Halogen In Acid Moiety Patents (Class 560/219)
-
Patent number: 9023581Abstract: A resist composition which can form a very fine resist pattern with excellent lithography properties, a new polymeric compound useful for the resist composition, and a compound useful as a monomer for the polymeric compound. The resist composition contains a polymeric compound containing a structural unit (a0) represented by general formula (a0) shown below. In the formula (a0), A is an anion represented by the general formula (1) or (2).Type: GrantFiled: June 14, 2011Date of Patent: May 5, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Akiya Kawaue, Kazushige Dohtani, Yoshiyuki Utsumi, Jun Iwashita, Kenri Konno, Daiju Shiono, Daichi Takaki
-
Patent number: 8791293Abstract: According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3). In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which “a moiety capable of changing its developer solubility by the action of an acid” and “a moiety having a photoacid generating function” are arranged with regularity.Type: GrantFiled: August 2, 2012Date of Patent: July 29, 2014Assignee: Central Glass Company, LimitedInventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
-
Publication number: 20140199631Abstract: A polymer for resist use is obtainable from a monomer having formula (1) wherein R1 is H, CH3 or CF3 and R2 is H or an acid labile group. A resist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.Type: ApplicationFiled: December 17, 2013Publication date: July 17, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Masayoshi Sagehashi, Koji Hasegawa, Kazuhiro Katayama
-
Publication number: 20140186769Abstract: A resist composition having excellent lithography properties, which generates an acid upon exposure and exhibits changed solubility in a developing solution by the action of an acid, the resist composition containing a base material component (A) which exhibits changed solubility in a developing solution by the action of an acid, and the base material component (A) containing a high-molecular weight compound (A1) having a constituent unit (a0) derived from a compound represented by the following general formula (a0-1); a method for forming a resist pattern using the resist composition; and a high-molecular weight compound (A1) having a constituent unit (a0) derived from a compound represented by the following general formula (a0-1), are disclosed.Type: ApplicationFiled: December 10, 2013Publication date: July 3, 2014Applicant: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takaaki Kaiho, Yoshiyuki Utsumi, Jun Iwashita, Masahito Yahagi
-
Publication number: 20140147481Abstract: The invention provides novel compositions based on a structure designated as “Honaucin A”, including Honaucin A variants and analogs, and pharmaceutical compositions, liposomes and nanoparticles comprising them, and methods of making and using them. In one embodiment these Honaucin A compounds, and variants and analogs thereof are used to ameliorate (including to treat or prevent) inflammation. In one embodiment, these Honaucin A compounds, and variants and analogs thereof are used to ameliorate (including to treat or prevent) inflammation. In one embodiment, these Honaucin A compounds, and variants and analogs thereof are used as bacterial quorumsensing inhibitors. Accordingly, in alternative embodiments the compositions of the invention are used as anti-bacterial agents.Type: ApplicationFiled: June 3, 2011Publication date: May 29, 2014Applicants: UNIVERSITY OF RHODE ISLAND RESEARCH FOUNDATION, THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: William Gerwick, Lena Gerwick, Huykjae Choi, Francisco Villa, Jennifer Smith, David C Rowley
-
Patent number: 8697903Abstract: A fluorinated ester monomer is provided having formula (1) wherein R1 is H, CH3 or CF3, R2 and R3 are H or a monovalent hydrocarbon group, or R2 and R3 forms a hydrocarbon ring, R4 is a monovalent hydrocarbon group, and k is 0 or 1. A polymer obtained from the monomer has transparency to radiation with a wavelength of up to 200 nm and appropriate alkaline hydrolysis, is constructed such that any of water repellency, water slip and surface segregation may be adjusted by a choice of its structure, and is useful in forming ArF immersion lithography materials.Type: GrantFiled: September 22, 2011Date of Patent: April 15, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Yuuki Suka, Yuji Harada, Koji Hasegawa, Takeshi Sasami
-
Sulfonium salt, polymer, method for producing the polymer, resist composition and patterning process
Patent number: 8691490Abstract: There is disclosed a sulfonium salt represented by the following general formula (1). In the formula, X and Y each represents a group having a polymerizable functional group; Z represents a divalent hydrocarbon group having 1 to 33 carbon atoms optionally containing a hetero atom; R1 represents a divalent hydrocarbon group having 1 to 36 carbon atoms optionally containing a hetero atom; and R2 and R3 each represents a monovalent hydrocarbon group having 1 to 30 carbon atoms optionally containing a hetero atom or R2 and R3 may be bonded with each other to form a ring together with a sulfur atom in the formula. There can be provided a sulfonium salt usable as a resist composition providing high resolution and excellent in LER in photolithography using a high energy beam such as an ArF excimer laser, an EUV light and an electron beam as a light source, a polymer obtained from the sulfonium salt, a resist composition containing the polymer and a patterning process using the resist composition.Type: GrantFiled: January 25, 2011Date of Patent: April 8, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Satoshi Watanabe, Youichi Ohsawa, Keiichi Masunaga, Takeshi Kinsho -
Patent number: 8592622Abstract: A polymerizable fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R2, R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.Type: GrantFiled: January 4, 2011Date of Patent: November 26, 2013Assignee: Central Glass Company, LimitedInventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka
-
Patent number: 8558024Abstract: To provide a fluorinated compound having an RF group with at most 6 carbon atoms, whereby a fluorinated polymer having a highly durable water/oil repellency can be produced, and an environmental load is little, and a fluorinated polymer having a highly durable water/oil repellency and presenting little environmental load, obtainable by polymerizing such a fluorinated compound. A fluorinated compound represented by the following formula (I) and its polymer: CH2?C(M)COO(CH2)nPhXPhZCrF2r+1??(I) (in the formula (I), M is a hydrogen atom, a methyl group or a halogen atom, n is an integer of from 0 to 2, Ph is a phenylene group, X is CH2O or OCH2, Z is a single bond, a C1-4 alkylene group containing an etheric oxygen atom, or COO(CH2)m (wherein m is an integer of from 1 to 4), and r is an integer of from 1 to 6).Type: GrantFiled: March 30, 2012Date of Patent: October 15, 2013Assignee: Asahi Glass Company, LimitedInventor: Taiki Hoshino
-
Patent number: 8530692Abstract: A compound has a following general formula (1). R0 represents an (n+1)-valent linear or branched aliphatic hydrocarbon group having 1 to 10 carbon atoms, or the like. R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group. R2 represents a single bond or the like. R3 represent a linear or branched alkyl group having 1 to 4 carbon atoms or the like. X represents a linear or branched fluoroalkylene group having 1 to 10 carbon atoms, and n is an integer from 1 to 5.Type: GrantFiled: August 23, 2011Date of Patent: September 10, 2013Assignee: JSR CorporationInventors: Nobuji Matsumura, Yuusuke Asano, Hirokazu Sakakibara, Yukio Nishimura, Takehiko Naruoka
-
Patent number: 8524941Abstract: According to the present invention, an ?-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an ?-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the ?-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the ?-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the ?-substituted acrylic acid.Type: GrantFiled: April 26, 2010Date of Patent: September 3, 2013Assignee: Central Glass Company, LimitedInventors: Shinya Akiba, Ryo Nadano, Yutaka Katsuhara
-
Patent number: 8519073Abstract: A compound represented by general formula (I); and a polymeric compound including a structural unit (a1) represented by general formula (II). wherein R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; each of R1 to R3 independently represents an alkyl group or a fluorinated alkyl group, with the provision that no fluorine atom is bonded to a carbon atom adjacent to the tertiary carbon atom to which R1 to R3 are bonded, and at least one of R1 to R3 represents a fluorinated alkyl group; and R2 and R3 may form a ring structure.Type: GrantFiled: October 15, 2007Date of Patent: August 27, 2013Assignees: Tokyo Ohka Kogyo Co., Ltd., Daito Chemix CorporationInventors: Yoshiyuki Utsumi, Hiroaki Shimizu, Kyoko Ohshita, Toshiharu Shimamaki, Kenshin Niwa, Seihin Shu
-
Publication number: 20130209935Abstract: A polymer is prepared from an adamantane methacrylate monomer whose alcoholic hydroxyl group is protected with an alicyclic-containing tertiary alkyl group. A photoresist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.Type: ApplicationFiled: February 8, 2013Publication date: August 15, 2013Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventor: SHIN-ETSU CHEMICAL CO., LTD.
