R.sup.1 stands for ##STR2## where G stands for a glycidyl group, R.sup.2 stands for an alkyl group having 1 to 4 carbon atoms, R.sup.3 and R.sup.4 stand for the same or different groups and each denote a hydrogen atom or a glycidyl group, m and x each denote an integer of 0 to 10, n denotes an integer of 0 to 2, provided that m.gtoreq.x and, if m=0, then x=0, in which case at least one of R.sup.3 and R.sup.4 denotes a glycidyl group on the condition that when m.gtoreq.1 and m>x, R.sup.1 may each stand for different groups.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: May 2, 1995
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Masami Enomoto, Susumu Kubota, Hitoshi Yuasa, Fumiaki Oshimi, Yutaka Otsuki
  • Patent number: 5412044
    Abstract: Adducts containing terminating nitro (nitroso) groups and one or more mesogenic moieties are prepared by reacting (A) at least one compound containing an average of more than one vicinal epoxide group per molecule with (B) at least one compound containing one or more nitro (nitroso) groups and an average of one reactive hydrogen atom per molecule; with the proviso that at least one member of components (A) and (B) contains a mesogenic moiety. Reduction of these adducts provides amines which are useful as curing agents for epoxy resins.
    Type: Grant
    Filed: May 12, 1994
    Date of Patent: May 2, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5391651
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: February 21, 1995
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5391650
    Abstract: A compound having at least one 2-hydroxy-1,3-propylidene, 2-acetoxy-1,3-propylidene, or 2-alkoxy-1,3-propylidene moiety between two benzocyclobutene end moieties is prepared by (a) contacting a diepoxide species with a benzocyclobutene species containing a functionality capable of reacting with an epoxy group, (b) contacting an epoxy-containing benzocyclobutene species with a species containing two functionalities capable of reacting with an epoxy group, (c) contacting an epoxy-containing benzocyclobutene species with a benzocyclobutene species containing a functionality capable of reacting with an epoxy group, (d) contacting epichlorohydrin with benzocyclobutene species capable of reacting with an epoxy group, or (e) contacting epihalohydrin with benzocyclobutene species and difunctional species, wherein both species contain functionalities capable of reacting with epoxy groups.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: February 21, 1995
    Assignee: The Dow Chemical Company
    Inventors: David J. Brennan, Jerry E. White, Daniel M. Scheck, Robert A. Kirchhoff, Charles Z. Hotz
  • Patent number: 5385990
    Abstract: A structural adhesive composition containing an epoxy compound, an amine hardener and a hydroxy-substituted aromatic compound having a pKa ranging from about 5 to 9.7 and a boiling point greater than about 210.degree. C. The utilization of a hydroxy-substituted aromatic compound having a pKa and a boiling point within the stated ranges provides for an adhesive composition which develops significant green strength, undergoes minimal sinkage during the bonding and curing process, and is capable of withstanding high temperature conditions.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: January 31, 1995
    Assignee: Lord Corporation
    Inventors: Kirk J. Abbey, Stephen E. Howe, Beth C. Munoz
  • Patent number: 5369192
    Abstract: The invention relates to a resin transfer molding preform binder resin that comprises at least one aromatic polyepoxide, a fluorene epoxide that is different than the aromatic polyepoxide and having a defined structure, and a 9,9-bis(aminophenyl)fluorene curing agent. The binder resin is a solid, room temperature stable, essentially nonsintering powder that displays a glass transition temperature greater than about 40.degree. C. Also disclosed are preforms made with the binder resin and a method for preparing the preforms.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: November 29, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Chan U. Ko, Steven C. Hackett
  • Patent number: 5364912
    Abstract: Thermoplastic resins are prepared by reacting polyglycidyl esters containing one or more mesogenic moieties with compounds having an average of more than one active hydrogen atom per molecule. These resins exhibit ordering of the molecular chains in the melt phase and are susceptible to orientation during processing which can result in enhanced unidirectional mechanical properties. These resins are useful in coatings, laminates, castings and the like.
    Type: Grant
    Filed: August 16, 1993
    Date of Patent: November 15, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5360887
    Abstract: A flame-retarded thermosetting resin composition is provided by blending about 5 to 45 mole % of a phenylcyanate having at least one halogen substituent at the ortho or para position relative to the cyanato group, and about 55 to 95 mole % of a halogen-free bis-4-phenylcyanate. A flame retardancy of V-O grade of UL94 is achieved in the thermoset resin of the composition without compromising dielectric, heat resistance, moisture absorption and other properties.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: November 1, 1994
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hidenari Tsunemi, Toshinobu Nakata, Koyoyuki Namura
  • Patent number: 5360886
    Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorous atom per molecule.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: November 1, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5360870
    Abstract: A novel hydroxyphenylated resin having excellent thermal stability, weather resistance, and electrical properties useful as a resin for a printed circuit board, a resin for sealing a semiconductor, an insulating materials, and the like; a process for preparing the resin; and curable epoxy composition comprising the same. Specifically, the present invention provides a novel resin containing a number of phenolic hydroxyl groups and having a high softening point and substantially no double bonds; and a process for preparing the same wherein a butadiene oligomer and a phenol compound are used as starting materials; and a curable epoxy resin composition comprising the same suitable for applications such as a sealing material.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: November 1, 1994
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Masami Enomoto, Hitoshi Yuasa, Fumiaki Oshimi, Yutaka Otsuki
  • Patent number: 5359023
    Abstract: An epoxy resin is provided which can be described by the formula ##STR1## in which Ar is an aromatic moiety, L is a divalent cyclohexanen or bornane linking moiety, L' is a divalent cycloaliphatic moiety, Gly is a glycidyl ether group, and each of m and n is a number within the range of 0 to about 10. Such epoxy resins include the product of glycidation of the product of the addition reaction of a phenol and a cyclohexenenorbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1]hept-2-ene. The resulting epoxy resins have low melt viscosity and low water absorbance in the cured state and are useful as the resinous component of high-performance electrical laminating and encapsulation formulations.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: October 25, 1994
    Assignee: Shell Oil Company
    Inventors: Pen-Chung Wang, Donald R. Kelsey
  • Patent number: 5356566
    Abstract: Disclosed are a polyester compound having a repeating unit represented by the formula--OC--A--COO--BO-- (1)wherein A is a 1,3:2,4-dibenzylidenesorbitol or 1,3:2,4-dibenzylidenexylitol residue of the formula ##STR1## wherein t is 1 or 0, and B is a residue formed by removal of two hydroxyl groups from a polyhydric alcohol, and an organic gelling agent comprising the polyester compound.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: October 18, 1994
    Assignee: New Japan Chemical Co., Ltd.
    Inventors: Toshiaki Kobayashi, Sachio Kitagawa
  • Patent number: 5352762
    Abstract: A multilayer printed circuit board comprising a plurality of alternately laminated layers of insulating layers and circuit conductor layers having a signal transmission delay time of 6.0 ns/m or less, excellent in heat resistance, adhesive, fire retardance, etc. can be produced by forming insulating layers using a fluorine-containing thermosetting resin composition.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: October 4, 1994
    Assignee: Hitachi, Ltd.
    Inventors: Akira Nagai, Shin Nishimura, Masahiro Suzuki, Masao Suzuki, Junichi Katagiri, Akio Takahashi, Akio Mukoh
  • Patent number: 5348635
    Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.
