Plural Ether Oxygens Or Thioether Sulfurs Attached Indirectly To The Phosphorus By Acyclic Nonionic Bonding Patents (Class 558/186)
  • Patent number: 6335314
    Abstract: This invention relates to an anionic alkoxylate surfactant (I), where R is di- or tri-unsaturated C4-22 straight or branched hydrocarbon chain, at least two double bonds of said unsaturated chain being conjugated and exhibiting opposite geometric isomerism; m is 0 or 1; Y is O or NR; each R40 is independently selected from hydrogen, C1-6 alkyl and phenyl; n is 1 to 50; and OX is an anionic group selected from the group consisting of acids or salts of sulphate, phosphate, sulphosuccinate, succinate, carboxymethyl, maleate, carboxyethyl, alkenylsuccinate, phthalate, sulphoethyl, 3-sulpho-2-hydroxypropyl, sulphopropyl, oxalate and citrate.
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: January 1, 2002
    Assignee: Orica Australia Pty. Ltd.
    Inventors: Elizabeth Ann Salter, Patrick William Houlihan, Michael Anthony Bajraszewski, Rodney Walter Parr, Keith Moody
  • Patent number: 6232486
    Abstract: This invention provides analogues of phosphatidylinositol-phosphates modified at one or more selected inositol-hydroxyls and optionally carrying reporter or anchoring groups attached in the lipid or the inositol residues, and, the synthetic intermediates and methods for the preparation of these analogues. The analogues are useful as research reagents in biomedical studies related to structure, function and therapeuticals, including reference materials for analyzing the metabolic products in safety and efficacy studies of 2- and/or 3-hydroxyl modified inositols and phosphatidylinositols as drug candidates.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: May 15, 2001
    Assignee: Nutrimed Biotech
    Inventor: Rajindra Aneja
  • Patent number: 6165501
    Abstract: Ether-linked phospholipids, derivatized at the polar head group with polyethylene glycol chains having molecular weights greater than 2,000 daltons, are disclosed. Lipid bilayers containing these phospholipids show high oxidative stability. Also disclosed is the use of PEG-derivatized ether-linked lipids in moisturizing and radiation-protective cosmetic compositions.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: December 26, 2000
    Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem
    Inventors: Oren Tirosh, Ron Kohen, Jehoshua Katzhendler, Yechezkel Barenholz
  • Patent number: 6121222
    Abstract: A novel class of anionic surfactants with improved surfact active properties is comprised of two hydrophilic and two hydrophobic groups represented by the formula: ##STR1## The surfactants exhibit unusually low critical micelle concentration (cmc) and pC-20 values in aqueous media.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: September 19, 2000
    Assignee: Rhodia Inc.
    Inventors: Ruoxin Li, David James Tracy, Jiang Yang, Manilal S. Dahanayake
  • Patent number: 5955453
    Abstract: Membrane-permeant phosphoinositides, including phosphatidylinositol phosphate esters, are described. A membrane-permeant phosphoinositide includes groups that neutralize the charges of the phosphate moieties of the phosphoinositide. A cell can be treated with the membrane-permeant phosphoinositide, which is then absorbed into the cell. The neutralizing groups can be removed intracellularly to afford the charged phosphoinositide.
    Type: Grant
    Filed: April 24, 1998
    Date of Patent: September 21, 1999
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Tao Jiang
  • Patent number: 5944650
    Abstract: A surfactant composition represented by Formulas (I), (II) or (III); or optionally mixtures thereof ##STR1## wherein R.sup.1 is a hydrophobic moiety of alkyl or aryl, and wherein alkyl contains from about 4 to about 60 carbon atoms and aryl contains from about 6 to about 60 carbon atoms; R.sup.2 is selected from the group consisting of alkyl and aryl, wherein alkyl contains from 1 to about 60 carbon atoms and aryl contains from about 6 to about 60; R.sup.3 is hydrogen or alkyl of from 1 to about 10 carbon atoms; A is a hydrophilic polymer chain; m is the number of repeating segments of the hydrophilic polymer chain and is a number of from about 2 to about 500.
