Cyclic Alcohol Moiety Patents (Class 560/220)
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Publication number: 20100120907Abstract: Provided are topical formulations comprising an Amyris alcohol and/or ester derivatives of Amyris alcohol which may be used for the treatment of diseases including herpes virus infection (e.g., HSV-1, HSV-2), epidermoid carcinoma, cold sores, and human papillomavirus. Amyris alcohols contemplated for use with the present invention include valerianol, beta-eudesmol, epi-gamma-eudesmol, elemol, alpha-eudesmol, and ester derivatives thereof.Type: ApplicationFiled: April 18, 2008Publication date: May 13, 2010Inventors: Chandra Ulagaraj Singh, Rao Jagaveerabhadra Nulu
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Publication number: 20100103366Abstract: The invention relates to new cyclohexylene reactive mesogens (RM), polymers derived thereof, liquid crystal (LC) media comprising them, and the use of the compounds, polymers and liquid crystalline media in optical, electrooptical, electronic, semiconducting or luminescent components or devices, in decorative, security, cosmetic or diagnostic applications, especially in the polymer stabilised blue phase.Type: ApplicationFiled: October 26, 2007Publication date: April 29, 2010Applicant: MERCK PATENT GMBHInventors: Louise Diane Farrand, Kevin Adlem, Andreas Taugerbeck, John Patrick, Christopher John Dunn, Janice Mccreary
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Patent number: 7700261Abstract: A positive photosensitive composition comprises: (A) a compound that generates an acid upon irradiation with actinic ray or radiation; and (B) a resin that increases its solubility in an alkali developer by action of an acid, wherein the resin (B) has a repeating unit that has an acid-decomposable group and is represented by formula (I): wherein Xa1 represents a hydrogen atom, an alkyl group, a cyano group, or a halogen atom; Ry1 and Ry2 each independently represents an alkyl group or a cycloalkyl group; Rx represents an alkyl group having 2 or more carbon atoms, or a cycloalkyl group; and Z represents an alkylene group.Type: GrantFiled: March 26, 2008Date of Patent: April 20, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Kaoru Iwato, Hideaki Tsubaki, Norihiko Taguchi
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Patent number: 7687222Abstract: Novel polymerizable ester compounds having formulae (1) to (4) undergo no acid-induced decomposition by ?-elimination wherein A1 is a polymerizable functional group having a carbon-carbon double bond, R1 is H or āCā(R5)3, R2 and R3 are alkyl, R4 is H or alkyl, R5 is a monovalent hydrocarbon group, X is alkylene, Y is methylene, ethylene or isopropylidene, Z is alkylene, and n=1 or 2. Resist compositions comprising polymers derived from the ester compounds have excellent sensitivity and resolution and lend themselves to micropatterning lithography.Type: GrantFiled: July 5, 2007Date of Patent: March 30, 2010Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa, Seiichiro Tachibana, Masaki Ohashi
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Publication number: 20100062374Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, X is a single bond or methylene, m is 1 or 2, and the hydroxyl group attaches to a secondary carbon atom. The composition is improved in resolution when processed by lithography.Type: ApplicationFiled: September 3, 2009Publication date: March 11, 2010Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Tsunehiro NISHI, Takeshi KINSHO, Masaki OHASHI, Koji HASEGAWA, Masashi IIO
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Publication number: 20100048757Abstract: Disclosed herein is an adamantane derivative represented by the following general formula (I): (wherein R represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; Y represents a hydrogen atom, a hydroxyl group, ?O formed by two Ys together, a carboxyl group, or a hydrocarbon group having 1 to 20 carbon atoms or a cyclic hydrocarbon group having 3 to 20 carbon atoms; m is 13 and n is 3, or m is 12 and n is 4; and p is an integer of one or more), a production method thereof, a resin composition containing the adamantane derivative, and a cured product thereof.Type: ApplicationFiled: October 24, 2007Publication date: February 25, 2010Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Yasunari Okada, Hideki Yamane, Katsuki Ito, Nobuaki Matsumoto
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Publication number: 20100022730Abstract: A polymerizable compound having a fluorinated substituent (Z) represented by the general formula (1), an adamantane structure and a polymerizable group (A) having the structure represented by the general formula (1), a production method thereof, and a photoresist composition, a thermocurable resin composition and a photocurable resin composition containing a polymer obtained using the polymerizable compound are provided. Use of the polymerizable compound with the adamantane structure and a resin composition thereof in the present invention provides in the field of photolithography the effect of preventing a liquid immersion medium from penetration and improving dry etching resistance in a liquid immersion exposure method as well as reducing adhesion to a mold and improving dry etching resistance in a nanoimprint method.Type: ApplicationFiled: July 9, 2007Publication date: January 28, 2010Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Naoyoshi Hatakeyama, Hidetoshi Ono, Katsuki Ito
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Publication number: 20100016532Abstract: To provide a novel fluorinated compound, a fluoropolymer and a method for producing the compound. A compound represented by the formula CF2?CFCF2C(X)(C(O)OZ)(CH2)nCR?CHR (wherein X is a hydrogen atom, a cyano group or a group represented by the formula āC(O)OZ, Z is a hydrogen atom or a C1-20 monovalent organic group, n is 0, 1, or 2, and R is a hydrogen atom or a C1-20 monovalent organic group), a method for producing it, and a fluoropolymer obtained by polymerizing the compound.Type: ApplicationFiled: September 28, 2009Publication date: January 21, 2010Applicant: Asahi Glass Company, LimitedInventors: Koichi Murata, Naoko Shirota, Osamu Yokokoji, Yoko Takebe
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Publication number: 20090239179Abstract: A hydroxyl-containing monomer of formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are monovalent C1-C15 hydrocarbon groups, or R2 and R3 may form an aliphatic ring. The monomers are useful for the synthesis of polymers which have high transparency to radiation of up to 500 nm and the effect of controlling acid diffusion so that the polymers may be used as a base resin to formulate radiation-sensitive resist compositions having a high resolution.Type: ApplicationFiled: March 17, 2009Publication date: September 24, 2009Inventors: Takeshi Kinsho, Masaki Ohashi, Koji Hasegawa, Takeru Watanabe
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Publication number: 20090198065Abstract: To provide a resist polymer comprising, as a structural unit, an acid-decomposable unit having a structure represented by formula (1) or (2) which exhibits a small line edge roughness and produces little defects in DUV excimer laser lithography or the like.Type: ApplicationFiled: March 26, 2009Publication date: August 6, 2009Applicant: Mitsubishi Rayon Co., Ltd.Inventors: Hikaru Momose, Atsushi Ootake, Tadashi Nakamura, Akifumi Ueda
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Publication number: 20090198014Abstract: A mixture of compounds useful to make a polymer or a prepolymer, the mixture of compounds including compounds having the formula I; wherein R1 is H, acryloyl, methacryloyl or vinyl, wherein R2 is acryloyl, methacryloyl or vinyl, wherein compounds having the formula I consist of a mixture of cis and trans-1,3- and 1,4-substituted cyclohexane and wherein the trans-1,4-substituted cyclohexane content of the compounds having the formula I is less than forty mole percent. A process for producing a mixture of compounds including compounds having the formula II: wherein compounds having the formula II consist of a mixture of cis and trans-1,3- and 1,4-methanol substituted cyclohexane and wherein the trans-1,4-methanol substituted cyclohexane content of the compounds having the formula II is less than twenty five mole percent.Type: ApplicationFiled: December 7, 2006Publication date: August 6, 2009Inventors: Kiran K. Baikerikar, Michael L. Tulchinsky, John N. Argyropoulos
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Publication number: 20090156854Abstract: The present invention provides an adamantane derivative (I) having a structure represented by the general formula (I); an adamantane derivative (II) having a structure represented by the general formula (II); and a process for producing those adamantane derivatives. An alcohol form of an adamantane compound is reacted with a sulfonyl compound to obtain the adamantane derivative (II), which is then reacted with an alcohol to obtain the adamantane derivative (I). The adamantane derivative (I) and adamantane derivative (II) each having the structure represented by the general formula (I) and general formula (II), respectively, is a novel adamantyl (meth)acrylate compound and useful as a monomer for functional resins such as a photosensitive resin in the field of photolithography.Type: ApplicationFiled: February 2, 2009Publication date: June 18, 2009Applicant: Idemitsu Kosan Co., Ltd.Inventors: Naoyoshi HATAKEYAMA, Shinji Tanaka, Hidetoshi Ono, Yasunari Okada
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Patent number: 7534909Abstract: A (meth)acrylic ester compound represented by the general formula (1) and a dental material containing the compound, wherein, in the formula, R11 represents a divalent aromatic group; R12 represents a hydrogen atom or a methyl group; R13 represents an aryl group; R14 represents a hydrogen atom or a methyl group; and X11, represents an oxygen atom or a sulfur atom. A polymerizable composition containing the (meth)acrylic ester compound and an optical part obtained by polymerizing the polymerizable composition are also provided. The cured composition can provide advantageous physical and optical properties.Type: GrantFiled: May 21, 2004Date of Patent: May 19, 2009Assignee: Mitsui Chemicals, Inc.Inventors: Atsuo Otsuji, Masatoshi Takagi, Chojiro Higuchi, Akinori Nagatomo, Kouji Suesugi, Tetsuya Toida, Narimichi Honda
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Patent number: 7528279Abstract: The present invention provides an adamantane derivative (I) having a structure represented by the general formula (I); an adamantane derivative (II) having a structure represented by the general formula (II); and a process for producing those adamantane derivatives. An alcohol form of an adamantane compound is reacted with a sulfonyl compound to obtain the adamantane derivative (II), which is then reacted with an alcohol to obtain the adamantane derivative (I). The adamantane derivative (I) and adamantane derivative (II) each having the structure represented by the general formula (I) and general formula (II), respectively, is a novel adamantyl(meth)acrylate compound and useful as a monomer for functional resins such as a photosensitive resin in the field of photolithography.Type: GrantFiled: February 1, 2005Date of Patent: May 5, 2009Assignee: Idemitsu Kosan Co., Ltd.Inventors: Naoyoshi Hatakeyama, Shinji Tanaka, Hidetoshi Ono, Yasunari Okada
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Publication number: 20090099326Abstract: To provide a polymerizable group-containing and fluorine-containing adamantane derivative capable of affording a cured product having good heat resistance, good mechanical properties such as mar resistance and a low refractive index, a resin composition containing such a polymerizable group-containing adamantane derivative, and a fluorine-containing adamantane derivative which is useful as a reaction intermediate used for the production of the polymerizable group-containing and fluorine-containing adamantane derivative. Specifically provided are a fluorine-containing adamantane derivative represented by the general formula (I) below, a polymerizable group-containing and fluorine-containing adamantane derivative represented by the general formula (II) below, and a resin composition containing such a polymerizable group-containing and fluorine-containing adamantane derivative.Type: ApplicationFiled: April 20, 2007Publication date: April 16, 2009Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Yasunari Okada, Hideki Yamane, Hajime Ito, Nobuaki Matsumoto
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Publication number: 20090069521Abstract: A radiation-sensitive resin composition is provided which has high transparency to radiation, excelling in basic properties as a resist such as sensitivity, resolution, and pattern shape, and, in particular, a high resolution radiation-sensitive resin composition providing a wide DOF and excelling in LER. Also provided are a polymer which can be used in the composition and a novel compound useful for synthesizing the polymer. The novel compound is shown by the following formula (2), wherein R4 represents a methyl group, a trifluoromethyl group, or a hydrogen atom, at least one of the Rfs represents a fluorine atom or a linear or branched perfluoroalkyl group having 1 to 10 carbon atoms, A represents a divalent organic group or a single bond, G represents a divalent organic group having a fluorine atom or a single bond, Mm+ represents a metal ion or an onium cation, m represents an integer of 1 to 3, and p is an integer of 1 to 8.Type: ApplicationFiled: May 11, 2006Publication date: March 12, 2009Applicant: JSR CORPORATIONInventors: Tomoki Nagai, Eiji Yoneda, Takuma Ebata, Takanori Kawakami, Makoto Sugiura, Tsutomu Shimokawa, Makoto Shimizu
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Publication number: 20090061244Abstract: The invention is based on the discovery that certain polyether oligomers bearing curable moieties are useful as adhesives for the microelectonic packaging industry. Specifically, certain thermoset adhesive compositions containing polyether oligomers of the invention have good adhesion with lower viscosity, lower resistivity, higher conductivity and higher thixotropy when compared to acrylate- and maleimide-based thermoset adhesives.Type: ApplicationFiled: August 14, 2008Publication date: March 5, 2009Inventor: Stephen M. Dershem
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Patent number: 7473799Abstract: A process for the preparation of disubstituted adamantine derivatives characterized by the factor that the aromatic receptors can be a series of halide anisole, phenol, toluene, naphthalene, thiophene, or furan and their substituted derivatives. The synthesized disubstituted adamantine derivatives were subsequently converted into a new class of synthetic retinoids of pharmaceutical importance.Type: GrantFiled: January 29, 2007Date of Patent: January 6, 2009Assignee: Nanjing University of Aeronautics and AstronauticsInventors: Liqin Chen, Lei Tian, Xiaoquan Yao
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Patent number: 7456311Abstract: The invention provides a novel adamantane derivative useful as a monomer for producing functional resins such as photosensitive resins particularly for use in lithography, and a method for producing the derivative. The adamantane derivative has a structure represented by formula (I-a) and the method for producing the adamantane derivative employs a corresponding adamantane derivative serving as a starting material. In formula (I), R1 represents H, CH3, or CF3; R2a represents a C1 to C30 alkyl group or a hydrocarbon group containing a C3 to C30 cycloalkyl group or a C6 to C30 aryl group, the alkyl group or the hydrocarbon group having a hetero atom; each of X1 and X2 represents O or S; Y represents a C1 to C10 alkyl group, a halogen atom, OH, or SH, or two Ys are linked to form ?O or ?S; k represents an integer of 0 to 14; and each of m and n is an integer of 0 to 2.Type: GrantFiled: September 21, 2005Date of Patent: November 25, 2008Assignee: Idemitsu Kosan Co., Ltd.Inventors: Naoyoshi Hatakeyama, Shinji Tanaka
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Patent number: 7442828Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: August 24, 2007Date of Patent: October 28, 2008Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 7402698Abstract: The present invention is directed to secondary amino- and cycloamino-cycloalkanol derivatives, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.Type: GrantFiled: October 12, 2004Date of Patent: July 22, 2008Assignee: WyethInventors: Paige Erin Mahaney, Michael Byron Webb, Lori Krim Gavrin, Eugene John Trybulski
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Publication number: 20080166655Abstract: The present invention provides a polymer compound which can constitute a photoresist composition which is capable of having an excellent resolution, forming a fine pattern with a good rectangularity, obtaining favorable resist characteristics even when acid strength of a acid generated from an acid generator is weak, and having favorable sensitivity; a photoresist composition including the polymer compound; and a resist pattern formation method using the photoresist composition.Type: ApplicationFiled: January 28, 2005Publication date: July 10, 2008Inventors: Toshiyuki Ogata, Syogo Matsumaru, Yohei Kinoshita, Hideo Hada, Daiju Shiono, Hiroaki Shimizu, Naotaka Kubota
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Patent number: 7385079Abstract: A process for producing an ?-substituted acrylic norbornanyl compound represented by the formula [3] includes reacting an ?-substituted acrylic acid anhydride represented by the formula [1] with a substituted norbornanyl alcohol represented by the formula [2]. wherein R1 represents a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, or perfluoroethyl group, and wherein one of R2, R3 and R4 is a CF3C(CF3)(OH)CH2ā group, and each of the other two of R2, R3 and R4 is a hydrogen.Type: GrantFiled: November 24, 2004Date of Patent: June 10, 2008Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Shinya Akiba, Satoru Miyazawa, Takahisa Tada, Yusuke Kuramoto, Seiji Murata
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Patent number: 7378542Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: August 24, 2007Date of Patent: May 27, 2008Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 7332616Abstract: The present invention provides a polymer which has at least one or more of a repeating unit represented by a following general formula (1a), a repeating unit represented by a following general formula (2a) and a repeating unit represented by a following general formula (3b), and a repeating unit represented by a following general formula (1c), and a positive resist composition which contains as a base resin the polymer. Thereby, there can be provided a positive-resist composition having high sensitivity and high resolution in exposure with a high energy beam, wherein line edge roughness is small since swelling at the time of development is suppressed, and the residue after development is few.Type: GrantFiled: February 8, 2007Date of Patent: February 19, 2008Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai
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Patent number: 7321051Abstract: It is an object of the present invention to provide a vinyl ether group-containing (meth)acrylic ester, which has both radical polymerizability and cation polymerizability, improved in storage stability and stability in handling without impairing its polymerizability or, in other words, provide a stabilized vinyl ether group-containing (meth)acrylic ester. Another object is to provide a method of producing a stabilized vinyl ether group-containing (meth)acrylic ester composition. A further object is to provide a method of stably handing, a method of economically and stably producing and a method of purifying a vinyl ether group-containing (meth)acrylic ester.Type: GrantFiled: October 22, 2001Date of Patent: January 22, 2008Assignee: Nippon Shokubai Co., Ltd.Inventors: Keiji Yurugi, Hiroko Yamaguchi
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Patent number: 7297811Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: GrantFiled: December 4, 2003Date of Patent: November 20, 2007Assignee: International Business Machines CorporationInventors: Gregory Breyta, Richard Anthony DiPietro, Daniel Joseph Dawson
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Patent number: 7173147Abstract: A process for producing an acrylic ester compound includes reacting in the presence of alkene an alcohol represented by the formula (1), wherein R1 represents a hydrogen atom, a fluorine atom, a straight-chain or branched hydrocarbon group, a fluorine-containing alkyl group, or an aromatic or aliphatic ring and optionally contains oxygen, sulfur or a carbonyl bond, with an acid halide represented by the formula (2), wherein R2 represents a hydrogen atom, a halogen atom, a hydrocarbon group, or a fluorine-containing alkyl group, and X represents a halogen atom.Type: GrantFiled: November 24, 2004Date of Patent: February 6, 2007Assignee: Central Glass Company LimitedInventors: Satoru Miyazawa, Yusuke Kuramoto, Satoru Kobayashi, Kazuhiko Maeda
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Patent number: 7148363Abstract: An acrylate compound of formula (4): is produced by allowing an acrylic acid compound of formula (1): to react with an unsaturated compound of formula (2) or (3): In formulae (1) through (4), R1 and R2 are H or F, R3 is H, F, or an alkyl, alkenyl, fluoroalkyl or fluoroalkenyl group, R4 and R5 are H, halogen, or an alkyl, alkenyl, halogenated alkyl or halogenated alkenyl group; and X and Y are an unsubstituted or substituted hydrocarbon group, and dashed line - - - means that X and Y may be bonded together to form a cyclic structure.Type: GrantFiled: November 15, 2004Date of Patent: December 12, 2006Assignee: Tosoh CorporationInventors: Shinichi Ishikawa, Hisao Eguchi
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Patent number: 7135595Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.Type: GrantFiled: January 12, 2006Date of Patent: November 14, 2006Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
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Patent number: 7128926Abstract: It is an object of the present invention to provide a novel ester compound and the use thereof as a sex attractant.Type: GrantFiled: November 11, 2003Date of Patent: October 31, 2006Assignee: Incorporated Administrative Agency, National Agriculture and Bio-Oriented Research OrganizationInventor: Tomonori Arai
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Patent number: 7087696Abstract: Epoxy acrylates of the formulae (A), (B) and epoxy acrylate mixtures comprising at least one of the compounds (A) or (B) are novel and find use in coating materials or adhesives featuring high UV stabilityType: GrantFiled: December 18, 2003Date of Patent: August 8, 2006Assignee: Huntsman Advanced Materials Americas Inc.Inventors: Rolf Wiesendanger, Michael Reisinger
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Patent number: 7078562Abstract: The adamantane derivatives of the present invention which are represented by the general formula (1): wherein X is a hydrogen atom, alkyl, halogen-containing alkyl, halogen, or hydroxyl-, halogen-, nitrile- or ether-containing hydrocarbyl, and a plurality of X groups, if any, may be the same or different from each other; n1 is an integer of 1 to 14; R1 to R4 may be the same or different from each other and are independently alkyl or halogen-containing alkyl; and Y1 and Y2 may be the same or different from each other and are independently a hydrogen atom or a group represented by the general formula (2): wherein R5 to R7 may be the same or different from each other and are independently a hydrogen atom, alkyl, halogen or halogen-containing alkyl, are excellent in optical properties, heat resistance and acid-dissociating property, and useful as crosslinking-type resins, optical materials such as optical fibers, light wave guides, optical disk substrates and photoresists as well as raw materials thereofType: GrantFiled: January 11, 2005Date of Patent: July 18, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kikuo Furukawa, Minoru Kakuda, Yoshio Nishimura, Toshiaki Yamada
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Patent number: 7071352Abstract: A magnesium halide salt of a 2-alkyl-2-adamantanol is reacted with a carboxylic acid halide such as acrylic chloride or the like in the presence of a tertiary amine to produce a 2-alkyl-2-adamantyl ester (the first invention). A 2-alkyl-2-adamantanol is reacted with a carboxylic acid such as acrylic acid or the like in the presence of an acid catalyst such as concentrated sulfuric acid or the like and a drying agent composed of an acidic or neutral inorganic compound (e.g. magnesium sulfate) which is a solid at ordinary temperature in a dried state or of a water-absorbing high-molecular compound, to produce a 2-alkyl-2-admantyl ester (the second invention). The above ester is important as a raw material for a resist for semiconductor production.Type: GrantFiled: July 18, 2001Date of Patent: July 4, 2006Assignee: Tokuyama CorporationInventors: Masao Yamaguchi, Yoshihiro Hirota, Hiromasa Yamamoto
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Patent number: 7067692Abstract: In the present invention, an adamantyl acrylate compound is produced by a process comprising a first step and a second step without using acid halide. In the first step, a 2-adamantanone compound is reacted with a hydrocarbyl halide in the presence of lithium metal to form an adamantanolate intermediate that is then reacted with an acrylic ester compound in the second step to produce the aimed adamantyl acrylate compound.Type: GrantFiled: April 16, 2004Date of Patent: June 27, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kikuo Furukawa, Minoru Kakuda, Yoshio Nishimura, Takehiko Isobe, Mitsuharu Suzuki
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Patent number: 7049462Abstract: It is an object of the present invention to provide a production method of a dehydration reaction product by which the occurrence of troubles in the production step or the degradation in performance characteristics or quality of various chemical products can be suppressed to a satisfactory extent. A production method of a dehydration reaction product which comprises a dehydration reaction step of subjecting a reaction solution containing a polymerizable compound to the dehydration reaction, said dehydration reaction step comprising using a dehydration reaction apparatus, said dehydration reaction apparatus comprising a reaction vessel, a condenser and a connecting pipe joining said reaction vessel with said condenser and satisfying the requirement: 0.05<(B3/A)<35 where A is a capacity (m3) of said reaction vessel and B is a total length (m) of said connecting pipe on the horizontal basis.Type: GrantFiled: November 27, 2001Date of Patent: May 23, 2006Assignee: Nippon Shokubai Co., Ltd.Inventors: Koichiro Nagare, Toru Uno, Yoshiyuki Onda, Tsutomu Yuasa, Masato Nishiue, Hisamoto Kawano
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Patent number: 7026504Abstract: There is provided a method for obtaining a high-purity alkyladamantyl ester from an alkyladamantyl ester composition containing a large quantity of alkyladamantyl halide obtained by, for example, alkylating raw material 2-adamantanone obtained through oxidation of adamantane by use of an organic metal reagent and then causing an acid halide to react with the resulting product, efficiently by a simple process. To an alkyladamantyl ester composition containing an alkyladamantyl halide such as 2-chloro-2-methyladamantane in an amount of larger than 0.5 parts by weight based on 100 parts by weight of alkyladamantyl ester such as 2-methyl-2-adamantyl methacrylate, a mixed solution of, for example, methanol and a sodium hydroxide aqueous solution is added. By bringing the alkali compound into contact with the alkyladamantyl halide in a homogeneous system so as to convert the halide into a compound which produces no acid when heated, the amount of the alkyladamantyl halide in the composition is reduced to 0.Type: GrantFiled: January 26, 2001Date of Patent: April 11, 2006Assignee: Tokuyama CorporationInventors: Masao Yamaguchi, Hiromasa Yamamoto, Hideki Kikuchi, Yoshihiro Hirota
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Patent number: 7012123Abstract: An acrylic polymer suitable for use as a charge transport material, the acrylic polymer containing pendant ?-conjugated groups represented by the following general formula (1) and having a triad syndiotacticity or triad isotacticity of at least 60%: wherein in the formula (1), Ar represents an aromatic group, R1 represents hydrogen or a methyl group, R2 represents an organic group or none, R3 and R4 both represent hydrogen or at least one of them represents an electron-donating or electron-withdrawing group, and n denotes an integer of 2 or larger.Type: GrantFiled: April 24, 2003Date of Patent: March 14, 2006Assignee: Sekisvi Chemical Co., Ltd.Inventors: Hideaki Ishizawa, Tamaki Nakano
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Patent number: 6858760Abstract: A fluorine-containing cyclic compound is represented by the formula 1: wherein each of R1, R2 and R3 independently represents a hydrogen, alkyl group, fluorine, fluoroalkyl group or hexafluorocarbinol group, wherein at least one of the hexafluorocarbinol groups may partly or totally be protected with a protecting group, and wherein the protecting group is (a) a straight-chain, branched or cyclic hydrocarbon group having a carbon atom number of 1-25 or (b) an aromatic hydrocarbon group and optionally contains a fluorine atom, oxygen atom, nitrogen atom or carbonyl bond.Type: GrantFiled: February 20, 2004Date of Patent: February 22, 2005Assignee: Central Glass Company, LimitedInventors: Haruhiko Komoriya, Satoru Miyazawa, Katsunori Kawamura, Satoru Kobayashi, Kazuhiko Maeda
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Patent number: 6846949Abstract: The invention discloses a novel ester compound of an unsaturated carboxylic acid represented by the general formula in which R1 is preferably a hydrogen atom or methyl group, R2 is preferably a trifluoromethyl group, R3 is a non-aromatic polycyclic hydrocarbon group or, preferably, an adamantyl group and R4 is preferably a hydrogen atom or methyl group. This unsaturated ester compound is polymerizable to give a (co)polymeric resin which can be used as a base resinous ingredient in a photoresist composition for light exposure with ultraviolet light of a very short wavelength by virtue of the high transparency to the short-wavelength light. A synthetic method for the preparation of the novel ester compound is disclosed.Type: GrantFiled: December 11, 2003Date of Patent: January 25, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Toshiyuki Ogata, Kotaro Endo, Hiroshi Komano
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Patent number: 6833462Abstract: An acrylate compound of formula (4): is produced by allowing an acrylic acid compound of formula (1): to react with an unsaturated compound of formula (2) or (3): In formulae (1) through (4), R1 and R2 are H or F, R3 is H, F, or an alkyl, alkenyl, fluoroalkyl or fluoroalkenyl group, R4 and R5 are H, halogen, or an alkyl, alkenyl, halogenated alkyl or halogenated alkenyl group; and X and Y are an unsubstituted or substituted hydrocarbon group, and dashed line - - - means that X and Y may be bonded together to form a cyclic structure.Type: GrantFiled: November 26, 2002Date of Patent: December 21, 2004Assignee: Tosoh CorporationInventors: Shinichi Ishikawa, Hisao Eguchi
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Publication number: 20040210082Abstract: In the present invention, an adamantyl acrylate compound is produced by a process comprising a first step and a second step without using acid halide. In the first step, a 2-adamantanone compound is reacted with a hydrocarbyl halide in the presence of lithium metal to form an adamantanolate intermediate that is then reacted with an acrylic ester compound in the second step to produce the aimed adamantyl acrylate compound.Type: ApplicationFiled: April 16, 2004Publication date: October 21, 2004Inventors: Kikuo Furukawa, Minoru Kakuda, Yoshio Nishimura, Takehiko Isobe, Mitsuharu Suzuki
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Patent number: 6784312Abstract: The present invention relates to a polymerizable monomer represented by the general formula (1), wherein R1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group; R2 is a straight-chain or branched alkyl group, a cyclic alkyl group, an aromatic group, or a substituent having at least two of these groups, the R2 being optionally partially fluorinated; R3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, the R3 optionally containing a bond of an oxygen atom or carbonyl group; and n is an integer of 1-2.Type: GrantFiled: July 19, 2002Date of Patent: August 31, 2004Assignees: Central Glass Company, Limited, F-Tech, Inc.Inventors: Satoru Miyazawa, Kazuhiko Maeda, Kenji Tokuhisa, Shoji Arai
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Patent number: 6770777Abstract: This invention discloses a process for preparing an 2-alkyl-2-adamantyl ester comprising the steps of combining a solution or suspension of 2-adamantanone and an alkyl halide with lithium metal for reacting them to generate an lithium 2-alkyl-2-adamantyl alcoholate, and then reacting the lithium 2-alkyl-2-adamantyl alcoholate with an acid halide.Type: GrantFiled: November 18, 2002Date of Patent: August 3, 2004Assignee: Tokuyama CorporationInventors: Masao Yamaguchi, Hideki Kikuchi, Yoshihiro Hirota
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Publication number: 20040082724Abstract: In accordance with the present invention, there are provided novel heterobifunctional monomers and users for the same. Invention compounds have many of the properties required by the microelectronics industry, such as, for example, hydrophobicity, high Tg values, low dielectric constant, ionic purity, low coefficient of thermal expansion (CTE), and the like. These properties result in a thermoset that is particularly well suited to high performance applications where typical operating temperatures are often significantly higher than those at which prior art materials were suitable. Invention compounds are particularly ideal for use in the manufacture of electronic components, such as, for example, printed circuit boards, and the like.Type: ApplicationFiled: July 1, 2003Publication date: April 29, 2004Applicant: Henkel Loctite CorporationInventors: Stephen M. Dershem, Kevin J. Forrestal, Puwei Liu
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Publication number: 20040077898Abstract: There is provided a method for obtaining a high-purity alkyladamantyl ester from an alkyladamantyl ester composition containing a large quantity of alkyladamantyl halide obtained by, for example, alkylating raw material 2-adamantanone obtained through oxidation of adamantane by use of an organic metal reagent and then causing an acid halide to react with the resulting product, efficiently by a simple process.Type: ApplicationFiled: July 25, 2003Publication date: April 22, 2004Inventors: Masao Yamaguchi, Hiromasa Yamamoto, Hideki Kikuchi, Yoshihiro Hirota
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Patent number: 6696595Abstract: There is provided a method for obtaining an alkyladamantyl ester efficiently by distilling and purifying a crude alkyladamantyl ester containing impurities which decompose the alkyladamantyl ester without decomposing the alkyladamantyl ester. The crude alkyladamantyl ester such as crude 2-methyl-2-adamantyl methacrylate is distilled in the presence of a heterocyclic compound and/or a basic compound such as 3-ethyl-3-hydroxymethyloxetane or diglycidyl bisphenol A.Type: GrantFiled: November 22, 2002Date of Patent: February 24, 2004Assignee: Tokuyama CorporationInventors: Hiromasa Yamamoto, Masao Yamaguchi, Yoshihiro Hirota, Takashi Kobayakawa
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Publication number: 20040024241Abstract: The invention relates to a method for producing (meth)acrylic acid esters by transesterification of the (meth)acrylic acid with a higher alkanol in the presence of an acid catalyst, at least one polymerization inhibitor and one organic solvent that forms an azeotropic mixture with water. The reaction mixture is heated to the boiling point of the mixture in a reactor that comprises a distillation unit with a column and a condenser. The content of the reactor is recirculated via an external evaporator and heated to the boiling point, and the azeotropic mixture is distilled off. The organic solvent forms a reflux and at least a part of the solvent reflux is recirculated between the reactor and the evaporator. The inventive method allows for the production of higher (meth)acrylic acid esters in a reactor with a circulation evaporator without using copper salts as the polymerization inhibitors.Type: ApplicationFiled: June 18, 2003Publication date: February 5, 2004Inventors: Friedrich-Georg Martin, Gerhard Nestler, Jurgen Schroder
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Publication number: 20040015008Abstract: The present invention discloses an adamantyl ester monomer composition characterized by containing at least an adamantyl ester monomer having at least one polymerizable unsaturated bond in the molecule, and a compound represented by the following general formula (1): 1Type: ApplicationFiled: February 3, 2003Publication date: January 22, 2004Inventors: Hiromasa Yamamoto, Masao Yamaguchi, Yoshihito Hirota
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Publication number: 20030229234Abstract: The present invention discloses a compound having the following formula (I), 1Type: ApplicationFiled: May 28, 2002Publication date: December 11, 2003Applicant: Everlight USA, Inc.Inventors: Chi-Sheng Chen, Yen-Cheng Li, Meng-Hsum Cheng