Preparing By Utilizing Halogen, Heavy Metal, Or Aluminum Containing Material Patents (Class 568/68)
  • Patent number: 8440736
    Abstract: The present invention provides modified multifunctional thiol-ene monomers wherein one or more thiols are reacted with a Michael addition reactive double bond compound. The present invention further discloses photocurable thiol-ene formulations comprising thiol-ene monomers including the modified multifunctional thiols. The present invention further discloses photocurable thiol-ene formulations comprising thiol-ene monomers and Michael addition reactive double bond molecules and a Michael catalyst. The formulations of the present invention can be photocured to make films or coatings. In a further disclosure, the formulations, including those comprised of unmodified multifunctional thiols and multifunctional enes, are photocured to form films applied to non-flexible or flexible polymer or non-polymer substrates suitable for food packaging, electronic products, optical products and other applications and free-standing films.
    Type: Grant
    Filed: April 6, 2009
    Date of Patent: May 14, 2013
    Assignee: University of Southern Mississippi
    Inventors: Charles E. Hoyle, Sergei Nazarenko, Huanyu Wei
  • Publication number: 20100292481
    Abstract: A method for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of a nickel compound, a ligand, a manganese salt and a metal reducing agent.
    Type: Application
    Filed: December 17, 2008
    Publication date: November 18, 2010
    Inventors: Seiji Oda, Takashi Kamikawa
  • Patent number: 7829155
    Abstract: The present invention provides a new monomer and methods of using the monomer to fabricate robust polymer surface coatings with controlled thicknesses between 1 and 5 nanometers. The coatings are composed of a new material containing polymerized monomers of 4-vinylbenzenepropanethiol. The polymer surface coating may be applied to metal and silicon. The method includes exposing a metal substrate to a solution of the monomer in hexanes in order to deposit a monolayer of the monomer onto the metal surface. The substrate is then irradiated with ultraviolet radiation in order to graft a thin polymer coating onto the surface. The procedure can be repeated in order to control the thickness of the coating between about 1 nm and 5 nm. Alternatively, thermally initiated polymerization or deposition of partially oligomerized monomers onto the surface provides nanothin coatings with identical performance.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: November 9, 2010
    Assignee: The University of Memphis Research Foundation
    Inventors: Evgueni Pinkhassik, Larry Todd Banner, Benjamin T. Clayton
  • Patent number: 7112697
    Abstract: A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.
    Type: Grant
    Filed: July 12, 2004
    Date of Patent: September 26, 2006
    Assignee: University of Massachusetts
    Inventors: Dhandapani Venkataraman, Craig G. Bates, Rattan K. Gujadhur
  • Patent number: 6974877
    Abstract: A process for preparing substituted pentacene compounds comprises the step of cyclizing substituted bis(benzyl)phthalic acids using an acid composition comprising trifluoromethanesulfonic acid, the substituted bis(benzyl)phthalic acids being represented by the following general formulas: wherein each R (that is, each of the groups R1 through R8) is independently an electron-donating group, a halogen atom, a hydrogen atom, or a combination thereof.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: December 13, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Dennis E. Vogel, Kim M. Vogel
  • Publication number: 20040225157
    Abstract: The present invention relates to a process for the reduction of aliphatic, aromatic or heterocyclic organic compounds by means of hydrides and/or derivatives thereof.
    Type: Application
    Filed: January 8, 2003
    Publication date: November 11, 2004
    Inventors: Hanns Wurziger, Guido Pieper
  • Patent number: 6667421
    Abstract: This invention relates to a process for the production of an aryl thiol, which comprises hydrogenating an aryl sulfonyl chloride in a solvent in the presence of a palladium catalyst and a base whose conjugate acid has a pKa of about 2 or greater, wherein the base is selected from the group consisting of ionic bases soluble in water and tertiary amines soluble in the solvent, the tertiary amines not having a methyl group attached to the amine nitrogen.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: December 23, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Stephen E. Jacobson
  • Patent number: 6054623
    Abstract: A method for the preparation of hydroxythiol compounds by reacting a hydroxyl-protected halide compound having the structure:X--R--OPgwith magnesium in a Grignard-suitable solvent to form a hydroxyl-protected magnesium halide compound, wherein R is selected from substituted or unsubstituted aliphatic radicals, substituted or unsubstituted cyclic aliphatic radicals, substituted or unsubstituted aromatic radicals, substituted or unsubstituted araliphatic radicals and substituted or unsubstituted heterocyclic radicals; Pg is a protecting group; and X is selected from the group consisting of F, Cl, Br and I; then reacting said hydroxyl-protected magnesium halide compound with sulfur in the Grignard-suitable solvent to form a hydroxyl-protected thiomagnesium halide compound; and hydrolyzing the protected hydroxyl group to form a hydroxythiomagnesium halide compound and converting the thiomagnesium halide to a thiol; wherein the protecting group is selected so that species formed by the de-protection of the protect
    Type: Grant
    Filed: December 18, 1998
    Date of Patent: April 25, 2000
    Assignee: AlliedSignal Inc.
    Inventors: David Ryckman, Mingbao Zhang, Guohua Chen
  • Patent number: 5780402
    Abstract: Novel alkylated thiophenols are high temperature stable lubricant fluids having low temperature properties and excellent load-carrying properties and additive solubility.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: July 14, 1998
    Inventor: Leslie R. Rudnick
  • Patent number: 5728887
    Abstract: A process for the preparation of a thiol comprising reacting hydrogen with a thiocyanate or disulfide wherein the reaction with thiocyanate is conducted in the presence of a catalyst comprising a Group VIII metal or a mixture thereof; and the reaction with thiocyanate or with disulfide is conducted in the presence of a catalyst comprising a Group VIII metal or mixture thereof in the presence of a modifier metal selected from a group consisting of Group IB, Group IIB, Group IIIA, Group IVA, Group VA and Group VIA metal or mixture thereof, said catalyst being on a porous insoluble support.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: March 17, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Stephen Ernest Jacobson
  • Patent number: 5338886
    Abstract: Disclosed is a process for preparation of an aromatic thiol corresponding to the structureA-(SH)nwhereinA is a substituted or unsubstituted aromatic radical and n is 1, 2, 3, 4, 5 or 6 comprising contacting at a temperature of at least 80.degree. C. an aromatic halide corresponding to the structureA-XmwhereinA is the same as above, X is bromine oriodine and n is 1, 2, 3, 4, 5, or 6with thiourea in the presence of nickel metal.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: August 16, 1994
    Assignee: Eastman Chemical Company
    Inventors: Mark Rule, James T. Tanner, III
  • Patent number: 5266705
    Abstract: A process for production of 2-acetylbenzo[b]thiophene represented by the formula (I): ##STR1## comprising the steps of: (1) reacting 2-halogenobenzaldehyde represented by the formula (II): ##STR2## wherein X represents a halogen atom, with a compound represented by the formula (III):H.sub.i S.sub.j M.sub.kwherein M represents an alkali metal, i represents zero or 1, j represents an integer of at least 1, and k represents an integer of 1 or 2, and preferably also with sulfur; and(2) reacting the reaction product with a monohalogenoacetone represented by the formula (IV) ##STR3## wherein X.sup.1 represents a halogen atom.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: November 30, 1993
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Naoto Yazawa, Yoshinori Saito, Hidetaka Hiyoshi
  • Patent number: 5171915
    Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5136114
    Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5118858
    Abstract: Disclosed herein are /.sup.35 S/-labelled compound of the formula (I):(C.sub.6 H.sub.5).sub.3 C.sup.35 SHand processes therefor. This Compound (I) is useful as an intermediate for the introduction of sulfur isotope into a variety of compounds. For example, it is useful in the introduction of sulfur isotope into important compounds such as 6-mercaptopurine, 5-[3-(2-(7-chloroquinolin-2-yl)ethenyl)phenyl]-8-dimethylcarbamyl-4,6-dith ioactanoic acid, a potent antagonist of leukotriene D.sub.4 ; thiophosphoric acid derivatives, photo-affinity reagents and the like.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: June 2, 1992
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Haydn W. R. Williams, Robert N. Young, Robert J. Zamboni
  • Patent number: 5032380
    Abstract: Fluorescence properties of the product of the reaction of the 2-naphthalenethiolate ion and 2-chloroethylethylsulfide or bis(2-chloroethyl)sulfide are described. The fluorescence of the latter reaction is used as the basis of a new detection method for 2-chloroethylethylsulfide. The detection method is capable of detecting 2-chloroethylethylsulfide at levels down to 0.2 micrograms per milliliter.
    Type: Grant
    Filed: March 5, 1990
    Date of Patent: July 16, 1991
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Thaddeus Novak, Paul M. Davis
  • Patent number: 5004841
    Abstract: Aromatic compounds, such as benzene or biphenyl, are alkylated with an alkylating agent having from one to eight carbons atoms, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted aromatic compounds enriched in the linear alkylated isomers, such as p-diisopropylbenzene or p,p'-di(isopropyl)biphenyl, respectively. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: April 2, 1991
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Joseph J. Maj, Stephen C. Rocke
  • Patent number: 4978796
    Abstract: A process using N-alkylpyrrolidone solvents, such as N-methylpyrrolidone (NMP), for the preparation of aromatic thiols, from the reaction of aryl halides and alkali metal alkanethiolate. This process produces aromatic thiols in higher yields and purity.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: December 18, 1990
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 4948827
    Abstract: This new thiophenol, prepared by reduction of tertiary butyl-4-toluenesulfonyl-2-chloride with the zinc-sulphuric acid couple, can be used as a stabilizer for vinyl chloride polymers, as a chain-transfer agent and as a peptizer.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: August 14, 1990
    Assignee: Societe Francaise Hoechst
    Inventor: Yani Christidis
  • Patent number: 4891448
    Abstract: Polycyclic aromatic compounds, such as biphenyl, are alkylated with an alkylating agent, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted polycyclic aromatic compounds enriched in the para alkylated isomers, such as p,p'-di(isopropyl)biphenyl. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of polycyclic aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: January 2, 1990
    Assignee: The Dow Chemical Company
    Inventors: Juan Garces, Joseph J. Maj, G. John Lee, Stephen C. Rocke
  • Patent number: 4794205
    Abstract: A method is provided for preparing alkenylthiophenols, e.g., para-vinylthiophenol, or their esters, e.g., para-vinylthiophenol acetate by reacting a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone (4-HAP) with an N,N-di(organo)thiocarbamoyl halide, e.g., N,N-dimethylthiocarbamoyl chloride (DMTC) to form an O-(acylaryl) N,N-di(organo)thiocarbamate, e.g., O-(4'-acetophenyl) N,N-dimethylthiocarbamate, and pyrolytically rearranging the latter compound to form an S-(acylaryl) N,N-di(organo)thiocarbamate, e.g., S-(4-4- -acetophenyl) N,N-dimethylthiocarbamate. In one procedure, the latter compound is directly reduced to form an S-(1-hydroxyalkylaryl) N,N-di(organo) thiocarbamate, e.g., S-[4'-(1-hydroxyethyl)phenyl] N,N-dimethylthiocarbamate, which is either hydrolyzed to form a (1-hydroxyalkyl) thiophenol, e.g., 4'-(1-hydroxyethyl) thiophenol, which optionally after acylation of its thiol group, is dehydrated to form the alkenylthiophenol wherein the double bond is at the ring-bonded carbon atom, e.g.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: December 27, 1988
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Kenneth G. Davenport
  • Patent number: 4767884
    Abstract: A sulfonic acid is reduced to a thiol by heating the acid under carbon monoxide pressure in the presence of a rhodium carbonyl catalyst.
    Type: Grant
    Filed: September 17, 1987
    Date of Patent: August 30, 1988
    Assignee: Akzo America Inc.
    Inventor: Stanley B. Mirviss
  • Patent number: 4754072
    Abstract: Thiophenols are formed from phenols by first reacting a phenol with thiophosgene to form an aryl chlorothionoformate which is subjected to a halogen exchange reaction using an alkali metal fluoride to yield the corresponding fluorothionoformate. This fluorothionoformate is then rearranged to the corresponding fluorothiolformate by heating and the resulting fluorothiolformate is then hydrolyzed to yield the desired thiophenol.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: June 28, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Elliott Bay
  • Patent number: 4740623
    Abstract: A method for the preparation of benzyl mercaptan is disclosed which comprises reacting a benzyl halide of the formula ##STR1## wherein X is chlorine or bromine, with an alkali metal hydrosulfide salt, at a temperature and for a sufficient period of time to cause formation of the benzyl mercaptan, said reaction being conducted under a hydrogen sulfide atmosphere at a temperature of about 50.degree. C. until approximately 90% of the starting material is converted to the benzyl mercaptan, then increasing the temperature to about 80.degree. C. for the balance of the reaction, the initial concentration of said hydrosulfide salt in solution being between about 5% and about 30% by weight.
    Type: Grant
    Filed: January 30, 1987
    Date of Patent: April 26, 1988
    Assignee: Stauffer Chemical Company
    Inventor: James B. Heather
  • Patent number: 4542233
    Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: September 17, 1985
    Assignee: Biaschim S.p.A.
    Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
  • Patent number: 4209469
    Abstract: A process for the production of an aryl thiol, which comprises hydrogenating an aryl sulfochloride in a protic or aprotic solvent in the presence of platinum as catalyst, at a temperature between 100.degree. and 180.degree. C., with hydrogen under a pressure of 2 to 140 bar, in a single reaction step.
    Type: Grant
    Filed: December 19, 1978
    Date of Patent: June 24, 1980
    Assignee: Ciba-Geigy AG
    Inventors: Hans Thies, Fred von Kaenel