Fluorine-containing Monomer Contains A Sulfur Atom Patents (Class 526/243)
  • Publication number: 20140272707
    Abstract: A sulfonium salt having formula (1a) is provided wherein R1 is H, F, CH3 or CF3, R1a to R1m are each independently H or a monovalent hydrocarbon group, L is a single bond or divalent hydrocarbon group, X is a divalent alkylene group optionally substituted with fluorine, and n is 0 or 1. The sulfonium salt having a polymerizable anion provides for efficient scission of acid labile groups in a chemically amplified resist composition, and it is a very useful monomer from which a base resin for resist use is prepared.
    Type: Application
    Filed: February 4, 2014
    Publication date: September 18, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masahiro Fukushima, Jun Hatakeyama, Masaki Ohashi, Teppei Adachi
  • Publication number: 20140275400
    Abstract: The present invention provides methylene beta-diketone monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-diketones of the invention, a beta-diketone is reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-diketone monomer. The present invention further compositions and products formed from methylene beta-diketone monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).
    Type: Application
    Filed: October 18, 2012
    Publication date: September 18, 2014
    Inventors: Yangbin Chen, Adam G. Malofsky, Jeffrey M. Sullivan, Stanley C. Wojciak, Tanmoy Dey, Bernard M. Malofsky
  • Publication number: 20140255853
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component (A) which exhibits changed solubility in a developing solution under action of acid, the base component (A) including a polymeric compound (A1) containing a structural unit (a0) represented by general formula (a0-1) shown below. In the formula, W1 represents a group which is formed by polymerization reaction of a group containing a polymerizable group; Y1 and Y2 each independently represents a divalent linking group; Y3 represents a carbonyl group or an alkylene group; R2 and R3 each independently represents a fluorine atom or a fluorinated alkyl group; Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Application
    Filed: March 4, 2014
    Publication date: September 11, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Yoshiyuki Utsumi
  • Publication number: 20140256894
    Abstract: The present invention relates to solar cells and discloses a difluoro benzotriazolyl organic semiconductor material and preparation method and use thereof. The organic semiconductor material is represented by formula (I), wherein both R1 and R2 are C1 to C20 alkyl, and n is an integer from 10 to 50. In the difluoro benzotriazolyl organic semiconductor material, since the 1,2,3-benzotriazole organic semiconductor material contains two fluorine atoms, the HOMO energy level is reduced by 0.11 eV, while the fluorine-substituted 1,2,3-benzotriazole has two imido groups with electron-withdrawing ability; the fluorine-substituted 1,2,3-benzotriazole is a heterocyclic compound with strong electron-withdrawing ability, and an alkyl chain can be easily introduced to the N-position of the N—H bond of the benzotriazole. The functional group of the alkyl chain can improve the solar energy conversion efficiency, thus solving the low efficiency problem of solar cells made of the organic semiconductor material.
    Type: Application
    Filed: September 23, 2011
    Publication date: September 11, 2014
    Applicant: OCEAN'S KING LIGHTING SCIENCE & TECHNOLOGY CO., LTD.
    Inventors: Mingjie Zhou, Ping Wang, Zhenhua Zhang, Jixing Chen
  • Patent number: 8829131
    Abstract: 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: Grant
    Filed: July 13, 2010
    Date of Patent: September 9, 2014
    Assignees: Commissariat a l'Energie Atomique et Aux Energies Alternatives, Centre National de la Recherche Scientifique
    Inventors: Aurélien Soules, Bruno Ameduri, Bernard Boutevin, Hervé Galiano
  • Patent number: 8822588
    Abstract: A fluorine-containing polymer has a repeating unit of the general formula (2) and is produced by homopolymerization or copolymerization with another polymerizable double bond-containing monomer. In general formula (2), W represents a linking group; R1 each independently represents a perfluoroalkyl group; Q represents a unit structure formed by cleavage of a double bond of a polymerizable double bond-containing group; and M+ represents a hydrogen cation, a metal ion or a quaternary ammonium ion.
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: September 2, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yoshiharu Terui, Haruhiko Komoriya, Susumu Inoue, Takashi Kume
  • Publication number: 20140242519
    Abstract: A polymer for resist use is obtainable from a monomer having formula (1) wherein R1 is H, CH3 or CF3, R2 and R3 are a monovalent hydrocarbon group, R4 to R9 are hydrogen or a monovalent hydrocarbon group, R10 is a monovalent hydrocarbon group or fluorinated hydrocarbon group, A1 is a divalent hydrocarbon group, k1 is 0 or 1, and n1A is 0, 1 or 2. A resist composition comprising the polymer displays a high dissolution contrast during organic solvent development.
    Type: Application
    Filed: February 3, 2014
    Publication date: August 28, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8808966
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness. In formula (1), A is —(CR22)m—, B is —(CR52)n—, R2 and R5 are hydrogen or alkyl, m and n are 1 or 2, R3 is alkyl, alkenyl, alkynyl or aryl, R6 is alkyl, alkoxy, alkanoyl, alkoxycarbonyl, hydroxyl, nitro, aryl, halogen, or cyano, and p is 0 to 4.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: August 19, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Publication number: 20140212810
    Abstract: A polymer comprising recurring units (a) of styrene having an HFA group and an ester group adjacent thereto and recurring units (b) having a hydroxyl group is used as base resin to formulate a negative resist composition. The negative resist composition has a high dissolution contrast in alkaline developer, high sensitivity, high resolution, good pattern profile after exposure, and a suppressed acid diffusion rate.
    Type: Application
    Filed: December 23, 2013
    Publication date: July 31, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Daisuke Domon
  • Publication number: 20140212797
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes: (P) a resin that contains (A) a repeating unit capable of decomposing upon irradiation with an actinic ray or radiation to generate an acid in a side chain of the resin (P) and (C) a repeating unit represented by the following formula (I) as defined in the specification, wherein a polydispersity of the resin (P) is 1.20 or less.
    Type: Application
    Filed: March 28, 2014
    Publication date: July 31, 2014
    Applicant: FUJIFILM CORPORATION
    Inventors: Takeshi KAWABATA, Hideaki TSUBAKI
  • Patent number: 8785105
    Abstract: 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: Grant
    Filed: November 9, 2011
    Date of Patent: July 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
  • Publication number: 20140199631
    Abstract: 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: Application
    Filed: December 17, 2013
    Publication date: July 17, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8778595
    Abstract: A resist composition containing a base component (A) which generates acid upon exposure, and exhibits changed solubility in a developing solution under the action of acid, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below and a structural unit (a6) that generates acid upon exposure. In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R1 represents a sulfur atom or an oxygen atom, R2 represents a single bond or a divalent linking group, and Y represents a hydrocarbon group in which a carbon atom or a hydrogen atom may be substituted with a substituent.
    Type: Grant
    Filed: November 16, 2012
    Date of Patent: July 15, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Jun Iwashita
  • Publication number: 20140178820
    Abstract: An additive polymer comprising recurring styrene units having an ester group bonded to a CF3—C(OR2)—R3 group (wherein R2 is H, acyl or acid labile group, R3 is H, CH3 or CF3) such as 1,1,1,3,3,3-hexafluoro-2-propanol is added to a polymer capable of increasing alkali solubility under the action of acid to formulate a resist composition. The resist composition can minimize outgassing from a resist film during the EUV lithography and form a resist film having a hydrophilic surface sufficient to prevent formation of blob defects on the film after development.
    Type: Application
    Filed: December 9, 2013
    Publication date: June 26, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Kenji Funatsu
  • Publication number: 20140179888
    Abstract: 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: Application
    Filed: February 26, 2014
    Publication date: June 26, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Cheryl Lynn Iaconelli, Gerald Oronde Brown, Christopher James Martin, Erick J. Acosta
  • Publication number: 20140162189
    Abstract: A sulfonium salt having formula (1a) is provided wherein R1 is H, F, CH3 or CF3, R1a to R1m are each independently H or a monovalent hydrocarbon group, L is a single bond or divalent hydrocarbon group, X is a divalent alkylene group optionally substituted with fluorine, and n is 0 or 1. The sulfonium salt having a polymerizable anion provides for efficient scission of acid labile groups in a chemically amplified resist composition, and it is a very useful monomer from which a base resin for resist use is prepared.
    Type: Application
    Filed: December 6, 2013
    Publication date: June 12, 2014
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Jun Hatakeyama, Teppei Adachi, Masahiro Fukushima
  • Publication number: 20140162188
    Abstract: A positive resist composition is provided comprising a polymer comprising recurring styrene units having an ester group bonded to a CF3—C(OH)—R3 group (R3?H, CH3, or CF3) such as 1,1,1,3,3,3-hexafluoro-2-propanol and having a Mw of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.
    Type: Application
    Filed: November 15, 2013
    Publication date: June 12, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Masaki Ohashi
  • Publication number: 20140142239
    Abstract: A compound of formula CF2?CFCF2OSF5 and polymers comprising recurring units deriving from CF2?CFCF2OSF5 are disclosed as well as processes for their preparation.
    Type: Application
    Filed: June 15, 2012
    Publication date: May 22, 2014
    Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Cristiano Monzani, Vito Tortelli
  • Patent number: 8722825
    Abstract: A polymer comprises the polymerized product of monomers comprising a nitrogen-containing monomer comprising formula (Ia), formula (Ib), or a combination of formulas (Ia) and (Ib), and an acid-deprotectable monomer having the formula (II): wherein a is 0 or 1, each Ra is independently H, F, C1-10 alkyl, or C1-10 fluoroalkyl, L1 is a straight chain or branched C1-20 alkylene group, or a monocyclic, polycyclic, or fused polycyclic C3-20 cycloalkylene group, each Rb is independently H, C1-10 alkyl, C3-20 cycloalkyl, C3-20 heterocycloalkyl, an aliphatic C5-20 oxycarbonyl, or a C1-30 acyl group optionally including a heteroatom substituent group, where each Rb is separate or at least one Rb is attached to an adjacent Rb; LN is a nitrogen-containing monocyclic, polycyclic, or fused polycyclic C3-20 heterocycloalkylene group, and X is H, C1-10 alkyl, aliphatic C5-20 oxycarbonyl, or a C1-30 acyl group optionally including a heteroatom substituent group; and each Rc is independently C1-10 alkyl, C3-20 cycloalkyl, o
    Type: Grant
    Filed: May 29, 2012
    Date of Patent: May 13, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu, Cong Liu, Gerhard Pohlers, Cheng-bai Xu, George G. Barclay
  • Publication number: 20140128560
    Abstract: Described herein is a trifluorostyrene compound that can be used as a monomer to form crosslinkable polymers, and their use as polymer electrolyte membranes.
    Type: Application
    Filed: January 10, 2014
    Publication date: May 8, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Mark Gerrit Roelofs, MARK F. TEASLEY
  • Patent number: 8697824
    Abstract: The present invention is concerned with novel ion-exchange membranes, their method of preparation and their uses. The membranes are made of a polymer obtained from a monomer or a mixture of bifunctional monomers of general formula [T-SO2—Y—SO2-T?]?M+. The polymers are useful in an alkali-chloride electrolysis process, as a separator in an electrochemical preparation of inorganic and organic compounds, as a separator between an aqueous and an organic phase, or as a catalyst for Diels-Alder additions, Friedel-Craft reactions, aldol condensations, cationic polymerizations, esterifications, and acetal formations.
    Type: Grant
    Filed: June 26, 2008
    Date of Patent: April 15, 2014
    Assignee: Hydro Quebec
    Inventors: Christophe Michot, Michel Armand
  • Publication number: 20140100344
    Abstract: To provide a process by which from a mixture containing a fluorinated copolymer, an unreacted monomer and a polymerization medium, the unreacted monomer and the polymerization medium can efficiently be recovered. A process for producing a fluorinated copolymer, which comprises (I) a step of polymerizing a fluorinated monomer having a carboxylic acid functional group or a sulfonic acid functional group and a fluorinated olefin in a polymerization medium to obtain a mixture containing a fluorinated copolymer, an unreacted monomer and the polymerization medium, and (II) a step of continuously or intermittently transferring the mixture to an evaporation vessel provided with a stirrer and heating it with stirring in the evaporation vessel to evaporate and recover the unreacted monomer and the polymerization medium.
    Type: Application
    Filed: December 6, 2013
    Publication date: April 10, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Shigeru AIDA, Toshinori Tomita, Toshinori Eto, Kazuo Umemura, Atsushi Tsuji
  • Publication number: 20140093824
    Abstract: A resist composition including a polymeric compound (A1) containing a structural unit (a0) represented by general formula (a0-1) and a structural unit (a6) which generates acid upon exposure, and a method of forming a resist pattern using the resist composition. In general formula (a0-1), R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Wa0 represents a single bond or an aliphatic hydrocarbon group having 1 to 5 carbon atoms and having a valency of (na0+1); Ra0 represents an aryl group of 4 to 16 carbon atoms which may have a substituent; and na0 represents 1 or 2.
    Type: Application
    Filed: October 1, 2013
    Publication date: April 3, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daisuke Kawana, Kenta Suzuki, Tatsuya Fujii, Jun Iwashita, Kenri Konno
  • Publication number: 20140093826
    Abstract: A composition for forming a liquid immersion upper layer film includes a polymer component including a polymer having a structural unit represented by a formula (1); and a solvent. R1 represents a carboxy group or a group represented by a formula (2); X represents a single bond, a divalent hydrocarbon group having 1 to 20 carbon atoms or a divalent fluorinated hydrocarbon group having 1 to 20 carbon atoms; R2 represents a hydrocarbon group having 1 to 20 carbon atoms and a valency of (n+1), a fluorinated hydrocarbon group having 1 to 20 carbon atoms and a valency of (n+1), or one of these groups each including between adjacent two carbon atoms thereof —CO—, —COO—, —O—, —NR?—, —CS—, —S—, —SO—, —SO2— or a combination thereof; and R3 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms.
    Type: Application
    Filed: September 20, 2013
    Publication date: April 3, 2014
    Applicant: JSR CORPORATION
    Inventors: Shinya MINEGISHI, Kiyoshi TANAKA, Kazunori KUSABIRAKI
  • Publication number: 20140093823
    Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography.
    Type: Application
    Filed: September 27, 2013
    Publication date: April 3, 2014
    Inventors: Robert L. BRAINARD, Shinya AKIBA, Ryo NADANO, Kenji HOSOI, Brian CARDINEAU
  • Patent number: 8686098
    Abstract: 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: Grant
    Filed: May 20, 2010
    Date of Patent: April 1, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Yuji Hagiwara, Masashi Nagamori, Yoshimi Isono, Satoru Narizuka, Kazuhiko Maeda
  • Publication number: 20140080064
    Abstract: A pattern is printed by forming a photoresist layer on a wafer, forming a protective film thereon, exposure, and development. The protective film is formed from a composition comprising a copolymer comprising recurring units derived from a styrene, indene, benzofuran or benzothiophene monomer having 1,1,1,3,3,3-hexafluoro-2-propanol, and recurring units derived from a styrene, vinylnaphthalene, indene, benzofuran, benzothiophene, stilbene, styrylnaphthalene or dinaphthylethylene monomer and an ether solvent.
    Type: Application
    Filed: September 10, 2013
    Publication date: March 20, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventor: Jun Hatakeyama
  • Patent number: 8669319
    Abstract: A polymer is provided comprising a first pendant group selected from at least one of a perfluorinated ether group or a perfluoroalkanesulfonamido group, a second pendant group comprising an ammonium group, wherein the second pendant group is free of silicon, and a third pendant group comprising an ammonium group and a reactive silicon-containing group. A composition comprising the polymer is provided. The polymer and composition are useful for protecting a substrate, for example, to render the substrate oil repellent, water repellent, or both, or to provide stain repellency to the substrate.
    Type: Grant
    Filed: December 10, 2012
    Date of Patent: March 11, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Rudolf J. Dams, Suresh S. Iyer, Chetan P. Jariwala, Thomas P. Klun, Inge Nuyts
  • Publication number: 20140065550
    Abstract: A polymer comprises the polymerized product of unsaturated monomers comprising an acid-deprotectable monomer, a base-soluble monomer, a lactone-containing monomer, a photoacid-generating monomer, or a combination comprising at least one of the foregoing monomers, with a chain transfer agent of Formula (I); wherein in Formula (I), Z is a y valent C1-20 organic group, L is a heteroatom or a single bond, A1 and A2 are each independently ester containing or non-ester containing and are fluorinated or non-fluorinated, and are independently C1-40 alkylene, C3-40 cycloalkylene, C6-40 arylene, or C7-40 aralkylene, and A1 contains a nitrile, ester, or aryl substituent group alpha to the point of attachment with sulfur, X1 is a single bond, —O—, —S—, —C(?O)—O—, —O—C(?O)—, —O—C(?O)—O—, —C(?O)—NR—, —NR—C(?O)—, —NR—C(?O)—NR—, —S(?O)2—O—, —O—S(?O)2—O—, —NR—S(?O)2—, or —S(?O)2—NR, wherein R is H, C1-10 alkyl, C3-10 cycloalkyl or C6-10 aryl, Y? is an anionic group, G+ is a metallic or non-metallic cation, and y is an int
    Type: Application
    Filed: August 28, 2013
    Publication date: March 6, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: John W. Kramer, Daniel J. Arriola
  • Patent number: 8663897
    Abstract: According to the present invention, there is provided a polymerizable fluorine-containing sulfonic acid onium salt of the following general formula (2) and a resin obtained by polymerization thereof. It is possible by the use of this sulfonate resin of the present invention to provide a resist composition with high resolution, board depth of focus tolerance (DOF), small line edge roughness (LER) and high sensitivity. In the formula, Z represents a substituted or unsubstituted C1-C6 straight or branched alkylene group, or a divalent moiety in which substituted or unsubstituted C1-C6 straight or branched alkylene groups are bonded in series to a divalent group obtained by elimination of two hydrogen atoms from an alicyclic or aromatic hydrocarbon; R represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl or fluorine-containing alkyl group; and Q+ represents a sulfonium cation or an iodonium cation.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: March 4, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Takashi Masubuchi, Kazunori Mori, Yuji Hagiwara, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8658746
    Abstract: To provide an electrolyte polymer for polymer electrolyte fuel cells, made of a perfluorinated polymer having sulfonic groups, characterized in that in a test of immersing 0.1 g of the polymer in 50 g of a fenton reagent solution containing 3% of an aqueous hydrogen peroxide solution and 200 ppm of bivalent iron ions at 40° C. for 16 hours, the amount of eluted fluorine ions detected in the solution is not more than 0.002% of the total amount of fluorine in the polymer immersed. The electrolyte polymer of the present invention has very few unstable terminal groups and has an excellent durability, and therefore, is suitable as a polymer constituting an electrolyte membrane for polymer electrolyte fuel cells and a polymer contained in a catalyst layer.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: February 25, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Nobuyuki Kasahara, Atsushi Watakabe, Tetsuji Shimohira, Hisao Kawazoe, Ichiro Terada
  • Publication number: 20140050978
    Abstract: Provided are an additive for positive electrodes, which is capable of increasing the output of a lithium secondary battery and is capable of maintaining cycle characteristics even during high-speed charge and discharge; and a positive electrode for lithium secondary batteries. The additive for positive electrodes of lithium secondary batteries, which contains, as an essential constituent, a substituted polythiophene that has a repeating unit, which is obtained by substituting a hydrogen atom in the 3-position and/or in the 4-position of a thiophene ring with at least one group that is selected from the group consisting of a perfloroalkylalkoxy group, a perfloroalkoxy group, a perfloroalkoxyalkyl group and an alkyl group substituted with the perfloroalkylalkoxy group, as at least a part of a thiophene repeating group.
    Type: Application
    Filed: January 12, 2012
    Publication date: February 20, 2014
    Applicant: PLEXTRONICS, INC.
    Inventors: Takeshi Otaka, Bunpei Yoshida, Atsushi Wakatsuki, Takuma Takeda
  • Patent number: 8653019
    Abstract: A stain remover which comprises a copolymer made from as essential ingredients (a) a polymerizable monomer having a polyfluoroalkyl group with less than 8 carbon atoms and represented by the general formula H2C?CXCOO—Y—Rf and (b) a fluorine-free polymerizable monomer represented by the following general formula: H2C?CXCOO—(RO)n—X. The stain remover is effective in minimizing the amount of an organic solvent to be used. It imparts to a substrate the excellent property of removing stains therefrom and a satisfactory texture.
    Type: Grant
    Filed: July 10, 2009
    Date of Patent: February 18, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Fumihiko Yamaguchi, Masashi Nanri, Kazunori Hayashi
  • Publication number: 20140017617
    Abstract: A method of producing an ammonium salt compound, including reacting a first ammonium salt compound containing a first ammonium cation which is a primary, secondary or tertiary ammonium cation with a nitrogen-containing compound having a lone pair to obtain a second ammonium salt compound which contains a conjugated acid of the nitrogen-containing compound, the conjugated acid of the nitrogen-containing compound having a larger pKa than the pKa of the first ammonium cation; and a method of producing a compound, including a step of salt exchange between the ammonium salt compound obtained by the aforementioned production method and a sulfonium cation or iodonium cation which has a higher hydrophobicity than the hydrophobicity of the conjugated acid of the nitrogen-containing compound.
    Type: Application
    Filed: July 8, 2013
    Publication date: January 16, 2014
    Inventors: Masatoshi Arai, Yoshiyuki Utsumi
  • Patent number: 8617765
    Abstract: Ionomeric polymers that are chemically stabilized and contain inorganic fillers are prepared, and show reduced degradation. The ionomers care useful in membranes and electrochemical cells.
    Type: Grant
    Filed: December 21, 2006
    Date of Patent: December 31, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventor: Mark Gerrit Roelofs
  • Publication number: 20130344442
    Abstract: A polymer comprising recurring units of butyrolactone (meth)acrylate, recurring units having a carboxyl or phenolic group which is substituted with an acid labile group, and recurring units having a phenol group or an adhesive group in the form of 2,2,2-trifluoro-1-hydroxyethyl is quite effective as a base resin for resist. A positive resist composition comprising the polymer is improved in such properties as a contrast of alkali dissolution rate before and after exposure, acid diffusion suppressing effect, resolution, and profile and edge roughness of a pattern after exposure.
    Type: Application
    Filed: June 17, 2013
    Publication date: December 26, 2013
    Inventors: Masayoshi Sagehashi, Jun Hatakeyama, Koji Hasegawa
  • Publication number: 20130344441
    Abstract: Provided is a hydrophobic negative tone developable (NTD) resist composition comprising (a) a hydrophobic polymer having (i) at least one nonpolar acid-stable group; and (ii) at least one nonpolar acid-labile group, and (b) a photoacid generator (PAG) that may or may not be bound to the polymer, wherein a nonpolar aromatic or aliphatic organic hydrocarbon solvent is used to develop the unexposed regions of the NTD resist film and the resist film is not developable in an aqueous base developer, such as 0.26 N TMAH.
    Type: Application
    Filed: June 21, 2012
    Publication date: December 26, 2013
    Applicant: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: RATNAM SOORIYAKUMARAN, LINDA K. SUNDBERG, ANKIT VORA
  • Patent number: 8614275
    Abstract: A composition comprises a polymer having a first pendant group selected from at least one perfluorinated ether group or perfluoroalkanesulfonamido group, a second pendant group comprising an ammonium group, wherein the second pendant group is free of silicon, and a third pendant group comprising an ammonium group and a reactive silicon-containing group. The polymer and composition are useful for protecting a substrate, for example, to render the substrate oil repellent, water repellent, or both, or to provide stain repellency to the substrate.
    Type: Grant
    Filed: February 18, 2013
    Date of Patent: December 24, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Rudolf J. Dams, Thomas P. Klun, Inge Nuyts
  • Publication number: 20130337387
    Abstract: A resist composition including a base component (A) which generates acid upon exposure and exhibits changed solubility in a developing solution by the action of acid, (A) including (A1) including (a0) and (a2), and the resist composition having a Tf temperature of lower than 170° C. (?La01 represents —COO—, —CON(R?)— or a divalent aromatic group, R? represents a hydrogen atom or a methyl group, Va01 represents a linear alkylene group of at least 3 carbon atoms, A? represents an anion-containing group, Mm+ represents an organic cation, Ya21 represents a single bond or divalent linking group, La21 represents —O—, —COO—, —CON(R?)— or —OCO—, R? represents a hydrogen atom or a methyl group, and Ra21 represents a lactone-containing group, a carbonate containing group or an —SO2— containing group.
    Type: Application
    Filed: April 23, 2013
    Publication date: December 19, 2013
    Applicant: Tokyo Ohta Kogyo Co., Ltd.
    Inventor: Tokyo Ohta Kogyo Co., Ltd.
  • Publication number: 20130337378
    Abstract: A sulfonium salt comprising (a) a polymerizable substituent, (b) a sulfonium cation, and (c) a sulfonate anion within a common molecule is capable of generating a sulfonic acid in response to high-energy radiation or heat. A resist composition comprising the sulfonium salt as base resin has high resolution and is suited for precise micropatterning by ArF immersion, EB or EUV lithography.
    Type: Application
    Filed: May 30, 2013
    Publication date: December 19, 2013
    Inventors: Masaki Ohashi, Jun Hatakeyama
  • Publication number: 20130323646
    Abstract: A polymer is obtained from copolymerization of a unit having a carboxyl and/or phenolic hydroxyl group substituted with an acid labile group with a hydroxyphenyl methacrylate unit having one acyl, acyloxy or alkoxycarbonyl group. The polymer is useful as a base resin in a positive resist composition. The resist composition comprising the polymer is improved in contrast of alkali dissolution rate before and after exposure, acid diffusion control, resolution, and profile and edge roughness of a pattern after exposure.
    Type: Application
    Filed: May 9, 2013
    Publication date: December 5, 2013
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masayoshi Sagehashi
  • Patent number: 8597855
    Abstract: An electrolyte material, which comprises a polymer (H) having ion exchange groups converted from precursor groups in a polymer (F) having repeating units (A) having a precursor group represented by the formula (g1) and repeating units (B) based on a perfluoromonomer having a 5-membered ring, and having a density of at most 2.03 g/cm3, the polymer (H) having an ion exchange capacity of from 1.3 to 2.3 meq/g dry resin: wherein Q1 and Q2 are a perfluoroalkylene group having an etheric oxygen atom, or the like, and Y is F or the like; the electrolyte material being suitable for a catalyst layer of the membrane/electrode assembly; the membrane/electrode assembly being excellent in power generation characteristics under low or no humidity conditions and under high humidity conditions.
    Type: Grant
    Filed: July 26, 2010
    Date of Patent: December 3, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoru Hommura, Susumu Saito, Tetsuji Shimohira, Atsushi Watakabe
  • Patent number: 8598305
    Abstract: 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: Grant
    Filed: March 15, 2011
    Date of Patent: December 3, 2013
    Assignees: Northwestern University, Polyera Corporation
    Inventors: Antonio Facchetti, Tobin J. Marks, Hui Huang, Zhihua Chen
  • Patent number: 8598290
    Abstract: The present invention provides a method of producing a fluoroelastomer excellent in dispersion stability at low cost, at a high rate of polymerization and in high yields. The present invention is a method of producing a fluoroelastomer comprising an emulsion polymerization of a fluorinated monomer in the presence of a water-soluble radical polymerization initiator, wherein the emulsion polymerization is carried out in the presence of a compound (1) containing a functional group reactive in radical polymerization and a hydrophilic group and a fluorinated compound (2) containing a fluorocarbon group comprising 1 to 6 continuously united carbon atom with fluorine atom directly bound to each of them as well as a hydrophilic group.
    Type: Grant
    Filed: June 29, 2007
    Date of Patent: December 3, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Mitsuru Kishine, Masanori Kitaichi, Yousuke Nishimura, Manabu Fujisawa, Yoshiki Tanaka, Shintarou Ogata, Yutaka Ueta, Shigeru Morita
  • Patent number: 8592540
    Abstract: There is disclosed a fluorine-containing polymer compound comprising a repeating unit (a) of the following general formula (2) and having a weight-average molecular weight of 1000 to 1000000 where R1 represents a polymerizable double bond-containing group; R2 represents a fluorine atom or a fluorine-containing alkyl group; R3 represents a hydrogen atom, an acid labile group, a cross-linking site or the other monovalent organic group; and W1 represents a linking moiety. When the fluorine-containing polymer compound is used in a resist compound for pattern formation by high energy radiation of 300 nm or less wavelength or electron beam radiation, it is possible to form a resist pattern with a good rectangular profile.
    Type: Grant
    Filed: December 15, 2009
    Date of Patent: November 26, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Yuji Hagiwara, Yoshimi Isono, Satoru Narizuka, Kazuhiko Maeda
  • Publication number: 20130288180
    Abstract: A polymer for use in resist compositions is obtained from a monomer having formula (1) wherein R1 is methyl, ethyl, propyl, vinyl or ethynyl, the circle designates C3-C12 cycloalkyl, a combination wherein R1 is ethyl and the circle is cyclohexyl being excluded, R2 is H or C1-C4 alkyl, and m is 1 to 4.
    Type: Application
    Filed: April 3, 2013
    Publication date: October 31, 2013
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8557474
    Abstract: A fluorosulfonyl group-containing monomer having a high polymerization reactivity and plural fluorosulfonyl groups, a fluorosulfonyl group-containing polymer and a sulfonic acid group-containing polymer, obtained by using the monomer.
    Type: Grant
    Filed: November 29, 2010
    Date of Patent: October 15, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Atsushi Watakabe, Hiromasa Yamamoto, Masao Iwaya, Susumu Saito
  • Publication number: 20130260313
    Abstract: A photoacid generating polymer (PAG polymer) comprises i) a first repeat unit of capable of reacting with a photogenerated acid to form a carboxylic acid containing repeat unit, ii) a second repeat unit of capable of forming the photogenerated acid, and iii) a third repeat unit comprising a norbornyl ester, wherein a norbornyl ring of the norbornyl ester comprises a monovalent substituent having the formula *-L?-C(CF3)2(OH). L? is a divalent linking group comprising at least one carbon and the starred bond of L? is linked to the norbornyl ring. The first repeat unit, second repeat unit, and the third repeat unit are covalently bound repeat units of the PAG polymer.
    Type: Application
    Filed: March 31, 2012
    Publication date: October 3, 2013
    Applicants: CENTRAL GLASS CO., LTD., INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Robert David Allen, Phillip Joe Brock, Masaki Fujiwara, Kazuhiko Maeda, Hoa D. Truong
  • Publication number: 20130251930
    Abstract: Described herein is a composition having a fluoropolymer derived from the polymerization of a monomer and a sulfinate-containing molecule, wherein the sulfinate-containing molecule is selected from the group consisting of Formula (I), Formula (II); and combinations thereof, wherein X1, X2, and X3 are each independently selected from H, F, Cl, a C1 to C4 alkyl group, and a C1 to C4 fluorinated alkyl group; R is a linking group; Z1 and Z2 are independently selected from F, CF3, and a perfluoroalkyl group; R1 and R2 are end-groups; p is 0 or 1; m is at least 1; and M is a cation. Also disclosed are methods of making and articles thereof.
    Type: Application
    Filed: December 16, 2011
    Publication date: September 26, 2013
    Inventors: Gregg D. Dahlke, Denis Duchesne, Tatsuo Fukushi, Werner M. Grootaert, Miguel A. Guerra, Harald Kaspar, Larry A. Last, Peter J. Scott, Zai-Ming Qiu
  • Patent number: 8541523
    Abstract: Embodiments in accordance with the present invention provide for non-self imageable norbornene-type polymers useful for immersion lithographic processes, methods of making such polymers, compositions employing such polymers and immersion lithographic processes that make use of such compositions. More specifically the embodiments of the present invention are related to norbornene-type polymers useful for forming top-coat layers for overlying photoresist layers in immersion lithographic process and the process thereof.
    Type: Grant
    Filed: April 4, 2011
    Date of Patent: September 24, 2013
    Assignee: Promerus, LLC
    Inventors: Pramod Kandanarachchi, Kazuyoshi Fujita, Steven Smith, Larry F. Rhodes