    Type: Grant
    Filed: February 3, 1993
    Date of Patent: September 20, 1994
    Assignee: BASF Corporation
    Inventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
  • Patent number: 5344899
    Abstract: A phenolic resin is represented by the formula (1) ##STR1## wherein R.sup.1 denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, m denotes an integer of from 0 to 10 and n denotes 0, 1 or 2. A method for producing the phenolic resin involves reacting in the presence of an acid catalyst 3a,4,7,7a-tetrahydroindene and a phenol represented by the formula (2) ##STR2## wherein R.sup.1 denotes a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and n denotes 0, 1 or 2. An epoxy resin composition for encapsulation contains: (a) a curable epoxy resin, (b) the above phenolic resin, (c) a curing promotor, and (d) an inorganic filler.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: September 6, 1994
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Masami Enomoto, Susumu Kubota, Fumiaki Oshimi, Hitoshi Yuasa, Yutaka Otsuki
  • Patent number: 5344898
    Abstract: Adducts containing terminating nitro (nitroso) groups and one or more mesogenic moieties are prepared by reacting (A) at least one compound containing an average of more than one vicinal epoxide group per molecule with (B) at least one compound containing one or more nitro (nitroso) groups and an average of one reactive hydrogen atom per molecule; with the proviso that at least one member of components (A) and (B) contains a mesogenic moiety. Reduction of these adducts provides amines which are useful as curing agents for epoxy resins. Curable compositions comprising an epoxy resin and the adducts can be oriented before, during or prior to curing.
    Type: Grant
    Filed: November 18, 1993
    Date of Patent: September 6, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5342904
    Abstract: Polymer modified adducts are prepared by (A) reacting (1) an epoxy resin having an average of more than one vicinal epoxide group with (2) a compound containing an average of two or more hydrogen atoms reactive with an epoxide group; and (B) partially vinylizing reacting the product from step (A); and (C) polymerizing the partially vinylized product from step (B) with (3) a polymerizable ethylenically unsaturated monomer; with the proviso that at least one of the components (1), (2) or (3) contain one or more mesogenic or rodlike moieties. These adducts are useful as epoxy resin curing agents.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: August 30, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5342902
    Abstract: The present invention relates to poly(ester-ether) compositions and to a process for their preparation. In particular, the invention relates to poly(ester-ether) compositions obtained by reacting a polyester which is prepared from a dicarboxylic acid and an aliphatic diol with a dihydroxy aromatic compound in the presence of a metal catalyst. Incorporation of the dihydroxy aromatic compound into the polyester chain causes an increase in the Tg value and increases the thermal stability of the polyester. These poly(ester-ether) compositions are useful in molded articles of all types.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: August 30, 1994
    Assignee: Eastman Chemical Company
    Inventors: W. Ronald Darnell, W. J. Jackson, Jr.
  • Patent number: 5340851
    Abstract: A thermosetting resin composition contains (A) a mixture of an imide compound having an allyl-free maleimide group and an imide compound having an allyl-containing imide group, (B) an epoxy resin, (C) a phenolic resin, and optionally, (D) an aromatic polymer/organo-polysiloxane copolymer. Component (B) and/or (C) includes a compound containing a naphthalene ring having a double bond conjugated with an aromatic ring. The composition is easily workable and well adhesive and cures to products having improved mechanical strength, hot-water resistance, low thermal expansion, and minimized water absorption.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: August 23, 1994
    Assignee: Shin-Etsu Chemical Company, Ltd.
    Inventors: Toshio Shiobara, Hisashi Shimizu, Minoru Takei
  • Patent number: 5334674
    Abstract: Copolycondensation of a hydroxyl group-containing naphthalene and xylene with an aldehyde compound gives a polyhydroxy aromatic compound. The hydroxyl group-containing naphthalene comprises at least one of naphthols and dihydroxynaphthalenes. In the polyhydroxy aromatic compound, the proportions of the naphthalene unit and xylene unit are 95 to 50:5 to 50 (mole percent), and each molecule contains 2 to 20 naphthalene units. The polyhydroxy aromatic compound is useful as an epoxy resin curing agent. Reaction of the polyhydroxy aromatic compound with an epihalohydrin gives an epoxy resin. An epoxy resin composition can be prepared from the epoxy resin and a curing agent.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: August 2, 1994
    Assignees: Dai-Ichi Kogyo Seiyaku Co., Ltd., Nitto Denko Corporation
    Inventors: Akihiro Naka, Shuichi Ito, Shinya Akizuki, Kiyoshi Saito
  • Patent number: 5310853
    Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorous atom per molecule.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: May 10, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5306748
    Abstract: Fluorine-modified thermosetting reins are available as phenolic or epoxy resins having trifluoromethyl groups and a naphthalene skeleton in a molecule. They are useful as components of resin compositions or resin modifiers and cure to products having low water pickup, low coefficient of thermal expansion, and adhesion as well as heat resistance and mechanical strength. Thermosetting resin compositions having such a thermosetting resin blended therein are useful in semiconductor element packaging.
