Halogen In Alcohol Moiety Patents (Class 560/223)
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Patent number: 11254765Abstract: A curable composition containing at least one of a haloalkyl ether (meth)acrylate or a haloalkenyl ether (meth)acrylate and, optionally, one or more different types of co-monomers is cured to provide a polymer having advantageous properties as a result of the incorporation of halogenated functionality derived from the haloalkyl/haloalkenyl ether (meth)acrylate monomer.Type: GrantFiled: September 25, 2018Date of Patent: February 22, 2022Assignee: Arkema Inc.Inventors: Benjamin Bin Chen, Craig Alan Polsz, Lucy Clarkson, Jing-Han Wang
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Patent number: 10752574Abstract: The present invention relates to a method for preparing a fluorinated methacrylate compound which can be used as a fluorine monomer for synthesizing a functional polymer having high oxygen permeability, water repellency and stain resistance. Specifically, the method can be carried out by a process of reacting an alcohol derivative and methacrylic acid anhydride in the presence of an imidazole-based base to obtain a fluorinated methacrylate. According to the preparation method of the present invention, since the reaction is carried out at room temperature and there is no process of removing the byproducts formed during the reaction, a high yield of fluorinated methacrylate can be obtained by a simple method within a short period of time.Type: GrantFiled: June 24, 2019Date of Patent: August 25, 2020Assignee: Samhwa Paints Industries Co., Ltd.Inventors: Sung Hyun Ko, Myeng Chan Hong
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Patent number: 10173960Abstract: An object of the present invention is to provide a method for stabilizing an acrylic acid derivative, and a composition containing an acrylic acid derivative in which the acrylic acid derivative is stabilized. The present invention provides a composition comprising: (A) an acrylic acid derivative represented by Formula (I): (wherein Ra represents alkyl, fluoroalkyl, aryl that may have one or more substituents, or hydrogen; and X represents fluorine, alkyl, perfluoroalkyl, or hydrogen); and (B) aldehyde, wherein the content of acrylic acid derivative (A) is 30% (w/w) or more.Type: GrantFiled: April 8, 2016Date of Patent: January 8, 2019Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tomohito Hamada, Makoto Matsuura, Asako Yoshiyama, Akihiro Gotou, Manaho Miyazaki, Yosuke Kishikawa
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Patent number: 10099997Abstract: An object of the present invention is to provide a method for stabilizing an acrylic acid derivative, and a composition containing an acrylic acid derivative in which the acrylic acid derivative is stabilized. The present invention provides a composition comprising: (A) an acrylic acid derivative represented by Formula (I): (wherein R1 and R2 are the same or different, and each represents alkyl, fluoroalkyl, aryl that may have one or more substituents, halogen, or hydrogen; R3 represents alkyl, fluoroalkyl, aryl that may have one or more substituents, or hydrogen; and X represents fluoroalkyl, alkyl, halogen, or hydrogen); and (B) alcohol, wherein the content of acrylic acid derivative (A) is 30% (w/w) or more.Type: GrantFiled: April 8, 2016Date of Patent: October 16, 2018Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tomohito Hamada, Yosuke Kishikawa, Makoto Matsuura, Asako Yoshiyama
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Patent number: 9656952Abstract: A reaction accelerator is provided which is used in a reaction of a compound including an isocyanate group that is not directly bonded to an aromatic ring in a molecule with a compound including an active hydrogen-containing group and is formed of a compound including a halogenated carbamoyl group. A production method is provided which includes reacting a compound including an isocyanate group that is not directly bonded to an aromatic ring in a molecule with a compound including an active hydrogen-containing group to produce a urethane compound, a thiourethane compound, an amide compound or a urea compound, in which the reaction is performed in the presence of the reaction accelerator.Type: GrantFiled: July 22, 2014Date of Patent: May 23, 2017Assignee: SHOWA DENKO K.K.Inventors: Katsutoshi Ono, Tomomitsu Kato
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Patent number: 8889230Abstract: A fluorochemical derived from monomers with a side chain, wherein the side chain includes a perfluoroalkyl group with 1-6 carbon atoms and a hydrocarbon spacer group attached to the perfluoroalkyl group, wherein the spacer group has 15-50 carbon atoms. The perfluoroalkyl group is non-crystallizable at room temperature and the spacer group is crystallizable at room temperature.Type: GrantFiled: August 17, 2007Date of Patent: November 18, 2014Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Michael A. Yandrasits
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Patent number: 8877960Abstract: When sulfinating a carboxylic acid bromofluoroalkyl ester by using a sulfinating agent, an organic base is used, thereby obtaining a fluoroalkanesulfinic acid ammonium salt. This is oxidized to obtain a fluoroalkanesulfonic acid ammonium salt. This is used as the raw material and is converted to an onium salt or is converted to an onium salt by going through saponification and esterification, thereby obtaining a fluoroalkanesulfonic acid onium salt. This fluoroalkanesulfonic acid onium salt is useful as a photoacid generator used for chemically amplified resist materials, etc.Type: GrantFiled: March 12, 2010Date of Patent: November 4, 2014Assignee: Central Glass Company, LimitedInventors: Masashi Nagamori, Yuji Hagiwara, Takashi Masubuchi, Satoru Narizuka
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Patent number: 8742038Abstract: A resist composition for immersion exposure, including a base component (A) that exhibits changed solubility in an alkali developing solution under action of acid, an acid generator component (B) that generates acid upon exposure, and a fluorine-containing compound (C) represented by a general formula (c-1) shown below that is decomposable in an alkali developing solution: wherein R1 represents an organic group which may contain a polymerizable group, with the proviso that said polymerizable group has a carbon-carbon multiple bond, and the carbon atoms forming the multiple bond are not directly bonded to the carbon atom within the —C(?O)— group in general formula (c-1); and R2 represents an organic group having a fluorine atom.Type: GrantFiled: January 27, 2009Date of Patent: June 3, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Daiju Shiono, Takahiro Dazai, Sanae Furuya, Tomoyuki Hirano, Takayoshi Mori
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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
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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: 8686098Abstract: A fluorine-containing polymer of the present invention contains a repeating unit (a) of the general formula (2) and has a mass-average molecular weight of 1,000 to 1,000,000. This polymer is suitably used in a resist composition for pattern formation by high energy ray radiation of 300 nm or less wavelength or electron beam radiation or a top coat composition for liquid immersion lithography and is characterized as having high water repellency, notably high receding contact angle. In the formula, R1 represents a polymerizable double bond-containing group; R2 represents a fluorine atom or a fluorine-containing alkyl group; R8 represents a substituted or unsubstituted alkyl group or the like; and W1 represents a single bond, a substituted or unsubstituted methylene group or the like.Type: GrantFiled: May 20, 2010Date of Patent: April 1, 2014Assignee: Central Glass Company, LimitedInventors: Kazunori Mori, Yuji Hagiwara, Masashi Nagamori, Yoshimi Isono, Satoru Narizuka, Kazuhiko Maeda
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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
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Patent number: 8580486Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.Type: GrantFiled: March 10, 2009Date of Patent: November 12, 2013Assignee: Central Glass Company, LimitedInventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