-
Publication number: 20130184469Abstract: The invention relates to a novel, industrially viable, cost effective process for the preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide commonly known as Rufinamide and intermediates thereof.Type: ApplicationFiled: August 23, 2011Publication date: July 18, 2013Inventors: Ramamohan Rao Davuluri, Ravi Ponnaiah, Sanjay Kumar Dehury, Selvaraju K., Deepthi VPSS, Dhanunjaya Naidu
-
Patent number: 8273837Abstract: A radiation-sensitive resin composition which has high transparency to radiation, excelling in basic properties as a resist such as sensitivity, resolution, and pattern shape, and, in particular, exhibiting high resolution performance, excellent DOF and LER, and high resistance to a liquid medium used in liquid immersion lithography is provided. Also provided are a polymer which can be used in the composition, a novel compound useful for synthesizing the polymer, and a method of producing the composition.Type: GrantFiled: December 13, 2006Date of Patent: September 25, 2012Assignee: JSR CorporationInventors: Tomoki Nagai, Takuma Ebata, Nobuji Matsumura
-
Patent number: 8212065Abstract: A method for the production of optically active ?-alkylcarbonyl compounds with retention of the stereo information of the starting compound. The starting compound used here is a carbonyl compound which has, in the ?-position, a leaving group which is substituted by an alkyl group with inversion of the configuration. The substitution of the leaving group is effected with the use of an alkylmagnesium Grignard and a zinc (II) salt or a zinc organyl. The method permits the production of optically active ?-alkylcarbonyl compounds at very mild temperatures (for example 0° C.) with the use of starting compounds which are easy to prepare and economical and nontoxic catalysts, it also being possible to achieve a very high yield.Type: GrantFiled: September 18, 2008Date of Patent: July 3, 2012Assignee: Albert-Ludwigs-Universitat FreiburgInventors: Bernhard Breit, Christopher Studte
-
Patent number: 8212064Abstract: An oligomer of the formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]mG??(I) wherein G is an I; OH; OC(O)CH?CH2; OC(O)CCH3?CH2; OC(O)CCl?CH2; NR1H; N3; NCO; SQ wherein Q is H, alkyl, (CH2)nOH, (CH2)nNH2, (CH2)nOC(O)C(Me)=CH2, or (CH2)nNHC(O)C(Me)=CH2; SCN; COOH; SO3H; NHCOCH?CH2; NHCOC(CH3)?CH2); OC(O)NHCH2CH2OC(O)C(CH3)?CH2; or OC(O)NHCH2CH2OC(O)C(CH3)?CH2; subscript n is an integer from 1 to about 6, subscript x is an integer from 1 to about 6, subscripts y, z and m are each independently 1, 2 or 3, or a mixture thereof, the total number of carbons in said formula (I) excluding G ranges from about 8 to about 22, and a process for preparation thereof.Type: GrantFiled: May 14, 2008Date of Patent: July 3, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
-
Patent number: 8153756Abstract: Disclosed is a fluorine-containing polymer having: (A) a repeating unit derived from a fluorine-containing monomer which is represented by the following formula: CH2?C(—X)—C(?O)—Y—[—(CH2)m—Z—]p—(CH2)n—Rf??(I) (B) a repeating unit derived from a monomer containing no fluorine atom, and if necessary (C) a repeating unit derived from a crosslinkable monomer. This fluorine containing polymer has excellent water repellency, oil repellency and antifouling property.Type: GrantFiled: September 23, 2008Date of Patent: April 10, 2012Assignee: Daikin Industries, Ltd.Inventors: Ikuo Yamamoto, Yutaka Ohira, Yoshio Funakoshi, Shinichi Minami, Ginjiro Tomizawa
-