    Type: Grant
    Filed: July 29, 1992
    Date of Patent: April 26, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Shiobara, Hisashi Shimizu, Manabu Narumi
  • Patent number: 5302673
    Abstract: Copolycondensation of .alpha.-naphthol and .beta.-naphthol with an aldehyde compound gives a poly-hydroxynaphthalene compound having an average molecular weight of 300 to 2,000. This compound is useful as a curing agent for epoxy resins and as a precursor of epoxy resins. Epoxy resin compositions include (1) compositions comprising an epoxy resin and the poly-hydroxynaphthalene compound as a curing agent and (2) compositions comprising an epoxy resin obtained by reacting the poly-hydroxynaphthalene compound with an epihalohydrin and a curing agent. The epoxy resin compositions of the invention are characterized in that the cured resins have a high glass transition temperature and high heat stability and high moisture resistance, scarcely allowing package cracking even in soldering treatment. Therefore the compositions are suited for use in encapsulating semiconductors.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: April 12, 1994
    Assignees: Dai-Ichi Kogyo Seiyaku Co., Ltd., Nitto Denko Corporation
    Inventors: Akihiro Naka, Shuichi Ito, Shinya Akizuki, Kiyoshi Saito
  • Patent number: 5302690
    Abstract: Polyester resins are prepared by reacting a lower alkyl ester of an aromatic dicarboxylic acid with an aliphatic diol to form an aromatic polyester, and which includes (i) subjecting to transesterification reaction conditions in the presence of a titanium compound catalyst a transesterification reaction system having the lower alkyl ester of the aromatic dicarboxylic acid, the aliphatic and between 0.02 to 5.0 mole percent, based on the amount of the lower alkyl ester of the aromatic dicarboxylic acid, of an aromatic sulfonic acid compound represented by the following general formula (I):OH--R--O--Ar--SO.sub.3 M (I)wherein Ar is a p-substituted benzene group or a 2,6-substituted naphthalene group, R is a divalent group selected from among --CH.sub.2 CH(CH.sub.3)--, --CH(CH.sub.3)CH.sub.2 --, --CH.sub.2 CH(CH.sub.3)-- and --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, and M is an alkali metal selected from the group consisting of lithium, sodium and potassium.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: April 12, 1994
    Assignee: Polyplastics Co., Ltd.