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Patent number: 8575300Abstract: Disclosed herein is a telechelic diacrylate fluoropolymer and a process for manufacture of the fluoropolymer. The diacrylate copolymer is of formula CH2?CR?COO—(CH2)n—R—(CH2)n—OOCCR??CH2, wherein R is selected from the group consisting of i) an oligomer comprising copolymerized units of vinylidene fluoride and perfluoro(methyl vinyl ether), ii) an oligomer comprising copolymerized units of vinylidene fluoride and hexafluoropropylene, iii) an oligomer comprising copolymerized units of tetrafluoroethylene and perfluoro(methyl vinyl ether), and iv) an oligomer comprising copolymerized units of tetrafluoroethylene and a hydrocarbon olefin, R? is H or—CH3, n is 1-4 and wherein said oligomer has a number average molecular weight of 1000 to 25,000 daltons.Type: GrantFiled: November 14, 2012Date of Patent: November 5, 2013Assignees: E I du Pont de Nemours and Company, Le Centre National de la Recherche ScienInventors: Ming-Hong Hung, Bruno Ameduri, Georgi Kostov
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Publication number: 20130284048Abstract: A composition of formula I [Rf(CH2)m(O)n]x-A wherein Rf is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof, m is a positive integer equal to or greater than 3, n is 0 or 1, x is 1 to about 3, and A is —P(O)(OR1)y(OM+)3-y-x, —C(O)CH(SO3?M+)CH2C(O)?, —(CH2CH2O)d(CH2CHR2O)eR3, or ?SO2B, M+ is an alkali metal ion, NH4+, or NH2(CH2CH2OH)2, B is N(R)2 or N(CH2CH3)(CH2CH2OH), R1 is C1 to C3 alkyl, and R2 is C1 to C4 alkyl, R3 is H or CH3, y is 0 to about 1, d is 0 to about 16, e is 0 to about 16, provided that (d+e) is from about 3 to about 16 is disclosed.Type: ApplicationFiled: June 24, 2013Publication date: October 31, 2013Inventors: Alexander Borisovich Shtarov, Michael Joseph Michalczyk, Charles Kenneth Taylor
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Patent number: 8535871Abstract: A radiation-sensitive resin composition includes a first polymer that includes a repeating unit having an acid-labile group and becomes alkali-soluble upon dissociation of the acid-labile group, and a radiation-sensitive acid-generating agent. The acid-labile group has a structure shown by a general formula (1). R1 represents a methyl group or the like, R2 represents a hydrocarbon group that forms a cyclic structure, R3 represents a fluorine atom or the like, R4 represents a carbon atom, and n1 is an integer from 1 to 7.Type: GrantFiled: December 14, 2011Date of Patent: September 17, 2013Assignee: JSR CorporationInventors: Yuusuke Asano, Takanori Kawakami
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Patent number: 8524942Abstract: An inimer, and process for making same, having the following formula: wherein X=halogen, nitroxide, thioester; R?H or CH3; and R?=aliphatic, non-aliphatic, linear or branched, mesogenic, non mesogenic, chiral, achiral, hydrocarbon, non-hydrocarbon, selected from fluorocarbon, oligo(oxyethylene) and siloxane substituents, alkyl, aryl, mesogenic group, non-mesogenic group, aliphatic, non-aliphatic, siloxane, perfluoroalkyl, perfluoroaryl, or other fluorocarbon group, and polymers, and the process of making them, from the inimer.Type: GrantFiled: October 4, 2007Date of Patent: September 3, 2013Assignee: The University of AkronInventors: Coleen R. Pugh, Anirudha Singh
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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
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Patent number: 8481660Abstract: Disclosed is (1) a mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)c OCOCR?CH2 and CF3(CF2)n?1(CF?CH)a CF2(CF2CF2)b(CH2CH2)cOCOCR?CH2, wherein R is a hydrogen atom or a methyl group, n is an integer of 1 to 5, a is an integer of 1 to 4, b is an integer of 0 to 3, and c is an integer of 1 to 3; (2) a fluorine-containing polymer containing the mixture as a polymerization unit; and (3) a water- and oil-repellent comprising the fluorine-containing polymer as an active ingredient. The fluoroalkyl alcohol-unsaturated carboxylic acid derivatives are produced by an esterification reaction of a mixture of fluoroalkyl alcohols represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)cOH and CF3(CF2)n?1(CF?CH)aCF2(CF2CF2)b, (CH2CH2)cOH, with acrylic acid or methacrylic acid.Type: GrantFiled: January 20, 2009Date of Patent: July 9, 2013Assignee: Unimatec Co., Ltd.Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato, Satoshi Kurihara
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Publication number: 20130171379Abstract: A thermal transfer film and an organic electroluminescent display manufactured using the thermal transfer film, the thermal transfer film including a base layer; and a transfer enhancement layer having a surface energy of about 25 dyne/cm or less.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Inventors: Hyoung Tae LIM, Kyoung Ku KANG, Jung Hyo LEE, Seong Heun CHO, Si Kyun PARK, Se Hyun PARK
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Patent number: 8435610Abstract: A copolymer of (meth)acrylic ester represented by a general formula (1) including a following repeating unit A and repeating unit B. In the general formula (1), R1 and R2 each independently represent hydrogen atom or methyl group; R3 represents an alkyl group having 1 to 4 carbon atoms; Y represents an atomic group forming an aromatic ring; x represents 1 to n, n represents the number of fluorine atoms which can be contained in the aromatic ring; and a and b each independently represent an integer of 1 or more.Type: GrantFiled: October 5, 2006Date of Patent: May 7, 2013Assignee: Japan Science and Technology AgencyInventors: Yasuhiro Koike, Yoshiyuki Okamoto, Akihiro Tagaya
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Patent number: 8426106Abstract: A Photoresist composition comprising a polymer comprising a structural unit derived from a compound represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, R2 represents a C6-C12 aromatic hydrocarbon group which can have one or more substituents, R3 represents a cyano group or a C1-C12 hydrocarbon group which can have one or more substituents and which can contain one or more heteroatoms, A1 represents a single bond, —(CH2)g—CO—O—* or —(CH2)h—O—CO—(CH2)i—CO—O—* wherein g, h and i each independently represent an integer of ?1 to 6 and * represents a binding position to the nitrogen atom, a resin having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid, and an acid generator.Type: GrantFiled: October 12, 2010Date of Patent: April 23, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Junji Shigematsu
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Publication number: 20130075364Abstract: Methods for forming a pattern in a lithography process for semiconductor wafer manufacturing are provided. In an example, a method includes forming a photoresist layer over a material layer; performing a first exposure process on the photoresist layer, thereby forming an exposed photoresist layer having soluble portions and unsoluble portions; treating the exposed photoresist layer, wherein the treating includes one of performing a second exposure process on the exposed photoresist layer and forming an adsorbing chemical layer over the exposed photoresist layer; and developing the exposed and treated photoresist layer to remove the soluble portions of the photoresist layer, wherein the unsoluble portions of the photoresist layer form a photoresist pattern that exposes portions of the material layer.Type: ApplicationFiled: September 22, 2011Publication date: March 28, 2013Applicant: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.Inventors: Chien-Wei Wang, Ko-Bin Kao, Wei-Liang Lin, Jui-Ching Wu, Chia-Hsiang Lin, Ai-Jen Jung
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Patent number: 8394905Abstract: Disclosed herein is a telechelic diacrylate fluoropolymer and a process for manufacture of the fluoropolymer. The diacrylate copolymer is of formula CH2?CR?COO—(CH2)n—R—(CH2)n—OOCCR??CH2, wherein R is selected from the group consisting of i) an oligomer comprising copolymerized units of vinylidene fluoride and perfluoro(methyl vinyl ether), ii) an oligomer comprising copolymerized units of vinylidene fluoride and hexafluoropropylene, iii) an oligomer comprising copolymerized units of tetrafluoroethylene and perfluoro(methyl vinyl ether), and iv) an oligomer comprising copolymerized units of tetrafluoroethylene and a hydrocarbon olefin, R? is H or —CH3, n is 1-4 and wherein said oligomer has a number average molecular weight of 1000 to 25,000 daltons.Type: GrantFiled: July 16, 2009Date of Patent: March 12, 2013Assignees: E I du Pont de Nemours and Company, Le Centre National de la Recherche ScienceInventors: Ming-Hong Hung, Bruno Ameduri, Georgi Kostov
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Patent number: 8318877Abstract: A copolymer composition comprising monomers copolymerized in the following percentages by weight: (a) from about 20% to about 95% of a monomer, or mixture of monomers, of formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]m-L-C(O)—C(R)?CH2??(I) wherein R is H, Cl, F or CH3, L is O, S, NH, S—(CH2)rO, S—(CH2)rNH, OC(O)NH—CH2CH2O, NHC(O)NHCH2CH2O, S—(CH2)rOC(O)NHCH2CH2O, or S(CH2)rNHC(O)NHCH2CH2O, and (b) from about 5% to about 80% of at least one of: (i) an alkyl (meth)acrylate monomer having a linear, branched or cyclic alkyl group of from about 6 to about 18 carbons; or (II) a monomer of formula (II) (R2)2N—R3—O—C(O)—C(R)?CH2??(II) wherein R is H, Cl, F or CH3, each R2 is independently a C1 to C4 alkyl; and R3 is a divalent linear or branched C1 to C4 alkylene; and wherein the nitrogen is from about 40% to 100% salinized; or (iii) a mixture thereof.Type: GrantFiled: May 20, 2008Date of Patent: November 27, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Weiming Qiu, Anilkumar Raghavanpillai, Peter Michael Murphy, Jessica Louise Flatter
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Publication number: 20120203028Abstract: The present invention provides a process for manufacturing acrylate esters of trinol, dinol, and didinol, which avoids the undesired thermopolymerization of the esters and provides highly pure monomers for the preparation of plastic lenses.Type: ApplicationFiled: September 7, 2010Publication date: August 9, 2012Applicant: BROMINE COMPOUNDS LTD.Inventors: Dov Beruben, Ofra Yosef, Michael Peled
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Patent number: 8231973Abstract: Antireflective film articles and low refractive index coating compositions are described that comprises a fluorinated free-radically polymerizable polymeric (e.g. intermediate) material. The free-radically polymerizable fluorinated polymeric intermediate comprises the reaction product of i) at least one multi-functional free-radically polymerizable material having a fluorine content of at least 25 wt-%, and ii) optionally other multi-functional free-radically polymerizable material. The total amount of multi-functional materials is preferably at least about 25 wt-%.Type: GrantFiled: May 4, 2007Date of Patent: July 31, 2012Assignee: 3M Innovative Properties CompanyInventors: Marc D. Radcliffe, Thomas P. Klun, Lan H. Liu, Richard J. Pokorny, Suresh Iyer, Zai-Ming Qiu
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Patent number: 8178638Abstract: A composition comprising a copolymer having repeating units in any sequence of Formula I wherein Rf is a straight or branched perfluoroalkyl group which is optionally interrupted by at least one oxygen atom, X3 is oxygen or X1, each X1 is independently an organic divalent linking group, G is F or CF3, A is an amide, X2 is an organic linking group, Y is O, N or S, Z is H, a straight or branched alkyl group or halide, B is H or wherein Rf, X1, X3, G, and A are as defined above, and each W is independently various copolymer units.Type: GrantFiled: May 26, 2010Date of Patent: May 15, 2012Assignee: E.I. du Pont de Nemours and CompanyInventor: Weiming Qiu
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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
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Publication number: 20120082934Abstract: [Problem] To reduce the time required for a film to exhibit decreased hydrophobicity after liquid immersion lithography while allowing the surface of a film to exhibit high hydrophobicity during liquid immersion lithography. [Solution] A radiation-sensitive resin composition including (A) a polymer that includes a repeating unit (a1) and a fluorine atom, and (B) a photoacid generator, the repeating unit (a1) including a group shown by any of the following formulas (1-1) to (1-3).Type: ApplicationFiled: September 23, 2011Publication date: April 5, 2012Applicant: JSR CorporationInventors: Kazuo Nakahara, Mitsuo Sato, Yusuke Asano
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Publication number: 20120083580Abstract: 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: ApplicationFiled: September 22, 2011Publication date: April 5, 2012Inventors: Takeshi KINSHO, Yuuki Suka, Yuji Harada, Koji Hasegawa, Takeshi Sasami
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Publication number: 20120077126Abstract: A fluorine-containing polymer of the present invention contains a repeating unit (a) of the general formula (2) and has a mass-average molecular weight of 1,000 to 1,000,000. This polymer is suitably used in a resist composition for pattern formation by high energy ray radiation of 300 nm or less wavelength or electron beam radiation or a top coat composition for liquid immersion lithography and is characterized as having high water repellency, notably high receding contact angle. In the formula, R1 represents a polymerizable double bond-containing group; R2 represents a fluorine atom or a fluorine-containing alkyl group; R8 represents a substituted or unsubstituted alkyl group or the like; and W1 represents a single bond, a substituted or unsubstituted methylene group or the like.Type: ApplicationFiled: May 20, 2010Publication date: March 29, 2012Inventors: Kazunori Mori, Yuji Hagiwara, Masashi Nagamori, Yoshimi Isono, Satoru Narizuka, Kazuhiko Maeda
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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
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Prepolymerizable surface active monomers with both fluorine-containing groups and hydrophilic groups
Patent number: 8071704Abstract: Provided are surface modified contact lenses formed from one or more fumaric- or itaconic-containing prepolymers having reactive functionality that is complimentary to surface modifying polymers.Type: GrantFiled: September 30, 2008Date of Patent: December 6, 2011Assignee: Bausch & Lomb IncorporatedInventors: Weihong Lang, Yu-Chin Lai -
Patent number: 8044235Abstract: A monomer is provided which is excellent in reactivity, can give high heat resistance and high refractive index, and has two or more polymerizable functional groups with different polymerization properties and an aromatic ring in the molecule. An industrial advantageous process for producing the monomer is also provided. The monomer is an aromatic isocyanate compound containing a (meth)acryloyl group, and is represented by Formula (I): wherein R1 is a single bond or a linear or branched alkylene group of 1 to 5 carbon atoms, R2 is a hydrogen atom or a methyl group, R3 is a single bond or a linear or branched alkylene group of 1 to 3 carbon atoms, X is independently a halogen atom or an electron-withdrawing group, m is an integer ranging from 0 to 4, n is an integer ranging from 1 to 3, and 1?m+n?5.Type: GrantFiled: March 15, 2006Date of Patent: October 25, 2011Assignee: Showa Denko K.K.Inventors: Kaneo Nozawa, Katsutoshi Ohno, Yotaro Hattori
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Publication number: 20100233419Abstract: A composition comprising a copolymer having repeating units in any sequence of Formula I wherein Rf is a straight or branched perfluoroalkyl group having from about 1 to about 20 carbon atoms, or a mixture thereof, which is optionally interrupted by at least one oxygen atom, X3 is oxygen or X1, each X1 is independently an organic divalent linking group having from about 1 to about 20 carbon atoms, optionally containing an oxygen, nitrogen, or sulfur, or a combination thereof, G is F or CF3, A is an amide, j is zero or positive integer, X2 is an organic linking group, Y is O, N or S, h is zero when Y is N, and h is one when Y is O or S, Z is H, a straight or branched alkyl group having from about 1 to about 4 carbon atoms, or halide, B is H or wherein Rf, X1, X3, G, A, and j are as defined above, provided that when B is H, j is a positive integer, m is a positive integer, q is zero or a positive integer when Y is O, and q is a positive integer when Y is N or S, p is zero or a positive integerType: ApplicationFiled: May 26, 2010Publication date: September 16, 2010Applicant: E.I.DU PONT DE NEMOURS AND COMPANYInventor: Weiming Qiu
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Publication number: 20100234521Abstract: A fluorochemical derived from monomers with a side chain, wherein the side chain includes a perfluoroalkyl group with 1-6 carbon atoms and a hydrocarbon spacer group attached to the perfluoroalkyl group, wherein the spacer group has 15-50 carbon atoms. The perfluoroalkyl group is non-crystallizable at room temperature and the spacer group is crystallizable at room temperature.Type: ApplicationFiled: August 17, 2007Publication date: September 16, 2010Inventors: Richard M. Flynn, Michael A. Yandrasits
