Plural Chalcogens Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/110)
  • Patent number: 11879025
    Abstract: A method for removing perfluorinated compounds from a fluoropolymer material is provided. The method includes the steps of: (a) providing the fluoropolymer material in a chamber; (b) providing an anaerobic environment in the chamber; and (c) providing a fluorination gas in the chamber, thereby exposing the fluoropolymer material to the fluorination gas. The method results in the removal the perfluorinated compounds from the fluoropolymer material.
    Type: Grant
    Filed: April 23, 2021
    Date of Patent: January 23, 2024
    Assignee: Inhance Technologies, LLC
    Inventors: Subramanian Iyer, Andrew M. Thompson, Adrian R. Samaniego, Zhenshuo Liu
  • Patent number: 11840589
    Abstract: To provide a perfluoropolymer capable of producing an electrolyte membrane excellent in mechanical strength in high temperature environments; as well as a liquid composition, polymer electrolyte membrane, membrane electrode assembly and polymer electrolyte water electrolyzer, obtainable by using the perfluoropolymer. The perfluoropolymer of the present invention contains perfluoromonomer units, does not substantially contain units having a halogen atom other than a fluorine atom, does not substantially contain units having a ring structure, and has acid-type sulfonic acid groups, wherein the perfluoromonomer units contain at least one type of units A selected from the group consisting of perfluorovinyl ether units and perfluoroallyl ether units; the ion exchange capacity is from 0.9 to 1.4 milliequivalent/gram dry resin; and the storage modulus at 120° C. is at least 100 MPa.
    Type: Grant
    Filed: May 27, 2021
    Date of Patent: December 12, 2023
    Assignee: AGC Inc.
    Inventors: Takeshi Hirai, Daisuke Jomuta, Chikaya Tamitsuji
  • Patent number: 11820733
    Abstract: The present disclosure is directed to provide a process capable of producing a sulfonic acid group-containing monomer in a good yield, which can be used as a raw material of fluorine-based polymer electrolytes, such as membranes for fuel cells, catalyst binder polymers for fuel cells, and membranes for chlor-alkali electrolysis. A process for producing a sulfonic acid group-containing monomer represented by the general formula (3) includes the step of mixing and stirring a cyclic compound represented by the general formula (1) and a silanol compound represented by the general formula (2).
    Type: Grant
    Filed: February 13, 2019
    Date of Patent: November 21, 2023
    Assignee: ASAHI KASEI KABUSHIKI KAISHA
    Inventors: Nobuyuki Uematsu, Yasuhiro Nagato, Kaishi Hori, Kenichi Yakigaya
  • Patent number: 11649205
    Abstract: The present disclosure is directed to provide a vinylsulfonic anhydride which is useful as a synthetic intermediate for synthesis of a fluorinated monomer. It is also directed to efficiently produce the vinylsulfonic anhydride. It is further directed to efficiently produce a fluorinated monomer using the vinylsulfonic anhydride. A vinylsulfonic anhydride of the present disclosure is expressed by the general formula (1). Further, a process for producing a vinylsulfonic anhydride of the present disclosure includes making a vinylsulfonic acid compound represented by the general formula (2) come in contact and be mixed with an anhydridization agent.
    Type: Grant
    Filed: June 20, 2019
    Date of Patent: May 16, 2023
    Assignee: ASAHI KASEI KABUSHIKI KAISHA
    Inventors: Nobuyuki Uematsu, Hideki Date, Yasuhiro Nagato, Akitake Nakamura, Kenichi Yakigaya
  • Publication number: 20150087521
    Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.
