Alicyclic Ring Containing Patents (Class 568/721)
  • Patent number: 10370489
    Abstract: The invention relates to aromatic polycarbonates which comprise dioxydiarylcycloalkane structural units, and which have improved optical and thermal properties. It also relates to an improved process to produce the said polycarbonates from dihydroxydiphenylcycloalkanes, and also to mixtures of these polycarbonates with polymers, with fillers, with dyes and with conventional additives.
    Type: Grant
    Filed: December 7, 2017
    Date of Patent: August 6, 2019
    Assignee: Covestro Deutschland AG
    Inventors: Karl-Heinz Köhler, Franky Bruynseels
  • Patent number: 9868817
    Abstract: The invention relates to aromatic polycarbonates which comprise dioxydiarylcycloalkane structural units, and which have improved optical and thermal properties. It also relates to an improved process to produce the said polycarbonates from dihydroxydiphenylcyloalkanes, and also to mixtures of these polycarbonates with polymers, with fillers, with dyes and with conventional additives.
    Type: Grant
    Filed: April 8, 2011
    Date of Patent: January 16, 2018
    Assignee: Covestro Deutschland AG
    Inventors: Karl-Heinz Köhler, Franky Bruynseels
  • Patent number: 9102596
    Abstract: In a method of manufacturing 4,4?-dihydroxy-m-terphenyl, a 2-cyclohexene-1-one or 3-hydroxycyclohexane-1-one, and phenol are used as materials, Step (A), Step (B), and Step (C) are implemented in this order, or Step (D) and Step (C) are implemented in this order: Step (A) to obtain a 1,1,3-trisphenol by causing the 2-cyclohexene-1-one or 3-hydroxycyclohexane-1-one and phenol to react with each other in the presence of a catalyst; Step (B) to obtain a bis(4-hydroxyphenyl)cyclohexene by causing the 1,1,3-trisphenol to undergo breakdown reaction; Step (C) to obtain a 4,4?-dihydroxy-m-terphenyl by dehydrogenating the bis(4-hydroxyphenyl)cyclohexene; Step (D) to obtain a bis(4-hydroxyphenyl)cyclohexene by causing the 2-cyclohexene-1-one or 3-hydroxycyclohexane-1-one and phenol to react with each other in the presence of a catalyst.
    Type: Grant
    Filed: May 14, 2013
    Date of Patent: August 11, 2015
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhito Ashida, Yuki Hashimoto, Tomoya Yamamoto, Xuwang Lu
  • Patent number: 8921613
    Abstract: Provided is a polynuclear poly(phenol)family represented by general formula (1). In general formula (1), R1s are each independently C1-8 alkyl group, C1-8 alkoxy group, an aromatic hydrocarbon group, or a C1-8 saturated hydrocarbon group having an aromatic hydrocarbon group; n is 0 or an integer of 1 to 3; X is a hydroxyphenyl group represented by general formula (2); and A is a tetravalent carbon atom group or a tetravalent saturated hydrocarbon group having two or more carbon atoms, with the proviso that when A is a tetravalent saturated hydrocarbon group having two or more carbon atoms, two carbon atoms in the A group are each bonded to two phenyl groups.
    Type: Grant
    Filed: December 15, 2010
    Date of Patent: December 30, 2014
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventor: Tatsuya Iwai
  • Patent number: 8846292
    Abstract: A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with good shape and a method of forming a resist pattern and novel compositions for forming a photoresist under coat film which is excellent in optical properties and etching resistance and contains substantially no sublimable substance and an under coat film formed by the composition. Radiation-sensitive composition containing a solvent and a cyclic compound having, e.g., a cyclic compound (A) having a molecular weight of 700 to 5000 which is synthesized by the condensation reaction of a compound having 2 to 59 carbon atoms and 1 to 4 formyl groups with a compound having 6 to 15 carbon atoms and 1 to 3 phenolic hydroxyl groups, and a cyclic compound for use in the radiation-sensitive composition.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: September 30, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Patent number: 8173351
    Abstract: A compound shown by the following formula (1) can be used as a material for a radiation-sensitive composition capable of forming a resist film which effectively responds to electron beams or the like, exhibits low roughness, and can form a high precision minute pattern in a stable manner.