    Inventors: Kuniaki Kawaguchi, Kenji Hijikata, Toshio Nakane
  • Patent number: 5302672
    Abstract: A 1,1-bis(2,7-diglycidyloxy-1-naphthyl)alkane as an epoxy resin; a 1,1-bis(2,7-dihydroxy-1-naphthyl)alkane as an intermediate for said epoxy resin; a process for producing said intermediate comprising reacting 2,7-dihydroxy-1-naphthalene and an aldehyde; a process for producing said epoxy resin comprising reacting said intermediate and an epihalohydrin; and an epoxy resin composition comprising said epoxy resin and a curing agent. The epoxy resin has a low melt viscosity while exhibiting excellent heat resistance.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: April 12, 1994
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Ichiro Ogura, Shunji Ehara, Taku Kitamura, Hiroshi Sakata
  • Patent number: 5300594
    Abstract: bis(Aminophenoxy)-alpha-substituted stilbenes are prepared by reacting a dihydroxy-alpha-substituted stilbene with a halonitrobenzene in the presence of a basic acting substance such as potassium carbonate and hydrogenating the resulting bis(nitrophenoxy)-alpha-substituted stilbene to convert the nitro groups to amino groups. These compounds are useful as curing agents for epoxy resins.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: April 5, 1994
    Assignee: The Dow Chemical Company
    Inventors: V. Rao Durvasula, Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5298575
    Abstract: Adducts containing terminating nitro (nitroso) groups and one or more mesogenic moieties are prepared by reacting (A) at least one compound containing an average of more than one vicinal epoxide group per molecule with (B) at least one compound containing one or more nitro (nitroso) groups and an average of one reactive hydrogen atom per molecule; with the proviso that at least one member of components (A) and (B) contains a mesogenic moiety. Reduction of these adducts provides amines which are useful as curing agents for epoxy resins.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: March 29, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5298548
    Abstract: An epoxy resin composition comprising (A) a naphthalene ring-containing epoxy resin, (B) a biphenyl-containing epoxy resin, (C) a specific phenolic resin, and (D) an inorganic filler shows good flow and cures to products having low modulus of elasticity, especially at temperatures above Tg, a low coefficient of expansion, high Tg irrespective of low stresses, and minimized water absorption. Then semiconductor devices encapsulated with the present composition remain highly reliable even after being subject to thermal shocks upon surface mounting.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: March 29, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Shiobara, Takayuki Aoki, Kazutoshi Tomiyoshi, Hisashi Shimizu, Takashi Tsuchiya
  • Patent number: 5296570
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: June 1, 1993
    Date of Patent: March 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5292831
    Abstract: Phenoxy resins containing rodlike mesogenic moieties are prepared from phenolic hydroxyl containing compounds which contain such moieties.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: March 8, 1994
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5290882
    Abstract: A thermosetting resin composition contains (A) an imide compound having a maleimide group, (B) an epoxy resin, (C) a phenolic resin, and optionally, (D) an aromatic polymer/organopolysiloxane copolymer. Component (B) and/or (C) includes a compound containing a naphthalene ring having an allyl group and preferably, a compound containing a naphthalene ring and a double bond conjugated with an aromatic ring. The composition is easily workable and cures to products having improved heat resistance, low thermal expansion, and low water absorption.
    Type: Grant
    Filed: August 11, 1992
    Date of Patent: March 1, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Shiobara, Hisashi Shimizu, Manabu Narumi
  • Patent number: 5288816
    Abstract: The present invention relates to nonlinear optical materials comprising aminoaryl hydrazones and to nonlinear optical polymeric compositions containing recurring covalently bonded moieties derived from the aminoaryl hydrazones of the invention. The polymeric compositions of the present invention have high glass transition temperatures and exhibit stable nonlinear optical activity at high temperatures over a period of time.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: Muthiah N. Inbasekaran, Mark D. Newsham, Michael N. Mang
  • Patent number: 5284929
    Abstract: An epoxy resin is provided which can be described by the formula ##STR1## in which Ar is an aromatic moiety, L is a divalent cyclohexanenorbornane linking moiety, L' is a divalent cycloaliphatic moiety, Gly is a glycidyl ether group, and each of m and n is a number within the range of 0 to about 10. Such epoxy resins include the product of glycidation of the product of the addition reaction of a phenol and a cyclohexenenorbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1]hept-2-ene. The resulting epoxy resins have low melt viscosity and low water absorbance in the cured state and are useful as the resinous component of high-performance electrical laminating and encapsulation formulations.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: February 8, 1994
    Assignee: Shell Oil Company
    Inventors: Pen-Chung Wang, Donald R. Kelsey
  • Patent number: 5275853
    Abstract: Polyetheramines having improved barrier to oxygen are thermoplastic polymers having aromatic ether/amine repeating units in their backbones and pendant hydroxyl moieties. Such polyetheramines are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol-A, hydroquinone, or resorcinol with amines having no more than two amine hydrogens per molecule, such as piperazine or ethanolamine.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: January 4, 1994
    Assignee: The Dow Chemical Company
    Inventors: H. Craig Silvis, Jerry E. White
  • Patent number: 5270405
    Abstract: Advanced epoxy resins containing mesogenic moieties are prepared from epoxy resins which contain such moieties.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: December 14, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5270406
    Abstract: Advanced epoxy resin compositions are prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties. Curable compositions containing these advanced epoxy resin compositions are useful in adhesives, coatings, laminates castings and the like.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: December 14, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
  • Patent number: 5270404
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with curing agents which will normally cure epoxy resins. These curable compositions can be oriented by the application of an electric field, magnetic field drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical or mechanical properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: December 14, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5268434
    Abstract: An epoxy resin composition useful as a molded article is curable with a combination of curing agents including diamino-alpha-alkylstilbenes and other curing agents wherein the epoxy resin and/or the other curing agents can contain rodlike mesogenic moieties.
