Carbon To Carbon Unsaturation In Substituent Q Patents (Class 564/204)
  • Patent number: 4705650
    Abstract: 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: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4699965
    Abstract: 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: Grant
    Filed: June 28, 1985
    Date of Patent: October 13, 1987
    Assignee: Eagle Picher Industries, Inc.
    Inventors: Richard A. Markle, Wayne R. Melchior
  • Patent number: 4686302
    Abstract: 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: Grant
    Filed: November 30, 1984
    Date of Patent: August 11, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Wolfgang Schwarz
  • Patent number: 4644083
    Abstract: 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: Grant
    Filed: January 25, 1985
    Date of Patent: February 17, 1987
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Kurt Dahmen, Erich Kuster, Richard Mertens, Helmut Brehm
  • Patent number: 4634558
    Abstract: .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: Grant
    Filed: November 30, 1984
    Date of Patent: January 6, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Wolfgang Schwarz
  • Patent number: 4614827
    Abstract: 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: Grant
    Filed: July 10, 1984
    Date of Patent: September 30, 1986
    Assignee: Rohm GmbH
    Inventors: Peter J. Arndt, Franz Wenzel, Manfred Muller, Fritz Schlosser
  • Patent number: 4597907
    Abstract: .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: Grant
    Filed: December 3, 1984
    Date of Patent: July 1, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Wolfgang Schwarz
  • Patent number: 4596888
    Abstract: 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: Grant
    Filed: September 1, 1983
    Date of Patent: June 24, 1986
    Assignee: The Dow Chemical Company
    Inventor: Walter L. Vaughn
  • Patent number: 4593123
    Abstract: 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: Grant
    Filed: November 28, 1984
    Date of Patent: June 3, 1986
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventor: Fujio Matsuda
  • Patent number: 4582933
    Abstract: 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: Grant
    Filed: March 17, 1983
    Date of Patent: April 15, 1986
    Assignee: Chemische Fabrik Stockhausen GmbH
    Inventors: Richard Mertens, Kurt Dahmen
  • Patent number: 4578512
    Abstract: 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: Grant
    Filed: February 4, 1982
    Date of Patent: March 25, 1986
    Assignee: The Dow Chemical Company
    Inventors: Bobby R. Ezzell, William P. Carl, William A. Mod
  • Patent number: 4564477
    Abstract: 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: Grant
    Filed: February 17, 1983
    Date of Patent: January 14, 1986
    Assignee: Kuraray Co., Ltd.
    Inventors: Tetsuo Takigawa, Koichi Ibata, Masafumi Okada, Masao Mizuno, Takashi Nishida
  • Patent number: 4556736
    Abstract: 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: Grant
    Filed: July 30, 1984
    Date of Patent: December 3, 1985
    Assignee: Deutsch Texaco Aktiengesellschaft
    Inventors: Heiko Humbert, Karlheinz Laping
  • Patent number: 4544768
    Abstract: 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: Grant
    Filed: July 25, 1984
    Date of Patent: October 1, 1985
    Assignee: The Dow Chemical Company
    Inventors: William R. Knee, Sergio S. Cutie
  • Patent number: 4536326
    Abstract: 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: Grant
    Filed: January 4, 1984
    Date of Patent: August 20, 1985
    Assignee: American Cyanamid Company
    Inventor: Joseph M. Schmitt
  • Patent number: 4492801
    Abstract: 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: Grant
    Filed: February 28, 1983
    Date of Patent: January 8, 1985
    Assignee: Texaco Inc.
    Inventors: Edward E. McEntire, Kathy B. Sellstrom, Edward C. Y. Nieh, David R. Livingston
  • Patent number: 4474806
    Abstract: 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: Grant
    Filed: May 10, 1982
    Date of Patent: October 2, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Beattie, Shu S. Yang
  • Patent number: 4444971
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: April 24, 1984
    Assignee: Texaco Inc.
    Inventor: Edward E. McEntire
  • Patent number: 4430336
    Abstract: 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: Grant
    Filed: November 18, 1980
    Date of Patent: February 7, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Bernd Zeeh, Ernst-Heinrich Pommer
  • Patent number: 4426505
    Abstract: 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: Grant
    Filed: February 25, 1982
    Date of Patent: January 17, 1984
    Assignee: Polaroid Corporation
    Inventor: Richard A. Minns
  • Patent number: 4414159
    Abstract: 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: Grant
    Filed: December 14, 1981
    Date of Patent: November 8, 1983
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventor: Paul R. Resnick
  • Patent number: 4408073
    Abstract: 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: Grant
    Filed: December 26, 1979
    Date of Patent: October 4, 1983
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Bernhard Goossens, Erich Kuster, Kurt Dahmen, Eduard Barthell
  • Patent number: 4395311
    Abstract: 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: Grant
    Filed: November 30, 1981
    Date of Patent: July 26, 1983
    Assignee: The Dow Chemical Company
    Inventor: Charles J. McDonald
  • Patent number: 4394493
    Abstract: 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: Grant
    Filed: September 30, 1981
    Date of Patent: July 19, 1983
    Assignee: Union Carbide Corporation
    Inventors: David J. Bartkovitz, George H. Greene
  • Patent number: 4387017
    Abstract: 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: Grant
    Filed: December 2, 1981
    Date of Patent: June 7, 1983
    Assignee: Texaco Inc.
    Inventors: Edward E. McEntire, David R. McCoy
  • Patent number: 4370497
    Abstract: 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: Grant
    Filed: August 7, 1980
    Date of Patent: January 25, 1983
    Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
  • Patent number: 4329363
    Abstract: 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: Grant
    Filed: January 16, 1980
    Date of Patent: May 11, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Conrad P. Dorn, Howard Jones
  • Patent number: 4323704
    Abstract: 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: Grant
    Filed: January 16, 1981
    Date of Patent: April 6, 1982
    Assignee: Merrell Toraude et Compagnie
    Inventors: Brian W. Metcalf, Michel Jung, Charles Danzin
  • Patent number: 4304937
    Abstract: 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: Grant
    Filed: November 13, 1979
    Date of Patent: December 8, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nishikido Joji, Tamura Nobuhiro, Fukuoka Yohei
  • Patent number: 4302584
    Abstract: 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: Grant
    Filed: August 7, 1980
    Date of Patent: November 24, 1981
    Assignee: BASF Aktiengesellschaft
    Inventor: Klaus Halbritter
  • Patent number: 4301083
    Abstract: 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: Grant
    Filed: January 2, 1980
    Date of Patent: November 17, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Noriaki Yoshimura, Masuhiko Tamura
  • Patent number: 4297256
    Abstract: 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: Grant
    Filed: December 26, 1979
    Date of Patent: October 27, 1981
    Assignee: The Dow Chemical Company
    Inventor: Charles J. McDonald
  • Patent number: 4288390
    Abstract: 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: Grant
    Filed: June 1, 1979
    Date of Patent: September 8, 1981
    Assignee: The Dow Chemical Co.
    Inventor: Charles J. McDonald
  • Patent number: 4265835
    Abstract: 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: Grant
    Filed: September 10, 1979
    Date of Patent: May 5, 1981
    Assignee: The Dow Chemical Company
    Inventors: Charles J. McDonald, Robert H. Beaver
  • Patent number: 4251461
    Abstract: 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: Grant
    Filed: January 17, 1980
    Date of Patent: February 17, 1981
    Assignee: Texaco Development Corporation
    Inventor: David R. Livingston
  • Patent number: 4246199
    Abstract: 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: Grant
    Filed: May 30, 1978
    Date of Patent: January 20, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Arlt, Franz-Gerhard Behlau
  • Patent number: 4239885
    Abstract: 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: Grant
    Filed: June 28, 1978
    Date of Patent: December 16, 1980
    Assignee: American Cyanamid Company
    Inventor: Henry Richmond