Patent number: 8134033Abstract: To provide a novel polymerizable fluorocompound having a highly fluorinated norbornane structure, and a polymer obtained from the compound. Further, their production processes and a novel intermediate useful for the processes. A novel compound (1) such as a compound (11) or a compound (12), and its polymer. A compound (2) such as a compound (21) or (22), and a compound (3) such as a compound (31) or (32M), which are useful as an intermediate for the production of the compound (1), and its production process. However, each of ZA to ZE represents such as —CH(—OC(O)C(CH3)?CH2)— or —CF2, Each of WA and WB represents such as F, each of YA to YE represents such as —CH(—OH)— or —CF(CH2OH), and each of XA to XE represents such as —C(O)— or —CF2—.Type: GrantFiled: January 12, 2009Date of Patent: March 13, 2012Assignee: Asahi Glass Company, LimitedInventors: Yasuhisa Matsukawa, Daisuke Shirakawa, Eisuke Murotani, Naoko Shirota, Yoko Takebe
-
Publication number: 20120004444Abstract: According to the present invention, an ?-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an ?-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the ?-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the ?-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the ?-substituted acrylic acid.Type: ApplicationFiled: April 26, 2010Publication date: January 5, 2012Applicant: Central Glass Company, LimitedInventors: Shinya Akiba, Ryo Nadano, Yutaka Katsuhara
-
Patent number: 8053165Abstract: 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: GrantFiled: March 17, 2009Date of Patent: November 8, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Masaki Ohashi, Koji Hasegawa, Takeru Watanabe
-
Publication number: 20110236831Abstract: The invention provides an acetal compound containing an adamantane ring having an alcoholic hydroxyl group which is protected with an acetal group having a carbonyl moiety of branched structure. A photoresist film comprising a polymer comprising recurring units derived from the acetal compound and an acid generator is characterized by a high dissolution contrast when it is subjected to exposure and organic solvent development to form an image via positive/negative reversal.Type: ApplicationFiled: March 23, 2011Publication date: September 29, 2011Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Koji HASEGAWA, Jun HATAKEYAMA, Takeshi NAGATA, Seiichiro TACHIBANA, Takeshi KINSHO
-
Publication number: 20110196121Abstract: A fluorine-containing compound represented by the formula 1, where R1 is a methyl group or trifluoromethyl group, each of R2 and R3 is independently a hydrogen atom or a group containing (a) a hydrocarbon group having a straight-chain, branched or ring form and having a carbon atom number of 1-25 or (b) an aromatic hydrocarbon group, the group optionally containing at least one of a fluorine atom, an oxygen atom and a carbonyl bond, l is an integer of from 0 to 2, each of m and n is independently an integer of 1-5 to satisfy an expression of m+n?6, and when at least one of R1, R2 and R3 is in a plural number, the at least one of R1, R2 and R3 may be identical with or different from each other.Type: ApplicationFiled: April 26, 2011Publication date: August 11, 2011Applicant: Central Glass Company, LimitedInventors: Shinichi SUMIDA, Haruhiko Komoriya, Kazuhiko Maeda
-
Publication number: 20100297564Abstract: A polymerizable fluorine-containing monomer and a fluorine-containing polymer which are suitable for a resist layer and a protective layer of a laminated resist for forming a fine pattern in production of semiconductor devices, and further are useful especially in immersion lithography using water as a liquid medium, and a method of forming a resist pattern are provided. The polymerizable fluorine-containing monomer is represented by the formula (1): wherein R1 is hydrogen atom or a monovalent saturated or unsaturated hydrocarbon group of 1 to 15 carbon atoms, and the hydrocarbon group may be chain or cyclic structure and may have oxygen atom, nitrogen atom, sulfur atom or halogen atom, the polymer is a homopolymer or copolymer of the monomer, and the method of forming a resist pattern using such a homopolymer or copolymer is carried out by immersion lithography.Type: ApplicationFiled: December 22, 2008Publication date: November 25, 2010Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Tsuneo Yamashita, Yosuke Kishikawa, Yoshito Tanaka, Masamichi Morita
