Sulfur Containing Patents (Class 568/18)
  • Patent number: 6111143
    Abstract: This invention relates to a sulfonium salt, including its manufacturing method, which is effectively used as a photoacid initiator or radical photoinitiator during polymerization and a photoacid generator, leaving the protection groups of organic compounds, especially as an useful photoacid generator of the chemically amplified photoresist employed in semiconductor materials. Since the sulfonium salt of this invention, so prepared via one-step reaction between sulfoxide compound and aromatic compound in the presence of perfluoroalkanesulfonic anhydride, has the advantages in that by overcoming some shortcomings of the prior art to prepare the sulfonium salt via two steps using Grinard reagent, this invention may provide a novel sulfonium salt with higher yield which cannot be achieved in the prior art and also to prepare even any conventional sulfonium salt having better yield.
    Type: Grant
    Filed: August 27, 1998
    Date of Patent: August 29, 2000
    Assignee: Korea Kumbo Petrochemical Co., Ltd.
    Inventors: Joo-Hyeon Park, Dong-Chul Seo, Sun-Yi Park, Seong-Ju Kim
  • Patent number: 6031014
    Abstract: Cationic polymerization initiators of formula ##STR1## are disclosed. The acyl sulfonium salts of the present invention differ from known acyl sulfonium initiators in that the substituents R.sup.2 and R.sup.3 on the sulfur are larger and more complex than the lower alkyl and lower alkylene of known photoinitiators. Processes for the synthesis of the novel acyl sulfonium salts and prepolymer compositions containing them are also disclosed.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: February 29, 2000
    Inventor: James V. Crivello
  • Patent number: 6002029
    Abstract: Lipid prodrugs of phosphonoacids and their analogs that have increased antiviral activity over the parent drugs in inhibiting cytomegalovirus and other susceptible viruses.
    Type: Grant
    Filed: December 8, 1997
    Date of Patent: December 14, 1999
    Inventors: Karl Y. Hostetler, Ganesh D. Kini
  • Patent number: 5945082
    Abstract: Novel cyanophosphorus compounds are disclosed. The preparation, purification, and characterization of dicyanophosphinate, cyanopolyphosphates, tricyanocyclotriphosphonate and tetracyanocyclotetraphosphate are presented.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: August 31, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5935542
    Abstract: The novel cyanophosphonate compounds of the present invention include cyanophosphonate salts, cyanophosphonate monoacid salts, cyanophosphonate monoacid esters, cyanophosphonate monoester salts and cyanophosphonate methylester salts.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: August 10, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5858317
    Abstract: A process for preparing cyanophosphonate derivatives involves contacting phosphoric anhydride (P.sub.4 O.sub.10) and a cyanide, preferably in the presence of a Lewis base, in a reaction mixture under sufficient conditions to produce a cyanophosphonate derivative. The cyanophosphonate derivative can be subsequently hydrogenated to produce an aminomethylphosphonate derivative.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Monsanto Company
    Inventors: Patrick J. Lennon, Sergey G. Vulfson
  • Patent number: 5808140
    Abstract: A process for synthesizing disulfides and sulfhydryl compounds which are useful pharmaceuticals. The process includes a two step, single pot process for preparing disulfides from an alkenyl sulfonate salt. The disulfides are useful as toxicity mitigating agents of chemotherapeutic drugs, such as certain platinum complexes, and as use therapeutic drugs for a variety of conditions in mammals.The two step process involves first the conversion of the starting reagent to a mercaptane sulfonate, then an oxidation to the desired disulfide.
    Type: Grant
    Filed: September 24, 1997
    Date of Patent: September 15, 1998
    Assignee: BioNumerik Pharmaceuticals, Inc.
    Inventor: Kochat Haridas
  • Patent number: 5798396
    Abstract: The present invention is directed to sulfonium salt-containing compounds represented by a following general formula; ##STR1## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, each of R.sub.1 may be different from the others when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or aromatic carbonyloxy, and R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: August 25, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Hiroo Muramoto
  • Patent number: 5750740
    Abstract: A process for transforming a carbonyl compound into its corresponding epoxide, which comprises contacting the carbonyl compound with either trimethylsulphonium hydrogen sulphate and/or bis(trimethylsulphonium) sulphate or trimethylsulphoxonium hydrogen sulphate and/or bis(trimethylsulphoxonium) sulphate, in the presence of a base.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: May 12, 1998
    Assignee: Zeneca Limited
    Inventors: Raymond Vincent Heavon Jones, Elizabeth Shearer Currie Simpson
  • Patent number: 5698501
    Abstract: Sulphur-containing substances are derived from mono- or polyethylenic hydrocarbons by sulphurization using elemental sulphur in the presence of an alkali metal carbonate or bicarbonate and in the presence of water and/or at least one alkyleneglycol.The sulphur-containing substances, which may contain 20% to 70% by weight of sulphur, are generally soluble in lubricants to improve antiwear and extreme pressure properties. They can also be used as sulphurization agents, in particular for preparing catalysts for refining petroleum products.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: December 16, 1997
    Assignee: Institut Francais Du Petrole
    Inventors: Thierry Lacome, Bruno Delfort, Maurice Born
  • Patent number: 5696277
    Abstract: Lipid prodrugs of phosphonoacids and their analogs that have increased antiviral activity over the parent drugs in inhibiting cytomegalovirus and other susceptible viruses.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: December 9, 1997
    Assignee: Karl Y. Hostetler
    Inventors: Karl Y. Hostetler, Ganesh D. Kini
  • Patent number: 5679626
    Abstract: Sulphur-containing substances are derived from mono- or polyethylenic hydrocarbons by sulphurization using elemental sulphur in the presence of at least one alkali or alkaline-earth metal hydroxide and at least one glycol or polyglycol, or glycol or polyglycol monoether and/or water. Sulphur-containing substances, which may contain 20% to 70% by weight of sulphur, are generally soluble in lubricants to improve antiwear and extreme pressure properties. They can also be used as sulphurization agents, in particular for preparing catalysts for refining petroleum products.
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: October 21, 1997
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Bruno Delport, Thierry Lacome
  • Patent number: 5637727
    Abstract: A process for transforming a carbonyl compound into its corresponding epoxide, which comprises contacting the carbonyl compound with either trimethylsulphonium hydrogen sulphate and/or bis(trimethylsulphonium) sulphate or trimethylsulphoxonium hydrogen sulphate and/or bis(trimethylsulphoxonium) sulphate, in the presence of a base.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: June 10, 1997
    Assignee: Zeneca Limited
    Inventors: Raymond V. H. Jones, Elizabeth S. C. Simpson
  • Patent number: 5596122
    Abstract: The present invention is directed to disulfonyl methane compounds for the control of parasites in vertebrate animals.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: January 21, 1997
    Assignee: Eli Lilly and Company
    Inventor: David I. Wickiser
  • Patent number: 5567849
    Abstract: A borane-sulfide represented by the formulaBH.sub.3.SR.sup.1 R.sup.2wherein B is boron, H is hydrogen, R.sup.1 and R.sup.2 each are straight or branched chain alkyl or alkoxy with at least one R being a branched chain when both R.sup.1 and R.sup.2 are alkyl, and S is sulfur. The compounds are hydroboration agents.
