Preparing By Utilizing Halogen, Heavy Metal, Or Aluminum Containing Material Patents (Class 568/68)
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Patent number: 8440736Abstract: 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: GrantFiled: April 6, 2009Date of Patent: May 14, 2013Assignee: University of Southern MississippiInventors: Charles E. Hoyle, Sergei Nazarenko, Huanyu Wei
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Publication number: 20100292481Abstract: 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: ApplicationFiled: December 17, 2008Publication date: November 18, 2010Inventors: Seiji Oda, Takashi Kamikawa
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Patent number: 7829155Abstract: 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: GrantFiled: October 12, 2007Date of Patent: November 9, 2010Assignee: The University of Memphis Research FoundationInventors: Evgueni Pinkhassik, Larry Todd Banner, Benjamin T. Clayton
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Patent number: 7112697Abstract: 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: GrantFiled: July 12, 2004Date of Patent: September 26, 2006Assignee: University of MassachusettsInventors: Dhandapani Venkataraman, Craig G. Bates, Rattan K. Gujadhur
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Patent number: 6974877Abstract: 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: GrantFiled: September 27, 2002Date of Patent: December 13, 2005Assignee: 3M Innovative Properties CompanyInventors: Dennis E. Vogel, Kim M. Vogel
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Publication number: 20040225157Abstract: 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: ApplicationFiled: January 8, 2003Publication date: November 11, 2004Inventors: Hanns Wurziger, Guido Pieper
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Patent number: 6667421Abstract: 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: GrantFiled: August 28, 2002Date of Patent: December 23, 2003Assignee: E. I. du Pont de Nemours and CompanyInventor: Stephen E. Jacobson
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Patent number: 6054623Abstract: 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 protectType: GrantFiled: December 18, 1998Date of Patent: April 25, 2000Assignee: AlliedSignal Inc.Inventors: David Ryckman, Mingbao Zhang, Guohua Chen
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Patent number: 5780402Abstract: Novel alkylated thiophenols are high temperature stable lubricant fluids having low temperature properties and excellent load-carrying properties and additive solubility.Type: GrantFiled: August 22, 1991Date of Patent: July 14, 1998Inventor: Leslie R. Rudnick
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Patent number: 5728887Abstract: 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: GrantFiled: April 10, 1996Date of Patent: March 17, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Stephen Ernest Jacobson
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Patent number: 5338886Abstract: 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: GrantFiled: May 17, 1993Date of Patent: August 16, 1994Assignee: Eastman Chemical CompanyInventors: Mark Rule, James T. Tanner, III
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Patent number: 5266705Abstract: 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: GrantFiled: December 29, 1992Date of Patent: November 30, 1993Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Naoto Yazawa, Yoshinori Saito, Hidetaka Hiyoshi
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Patent number: 5171915Abstract: 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: GrantFiled: February 21, 1989Date of Patent: December 15, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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Patent number: 5136114Abstract: 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: GrantFiled: April 30, 1990Date of Patent: August 4, 1992Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 5118858Abstract: 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: GrantFiled: October 19, 1990Date of Patent: June 2, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Haydn W. R. Williams, Robert N. Young, Robert J. Zamboni
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Patent number: 5032380Abstract: 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: GrantFiled: March 5, 1990Date of Patent: July 16, 1991Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Thaddeus Novak, Paul M. Davis
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Patent number: 5004841Abstract: 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: GrantFiled: March 14, 1989Date of Patent: April 2, 1991Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Joseph J. Maj, Stephen C. Rocke
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Patent number: 4978796Abstract: 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: GrantFiled: January 31, 1990Date of Patent: December 18, 1990Assignee: Phillips Petroleum CompanyInventor: James E. Shaw
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Patent number: 4948827Abstract: 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: GrantFiled: October 25, 1989Date of Patent: August 14, 1990Assignee: Societe Francaise HoechstInventor: Yani Christidis
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Patent number: 4891448Abstract: 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: GrantFiled: November 23, 1987Date of Patent: January 2, 1990Assignee: The Dow Chemical CompanyInventors: Juan Garces, Joseph J. Maj, G. John Lee, Stephen C. Rocke
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Patent number: 4794205Abstract: 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: GrantFiled: December 10, 1986Date of Patent: December 27, 1988Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Kenneth G. Davenport
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Patent number: 4767884Abstract: 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: GrantFiled: September 17, 1987Date of Patent: August 30, 1988Assignee: Akzo America Inc.Inventor: Stanley B. Mirviss
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Patent number: 4754072Abstract: 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: GrantFiled: March 9, 1987Date of Patent: June 28, 1988Assignee: Stauffer Chemical CompanyInventor: Elliott Bay
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Patent number: 4740623Abstract: 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: GrantFiled: January 30, 1987Date of Patent: April 26, 1988Assignee: Stauffer Chemical CompanyInventor: James B. Heather
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Patent number: 4542233Abstract: 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: GrantFiled: July 20, 1983Date of Patent: September 17, 1985Assignee: Biaschim S.p.A.Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
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Patent number: 4209469Abstract: 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: GrantFiled: December 19, 1978Date of Patent: June 24, 1980Assignee: Ciba-Geigy AGInventors: Hans Thies, Fred von Kaenel