    Type: Grant
    Filed: October 29, 1997
    Date of Patent: August 31, 1999
    Assignee: Xerox Corporation
    Inventors: Nan-Xing Hu, Paul F. Smith, Beng S. Ong
  • Patent number: 5922897
    Abstract: A process for the preparation of surfactants is described comprising reacting a phosphorus acid ester of the following Formula (IV) ##STR1## wherein R.sup.t is aryl, R.sup.2 is alkyl or aryl, with a hydrophilic polyoxyalkylene of the following Formulas (VIII), or (IX) ##STR2## wherein R.sup.3 is alkyl and A is a hydrophilic polyoxyalkylene chain, and which reaction results in an intermediate compound Formulas (XI), (XII), or (XIII); ##STR3## reacting the intermediate compound selected from the group consisting of Formulas (XI) through (XIII), with a hydroxylic compound R.sup.1 -OH (X) to yield surfactant precursors comprised of Formulas (V), (VI), and (VII), respectively: ##STR4## and, oxidizing said phosphorus ester-linked surfactant precursors selected from the group consisting of Formulas (V), (VI) and (VII), with an oxidizing agent to produce the surfactants.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: July 13, 1999
    Assignee: Xerox Corporation
    Inventors: Nan-Xing Hu, H. Bruce Goodbrand
  • Patent number: 5846516
    Abstract: Perfluoroalkylated amphiphilic phosphorus compounds, corresponding to the formulae: ##STR1## wherein V is O or S;R.sup.1, R.sup.2 and R.sup.3 are H or substituted or unsubstituted perfluoroalkylated or hydrocarbon radicals;provided thatR.sup.1, R.sup.2 or R.sup.3 is a perfluoroalkylated radical; and Y and Z are radicals which can bear a part derived from a sugar, a polyol, or a hydrophilic polymer such as polyethyleneglycol, a perfluoroalkylated part or a part derived from a pharmaceutically active molecule, and method for their preparation and use. These compounds can be included in preparations, emulsions, dispersions, gels, microemulsions, notably for biomedical uses.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: December 8, 1998
    Assignee: Alliance Pharmaceutial Corp.
    Inventors: Jean G. Riess, Jacques Greiner, Alain Milius, Pierre Vierling, Frederic Guillod, Sylvie Gaentzler
  • Patent number: 5817856
    Abstract: Novel ether-linked phospholipids derivatized with polyethylene glycol at the polar head group are disclosed. Lipid bilayers containing these phospholipids show high oxidative stability. Also disclosed is the use of PEG-derivatized ether-linked lipids in moisturizing and radiation-protective cosmetic compositions.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: October 6, 1998
    Assignee: Yissum Research Development Company of the Hebrew University of Jerusalem
    Inventors: Oren Tirosh, Ron Kohen, Joshua Katzhendler, Yechezkel Barenholz
  • Patent number: 5807814
    Abstract: Oil soluble compounds having the formula: ##STR1## wherein R and R.sup.1 are independently cyano, alkoxycarbonyl, aryloxycarbonyl, alkenyloxycarbonyl, alkylcarbonyl, arylcarbonyl, alkenylcarbonyl, alkylsulfonyl, arylsulfonyl, alkenylsulfonyl, substituted aminocarbonyl, alkylphosphoryl, arylphosphoryl, alkenylphosphoryl, aryl, or heterocyclics, or together form a carbocycle or heterocycle, and R.sup.2 and R.sup.3 are independently alkyl, alkenyl, hydroxyalkyl, sulfurized alkyl, alkoxycarbonylalkyl, arylalkyl, or borated hydroxyalkyl, with the proviso that R, R.sup.1, R.sup.2 and R.sup.3 together contain sufficient carbon atoms to render the compound oil soluble in an oil of lubricating viscosity. The compound are useful as wear protectants or extreme pressure agents to enhance wear protection or extreme pressure properties in lubricating oils and greases.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: September 15, 1998
    Assignee: Chevron Chemical Company
    Inventor: Andrew W. Ho
  • Patent number: 5726165
    Abstract: A compound of formula (I): ##STR1## or a pharmaceutically acceptable salt, or solvate thereof, wherein,R.sup.o represents an aryl group, optionally substituted;X represents O or S;R.sup.1 and R.sup.1a each independently represents hydrogen or an alkyl group;R.sup.2 represents OCH.sub.2 CO.sub.2 H, or an ester or amide thereof, or R.sup.2 represents a moiety of formula (b): ##STR2## wherein R.sup.4 represent hydrogen, alkyl, hydroxyalkyl, arylalkyl, aralkyloxyalkyl or cycloalkyl and R.sup.5 represent hydroxy, alkoxy, arylalkyloxy, hydroxyalkyloxy, alkoxyalkyloxy, arylalkoxyalkyloxy, cycloalkyloxy, hydrogen, alkyl, substituted alkyl, cycloalkyl, aryl, arylalkyl, arylalkyloxyalkyl or R.sup.5 together with OR.sup.4 represents O(CH.sub.2).sub.n O wherein n is 2, 3 or 4; andR.sup.3 represents hydrogen, halogen, alkyl or alkoxy or R.sup.3 together with R.sup.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: March 10, 1998
    Assignee: SmithKline Beecham p.l.c.
    Inventors: Lee James Beeley, Mervyn Thompson, David Kenneth Dean, Nikesh Rasiklal Kotecha, John Michael Berge, Robert William Ward
  • Patent number: 5693807
    Abstract: The invention relates to substituted hydroquinone derivatives of the general formula I ##STR1## wherein R.sub.4 is lower alkyl and either R.sub.1 is hydroxy, halogen, a group of the formula --P(=O)(R.sub.5)R.sub.6 (Ia), a group of the formula --P.sup.+ (R.sub.7)(R.sub.8)R.sub.9 X.sup.- (Ib) or a group of the formula --Si(R.sub.7)(R.sub.8)R.sub.9 (Ic), M is methylene, R.sub.2 is hydrogen or a group of the formula ##STR2## and R.sub.3 is hydrogen or halogen, or .sub.1 is hydroxy or lower alkoxy, M is carbonyl, R.sub.2 is hydrogen and R.sub.3 is halogen, each of R.sub.5 and R.sub.6, independently of the other, is lower alkyl, lower alkoxy Or N,N-di-lower alkylamino, or is benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, to a process for the preparation of those compounds and to the use of those compounds, and to a process in which those compounds are used.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Gottfried Sedelmeier, Gerhard Fischer
  • Patent number: 5679459
    Abstract: Perfluoroalkylated amphiphilic phosphorus compounds, corresponding to the formulae: ##STR1## wherein V is O or S;R.sup.1, R.sup.2 and R.sup.3 are H or substituted or unsubstituted perfluoroalkylated or hydrocarbon radicals;provided thatR.sup.1, R.sup.2 or R.sup.3 is a perfluoroalkylated radical; and Y and Z are radicals which can bear a part derived from a sugar, a polyol, or a hydrophilic polymer such as polyethyleneglycol, a perfluoroalkylated part or a part derived from a pharmaceutically active molecule, and method for their preparation and use. These compounds can be included in preparations, emulsions, dispersions, gels, microemulsions, notably for biomedical uses.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 21, 1997
    Assignee: Alliance Pharmaceutical Corp.
    Inventors: Jean G. Riess, Jacques Greiner, Alain Milius, Pierre Vierling, Frederic Guillod, Sylvie Gaentzler
  • Patent number: 5512534
    Abstract: The present invention relates to compounds of the formula I ##STR1## in which R.sup.1 is hydrogen,a substituted or unsubstituted aliphatic radicalhaving up to 30 carbon atoms,a substituted or unsubstituted alicyclic radicalhaving up to 30 carbon atoms,a substituted or unsubstituted aromatic radicalhaving up to 24 carbon atoms ora substituted or unsubstituted heteroaromaticradical having up to 20 carbon atoms,R.sup.2 is an amino acid,x'=0-80,y'=0-50,x"=0-80 andy"=0-50,with at least one of the variables x', y', x" and y" being greater than 0. The compounds of the formula I are prepared by reacting the corresponding dihydrogen phosphate with the respective amino acid or salt thereof. The compounds according to the invention can be employed, for example, as surfactants for emulsifying organic solvents in water.
    Type: Grant
    Filed: October 4, 1993
    Date of Patent: April 30, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Frisch, Thomas Maier
  • Patent number: 5478960
    Abstract: Heterosubstituted acetals of the formula ##STR1## can be obtained by reacting vinyl compounds of the formulaCH.sub.2 .dbd.CH-A.sup.1 (II)with alkyl nitrites of the formulaR.sup.1 --ONO (III.)The reaction is performed in the presence of palladium in metallic or bonded form and in alcohols or ethers as reaction medium at from 0.degree. to 120.degree. C.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: December 26, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Landscheidt, Alexander Klausener
  • Patent number: 5464895
    Abstract: A dispersing agent for use in a thermosetting composition, a thermosetting composition containing said dispersing agent, and application thereof to thermosetting composition having no yield point. The dispersing agent acting on mineral fillers and used in filled acrylic or polyester resin-based thermosetting compositions belongs to the family of organophosphates corresponding to the general formula: ##STR1## where: A is a branched or unbranched polyaryl group,x and y are whole numbers between 0 and 100 such that x+y is a whole number greater than 40 but not greater than 100, ##STR2## B and E are independently a branched or unbranched polyaryl group, or an alkyl, aryl, arylalkyl, alkylaryl, alkanoyl, or amine radical, and in B and E, and R.sub.1 and R.sub.2 may be identical or different, x1, y1, x2 and y2 are whole numbers, and the sums x1+y1 and x2+y2 are not greater than 100.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: November 7, 1995
    Assignee: Coatex, S.A.
    Inventors: Pierre Blanchard, Jean-Bernard Egraz, Georges Ravet
  • Patent number: 5463101
    Abstract: This invention relates to first stage phosphation processes which utilize a unique phosphation reagent that esterifies ethoxylated alcohols under mild reaction conditions, thus realizing reduced initial 1,4-dioxane production followed by formation of a dioxane-water azeotrope and the vacuum stripping at above about 100 torr of the azeotrope. This easily achieves product 1,4-dioxane levels below about 15 ppm based on the total ester weight.
    Type: Grant
    Filed: December 1, 1994
    Date of Patent: October 31, 1995
    Assignee: Rhone-Poulenc Inc.
    Inventor: Robert L. Reierson
  • Patent number: 5414103
    Abstract: A polyalkylene glycol ether phosphate ester, or salt thereof, having the formula:R.sub.w --P(O)(OH).sub.3-w (I)wherein w is an integer from 1 to 3, andR is an oil-soluble polyether moiety having the formula:R.sup.1 X[(C.sub.x H.sub.2x O).sub.n (C.sub.y H.sub.2y O).sub.p ].sub.m(II)wherein R.sup.1 is either an alkyl or an alkyl phenyl group having from 7 to 30 carbon atoms,X is either O, S, or Nx is an integer from 2 to 4,y is an integer from 6 to 30,m is 1 when X is O or S and m is 2 when X is N,n and p are such that the polyether moiety contains between 1 and 35% by weight of (C.sub.y H.sub.2y O) units and between 35 and 80% by weight of (C.sub.x H.sub.2x O) units, and the molecular weight of the polyalkylene glycol moiety is between 500 and 5000 is disclosed,The phosphate ester can be prepared by reacting a polyether with a phosphating agent, e.g. phosphorus pentoxide and water. Lubricating oil compositions comprising the phosphate ester or salt thereof are also disclosed.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: May 9, 1995
    Assignee: Oceanfloor Limited
    Inventors: Robert B. Cracknell, Anthony J. Moore
  • Patent number: 5412139
    Abstract: A dispersing agent for use in a thermosetting composition, a thermosetting composition containing said dispersing agent, and application thereof to thermosetting composition having no yield point. The dispersing agent acting on mineral fillers and used in filled acrylic or polyester resin-based thermosetting compositions belongs to the family of organophosphates corresponding to the general formula: ##STR1## where: A is a branched or unbranched polyaryl group,x and y are whole numbers between 0 and 100 such that x+y is a whole number greater than 40 but not greater than 100, ##STR2## B and E are independently a branched or unbranched polyaryl group, or an alkyl, aryl, arylalkyl, alkylaryl, alkanoyl, or amine radical, and in B and E, and R.sub.1 and R.sub.2 may be identical or different, x1, y1, x2 and y2 are whole numbers, and the sums x1+y1 and x2+y2 are not greater than 100.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: May 2, 1995
    Assignee: Coatex, S.A.
    Inventors: Pierre Blanchard, Jean-Bernard Egraz, Georges Ravet
  • Patent number: 5405544
    Abstract: Beta-hydroxyalkyl-bis(alkylthiomethylphenyl) dithiophosphate esters represented by the formulas ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each H, a (C.sub.1 -C.sub.40) alkyl group, --CH.sub.2 SR, --C.sub.6 H.sub.5 or --C.sub.6 H.sub.4 --R.sub.5 providing at least one of R.sub.1, R.sub.2 and R.sub.3 is --CH.sub.2 SR; R.sub.4 is H or a (C.sub.1 -C.sub.40) alkyl group; R is H or a (C.sub.1 -C.sub.40) alkyl group, --C.sub.6 H.sub.5 or --C.sub.6 H.sub.4 --R.sub.5 ; and R.sub.5 is a (C.sub.1 -C.sub.40) alkyl group.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: April 11, 1995
    Assignee: Texaco Inc.
    Inventors: Carl K. Esche, Jr., Julian H. Dancy, Doris Love
  • Patent number: 5395657
    Abstract: Oil- and water-repellency is imparted to the surface of a porous ceramic material, in particular of "cotto", by applying a phosphoric monoester having formula: ##STR1## where: L is a divalent organic group; m=1; Y is --F or --CF.sub.3 ;Z.sup.+ is a cation; R.sub.f is a polyperfluoroalkylene oxide chain.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: March 7, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Ezio Strepparola, Viviana Boselli, Mauro Scapin
  • Patent number: 5372743
    Abstract: The degreasing composition comprises a surfactant composition comprising a compound (a) represented by the general formula (1):R.sup.1 O(AO).sub.n H (1)wherein R.sup.1 is a substituted or unsubstituted hydrocarbon group having 6 or more carbon atoms; A is at least one group selected from the group consisting of an ethylene group, a propylene group, a butylene group and a styrene group, provided that an ethylene group in A is 5 mol or more per 1 mol of R.sup.1, and that the ethylene group is 50 mol % or more per 100 mol % of said A; and n is an integer of 5-50;a compound (b1) represented by the general formula (2): ##STR1## wherein R.sup.2 is a substituted or unsubstituted hydrocarbon group having 6 or more carbon atoms, E is an ethylene group, and n is an integer of 1-20; and a compound (b2) represented by the general formula (3): ##STR2## wherein R.sup.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: December 13, 1994
    Assignees: Nippon Paint Co., Ltd., Asahi Denka Kogyo K.K.
    Inventors: Satoshi Miyamoto, Isao Kawasaki, Kaoru Komiya
  • Patent number: 5344930
    Abstract: Compounds of the general formula: ##STR1## are useful as surfactants in the preparation of fluorocarbon emulsions, which can be used as oxygen-carrying blood substitutes, and for many other therapeutic and diagnostic applications. They are further useful in liposomal formulations which are themselves therapeutic agents or provide a vehicle for such agents.
    Type: Grant
    Filed: November 8, 1993
    Date of Patent: September 6, 1994
    Assignee: Alliance Pharmaceutical Corp.
    Inventors: Jean G. Riess, Francois Jeanneaux, Marie-Pierre Krafft, Catherine Santaella, Pierre Vierling
  • Patent number: 5322871
    Abstract: Compounds of the formula I ##STR1## in which x is 1, 2 or 3, and, if x=1, R.sup.1 is C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.18 alkyl substituted by halogen, --COOR.sup.2, --CN, --NR.sup.3 R.sup.4 or by --CONR.sup.3 R.sup.4, C.sub.2 -C.sub.18 alkyl which is interrupted by --NR.sup.5 --, --O-- or --S--, C.sub.3 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl-C.sub.1 -C.sub.4 alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen, phenyl-C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, or R.sub.1 is naphthyl, a radical of the formula ##STR2## R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl or phenyl-C.sub.1 -C.sub.4 alkyl, R.sup.6 is hydrogen, methyl, allyl or benzyl, R.sup.7 is hydrogen or --OR.sup.9, R.sup.8 is hydrogen or methyl, R.sup.9 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.10 and R.sup.11, independently of one another, are hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: April 20, 1993
    Date of Patent: June 21, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rita Pitteloud, Peter Hofmann, Rudolf Maul, Volker Schenk, Eduard Troxler, Horst Zinke
  • Patent number: 5312953
    Abstract: Polyether bis-phosphonic acid compounds are disclosed which have the formula (HO).sub.2 OP--R--(OR').sub.n --OR--PO(OH).sub.2 where R is selected from the group consisting of methylene and ethylene, R' is selected from the group consisting of ethylene and ethylene substituted with one or more methyl groups, and n is an integer from 1 to 4, water soluble salts thereof, and esters thereof with alkyl groups having from 1 to 6 carbon atoms. Also disclosed is a novel preparation of these compounds by reacting hydroxyalkylphosphonic acid dialkyl ester compounds with 2-benzyloxyalkyl organic sulfonates; reacting the intermediate formed therefrom with hydrogen or a hydrogen source; reacting the intermediate formed therefrom with a hydrogen ion acceptor and certain sulfonyl chlorides; and reacting the intermediate formed therefrom with hydroxyalkylphosphonic acid dialkyl ester compounds to form a polyether bis-phosphonic acid compound which may be hydrolyzed to form the polyether bis-phosphonic acid.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: May 17, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Charles G. Carter, Ranjit Kumar
  • Patent number: 5306436
    Abstract: Useful as additive for lubricating oils are novel phosphosulphur compounds in accordance with the general formula (I):(((R.sup.1 --S.sub.x --O.sub.y --A--).sub.r B.sub.v).sub.p P(X)--Y.sub.t --).sub.q Z.sub.min which e.g. R.sup.1 represents an alkyl or alkenyl group, A represents the group --(CH.sub.2).sub.n --O--, B represents the group --P(S)--S--CH.sub.2 --(CH.sub.3)--O--, X represents an oxygen atom or a sulphur atom, Y represents an oxygen atom, a sulphur atom or an oxygen or sulphur-containing hydrocarbon chain, Z represents a hydrogen, chlorine or sulphur atom, a polysulphide chain, a metal or an alkyl or alkenyl group, x=1,2 or 3, y=0, 1 or 2, v is 0 or 1, r is 1 (if v=0) or r=2 (if v=1), p=2 or 3, t=0 or 1, m=0,1 or 2, q=the valency of Z if Z is a metal or q=1 or 2 and n is an integer from 1 to 30.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: April 26, 1994
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Ourida Aberkane, Jean-Luc Mieloszynski, Daniel Paquer, Guy Parc
  • Patent number: 5266722
    Abstract: Polyether bis-phosphonic acid compounds are disclosed which have the formula (HO).sub.2 OP--R--(OR').sub.n --OR--PO(OH).sub.2 where R is selected from the group consisting of methylene and ethylene, R' is selected from the group consisting of ethylene and ethylene substituted with one or more methyl groups, and n is an integer from 1 to 4, water soluble salts thereof, and esters thereof with alkyl groups having from 1 to 6 carbon atoms.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: November 30, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Charles G. Carter, Ranjit Kumar
  • Patent number: 5219845
    Abstract: The invention pertains to the synthesis and use as therapeutic agents of a group of substances with a glycerol backbone or aliphatic chain structure linked to a phosphorus atom and a polar head group. Depending on the polar head group, the substance has anti-cancer, anti-inflammatory, anti-allergy or anti-cardiovascular disease properties. Compounds of the formula: ##STR1## wherein n is 0 to 14 and R.sub.1 is an alkyl group of C.sub.12 -C.sub.20, R.sub.2 is a methyl group, and wherein R.sub.3 is an inositol analog head group, a (CH.sub.2).sub.m N.sup.+ (CH.sub.3).sub.3 group with m=2 to 10, a serine head group, or an ethanolamine head group, or of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as described above, n=0 or 1, and R.sub.3 is (CH.sub.2).sub.m N.sup.+ (CH.sub.3).sub.3 (m=2-10) are claimed.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: June 15, 1993
    Assignee: The University of British Columbia
    Inventors: Hassan Salari, Robert Bittman
  • Patent number: 5202111
    Abstract: A composition and method for controlling tartar formation in the mouth is reported based upon phosphorylated polyhydroxy substances. These substances are formed by phosphorylation of a polyhydroxy starting compound of molecular weight no higher than 5000, have a molar substitution of at least 2 based on molecular weight of an average repeat unit in the starting polyhydroxy compound and possess phosphate ester linkages satisfying at least one criteria selected from:(a) at least one multi-substituted phosphate ester linked through an oxygen atom to a single carbon of the polyhydroxy compound; and(b) at least two monophosphate groups separated by no more than three carbon atoms.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: April 13, 1993
    Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.
    Inventors: Suree M. Spaltro, Michael P. Aronson
  • Patent number: 5151414
    Abstract: Compounds of formula ##STR1## (wherein R, R.sub.1, R.sub.2, R.sub.3, n, m and p have the meanings reported in the specification), their preparation and the compositions for pharmaceutical use containing them as active ingredient are described.The compounds of formula I have dopaminergic vasodilator activity and they may be used in pharmaceutical field.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: September 29, 1992
    Assignee: SIMES Societa Italiana Medicinali e Sintetici S.p.A.
    Inventors: Cesare Casagrande, Gabriele Norcini, Francesco Santangelo, Claudio Semeraro
  • Patent number: 5132446
    Abstract: A fluorine-containing phosphate ester of the formula: ##STR1## wherein R.sub.f is a group containing a perfluoroalkyl polyether group of the formula:F(CF.sub.2 CF.sub.2 CF.sub.2 O).sub.m CF.sub.2 CF.sub.2 --wherein m is 2 to 200, and n is an integer of 1 to 3 is used as a rust preventive which can be homogeneously mixed with a fluorine-containing grease.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: July 21, 1992
    Assignee: Daikin Industries, Ltd.
    Inventors: Takashi Tohzuka, Yoshiaki Kataoka, Sueyoshi Ishikawa
  • Patent number: 5126474
    Abstract: Polyadducts of an alkylene oxide and styrene oxide with an aryl alcohol, especially polyadducts of formulae ##STR1## wherein the ring A is an unsubstituted phenyl radical or a phenyl radical which is substituted by halogen, methyl or C.sub.1 -C.sub.3 alkoxy,Q.sub.1 is alkylene of 1 to 4 carbon atoms, preferably methylene, in the pairs of substituents (Y.sub.1 and Y.sub.2) and (Y.sub.3 and Y.sub.4) one Y is phenyl and the other Y is hydrogen,"alkylene" denotes an alkylene radical of 2 or 3 carbon atoms, andm is an integer from 1 to 80.These polyadducts are a novel class of nonionic or anionic surfactants which are used as textile auxiliaries.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: June 30, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Rosemarie Topfl
  • Patent number: 5091550
    Abstract: 5,5-Bis(perfluoroalkylheteromethyl)-2-hydroxy-2-oxo-1,3,2-dioxaphosphorinan es, derived acyclic phosphorus and phosphoric acids obtained by ring-opening, and salts or esters thereof are prepared from heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formula: HO[CH.sub.2 C(CH.sub.2 --X--E.sub.n --R.sub.f).sub.2 CH.sub.2 O]H by cyclization with appropriate phosphorus containing esters or acids, or hydrolysis. These compositions provide improved thermal stability, and useful low surface energy oil and water repellent coatings for textiles, glass, paper, leather and other materials.Another aspect of this invention relates to the use of the phosphite group containing products as polymer stabilizers.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: February 25, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark
  • Patent number: 5041597
    Abstract: The invention concerns a process for the manufacture of surface-active sulfophosphoric-acid-(partial)-alkyl-esters and their alkali-, alkaline earth-, ammonium- and amine salts by the sulfonation of phosphoric acid esters and subsequent hydrolysis of the sultone intermediate stages formed.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: August 20, 1991
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Bernd Fabry, Hans-Herbert Friese, Friedrich Pieper, Guenter Uphues
  • Patent number: 5015635
    Abstract: Pesticidal S-(halogenoalkyl)-dithiophosphoric (phosphonic) acid esters of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkoxy, alkenyloxy and alkinyloxy,R.sup.2 represents an optionally substituted radical from the group consisting of alkyl, cycloalkyl, alkenyl, alkinyl and aryl,X and Y are identical or different and independently of one another represent hydrogen, halogen or alkyl, andZ represents hydrogen, halogen or alkyl.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: May 14, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Sommer, Jurgen Hartwig, Hans-Detlef Matthaei
  • Patent number: 4994581
    Abstract: A novel phosphoric ester of the formula (I) ##STR1## wherein, Z represents the following radicals ##STR2## useful as modifiers for amino acids, peptides and proteins which are easily decomposable in living bodies.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: February 19, 1991
    Assignee: Kao Corporation
    Inventors: Motoru Takeda, Mitsuharu Masuda, Takashi Imamura, Tomihiro Kurosaki
  • Patent number: 4981989
    Abstract: Antihypertensive phosphate derivatives having the following formula are described: ##STR1## wherein X is selected from one or more of: (a) C.sub.1 -C.sub.24 branched or straight chain alkyl; (b) C.sub.1 -C.sub.24 branched or straight chain alkoxy; (c) ##STR2## wherein n and m are integers from 0 to 25 and the sum of n and m is less than or equal to 25; phenyl; substituted phenyl wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, C.sub.1 -C.sub.20 branched or straight chain alkoxy, halogen, trifluoromethyl, phenyl, and substituted phenyl, phenoxy; and substituted phenoxy, wherein the substituents are selected from the group consisting of C.sub.1 -C.sub.20 branched or straight chain alkyl, halogen, trifluoromethyl, phenyl and substituted phenyl; Q is selected from the group consisting of: ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 branched or straight chain alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: January 1, 1991
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
  • Patent number: 4939283
    Abstract: Novel surfactants of the formula: ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkylaryl or aralkylaryl of 8-30 carbon atoms,A is alkylene of 2-4 carbon atoms,x is 0, or 1-100 andy is 1-200.Sulfates, phosphates and sulfosuccinates thereof are also useful as anionic surfactants.
    Type: Grant
    Filed: December 15, 1988
    Date of Patent: July 3, 1990
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Kinya Yokota, Akinobu Ichihara
  • Patent number: 4933478
    Abstract: A process for the production of aliphatylphosphinic acid derivatives, especially of alkyl dialkoxyalkylphosphinates having the formula I ##STR1## in which R is C.sub.1 -C.sub.4 -alkyl and R' is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting, in the presence of an acidic catalyst, aqueous phosphonic acid with the corresponding trialkyl orthoester having the formula II:(RO).sub.3 CR' IIin whicih R and R' have their previous significances, the amount of the orthoester of formula II used being equal to, or in excess of the stoichiometric amount of both water and phosphinic acid present in the aqueous phosphinic acid reactant.
    Type: Grant
    Filed: September 1, 1988
    Date of Patent: June 12, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter S. Wardleworth, Eric K. Baylis
  • Patent number: 4918211
    Abstract: Novel surfactants of the formula: ##STR1## wherein R.sub.1 is alkyl, alkenyl or aralkyl of 4-18 carbon atoms, R.sub.2 is hydrogen or same as R.sub.1, R.sub.3 is hydrogen or methyl, A is alkylene of 2-4 carbon atoms, and n is 1-200. Sulfates, phosphates and sulfosuccinates thereof are also useful as anionic surfactants.
    Type: Grant
    Filed: November 10, 1987
    Date of Patent: April 17, 1990
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Kinya Yokota, Akinobu Ichihara, Hitoshi Shinike
  • Patent number: 4912245
    Abstract: Surfactant compositions in an acidic or neutralized form containing a mixture of at least one polyoxyalkylenated phosphoric acid monoester and at least one polyoxyalkylenated diester and a nonionic polyoxyalkylenated compound wherein the phosphoric acid diester:phosphoric acid monoester molar ratio before neutralization, if carried out, is at least equal to 0.9:1 and the phosphoric acid monoester and phosphoric acid diester content is at least 1 mol %, preferably at least 50 mol % of said composition. The surfactant compositions are prepared by phosphatization of a nonionic polyoxyalkylenated compound at a temperature of from about 35.degree. to about 45.degree. C. followed by maturing at from about 40.degree. to about 60.degree. C., in a stirred turbulent state. The compositions are useful in the formulation of active substances in the form of microgranules and flowables.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: March 27, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Yvette Girardeau, Christian Segaud
  • Patent number: 4889945
    Abstract: The invention relates to phosphoric acid partial esters derived from a block ethoxylated and propoxylated C.sub.9-16 aliphatic alcohol. These phosphoric acid partial esters are useful as wetting agents, especially in the pre-treatment of cellulosic textile materials.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: December 26, 1989
    Assignee: Sandoz Ltd.
    Inventor: Achim Wiedemann
  • Patent number: 4851161
    Abstract: .beta.-substituted polyfluoropropionate salts, derivatives and copolymers and processes for the preparation thereof.
    Type: Grant
    Filed: December 16, 1986
    Date of Patent: July 25, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4830764
    Abstract: The invention relates to phosphoric acid partial esters derived from a block ethoxylated and propoxylated C.sub.9-16 aliphatic alcohol. These phosphoric acid partial esters are useful as wetting agents, especially in the pre-treatment of cellulosic textile materials.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: May 16, 1989
    Assignee: Sandoz Ltd.
    Inventor: Achim Wiedemann
  • Patent number: 4831176
    Abstract: Novel ether phosphonate surfactants having a branched hydrophobic tail are used in a process for enhanced oil recovery from a subterranean oil reservoir. They combine a high oil-mobilizing capacity with a good tolerance against divalent ions. The ether phosphonate surfactants are summarized by the formula ##STR1## where R.sub.1 and R.sub.2, being the same or different, are hydrocarbons containing 3-18 carbon atoms each and optionally containing functional groups such as ether and hydroxyl; X is an alkyleneoxy group derived from an alkylene oxide having 2-3 carbon atoms; Y is an alkylene group having 1-4 carbon atoms; R.sub.3 is an alkyl group having 1-4 carbon atoms; M.sup.+ is a monovalent cation; n.sub.1 and n.sub.2, being the same or different, are a number from 0 to 4; m.sub.1 and m.sub.2, being the same or different, are 0 or 1, both m.sub.1 and m.sub.2 not being 0 at the same time and m.sub.1 being 1 when n.sub.1 is a number from 1 to 4 and m.sub.2 always being 1 when n.sub.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: May 16, 1989
    Assignee: Berol Kemi AB
    Inventors: Krister Holmberg, Eva sterberg
  • Patent number: 4814514
    Abstract: Novel surfactants of the formula: ##STR1## wherein R.sub.1 is alkyl, alkenyl, alkylaryl or aralkylaryl of 8-30 carbon atoms,A is alkylene of 2-4 carbon atoms,x is 0, or 1-100 andy is 1-200. Sulfates, phosphates and sulfosuccinates thereof are also useful as anionic surfactants.
    Type: Grant
    Filed: May 6, 1987
    Date of Patent: March 21, 1989
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Kinya Yokota, Akinobu Ichihara
  • Patent number: 4798872
    Abstract: A process for preparing hydroxy phosphonic acid ester polyols by reacting an alkenyl phosphonic acid with an alkylene oxide and the reaction of the resulting hydroxy phosphonic acid ester polyols with polyisocyanates to form polyurethanes is described.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: January 17, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Biau-Hung Chang
  • Patent number: 4781722
    Abstract: Novel alkanephosphonic monoester salts, preparation thereof and use thereof as spin finishes for textile fibersAlkylphosphonic monoester salts of the formula ##STR1## where R, if p=1, is alkyl, and, if p=4, a carbon atom, R.sup.1 denotes C.sub.1 -C.sub.4 -alkyl, A denotes C.sub.2 H.sub.4 and/or C.sub.3 H.sub.7, m denotes a number from 15 to 35, R.sup.2 denotes C.sub.6 -C.sub.24 -alkyl, n denotes a number from 0 to 15, and p denotes 1 or 4 . These compounds are suitable for use as spin finishes for textile fibers and are distinguished by very good thermostability.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: November 1, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jerg Kleiner, Rolf Kleber, Lothar Jaeckel
  • Patent number: 4754048
    Abstract: Novel (halo)(hydroxy)-substituted phosphorus-containing acid derivatives are disclosed. Preferred compounds are 2-halo-3-hydroxypropyl ester derivatives of phosphorus and phosphoric acid formed by reaction of at least some amount of tertiary butyl glycidyl ether with a halogenated derivative of a phosphorus-containing acid followed by acid dealkylation of the product. The polyol products are useful in the production of polyurethane articles such as foams having increased resistance to the effects of fire. The derivatives can be additives or reactants in the polyurethane, depending on the presence or absence of terminal hydroxyl groups within the given ester moieties.
    Type: Grant
    Filed: November 7, 1986
    Date of Patent: June 28, 1988
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Sally P. Ginter
  • Patent number: 4727177
    Abstract: Antistatic agents for synthetic fibers comprising a specific type of quaternary ammonium alkyl phosphate as principal constituent and 1 weight percent or less of by-product alkali metal halides have improved antistatic characteristics both in high and low humidity conditions and reduce the amount of deposits that fall off, yellowing by a heat treatment and generation of rust. Methods of producing such antistatic agents are also disclosed.
    Type: Grant
    Filed: March 6, 1986
    Date of Patent: February 23, 1988
    Assignee: Takemoto Yushi Kabushiki Kaisha
    Inventors: Masatsugu Saiki, Yoshio Imai, Makoto Takagi