    Type: Grant
    Filed: May 9, 1995
    Date of Patent: October 22, 1996
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5534557
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 9, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5532395
    Abstract: This invention relates to novel chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: July 2, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Mark J. Burk
  • Patent number: 5462810
    Abstract: A magnetic recording medium comprises a nonmagnetic substrate and at least one ferromagnetic metal layer applied thereon and a protective layer formed on this metal layer and consisting of a compound which consists of an unfluorinated or partially fluorinated alkyl radical and a disulfide, hydroxyl or keto group.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Magnetics GmbH
    Inventors: Harald Keller, Ulrich Jaeger, Helmut Steininger, Helmut Kopke, Klaus D. Schomann, Hans-Peter Schildberg
  • Patent number: 5396011
    Abstract: An aromatic compound (such as benzene) is alkylated with a alkene (such as propylene) by contacting the two compounds together in the presence of a tungsten on zirconia catalyst. The reaction preferably takes place at elevated temperature and elevated pressure. The process of the invention has very high selectivity and conversion, and produces no or only very low amounts of undesirable oligomers (as measured by bromine number).
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: March 7, 1995
    Assignee: Mallinckrodt Chemical, Inc.
    Inventor: Deborah K. Kuhn
  • Patent number: 5286395
    Abstract: Olefin polysulfide compositions of high sulfur content and of very low chlorine content are obtained by a process comprising the steps of: (1) reacting sulfur mono- and/or dichloride with at least one aliphatic monoolefin of 2-12 carbon atoms, to form an addition product or "adduct", (2) reacting hydrogen sulfide with an alkali hydroxide or ammonium hydroxide dissolved in at least one substantially anhydrous C.sub.1 -C.sub.4 aliphatic monoalcohol, with optional addition of elemental sulfur, (3) contacting said "adduct" together with at least one monohalogenated hydrocarbon compound, with the alcoholic solution obtained at the end of step (2), (4) heating the resultant mixture from step (3), removing the monoalcohol, while adding water, and (5) after settling and removal of the aqueous phase, recovering the organic phase formed at least in major part of the desired olefin polysulfide composition. These compositions, of sulfur content up to 65% by weight and of chlorine content generally lower than about 0.
    Type: Grant
    Filed: May 14, 1992
    Date of Patent: February 15, 1994
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Lucienne Briquet, Guy Parc
  • Patent number: 5274148
    Abstract: This invention relates to C.sub.14 to C.sub.20 alkoxy monophenyl sulfonium salt initiators having the formula ##STR1## wherein R is C.sub.14 to C.sub.20 alkyl; R.sub.1 and R.sub.2 are each independently C.sub.4 to C.sub.20 alkyl and X.sup.- is a non-basic, nonnucleophilic anion, which initiators are employed in the polymerization of mono- and poly- functional glycidyl ethers, alpha-olefin oxides and vinyl monomers or oligomers.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: December 28, 1993
    Assignee: ISP Investments, Inc.
    Inventors: James A. Dougherty, James V. Crivello
  • Patent number: 5247113
    Abstract: Sulfonium salts of the formulae I to IV ##STR1## in which A is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, phenyl which is unsubstituted or mono- or polysubstituted by C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, nitro, phenyl, phenoxy, alkoxycarbonyl having 1-4 C atoms in the alkoxy radical or acyl having 1-12 C atoms, Ar, Ar.sup.1 and Ar.sup.2, independently of one another, are each unsubstituted or mono- or polysubstituted phenyl, or naphthyl which is unsubstituted or mono- or polysubstituted each arylene is an unsubstituted or mono- or polysubstituted phenylene or unsubstituted or mono- or polysubstituted naphthylene and Q.sup..crclbar. is SbF.sub.6.sup.-, AsF.sub.6.sup.- or SbF.sub.5 OH.sup.- are valuable curing agents and curing accelerators in the heat-curing of cationically polymerizable compounds, preferably epoxy resins.
    Type: Grant
    Filed: January 7, 1991
    Date of Patent: September 21, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Roth, Beat Muller
  • Patent number: 5218103
    Abstract: The present invention relates to new and useful nucleside thiophosphoramidite, polynucleotide dithioate phosphoramidite and polynucleotide phosphorothioamidate phosphoramidite compounds as well as the process whereby these compounds can be used for synthesizing new monoucleotides and polynucleotides having phosphorodithioate, phosphorothioamidate, phosphorothiotriesters and phosphorothioate internucleotide linkages.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: June 8, 1993
    Assignee: University Patents, Inc.
