Fluorine-containing Monomer Contains A Sulfur Atom Patents (Class 526/243)
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Patent number: 8236425Abstract: A composition comprises a distribution of telomers of ethylene and at least one fluoroalkyl or perfluoroalkyl halide, the telomers comprising at least one polymethylene segment (—(CH2)n—) and at least one halomethyl group (—CXH2) and optionally comprising at least one non-fluorine heteroatom, and the halogen being selected from iodine and bromine; wherein the distribution has a number average ratio of methylene moieties of the polymethylene segment to the halomethyl groups of at least about 15.Type: GrantFiled: December 27, 2007Date of Patent: August 7, 2012Assignee: 3M Innovative Properties CompanyInventors: George G. I. Moore, Yu Yang, Richard M. Flynn
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Patent number: 8236213Abstract: A process for producing a perfluoropolymer, the process including extruding a polymer obtained by polymerizing a perfluoromonomer to prepare strands, and bringing a gas comprising from 3 to 50 volume % of fluorine gas into contact with the strands; the process being conducted on an apparatus that includes an extruder for melting and extruding the polymer obtained by polymerizing a perfluoromonomer, a die having a plurality of pores for preparing the strands from the molten polymer extruded, and a fluorination tank for bringing the gas comprising from 3 to 50 volume % of fluorine gas into contact with the strands.Type: GrantFiled: May 15, 2008Date of Patent: August 7, 2012Assignee: Asahi Glass Company, LimitedInventors: Nobuyuki Kasahara, Noriaki Miyaki, Fusaaki Takeo, Satoshi Shiratori
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Patent number: 8232353Abstract: A polymer film substrate is irradiated with ions to make a large number of nano-sized through-holes and the substrate may be further irradiated with ionizing radiation so that a functional monomer may be grafted or co-grafted onto a surface of the film and within the holes; in addition, sulfonic acid group(s) may be introduced into the graft chains to produce a polymer ion-exchange membrane that may have high oxidation resistance, dimensional stability, electrical conductivity and/or methanol resistance, as well as may have an ion-exchange capacity controlled over a wide range.Type: GrantFiled: August 21, 2007Date of Patent: July 31, 2012Assignee: Japan Atomic Energy Research InstituteInventors: Masaru Yoshida, Tetsuya Yamaki, Masaharu Asano, Yosuke Morita
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Patent number: 8226876Abstract: Disclosed herein is a method to produce a semi-crystalline fluoro-polymer film. A semi-crystalline fluoro-polymer material is used. The material is compressed to produce the film. During compression, the material is maintained at a temperature below the melting point of the material. The compression step can be cycled to allow cooling of the material between compression stages. Alternative methods are provided for compressing the material with a co-extrusion substrate, extruding the material and utilizing mandrel expansion for the material.Type: GrantFiled: May 9, 2006Date of Patent: July 24, 2012Assignee: The United States of America as represented by the Secretary of the NavyInventors: O. Richard Hughes, Alfred R. Austen
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Publication number: 20120171616Abstract: A compound has formula (I): Q-O-(A)-Z?G+??(I) wherein Q is a halogenated or non-halogenated, C2-30 olefin-containing group, A is a fluorine-substituted C1-30 alkylene group, a fluorine-substituted C3-30 cycloalkylene group, a fluorine-substituted C6-30 arylene group, or a fluorine-substituted C7-30 alkylene-arylene group, Z is an anionic group comprising sulfonate, sulfonamide, or sulfonamide, and G+ has formula (II): wherein X is S or I, each R0 is halogenated or non-halogenated and is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination of these, wherein when X is S, one of the R0 groups is optionally attached to one adjacent R0 group by a single bond, and a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 3. A copolymer, a photoresist, a coated substrate and method of patterning are disclosed.Type: ApplicationFiled: December 29, 2011Publication date: July 5, 2012Inventors: James W. Thackeray, Suzanne M. Coley, Vipul Jain, Owendi Ongayi, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour
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Publication number: 20120172555Abstract: A monomer compound has the formula (I): where each R1, R2, and R3 is independently H, F, C1-10 alkyl, fluoro-substituted C1-10 alkyl, C1-10 cycloalkyl, or fluoro-substituted C1-10 cycloalkyl, provided that at least one of R1, R2, or R3 is F; n is an integer of from 1 to 10, A is a halogenated or non-halogenated C2-30 olefin-containing polymerizable group, and G+ is an organic or inorganic cation. The monomer is the reaction product of a sultone precursor and the oxyanion of a hydroxy-containing halogenated or non-halogenated C2-30 olefin-containing compound. A polymer includes the monomer of formula (I).Type: ApplicationFiled: December 29, 2011Publication date: July 5, 2012Inventors: Suzanne M. Coley, David R. Wilson, Francis J. Timmers
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Publication number: 20120156618Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a resin (P) containing not only at least one repeating unit (A) that when exposed to actinic rays or radiation, is decomposed to thereby generate an acid and is expressed by any of general formulae (I) to (III) below but also a repeating unit (B) containing at least an aromatic ring group provided that the repeating unit (B) does not include any of those of general formulae (I) to (III). (The characters used in general formulae (I) to (III) have the meanings mentioned in the description.Type: ApplicationFiled: August 31, 2010Publication date: June 21, 2012Applicant: FUJIFILM CORPORATIONInventors: Hidenori Takahashi, Shuji Hirano, Takayuki Ito, Hideaki Tsubaki
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Publication number: 20120136077Abstract: A fluorinated copolymer including at least one recurrent unit of the following formula (I): and at least one recurrent unit of the following formula (II): in which: RF represents a perfluorocarbon chain optionally including one or more oxygen atoms; X represents a halogen atom, OR with R representing a hydrogen atom or a cation; R1 represents a hydrocarbon chain or perfluorocarbon chain; and Z represents a perfluorocarbon chain.Type: ApplicationFiled: July 13, 2010Publication date: May 31, 2012Applicants: Centre National de la Recherche Scientifique, Commissariat a I'energie atomique et aux energies alternativesInventors: Aurélien Soules, Bruno Ameduri, Bernard Boutevin, Hervé Galiano
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Publication number: 20120135357Abstract: A positive resist composition comprising a polymer comprising recurring units of a specific structure adapted to generate an acid upon exposure to high-energy radiation, recurring units of a lactone ring-containing structure, and acid labile units, all the recurring units being free of hydroxyl, can form a fine size pattern having a rectangular profile and improved collapse resistance.Type: ApplicationFiled: November 23, 2011Publication date: May 31, 2012Inventors: Tomohiro KOBAYASHI, Takayuki Nagasawa, Ryosuke Taniguchi, Youichi Ohsawa, Kenji Funatsu, Seiichiro Tachibana
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Publication number: 20120129103Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.Type: ApplicationFiled: November 9, 2011Publication date: May 24, 2012Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
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Patent number: 8173350Abstract: An oxime compound represented by the formula (I): wherein Y represents an unsubstituted or substituted n-valent C6-C14 aromatic hydrocarbon group, n represents an integer of 1 to 6, R1 represents a C1-C30 aliphatic hydrocarbon group etc., R2 represents a linear or branched chain C1-C20 aliphatic hydrocarbon group etc., W represents —CO—O— etc., Q1 and Q2 each independently represent a fluorine atom etc., Z represents a C1-C20 halogenated aliphatic hydrocarbon group etc, and the resist composition containing the same.Type: GrantFiled: July 21, 2009Date of Patent: May 8, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Takashi Hiraoka, Ichiki Takemoto
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Patent number: 8168734Abstract: The invention relates to compounds represented by Formula (1): wherein Ra is independently halogen, cyano, —CF3, —CF2H, —CFH2, —OCF3, —OCF2H, —N?C?O, —N?C?S or alkyl having a carbon number of approximately 1 to approximately 20; in the alkyl, optional —CH2— may be substituted with —O—, —S—, —SO2—, —CO—, —COO—, —OCO—, —CH?CH—, —CF?CF— or —C?C—, and optional hydrogen may be substituted with halogen; Rb is fluorine or —CF3; A is independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl or bicyclo[2.2.Type: GrantFiled: February 23, 2011Date of Patent: May 1, 2012Assignees: JNC Corporation, Chisso Petrochemical CorporationInventor: Takashi Kato
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Publication number: 20120100487Abstract: A resist composition including a base component that generates acid upon exposure and also exhibits increased polarity by action of acid, the base component including a polymeric compound having a structural unit that generates acid upon exposure; a structural unit derived from an acrylate ester, in which a hydrogen atom bonded to a carbon atom on the ?-position may be substituted with a substituent, and also includes an acid decomposable group that exhibits increased polarity by action of acid; and a structural unit represented by a particular general formula.Type: ApplicationFiled: October 19, 2011Publication date: April 26, 2012Applicant: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Hirano, Daichi Takaki, Daiju Shiono, Kenri Konno, Kensuke Matsuzawa, Jun Iwashita
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Publication number: 20120091437Abstract: An object of the present invention is to provide a polymer having a low LUMO, a high charge transport property, and further high solubility in a solvent. The present invention provides a polymer having a repeating unit represented by the formula (I): wherein Ar0 means an aromatic ring that may have a substituent or substituents, or a heterocycle that may have a substituent or substituents, and X1 and X2 are the same or different and each mean an oxygen atom or a sulfur atom.Type: ApplicationFiled: March 8, 2010Publication date: April 19, 2012Applicants: OSAKA UNIVERSITY, SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Yutaka Ie, Atsuki Yoshimura, Yoshio Aso, Masato Ueda
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Publication number: 20120082939Abstract: An active light ray sensitive or radioactive ray sensitive resin composition which satisfies high sensitivity, high resolution, good pattern configuration, and good line edge roughness at the same time to a great extent, while having sufficiently good outgassing performance during exposure, and an active light ray sensitive or radioactive ray sensitive film formed by using the composition, and a pattern-forming method, are provided. The active light ray sensitive or radioactive ray sensitive resin composition according to the present invention includes a resin (P) containing a repeating unit (A) which decomposes by irradiation with active light ray or radioactive ray to generate an acid, and a repeating unit (C) containing a primary or secondary hydroxyl group.Type: ApplicationFiled: October 4, 2011Publication date: April 5, 2012Applicant: FUJIFILM CorporationInventors: Takeshi KAWABATA, Hidenori Takahashi, Tomotaka Tsuchimura, Shuji Hirano, Hideaki Tsubaki
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Patent number: 8148483Abstract: The present invention is directed to fluoro silicone acrylates that are used in reaction either alone or with other monomers to make polymers that can modify the surface of hair skin or pigment. This makes them ideal for incorporation into pigmented products in personal care applications like make up and lipsticks.Type: GrantFiled: August 30, 2010Date of Patent: April 3, 2012Assignees: Phoenix Chemical, Siltech CorporationInventors: Anthony John O'Lenick, Jr., John Imperante
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Publication number: 20120077121Abstract: Fluoroalcohol compounds of formula (1) are useful in producing polymers which are used as the base resin to formulate radiation-sensitive resist compositions having transparency to radiation having a wavelength of up to 500 nm and improved development characteristics. R1 is hydrogen or a monovalent C1-C20 hydrocarbon group in which any constituent —CH2— moiety may be replaced by —O— or —C(?O)—, Aa is a (k1+1)-valent C1-C20 hydrocarbon or fluorinated hydrocarbon group, and k1 is 1, 2 or 3.Type: ApplicationFiled: September 19, 2011Publication date: March 29, 2012Inventors: Koji HASEGAWA, Takeru Watanabe, Tomohiro Kobayashi, Takeshi Kinsho
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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: 20120071372Abstract: The present invention relates to a method of removing and preventing water and condensate blocks in wells by contacting a subterranean formation with a composition comprising a low molecular weight fluorinated copolymer having perfluoro alkyl moieties which are no longer than C6. A fluorinated copolymer of low molecular weight of about 50,000 g/mol and a method of preparing the same are also disclosed.Type: ApplicationFiled: March 18, 2011Publication date: March 22, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: CHERYL LYNN IACONELLI, GERALD ORONDE BROWN, CHRISTOPHER JAMES MARTIN, Erick J. Acosta
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Publication number: 20120065108Abstract: Fluorinated polymeric microparticles, processes for preparing them and uses thereof as additives for fluid loss control of drilling fluids and methods of fluid loss control of drilling fluid loss with fluorinated microparticles and uses of fluoropolymers as fluid loss control agents. Said fluorinated polymeric microparticles comprise one or more repeating units derived from one or more fluorinated monomers and one or more repeating units derived from one or more acrylate monomers.Type: ApplicationFiled: June 2, 2010Publication date: March 15, 2012Inventors: Tom Opstal, Rudolf J. Dams, Rudy W. Van Campenhout, Francois C. D'Haese
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Publication number: 20120065291Abstract: A radiation-sensitive resin composition includes a first polymer including a repeating unit represented by a following formula (I). X+ is an onium cation. X+ in the formula (I) is preferably an onium cation represented by a following formula (1-1), an onium cation represented by a following formula (1-2) or a combination thereof.Type: ApplicationFiled: October 13, 2011Publication date: March 15, 2012Applicant: JSR CorporationInventors: Nobuji Matsumura, Yukio Nishimura, Akimasa Soyano, Ryuichi Serizawa, Noboru Otsuka, Hiroshi Tomioka
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Patent number: 8129567Abstract: A composition which provides surface effects to substrates comprising a polymer containing at least one urea linkage prepared by (i) reacting (1) at least one organic diioscyanate, polyisocyanate, or mixture thereof, and (2) at least one fluorochemical compound of Formula I Rf—O(CF2CF2)r(CH2CH2)q(R1)sXH??Formula (I) wherein Rf is a linear or branched C1 to C7 perfluoroalkyl optionally interrupted by one to three oxygen atoms, r is 1 to 3, q is 1 to 3, s is 0 or 1, X is O, S, or NR2 wherein R2 is H, or C1 to C6 alkyl, and R1 is a divalent radical selected from —S(CH2)n—, p is 1 to 50, and R3, R4 and R5 are each independently H or C1 to C6 alkyl; (ii) and then reacting with (3) water, a linking agent, or a mixture thereof.Type: GrantFiled: April 25, 2011Date of Patent: March 6, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Sheng Peng, Stephen James Getty, Timothy Edward Hopkins, Ying Wang
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Patent number: 8124221Abstract: The invention provides a fluoropolymer coated film comprising: a polymeric substrate film; and a fluoropolymer coating on the polymeric substrate film, the fluoropolymer coating comprising a vinyl fluoride copolymer comprised of about 40 to about 90 mole % of repeat units derived from vinyl fluoride and about 10 to about 60 mole % of repeat units derived from monomer selected from the group consisting of (a) and (b) below and mixtures thereof, with the proviso that about 0.Type: GrantFiled: December 21, 2007Date of Patent: February 28, 2012Assignees: E. I. du Pont de Nemours and Company, Dupont-Mitsui Flourochemicals Co LtdInventors: Ronald Earl Uschold, Jian Wang, Masahiro Yamamoto
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Patent number: 8114956Abstract: A polymer having a repeating unit represented by the following general formula (I) and a ferrocene-based reduction potential of ?1.5 to ?0.5 V as measured by a cyclic voltammetry method wherein Ar1 represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group, and these groups may be substituted by a substituent.Type: GrantFiled: March 5, 2008Date of Patent: February 14, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Yutaka Ie, Yoshio Aso, Yoshikazu Umemoto, Masato Ueda
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Patent number: 8110336Abstract: A resin comprising a structural unit represented by the formula (I): wherein Q1 and Q2 represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group in which one or more —CH2— may be replaced by —O— etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion.Type: GrantFiled: September 18, 2009Date of Patent: February 7, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando
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Publication number: 20120024308Abstract: A method of making up keratinous material with light-sensitive makeup, the method including applying on keratinous material a photochromic composition including a thermally stable photochromic agent in the already at least partially developed state.Type: ApplicationFiled: February 23, 2010Publication date: February 2, 2012Applicant: L'OREALInventors: Franck Giron, Henri Samain
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Patent number: 8105748Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C2-C20 hydrocarbon group having cyclic structure, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.Type: GrantFiled: October 16, 2009Date of Patent: January 31, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Jun Hatakeyama, Seiichiro Tachibana
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Patent number: 8101698Abstract: Provided are surface modified contact lenses formed from one or more fumaric-or itaconic-containing prepolymers having polymerizable functionality that is complimentary to polymerizable hydrophilic polymers.Type: GrantFiled: March 25, 2011Date of Patent: January 24, 2012Assignee: Bausch & Lomb IncorporatedInventor: Yu-Chin Lai