-
Patent number: 7825275Abstract: 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 —C(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: GrantFiled: September 28, 2009Date of Patent: November 2, 2010Assignee: Asahi Glass Company, LimitedInventors: Koichi Murata, Naoko Shirota, Osamu Yokokoji, Yoko Takebe
-
Patent number: 7750178Abstract: The present invention relates to a polymerizable acrylate compound represented by the general formula (1): (in the formula, R1 represents a hydrogen atom, halogen atom, hydrocarbon group or fluorine-containing alkyl group, R2 and R3 may be different or identical, and each of them independently is a hydrogen atom, fluorine atom, hydrocarbon group optionally branched, fluorine-containing alkyl group, aromatic group, or cyclic structure containing an aliphatic group and may contain oxygen or carbonyl bond) and a polymer compound obtained by using the same.Type: GrantFiled: February 5, 2004Date of Patent: July 6, 2010Assignee: Central Glass Company, LimitedInventors: Satoru Miyazawa, Satoru Kobayashi, Takeo Komata, Kei Matsunaga
-
Publication number: 20090287010Abstract: An oligomer of the formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]mG??(I) wherein G is an I; OH; OC(O)CH?CH2; OC(O)CCH3?CH2; OC(O)CCl?CH2; NR1H; N3; NCO; SQ wherein Q is H, alkyl, (CH2)nOH, (CH2)nNH2, (CH2)nOC(O)C(Me)?CH2, or (CH2)nNHC(O)C(Me)?CH2; SCN; COOH; SO3H; NHCOCH?CH2; NHCOC(CH3)?CH2); OC(O)NHCH2CH2OC(O)C(CH3)?CH2; or OC(O)NHCH2CH2OC(O)C(CH3)?CH2; subscript n is an integer from 1 to about 6, subscript x is an integer from 1 to about 6, subscripts y, z and m are each independently 1, 2 or 3, or a mixture thereof, the total number of carbons in said formula (I) excluding G ranges from about 8 to about 22, and a process for preparation thereof.Type: ApplicationFiled: May 14, 2008Publication date: November 19, 2009Applicant: E.I. du Pont de Nemours and CompanyInventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
-
Publication number: 20090221702Abstract: The present invention provides the use of a compound of the Formula: (I) wherein R1 is C1-5 alkoxy, OCOC1-3Alkyl, O(CH2)2O(CH2)2O(CH2)2OMe, O(CH2)2O(CH2)2O(CH2)2OH or OH; R2 is H, (CH2)nOH, OCH3, Hal or (II) or (III) R3 is H or (CH2)nOH; and R4 is C1-6 alkyl, optionally substituted by one or more of Hal, OH, COCH3, NH2, NHCH3, NHMe, NMe2, OCOCH3, CO2H or esters or amides thereof where n is 1-5; and pharmaceutically acceptable salts thereof, in the manufacture of a medicament for use in modulating PKB activity.Type: ApplicationFiled: March 17, 2006Publication date: September 3, 2009Inventors: Rudiger Woscholski, Helen Hailes, Macba Numbere, Erika Rosivatz
-
Publication number: 20090221845Abstract: To provide a fluoropolymer having functional groups and having high transparency in a wide wavelength region, and a resist composition comprising the fluoropolymer. A fluoropolymer (A) having monomer units formed by polymerization of a fluorinated diene represented by the following formula (1): CF2?CFCH2CH-Q-CH2CH?CH2??(1) wherein Q is (CH2)aC(CF3)2OR4 (wherein a is an integer of from 0 to 3, R4 is an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms which may have an etheric oxygen atom, an alkoxycarbonyl group having at most 6 carbon atoms, or CH2R5 (wherein R5 is an alkoxycarbonyl group having at most 6 carbon atoms)), or (CH2)dCOOR6 (wherein d is 0 or 1, and R6 is a hydrogen atom, or an alkyl group or a fluorinated alkyl group having at most 20 carbon atoms), a process for its production and a resist composition having the fluoropolymer (A) as a base.Type: ApplicationFiled: April 17, 2009Publication date: September 3, 2009Applicant: Asahi Glass Company, LimitedInventors: Yoko Takebe, Isamu Kaneko
-
Patent number: 7550626Abstract: A process for preparing racemic alkyl-5-halopent-4-enecarboxylic acids and esters thereof of the formula (I), in which R is a C1-C6-alkyl radical, R1 is H or C1-4-alkyl and X is chlorine, bromine or iodine, which comprises a) reacting a dialkyl alkylmalonate of the formula (II),in which R is as defined above and R2 is a C1-C4-alkyl radical, in the presence of a metal alkoxide of the formula MOR3, in which M may be Na, K or Li, and R3 is a C1-C4-alkyl radical, and in an organic solvent, with 1,3-dihalopropene to give the corresponding allylated malonate, then b) after full conversion, adding an inorganic salt and a C1-C6 alcohol to the reaction mixture, heating the reaction mixture to reflux temperature, then c) isolating the desired racemic ester of the formula (I) from the reaction mixture by extraction or direct distillation and d) if the racemic acid is the desired end product, hydrolyzing the ester function.Type: GrantFiled: July 3, 2006Date of Patent: June 23, 2009Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KGInventors: Peter Pojarliev, Gerhard Steinbauer, Christian Burger
-
Patent number: 7442829Abstract: Disclosed is a fluorine-containing polymer having: (A) a repeating unit derived from a fluorine-containing monomer which is represented by the following formula: CH2?C(—X)—C(?O)—Y—[—(CH2)m-Z-]p—(CH2)n—Rf ??(I) (B) a repeating unit derived from a monomer containing no fluorine atom, and if necessary (C) a repeating unit derived from a crosslinkable monomer. This fluorine containing polymer has excellent water repellency, oil repellency and antifouling property.Type: GrantFiled: March 25, 2005Date of Patent: October 28, 2008Assignee: Daikin Industries, Ltd.Inventors: Ikuo Yamamoto, Yutaka Ohira, Yoshio Funakoshi, Shinichi Minami, Ginjiro Tomizawa
-
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
-
Publication number: 20080255385Abstract: To provide a method for producing an optically active (4E)-5-chloro-2-isopropyl-4-pentenoic acid, a basic amino acid salt thereof or an optically active (4E)-5-chloro-2-isopropyl-4-pentenoic acid ester with high yield and high optical purity by simple operation. An optically active (4E)-5-chloro-2-isopropyl-4-pentenoic acid is obtained by precipitating a basic amino acid salt of optically active (4E)-5-chloro-2-isopropyl-4-pentenoic acid from a solvent solution containing an optical isomer mixture of (4E)-5-chloro-2-isopropyl-4-pentenoic acid and an optically active basic amino acid or a salt thereof, and then the basic amino acid salt of optically active (4E)-5-chloro-2-isopropyl-4-pentenoic acid is subjected to a desalting reaction. Further, an esterification reaction is carried out to obtain an optically active (4E)-5-chloro-2-isopropyl-4-pentenoic acid ester.Type: ApplicationFiled: June 16, 2008Publication date: October 16, 2008Applicant: Asahi Glass Company, LimtedInventors: Mayumi Makino, Kazuhisa Sakata, Yasushi Matsumura
-
Patent number: 7423170Abstract: Oncoproteins such as Ras and RhoB are known to induce cell division in an unrestrained manner when such proteins are localized at the inner surface of a cancer cell membrane. The localization is effected by the prenylation reaction, whereby a hydrophobic group (e.g. a farnesyl group) is attached to the protein in the presence of an enzyme (e.g. farnesyl protein transferase). Deactivation of the prenylation enzyme through covalent modification can therefore ultimately result in the mitigation and/or cessation of cancer cell growth. Various prenylation inhibitors having the necessary structural groups to bond covalently, or essentially irreversibly, to the prenylation enzyme include carbonyl or thiocarbonyl compounds (or masked versions of these compounds) and alpha oxo-epoxides bonded to a hydrophobic, substrate-mimicking group. The carbonyl or thiocarbonyl compounds also contain a nucleofugal atom or group to enhance the tendency to form covalent bonds.Type: GrantFiled: January 23, 2006Date of Patent: September 9, 2008Assignee: Arizona Biomedical Research CommissionInventors: Seth D. Rose, Scott R. Lefler, Steven R. Ottersberg, Ann Y. Kim, Karl J. Okolotowicz, Rosemarie F. Hartman
-
Publication number: 20080207943Abstract: A process for preparing racemic alkyl-5-halopent-4-enecarboxylic acids and esters thereof of the formula (I), in which R is a C1-C6-alkyl radical, R1 is H or C1-4-alkyl and X is chlorine, bromine or iodine, which comprises a) reacting a dialkyl alkylmalonate of the formula (II),in which R is as defined above and R2 is a C1-C4-alkyl radical, in the presence of a metal alkoxide of the formula MOR3, in which M may be Na, K or Li, and R3 is a C1-C4-alkyl radical, and in an organic solvent, with 1,3-dihalopropene to give the corresponding allylated malonate, then b) after full conversion, adding an inorganic salt and a C1-C6 alcohol to the reaction mixture, heating the reaction mixture to reflux temperature, then c) isolating the desired racemic ester of the formula (I) from the reaction mixture by extraction or direct distillation and d) if the racemic acid is the desired end product, hydrolyzing the ester function.Type: ApplicationFiled: July 3, 2006Publication date: August 28, 2008Applicant: DSM Fine Chemicals Austria NFG GMBH & Co KGInventors: Peter Pojarliev, Gerhard Steinbauer, Christian Burger
-
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
-
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
-
Patent number: 7232925Abstract: The present invention provides processes for producing a (4E)-5-chloro-2-isopropyl-4-pentenoate and an optical isomer of the (4E)-5-chloro-2-isopropyl-4-pentenoate, namely a process for producing a (4E)-5-chloro-2-isopropyl-4-pentenoate represented by the following formula (4), which comprises reacting a compound represented by the following formula (2) in the presence of an aprotic solvent (II) with a base (II) and then with (1E)-1,3-dichloro-1-propene to give a compound represented by the following formula (3), and dealkoxycarbonylating either ester in the compound represented by the following formula (3), and a process for producing a (S)-(4E)-5-chloro-2-isopropyl-4-pentenoate represented by the following formula (5), which comprises optically resolving a (4E)-5-chloro-2-isopropyl-4-pentenoate represented by the formula (4) obtained by the above-mentioned process (wherein R is a lower alkyl group or an aralkyl group).Type: GrantFiled: June 8, 2005Date of Patent: June 19, 2007Assignee: Asahi Glass Company, LimitedInventors: Nobuaki Mori, Yasushi Matsumura, Yoshitomi Morizawa, Toshihiko Kaminuma, Yuuichi Aoki
-
Patent number: 7202318Abstract: Polymerizable fluorinated ester compounds having formula (1) or (2) are novel wherein R1 is H, methyl or trifluoromethyl, R2 is a divalent hydrocarbon group, R3 is H or a monovalent hydrocarbon group, or R2 and R3, taken together, may form a ring, R4 is H, OH or a monovalent hydrocarbon group, and R5 is an acid labile group.Type: GrantFiled: July 7, 2005Date of Patent: April 10, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Takeru Watanabe, Seiichiro Tachibana, Jun Hatakeyama
-
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
-
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
-
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
-
Patent number: 7084295Abstract: A perfluoroadamantyl acrylate compound which is highly useful as a raw material for functional resins,etc.;and an intermediate therefore. The perfluoroadamantyl acrylate compound comprises perfluoroadamantane having a CH2?C(R)COO group(wherein R is a hydrogen atom, a methyl group or a trifluoromethyl group) at the 1-position, at each of the 1- and 3-positions, at each of the 1-, 3- and 5-positions, at each of the 1-, 3-, 5- and 7-positions, or at the 2-position.Type: GrantFiled: December 20, 2002Date of Patent: August 1, 2006Assignee: Idemitsu Kosan Co., Ltd.Inventors: Shinji Tanaka, Toshihide Yoshitome, Kouichi Kodoi, Hidetoshi Ono, Naoyoshi Hatakeyama
-
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
-
Patent number: 7067691Abstract: A process for producing an ?-substituted acrylic acid ester represented by the formula [1], wherein each of R1 and R2 is independently 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, includes reacting an ?-substituted acrylic acid anhydride represented by the formula [7], with 1,1-bis(trifluoromethyl)-1,3-diol represented by the formula [2].Type: GrantFiled: December 21, 2004Date of Patent: June 27, 2006Assignee: Central Glass Co., Ltd.Inventors: Takeo Komata, Kei Matsunaga, Yoshiki Hirotsu, Satoru Miyazawa, Katsunori Kawamura
-
Patent number: 7034179Abstract: The present invention provides a method for producing industrially useful fluorine-containing compounds such as a fluorinated ester compound and an acid fluoride compound. Namely, the present invention resides in a method for producing a fluorinated ester compound, which comprises fluorinating an ester compound which is an ester of a compound having hydroxyl group(s) with a compound having acyl fluoride group(s) and which has a structure which can be fluorinated, in a liquid phase to produce a fluorinated ester compound, wherein the fluorination is carried out in the form of a liquid mixture of the ester compound and the compound having acyl fluoride group(s).Type: GrantFiled: March 27, 2003Date of Patent: April 25, 2006Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Koichi Yanase, Yasuhiro Suzuki, Daisuke Shirakawa
-
Patent number: 6858748Abstract: The novel compound of the disclosure is 4-chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19), and it alone or in combination with 4-(4-Ethoxy-phenyl)-2-(N?-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13), appears useful in humans as therapeutic means for the eradication of tumors from the human's colon.Type: GrantFiled: January 13, 2004Date of Patent: February 22, 2005Assignee: Research Foundation of the University of Central FloridaInventors: D. Howard Miles, Solodnikov Sergey Yurjevich, Krasnykh Olga Petrovna, Lisovskaja Natalja Anatoljevna, Elena A. Goun
-
Patent number: 6852876Abstract: The novel compound of the disclosure is 4-chloro-4-(4-ethoxy-phenyl)-2-(fluoren-9-ylidene-hydrazono)-but-3-enoic acid methyl ester (3F-19), and it alone or in combination with 4-(4-Ethoxy-phenyl)-2-(N?-fluoren-9-ylidene-hydrazino)-2-hydroxy-4-oxo-butyric acid methyl ester (OF-13), appears useful in humans as therapeutic means for the eradication of tumors from the human's colon.Type: GrantFiled: June 7, 2002Date of Patent: February 8, 2005Assignee: University of Central FloridaInventors: D. Howard Miles, Solodnikov Sergey Yurjevich, Lisovskaja Natalja Anatoljevna, Elena A. Goun
-
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
-
Publication number: 20040236046Abstract: The present invention relates to a polymerizable monomer represented by the general formula (1), 1Type: ApplicationFiled: June 30, 2004Publication date: November 25, 2004Applicants: Central Glass Company, Limited, F-Tech, Inc.Inventors: Satoru Miyazawa, Kazuhiko Maeda, Kenji Tokuhisa, Shoji Arai