    Inventors: Marvin H. Caruthers, Yun-Xi Ma, Eric K. Yau, John Nielsen, Wolfgang Brill
  • Patent number: 5191124
    Abstract: Sulfonium salts of the general formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are identical or different and are aliphatic and/or aromatic radicals which may contain heteroatoms, or two of the radicals R.sup.1 and R.sup.3 are bonded to one another to form a ring, with the proviso that one or more of the radicals R.sup.1 to R.sup.3 contain one or more acid-cleavable groups, or one of the radicals R.sup.1 to R.sup.3 is bonded to one or more further sulfonium salt radicals, if desired via acid-cleavable groups, and X.sup..crclbar. is a non-nucleophilic counter-ion, are suitable as photoinitiators for cationic polymerization.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: March 2, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Andreas Boettcher
  • Patent number: 5178781
    Abstract: A process for producing an over-based sulfurized alkaline earth metal phenate type detergent, which comprises reacting a phenol and a dihydric alcohol with an alkaline earth metal reagent to carry out a metal addition reaction, and reacting sulfur therewith to carry out a sulfurization reaction, and then reacting carbon dioxide therewith to carry out a carbon dioxide treatment, characterized in that the metal addition reaction and the sulfurization reaction are carried out under pressure and closed conditions. The sulfurization reaction may be carried out simultaneously with the metal addition reaction, or, alternatively, with the carbon dioxide treatment after the metal addition reaction. Furthermore, the sulfurization reaction may be carried out between the metal addition reaction and the carbon dioxide treatment.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: January 12, 1993
    Assignees: Cosmo Oil Co., Ltd., Cosmo Research Institute
    Inventors: Takashi Hori, Sanae Ueda, Yoshihiro Kojima, Masato Goto, Hitoshi Kumagai
  • Patent number: 5152826
    Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5149857
    Abstract: A process for producing sulfonium compounds represented by the general formula (III) which comprises reacting alkylthiophenol derivatives represented by the general formula (I) and dialkyl sulfate represented by the general formula (II).General Formula (I): ##STR1## General Formula (II): (R.sup.2).sub.2 SO.sub.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Mutsuhiko Takeda, Isao Hagiwara, Fumiya Zaima, Shuzabu Sakaguchi
  • Patent number: 5116523
    Abstract: Sulfur derivatives of unsaturated oligomers formed from alpha-olefins of 2 to 20 carbon atoms which oligomer has a branch ratio of less than 0.19.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: May 26, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Noyes L. Avery, Linda A. Benjamin, Derek A. Law
  • Patent number: 5105028
    Abstract: Process for preparing one or more hetero-atoms containing hydrocarbons by contacting one or more hydrocarbons with a plasma-generated system derived from a source containing hydrogen atoms(s) and at least one hetero-atom in which process the plasma-generated system in contacted with the hydrocarbon(s) in liquid for and/or in gaseous form under conditions which allow absorption of heat released during the process of preparing said hetero-atom(s) containing hydrocarbons.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: April 14, 1992
    Assignee: Shell Oil Company
    Inventors: Jacques J. J. Dufour, Laurent Pelsez, Bruno Peltier
  • Patent number: 5047568
    Abstract: Sulfonium salts of the formula: ##STR1## wherein Ar is a fused aromatic radical; R.sub.1 is a divalent organic bridge; each R.sub.2 and R.sub.3 individually is an alkyl, aryl, alkaryl, aralkyl or substituted aryl, provided thatn not more than one of R.sub.2 and R.sub.3 is alkyl; and A is a non-nucleophilic anion; use thereof and preparation thereof.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: September 10, 1991
    Assignee: International Business Machines Corporation
    Inventors: Raymond W. Angelo, Jeffrey D. Gelorme, Joseph P. Kuczynski, William H. Lawrence, Socrates P. Pappas, Logan L. Simpson
  • Patent number: 5045229
    Abstract: Difluoromethylene compounds of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Q--CF.sub.2 --(A.sup.3 --Z.sup.2).sub.n --A.sup.4 --R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, A.sup.4, Z.sup.1, Z.sup.2, m and n are as defined herein and Q is --CO--, --O-- or --S--, can be used as components of liquid-crystalline media for liquid-crystal and electrooptical display elements.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: September 3, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Reinhard Hittich, Hans-Adolf Kurmeier, Eike Poetsch, Herbert Plach
  • Patent number: 5032592
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: July 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker
  • Patent number: 5006271
    Abstract: Sulfurized propylene based lube olefin derivatives are superior lubricating fluids with internal synergistic multifunctional extreme pressure/antiwear and antioxidant properties as well as multifunctional extreme pressure/antiwear additives for both mineral and synthetic lubricating oils as well as fuels.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: April 9, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Noyes L. Avery, Linda A. Benjamin, Andrew G. Horodysky, Derek A. Law
  • Patent number: 4966720
    Abstract: Sulfurized olefins such as isobutylene which are soluble in hydrotreated oils are prepared by reacting a basic, aqueous alcoholic solution of sodium sulfide with an adduct formed by adding olefin to sulfur monochloride at low temperatures until the mole ratio of olefin to sulfur monochloride is between about 1.7-1.9 to 1.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: October 30, 1990
    Assignee: Ethyl Petroleum Additives, Inc.
    Inventors: David J. DeGonia, Paul G. Griffin
  • Patent number: 4954274
    Abstract: Sulfurized olefins are produced by reacting sulfur monochloride with a monoolefin (e.g. isobutene) in the presence of minor amounts of an active Lewis acid (e.g. ferric chloride) to form an adduct, reacting the adduct with sulfur and sodium sulfide in an aqueous alkanol made at a ratio of 0.02-0.4 gram atom of sulfur per gram mole of sodium sulfide and then recovering the reaction product. Olefin polysulfides obtained by this method are soluble in both mineral and synthetic lubricating oils (including those of the polyalphaolefin type) and are usable as extreme pressure additives when incorporated into such lubricating oils.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: September 4, 1990
    Inventors: Edward F. Zaweski, James G. Jolly
  • Patent number: 4839069
    Abstract: Compositions of olefin polysulfides having an increased solubility in mineral oils and in synthetic oils, particularly of the hydrogenated polyalphaolefin (P.A.O.) type, are disclosed.They are prepared more particularly by reacting a sulfur monochloride with a monoolefin (e.g. isobutene) so as to form an addition product, called an adduct, which is then reacted with an alkali metal or ammonium polysulfide, obtained, for example, by reacting a mercaptan with an alkali hydroxide or ammonia in the presence of elemental sulfur. These compositions of olefin polysulfides can be used as extreme-pressure additives in gear-oils or in metal-working oils.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: June 13, 1989
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Lucienne Briquet, Jacques Lallement, Guy Parc
  • Patent number: 4795576
    Abstract: The disclosed polysulfided olefin compositions can be used in particular as extreme-pressure additives for lubricants. They are prepared by a process comprising the steps of:(1) reacting sulfur monochloride and/or dichloride with at least one monoolefin having 2 to 5 carbon atoms (generally isobutene) to form an "adduct"; (2) contacting said "adduct" jointly with an unsaturated monohalogenated hydrocarbon compound, in a proportion corresponding to a number of halogen gram-atoms from about 1 to 70% of the number of halogen gram-atoms of the assembly "monohalogenated hydrocarbon compound+adduct", with a sulfur compound (e.g. alkaline sulfide, hydrogenosulfide or polysulfide) and, mostly, element sulfur, in a proportion of 0 to 7 gram-atoms per mole of sulfur compound, within an aqueous or hydroalcoholic medium; (3) heating the mixture and, after settling in 2 phases, separating the organic phase containing the polysulfided olefin, and (4) optionally treating the obtained product with a base.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: January 3, 1989
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Lucienne Briquet, Guy Parc, Daniel Paquer
  • Patent number: 4710273
    Abstract: Olefin mixtures containing vinyl, vinylidene and internal olefins are upgraded in value by removing the vinylidene olefin content and lowering the internal olefin content by selective reaction with a sulfur halide such as S.sub.2 Cl.sub.2 followed by reaction with aqueous alkali metal hydrosulfide and optionally alkali metal sulfide. The reaction mixture is distilled to remove mainly vinyl and a reduced amount of internal olefins. The distillation residue is an effective extreme pressure additive for lubricating oil.
    Type: Grant
    Filed: August 8, 1985
    Date of Patent: December 1, 1987
    Assignee: Ethyl Corporation
    Inventor: Ted T. Okamoto
  • Patent number: 4698416
    Abstract: The process for preparing novel polymers by the reaction of a bicyclic amide acetal with sulfur at a temperature in the range of from about 25.degree. C. to about 200.degree. C. is described.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: October 6, 1987
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Harvey J. Richards
  • Patent number: 4664825
    Abstract: A sulfurized composition prepared by sulfurizing a mixture of at least one terpene and at least one other olefinic compound is described. More particularly, sulfurized compositions prepared by sulfurizing a mixture of pine oil and at least one other olefinic compound are described. Such sulfurized compositions are useful as lubricant additive compositions, and more particularly, as additive compositions in industrial and gear lubricants. The compositions when added to lubricants provide lubricants which exhibit improved antioxidant characteristics, nitrile seal compatibility and acceptable color characteristics.
    Type: Grant
    Filed: February 10, 1986
    Date of Patent: May 12, 1987
    Assignee: The Lubrizol Corporation
    Inventor: Reed H. Walsh
  • Patent number: 4645610
    Abstract: A method for the preparation of olefin polysulfides that can be used in particular as extreme pressure additives for lubricants is described. This method comprises: (1) reacting sulfur monochloride or dichloride with at least one mono-olefin containing 2 to 5 carbon atoms (in general isobutene) resulting in the formation of an adduct; (2) bringing into contact said adduct, conjointly with a hydrocarbyl halide, with a sulfur compound (for example, alkaline sulfides, hydrosulfides or polysulfides) and, in most cases, elemental sulfur, in an aqueous or aqueous-alcoholic medium; (3) heating the mixture and, after it has settled into two phases, separating the organic phase containing the olefin polysulfide; and if necessary (4) treating the product obtained with a base.The olefin polysulfides obtained contain a high proportion of sulfur, have a satisfactory viscosity and are sufficiently soluble in mineral oils as well as synthetic oils to be used as extreme pressure additives in the formulation of gear oils.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: February 24, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Guy Parc, Lucienne Briquet, Daniel Paquer
  • Patent number: 4584113
    Abstract: A sulfurized composition prepared by sulfurizing a mixture of at least one terpene and at least one other olefinic compound is described. More particularly, sulfurized compositions prepared by sulfurizing a mixture of pine oil and at least one other olefinic compound are described. Such sulfurized compositions are useful as lubricant additive compositions, and more particularly, as additive compositions in industrial and gear lubricants. The compositions when added to lubricants provide lubricants which exhibit improved antioxidant characteristics, nitrile seal compatibility and acceptable color characteristics.
    Type: Grant
    Filed: October 25, 1984
    Date of Patent: April 22, 1986
    Assignee: The Lubrizol Corporation
    Inventor: Reed H. Walsh
  • Patent number: 4563302
    Abstract: A sulfurized olefin of improved solubility in lubricating oil is made by reacting sulfur monochloride with a monoolefin (e.g. isobutylene) to form an adduct which is reacted with sodium sulfide, sodium hydrosulfide, sulfur and alkyl mercaptan (e.g. tert-butyl mercaptan) in an aqueous alcohol reaction medium.
    Type: Grant
    Filed: December 1, 1983
    Date of Patent: January 7, 1986
    Assignee: Edwin Cooper, Inc.
    Inventors: Paul G. Griffin, William Y. Lam
  • Patent number: 4492652
    Abstract: The pyrolysis of aromatic compounds with fused rings in the aromatic system which form free radicals on the peri position, for example, by eliminating a stable inorganic gas produces desirable products. These products include electrically conductive inert films. Further, with the addition of suitable inorganic compounds to the reactant, superconducting materials are obtainable. The addition of sulfur to the pyrolysis reactant also is possible and allows production of compounds useful as donors for the production of organic electrically conducting compositions.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: January 8, 1985
    Assignee: AT&T Laboratories
    Inventor: Martin L. Kaplan
  • Patent number: 4451409
    Abstract: Monomeric and polymeric triarylsulfonium complex salts which may be prepared by contacting diarylsulfoxides or polymeric arylsulfoxides with aromatic compounds in the presence of an organosulfonic acid are described. An example is tris-(4-phenoxyphenyl)sulfonium methane sulfonate prepared by reaction of bis-(4-phenoxyphenyl)sulfoxide, diphenyl ether and methane sulfonic acid. The compounds demonstrate useful corrosion inhibiting properties.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: May 29, 1984
    Assignee: The Dow Chemical Company
    Inventors: Gary R. Buske, Richard G. Pews
  • Patent number: 4337359
    Abstract: A process for the preparation of a dimethyl polysulphide of the formulaCH.sub.3 --S.sub.x --CH.sub.3in whichx is at least 1, comprising reacting a polysulphide of the formulaM.sub.y S.sub.xin whichM represents an alkali metal atom or alkaline earth metal atom, andy is 1 or 2, with O,O,O-trimethyl thiophosphate of the formula(CH.sub.3 O).sub.3 P.dbd.S.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: June 29, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Arold, Siegbert Humburger, Hans-Joachim Diehr, Helmut Porkert
  • Patent number: 4251521
    Abstract: Alkyl diaryl sulfonium salts, e.g., cyclopropyl diphenylsulfonium tetrafluoroborate, are useful as hypoglycemic agents.
    Type: Grant
    Filed: February 7, 1979
    Date of Patent: February 17, 1981
    Assignee: Sandoz, Inc.
    Inventor: Faizulla G. Kathawala
  • Patent number: 4246259
    Abstract: Higher alkyl diaryl sulfonium salts, e.g., octadecyldiphenylsulfonium tetrafluoroborate, are useful as anti-obesity agents.
    Type: Grant
    Filed: February 7, 1979
    Date of Patent: January 20, 1981
    Assignee: Sandoz, Inc.
    Inventor: Faizulla G. Kathawala
  • Patent number: 4233421
    Abstract: A thermally stable, curable fluoroelastomer composition containing sulfonium curing agent is described. The composition is curable in reactive admixture with an inorganic acid acceptor and includes:(a) a fluoroelastomer comprising vinylidene fluoride;(b) at least one triorgano sulfonium compound; and(c) at least one aromatic polyhydroxy compound.
    Type: Grant
    Filed: February 26, 1979
    Date of Patent: November 11, 1980
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Allan T. Worm
  • Patent number: 4233292
    Abstract: Cyclopropyl alkyl arylsulfonium salts, e.g., cyclopropyl n-propyl phenylsulfonium tetrafluoroborate, are useful as pharmaceutical agents.
    Type: Grant
    Filed: February 7, 1979
    Date of Patent: November 11, 1980
    Assignee: Sandoz, Inc.
    Inventor: Faizulla G. Kathawala