    Type: Grant
    Filed: January 5, 1993
    Date of Patent: December 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5266660
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with curing agents which will normally cure epoxy resins. These curable compositions can be oriented by the application of an electric field, magnetic field drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical or mechanical properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Co.
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5266661
    Abstract: Curable compositions are disclosed which contain (I) an advanced resin composition prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties and (II) a suitable curing agent.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
  • Patent number: 5262509
    Abstract: Phenoxy resins are disclosed which are prepared from polyglycidyl amines containing one or more mesogenic moieties. The phenoxy resins are useful in the preparation of coatings.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: November 16, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5235006
    Abstract: Novel mesogens, epoxy resins and the synthesis thereof as well as coating binders for coating compositions based upon the mesogens and epoxy resins are described.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: August 10, 1993
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian, Daozhang Wang
  • Patent number: 5227452
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: July 13, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5223602
    Abstract: This invention relates to naphthol aralkyl resins of the general formula (I) ##STR1## in which A is a naphthalene nucleus, R is hydrogen or methyl, and n is an integer from 0 to 15 and cured products thereof, which are highly heat- and moisture-resistant, possess excellent impact strength and other mechanical properties, and are useful for such applications as lamination, molding, casting, and adhesion.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 29, 1993
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Masashi Kaji, Takanori Aramaki, Norito Nakahara, Yasuharu Yamada
  • Patent number: 5218061
    Abstract: The present invention relates to a novel polyfunctional epoxy resin having two phenolic glycidyl ether groups, one or more of alcoholic glycidyl ether groups and one or more of alcoholic hydroxyl groups in one molecules. The present invention further provides an epoxy resin composition comprising the epoxy resin. The cured product obtained from the epoxy resin composition according to the present invention is excellent in heat resistance, toughness, adhesion property and water proofness, and it is extremely useful for a wide range of application uses such as molding materials, casting materials, laminate materials, coating materials, adhesives and photoresists.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: June 8, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yoshitaka Kajiwara, Shoushi Takahashi, Kenichi Mizoguchi, Sumio Saito
  • Patent number: 5218062
    Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: June 8, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5212264
    Abstract: There are disclosed substantially linear polyarylene ether sulfones having a reduced viscosity of having a reduced viscosity of ca. 0.25 to ca. 1.5 dl/g (measured in a 1% solution in DMF at 25.degree. C.) and consisting essentially of 95-99.8% by weight of segments of formula I and of 5-0.2% by weight of segments of formula IIa, formula IIb and/or formula IIc ##STR1## the percentages by weight being based on the entire polymer and the molecular weight (number average) of the segments of formula I being 6000 to ca. 60 000, if the polymer contains solely structural units of formula IIa and/or IIb, and 1000 to ca. 60 000 if the polymer contains more than 0.1% by weight of structural units of formula IIc, and R consists of the recurring structural units of formula Ia and/or of up to 99.8% by weight, based on the total polymer, of recurring structural units of formula Ib ##STR2## wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.10 alkenyl, phenyl or halogen, p is an integer from 0 to 4 Ar.sub.1 and Ar.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: May 18, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Hoffmann, Thomas Kainmuller, Rudolf Pfaendner