    Type: Grant
    Filed: January 8, 2008
    Date of Patent: May 8, 2012
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
  • Patent number: 7648816
    Abstract: A positive resist composition that includes a base material component (A) that contains an acid-dissociable, dissolution-inhibiting group and exhibits increased alkali solubility under the action of acid, and an acid generator component (B) that generates acid upon exposure, wherein the base material component (A) contains a compound (A1), in which either a portion of, or all of, the hydrogen atoms of phenolic hydroxyl groups within a polyhydric phenol compound with a molecular weight of 300 to 2,500 represented by a general formula (I) shown below have been substituted with at least one group selected from the group consisting of acid-dissociable, dissolution-inhibiting groups represented by a general formula (II) shown below and acid-dissociable, dissolution-inhibiting groups represented by a general formula (III) shown below.
    Type: Grant
    Filed: February 20, 2006
    Date of Patent: January 19, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daiju Shiono, Taku Hirayama, Hideo Hada
  • Patent number: 7622613
    Abstract: The present invention relates to a thiol compound represented by formula (1): wherein R1, R2 and n have the same meanings as in the specification, method for producing the compound, and to a photosensitive composition and a black matrix resist composition using the same which have high sensitivity and excellent property of retaining a line width in fine line patterns at the time of alkaline development, that is, being excellent in development latitude.
    Type: Grant
    Filed: October 25, 2005
    Date of Patent: November 24, 2009
    Assignee: Showa Denko K.K.
    Inventors: Hirotoshi Kamata, Mina Onishi, Katsumi Murofushi
  • Patent number: 7015365
    Abstract: A process for forming a cycloalkylidene bisphenol comprises: reacting a cycloalkanone compound of formula: where [A] is a substituted or an unsubstituted aromatic group, R1–R4 independently represent a hydrogen or a C1–C12 hydrocarbyl group; and “a” and “b” are integers independently having values from 0–3; with an aromatic hydroxy compound of formula [A]-OH, where [A] is as previously described; at a mole ratio of greater than or equal to about 20, in the presence of a sulfonic acid type ion exchange resin catalyst crosslinked with greater than or equal to about 8 weight percent of divinylbenzene, and a promoter selected from the group consisting of a mercaptan compound and a resorcinol compound; to form a cycloalkylidene bisphenol of formula: where [A], R1–R4, “a” and “b” are as previously described. Moreover, any acid catalyst can be used with a resorcinol promoter.
    Type: Grant
    Filed: December 19, 2003
    Date of Patent: March 21, 2006
    Assignee: General Electric Company
    Inventors: Debjani Kapila, Ramesh Krishnamurti, Jan-Pleun Lens, Gurram Kishan, Nileshkumar Kukalyekar, Jegadeesh Thampi, Umesh Krishna Hasyagar, Vinod Kumar Rai, Ashok S. Shyadligeri, Radhakrishna Sreenivasarao Arakali, Edward J. Nesakumar, Pramod Kumbhar
  • Patent number: 6992227
    Abstract: A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst, separating the resulting phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane from the resulting reaction mixture, and removing the phenol from the phenol adduct crystals, wherein the phenol adduct crystals are dissolved in a crystallization solvent comprising an aromatic hydrocarbon solvent and water, crystallizing the crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane out of the crystallization solvent, and collecting the crystals by filtration at a temperature of 40–60° C.
    Type: Grant
    Filed: September 11, 2000
    Date of Patent: January 31, 2006
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6972344
    Abstract: A method of producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane comprising: crystallizing a phenol adduct of 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane from a solution comprising 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and phenol; washing the phenol adduct with a washing solution comprising phenol and water; decomposing by heating the washed phenol adduct in an aqueous solvent to remove phenol from the phenol adduct, thereby obtaining pure 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: December 6, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa
  • Patent number: 6906226
    Abstract: Hydroxymethyl-substituted polyfunctional phenols, expressed by the following structure: General structure (I) (wherein X represents: bivalent group (a) expressed by the following structure: General structure (II) (wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); quadrivalent group (b) expressed by the following structure: General structure (III) (wherein R5 and R6 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); or bivalent group (c) expressed by the following structure: General structure (IV) (wherein R7 and R8 each independently represent a hydrogen atom or a monofluoromethyl, difluoromethyl or trifluoromethyl group; however, R7 and R8 cannot be both hydrogen atoms); wherein n takes 2 when X is bivalent group (a), takes 4 when X is quadrivalent group (b), or takes 2 when X is bivalent group (c)).
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: June 14, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuya Matsuishi, Takayuki Ohno, Taiichi Shiomi
  • Patent number: 6875896
    Abstract: A method for producing a high purity 1,1-bis(4-hydroxyphenyl)cyclohexane represented by the general formula (II), wherein R is a hydrogen atom or alkyl group, comprising the steps of: reacting cyclohexanone and a phenol represented by the general formula (I) in the presence of an acid catalyst; wherein R is the same as defined above, neutralizing the resultant reaction mixture with an alkali; primarily crystallizing and filtering a 1,1-bis(4-hydroxyphenyl)cyclohexane produced to obtain a primary crystallization filtrate; dissolving 100 parts by weight of the primary crystallization filtrate in a mixed solvent, which comprises 5 to 10 parts by weight of water and 100 to 200 parts by weight of a lower aliphatic ketone solvent, or 200 to 400 parts by weight of a lower aliphatic alcohol solvent; filtering the resulting solution through a zeta potential filter; and secondarily crystallizing and filtering the 1,1-bis(4-hydroxyphenyl)cyclohexane from the resulting filtrate in the presence of water.
    Type: Grant
    Filed: June 29, 2004
    Date of Patent: April 5, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Tooru Nakaguchi, Kenji Ekawa
  • Patent number: 6872858
    Abstract: The invention provides a diphenol represented by the general formula (I) wherein X is a divalent cyclic hydrocarbon group selected from 1-cyclohexene-1,4-ylene group, 1,4-cyclohexylene group and p-phenylene group, R is an alkyl group of 1-4 carbon atoms, n is 0 or an integer of 1-3 when X is 1-cyclohexene-1,4-ylene group and an integer of 1-3 when X is 1,4-cyclohexylene group or p-phenylene group. The invention further provides a process for the production of the same.
    Type: Grant
    Filed: February 7, 2002
    Date of Patent: March 29, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kouji Muragaki, Tadashi Hiramine, Hiroyasu Ohno
  • Patent number: 6838584
    Abstract: The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.
    Type: Grant
    Filed: May 6, 2002
    Date of Patent: January 4, 2005
    Assignee: Merck & Co., Inc.
    Inventors: Timothy Allen Blizzard, Milton Lloyd Hammond, Jerry Dwain Morgan, Ralph Troy Mosley
  • Patent number: 6746629
    Abstract: Coloring matters and filters for plasma display panels, which can effectively screen the neon emission radiated from plasma display panels. Squarylium compounds represented by the following formula (I): [in the formula (I), R is a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an alkenyl group which may have a substituent, m is an integer of from 1 to 4, and n is an integer of from 0 to 4], and filters for plasma display panels, made by laminating layers containing these compounds with layers containing ultraviolet absorbers and, if necessary, providing additionally near infrared screening layers, antireflection layers and/or non-glare layers.
    Type: Grant
    Filed: September 4, 2001
    Date of Patent: June 8, 2004
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tetsuo Ozawa, Tetsuo Murayama
  • Patent number: 6673974
    Abstract: A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst wherein the reaction of phenol with 3,3,5-trimethylcyclohexanone is started in a slurry comprising phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane and hydrated phenol in the presence of an acid catalyst, and then the reaction is continued in the slurry.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: January 6, 2004
    Assignee: Honshu Chemical Industry Co. Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6673975
    Abstract: The invention provides a process for production of high purity 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (BPTMC) which comprises: (a) a reaction step wherein phenol is reacted with 3,3,5-trimethylcyclohexanone (TMC) in a slurry containing phenol adduct crystals of BPTMC in the presence of an acid catalyst; (b) a neutralization step wherein after the reaction, the resulting reaction mixture in the form of slurry is neutralized with an alkali while heating to convert the slurry to a solution; (c) a primary crystallization and filtration step wherein the resulting solution is cooled and the resulting phenol adduct crystals of BPTMC are collected by filtration; (d) a secondary crystallization and filtration step wherein the adduct crystals obtained in the primary crystallization and filtration step are heated in a crystallization solvent to dissolve the crystals therein to prepare a solution and then the solution is cooled to crystallize BPTMC out of the solution, followed by collecting the crystals of
    Type: Grant
    Filed: March 7, 2003
    Date of Patent: January 6, 2004
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6673973
    Abstract: A process for production of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane which comprises reacting phenol with 3,3,5-trimethylcyclohexanone in the presence of an acid catalyst, adding an aqueous solution of an alkali to the resulting reaction mixture to neutralize it, removing a water phase from the thus neutralized reaction mixture, cooling the resulting oil phase to crystallize phenol adduct crystals of 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane while obtaining a primary crystallization filtrate, wherein the primary crystallization filtrate is heated to a temperature of 150-250° C. in the presence of an alkali catalyst in an inert gas atmosphere under a reduced pressure to thermally decompose 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane in the primary crystallization filtrate.
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: January 6, 2004
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuhiko Yao, Kenji Ekawa, Yoichiro Isota, Toru Nakaguchi
  • Patent number: 6451879
    Abstract: A process for producing a phenolic resin of good hue, characterized by reacting a hydroxylated aromatic compound with an unsaturated cyclic hydrocarbon compound in the presence of both active hydrogen and a reducing metal compound with the aid of an acid catalyst, subsequently deactivating the catalyst, and then removing the catalyst, the metal compound, and the starting materials remaining unreacted; and a process for producing an epoxy resin which comprises a step of reacting the phenolic resin with an epihalohydrin. By these processes, a phenolic resin and an epoxy resin are obtained which each is colored little and has an excellent hue. These resins are useful as resins for electrically insulating materials, especially as resins for semiconductor encapsulation materials and for laminated plates.
    Type: Grant
    Filed: April 13, 2001
    Date of Patent: September 17, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Satoshi Mori, Fumiaki Oshimi, Ryuichi Ueno
  • Patent number: 6407150
    Abstract: A process for producing phenol resin having good color tone, which process comprises reacting hydroxyl group-containing aromatic compound and unsaturated cyclic hydrocarbon under the condition that the moisture is 100 ppm or less and the concentration of Friedel-Crafts catalyst is 0.07 mass % or less in a reaction system and a process for producing epoxy resin having good color tone, which process comprises reacting the obtained phenol resin and epihalohydrin in the presence of base catalyst, removing remaining catalyst and further removing unreacted epihalohydrin.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: June 18, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Satoshi Mori, Fumiaki Oshimi, Masato Hattori
  • Patent number: 6313355
    Abstract: Tetrabromobisphenol-A is produced in a bromination process where no bromine or only a very small proportion of bromine is fed to the reactor. In the process aqueous hydrobromic acid, is the sole source or a major source of the bromine. In the process there are at least three concurrent continuous feeds to the reactor. One is composed of bisphenol-A and/or underbrominated bisphenol-A and a water-miscible organic solvent. The second is gaseous hydrogen bromide or preferably, aqueous hydrobromic acid, and the third is aqueous hydrogen peroxide. Optionally a small additional continuous feed of bromine can be employed. The feeds are proportioned to maintain a liquid phase containing (i) from above about 15 to about 85 wt % water, based upon the amount of water and water-miscible organic solvent in such liquid phase, and (ii) an amount of unreacted bromine that is in excess over the stoichiometric amount theoretically required to convert the bisphenol-A and/or underbrominated bisphenol-A to tetrabromobisphenol-A.
    Type: Grant
    Filed: July 12, 2000
    Date of Patent: November 6, 2001
    Inventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
  • Patent number: 6300527
    Abstract: This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br2 during the feed of bisphenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.