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Publication number: 20120010380Abstract: The present invention relates to a photo-reactive norbornene-based copolymer which has superior miscibility to various organic solvents or additives while exhibiting superior liquid crystal alignment property and can be preferably used to an alignment layer of liquid crystal display device, a method of preparing the same, and an alignment layer including the same.Type: ApplicationFiled: July 6, 2011Publication date: January 12, 2012Applicant: LG CHEM, LTD.Inventors: Dong-Woo Yoo, Sung-Ho Chun, Young-Chul Won, Dai-Seung Choi
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Publication number: 20120003589Abstract: A polymer for forming a resist protection film which is used in a liquid immersion lithography process to protect a photoresist layer, a composition for forming a resist protection film, and a method of forming a pattern of a semiconductor device using the composition are disclosed. The polymer for forming a resist protection film includes a repeating unit represented by Formula 1 below. In Formula 1, R1 is a hydrogen atom (H), a fluorine atom (F), a methyl group (—CH3), a C1-C20 fluoroalkyl group, or a C1-C5 hydroxyalkyl group, R2 is a C1-C10 linear or branched alkylene group or alkylidene group, or a C5-C10 cycloalkylene group or cycloalkylidene group, X is wherein n is an integer of 0 to 5 and * denotes the remaining moiety of Formula 1 after excluding X, and m, the stoichiometric coefficient of X, is 1 or 2.Type: ApplicationFiled: June 30, 2011Publication date: January 5, 2012Inventors: Jong Kyoung Park, Man Ho Han, Hyun Jin Kim, Deog Bae Kim
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Publication number: 20120003590Abstract: An actinic ray-sensitive or radiation-sensitive resin composition containing a resin having (A) a repeating unit represented by a specific formula (I) and (B) a repeating unit capable of generating an acid upon irradiation with an actinic ray or radiation.Type: ApplicationFiled: February 23, 2011Publication date: January 5, 2012Applicant: FUJIFILM CORPORATIONInventors: Shuji HIRANO, Hidenori TAKAHASHI, Tomotaka TSUCHIMURA, Takeshi KAWABATA, Hideaki TSUBAKI
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Publication number: 20110318693Abstract: An embodiment of the composition contains a resin (P) containing a repeating unit (A) that is configured to decompose when exposed to actinic rays or radiation to thereby generate an acid. The repeating unit (A) contains a cation structure with a monocyclic or polycyclic heterocycle containing a nitrogen atom.Type: ApplicationFiled: June 28, 2011Publication date: December 29, 2011Applicant: FUJIFILM CORPORATIONInventors: Hidenori TAKAHASHI, Tomotaka TSUCHIMURA, Shuji HIRANO, Takeshi KAWABATA, Hideaki TSUBAKI
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Patent number: 8071254Abstract: Crosslinkable polymers and crosslinked fluoropolymers are prepared from selected fluorinated dienes and monomers containing Br and I. Also disclosed are proton conductive membranes of these crosslinked fluoropolymers.Type: GrantFiled: December 29, 2008Date of Patent: December 6, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Zhen-Yu Yang, Amy Qi Han, legal representative
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Publication number: 20110294070Abstract: A polymer is obtained from a hydroxyphenyl methacrylate monomer having an acid labile group substituted thereon. A positive resist composition comprising the polymer as a base resin has a very high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good profile and minimal line edge roughness of a pattern after exposure, a retarded acid diffusion rate, and good etching resistance.Type: ApplicationFiled: June 1, 2011Publication date: December 1, 2011Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Seiichiro Tachibana, Koji Hasegawa
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Patent number: 8058376Abstract: A process for making an aqueous dispersion of fluoropolymer particles by polymerizing in a first polymerization step at least one fluorinated monomer having an ionic group in an aqueous polymerization medium in the presence of initiator, the polymerizing providing dispersed particulate of fluorinated ionomer, and polymerizing in a second polymerization step at least one fluorinated monomer in the aqueous polymerization medium in the presence of the dispersed particulate of fluorinated ionomer and initiator to form the aqueous dispersion of particles of fluoropolymer.Type: GrantFiled: December 18, 2009Date of Patent: November 15, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Munson Aten, Kenneth Wayne Leffew, Ralph Birchard Lloyd, Charles Joseph Noelke
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Patent number: 8056253Abstract: A system of drying a surface of a substrate is provided. The system includes a rotary support for supporting a substrate; and an assembly comprising a first dispenser, a second dispenser, and a third dispenser, the assembly positioned above the surface of the substrate, the second and third dispensers positioned on the assembly adjacent to and in contact with one another and spaced from the first dispenser, the second dispenser having an opening that is larger than an opening of the third dispenser, and the second dispenser being located between the first and third dispensers; and means for translating the assembly generally parallel to the surface of the substrate.Type: GrantFiled: January 12, 2010Date of Patent: November 15, 2011Inventors: Zhi (Lewis) Liu, Ismail Kashkoush, Hanjoo Lee
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Patent number: 8057985Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C1-C20 organic group, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.Type: GrantFiled: August 27, 2009Date of Patent: November 15, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
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Publication number: 20110269074Abstract: New polymers are provided comprising (i) one or more covalently linked photoacid generator moieties and (ii) one or more photoacid-labile groups, wherein the one or more photoacid generator moieties are a component of one or more of the photoacid-labile groups. Preferred polymers of the invention are suitable for use in photoresists imaged at short wavelengths such as sub-200 nm, particularly 193 nm.Type: ApplicationFiled: March 31, 2011Publication date: November 3, 2011Applicant: Rohm and Haas Electronic Materials LLCInventors: Emad Aqad, Cong Liu, Cheng-Bai Xu, Mingqi Li
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Patent number: 8048610Abstract: A polymer comprising recurring units having formulae (1), (2) and (3) is provided as well as a chemically amplified resist composition comprising the same. R1 is H, F, CH3 or CF3, Rf is H, F, CF3 or C2F5, A is an optionally fluorine or oxygen-substituted divalent organic group, R2, R3 and R4 are alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or may form a ring with the sulfur atom, N=0-2, R8 is H or alkyl, B is a single bond or optionally oxygen-substituted divalent organic group, a=0-3, b=1-3, and X is an acid labile group. The polymer generates a strong sulfonic acid which provides for effective cleavage of acid labile groups in a chemically amplified resist composition.Type: GrantFiled: April 23, 2009Date of Patent: November 1, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana, Takeshi Kinsho
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Publication number: 20110236823Abstract: The invention relates to new polymers that comprise units that contain one or more photoacid generator groups and photoresists that contain the polymers. Preferred polymers of the invention are suitable for use in photoresists imaged at short wavelengths such as sub-250 nm or sub-200 nm, particularly 248 nm and 193 nm.Type: ApplicationFiled: November 22, 2010Publication date: September 29, 2011Applicant: Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Roger A. Nassar
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Publication number: 20110232764Abstract: Disclosed are conjugated polymers having desirable properties as semiconducting materials. Such polymers can exhibit desirable electronic properties and possess processing advantages including solution-processability and/or good stability.Type: ApplicationFiled: March 15, 2011Publication date: September 29, 2011Inventors: Antonio Facchetti, Tobin J. Marks, Hui Huang, Zhihua Chen
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Patent number: 8026316Abstract: To provide a process for efficiently producing a perfluoropolymer having unstable terminal groups reduced. A process for producing a fluorination-treated perfluoropolymer, which comprises melting a thermoplastic perfluoropolymer to form strands and contacting the polymer strands with a fluorine gas. For fluorination-treatment of the perfluoropolymer, an apparatus 10 is used, which comprises a melt extruder 11 for melting and extruding the perfluoropolymer, a die 12 for forming the melt extruded polymer into continuous strands 1 and a fluorination tank 13 for contacting the continuous strands 1 with a fluorine gas.Type: GrantFiled: November 12, 2009Date of Patent: September 27, 2011Assignee: Asahi Glass Company, LimitedInventors: Nobuyuki Kasahara, Noriaki Miyake
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Publication number: 20110230631Abstract: The invention pertains to novel (per)fluoropolyethers comprising at least one (per)fluoropolyoxyalkylene chain (chain Rf) comprising at least one recurring unit (R2) having formula: —CF2—CF(CF2OSO2F)—O— [poly(fluorosulfate) PFPE], to a process for their manufacture, and to their use for providing functional (per)fluoropolyethers.Type: ApplicationFiled: December 2, 2009Publication date: September 22, 2011Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Giuseppe Marchionni, Silvia Petricci, Pier Antonio Guarda
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Patent number: 8017257Abstract: A polymer electrolyte membrane made of a polymer having a low electrical resistance, high heat resistance and is strong against repeats of swelling and shrinkage. Thus, a membrane/electrode assembly for polymer electrolyte fuel cells having high power generation performance and excellent in durability can be provided.Type: GrantFiled: January 24, 2008Date of Patent: September 13, 2011Assignee: Asahi Glass Company, LimitedInventors: Tetsuji Shimohira, Kazuo Hamazaki, Susumu Saito, Satoru Hommura, Seigo Kotera
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Publication number: 20110217654Abstract: The invention pertains to a compound generating an acid of the formula I or II, for instance corresponding sulfonium and iodonium salts, as well as corresponding sulfonyloximes wherein X is CH2 or CO; Y is O, NR4, S, O(CO), O(CO)O, O(CO)NR4, OSO2, O(CS), or O(CS)NR4; R1 is for example C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, interrupted C2-C18alkyl, interrupted C3-C30cycloalkyl, interrupted C3-C30cycloalkyl-C1-C18alkyl, interrupted C4-C30cycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or heteroaryl, all unsubstituted or are substituted; or R1 is NR12R13; R2 and R3 are for example C3-C30cycloalkylene, C3-C30cycloalkyl-C1-C18alkylene, C1-C18alkylene, C1-C10haloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or heteroarylene; all unsubstituted or substituted; R4 is for example C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alType: ApplicationFiled: February 16, 2011Publication date: September 8, 2011Applicant: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Keita Tanaka, Yuichi Nishimae
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Publication number: 20110212391Abstract: A polymer comprising recurring units having a fluorinated carboxylic acid onium salt structure on a side chain is used to formulate a chemically amplified positive resist composition. When the composition is processed by lithography to form a positive pattern, the diffusion of acid in the resist film is uniform and slow, and the pattern is improved in LER.Type: ApplicationFiled: February 25, 2011Publication date: September 1, 2011Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Keiichi Masunaga, Satoshi Watanabe, Jun Hatakeyama, Youichi Ohsawa, Daisuke Domon
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Publication number: 20110200940Abstract: The present invention provides a salt represented by the formula (I): wherein R1 and R2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO— and which can have one or more fluorine atoms, R3 represents a hydrogen atom or a methyl group, and Z1+ represents an organic counter cation, and a photoresist composition containing the same.Type: ApplicationFiled: February 15, 2011Publication date: August 18, 2011Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventors: Koji ICHIKAWA, Hiromu SAKAMOTO
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Publication number: 20110196120Abstract: A stimuli responsive compound includes: a unit A having bonds that function as rotation axes; a first unit B disposed at a first bonding section of the unit A; a second unit B disposed at a second bonding section of the unit A; a first unit C disposed at a third bonding section of the unit A; and a second unit C disposed at a fourth bonding section of the unit A. The first unit B bonds with the second unit B by oxidation-reduction reaction, and the first unit C and the second unit C have liquid crystallinity and include polymerizable functional groups.Type: ApplicationFiled: February 2, 2011Publication date: August 11, 2011Applicant: SEIKO EPSON CORPORATIONInventor: Toshihiro OTAKE
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Publication number: 20110189607Abstract: 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: ApplicationFiled: January 25, 2011Publication date: August 4, 2011Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Masaki OHASHI, Satoshi WATANABE, Youichi OHSAWA, Keiichi MASUNAGA, Takeshi KINSHO
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Patent number: 7985818Abstract: Methods for removing safrole from a sample, molecular imprinted copolymers that bind safrole, and methods of making the same are provided.Type: GrantFiled: April 10, 2006Date of Patent: July 26, 2011Assignee: R.J. Reynolds Tobacco CompanyInventor: Svetlana I. Pertsovich