Plural Ether Oxygens Or Thioether Sulfurs Attached Indirectly To The Phosphorus By Acyclic Nonionic Bonding Patents (Class 558/186)
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Patent number: 6335314Abstract: 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: GrantFiled: March 21, 2000Date of Patent: January 1, 2002Assignee: Orica Australia Pty. Ltd.Inventors: Elizabeth Ann Salter, Patrick William Houlihan, Michael Anthony Bajraszewski, Rodney Walter Parr, Keith Moody
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Patent number: 6232486Abstract: 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: GrantFiled: June 10, 1997Date of Patent: May 15, 2001Assignee: Nutrimed BiotechInventor: Rajindra Aneja
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Patent number: 6165501Abstract: 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: GrantFiled: October 6, 1998Date of Patent: December 26, 2000Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Oren Tirosh, Ron Kohen, Jehoshua Katzhendler, Yechezkel Barenholz
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Patent number: 6121222Abstract: 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: GrantFiled: December 27, 1996Date of Patent: September 19, 2000Assignee: Rhodia Inc.Inventors: Ruoxin Li, David James Tracy, Jiang Yang, Manilal S. Dahanayake
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Patent number: 5955453Abstract: 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: GrantFiled: April 24, 1998Date of Patent: September 21, 1999Assignee: The Regents of the University of CaliforniaInventors: Roger Y. Tsien, Tao Jiang
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Patent number: 5944650Abstract: 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: GrantFiled: October 29, 1997Date of Patent: August 31, 1999Assignee: Xerox CorporationInventors: Nan-Xing Hu, Paul F. Smith, Beng S. Ong
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Patent number: 5922897Abstract: 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: GrantFiled: May 29, 1998Date of Patent: July 13, 1999Assignee: Xerox CorporationInventors: Nan-Xing Hu, H. Bruce Goodbrand
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Patent number: 5846516Abstract: 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: GrantFiled: June 3, 1992Date of Patent: December 8, 1998Assignee: Alliance Pharmaceutial Corp.Inventors: Jean G. Riess, Jacques Greiner, Alain Milius, Pierre Vierling, Frederic Guillod, Sylvie Gaentzler
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Patent number: 5817856Abstract: 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: GrantFiled: December 11, 1995Date of Patent: October 6, 1998Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Oren Tirosh, Ron Kohen, Joshua Katzhendler, Yechezkel Barenholz
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Patent number: 5807814Abstract: 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: GrantFiled: July 5, 1996Date of Patent: September 15, 1998Assignee: Chevron Chemical CompanyInventor: Andrew W. Ho
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Patent number: 5726165Abstract: 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: GrantFiled: June 5, 1995Date of Patent: March 10, 1998Assignee: SmithKline Beecham p.l.c.Inventors: Lee James Beeley, Mervyn Thompson, David Kenneth Dean, Nikesh Rasiklal Kotecha, John Michael Berge, Robert William Ward
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Patent number: 5693807Abstract: 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: GrantFiled: June 5, 1995Date of Patent: December 2, 1997Assignee: Ciba-Geigy CorporationInventors: Gottfried Sedelmeier, Gerhard Fischer
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Patent number: 5679459Abstract: 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: GrantFiled: June 6, 1995Date of Patent: October 21, 1997Assignee: Alliance Pharmaceutical Corp.Inventors: Jean G. Riess, Jacques Greiner, Alain Milius, Pierre Vierling, Frederic Guillod, Sylvie Gaentzler
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Patent number: 5512534Abstract: 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: GrantFiled: October 4, 1993Date of Patent: April 30, 1996Assignee: Hoechst AktiengesellschaftInventors: Gerhard Frisch, Thomas Maier
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Patent number: 5478960Abstract: 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: GrantFiled: March 22, 1995Date of Patent: December 26, 1995Assignee: Bayer AktiengesellschaftInventors: Heinz Landscheidt, Alexander Klausener
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Patent number: 5464895Abstract: 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: GrantFiled: September 29, 1994Date of Patent: November 7, 1995Assignee: Coatex, S.A.Inventors: Pierre Blanchard, Jean-Bernard Egraz, Georges Ravet
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Patent number: 5463101Abstract: 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: GrantFiled: December 1, 1994Date of Patent: October 31, 1995Assignee: Rhone-Poulenc Inc.Inventor: Robert L. Reierson
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Patent number: 5414103Abstract: 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: GrantFiled: December 28, 1992Date of Patent: May 9, 1995Assignee: Oceanfloor LimitedInventors: Robert B. Cracknell, Anthony J. Moore
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Patent number: 5412139Abstract: 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: GrantFiled: January 14, 1992Date of Patent: May 2, 1995Assignee: Coatex, S.A.Inventors: Pierre Blanchard, Jean-Bernard Egraz, Georges Ravet
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Patent number: 5405544Abstract: 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: GrantFiled: August 2, 1993Date of Patent: April 11, 1995Assignee: Texaco Inc.Inventors: Carl K. Esche, Jr., Julian H. Dancy, Doris Love
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Patent number: 5395657Abstract: 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: GrantFiled: December 16, 1993Date of Patent: March 7, 1995Assignee: Ausimont S.p.A.Inventors: Ezio Strepparola, Viviana Boselli, Mauro Scapin
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Patent number: 5372743Abstract: 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: GrantFiled: August 9, 1993Date of Patent: December 13, 1994Assignees: Nippon Paint Co., Ltd., Asahi Denka Kogyo K.K.Inventors: Satoshi Miyamoto, Isao Kawasaki, Kaoru Komiya
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Patent number: 5344930Abstract: 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: GrantFiled: November 8, 1993Date of Patent: September 6, 1994Assignee: Alliance Pharmaceutical Corp.Inventors: Jean G. Riess, Francois Jeanneaux, Marie-Pierre Krafft, Catherine Santaella, Pierre Vierling
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Patent number: 5322871Abstract: 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: GrantFiled: April 20, 1993Date of Patent: June 21, 1994Assignee: Ciba-Geigy CorporationInventors: Rita Pitteloud, Peter Hofmann, Rudolf Maul, Volker Schenk, Eduard Troxler, Horst Zinke
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Patent number: 5312953Abstract: 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: GrantFiled: August 17, 1993Date of Patent: May 17, 1994Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Ranjit Kumar
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Patent number: 5306436Abstract: 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: GrantFiled: August 26, 1991Date of Patent: April 26, 1994Assignee: Institut Francais du PetroleInventors: Maurice Born, Ourida Aberkane, Jean-Luc Mieloszynski, Daniel Paquer, Guy Parc
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Patent number: 5266722Abstract: 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: GrantFiled: November 9, 1988Date of Patent: November 30, 1993Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Ranjit Kumar
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Patent number: 5219845Abstract: 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: GrantFiled: February 11, 1992Date of Patent: June 15, 1993Assignee: The University of British ColumbiaInventors: Hassan Salari, Robert Bittman
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Patent number: 5202111Abstract: 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: GrantFiled: May 9, 1991Date of Patent: April 13, 1993Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.Inventors: Suree M. Spaltro, Michael P. Aronson
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Patent number: 5151414Abstract: 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: GrantFiled: July 31, 1991Date of Patent: September 29, 1992Assignee: SIMES Societa Italiana Medicinali e Sintetici S.p.A.Inventors: Cesare Casagrande, Gabriele Norcini, Francesco Santangelo, Claudio Semeraro
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Patent number: 5132446Abstract: 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: GrantFiled: October 25, 1990Date of Patent: July 21, 1992Assignee: Daikin Industries, Ltd.Inventors: Takashi Tohzuka, Yoshiaki Kataoka, Sueyoshi Ishikawa
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Patent number: 5126474Abstract: 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: GrantFiled: September 20, 1990Date of Patent: June 30, 1992Assignee: Ciba-Geigy CorporationInventor: Rosemarie Topfl
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Patent number: 5091550Abstract: 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: GrantFiled: April 20, 1990Date of Patent: February 25, 1992Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirtland P. Clark
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Patent number: 5041597Abstract: 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: GrantFiled: May 25, 1990Date of Patent: August 20, 1991Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Bernd Fabry, Hans-Herbert Friese, Friedrich Pieper, Guenter Uphues
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Patent number: 5015635Abstract: 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: GrantFiled: July 26, 1989Date of Patent: May 14, 1991Assignee: Bayer AktiengesellschaftInventors: Herbert Sommer, Jurgen Hartwig, Hans-Detlef Matthaei
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Patent number: 4994581Abstract: 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: GrantFiled: December 19, 1989Date of Patent: February 19, 1991Assignee: Kao CorporationInventors: Motoru Takeda, Mitsuharu Masuda, Takashi Imamura, Tomihiro Kurosaki
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Patent number: 4981989Abstract: 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: GrantFiled: November 8, 1989Date of Patent: January 1, 1991Assignee: American Cyanamid CompanyInventors: Allan Wissner, Phaik E. Sum, Robert E. Schaub
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Patent number: 4939283Abstract: 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: GrantFiled: December 15, 1988Date of Patent: July 3, 1990Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Kinya Yokota, Akinobu Ichihara
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Patent number: 4933478Abstract: 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: GrantFiled: September 1, 1988Date of Patent: June 12, 1990Assignee: Ciba-Geigy CorporationInventors: Peter S. Wardleworth, Eric K. Baylis
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Patent number: 4918211Abstract: 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: GrantFiled: November 10, 1987Date of Patent: April 17, 1990Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Kinya Yokota, Akinobu Ichihara, Hitoshi Shinike
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Patent number: 4912245Abstract: 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: GrantFiled: June 16, 1987Date of Patent: March 27, 1990Assignee: Rhone-Poulenc ChimieInventors: Yvette Girardeau, Christian Segaud
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Patent number: 4889945Abstract: 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: GrantFiled: April 6, 1989Date of Patent: December 26, 1989Assignee: Sandoz Ltd.Inventor: Achim Wiedemann
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Patent number: 4851161Abstract: .beta.-substituted polyfluoropropionate salts, derivatives and copolymers and processes for the preparation thereof.Type: GrantFiled: December 16, 1986Date of Patent: July 25, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 4830764Abstract: 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: GrantFiled: October 23, 1987Date of Patent: May 16, 1989Assignee: Sandoz Ltd.Inventor: Achim Wiedemann
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Patent number: 4831176Abstract: 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: GrantFiled: December 30, 1987Date of Patent: May 16, 1989Assignee: Berol Kemi ABInventors: Krister Holmberg, Eva sterberg
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Patent number: 4814514Abstract: 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: GrantFiled: May 6, 1987Date of Patent: March 21, 1989Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Kinya Yokota, Akinobu Ichihara
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Patent number: 4798872Abstract: 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: GrantFiled: April 28, 1986Date of Patent: January 17, 1989Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Biau-Hung Chang
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Patent number: 4781722Abstract: 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: GrantFiled: March 1, 1988Date of Patent: November 1, 1988Assignee: Hoechst AktiengesellschaftInventors: Hans-Jerg Kleiner, Rolf Kleber, Lothar Jaeckel
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Patent number: 4754048Abstract: 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: GrantFiled: November 7, 1986Date of Patent: June 28, 1988Assignee: The Dow Chemical CompanyInventors: Chester E. Pawloski, Sally P. Ginter
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Patent number: 4727177Abstract: 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: GrantFiled: March 6, 1986Date of Patent: February 23, 1988Assignee: Takemoto Yushi Kabushiki KaishaInventors: Masatsugu Saiki, Yoshio Imai, Makoto Takagi