    Type: Grant
    Filed: July 12, 2000
    Date of Patent: October 9, 2001
    Assignee: Albemarle Corporation
    Inventors: Thanikavelu Manimaran, Hassan Y. Elnagar, Richard A. Holub, Alvin E. Harkins, Jr., Bonnie G. McKinnie
  • Patent number: 6284931
    Abstract: A process for producing a 3,3,5-trimethylcyclohexylidenebisphenol, comprising pre-reacting a phenol (A), i.e., phenol whose 2- and 6-positions may be monosubstituted or disubstituted with an alkyl group having 1 to 4 carbon atoms, with 3,3,5-trimethylcyclohexanone (B) at a molar ratio ((A)/(B)) of 3 to 7 in the presence of an acid catalyst until 3,3,5-trimethylcyclohexanone (B) exhibits a degree of conversion of at least 90 mol %; adding the phenol (A) and/or an aromatic hydrocarbon (C) to the thus obtained reaction mixture; and post-reacting the resultant mixture. This process enables not only suppressing a rise of the viscosity of the reaction mixture but also obtaining the desired product at high yield. Therefore, this process is applicable to not only the productivity enhancement in batch processing but also a continuous reaction processing which has been regarded as being difficult.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: September 4, 2001
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Yoichiro Isota, Toru Nakaguchi, Hiroshi Takenaka, Kazuhiko Yao
  • Patent number: 6242641
    Abstract: The present invention relates to compounds selected from formula I wherein R1, R2, R3 and R4 are the same or different and represent hydrogen, C1, to C6-alkyl, C5 to C6-cycloalkyl, phenyl and halogen, m and n are the same or different and represent the 2, 3, 4 or 5, X, A and B represent carbon and Y1, Y2, Z1 and Z2 are the same or different and represent hydrogen, hydroxyl (OH), amino (NH2), isocyanato (NCO) or 4-hydroxyphenyl.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: June 5, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Carl Casser, Hanns-Peter Müller, Manfred Hajek
  • Patent number: 6015873
    Abstract: A polyphenol composition is provided comprising trisphenol represented by the following formula (I): ##STR1## wherein R is a methyl group, X is independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a halogen atom, and m and n are an integer of 0 to 2 which has an excellent balance between heat resistance and water resistance as a curing agent for epoxy resins.
    Type: Grant
    Filed: June 26, 1997
    Date of Patent: January 18, 2000
    Assignee: Shell Oil Company
    Inventors: Mareki Miura, Yoshinobu Ohnuma
  • Patent number: 6002050
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor.
    Type: Grant
    Filed: September 8, 1998
    Date of Patent: December 14, 1999
    Assignee: Albemarle Corporation
    Inventor: Bonnie G. McKinnie
  • Patent number: 5959159
    Abstract: A process for resolving racemic diesters of (R,S)(.+-.)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane is disclosed. The process utilizes a microbial enzyme derived from Chromobacterium viscosum to catalyze the enantioselective and regioselective hydrolysis of the (S)(-)-enantiomer of the racemic mixture to its corresponding monoester at a faster rate than the (R)(+)-enantiomer. A substantially pure (S)(-)-indane monoester is thereby formed, while the (R)(+)-indane diester remains unreacted. The (S)(-)-monoester and the (R)(+)-diester can then be hydrolyzed using conventional techniques to form optically active (R)(+)- and (S)(-)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane enantiomers for use as monomers in the synthesis of chiral polymers.
