Three Or More Phenols Containing Patents (Class 568/720)
  • Patent number: 7659047
    Abstract: With the tendency of reducing the size of semiconductor circuit patterns, edge roughness on a resist pattern is increased when pattern dimensions required are close to the size of the resist molecules. Provided is a technique for preventing degradation of the device performance and negative effects over the system performance caused by the phenomena. A photoresist compound is used, which is a molecule having functional groups that are chemically converted due to an action of an acid with reduced solubility in alkaline developer.
    Type: Grant
    Filed: December 1, 2006
    Date of Patent: February 9, 2010
    Assignee: Hitachi, Ltd.
    Inventors: Kyoko Kojima, Takashi Hattori
  • Patent number: 7655820
    Abstract: A method for producing a molecular compound which comprises mixing and kneading a solid host compound and a solid or liquid guest compound by using a kneader and optionally followed by extruding and granulating, wherein the method further comprises one or more of the steps of holding the product at a temperature which is 50° C. or higher and not higher than the emission temperature for the guest compound, washing the formed molecular compound with a solvent capable of dissolving the guest compound, pulverizing in advance the solid host compound, and adding a poor solvent such as water prior to mixing and kneading. The method allows the production of a molecular compound having improved stability.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: February 2, 2010
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masato Amaike, Seiji Sasaoka, Shigeru Kawamuko, Yasuaki Hashimoto, Eiji Takemura
  • 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
  • Publication number: 20090275772
    Abstract: An object of the present invention is to provide a method capable of producing a 1,2-phenylethane compound with extremely high yield in a short amount of time.
    Type: Application
    Filed: March 16, 2007
    Publication date: November 5, 2009
    Inventor: Takeshi Niitani
  • Patent number: 7601784
    Abstract: It is an object of the present invention to provide molecular compounds useful in the fields of state-of the-art materials, such as formulations, waste water treatments, energy transducers, conductors and bio-model reactions, in a way that interaction points and forces working inside polymer assemblies are fixed as well as controlled so that constituent polymers are aligned and modified. It is also an object of the present invention to provide methods for aligning and/or modifying polymers having hydrogen bond sites. A molecular compound is produced from a tetrakis aryl compound represented by Formula (I) (wherein, X is (CH2)n, or p-phenylene; n is 0, 1, 2 or 3; Y is hydroxyl, carboxyl or optionally substituted amino: and R1 and R2 are each hydrogen, lower alkyl, optionally substituted phenyl, halogen or lower alkoxy) and a polymer having hydrogen bond sites, such as polyethers, polyalcohols or polyamines.
    Type: Grant
    Filed: May 9, 2005
    Date of Patent: October 13, 2009
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hiroshi Suzuki, Satoru Abe
  • Patent number: 7586009
    Abstract: Provide a new bis-(hydroxybenzaldehyde) compound, as well as a new polynuclear polyphenol compound derived therefrom, suitable for use as component materials for photosensitive resist compositions, component materials and hardeners for epoxy resins, developers and anti-fading agents used in thermosensitive recording materials, bactericides, fungicides, antioxidants and other functional chemical products or component materials thereof, wherein such bis-(hydroxybenzaldehyde) compound is produced by reacting in the presence of trihalogenated acetic acid catalyst or phosphoric acid catalyst a 2,6-di(hydroxymethyl)-4-alkylphenol with a hydroxybenzaldehyde expressed by general formula (14).
    Type: Grant
    Filed: February 23, 2006
    Date of Patent: September 8, 2009
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Akira Yoshitomo, Tatsuya Iwai
  • Publication number: 20090162781
    Abstract: This resist composition is a resist composition containing a compound in which a portion or all of hydrogen atoms of phenolic hydroxyl groups in a polyhydric phenol compound (a) having two or more phenolic hydroxyl groups and having a molecular weight of 300 to 2,500 are substituted with at least one selected from the group consisting of acid dissociable dissolution inhibiting groups represented by the following general formulas (p1) and (p2) wherein R1 and R2 each independently represents a branched or cyclic alkyl group, and may contain a hetero atom in the structure; R3 represents a hydrogen atom or a lower alkyl group; and n? represents an integer of 1 to 3.
    Type: Application
    Filed: September 30, 2005
    Publication date: June 25, 2009
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Daiju Shiono, Taku Hirayama, Toshiyuki Ogata, Hideo Hada
  • Publication number: 20090076310
    Abstract: Provide a new bis-(hydroxybenzaldehyde) compound, as well as a new polynuclear polyphenol compound derived therefrom, suitable for use as component materials for photosensitive resist compositions, component materials and hardeners for epoxy resins, developers and anti-fading agents used in thermosensitive recording materials, bactericides, fungicides, antioxidants and other functional chemical products or component materials thereof, wherein such bis-(hydroxybenzaldehyde) compound is produced by reacting in the presence of trihalogenated acetic acid catalyst or phosphoric acid catalyst a 2,6-di(hydroxymethyl)-4-alkylphenol with a hydroxybenzaldehyde expressed by general formula (14).
    Type: Application
    Filed: February 23, 2006
    Publication date: March 19, 2009
    Inventors: Akira Yoshitomo, Tatsuya Iwai
  • Publication number: 20090042123
    Abstract: A calixresorcinarene compound represented by the following formula (1): wherein eight Rs are n (n is an integer of 1 to 7) substituents that are one or more types of substituents selected from groups represented by the following formula (2), and m (m is an integer shown by 8-n) hydrogen atoms; and R's, which may be the same or different, are each a straight-chain aliphatic hydrocarbon group having 2 to 12 carbon atoms, a branched aliphatic hydrocarbon group having 3 to 12 carbon atoms, a phenyl group, a p-phenylphenyl group, a p-tert-butylphenyl group, and an aromatic group represented by the following formula (3), or a substituent formed by combining two or more of these substituents: wherein R? is a hydrogen atom or a substituent selected from the substituents represented by the formula (2).
    Type: Application
    Filed: May 26, 2006
    Publication date: February 12, 2009
    Applicants: IDEMITSU KOSAN CO., LTD.
    Inventors: Hiroo Kinoshita, Takeo Watanabe, Hirotoshi Ishii, Takanori Owada
  • Publication number: 20090035691
    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: Application
    Filed: February 20, 2006
    Publication date: February 5, 2009
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Daiju Shiono, Taku Hirayama, Hideo Hada
  • Publication number: 20080220407
    Abstract: The presently described subject matter is directed to water-soluble conjugated polyene compounds that exhibit aggregation induced emission, as well as to water dispersible, fluorescent, polymeric microparticles and/or nanoparticles comprising the water-soluble conjugated polyene compounds. Also provided are methods of making and using the compounds and particles. The described conjugated polyene compounds are useful as bioprobes for the detection biomacromolecules, as well as in the manufacture of sensors.
    Type: Application
    Filed: December 10, 2007
    Publication date: September 11, 2008
    Applicant: The Hong Kong University of Science and Technology
    Inventors: Benzhong Tang, Yuning Hong, Matthias Haeussler, Hui Tong, Yonggiang Dong, Zhen Li, Changmin Xin
  • Publication number: 20080214876
    Abstract: A process for the preparation of a pharmaceutical-grade anhydrous calcipotriol comprising: (a) dissolving crude calcipotriol having a water content of X % by weight in a first solvent or in a mixture of two or more first solvents, said first solvent or said mixture of two or more first solvents forming an azeotropic system with water, to obtain a solution of crude calcipotriol; (b) obtaining an intermediate calcipotriol by (i) placing said solution of crude calcipotriol under a reduced pressure and evaporating, if X is greater than or equal to 1, or (ii) crystallizing, if X is lower than 1; and (c) re-dissolving said intermediate calcipotriol in a second solvent or a mixture of two or more second solvents, said second solvent being anhydrous, and crystallizing at least once to obtain pharmaceutical-grade anhydrous calcipotriol.