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Publication number: 20100179262Abstract: A composition including at least one first divalent unit represented by formula: Each Rf is independently selected from the group consisting of Rfa—(O)t—CHF—(CF2)n—; [Rfa—(O)t—C(L)H—CF2—O]m—W—; Rfb-O—(CF2)p-; F(CkF2k)—(O—CkF2k)P—O—CF2—; and CF3—O—(CF2)3—(OCF(CF3)—CF2)Z—O-L1-. Each Q is independently selected from the group consisting of a bond, —C(O)—N(R1)—, and —C(O)—O—. Each X is independently selected from the group consisting of alkylene and arylalkylene, wherein alkylene and arylalkylene are each optionally interrupted by at least one ether linkage and optionally terminated by —N(R1)—C(O)— or —O—C(O)—. R and R1 are each independently selected from the group consisting of hydrogen and alkyl having from 1 to 4 carbon atoms. Rfa represents a partially or fully fluorinated alkyl group having from 1 to 10 carbon atoms and optionally interrupted with at least one oxygen atom. Rfb is selected from the group consisting of CF3CFH— and F(CjF2j)-.Type: ApplicationFiled: June 6, 2008Publication date: July 15, 2010Inventors: Rudolf J. Dams, Miguel A. Guerra, Klaus Hintzer, Michael Jürgens, Harald Kaspar, Kai H. Lochhaas, Andreas R. Maurer, Zai-Ming Qiu, Worner Schwertfeger, Michael S. Terrazas, Tilman C. Zipplies
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Patent number: 7700800Abstract: The present invention discloses a method for producing a fluorine-containing alkyl (meth)acrylate represented by the following general formula (2): Rf—(CH2)k-[-A-(CH2)l—]m—OCOCR?CH2??(2) (wherein R is a hydrogen atom or a methyl group), characterized by reacting a fluorine-containing alcohol represented by the following general formula (1): Rf—(CH2)k-[-A-(CH2)l—]m—OH??(1) (wherein Rf is a perfluoroalkyl group having 1 to 21 carbon atoms; A is S, SO or SO2; k is 0, 1 or 2; l is 1, 2 or 3; m is 0 or 1; however, a case of k=0 and m=0 is excluded), (meth)acrylic acid, and a sulfonic acid halide in the presence of a base containing at least one kind of tertiary amine.Type: GrantFiled: March 15, 2006Date of Patent: April 20, 2010Assignees: Tokuyama Corporation, Daikin Industries Ltd.Inventors: Masao Yamaguchi, Fumihiko Yamaguchi
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Publication number: 20100069590Abstract: 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: ApplicationFiled: October 15, 2007Publication date: March 18, 2010Applicants: Tokyo Ohka Kogyo Co., Ltd., Daito Chemix CorporationInventors: Yoshiyuki Utsumi, Hiroaki Shimizu, Kyoko Ohshita, Toshiharu Shimamaki, Kenshin Niwa, Seihin Shu
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Patent number: 7579498Abstract: A process for preparing fluorinated alkyl carboxylate esters comprises reaction of a silver carboxylate or silver carboxylate precursor, such as silver (I) iodide with a fluorinated alkyl iodide and a carboxylic acid. Preferably the fluorinated alkyl iodide has the general formula CF3(CF2)nCH2CH2I, wherein n is an integer in the range of from 1 to 29 and the carboxylic acid is acetic acid, acrylic acid or methacrylic acid.Type: GrantFiled: November 29, 2005Date of Patent: August 25, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Allen Andrews, Alexander Borisovich Shtarov, Joseph Norman Hockman
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Publication number: 20090023948Abstract: The present invention discloses a method for producing a fluorine-containing alkyl (meth)acrylate represented by the following general formula (2): Rf—(CH2)k-[-A-(CH2)l—]m—OCOCR?CH2??(2) (wherein R is a hydrogen atom or a methyl group), characterized by reacting a fluorine-containing alcohol represented by the following general formula (1): Rf—(CH2)k-[-A-(CH2)l—]m—OH??(1) (wherein Rf is a perfluoroalkyl group having 1 to 21 carbon atoms; A is S, SO or SO2; k is 0, 1 or 2; 1 is k, 2 or 3; m is 0 or 1; however, a case of k=0 and m=0 is excluded), (meth)acrylic acid, and a sulfonic acid halide in the presence of a base containing at least one kind of tertiary amine.Type: ApplicationFiled: March 15, 2006Publication date: January 22, 2009Applicants: TOKUYAMA CORPORATION, DAIKIN INDUSTRIES, LTD.Inventors: Masao Yamaguchi, Fumihiko Yamaguchi
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Publication number: 20090011199Abstract: Disclosed is a fluorine-containing unsaturated carboxylic acid represented by formula (1), wherein R1 represents a polymerizable double-bond containing 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 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 chemically amplified resist composition that is transparent to KrF or ArF excimer laser light and has a high resolution and is capable of forming a pattern having a rectangular section with no swelling.Type: ApplicationFiled: June 26, 2008Publication date: January 8, 2009Applicant: Central Glass Company, LimitedInventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiro Yamanaka
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Publication number: 20080315147Abstract: Fluoroalkyl amidoalkyl alcohols of the formula are disclosed and their corresponding (meth)acrylate esters. These fluoroalkyl amidoalkyl (meth)acrylate monomers can be copolymerized with a wide variety of conventional ethylenically unsaturated monomers. The resulting copolymers are useful as water, oil- and grease-proofing agents for paper, textiles and hard surfaces such as masonry and wood.Type: ApplicationFiled: June 18, 2007Publication date: December 25, 2008Applicant: Huntsman International LLCInventor: Shobha Kantamneni
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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
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Patent number: 7390917Abstract: A method of producing a mixture of fluorine-containing (meth)acrylate esters, the method including: (A) a telomerization step of obtaining the mixture of the fluoroalkyl iodide telomers; (B) an ethylene addition step of adding ethylene to the mixture of the fluoroalkyl iodide telomers obtained in the step (A) to give a mixture of ethylene adducts; and (C) an esterification step of reacting the mixture of the ethylene adducts obtained in the step (B) with a (meth)acrylate compound to obtain fluorine-containing (meth)acrylate esters.Type: GrantFiled: March 9, 2005Date of Patent: June 24, 2008Assignee: Daikin Industries, Ltd.Inventors: Yukio Homoto, Kunitada Tanaka
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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: 7205443Abstract: A process for producing a fluorine-containing 2,4-diol represented by the formula [4], wherein R1 represents a hydrogen atom or an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; R2 represents an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; and R1 and R2 are optionally bonded to each other to form a ring, includes reducing a hydroxy ketone represented by the formula [3], wherein R1 and R2 are defined as above, by hydrogen in the presence of a ruthenium catalyst.Type: GrantFiled: January 26, 2005Date of Patent: April 17, 2007Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Kei Matsunaga, Yoshiki Hirotsu, Shinya Akiba
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Patent number: 7199262Abstract: The invention relates to a novel compound, 3-hydroxypropyl ester of 2-trifluoromethyl acrylic acid, represented by the formula [1]. The invention further relates to a process for producing the compound.Type: GrantFiled: June 15, 2005Date of Patent: April 3, 2007Assignee: Central Glass Company, LimitedInventors: Takahisa Tada, Seiji Murata, Akihiro Fukui, Junji Negishi
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Patent number: 7176267Abstract: A fluorine-containing polymer which is an active component of a surface treatment agent having excellent water- and oil-repellency is constituted by a fluorine-containing polyether monomer of the formula: wherein Rf is a perfluoroalkyl group having 1 to 18 carbon atoms, R is hydrogen or a methyl group, A1 is a divalent linear or branched aliphatic group having 1 to 20 carbon atoms, A2 is a direct bond, or a divalent linear or branched aliphatic group having 1 to 10 carbon atoms which may have an ether linkage, X is a trivalent linear or branched aliphatic group having 2 to 5 carbon atoms, and n is from 1 to 100.Type: GrantFiled: July 26, 2002Date of Patent: February 13, 2007Assignee: Daikin Industries, Ltd.Inventors: Ikuo Yamamoto, Nobuo Fukita