    Type: Grant
    Filed: October 24, 1997
    Date of Patent: September 28, 1999
    Assignee: Molecular OptoElectronics Corporation
    Inventors: Romas Joseph Kazlauskas, Xiaoming Zhang
  • Patent number: 5932623
    Abstract: The present invention provides a fruit polyphenol obtained by subjecting unripe fruits of Rosaceae to pressing and/or extraction and then purifying the resulting juice or extract. The present invention further provides an antioxidant, a hypotensive agent, an antimutagenic agent, an antiallergic agent and an anticariogenic agent each comprising, as an effective component, a fruit polyphenol obtained by subjecting unripe fruits of Rosaceae to pressing and/or extraction and then purifying the resulting juice or extract. The fruit polyphenol of the present invention has various physiological activities, for example, an antioxidative activity, an ACE-inhibiting activity, an antimutagenic activity, a hyalulonidase-inhibiting activity and a GTase-inhibiting activity.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: August 3, 1999
    Assignee: The Nikka Whisky Distilling Co., Ltd.,
    Inventors: Masayuki Tanabe, Tomomasa Kanda, Akio Yanagida
  • Patent number: 5851837
    Abstract: A method for making bisphenol salt as the result of the reaction between bisphenol and an alkali metal hydroxide. The method comprising steps to obtain the anhydrous alkali metal bisphenoxide salt within about a 0.2 mol % stoichiometry relationship between bisphenol and alkali metal hydroxide. A method for determining stoichiometry error of a sample comprises determining variables and applying the variables to an equation to determine stoichiometry.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: December 22, 1998
    Assignee: General Electric Company
    Inventors: Edward Brittain Stokes, Thomas Link Guggenheim, James Marshall Finan
  • Patent number: 5698600
    Abstract: The invention relates to the synthesis of bisphenols from monophenols and carbonyl compounds such as aldehydes and ketones with concentrated mineral acids such as hydrochloric acid and/or hydrogen chloride gas as acid catalysts and a mercaptan as cocatalyst, which is fixed by an ion-pair bond to a matrix insoluble in the reaction medium.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: December 16, 1997
    Assignee: Bayer AG
    Inventors: Claus Wulff, Gerhard Fennhoff, Alfred Eitel
  • Patent number: 5545444
    Abstract: The present invention is to provide new diamino compounds useful for raw materials for production of liquid crystal aligning films that have excellent aligning properties and uniform and high pretilt angles over the whole display surface of wide substrates without afterimage phenomenons.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 13, 1996
    Assignee: Chisso Corporation
    Inventors: Minoru Nakayama, Toshiya Sawai, Shizuo Murata
  • Patent number: 5493060
    Abstract: This invention provides a unique method of producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane ("BPTMC"). The disclosed method manufactures BPTMC from ketals and hemithioketals of 3,3,5-trimethylcyclohexanone ("TMC"). The reaction takes place in the presence of an acid catalyst, and optionally added co-catalysts. Additionally, applicants have disclosed a particularly useful method of manufacturing BPTMC from TMC and alcohol and/or thiol starting materials. These starting materials react to form the TMC ketal or thioketal materials. This method is particularly useful in that it allows recovery and recycling of the alcohol and/or thiol.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: February 20, 1996
    Assignee: Aristech Chemical Corporation
    Inventors: Mark R. Rubino, Jeffrey S. Salek
  • Patent number: 5430195
    Abstract: The present invention is to provide new diamino compounds useful for raw materials for production of liquid crystal aligning films that have excellent aligning properties and uniform and high pretilt angles over the whole display surface of wide substrates without afterimage phenomenons.
    Type: Grant
    Filed: October 25, 1994
    Date of Patent: July 4, 1995
    Assignee: Chisso Corporation
    Inventors: Minoru Nakayama, Toshiya Sawai, Shizuo Murata
  • Patent number: 5414126
    Abstract: The present invention is to provide new diamino compounds useful for raw materials for production of liquid crystal aligning films that have excellent aligning properties and uniform and high pretilt angles over the whole display surface of wide substrates without afterimage phenomenons.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: May 9, 1995
    Assignee: Chisso Corporation
    Inventors: Minoru Nakayama, Toshiya Sawai, Shizuo Murata
  • Patent number: 5406003
    Abstract: A phenolic compound is provided which can be described by the formula ##STR1## in which Ar is a C.sub.6-20 aromatic moiety, L is a cyclohexanenorbornane linking moiety, L' is a divalent cycloaliphatic moiety, and each of m and n is a number within the range of 0 to about 10. Such phenols include the product of the addition reaction of phenol with a cyclohexenenorbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1 ]hept-2-ene.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: April 11, 1995
    Assignee: Shell Oil Company
    Inventors: Pen C. Wang, Donald R. Kelsey
  • Patent number: 5387725
    Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: February 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
  • Patent number: 5382713
    Abstract: A phenolic compound is provided which can be described by the formula ##STR1## in which Ar is a C.sub.6-20 aromatic moiety, L is a cyclohexanenorbornane linking moiety, L' is a divalent cycloaliphatic moiety, and each of m and n is a number within the range of 0 to about 10. Such phenols include the product of the addition reaction of phenol with a cyclohexenenorbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1]hept-2-ene.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 17, 1995
    Assignee: Shell Oil Company
    Inventors: Pen C. Wang, Donald R. Kelsey
  • Patent number: 5349111
    Abstract: A novolac resin is prepared by reacting a phenolic compound, an aldehyde or a ketone, and a hydroxyl-substituted benzocyclobutene compound wherein the hydroxyl group is attached to an aromatic ring. The benzocyclobutenes are connected to the phenolic rings through an oxygen or oxyaryl bridge, or the cyclobutene is fused directly to a phenol ring. The novolac resin cures without evolution of volatiles and, when cured, provides a polymer which has a high glass transition temperature and which is essentially insoluble in organic solvents.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: September 20, 1994
    Assignee: The Dow Chemical Company
    Inventor: Daniel M. Scheck
  • Patent number: 5345001
    Abstract: An aqueous resol solution produced by an alkaline condensation of a phenolic compound with an aldehyde in a molar ratio of 1:1.5 to 2.5 with an alkali metal content of 1 to 5.0% by weight of the reaction solution, neutralizing the solution after the end of condensation at least partially with an aromatic hydroxy carboxylic acid at a temperature not greater than 50.degree. C. and then concentrating the reaction mixture which is readily dilutable with water.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: September 6, 1994
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Stephan Schroter, Achim Hansen, Arno Gardziella, Peter Adolphs
  • Patent number: 5344999
    Abstract: 1,3-Bis(4-hydroxyphenyl)-1,3-dialkylcyclohexanes, as illustrated by 1,3-bis(4-hydroxyphenyl)-1, 3-dimethylcyclohexane, may be prepared by the reaction of phenol with a 1,5-dialkyl-1,4-cyclohexadiene under acidic conditions. Polycarbonates prepared therefrom have high glass transition temperatures and are expected to be ductile.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: September 6, 1994
    Assignee: General Electric Company
    Inventor: John C. Schmidhauser
  • Patent number: 5336752
    Abstract: A method is provided for producing a phenolic resin represented by the formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.2 is a divalent cyclic hydrocarbon residue having 5 to 18 carbon atoms, p is a number of from 0 to 10 and q is a number of 1 or 2. The method involves reacting a phenol with an unsaturated cyclic hydrocarbon compound having two or more carbon-carbon double bonding in the presence of an acid catalyst; and processing a resulting reaction product by a hydrotalcite compound represented by the formula (II)M.sub.1-x.sup.2+ M.sub.x.sup.3+ (OH).sub.2+x-ny A.sub.y.sup.n-.m(H.sub.2 O)(II)where M.sup.2+ is a divalent, magnesium ion, a divalent zinc ion, a divalent calcium ion, a divalent nickel ion, a divalent cobalt ion, a divalent manganese ion or a divalent copper ion, M.sup.3+ is a trivalent aluminum ion, a trivalent iron ion or a trivalent chromium ion, A.sup.n- is HCO.sub.3.sup.-, CO.sub.3.sup.2- or OH.sup.-, and x, y and m each are 0.
    Type: Grant
    Filed: January 28, 1993
    Date of Patent: August 9, 1994
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Fumiaki Oshimi, Susumu Kubota, Masami Enomoto, Yutaka Otsuki
  • Patent number: 5336812
    Abstract: A process for making 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane via the acid catalyzed reaction of phenol and 3,3,5-trimethylcyclohexanone containing an organic thiol co-catalyst is described wherein the organic thiol is rejuvenated by treatment with a halogen acid and recycled to a fresh mixture of phenol and 3,3,5-trimethylcyclohexanone to make additional 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: August 9, 1994
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach, Mark R. Rubino
  • Patent number: 5283374
    Abstract: A radiation-sensitive composition comprising an admixture in a solvent of: at least one alkali-soluble binder resin, at least one photoactive compound and an effective sensitivity enhancing amount of at least one compound of formula (I): ##STR1## wherein each R is individually selected from the group consisting of hydrogen and a lower alkyl group having 1-4 carbon atoms and each n is 0, 1, or 2; the amount of said binder resin being about 60 to 95% by weight, the amount of said photoactive component being about 5% to about 40% by weight, based on the total solids content of said radiation-sensitive composition.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: February 1, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Alfred T. Jeffries, III
  • Patent number: 5281688
    Abstract: 1,3-Bis(4-hydroxyphenyl)-1,3-dialkylcyclohexanes, as illustrated by 1,3-bis(4-hydroxyphenyl)-1,3-dimethylcyclohexane, may be prepared by the reaction of phenol with a 1,5-dialkyl-1,4-cyclohexadiene under acidic conditions. Polycarbonates prepared therefrom have high glass transition temperatures and are expected to be ductile.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: January 25, 1994
    Assignee: General Electric Company
    Inventor: John C. Schmidhauser
  • Patent number: 5276213
    Abstract: Dihydroxydiphenyl bicycloalkanes characterized in that they contain 9 to 13 ring C atoms in the bicycloaliphatic component are disclosed. The disclosed compounds were found to be suitable for the preparation of high molecular weight, thermoplastic polycarbonate resins having favorable properties.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: January 4, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Volker Serini, Uwe Westeppe, Gerd Fengler, Manfred Hajek, Carl Casser, Helmut Waldmann
  • Patent number: 5210328
    Abstract: This invention relates to a process for the preparation of substituted cycloalkylidene bisphenols from phenols and special cycloalkanones in the presence of acid condensation catalysts and in the presence of water.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: May 11, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Freitag, Claus H. Wulff, Alfred Eitel, Helmut Waldmann, Uwe Westeppe, Manfred Hajek, Klaus D. Berg, Bernd Griehsel, Carl Casser
  • Patent number: 5157164
    Abstract: This invention is addressed to antioxidants which are polymerizable using the Ziegler catalyst system. The antioxidant of the present invention has the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each aryl groups containing a hindered antioxidant structure imparting antioxidant properties to the compounds. The compounds of the present invention are useful in the polymerization of olefin compounds using Ziegler catalyst systems whereby the antioxidant of the invention becomes chemically bound to the polymer while, at the same time, imparting antioxidant properties thereto.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: October 20, 1992
    Assignee: Copolymer Rubber & Chemical Corp.
    Inventor: Errol J. Olivier
  • Patent number: 5110993
    Abstract: 9,9-Bis(3,5-diphenyl-4-hydroxyphenyl)fluorene a novel compound can be used to produce amorphous poly(arylene ethers) which have high glass transition temperatures and good thermo-oxidative stability and which are soluble in aromatic and chlorinated solvents; the novel fluorene derivative is produced by transalkylation of 9,9-bis(4-hydroxyphenyl)fluorene or 9,9-bis(4-methoxyphenyl)fluorene with 2,6-diphenylphenol.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: May 5, 1992
    Inventors: Allan S. Hay, Zhi Y. Wang
  • Patent number: 5017727
    Abstract: This invention is addressed to antioxidants which are polymerizable using the Ziegler catalyst system. The antioxidant of the present invention has the formula: ##STR1## wherein R.sub.1 and R.sub.2 are each aryl groups containing a hindered antioxidant structure imparting antioxidant properties to the compounds. The compounds of the present invention are useful in the polymerization of olefin compounds using Ziegler catalyst systems whereby the antioxidant of the invention becomes chemically bound to the polymer while, at the same time, imparting antioxidant properties thereto.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: May 21, 1991
    Assignee: Copolymer Rubber & Chemical Corporation
    Inventor: Errol J. Olivier