    Type: Application
    Filed: December 29, 2005
    Publication date: September 4, 2008
    Applicant: INSTYTUT FARMACEUTYCZNY
    Inventors: Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski
  • Patent number: 7414160
    Abstract: A process produces an aromatic compound by bringing an aromatic compound (B) into contact with molecular oxygen (C) in the presence of a catalyst (A) comprising at least one of (A1) a heteropolyacid and/or a salt thereof, and (A2) a mixture of oxoacids and/or salts thereof containing, as a whole, one of P and Si and at least one selected from V, Mo and W to thereby yield another aromatic compound (G) than the aromatic compound (B). The process can produce, for example, a corresponding aromatic hydroxy compound (G1) by allowing the aromatic compound (B) to react with the molecular oxygen (C) further in the presence of a reducing agent (D).
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: August 19, 2008
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Publication number: 20080188692
    Abstract: A process for preparing derivatized poly(4-hydroxystryrene) having a novolak type structure which comprises the steps of (i) supplying a solution of methanol containing 4-hydroxyphenylmethylcarbinol, (ii) subjecting said solution to an acid catalyzed displacement reaction for a sufficient period of time and under suitable conditions of temperature and pressure to convert substantially all of said carbinol to 4-hydroxyphenylmethylcarbinol methyl ether in solution, (iii) polymerizing said ether containing solution in the presence of a suitable acid catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form a novolak type polymer.
    Type: Application
    Filed: April 7, 2008
    Publication date: August 7, 2008
    Inventors: Michael T. Sheehan, Edward G. Zey
  • Publication number: 20080145784
    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, hydrogen atoms of phenolic hydroxyl groups within a polyhydric phenol compound, which has two or more phenolic hydroxyl groups, a molecular weight of 300 to 2,500, and is represented by a general formula (I) shown below, have been substituted with an acid-dissociable, dissolution-inhibiting group (II) represented by a general formula (II) shown below.
    Type: Application
    Filed: February 9, 2006
    Publication date: June 19, 2008
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Daiju Shiono, Taku Hirayama, Hideo Hada
  • Publication number: 20080081281
    Abstract: To overcome the problem that a device performance is degraded by the edge roughness of a photoresist pattern, a mixture of polynuclear phenol compounds having, in one molecule, 0 to 6 functional groups which are chemically converted due to actions of an acid with the solubility in an alkaline developer reduced is used as a material for photoresist. In the mixture, two or more triphenyl methane structures are bonded to portions other than the functional group in the nonconjugated state. Furthermore, the mixture comprises polynuclear compounds with the average number of functional groups of 2.5 or below and includes the polynuclear compounds not having any functional group per molecule by 15% or less in the term of weight ratio, and the polynuclear phenol compounds having 3 or more functional groups per molecule by 40% or less.
    Type: Application
    Filed: August 15, 2007
    Publication date: April 3, 2008
    Inventors: Kyoko KOJIMA, Hideo HADA, Daiju SHIONO
  • Publication number: 20070287105
    Abstract: A process for forming a resist pattern comprises the steps of applying on a substrate to form a photosensitive resist layer a photosensitive composition comprising at least one photosensitive compound having, in the molecule, two or more structural units represented by C6R2-6—CHR1—OR7 or C6R2-6—CHR1—COOR7 where R1 is a hydrogen atom or an alkyl group, at least one of R2, R3, R4, R5, and R6 is a nitro group, and others are selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl, an alkoxy, a phenyl, a naphthyl, and an alkyl in which a part or the entire of hydrogen atoms are substituted by a fluorine atom, and R7 is a substituted or unsubstituted phenylene or naphthylene group dissolved in an organic solvent, irradiating the resist layer selectively with a radiation ray, and developing a portion irradiated by the ray to form a pattern of the resist layer.
    Type: Application
    Filed: May 10, 2007
    Publication date: December 13, 2007
    Applicant: CANON KABUSHIKI KAISHA
    Inventors: Toshiki Ito, Takako Yamaguchi
  • Patent number: 7304189
    Abstract: A method for preparing 1,1,1,-tris(4-hydroxyphenyl)alkanes generally comprises reacting a mixture of an aromatic hydroxy compound and a ketone in the presence of at least one ion exchange resin catalyst and optionally a co-catalyst to produce the 1,1,1-tris(4-hydroxyphenyl)alkanes of formula:
    Type: Grant
    Filed: January 31, 2005
    Date of Patent: December 4, 2007
    Assignee: General Electric Company
    Inventors: Adil Minoo Dhalla, Raina Gupta, Gurram Kishan, Yongcheng Li, G. V. Ramanarayanan
  • Patent number: 7291756
    Abstract: A method for producing a molecular compound which comprises mixing and kneading a solid host compound and a solid or liquid guest compound by using a kneader and optionally followed by extruding and granulating, wherein the method further comprises one or more of the steps of holding the product at a temperature which is 50° C. or higher and not higher than the emission temperature for the guest compound, washing the formed molecular compound with a solvent capable of dissolving the guest compound, pulverizing in advance the solid host compound, and adding a poor solvent such as water prior to mixing and kneading. The method allows the production of a molecular compound having improved stability.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: November 6, 2007
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masato Amaike, Seiji Sasaoka, Shigeru Kawamuko, Yasuaki Hashimoto, Eiji Takemura
  • Publication number: 20070232839
    Abstract: A polynuclear polyphenol compound is constituted by, as a main skeleton, a 4,4?-methylene bis phenol structure where tris phenol skeletons of tris phenyl methane type are mutually bonded by methylene groups, wherein the reactivity of two hydroxyl groups bonded to the central skeleton of 4,4?-methylene bis phenol is significantly different from the reactivity of hydroxyl groups respectively bonded to the four phenyl groups of the two diphenyl methyl substituted groups.
    Type: Application
    Filed: March 28, 2007
    Publication date: October 4, 2007
    Inventors: Akira Yoshitomo, Tatsuya Iwai
  • Patent number: 7169957
    Abstract: Disclosed are the general principles upon which closed molecular or ionic structural frameworks may be prepared. These frameworks are based upon the self-assembly (wherein the term self-assembly refers to the association of chemical components through inter-component bonds) of n>4 subunits where surface curvature is supplied by edge sharing of subunits.
    Type: Grant
    Filed: April 7, 2003
    Date of Patent: January 30, 2007
    Inventors: Jerry L. Atwood, Leonard R. MacGillivray
  • Patent number: 7087799
    Abstract: An object of the present invention is to provide a material which resolves the drawbacks associated with polyimide polymers, and yet retains the advantages offered by conventional polyimide polymers. An amino group containing phenol derivative of the present invention is represented by a general formula (1) show below, and the present invention also provides a polyimide precursor produced using such an amino group containing phenol derivative. (wherein, R1, R2 and R3, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a COOR group (in which R represents an alkyl group of 1 to 6 carbon atoms) or a hydrogen atom; R4 and R5, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms or a hydrogen atom; X represents —O—, —S—, —SO2—, —C(CH3)2—, —CH2—, —C(CH3)(C2H5)—, or —C(CF3)2—; and n represents an integer of 1 or greater).
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: August 8, 2006
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
  • Patent number: 7019179
    Abstract: A process produces an aromatic compound by bringing an aromatic compound (B) into contact with molecular oxygen (C) in the presence of a catalyst (A) comprising at least one of (A1) a heteropolyacid and/or a salt thereof, and (A2) a mixture of oxoacids and/or salts thereof containing, as a whole, one of P and Si and at least one selected from V, Mo and W to thereby yield another aromatic compound (G) than the aromatic compound (B). The process can produce, for example, a corresponding aromatic hydroxy compound (G1) by allowing the aromatic compound (B) to react with the molecular oxygen (C) further in the presence of a reducing agent (D).