    Type: Application
    Filed: March 13, 2013
    Publication date: March 26, 2015
    Applicant: Stepan Company
    Inventors: David R. Allen, Marcos Alonso, Mary Beddaoui, Randal J. Bernhardt, Aaron Brown, Scott Dillavou, Xue Min Dong, Wilma Gorman, John C. Hutchison, Gary Luebke, Renee Luka, Franz Luxem, Andrew D Malec, Ronald A. Masters, Dennis S. Murphy, Nicholas Pendleton, Irma Ryklin, Patti Skelton, Brian Sook, Chris Spaulding, Krista Turpin, Gregory Wallace, Michael Wiester, Patrick Shane Wolfe
  • Patent number: 8956799
    Abstract: A photoacid generator includes those of formula (I): wherein each Ra in formula 1 is independently H, F, a C1-10 nonfluorinated organic group, C1-10 fluorinated organic group, or a combination comprising at least one of the foregoing, provided at least one Ra is F or a C1-10 fluorinated organic group, the C1-10 fluorinated and nonfluorinated organic groups each optionally comprising O, S, N, or a combination comprising at least one of the foregoing heteroatoms; L1 is a linking group comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; G+ is an onium salt of the formula (II): wherein in formula (II), X is S or I, each R0 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 comprising at least one of the foregoing, provided at least one R0 is substituted where each R0 is a C6 monocyclic aryl group, and wherein when X is I, a is 2, and where X is S, a is 3,
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
  • Patent number: 8877962
    Abstract: The present invention provides a method for efficiently producing a sulfonic acid group-containing ether compound having a high purity and a good polymerizability while preventing production of a byproduct, and provides a sulfonic acid group-containing ether compound containing fewer impurities and having a good radical (co)polymerizability. The present invention provides a method of producing a sulfonic acid group-containing ether compound by reacting a sulfurous acid compound with a compound represented by the formula (1): wherein R1 represents a single bond, a CH2 group, or a CH2CH2 group, and R2 represents H, or a CH3 group, the method comprising the steps of: adjusting pH of a reaction system to 5.5 or greater with use of an alkaline substance; and adding the compound represented by the formula (1) to a reaction vessel containing the sulfurous acid compound.
    Type: Grant
    Filed: June 13, 2014
    Date of Patent: November 4, 2014
    Assignee: Nippon Shokubai Co, Ltd
    Inventors: Masato Nakano, Akihiko Kanzaki, Takahiro Tsumori
  • Publication number: 20140296565
    Abstract: The present invention provides a method for efficiently producing a sulfonic acid group-containing ether compound having a high purity and a good polymerizability while preventing production of a byproduct, and provides a sulfonic acid group-containing ether compound containing fewer impurities and having a good radical (co)polymerizability. The present invention provides a method of producing a sulfonic acid group-containing ether compound by reacting a sulfurous acid compound with a compound represented by the formula (1): wherein R1 represents a single bond, a CH2 group, or a CH2CH2 group, and R2 represents H, or a CH3 group, the method comprising the steps of: adjusting pH of a reaction system to 5.5 or greater with use of an alkaline substance; and adding the compound represented by the formula (1) to a reaction vessel containing the sulfurous acid compound.
    Type: Application
    Filed: June 13, 2014
    Publication date: October 2, 2014
    Inventors: Masato Nakano, Akihiko Kanzaki, Takahiro Tsumori
  • Patent number: 8835097
    Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
  • Publication number: 20140228530
    Abstract: An extended anionic surfactant having the general formula: RO—(PO)n—YZ wherein R is a linear alkyl chain ranging from C6 to C36, a branched alkyl chain ranging from C6 to C36, or a mixture thereof; PO is a propyleneoxy group; Y is —SO3, —CH2CH2CH2—SO3, —CH2CH(CH3)—SO3, or —CH2COO; Z is a cation; and n is 1 to 50.
    Type: Application
    Filed: August 24, 2012
    Publication date: August 14, 2014
    Inventors: Melanie Anne Sharp, Oliver Herzog, Sebastiano Giovanni Giordano, Teresa Linville Marino, Kip Douglas Sharp
  • Patent number: 8801939
    Abstract: A method for increasing ozone concentration in a liquid can include: providing a gas having ozone; introducing the ozone-containing gas into a liquid, wherein the liquid and ozone combination has a temperature between about 0.8 and about 1.5 times the critical temperature of ozone; and increasing isothermally, the pressure of the ozone-containing gas above the liquid to about 0.3 to about 5 times the critical pressure of ozone so as to increase the ozone concentration in the liquid. The temperature is expressed in absolute units (Kelvin or Rankin). The method can be used for removing ozone from a gas or for purifying ozone. The liquid having a high ozone concentration can be used for ozonolysis of a substrate.
    Type: Grant
    Filed: April 19, 2013
    Date of Patent: August 12, 2014
    Assignees: University of Kansas, Archer Daniels Midland Company
    Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P Binder
  • Patent number: 8791293
    Abstract: According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3). In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which “a moiety capable of changing its developer solubility by the action of an acid” and “a moiety having a photoacid generating function” are arranged with regularity.
    Type: Grant
    Filed: August 2, 2012
    Date of Patent: July 29, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
  • Publication number: 20140163255
    Abstract: The invention relates to a process for mineral oil production by means of Winsor Type III microemulsion flooding, in which an aqueous surfactant formulation comprising at least one ionic surfactant of the general formula R1—O—(CH2C(CH3)HO)m(CH2CH2O)n—XY?M+ is injected through injection boreholes into a mineral oil deposit, and crude oil is withdrawn from the deposit through production boreholes. The invention further relates to ionic surfactants of the general formula.
    Type: Application
    Filed: November 1, 2013
    Publication date: June 12, 2014
    Applicant: BASF SE
    Inventors: Christian Bittner, Günter Oetter, Jack Tinsley, Christian Spindler, Gabriela Alvarez-Juergenson, Sophie Maitro-Vogel, Veronika Wloka, Marcus Guzmann
  • Patent number: 8716519
    Abstract: The invention relates to novel cross-linkable monomers that may be polymerized with ethylenically unsaturated comonomers to form cross-linkable copolymers. Said copolymers may particularly be used in the form of aqueous dispersions as formaldehyde-free adhesives or as coatings with good water resistance.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: May 6, 2014
    Assignee: Celanese Emulsions GmbH
    Inventors: Martin Jakob, Stefan Nogai
  • Patent number: 8691490
    Abstract: 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: Grant
    Filed: January 25, 2011
    Date of Patent: April 8, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Satoshi Watanabe, Youichi Ohsawa, Keiichi Masunaga, Takeshi Kinsho
  • Patent number: 8597869
    Abstract: A sulfonium salt of a naphthyltetrahydrothiophenium cation having a fluoroalkoxy chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark/bright bias.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: December 3, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Takeshi Kinsho, Tomohiro Kobayashi
  • Publication number: 20130284048
    Abstract: 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: Application
    Filed: June 24, 2013
    Publication date: October 31, 2013
    Inventors: Alexander Borisovich Shtarov, Michael Joseph Michalczyk, Charles Kenneth Taylor
  • Patent number: 8557756
    Abstract: Provided are compositions containing a compatible mixture of a cationic surfactant and an anionic surfactant. A composition according to the invention comprises: (a) a first surfactant of formula I: wherein R, R1, R2, and R3 Y, X, and n are as defined below; (b) a second surfactant that is oppositely charged to the first surfactant.
    Type: Grant
    Filed: June 15, 2011
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Yongfu Wu, Cynthia L. Rand, Wanglin Yu, Irina V. Graf
  • Patent number: 8557500
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, L2 represents a single bond or a C1-C6 alkanediyl group in which one or more —CH2— can be replaced by —O— or —CO—, Y represents a C3-C18 alicyclic hydrocarbon group which can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O—, —CO— or —SO2—, and Z+ represents an organic counter ion.
    Type: Grant
    Filed: February 28, 2012
    Date of Patent: October 15, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
  • Publication number: 20130190417
    Abstract: The disclosure provides anionic Gemini surfactants comprising at least two carbonyl moieties and at least two aliphatic moieties. In some aspects, at least two of the aliphatic moieties comprise at least seven carbon atoms and at least one pair of conjugated carbon-to-carbon double bonds. The anionic Gemini surfactants are polymerizable and may be used to prepare triply periodic multiply continuous lyotropic phase and polymers thereof that substantially retain triply periodic multiply continuous lyotropic phase structure.
    Type: Application
    Filed: January 23, 2013
    Publication date: July 25, 2013
    Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventor: Wisconsin Alumni Research Foundation
  • Patent number: 8465668
    Abstract: Surfactants with polyether sulfonate structure, which have a propanonylsulfonic acid group as a head group, a process for preparing such surfactants and their use for tertiary mineral oil extraction.
    Type: Grant
    Filed: October 15, 2008
    Date of Patent: June 18, 2013
    Assignee: BASF SE
    Inventors: Christian Bittner, Oetter Günter, Ulrich Steinbrenner, Jürgen Huff, Marcus Guzmann
  • Patent number: 8425784
    Abstract: A method for increasing ozone concentration in a liquid can include: providing a gas having ozone; introducing the ozone-containing gas into a liquid, wherein the liquid and ozone combination has a temperature between about 0.8 and about 1.5 times the critical temperature of ozone; and increasing isothermally, the pressure of the ozone-containing gas above the liquid to about 0.3 to about 5 times the critical pressure of ozone so as to increase the ozone concentration in the liquid. The temperature is expressed in absolute units (Kelvin or Rankin). The method can be used for removing ozone from a gas or for purifying ozone. The liquid having a high ozone concentration can be used for ozonolysis of a substrate.
    Type: Grant
    Filed: November 4, 2008
    Date of Patent: April 23, 2013
    Assignees: University of Kansas, Archer Daniels Midland Company
    Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P. Binder
  • Publication number: 20130056357
    Abstract: Sulfonate-, sulfate-, or carboxylate-capped, alkoxylated anti-misting agents having the structure: R((AO)nX)m((AO)nH)p, and methods of suppressing mist from electrolyte solutions by adding a mist-suppressing amount of one or more compounds selected from the group consisting of compounds of the Formulas R((AO)nX)m((AO)nH)p and R3N+(CH3)2R4, and mixtures thereof, to electrolyte solutions.
    Type: Application
    Filed: November 5, 2012
    Publication date: March 7, 2013
    Applicant: Cognis IP Management GmbH
    Inventor: Cognis IP Management GmbH
  • Publication number: 20130029249
    Abstract: The description includes materials that may be useful for fuel cell applications such as in the manufacture of fuel cell electrodes, proton exchange membranes (PEM), as catalyst additives or in tie layers designed to be thermally and chemically robust while operating within a fuel cell's harsh environment at higher temperatures and to conduct protons, with significantly higher levels of bound acidic groups, while in a low hydration state. Methods of making the materials are also described.
    Type: Application
    Filed: March 23, 2011
    Publication date: January 31, 2013
    Applicant: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Steven Joseph Hamrock, Mark Steven Schaberg
  • Publication number: 20120328519
    Abstract: The present invention relates to the novel compound classes of dendritic polyglycerol sulfates and sultanates as well as to their production and use for the treatment of diseases, particularly inflammatory diseases, and to their use as selectin inhibitors and selectin indicators. The dendritic polyglycerol sulfates and sulfonates are also suitable for imaging diagnostics, particularly with respect to inflammatory diseases.
    Type: Application
    Filed: August 3, 2007
    Publication date: December 27, 2012
    Inventors: Rainer Haag, Jens Dernedde, Rudolf Tauber, Gesche Bernhard, Sven Enders, Heidemarie Weinhart, Arne Von Bonin, Ulrich Zügel, Holger Türk
  • Patent number: 8283491
    Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C40 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of a mono-valent cation.
    Type: Grant
    Filed: October 23, 2008
    Date of Patent: October 9, 2012
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Theresa Ann Denslow
  • Publication number: 20120238717
    Abstract: A composition is provided that contains an intermediate for a water-soluble monomer, wherein this intermediate is suitable for producing a water-soluble polyalkylene glycol-type monomer that has a polymerizable terminal double bond, and suitable for the production of water-soluble polymer, and moreover allows the high-yield production of water-soluble polymer. A process of producing this composition and a water-soluble monomer-containing composition obtained therefrom are also provided. A water-soluble monomer is also provided that can be used as a starting material for a water-soluble polymer that even at high hardnesses exhibits an excellent capacity to capture metal ions such as the calcium ion and magnesium ion, an excellent anti-gelation performance, an excellent anti-soil redeposition performance, a better anti-dye transfer performance than in the past, and also an excellent compatibility with surfactants.
    Type: Application
    Filed: December 3, 2010
    Publication date: September 20, 2012
    Applicant: NIPPON SHOKUBAI CO., LTD.
    Inventors: Atsuro Yoneda, Makoto Saito, Aki Tsukajima, Daisuke Michitaka, Mitsuaki Makino
  • Publication number: 20120220502
    Abstract: The present invention is directed to the use of alkylalkoxysulfonates for the production of foams, which are stable at high temperatures, e.g. up to about 250° C. Furthermore, the invention relates to a method for producing of high temperature stable foams by using a foamable aqueous composition comprising at least one linear alkylalkoxysulfonate.
    Type: Application
    Filed: February 24, 2012
    Publication date: August 30, 2012
    Applicant: BASF SE
    Inventors: Gabriela Alvarez Jürgenson, Günter Oetter, Vandana Kurkal-Siebert, Marta Reinoso Garcia, Stefan Stein, Geza Horvath Szabo
  • Patent number: 8247160
    Abstract: A resist composition including a base component that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator consisting of a compound represented by general formula (b1). In formula (b1), Y1 represents a fluorinated alkylene group of 1 to 4 carbon atoms, X represents an aliphatic cyclic group of 3 to 30 carbon atoms, R11? to R13? each represents an aryl group or alkyl group, provided that at least one of R11? to R13? is an aryl group having a substituent represented by general formula (b1-0), and two alkyl groups among R11? to R13? may be bonded to each other to form a ring with the sulfur atom in the formula. In formula (b1-0), R52 represents a chain-like or cyclic hydrocarbon group, and f and g each represents 0 or 1.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Publication number: 20120203030
    Abstract: A photoacid generator represented by the following formula (1), a method for producing the photoacid generator, and a resist composition containing the photoacid generator are provided. wherein in the formula (1), Y, X, R1, R2, n1, n2 and A+ have the same meanings as defined in the detailed description of the invention. The photoacid generator can maintain an appropriate contact angle at the time of ArF liquid immersion lithography, can reduce defects occurring during liquid immersion lithography, and has excellent solubility in resist solvents and excellent compatibility with resins. Furthermore, the photoacid generator can be produced by an efficient and simple method using an epoxy compound that is industrially easily available.
    Type: Application
    Filed: February 7, 2012
    Publication date: August 9, 2012
    Applicant: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon OH, Dae Kyung Yoon, Yong Hwa Hong, Seung Duk Cho
  • Patent number: 8232423
    Abstract: Anionic acid-labile surfactants may generally comprise compounds represented by the formula: wherein R1 is independently selected from —(CH2)0-9CH3, R2 is selected from the group consisting of —H and —(CH2)0-5CH3, Y is an anion, X is a cation, and n is an integer from 1 to 8. Methods of making and using the anionic acid-labile surfactants are also described. The anionic acid-labile surfactants may be used to facilitate the solubilization of proteins and other molecules in an aqueous environment.
    Type: Grant
    Filed: August 1, 2011
    Date of Patent: July 31, 2012
    Assignee: Protea Biosciences, Inc.
    Inventors: Matthew Jacob Powell, Trust Tariro Razunguzwa, George Augustine O'Doherty, Miaosheng Li
  • Publication number: 20120129793
    Abstract: The present application describes compounds of Formula I and Formula IA and as disclosed herein, that are useful as anti-microbial agents, including as antibacterial, disinfectant, antifungal, germicidal or antiviral agents.
    Type: Application
    Filed: October 18, 2011
    Publication date: May 24, 2012
    Inventors: Rakesh K. Jain, Timothy Shiau, Charles Francavilla, Eddy Low, Eric Douglas Turtle, Donogh John Roger O'Mahony
  • Publication number: 20120053057
    Abstract: The present invention provides an amphiphile of the formula (I) as described hereinafter. The invention further relates to a process for preparing the amphiphile and to a composition comprising the amphiphile and a sparingly water-soluble active ingredient. It further relates to a process for producing the composition by contacting the amphiphile and the active ingredient, and to the use of the amphiphile for solubilizing a sparingly water-soluble active ingredient in aqueous solutions. The invention also relates to the use of the amphiphile in an agrochemical formulation comprising the amphiphile and a pesticide for controlling phytopathogenic fungi and/or unwanted vegetation and/or unwanted insect or mite infestation and/or for regulating the growth of plants, and finally to plant propagation material comprising the amphiphile.
    Type: Application
    Filed: August 31, 2011
    Publication date: March 1, 2012
    Applicant: BASF SE
    Inventors: Anna CRISTADORO, Holger TÜRK, Michael ISHAQUE, Rabie AL-HELLANI
  • Publication number: 20120004365
    Abstract: A composition comprising a mixture of fluoropolyether acids or salts having a number average value of about 800 to about 2500 g/mol. The amount of fluoropolyether acids or salt in the mixture having a molecular weight of not more than 500 g/mol is not more than 50 ppm by weight of the total amount of fluoropolyether acids or salts in the mixture. The amount of fluoropolyether acids or salts in the mixture having a molecular weight of 2500 g/mol or greater is not more than 40% by weight of the total amount of fluoropolyether acids or salts in the mixture. Preferably the fluoropolyether acids or salts comprise an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion and phosphonate. Also disclosed is an aqueous dispersion polymerization process for fluoropolymer manufacture employing polymerization agent comprising the specified mixture of fluoropolyether acids or salts.
    Type: Application
    Filed: September 13, 2011
    Publication date: January 5, 2012
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Gregory Allen Chapman, Jon Lee Howell, Adam Paul Smith
  • Publication number: 20110282096
    Abstract: Anionic acid-labile surfactants may generally comprise compounds represented by the formula: wherein R1 is independently selected from —(CH2)0-9CH3, R2 is selected from the group consisting of —H and —(CH2)0-5CH3, Y is an anion, X is a cation, and n is an integer from 1 to 8. Methods of making and using the anionic acid-labile surfactants are also described. The anionic acid-labile surfactants may be used to facilitate the solubilisation of proteins and other molecules in an aqueous environment.
    Type: Application
    Filed: August 1, 2011
    Publication date: November 17, 2011
    Inventors: Matthew Jacob Powell, Trust Tariro Razunguzwa, George Augustine O'Doherty, Miaosheng Li
  • Publication number: 20110281779
    Abstract: Compositions and methods of synthesis of anionic surfactants by alkoxylation of a Guerbet alcohol (GA) having 12 to 36 carbon atoms using butylene oxide, and optionally propylene oxide and/or ethylene oxide followed by the incorporation of a terminal anionic group are described herein. The GA of the present invention is made by a facile and inexpensive method that involves high temperature base catalyzed dimerization of alcohols with 6 to 18 carbon atoms. The large hydrophobe ether surfactants of the present invention find uses in enhanced oil recovery (EOR) applications where it is used for solubilization and mobilization of oil and for environmental cleanup. Further, the hydrophobe alkoxylated GA without anionic terminal group can be used as an ultra-high molecular weight non-ionic surfactant.
    Type: Application
    Filed: April 12, 2011
    Publication date: November 17, 2011
    Applicants: BASF SE, Board of Regents, The University of Texas System
    Inventors: Upali P. Weerasooriya, Gary A. Pope, Christian Bittner, Gunter Oetter, Jack F. Tinsley, Christian Spindler, Gabriela Alvarez Jurgenson, Sophie Maitro-Vogel
  • Patent number: 8057985
    Abstract: 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: Grant
    Filed: August 27, 2009
    Date of Patent: November 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
  • Patent number: 8053596
    Abstract: A process for preparing alkyl glyceryl sulfonate includes fractionally distilling an alkyl glyceryl epoxide mixture to afford alkyl glyceryl epoxide of formula IV: where R is a C4-12 alkyl, in at least about 98.0% purity by weight with respect to epoxidized compounds, the epoxidized compounds comprising the alkyl glyceryl epoxide of formula IV, dimer alkyl glyceryl epoxide of formula V, and trimer alkyl glyceryl epoxide of formula VI: where R is a C4-12 alkyl; and reacting the at least about 98.0% alkyl glyceryl epoxide of formula IV with a mixture of an alkali bisulfite and an alkali sulfite in a sulfonation reaction at a temperature, to afford the alkyl glyceryl sulfonate of formula I: where R is a C4-12 alkyl and M is an alkali metal.
    Type: Grant
    Filed: November 2, 2009
    Date of Patent: November 8, 2011
    Assignee: Third Stream Bioscience, Inc.
    Inventors: Dennis Neigel, Michael Calhoun, Ed Richman
  • Publication number: 20110237676
    Abstract: Provided herein are new spermicidal compositions that include one or more fluorous surfactants, e.g., non-ionic fluorous surfactants, anionic fluorous surfactants, cationic fluorous surfactants, and combinations thereof. Also provided are methods of preventing fertilization of an ovum, which include a step of contacting at least one spermatozoon with one or more fluorous surfactants. Additionally described herein are methods of preventing infection, which include a step of contacting at least one infectious pathogenic microorganism with one or more fluorous surfactants. Numerous fluorine-containing surfactants are demonstrated to be efficacious as human spermicides.
    Type: Application
    Filed: August 20, 2008
    Publication date: September 29, 2011
    Applicant: LEHIGH UNIVERSITY
    Inventors: Barry Bean, Robert A Flowers, Jennifer J Venditti, Rajni Singh
  • Publication number: 20110105787
    Abstract: A process for preparing alkyl glyceryl sulfonate includes fractionally distilling an alkyl glyceryl epoxide mixture to afford alkyl glyceryl epoxide of formula IV: where R is a C4-12 alkyl, in at least about 98.0% purity by weight with respect to epoxidized compounds, the epoxidized compounds comprising the alkyl glyceryl epoxide of formula IV, dimer alkyl glyceryl epoxide of formula V, and trimer alkyl glyceryl epoxide of formula VI: where R is a C4-12 alkyl; and reacting the at least about 98.0% alkyl glyceryl epoxide of formula IV with a mixture of an alkali bisulfite and an alkali sulfite in a sulfonation reaction at a temperature, to afford the alkyl glyceryl sulfonate of formula I: where R is a C4-12 alkyl and M is an alkali metal.
    Type: Application
    Filed: November 2, 2009
    Publication date: May 5, 2011
    Inventors: Dennis V. Neigel, Michael Calhoun, Ed Richman
  • Publication number: 20110070544
    Abstract: 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: Application
    Filed: March 10, 2009
    Publication date: March 24, 2011
    Applicant: Central Glass Company,Ltd.
    Inventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
  • Publication number: 20110039203
    Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.
    Type: Application
    Filed: October 21, 2010
    Publication date: February 17, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: CHRISTOPHER P. JUNK, MARK ANDREW HARMER, ANDREW EDWARD FEIRING, FRANK LEONARD SCHADT, III, ZOE SCHNEPP
  • Publication number: 20110015111
    Abstract: Provided are new anionic surfactants and methods of their preparation and use. The surfactants are compounds of the formula I: wherein R, R1, R2, R3, R4, R5, and R6 are as defined herein.
    Type: Application
    Filed: June 30, 2010
    Publication date: January 20, 2011
    Inventors: Wanglin Yu, Cynthia L. Rand, Edward D. Daugs, Yang Cheng, Irina V. Graf, Andre B. Argenton, Kari S. Phillipson
  • Patent number: 7569326
    Abstract: A sulfonium salt having a polymerizable anion generates a strong sulfonic acid upon exposure to high-energy radiation so that it facilitates effective scission of acid labile groups in chemically amplified resist compositions. It is useful as a monomer from which a base resin for use in radiation-sensitive resist compositions is derived.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
  • Publication number: 20090118498
    Abstract: A method for increasing ozone concentration in a liquid can include: providing a gas having ozone; introducing the ozone-containing gas into a liquid, wherein the liquid and ozone combination has a temperature between about 0.8 and about 1.5 times the critical temperature of ozone; and increasing isothermally, the pressure of the ozone-containing gas above the liquid to about 0.3 to about 5 times the critical pressure of ozone so as to increase the ozone concentration in the liquid. The temperature is expressed in absolute units (Kelvin or Rankin). The method can be used for removing ozone from a gas or for purifying ozone. The liquid having a high ozone concentration can be used for ozonolysis of a substrate.
    Type: Application
    Filed: November 4, 2008
    Publication date: May 7, 2009
    Inventors: Bala Subramaniam, Daryle Busch, Andrew M. Danby, Thomas P. Binder
  • Patent number: 7427588
    Abstract: Novel compositions of matter and the process of preparing these surfactants having the structure: R1[—(O—(R2O)m—(R3O)n—(R4)]y where: R1=alkyl, alkenyl, amine, alkylamine, dialkylamine, trialkylamine, aromatic, polyaromatic, cycloalkane, cycloalkene, R2=C2H4 or C3H6 or C4H8, R3=C2H4 or C3H6 or C4H8, R4=linear or branched C7H14SO3X to C30H60 SO3X when y=1, R4=linear or branched C7H14SO3X to C30H60 SO3X or H when y>1 but at least one R4 must be linear or branched C7H14SO3X to C30H60 SO3X, m?1, n?0, n+m=1 to 30+, y?1, X=alkali metal or alkaline earth metal or ammonium or amine. These novel ether sulfonate surfactants have excellent surfactant properties making them suitable for a variety of applications as surfactants including agriculture, adhesives, coatings, deinking, detergents, emulsion polymerization, laundry, lubricants, metal working, mining, oilfield, personal care, pharmaceuticals, and soil remediation.
    Type: Grant
    Filed: January 12, 2007
    Date of Patent: September 23, 2008
    Inventors: Paul Daniel Berger, Christie Huimin Berger
  • Patent number: 7148375
    Abstract: A detergent composition having cold water solubility and exhibiting high calcium tolerance can be produced from biodegradable branched ether derivative compositions derived from a branched ether primary alcohol represented by the formula: wherein R1 represents hydrogen or a hydrocarbyl radical having from 1 to 3 carbon atoms, R2 represents a hydrocarbyl radical having from 1 to 7 carbon atoms, x is a number ranging from 0 to 16, preferably from 3 to 13, wherein the total number of carbon atoms in the alcohol ranges from 9 to 24.
    Type: Grant
    Filed: April 2, 2004
    Date of Patent: December 12, 2006
    Assignee: Shell Oil Company
    Inventors: Charles Lee Edwards, Kirk Herbert Raney, Paul Gregory Shpakoff
  • Patent number: 7122294
    Abstract: Photoacid generators (PAGs) comprising photoactive moieties and perfluorinated, multifunctional anionic moieties (or incipient anionic moieties) are disclosed which provide photoacids with high acid strength, low volatility and low diffusivity. The present invention further relates to photoacid generators as they are used in photoinitiated or acid-catalyzed processes for uses such as photoresists for microlithography and photopolymerization.
    Type: Grant
    Filed: May 22, 2003
    Date of Patent: October 17, 2006
    Assignee: 3M Innovative Properties Company
    Inventor: William M. Lamanna
  • Publication number: 20040127742
    Abstract: Provided herein is a class of compounds with surfactant properties known as alcohol ether sulfonates. These materials are produced according to the present invention by reaction of isethionic acid or its halo-derivative with an alcohol. An alcohol ether sulfonate according to the invention is useful as a component of a finished surfactant formulation useful for cleaning hard surfaces, laundry, and dishes, among other things.
    Type: Application
    Filed: October 21, 2003
    Publication date: July 1, 2004
    Applicant: Huntsman Petrochemical Corporation
    Inventors: Prakasa R. Anantaneni, Samir S. Ashrawi, David C. Lewis, George A. Smith
  • Patent number: 6459003
    Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: October 1, 2002
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu