Carbon To Carbon Unsaturation In Substituent Q Patents (Class 564/204)
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4699965Abstract: A solventless prepolymer which is liquid at room temperature and cures at about 350.degree. F. The novel prepolymer is formed from a rubber monomer; acrylonitrile or methacrylonitrile; and an ether derivative of methylol acrylamide. The ether is formed from methylol acrylamide and an alcohol which boils above the cure temperature of the prepolymer and which preferably is hexyl carbitol. The prepolymer is formed with sufficient chain transfer agent to establish a weight average molecular weight of the prepolymer less than about 25,000. The prepolymer is heat curable to form a solid polymer with excellent compression set, tensile strength, and fuel resistivity. The method of formulating these polymers is also disclosed.Type: GrantFiled: June 28, 1985Date of Patent: October 13, 1987Assignee: Eagle Picher Industries, Inc.Inventors: Richard A. Markle, Wayne R. Melchior
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Patent number: 4686302Abstract: Nitriles of the general formula IR.sup.1 --CN (I)where R.sup.1 is a saturated or unsaturated, straight-chain, branched or cyclic alkyl radical, an aralkyl radical or an aryl radical, each of which is of not more than 20 carbon atoms and can be unsubstituted or further substituted, and (meth)acrylamide are prepared simultaneously by a process in which an aldoxime of the general formula IIIR.sup.1 --CH.dbd.NOH (III)where R.sup.1 has the above meanings, is heated at from 50.degree. to 180.degree. C. in the presence of a copper(II) carboxylate and of (meth)acrylonitrile.Type: GrantFiled: November 30, 1984Date of Patent: August 11, 1987Assignee: BASF AktiengesellschaftInventors: Franz Merger, Wolfgang Schwarz
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Patent number: 4644083Abstract: The present invention relates to a process for the production of N-substituted .alpha.,.beta.-unsaturated carboxylic acid amides, which proceeds from the .alpha.,.beta.-unsaturated carboxylic acid amide that is unsubstituted at the amido nitrogen, which forms the Michael adduct initially by conversion with a polyvalent alcohol having a boiling point of >/=150.degree. C., converts this with a primary or secondary amine with elimination of ammonia to form N-substituted carboxylic acid amide with a protected double bond, the polyvalent alcohol being subsequently eliminated from this product at high temperatures, with formation of the N-substituted .alpha.,.beta.-unsaturated carboxylic acid amide.Type: GrantFiled: January 25, 1985Date of Patent: February 17, 1987Assignee: Chemische Fabrik Stockhausen GmbHInventors: Kurt Dahmen, Erich Kuster, Richard Mertens, Helmut Brehm
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Patent number: 4634558Abstract: .alpha.-Substituted acrylamides of the general formula I ##STR1## where R.sup.1 is a straight-chain, branched or cyclic alkyl radical of not more than 15 carbon atoms which can be unsubstituted or further substituted, are prepared by a process in which the corresponding .alpha.-substituted acrolein oximes are heated at from 40.degree. to 250.degree. C. in the presence of a copper(II) carboxylate and of an unsubstituted or substituted acrylonitrile as cocatalyst.Type: GrantFiled: November 30, 1984Date of Patent: January 6, 1987Assignee: BASF AktiengesellschaftInventors: Franz Merger, Wolfgang Schwarz
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Patent number: 4614827Abstract: A method for isolating a vinyl salt compound in solid form from an aqueous solution thereof by spray drying such an aqueous salt solution.Type: GrantFiled: July 10, 1984Date of Patent: September 30, 1986Assignee: Rohm GmbHInventors: Peter J. Arndt, Franz Wenzel, Manfred Muller, Fritz Schlosser
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Patent number: 4597907Abstract: .alpha.-substituted acrylamides of the general formula I ##STR1## where R.sup.1 is a straight-chain, branched or cyclic alkyl radical of not more than 15 carbon atoms which can be unsubstituted or further substituted, are prepared by a process in which the corresponding .alpha.-substituted acrolein oximes are heated at from 40.degree. to 250.degree. C. in the presence of a copper(II) carboxylate.Type: GrantFiled: December 3, 1984Date of Patent: July 1, 1986Assignee: BASF AktiengesellschaftInventors: Franz Merger, Wolfgang Schwarz
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Patent number: 4596888Abstract: Novel monomers are the reaction products of a vinyl functional monoahl (e.g., hydroxypropyl acrylate) with a halohydroxyalkyl quaternary ammonium compound (e.g., 2-hydroxy-3-chloropropyl ammonium chloride) or a glycidyl trialkyl ammonium compound. Said monomers are highly hydrophilic. Polymers comprising said monomers have a very high affinity for water.Type: GrantFiled: September 1, 1983Date of Patent: June 24, 1986Assignee: The Dow Chemical CompanyInventor: Walter L. Vaughn
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Patent number: 4593123Abstract: Process for the production of acrylamide or methacrylamide wherein acrylonitrile or methacrylonitrile is reacted with water and/or a water donor in the presence of Raney copper catalyst, which is protected from contact with oxygen.Type: GrantFiled: November 28, 1984Date of Patent: June 3, 1986Assignee: Mitsui Toatsu Chemicals, IncorporatedInventor: Fujio Matsuda
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Patent number: 4582933Abstract: This invention describes a process for the production of N-(tert-aminoalkyl)acrylamides by the reaction of acrylic acid with a suitable tertiary aminoalkylamine at a temperature of 150.degree.-230.degree. C. The aminoalkylamine and acrylic acid are reacted in equimolar quantities, preferably in the presence of an acidic or a basic catalyst.Type: GrantFiled: March 17, 1983Date of Patent: April 15, 1986Assignee: Chemische Fabrik Stockhausen GmbHInventors: Richard Mertens, Kurt Dahmen
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Patent number: 4578512Abstract: Novel vinyl ethers are prepared in decarboxylation reactions of novel acid fluoride compounds according to the following reaction: ##STR1## wherein a is 0 or an integer greater than 0;b is 0 or an integer greater than 0;n=1 or an integer greater than 1;R.sub.f and R.sub.f ' are independently selected from the group consisting of F, Cl, perfluoroalkyl or fluorochloroalkyl;X=F, Cl, Br or mixtures thereof when n>1X'=Cl or Br;Y is an acid group or an acid derivative easily convertible to an acid group;Z=F, Cl, Br, OH, NRR' or OA;R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atoms, and aryl; andA=alkali metal, quaternary nitrogen, or R.These vinyl ethers may be homopolymerized with themselves or copolymerized with other vinyl ethers.Type: GrantFiled: February 4, 1982Date of Patent: March 25, 1986Assignee: The Dow Chemical CompanyInventors: Bobby R. Ezzell, William P. Carl, William A. Mod
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Patent number: 4564477Abstract: There are provided polyprenyl compounds of the formula ##STR1## wherein ##STR2## represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z.sup.1 and Z.sup.2 combinedly represent .dbd.O, .dbd.CH--COOH,.dbd.CH--COOR.sup.1, .dbd.CH--CN, .dbd.C(CN)COOR.sup.2, .dbd.CH--CO--NH.sub.2, .dbd.CH--CO--N(R.sup.3) (R.sup.4), .dbd.CH--CO--NHR.sup.5, .dbd.CH--CH.sub.2 --N(R.sup.3) (R.sup.4), .dbd.CH--CH.sub.2 --NHR.sup.5 or .dbd.CH--CHO or Z.sup.1 is a hydrogen atom and Z.sup.2 is --CH.sub.2 COOH, --CH.sub.2 COOR.sup.6, --CH(CN)COOR.sup.2, --CH.sub.2 CN, --CH.sub.2 --CO--NH.sub.2, --CH.dbd.CH--N(R.sup.3) (R.sup.4) or --CH.sub.2 --CH.dbd.N--R.sup.5, R.sup.1, R.sup.2 and R.sup.6 each being a lower alkyl group, R.sup.3 and R.sup.4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R.sup.3 and R.sup.4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R.sup.5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group.Type: GrantFiled: February 17, 1983Date of Patent: January 14, 1986Assignee: Kuraray Co., Ltd.Inventors: Tetsuo Takigawa, Koichi Ibata, Masafumi Okada, Masao Mizuno, Takashi Nishida
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Patent number: 4556736Abstract: A process for producing crystalline acrylamidoalkyltrialkylammonium chloride by reacting a substituted acrylamide with methyl chloride in the presence of a reaction medium from the group consisting of acetone, methyl tert butyl ether and cyclohexane is provided.Type: GrantFiled: July 30, 1984Date of Patent: December 3, 1985Assignee: Deutsch Texaco AktiengesellschaftInventors: Heiko Humbert, Karlheinz Laping
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Patent number: 4544768Abstract: A method comprising contacting a vapor stream resulting from air sparging of aqueous acrylamide containing acrylonitrile with sufficient activated carbon adsorbent to substantially remove acrylamide and acrylonitrile from the vapor stream. This is a particularly advantageous method when aqueous acrylamide is stored in remote locations.Type: GrantFiled: July 25, 1984Date of Patent: October 1, 1985Assignee: The Dow Chemical CompanyInventors: William R. Knee, Sergio S. Cutie
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Patent number: 4536326Abstract: Acrylamide and related monomers are improved by incorporating therein an effective polymerization inhibitor in an amount greater than that which is inherently present in the monomer and a borane, i.e., sodium borohydride.Type: GrantFiled: January 4, 1984Date of Patent: August 20, 1985Assignee: American Cyanamid CompanyInventor: Joseph M. Schmitt
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Patent number: 4492801Abstract: A one-step process for the preparation of N-substituted (meth)acrylamides from the reaction of a (meth)acrylate ester and an amine over a catalytic amount of a metal alkoxide catalyst is described. These catalysts, such as stannous dimethoxide, lead dimethoxide, zinc dimethoxide, copper dimethoxide and bismuth tributoxide give high selectivity to the N-substituted (meth)acrylamides and little selectivity of the Michael adduct propionate ester, which would predominate in the absence of these catalysts. Also, these catalysts are less costly than organo metal catalysts commonly used.Type: GrantFiled: February 28, 1983Date of Patent: January 8, 1985Assignee: Texaco Inc.Inventors: Edward E. McEntire, Kathy B. Sellstrom, Edward C. Y. Nieh, David R. Livingston
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Patent number: 4474806Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.Type: GrantFiled: May 10, 1982Date of Patent: October 2, 1984Assignee: Merck & Co., Inc.Inventors: Thomas R. Beattie, Shu S. Yang
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Patent number: 4444971Abstract: The present invention is directed to a new class of cationic monomers and to polymers thereof. The monomers are quaternary chloromethyl ammonium chlorides having the following general formula:CH.sub.2 .dbd.CR.sub.1 COX(CH.sub.2).sub.n N.sup..sym. R.sub.3 R.sub.4 CH.sub.2 Cl Cl.sup..crclbar. (1)whereR.sub.1 =H, CH.sub.3X=O, NR.sub.2 where R.sub.2 =H, lower alkyln=2-6R.sub.3, R.sub.4 =independently lower alkylThe present invention is also directed to homopolymers and copolymers of the above described class of monomers.Type: GrantFiled: July 25, 1983Date of Patent: April 24, 1984Assignee: Texaco Inc.Inventor: Edward E. McEntire
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Patent number: 4430336Abstract: N-Substituted 2-methylnaphthylamides of the general formula ##STR1## where R.sup.1 is ##STR2## R.sup.3 being hydrogen or alkoxy, or R.sup.1 is ##STR3## R.sup.4 and R.sup.5 being unsubstituted or substituted alkyl, or R.sup.4 and R.sup.5 together forming a heterocyclic ring which contains two oxygen atoms and is unsubstituted or substituted by alkyl or aryl,R.sup.2 is alkyl which is unsubstituted or substituted by halogen, alkoxy, imidazolyl, pyrazolyl or oxo (.dbd.O), or is alkenyl, alkynyl, cycloalkenyl or alkoxy, or substituted or unsubstituted phenyl, or substituted or unsubstituted hetaryl andX is hydrogen, methyl or halogen, fungicides containing these compounds, and processes for the preparation of the compounds.Type: GrantFiled: November 18, 1980Date of Patent: February 7, 1984Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Bernd Zeeh, Ernst-Heinrich Pommer
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Patent number: 4426505Abstract: New polymers are disclosed comprising recurring units of the formula ##STR1## wherein R is hydrogen or lower alkyl containing from 1 to 5 carbon atoms, L is a divalent linking group, and each X is independently chloro or bromo. The polymers are capable of providing a relatively high index of refraction in combination with a relatively high Abbe number and can be utilized as raw materials in the manufacture of plastic optical articles or elements such as lenses or prisms and in the manufacture of optical films and coatings.Type: GrantFiled: February 25, 1982Date of Patent: January 17, 1984Assignee: Polaroid CorporationInventor: Richard A. Minns
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Patent number: 4414159Abstract: Vinyl ether monomers derived from diesters of the formula: ##STR1## wherein R is CH.sub.3 or C.sub.2 H.sub.5 and n is 0 to 10; copolymers of the vinyl ether monomers with one or more selected perfluorinated monoolefins; articles of manufacture made from the copolymers; process for making the diesters; process for using copolymer membranes in a chlor-alkali cell.Type: GrantFiled: December 14, 1981Date of Patent: November 8, 1983Assignee: E. I. Du Pont de Nemours & Co.Inventor: Paul R. Resnick
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Patent number: 4408073Abstract: The invention relates to a process for the preparation of .alpha., .beta.-unsaturated N-substituted carboxylic acid amides, novel .alpha., .beta.-unsaturated N-substituted carboxylic acid amides, a process for the polymerization of these novel .alpha., .beta.-unsaturated N-substituted carboxylic acid amides, including the polymers, and the use of these polymers as sedimentation, flocculating, dewatering and retention aids, as additives for mineral oils, and as ion exchangers.The .alpha., .beta.-unsaturated N-substituted carboxylic acid amides are prepared by transamidation of .beta.-hydroxy or .beta.-alkoxy carboxylic acid amides with primary amines and heating of the N-substituted .beta.-hydroxy or .beta.-alkoxy carboxylic acid amides obtained as intermediate products in the vapor phase in the presence of catalysts. Primary amines are preferably used in the conversion which have no hydrogen beta to the amino group.These .alpha.,.beta.Type: GrantFiled: December 26, 1979Date of Patent: October 4, 1983Assignee: Chemische Fabrik Stockhausen & CieInventors: Bernhard Goossens, Erich Kuster, Kurt Dahmen, Eduard Barthell
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Patent number: 4395311Abstract: Crude aminomethanols are converted to salt form by the addition of a strong acid and subsequently distilled under vacuum. The resulting purified aminomethanol is essentially free of unreacted aldehydes and other volatile impurities.Type: GrantFiled: November 30, 1981Date of Patent: July 26, 1983Assignee: The Dow Chemical CompanyInventor: Charles J. McDonald
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Patent number: 4394493Abstract: Crosslinkable graft copolymers of poly(oxyalkylene) are provided which comprise from about 1 percent by weight of a substituted N-methylol derivative of acrylamide grafted onto a poly(oxyalkylene)-polymer.Type: GrantFiled: September 30, 1981Date of Patent: July 19, 1983Assignee: Union Carbide CorporationInventors: David J. Bartkovitz, George H. Greene
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Patent number: 4387017Abstract: A process for recovering bitumen from oil-in-water (O/W) emulsions is disclosed wherein water soluble demulsifiers are used. These demulsifiers are polymers of diquaternary ammonium monomers containing hydroxyl groups. To resolve the bituminous petroleum emulsions, the process is carried out between 25.degree. and 160.degree. C. wherein the demulsifier of the invention is contacted with the bituminous emulsion.Type: GrantFiled: December 2, 1981Date of Patent: June 7, 1983Assignee: Texaco Inc.Inventors: Edward E. McEntire, David R. McCoy
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4329363Abstract: The present application discloses a method of correcting an imbalance of immune homeostasis caused by cytostatic treatment or radiotherapy by administering to a patient in need of such treatment an effective amount of a novel substituted mercapto acid amide and pharmaceutical compositions containing such novel substituted mercapto acid amides.Type: GrantFiled: January 16, 1980Date of Patent: May 11, 1982Assignee: Merck & Co., Inc.Inventors: Conrad P. Dorn, Howard Jones
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Patent number: 4323704Abstract: Novel compounds of the formula ##STR1## wherein A is methylene, ethylene or ethylidene; R.sub.1 is --C.tbd.CH or --CH.dbd.CH.sub.2 ; R.sub.2 is hydrogen or COR wherein R is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.6 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.a is hydrogen, ##STR3## alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR4## wherein R.sub.7 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl; and R.sub.b has the same meaning as defined for R.sub.a except R.sub.b is not ##STR5## and R.sub.a and R.sub.Type: GrantFiled: January 16, 1981Date of Patent: April 6, 1982Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung, Charles Danzin
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Patent number: 4304937Abstract: A process of preparing a carboxylic acid amide which comprises reacting (a) an aldehyde with (b) at least one compound selected from the group consisting of ammonia, a primary amine and a secondary amine in the presence of a molecular oxygen-containing gas and palladium metal or platinum metal as the catalyst.Type: GrantFiled: November 13, 1979Date of Patent: December 8, 1981Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Nishikido Joji, Tamura Nobuhiro, Fukuoka Yohei
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Patent number: 4302584Abstract: A process for the preparation of 3,3-dimethyl-pent-3-enoic acid amides of the formula I ##STR1## where R.sup.1 and R.sup.2 may be identical or different and each is alkyl of 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together with the nitrogen on which they are present as substituents form a 5-membered or 6-membered saturated ring which may contain a further hetero-atom,wherein an acetamido-acetal or ketene-acetal-aminal is reacted with 3-methyl-but-2-en-1-ol at from 80.degree. to 220.degree. C., in the presence or absence of an inert organic solvent. The products are valuable intermediates for the preparation of insecticidal cyclopropanecarboxylic acid esters.Type: GrantFiled: August 7, 1980Date of Patent: November 24, 1981Assignee: BASF AktiengesellschaftInventor: Klaus Halbritter
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Patent number: 4301083Abstract: Polyoxyalkylene compounds having at least four oxyalkylene units and one or two terminal hydroxyl groups are etherified by reacting same with organic primary chlorides or bromides in the presence of an aqueous, at least 30% by weight solution of sodium or potassium hydroxide to produce the corresponding etherified polyoxyalkylene derivatives. The molar ratio of the organohalide to the hydroxyl group(s) of the polyoxyalkylene compound is at least 1.2, and the molar ratio of the alkali metal hydroxide to such hydroxyl group(s) is at least 1.Type: GrantFiled: January 2, 1980Date of Patent: November 17, 1981Assignee: Kuraray Co., Ltd.Inventors: Noriaki Yoshimura, Masuhiko Tamura
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Patent number: 4297256Abstract: Water-immiscible, acid-soluble N-(aminomethyl)-.alpha.,.beta.-ethylenically unsaturated carboxamides such as N-(diethylaminomethyl)acrylamide are readily prepared by (1) reacting under acidic conditions a carboxamide such as acrylamide with a lower aldehyde such as formaldehyde and a moderately water-soluble secondary amine such as diethylamine and (2) recovering the resulting water-immiscible aminomethyl derivative of carboxamide from the acidic reaction mixture by adjusting the pH of the reaction mixture to a value of 7 or higher, whereby the water-immiscible derivative separates from the reaction mixture.Type: GrantFiled: December 26, 1979Date of Patent: October 27, 1981Assignee: The Dow Chemical CompanyInventor: Charles J. McDonald
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Patent number: 4288390Abstract: N-(aminomethyl)-.alpha.,.beta.-ethylenically unsaturated carboxamides such as N-(dimethylaminomethyl)acrylamide are readily prepared without coincident production of saturated impurities by reacting at a pH below 7 an .alpha.,.beta.-ethylenically unsaturated carboxamide such as acrylamide or N-substituted derivative such as N-methylolacrylamide with a secondary amine such as dimethylamine, and a lower aldehyde such as formaldehyde when such is required. The resulting aminomethyl carboxamides are polymerized at a pH of 7 or less to form polymers containing essentially no gelled product.Type: GrantFiled: June 1, 1979Date of Patent: September 8, 1981Assignee: The Dow Chemical Co.Inventor: Charles J. McDonald
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Patent number: 4265835Abstract: In a process for preparing a N-substituted derivative of a carboxamide, the conversion of carboxamide to the derivative is determined by carbon-13 nuclear magnetic resonance analysis (CMR) wherein the intensities of the carbonyl carbon peaks attributable to the carboxamide and the derivative are measured under conditions of magnetic resonance and the mole ratio of carboxamide to derivative is determined by comparing the intensities of said carbonyl carbon peaks.For example, in the reaction of polyacrylamide with a secondary amine such as dimethylamine and formaldehyde, the conversion of the polyacrylamide to its N-(dimethylaminomethyl) derivative is determined by subjecting the sample to CMR analysis and comparing the intensities of the carbonyl carbon peaks of the polyacrylamide and the N-(dimethylaminomethyl) derivative.Type: GrantFiled: September 10, 1979Date of Patent: May 5, 1981Assignee: The Dow Chemical CompanyInventors: Charles J. McDonald, Robert H. Beaver
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Patent number: 4251461Abstract: A non-catalytic process for the preparation of N-(tertiaryaminoalkyl)acrylamides is disclosed which comprises subjecting a corresponding .beta.-aminopropionamide to a pyrolysis temperature of about 180.degree. to 300.degree. C. after storage of the .beta.-aminopropionamide in an atmospheric holding tank at a temperature of about 150.degree. to 220.degree. C. from eight to seventy-two hours prior to pyrolysis. The corresponding .beta.-aminopropionamide compounds can be prepared by mixing and reacting at least two moles of a tertiaryaminoalkyl amine with an acrylic acid or ester compound. The inventive process provides the production of the N-(tertiaryaminoalkyl)acrylamides in high yields with minimal back addition or polymerization and greatly reduced acid impurity levels.Type: GrantFiled: January 17, 1980Date of Patent: February 17, 1981Assignee: Texaco Development CorporationInventor: David R. Livingston
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Patent number: 4246199Abstract: An improved process for the preparation of N-alkyl-substituted carboxylic acid amides by reaction of a component which forms a carbonium ion with a nitrile, the improvement residing in carrying out the process in the presence of an acid which is inert under distillation conditions and separating the reaction mixture by distillation.Type: GrantFiled: May 30, 1978Date of Patent: January 20, 1981Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Franz-Gerhard Behlau
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Patent number: 4239885Abstract: A process is disclosed whereby acrylonitrile and diacetone alcohol are reacted in at least 93% sulfuric acid to form a novel intermediate reaction product which is recovered as a crystalline solid, washed with an organic solvent to remove colored oily impurities along with sulfuric acid, and hydrolyzed to produce diacetone acrylamide, a reactive monomer useful for preparing polymeric components of photographic films and adhesives. The intermediate reaction product is identified as 5,6-dihydro-6-hydroxy-4,4,6-trimethyl-2-vinyl-1,3(4H)-oxazine sulfate (1:1).Type: GrantFiled: June 28, 1978Date of Patent: December 16, 1980Assignee: American Cyanamid CompanyInventor: Henry Richmond