    Type: Grant
    Filed: March 6, 2003
    Date of Patent: March 28, 2006
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6727325
    Abstract: The present invention has an object to provide curatives for epoxy resins and curing accelerators for epoxy resins, which both have improved subliming and decomposing properties and which, when mixed with an epoxy resin, enable the mixture to be greatly improved in thermal stability that is extremely important for the control of a curing reaction and to have a prolonged pot life (stability as a one-pack mixture comprising the epoxy resin, curative, etc.) and improved curability at low temperatures.
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: April 27, 2004
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Hiroshi Suzuki, Satoru Abe, Izuo Aoki
  • Patent number: 6723801
    Abstract: An object of the present invention is to provide an epoxy resin composition which has high flexibility, can be molded to a thin membrane, and can become a noninflammable cured product. The present invention comprises a polyphenol compound obtained by reacting to condense phenol with bischloromethyl biphenyl or bismethoxymethyl biphenyl, removing unreacted phenol and then reacting with BCMB again, wherein the polyphenol compound has a weight-average molecular weight of 3,000 or more as determined by GPC, and using the polyphenol compound as an agent for curing an epoxy resin.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: April 20, 2004
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yasumasa Akatsuka, Toyofumi Asano, Masahiro Imaizumi, Katsuhiko Oshimi, Syouichi Tomida
  • Patent number: 6670512
    Abstract: The present invention seeks to provide novel tetraarylethylene compounds which are substituted on the aryl rings ortho to the ethylenic carbon atoms and processes for the preparation for such compounds. The compounds have potential use as molecular templates.
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: December 30, 2003
    Inventors: Jeffrey Mark Stryker, Udo Hendrick Verkerk, Megumi Fujita, Makoto Yasuda
  • Patent number: 6620978
    Abstract: The present invention provides a positive photoresist composition including (A) an alkali-soluble resin and (B) a photosensitizer, and the ingredient (B) is a quinonediazide ester of, for example, 2,6-bis[4-hydroxy-3-(2-hydroxy-3,5-dimethylbenzyl)-2,5-dimethylbenzyl]-4-methylphenol, where the average degree of esterification of 20% to 80%.
    Type: Grant
    Filed: July 31, 2002
    Date of Patent: September 16, 2003
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20030054283
    Abstract: The present invention provides a positive photoresist composition including (A) an alkali-soluble resin and (B) a photosensitizer, and the ingredient (B) is a quinonediazide ester of, for example, 2,6-bis[4-hydroxy-3-(2-hydroxy-3,5-dimethylbenzyl)-2,5-dimethylbenzyl]-4-methylphenol, where the average degree of esterification of 20% to 80%.
    Type: Application
    Filed: July 31, 2002
    Publication date: March 20, 2003
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20020142923
    Abstract: Hindered tert-butylphenolic antioxidant compositions characterized by a low level of volatile and undesirable single-ring tert-butylphenolic antioxidants and a high level of non-volatile multi-ring (or methylene bridged) tert-butylphenolic antioxidants are obtained by reacting a specific mixture of ultra pure ortho-tert-butylphenol (OTBP), ultra pure 2,6-di-tert-butylphenol (DTBP) and formaldehyde in a solvent in the presence of catalyst. These antioxidants are further characterized by having a low level of 2,6-di-tert-butylphenol, low levels of ortho-tert-butylphenol, and trace levels of 2,4,6-tri-tert-butylphenol.
    Type: Application
    Filed: March 8, 2002
    Publication date: October 3, 2002
    Inventor: Vincent J. Gatto
  • Patent number: 6358431
    Abstract: A method of imparting a water repellent surface to a hydrophilic substrate which comprises contacting the substrate with a solution or dispersion of a suitable calixarene in a liquid medium.
    Type: Grant
    Filed: February 24, 1999
    Date of Patent: March 19, 2002
    Assignee: The University of Sheffield
    Inventors: Charles James Matthew Stirling, Frank Davis
  • Patent number: 6207788
    Abstract: A novolak resin precursor is composed of bonded phenolic moieties, one of the hydrogen atoms in the o- or p-positions relative to the hydroxy group of each phenolic moiety is substituted with an alkyl or alkenyl group having 1 to 3 carbon atoms, and the other two hydrogen atoms are bonded through methylene bonds. The content of ortho—ortho bonding is 30 to 70% relative to the number of total methylene bonds and the weight average molecular weight of the precursor is 300 to 10,000. A novolak resin is obtained from this precursor, and a positive photoresist composition comprises this novolak resin. The invention provides a positive photoresist composition that comprises less binuclear compounds, suppresses scum formation, is excellent in terms of definition and coating performance and provides a resist pattern having satisfactory heat resistance.
    Type: Grant
    Filed: July 24, 1998
    Date of Patent: March 27, 2001
    Assignee: Tokyo Ohka Kogya Co., Ltd.
    Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6147169
    Abstract: A curable coating composition comprising (A) a functional group-containing base resin and (B) a clathrate compound consisting of (i) at least one guest compound selected from the group consisting of a curing agent having a functional group crosslinkable with the functional group of the base resin and a curing catalyst, and (ii) a host compound consisting of tetrakisphenols.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: November 14, 2000
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Kazuhiko Ohnishi
  • Patent number: 6120969
    Abstract: Disclosed is, for example, bis(2,5-dimethyl-3-(2-hydroxy-5-ethylbenzyl)-4-hydroxyphenyl)methane and quinonediazide ester thereof. These are used for positive photoresist compositions. According to the invention, positive photoresist compositions having a high definition, a high sensitivity and a large exposure margin can be provided.
    Type: Grant
    Filed: April 2, 1999
    Date of Patent: September 19, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Mitsuo Hagihara, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama, Tetsuya Nakajima
  • Patent number: 6049014
    Abstract: A process for producing n-propyl bromide during the bromination of bis- or trisphenols uses non-aqueous n-propanol as the bromination solvent, providing salable yields of n-propyl bromide to accompany the brominated bisphenol or trisphlenol.
    Type: Grant
    Filed: February 19, 1998
    Date of Patent: April 11, 2000
    Assignee: Great Lakes Chemical Corporation
    Inventors: Anne P. Noonan, Stephen C. Scherrer
  • 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: 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: 5908965
    Abstract: The present invention relates to a build-up suppressant used for suppressing the formation of a build-up during the polymerization reaction and to a process for the preparation thereof. The present invention also relates to a method for suppressing the build-up formation by forming a coating film on the reactor internal surface with the build-up suppressant and to a method for polymerization of vinyl halide or vinyl monomers having aromatic group(s) in the above reactor internally coated.
    Type: Grant
    Filed: November 20, 1995
    Date of Patent: June 1, 1999
    Assignee: Hanwha Chemical Corporation
    Inventors: Oh-Sig Kwon, Young Wook Kim, Il Won Kim, Young Gyu Kim, Ho Yeon Won
  • Patent number: 5866724
    Abstract: A positive photoresist compositions comprising, as a photosensitizer, a quinonediazide sulfonic acid ester of a phenol compound represented by the following formula (I): ##STR1## wherein Q.sup.1, Q.sup.2, Q.sup.3, Q.sup.4, Q.sup.5, Q.sup.6, Q.sup.7, Q.sup.8, Q.sup.9 and Q.sup.10 independently represent hydrogen, alkyl having 1-6 carbon atoms or phenyl, or Q.sup.1 and Q.sup.2, Q.sup.3 and Q.sup.4, Q.sup.5 and Q.sup.6, Q.sup.7 and Q.sup.8, or Q.sup.9 and Q.sup.10 may form a cycloalkane ring having 6 or less carbon atoms together with a carbon atoms to which they are connected, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 independently represent hydrogen, hydroxyl, alkyl having 1-6 carbon atoms or phenyl; andm and n independently represent a number of 0 or 1;and an alkali soluble resin;and a quinonediazide sulfonic acid ester of a phenol compound of formula (I).
    Type: Grant
    Filed: October 17, 1996
    Date of Patent: February 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Haruyoshi Osaki, Hiroki Inoue
  • Patent number: 5807656
    Abstract: A polyhydroxy compound represented by the following formula (I): ##STR1## and a positive resist composition which comprises an alkali-soluble resin, a quinonediazide sulfonic acid ester, and a polyhydroxy compound of formula (I) or a polyhydroxy compound represented by the following formula (C): ##STR2## which is satisfactory in properties such as sensitivity, resolution, .tau.-value and peeling off resistance.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: September 15, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Haruyoshi Osaki, Yasunori Uetani, Yoshiyuki Takata
  • Patent number: 5770763
    Abstract: Novel difunctionalized cyclobutabenzene monomers of the general formula: ##STR1## wherein Z can be hydrogens or a cyclobutane ring; and X and Y are carboxyl, amino, alcohol, isocyanate, acid halide, or bis-acyl halide groups. Exemplary difunctional bitricyclodecatriene monomers are ?2,2'-bidicyclo?2.4.0!octa-1,3,5-triene!-5,5'-dicarboxylic acid (BXTA) and ?2,2'-bitricyclo?6.2.0.0!deca-1,3,(6),7-triene!-7,7'-dicarboxylic acid (QXTA). The difunctionalized bitricyclodecatriene monomers can form part of a polymer backbone chain in which the multiple butane ring functionalities can be easily opened to produce strong, three-dimensional covalent bond crosslinking between polymer chains. The crosslinking can be induced simply by heating the polymer to a temperature in excess of 250.degree. C.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: June 23, 1998
    Assignee: The Board of Regents of the Univ. of Michigan
    Inventors: David C. Martin, Jeffrey S. Moore, Larry J. Markoski, Kenneth A. Walker, Gary E. Spilman
  • Patent number: 5763686
    Abstract: 1,1,1-Tris(4-hydroxyphenyl)ethane, a branching agent for polycarbonates, is prepared by the reaction of phenol with 2,4-pentanedione in the presence of sulfuric acid and at least one mercapto sulfonic acid such as 3-mercaptopropanesulfonic acid as promoter. By employing specific proportions of the promoter and sulfuric acid, high product yields can be obtained in relatively short times.
    Type: Grant
    Filed: December 16, 1996
    Date of Patent: June 9, 1998
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Eric James Pressman
  • Patent number: 5756859
    Abstract: 1,1,1-Tris(4-hydroxyphenyl)ethane in admixture with bisphenol A is obtained by the reaction of 2,4-pentanedione with excess phenol under acidic conditions and in the presence of a mercapto compound as promoter. The products may be separated by extracting bisphenol A with a chlorinated alkane. Purification of the resulting 1,1,1-tris(4-hydroxyphenyl)ethane is achieved by slurrying in and/or recrystallization from methanol-water, optionally with addition of an alkali metal borohydride or dithionite.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: May 26, 1998
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Paul Dean Sybert, Julia Lam Lee, David Michel Dardaris
  • Patent number: 5744653
    Abstract: A method for preparing 1,3-dihydroxy-4,6-bis?.alpha.-methyl-.alpha.-.alpha.(4'-hydroxyphenyl)ethy l!benzene represented by the following formula (1): ##STR1## comprising the step of initiating a reaction of resorcin with 4-isopropenylphenol in a mixed solvent which comprises a non-polar solvent and a polar solvent in the presence of an acidic catalyst. The method can easily be handled, ensures a high yield, permits the reduction of impurity content and can provide highly pure 1,3-dihydroxy-4,6-bis?.alpha.-methyl-.alpha.-(4'-hydroxyphenyl)ethyl!benze ne. The resulting phenolic compound is useful as, for instance, a branching agent for polycarbonates, polyesters or the like; a raw material for radiant ray-sensitive components for use as resist materials; a raw material for epoxy resins; and a hardening agent for epoxy resins.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: April 28, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Mizuo Ito, Shigeru Iimuro
  • Patent number: 5672776
    Abstract: Tris(4-hydroxyphenyl)alkanes such as 1,1,1 -tris(4-hydroxyphenyl)ethane are purified by formation of an adduct with a molar excess of a C.sub.1-4 primary alkyl tertiary amine, preferably triethylamine. Adduct formation is preferably effected in a polar organic solvent such as methanol. The pure tris(4-hydroxyphenyl)alkane may be recovered from the adduct by thermal or aqueous acid-promoted cracking.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: September 30, 1997
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Julia Lam Lee
  • Patent number: 5602260
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the variables are as defined in the description.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: February 11, 1997
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
  • Patent number: 5554797
    Abstract: Positive photoresist compositions comprising, in an organic solvent, at leasta) one alkali-soluble resin,b) one photosensitive quinone diazide,c) one aromatic hydroxy compound of formula I ##STR1## wherein each R is --H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy,--OCH.sub.2 C.sub.6 H.sub.5, --OC.sub.6 H.sub.5 or --COOC.sub.1 -C.sub.4 alkyl, and R.sub.1 and R.sub.2 are each independently of the other H, C.sub.1 -C.sub.4 alkyl,--C.sub.6 H.sub.5 or a cycloaliphatic 5- or 6-membered ring, a is an integer from 0 to 4, and m and n are each independently of the other 0, 1 or 2, which compound enhances the photosensitivity and/or the rate of development, and optionallyd) additional customary modifiers,are eminently suitable for making relief structures.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: September 10, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Reinhard Schulz, Norbert M unzel, Martin Roth, Wilhelm Knobloch
  • Patent number: 5541282
    Abstract: The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-[1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: July 30, 1996
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset
  • Patent number: 5488182
    Abstract: A novel methoxymethyl- or hydroxymethyl-containing phenol compound represented by the following formula (I), (II), (III), (IV) or (V) is disclosed: ##STR1## wherein each R represents CH.sub.2 OCH.sub.3, CH.sub.2 OH, or H, provided that at least three of the R's are CH.sub.2 OCH.sub.3 or CH.sub.2 OH, with at least one thereof being CH.sub.2 OCH.sub.3 ; each R.sub.1 represents CH.sub.2 OCH.sub.3, CH.sub.2 OH, or H, provided that at least two of the R.sub.1 's are CH.sub.2 OH; and each R.sub.2 represents CH.sub.2 OCH.sub.3, CH.sub.2 OH, or H, provided that at least two of the R.sub.2 'S are CH.sub.2 OH.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: January 30, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumikazu Kobayashi, Kazuyoshi Mizutani, Kazuo Maemoto
  • Patent number: 5438142
    Abstract: Compounds useful as polymer stabilizers which are polymerizable into condensation polymer systems are disclosed and claimed. A particularly preferred embodiment is 1-(3'-(benzotriazol-2"-yl)-4'-hydroxyphenyl)-1,1-bis(4-hydroxyphenyl)ethan e.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: August 1, 1995
    Assignee: Hoechst Celanese Corp.
    Inventors: John R. Fritsch, Olan S. Fruchey, Debasish Kuila, George Kvakovszky, Mark A. Murphy, Michael T. Sheehan, James R Sounik, Richard Vicari
  • Patent number: 5382710
    Abstract: The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: January 17, 1995
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset