Three Or More Phenols Containing Patents (Class 568/720)
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Patent number: 7659047Abstract: 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: GrantFiled: December 1, 2006Date of Patent: February 9, 2010Assignee: Hitachi, Ltd.Inventors: Kyoko Kojima, Takashi Hattori
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Patent number: 7655820Abstract: 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: GrantFiled: September 5, 2007Date of Patent: February 2, 2010Assignee: Nippon Soda Co., Ltd.Inventors: Masato Amaike, Seiji Sasaoka, Shigeru Kawamuko, Yasuaki Hashimoto, Eiji Takemura
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Patent number: 7648816Abstract: 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: GrantFiled: February 20, 2006Date of Patent: January 19, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Daiju Shiono, Taku Hirayama, Hideo Hada
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Publication number: 20090275772Abstract: 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: ApplicationFiled: March 16, 2007Publication date: November 5, 2009Inventor: Takeshi Niitani
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Patent number: 7601784Abstract: 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: GrantFiled: May 9, 2005Date of Patent: October 13, 2009Assignee: Nippon Soda Co., Ltd.Inventors: Hiroshi Suzuki, Satoru Abe
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Patent number: 7586009Abstract: 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: GrantFiled: February 23, 2006Date of Patent: September 8, 2009Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Akira Yoshitomo, Tatsuya Iwai
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Publication number: 20090162781Abstract: 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: ApplicationFiled: September 30, 2005Publication date: June 25, 2009Applicant: TOKYO OHKA KOGYO CO., LTD.Inventors: Daiju Shiono, Taku Hirayama, Toshiyuki Ogata, Hideo Hada
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Publication number: 20090076310Abstract: 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: ApplicationFiled: February 23, 2006Publication date: March 19, 2009Inventors: Akira Yoshitomo, Tatsuya Iwai
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Publication number: 20090042123Abstract: 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: ApplicationFiled: May 26, 2006Publication date: February 12, 2009Applicants: IDEMITSU KOSAN CO., LTD.Inventors: Hiroo Kinoshita, Takeo Watanabe, Hirotoshi Ishii, Takanori Owada
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Publication number: 20090035691Abstract: 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: ApplicationFiled: February 20, 2006Publication date: February 5, 2009Applicant: TOKYO OHKA KOGYO CO., LTD.Inventors: Daiju Shiono, Taku Hirayama, Hideo Hada
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Publication number: 20080220407Abstract: 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: ApplicationFiled: December 10, 2007Publication date: September 11, 2008Applicant: The Hong Kong University of Science and TechnologyInventors: Benzhong Tang, Yuning Hong, Matthias Haeussler, Hui Tong, Yonggiang Dong, Zhen Li, Changmin Xin
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Publication number: 20080214876Abstract: 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: ApplicationFiled: December 29, 2005Publication date: September 4, 2008Applicant: INSTYTUT FARMACEUTYCZNYInventors: Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski
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Patent number: 7414160Abstract: 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: GrantFiled: December 20, 2005Date of Patent: August 19, 2008Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Publication number: 20080188692Abstract: 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: ApplicationFiled: April 7, 2008Publication date: August 7, 2008Inventors: Michael T. Sheehan, Edward G. Zey
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Publication number: 20080145784Abstract: 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: ApplicationFiled: February 9, 2006Publication date: June 19, 2008Applicant: TOKYO OHKA KOGYO CO., LTD.Inventors: Daiju Shiono, Taku Hirayama, Hideo Hada
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Publication number: 20080081281Abstract: 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: ApplicationFiled: August 15, 2007Publication date: April 3, 2008Inventors: Kyoko KOJIMA, Hideo HADA, Daiju SHIONO
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Publication number: 20070287105Abstract: 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: ApplicationFiled: May 10, 2007Publication date: December 13, 2007Applicant: CANON KABUSHIKI KAISHAInventors: Toshiki Ito, Takako Yamaguchi
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Patent number: 7304189Abstract: 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: GrantFiled: January 31, 2005Date of Patent: December 4, 2007Assignee: General Electric CompanyInventors: Adil Minoo Dhalla, Raina Gupta, Gurram Kishan, Yongcheng Li, G. V. Ramanarayanan
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Patent number: 7291756Abstract: 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: GrantFiled: December 11, 2001Date of Patent: November 6, 2007Assignee: Nippon Soda Co., Ltd.Inventors: Masato Amaike, Seiji Sasaoka, Shigeru Kawamuko, Yasuaki Hashimoto, Eiji Takemura
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Publication number: 20070232839Abstract: 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: ApplicationFiled: March 28, 2007Publication date: October 4, 2007Inventors: Akira Yoshitomo, Tatsuya Iwai
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Patent number: 7169957Abstract: 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: GrantFiled: April 7, 2003Date of Patent: January 30, 2007Inventors: Jerry L. Atwood, Leonard R. MacGillivray
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Patent number: 7087799Abstract: 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: GrantFiled: January 31, 2003Date of Patent: August 8, 2006Assignee: Gun Ei Chemical Industry Co., Ltd.Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
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Patent number: 7019179Abstract: 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: GrantFiled: March 6, 2003Date of Patent: March 28, 2006Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6727325Abstract: 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: GrantFiled: June 23, 1999Date of Patent: April 27, 2004Assignee: Nippon Soda Co. Ltd.Inventors: Hiroshi Suzuki, Satoru Abe, Izuo Aoki
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Patent number: 6723801Abstract: 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: GrantFiled: May 31, 2002Date of Patent: April 20, 2004Assignee: Nippon Kayaku Kabushiki KaishaInventors: Yasumasa Akatsuka, Toyofumi Asano, Masahiro Imaizumi, Katsuhiko Oshimi, Syouichi Tomida
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Patent number: 6670512Abstract: 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: GrantFiled: June 21, 2002Date of Patent: December 30, 2003Inventors: Jeffrey Mark Stryker, Udo Hendrick Verkerk, Megumi Fujita, Makoto Yasuda
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Patent number: 6620978Abstract: 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: GrantFiled: July 31, 2002Date of Patent: September 16, 2003Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
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Publication number: 20030054283Abstract: 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: ApplicationFiled: July 31, 2002Publication date: March 20, 2003Applicant: TOKYO OHKA KOGYO CO., LTD.Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
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Publication number: 20020142923Abstract: 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: ApplicationFiled: March 8, 2002Publication date: October 3, 2002Inventor: Vincent J. Gatto
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Patent number: 6358431Abstract: 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: GrantFiled: February 24, 1999Date of Patent: March 19, 2002Assignee: The University of SheffieldInventors: Charles James Matthew Stirling, Frank Davis
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Patent number: 6207788Abstract: 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: GrantFiled: July 24, 1998Date of Patent: March 27, 2001Assignee: Tokyo Ohka Kogya Co., Ltd.Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6147169Abstract: 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: GrantFiled: March 25, 1998Date of Patent: November 14, 2000Assignee: Kansai Paint Co., Ltd.Inventor: Kazuhiko Ohnishi
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Patent number: 6120969Abstract: 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: GrantFiled: April 2, 1999Date of Patent: September 19, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuo Hagihara, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama, Tetsuya Nakajima
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Patent number: 6049014Abstract: 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: GrantFiled: February 19, 1998Date of Patent: April 11, 2000Assignee: Great Lakes Chemical CorporationInventors: Anne P. Noonan, Stephen C. Scherrer
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Patent number: 6015873Abstract: 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: GrantFiled: June 26, 1997Date of Patent: January 18, 2000Assignee: Shell Oil CompanyInventors: Mareki Miura, Yoshinobu Ohnuma
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Patent number: 5932623Abstract: 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: GrantFiled: November 9, 1995Date of Patent: August 3, 1999Assignee: The Nikka Whisky Distilling Co., Ltd.,Inventors: Masayuki Tanabe, Tomomasa Kanda, Akio Yanagida
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Patent number: 5908965Abstract: 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: GrantFiled: November 20, 1995Date of Patent: June 1, 1999Assignee: Hanwha Chemical CorporationInventors: Oh-Sig Kwon, Young Wook Kim, Il Won Kim, Young Gyu Kim, Ho Yeon Won
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Patent number: 5866724Abstract: 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: GrantFiled: October 17, 1996Date of Patent: February 2, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Haruyoshi Osaki, Hiroki Inoue
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Patent number: 5807656Abstract: 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: GrantFiled: September 4, 1996Date of Patent: September 15, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Haruyoshi Osaki, Yasunori Uetani, Yoshiyuki Takata
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Patent number: 5770763Abstract: 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: GrantFiled: August 30, 1996Date of Patent: June 23, 1998Assignee: The Board of Regents of the Univ. of MichiganInventors: David C. Martin, Jeffrey S. Moore, Larry J. Markoski, Kenneth A. Walker, Gary E. Spilman
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Patent number: 5763686Abstract: 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: GrantFiled: December 16, 1996Date of Patent: June 9, 1998Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Eric James Pressman
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Patent number: 5756859Abstract: 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: GrantFiled: December 4, 1996Date of Patent: May 26, 1998Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Paul Dean Sybert, Julia Lam Lee, David Michel Dardaris
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Patent number: 5744653Abstract: 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: GrantFiled: August 19, 1996Date of Patent: April 28, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Mizuo Ito, Shigeru Iimuro
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Patent number: 5672776Abstract: 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: GrantFiled: September 27, 1996Date of Patent: September 30, 1997Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Julia Lam Lee
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Patent number: 5602260Abstract: 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: GrantFiled: May 26, 1995Date of Patent: February 11, 1997Assignee: OCG Microelectronic Materials, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
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Patent number: 5554797Abstract: 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: GrantFiled: March 7, 1995Date of Patent: September 10, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Reinhard Schulz, Norbert M unzel, Martin Roth, Wilhelm Knobloch
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Patent number: 5541282Abstract: 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: GrantFiled: November 9, 1994Date of Patent: July 30, 1996Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset
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Patent number: 5488182Abstract: 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: GrantFiled: June 30, 1994Date of Patent: January 30, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Fumikazu Kobayashi, Kazuyoshi Mizutani, Kazuo Maemoto
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Patent number: 5438142Abstract: 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: GrantFiled: August 10, 1993Date of Patent: August 1, 1995Assignee: 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
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Patent number: 5382710Abstract: 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: GrantFiled: July 30, 1992Date of Patent: January 17, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset