Material Contains Aldehyde Or Ketone Or Polymeric Reaction Product Thereof, E.g., Urea-formaldehyde, Etc. Patents (Class 526/208)
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Patent number: 5300600Abstract: Disclosed are high concentration aqueous dispersions of normally solid organic peroxides using a dispersion agent comprising an alkylaryl polyether alcohol and an oxyalkylated phenolic resin. Optional components such as thickening agents, anionic emulsifiers and a partial ester of a carboxylic acid copolymer may also be included. Dispersions having concentrations of up to about 65% weight percent organic peroxide can be prepared. Dispersions having concentrations of up to about 40 weight percent organic peroxide are sprayable. Also disclosed are the curing of polyester resins and the suspension polymerization of vinyl monomers using these dispersions.Type: GrantFiled: May 7, 1992Date of Patent: April 5, 1994Assignee: Witco CorporationInventors: Lawrence A. Bock, Ronald L. Pastorino, Douglas Nordhaus
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Patent number: 5296575Abstract: Improved monodisperse spheroidal particle latices of vinyl chloride polymers, e.g., having particle sizes ranging from 0.17 to 0.8 .mu.m or from 0.5 to 1.2 .mu.m, are produced by aqueous emulsion polymerization of vinyl chloride monomer, whether in a single stage or in two stages, in the absence of surface-active agent, in the presence of at least 0.2% by weight of at least one water-soluble alkali metal or ammonium persulfate initiator, and also in the presence of at least one water-soluble auxiliary compound that is a solvent for vinyl chloride, in such amount that the solubility of vinyl chloride in the aqueous phase at 25.degree. C. at atmospheric pressure is at least 1.5 g/l.Type: GrantFiled: September 26, 1991Date of Patent: March 22, 1994Assignee: AtochemInventors: Jacques Grossoleil, Patrick Kappler, Nicolas Krantz
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Patent number: 5288794Abstract: A cyanoacrylate monomer adhesive formulation which has improved thermal properties resulting from the inclusion in the formulation of an effective amount for enhancing the thermal resistance of the cured polymer of a mono, poly or hetero aromatic compound characterized by at least three substitutions on an aromatic ring thereof, two or more of said substitutions being electron withdrawing groups selected from the group consisting of NO.sub.2, CN, CF.sub.3, NR.sup.1.sub.3.sup.+, SR.sup.1.sub.2.sup.+, C(.dbd.O)R.sup.1, C(.dbd.O)OR.sup.1, NO, CCl.sub.3, SO.sub.2, S(.dbd.O), SO.sub.3, SO.sub.2 R.sup.1, SO.sub.2 OR.sup.1 and F, one or more of said substitutions being leaving groups selected from the group consisting of F, Br, Cl, I, NO.sub.2, CN, SOR.sup.1, SO.sub.2 R.sup.1 and SO.sub.2 OR.sup.1, and R.sup.1 is an optionally substituted hydrocarbon group. Example such compounds have the formula: ##STR1## where L is the leaving group and the W groups are the electron withdrawing groups.Type: GrantFiled: October 23, 1992Date of Patent: February 22, 1994Assignee: Loctite CorporationInventor: Shabbir Attarwala
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Patent number: 5286821Abstract: A two-part initiator system useful in acrylic adhesive compositions comprising in one part a stable organoboron amine complex and in the second part an aldehyde destabilizer or activator. This initiator is particularly useful in elastomeric acrylic adhesive compositions and provides room temperature, relatively slow curing systems with good adhesive properties making them useful in applications where longer open times are required.Type: GrantFiled: March 17, 1992Date of Patent: February 15, 1994Assignee: National Starch and Chemical Investment Holding CorporationInventor: Martin M. Skoultchi
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Patent number: 5277739Abstract: Adhesive component formulations containing (meth)acrylic acid esters, containing formamide groups, and optionally an initiator, which are used as an adhesive component for the treatment of collagen-containing materials.Type: GrantFiled: December 15, 1992Date of Patent: January 11, 1994Assignee: Bayer AktiengesellschaftInventors: Michael Muller, Wolfgang Podszun, Bernd Alker
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Patent number: 5278266Abstract: Poly(vinyl phosphonic acid) is synthesized by polymerizing vinyl phosphonyl dichloride in the presence of a cross-linker such as formaldehyde or 1,3-butadiene di-epoxide, with a free-radical initiator. The product can be reacted with aluminosilicate glass to form an improved cement.Type: GrantFiled: February 5, 1992Date of Patent: January 11, 1994Assignee: British Technology Group LimitedInventors: Julian H. Braybrook, John Ellis
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Patent number: 5270396Abstract: A method for preparing resinous copolymers by sequential charge copolymerization of at least two charges, at least one being a conjugated diene and at least one being a monovinylarene; followed by a charge of a polyfunctional coupling agent; and the final charge being an essentially difunctional coupling agent. The copolymer made by this method and articles made from this copolymer are also provided.Type: GrantFiled: May 18, 1992Date of Patent: December 14, 1993Assignee: Phillips Petroleum CompanyInventors: Ralph C. Farrar, Jr., George A. Moczygemba, William J. Trepka
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Patent number: 5254649Abstract: This invention relates to a process for producing a polymer predominating in terminal unsaturation by cationically polymerising a 1-olefin in the liquid phase at a temperature from -100.degree. to +100.degree. C. in the presence of a catalyst composition comprising tin tetrachloride and a co-catalyst which is a source of cations and which is substantially free of organometallic compounds. The process is particularly suited to producing polybutenes having high vinylidene content which have high reactivity, especially towards forming maleic anhydride adducts.Type: GrantFiled: November 28, 1990Date of Patent: October 19, 1993Assignee: BP Chemicals LimitedInventors: Colin D. Miln, Douglas Stewart
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Patent number: 5247033Abstract: A polymerization method carried out in the presence of unsaturated hydroperoxides useful as molecular weight regulators, is disclosed. Also disclosed are polymers and oligomers made by this process and articles of manufacture comprising one or more polymers or oligomers made by this process. These molecular weight regulating hydroperoxides provide the ability to introduce an epoxy functionality to the oligomer or polymer as well as an additional functionality and a primary hydroxy group. Further, omega substituted or alpha, omega disubstituted polymers may be synthesized using the unsaturated hydroperoxides of the present invention.Type: GrantFiled: April 28, 1992Date of Patent: September 21, 1993Assignee: Akzo N.V.Inventors: Luc L. T. Vertommen, John Meijer
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Patent number: 5204428Abstract: A copolymer of the present invention is produced by copolymerization of an electron-donating monomer having an electron-accepting group and an electron-accepting monomer having an electron-accepting group. The copolymer thus exhibits a high dielectric constant, a low level of hygroscopicity and good adhesion.Type: GrantFiled: December 16, 1991Date of Patent: April 20, 1993Assignees: Alps Electric Co., Ltd., Shiro KobayashiInventors: Shiro Kobayashi, Yoshihiro Taguchi, Hiroshi Uyama
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Patent number: 5183831Abstract: The present invention relates to a radiation curable composition with high temperature oil resistance comprising(1) a(meth)acrylated urethane component comprising(a) the reaction product of hydroxyethyl(meth)acrylate and a monomeric or polymeric aromatic isocyanate,(b) hydroxyethyl(meth)acrylate, and optionally(c) a(meth)acylated prepolymer of a monomeric of polymeric aromatic isocyanate and at least one polycaprolactone polyol with a functionality.gtoreq.2 and a molecular weight in the range of about 500 to about 3,000 or (d) a(meth)acrylated prepolymer of a monomeric or polymeric aromatic isocyanate and at least one polyether polyol with a functionality.gtoreq.2 and a molecular weight in the range of about 90 to about 7,000, or a mixture of (c) and (d);(2) an aromatic multifunctional epoxy (meth)acrylate having a molecular weight of less than about 1000;(3) at least one free radical polymerizable monomer; and(4) a free radical photoinitiator,which composition exhibits at 25.degree. C.Type: GrantFiled: August 22, 1991Date of Patent: February 2, 1993Assignee: Ciba-Geigy CorporationInventors: Richard A. Bielat, Kieran F. Drain
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Patent number: 5180756Abstract: Agents which are curable by ultraviolet radiation are based on a binder formulation of (1) from 99.0 to 20% by weight of a copolymer, (2) from 1.0 to 80% by weight of monoolefinically unsaturated compounds and (3) from 0.0 to 20% by weight of polyolefinically unsaturated compounds. The agents contain copolymers (1) which are obtainable by subjecting a mixture of (A) from 80 to 99.9% by weight of olefinically unsaturated monomers, (B) from 0 to 10% by weight of a copolymerizable olefinically unsaturated photoinitiator and (C) from 0 to 10% by weight of a polymerization-regulating photoinitiator to free radical polymerization, the sum of (B) and (C) being not less than 0.1% by weight and the stated percentages by weight being based on the sum of the weights of (A)+(B)+(C).Type: GrantFiled: April 6, 1990Date of Patent: January 19, 1993Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher
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Patent number: 5173551Abstract: A free-radical retrograde polymerization process for forming a polymer. An admixture of reactants including predetermined amounts of a monomer, a solvent, and a free-radical-initiator is reacted. A precipitation polymerization reaction occurs such that a polymer-rich phase is at a temperature generally above the lower critical solution temperature (LCST) of the admixture.Type: GrantFiled: March 9, 1990Date of Patent: December 22, 1992Assignee: Board of Control of Michigan Technological UniversityInventor: Gerard T. Caneba
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Patent number: 5169914Abstract: A method for producing polymers with narrow molecular weight distribution which involves combining (1) an initiator component of the formula ##STR1## in which R.sub.1, R.sub.2, and R.sub.3 are alkyl, aryl, or aralkyl groups, and can be the same or different, and X is an acetate, etherate, a hydroxyl group, or a halogen, and i is a positive whole number, (2) a Lewis acid of the formula MX.sub.n in which M is titanium, aluminum, boron, or tin, X is a halogen, and n is a positive whole number, (3) an electron donor component having an electron donor number of from at least about 25 to no more than about 50, (4) a solvent for the preceding and (5) a hydrocarbon monomer component.Type: GrantFiled: April 1, 1992Date of Patent: December 8, 1992Assignee: Edison Polymer Innovation CorporationInventors: Gabor Kaszas, Judit E. Puskas, Joseph P. Kennedy
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Patent number: 5145923Abstract: For the preparation of copolymers of ethylene, ethylene is polymerized with esters of vinyl alcohol in the absence of solvents and emulsifiers and in the presence of free radical acceptors. The addition of free radical acceptors makes it possible to increase the polymerization temperature in comparison to a procedure without the use of free radical acceptors.Type: GrantFiled: June 18, 1991Date of Patent: September 8, 1992Assignee: Hoechst AktiengesellschaftInventors: John V. Hobes, Wolfgang Payer, Werner Reimann
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Patent number: 5132345Abstract: An ion-selective polymeric membrane for an electrochemical sensor for use in analytical chemistry, comprisinga) a supporting matrix e.g. of PVC, andb) an ionophore selected from calixarene or oxacalixarene derivatives of the formula IV ##STR1## wherein n+m=3-8;m=0-8;n=0-8;a, which may be the same or different on each aryl group, is 0 or 1;R.sup.2 is alkyl, aryl, alkaryl, alkoxy, alkoxyalkoxy, aryloxy, alkaryloxy, alicyclic, alkylthio, arylthio, alkarylthio, or a substituted derivative thereof;R.sup.3 is --H, alkyl or alkenyl;X is --OH or a group containing an acrylate or methacrylate functional group;provided that when X is --OH, n is at least 1/2(n+m);and provided that when m=0, n=4, a=0 and R.sup.3 is alkyl or allyl, R.sup.2 is not alkoxy having 4 or more carbon atoms in the alkyl group;and provided that when m=0, n=4, a=0 and R.sup.3 is t-butyl, R.sup.2 is not methoxy or ethoxy;or of the formula V ##STR2## wherein R.sup.Type: GrantFiled: December 10, 1990Date of Patent: July 21, 1992Inventors: Stephen J. Harris, Michael A. McKervey, Gyula Svehla, Dermot Diamond
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Patent number: 5100978Abstract: Polyethylene and copolymers of predominant amounts of ethylene and minor amounts of comonomers which are polymerizable with ethylene are obtainable by free radical polymerization of the monomers under from 1,500 to 5,000 bar and at from 40.degree. to 250.degree. C. by means of an initiator with virtually complete exclusion of oxygen in not less than n=3 polymerization stages, by a method in which, in the first stage, the total amount of the predominant part of the monomers are subjected to polymerization using some of the initiator required, until said polymerization comes virtually to a stop, thereafter a further part of the initiator and, if required, of the monomers are added to the mixture, which has been cooled by 20.degree.-60.degree. C., and this process is repeated in the subsequent stages until the n th stage, with the proviso that the initiators used in the (n-1) th stage have a half-life temperature of from 80.degree. to 160.degree. C.Type: GrantFiled: April 12, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Norbert Hasenbein, Wolfgang Ball, Juergen Schmidt-Theummes, Gernot Koehler
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Patent number: 5086137Abstract: A process in which selected vinyl monomers, such as acrylic esters and acids, and chloroprene are polymerized by contacting them with an aryl diazotate or a metal cyanate in the presence of certain halogenated organic compounds. The process is especially useful for preparing block copolymers.Type: GrantFiled: August 6, 1990Date of Patent: February 4, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Joe D. Druliner, Michael Fryd
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Patent number: 5073611Abstract: Copolymers which are curable by ultraviolet radiation in the air are prepared by a process in which a mixture of (A) from 80 to 99.9% by weight of olefinically unsaturated monomers, (B) from 0 to 10% by weight of a copolymerizable olefinically unsaturated, photoreactive compound which, in the excited state produced by UV radiation, is capable of abstracting hydrogen and (C) from 0 to 10% by weight of a polymerization-regulating photoreactive compound which, in the excited state, is capable of abstracting hydrogen is subjected to free radical polymerization, the sum of (B) and (C) being not less than 0.1% by weight and the stated percentages by weight being based on the sum of the weights of (A)+(B)+(C).Type: GrantFiled: April 29, 1991Date of Patent: December 17, 1991Assignee: BASF AktiengesellschaftInventors: Gerd Rehmer, Andreas Boettcher
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Patent number: 5059662Abstract: A method for producing ethylene copolymer using ethylene and at least a comonomer of unsaturated glycidyl monomer in the presence of a polymerization initiator, wherein the undesirable thermal polymerization of the unsaturated glycidyl monomer in the preparation system can be avoided and the operation can be continued for a long period of time in a stable condition. The method is characterized in that at least two kinds of polymerization inhibitors are used and the inhibition factor of one polymerization inhibitor added to the unsaturated glycidyl monomer is smaller than that of another polymerization inhibitor added to the lubricating oil for compressors and the unsaturated glycidyl monomer containing 100 to 2000 ppm of a polymerization inhibitor is introduced from the inlet side of a high pressure compressor into the reaction system and the lubricating oil containing 0.1 to 10% by weight of a polymerization inhibitor is used for the high pressure compressor.Type: GrantFiled: February 26, 1990Date of Patent: October 22, 1991Assignees: Resene Products Company, Nippon Petrochemicals Co. Ltd.Inventors: Karl W. Wikelski, Shinji Kojima
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Patent number: 5051485Abstract: The present invention provides a method for the polymerization or copolymerization of a monomer or blend of monomers selected from the group consisting of C-10 terpenes, vinyl aromatics and C-5 dienes that comprises complexing a Lewis acid with an organic ketone to produce a catalyst complex. The monomer or blend of monomers is added to the catalyst complex producing the reaction mixture. The reaction mixture is maintained at a temperature of between 10.degree. C. and 60.degree. C. and, when the reaction is complete, is quenched with water. The polymerized or copolymerized resin is then recovered.Type: GrantFiled: December 18, 1989Date of Patent: September 24, 1991Assignee: Arizona Chemical CompanyInventors: John J. Schmid, James W. Booth
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Patent number: 5037904Abstract: A method of preventing polymer scale deposition in a polymerization vessel during polymerization of a monomer having an ethylenically double bond, wherein said polymerization is carried out in a polymerization vessel of which the inner wall has a coating comprising a reaction product of a tannin and an aldehyde; a scale preventive agent comprising said reaction product; and a polymerization vessel having said coating on the inner wall thereof. Polymer scale deposition on the inner wall, etc. of the polymerization vessel can be effectively prevented.Type: GrantFiled: February 1, 1990Date of Patent: August 6, 1991Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Susumu Ueno, Ichiro Kaneko, Mikio Watanabe
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Patent number: 5003016Abstract: Activator compositions for redox-initiated cure of adhesive compositions of ethylenically-unsaturated monomers which comprise the condensation reaction product of an alpha-hydroxy ketone, e.g., benzoin, and a primary amine, and preferably a transition metal salt. Also two-part adhesive compositions comprising such activator compositions and a process for bonding two or more adherends with such activator compositions.Type: GrantFiled: January 17, 1989Date of Patent: March 26, 1991Assignee: Minnesota Mining and Manufacturing CompanyInventor: Charles W. Boeder
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Patent number: 4996274Abstract: Polymer and process of polymerizing a monomer charge containing at least 85% of an olefinically unsaturated carboxyl monomer of 3 to 5 carbon atoms at up to 15% of a copolymerizable comonomer, in the presence of a mixed reaction medium containing an organic solvent and a hydrocarbon solvent in respective weight ratio of 95/5 to 1/99, said organic solvent is selected from ketones, esters, ethers, and alcohols having solubility parameter in the range of 8 to 15 and said hydrocarbon solvent is selected from aliphatic and cyclic aliphatic alkanes containing 4 to 12 carbon atoms and non-benzene aromatics of 7 to 9 carbon atoms. Said organic solvent and said hydrocarbon solvent are preferably liquid at room temperature. Viscosity of the 0.2% by weight polymer is in excess of 15,000 cps, preferably in excess of 20,000 cps, and its clarity is at least 80%, preferably 85% transmittance. Viscosity of 1% mucilages containing 1% sodium chloride salt is greater than 5,000 cps, preferably greater than 8,000 cps.Type: GrantFiled: February 19, 1988Date of Patent: February 26, 1991Assignee: The B. F. Goodrich CompanyInventor: Chin C. Hsu
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Patent number: 4990581Abstract: The present invention relates to a compound that can be reacted with a polymer resin to form the conductive polymer. More particularly, the present invention relates to a tetraalkylammonium acrylate that can be reacted with a convention acrylic resin to form a stable, conductive polymer that will conduct electricity but is impermeable to liquids.The tetraalkylammonium acrylate has the following general structure: ##STR1## wherein: R.sub.1, R.sub.2 R.sub.3, and R.sub.4 are alkyl groups of from 3 to 18 carbon atoms; andR.sub.5 is a hydrogen or an alkyl group of from 1 to 3 carbon atoms.The conductive polymer of the present invention is suitable for use as the electricity conducting barrier in reference electrodes.Type: GrantFiled: March 10, 1988Date of Patent: February 5, 1991Assignee: Skeptikos Technology, Inc.Inventor: Albert D. Poulin
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Patent number: 4988781Abstract: A homogeneous, random interpolymer of ethylene and an alpha-olefinically unsaturated carboxylic acid or ester having a melt flow rate in the range of about 0.1 to about 300 g/10 minutes, as determined by ASTM D-1238 (190.degree. C./2160 g), is improved during its manufacture when made in a substantially constant environment in a stirred autoclave under substantially steady-state conditions of temperature, pressure, and flow rates, said temperature and pressure being sufficient to produce a single phase reaction, using a free-radical initiator, said improvement being obtained by the use of a minor amount of a telogenic modifier in the reaction mixture, the process being further characterized by the use of either, or both, of (a) a temperature which is lower than that which would be required without the presence of the telogen, or (b) a pressure which is higher than that which would be required without the presence of the modifier.Type: GrantFiled: February 27, 1989Date of Patent: January 29, 1991Assignee: The Dow Chemical CompanyInventors: Osborne K. McKinney, David A. Eversdyk, Michael E. Rowland
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Patent number: 4985517Abstract: According to one aspect of the present invention, improved acrylic copolymer resins are provided which are formed by co-polymerization of a monomer mixture comprising hydroxy-substituted alkyl (meth)acrylates, alkyl methacrylates or vinyl aromatics, and higher alpha-olefins. The invention provides improved low molecular weight acrylic resins useful as components in high solids acrylic coatings suitable for electrostatic spraying.Type: GrantFiled: June 2, 1989Date of Patent: January 15, 1991Assignee: Exxon Chemical Patents, Inc.Inventors: Albert I. Yezrielev, Michael G. Romanelli, William E. Wellman
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Patent number: 4948848Abstract: What is described herein is a solution feed, slurry precipitation polymerization process for making copolymers of maleic anhydride and an alkyl vinyl ether within a predetermined viscosity range.The process of the invention is characterized by precharging a large excess of the alkyl vinyl ether in a reactor, feeding maleic anhydride dissolved in a minimum amount of an organic solvent into the precharged reactor, and polymerizing the monomers in the presence of a free radical initiator. The copolymer product then appears as a pumpable slurry in the reaction medium. The slurry is discharged from the reactor and the desired copolymer is obtained therefrom as a fine, white powder having specific viscosities in the range of about 1.5-6.0, and preferably about 2.6-3.5.Type: GrantFiled: April 7, 1989Date of Patent: August 14, 1990Assignee: GAF Chemicals CorporationInventors: Mohammed Tazi, Nikhil Kundel
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Patent number: 4933407Abstract: Oxacalixarenes of general formula I: ##STR1## wherein m=0-7 and n=1-8 with the proviso that m+n.ltoreq.8;R is hydrogen, halogen, or hydrocarbyl, aryl, hydrocarbylaryl or a substituted derivative thereof, and R may be the same or different on each aryl group; andR' is hydrocarbyl, aryl, hydrocarbylaryl, hydrocarbyloxy, aryloxy or hydrocarbylaryloxy or a substituted derivative thereof.The invention also provides a method of preparing oxacalixarenes of formula I, and cyanoacrylate adhesive compositions including as accelerator an oxacalixarene of formula I.Type: GrantFiled: July 21, 1989Date of Patent: June 12, 1990Assignee: Loctite (Ireland) Ltd.Inventors: Stephen J. Harris, Maureen G. MacManus
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Patent number: 4925905Abstract: Water-soluble copolymers having a K value of from 8 to 100 (determined on the Na salt of the copolymers according to H. Fikentscher in aqueous solution at 25.degree. C., at a pH of 7 and at a concentration of the Na salt of the polymer of 1% by weight) are prepared by copolymerization of monomer mixtures of(a) from 98.5 to 18.5 mol % of one or more monoethylenically unsaturated C.sub.3 -C.sub.6 -monocarboxylic acids,(b) from 1.5 to 20 mol % of one or more comonomers which contain two or more ethylenically unsaturated, nonconjugated double bonds which are separated from one another by one or more ester bonds,(c) from 0 to 80 mol % of one or more monoethylenically unsaturated C.sub.4 -C.sub.Type: GrantFiled: March 30, 1989Date of Patent: May 15, 1990Assignee: BASF AktiengesellschaftInventors: Dieter Boeckh, Hans-Peter Seelmann-Eggebert, Heinrich Hartmann, Wolfgang Trieselt, Richard Baur
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Patent number: 4923940Abstract: Polymer and process of polymerizing a monomer charge containing at least 85% of an olefinically unsaturated carboxyl monomer of 3 to 5 carbon atoms at up to 15% of a copolymerizable comonomer, in the presence of a mixed reaction medium containing an organic solvent and a hydrocarbon solvent in respective weight ratio of 95/5 to 1/99, said organic solvent is selected from ketones, esters, ethers, and alcohols having solubility parameter in the range of 8 to 15 and said hydrocarbon solvent is selected from aliphatic and cyclic aliphatic alkanes containing 4 to 12 carbon atoms and non-benzene aromatics of 7 to 9 carbon atoms. Said organic solvent and said hydrocarbon solvent are preferably liquid at room temperature. Viscosity of the 0.2% by weight polymer is in excess of 15,000 cps, preferably in excess of 20,000 cps, and its clarity is at least 80%, preferably 85% transmittance. Viscosity of 1% mucilages containing 1% sodium chloride salt is greater than 5,000 cps, preferably greater than 8,000 cps.Type: GrantFiled: March 16, 1989Date of Patent: May 8, 1990Assignee: The B.F. Goodrich CompanyInventor: Chin C. Hsu
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Patent number: 4912183Abstract: A free radical polymerization process comprises bringing together(a) a monomeric material such as an acrylic monomer in a relatively low polarity medium(b) a free radical source or initiator such as a metallic salt initiator or activator normally soluble only in high polarity media such as water and(c) a calixarene derivative of the formula I: ##STR1## wherein m+n=4, 6 or 8 n=an integer greater than or equal to 1/2 (m+n)wherein m+n=4,6 or 8n=an integer greater than or equal to 1/2 (m+n)R=hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyl, substituted hydrocarbyloxy, aryl, hydrocarbylaryl, aryloxy, hydrocarbylaryloxy, substituted aryl, substituted hydrocarbylaryl, substituted aryloxy, or substituted hydrocarbylaryloxy;R'=H, hydrocarbyl, aryl, hydrocarbylaryl, substituted hydrocarbyl, substituted aryl, or substituted hydrocarbylaryl;R"=H, hydrocarbyl or substituted hydrocarbyl.Type: GrantFiled: April 6, 1988Date of Patent: March 27, 1990Assignee: Loctite (Ireland) Ltd.Inventors: Brendan Kneafsey, John M. Rooney, Stephen J. Harris
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Patent number: 4895907Abstract: An improved free radical polymerization process employing as a polymerization initiator a bisquinone peroxide. Upon decomposition to initiate polymerization such bisquinone peroxides may also produce singlet oxygen capable of producing hydroperoxidized rubber if rubber is included in the polymerization mixture. The by-products formed from the decomposition of the bisquinone peroxide desirably comprise hindered phenolic compounds having antioxidant properties.Type: GrantFiled: August 15, 1988Date of Patent: January 23, 1990Assignee: The Dow Chemical CompanyInventors: Duane B. Priddy, Mehmet Demirors
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Patent number: 4859751Abstract: A novel process for the preparation of a readily dispersible, pourable dispersion powder comprising emulsion polymerizing in the presence of a free radial initiator a mixture of 1 to 50% by weight of ethylene and 99 to 50% by weight of an ethylenically unsaturated comonomer phase comprising at least one member of the group consisting of (a) 60 to 100% by weight of vinyl chloride, (b) 0 to 40% by weight of monoethylically unsaturated, oil-soluble monomers, (c) 0 to 10% by weight of monoethylenically unsaturated water-soluble monomers having functional groups and (d) 0 to 5% by weight of oil-soluble monomers that are monoethylenically unsaturated and have functional groups or are multiple ethylenically unsaturated and optionally a protective colloid and/or emulsifier at an ethylene pressure of 10 to 150 bar to obtain an aqueous dispersion of a vinyl chloride-ethyelene copolymer, optionally adding to the aqueous dispersion (e) 0 to 40% by weight, based on the VCE-polymer, of at least one water-soluble substanceType: GrantFiled: October 29, 1984Date of Patent: August 22, 1989Assignee: Wacker-Chemie GmbHInventors: Joachim Schulze, Klaus Adler, Manfred Selig, Peter Ball, Klaus Marquardt, Otmar Killermann, Manfred Hannebaum
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Patent number: 4849489Abstract: A continuous process and system for producing a polymer comprising maleic anhydride and alpha-olefin monomeric units is disclosed. The process comprises combining monomeric reactants comprising the maleic anhydride and the alpha-olefin, in the presence of a minimal effective amount of a solvent, to produce a polymerizable reaction mixture. The solvent is present in minimal amounts, namely, at about 2 to about 9 weight percent, based upon the weight of the reaction mixture. The polymerizable reaction mixture is heated; and at least one thermally-decomposable initiator is added to the thus-heated, polymerizable reaction mixture to initiate the polymerization reaction. The presence of the initiator causes the maleic anhydride and the alpha-olefin to polymerize, thereby producing the desired polymer.Type: GrantFiled: August 11, 1987Date of Patent: July 18, 1989Assignee: S. C. Johnson & Son, Inc.Inventors: Franck E. Benhamou, Kenneth R. Lukow, Calvin J. Verbrugge
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Patent number: 4833221Abstract: A two step method for making a thermoplastic molding composition predominantly comprising methyl methacrylate by polymerizing monomers in a first stage, in the presence or absence of a solvent, to 50 percent conversion, further polymerizing at 75.degree. C. to 150.degree. C. in a second stage in the presence of a nonpolymerizable organic solvent to a conversion of at least 80 percent, and then evaporating volatile constituents.Type: GrantFiled: September 2, 1987Date of Patent: May 23, 1989Assignee: Rohm GmbHInventor: Klaus Albrecht
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Patent number: 4795780Abstract: Process for the preparation of thermoplastic copolymers of .alpha.-methylstyrene and acrylonitrile by continuous bulk copolymerization ofA. 30 to 50 mol % of .alpha.-methylstyrene andB. 70 to 50 mol % of acrylonitrileat temperatures from 60.degree. to 120.degree. C. with average residence times of 4 to 12 hours in the presence of initiators which supply free radicals, carried out in at least two continuously operated mixed tank reactors, characterized in that 100 molar parts of a monomer mixture ofA.sub.0. 34 to 52 mol % of .alpha.-methylstyrene andB.sub.0. 66 to 48 mol % of acrylonitrileare fed continuously into the first tank reactor per unit time, and, with back-mixing, are copolymerized up to a conversion of 5 to 30 molar parts to give a copolymer of the compositionA.sub.1. 49 to 53 mol % of .alpha.-methylstyrene andB.sub.1. 51 to 47 mol % of acrylonitrile,and the mixture consisting of 70 to 95 molar parts of the monomers A and B and 5 to 30 molar parts of the copolymer of the composition A.sub.1 -B.sub.Type: GrantFiled: July 20, 1987Date of Patent: January 3, 1989Assignee: Bayer AktiengesellschaftInventors: Frank Wingler, Klaus Summermann, Gerd Wassmuth, Alfred Pischtschan, Joachim Doring
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Patent number: 4780526Abstract: Polymeric cyclopentadiene derivatives, method for preparing polymeric cyclopentadiene derivatives, and use of polymeric cyclopentadiene derivatives in curable binder compositions.Type: GrantFiled: October 14, 1986Date of Patent: October 25, 1988Assignee: Ashland Oil, Inc.Inventors: Bruce A. Gruber, Heimo J. Langer, William R. Dunnayant
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Patent number: 4777230Abstract: A process is provided for the free radical polymerization of monomers derived from substituted or unsubstituted acrylic acid/methacrylic acid and esters thereof for the production of a polymer having a narrow molecular weight distribution and an average molecular weight of less than 4000. These polymers are produced by the solution polymerizing of said monomers wherein 20-40% by weight of the monomer composition is hydroxyalkyl acrylate or methacrylate in the presence of a solvent system suitable for high solids coating applications and in the presence of an initiating amount of a tertiary alkyl hydroperoxide and/or its derivatives having at least 5 carbons wherein the initiator and monomers, alone or in combination, are added continuously at a programmed rate wherein the rate of addition corresponds approximately to the rate of decomposition of said monomer and initiator. These polymers are used for high solids coating applications.Type: GrantFiled: December 12, 1986Date of Patent: October 11, 1988Assignee: Pennwalt CorporationInventor: Vasanth R. Kamath
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Patent number: 4766250Abstract: There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxyaromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.Type: GrantFiled: July 10, 1987Date of Patent: August 23, 1988Assignee: Stauffer Chemical Co.Inventor: Stanley B. Mirviss
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Patent number: 4758641Abstract: A polymer of an olefinically unsaturated carboxylic acid containing 3 to 5 carbon atoms is prepared which contains less than 0.2% by weight unreacted monomer in a solvent selected from acetone and lower alkyl acetates also in the presence with less than 5% of a crosslinker selected from polyalkenyl polyethers of polyhydric alcohols containing more than one alkenyl group per molecule wherein the polyhydric alcohol contains at least 4 carbon atoms and at least 3 hydroxyl groups and initiator selected from peroxides and peroxydicarbonates. Polymerization temperature is 40.degree. to 85.degree. C. and viscosity of the mixture after completing polymerization is less than 1000 cps. About 1 to 10% of the carboxyl groups on the polymer are neutralized.Type: GrantFiled: February 24, 1987Date of Patent: July 19, 1988Assignee: The B F Goodrich CompanyInventor: Chin C. Hsu
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Patent number: 4758642Abstract: According to one aspect of the present invention, an improved method for preparing acrylic copolymer resins is provided in which the polymerization solvent includes an internal olefin. The monomers comprise hydroxy-substituted alkyl (meth)acrylates, and non-hydroxy substituted alkyl (meth)acrylates, and the process provides an improved method for forming low molecular weight acrylic resins useful as components in high solids acrylic coatings suitable for electrostatic spraying. The polymerization solvent can remain in the resin to become the solvent employed in the higher solids coating containing the thus-formed acrylic resins and provides surprisingly improved electrical resistivity and color decreased over previously used polymerization solvents, and has good compatibility with the acrylic monomer/resin system.Type: GrantFiled: December 11, 1985Date of Patent: July 19, 1988Assignee: Exxon Chemical Patents Inc.Inventors: Albet I. Yezrielev, Michael G. Romanelli, William E. Wellman, Richard H. Schlosberg
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Patent number: 4701507Abstract: A process for the emulsion copolymerization of functionalized monomers wherein the improvement comprises the use of methyl isobutyl ketone (MIBK) as a solvent and elevated soap levels in the polymerization.Type: GrantFiled: June 2, 1986Date of Patent: October 20, 1987Assignee: The Goodyear Tire & Rubber CompanyInventors: Robert D. Mate, Dane K. Parker, James C. Blackwell
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Patent number: 4698376Abstract: The present invention relates to formulations which are useful as coating materials for example as an undercoating material or lacquer to improve the bonding between collagen-containing materials and hardening polymeric materials. The formulations contain an active ketone and an olefinically unsaturated monomer which has an active hydrogen.Type: GrantFiled: March 14, 1986Date of Patent: October 6, 1987Assignee: Bayer AktiengesellschaftInventors: Erik Asmussen, Christian Munksgaard
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Patent number: 4695615Abstract: Cyanoacrylate adhesive compositions which employ calixarene compounds as additives give substantially reduced fixture and cure times on de-activating substrates such as wood. The calixarene compounds are preferable employed at levels of about 0.1-2% by weight of the composition.The calixarene compounds particularly useful in this invention may be represented by the formula: ##STR1## where R.sup.3 is H, --CH.sub.2 C(.dbd.O)OH, CH.sub.2 C(.dbd.O)OR.sup.6, --C(.dbd.O)R.sup.8, hydrocarbyl, or trihydrocarbylsilyl or the two R.sup.3 groups together form a divalent hydrocarbyl or oxygen interrupted hydrocarbyl group; R.sup.4 is H or hydrocarbyl; R.sup.5 is hydrocarbyl, hydrocarbyl interrupted by one or more oxygen atoms, or hydrocarbyl substituted with halo, nitro, or oxo groups; R.sup.6 is as defined for R.sup.5 but different therefrom; and R.sup.8 is as defined for R.sup.5 but the same or different therefrom.Type: GrantFiled: January 31, 1986Date of Patent: September 22, 1987Assignee: Loctite (Ireland) LimitedInventors: Raymond G. Leonard, Stephen J. Harris
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Patent number: 4636539Abstract: Cyanoacrylate adhesive compositions which employ calixarene compounds as additives give substantially reduced fixture and cure times on de-activating substrates such as wood. The calixarene compounds are preferably employed at levels of about 0.1-1% by weight of the composition. The calixarene compounds particularly useful in this invention may be represented by the formula: ##STR1## where R.sup.1 is alkyl, alkoxy, substituted alkyl or substituted alkoxy; R.sup.2 is H or alkyl; and n=4, 6, or 8.The compositions are further characterized by a thickener component, which may suitably be selected from various polymers such as poly(methyl methacrylate), methacrylate type copolymers, acrylic rubbers, polyvinyl acetate and poly(.alpha.-cyanoacrylate) or silicas treated with polydialkylsiloxanes or trialkylsilanes.Type: GrantFiled: September 16, 1985Date of Patent: January 13, 1987Assignee: Loctite (Ireland) LimitedInventors: Stephen J. Harris, M. Anthony McKervey, David P. Melody, John Woods, John M. Rooney
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Patent number: 4602073Abstract: Fast curing, two part adhesives and articles bonded therewith are disclosed. The adhesives comprise a first part of free radical polymerizable acrylic monomers and a diazonium salt sufficient to initiate polymerization of said monomers. A second part comprises an activator to induce the free radical decomposition of the diazonium salt, said activator being an aldehyde-amine condensation product. The described curable adhesives are formed just prior to use where the second part containing the activator is placed in contact with the first part. Both the first part and second part component exhibit a high degree of stability when stored separately.Type: GrantFiled: June 7, 1985Date of Patent: July 22, 1986Assignee: National Starch and Chemical CorporationInventors: Martin M. Skoultchi, Alfred G. Battaglia
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Patent number: 4593080Abstract: According to the present invention, an improved method for providing acrylic copolymer resins is provided in which the polymerization solvent comprises a blend of methyl isobutyl ketone and certain alkyl-substituted benzene solvents. The monomers comprise hydroxy-substituted alkyl (meth)acrylate monomers and non-hydroxy substituted alkyl (meth)acrylate monomers, and the process provides an improved method for forming low molecular weight acrylic resins useful as components in acrylic coatings. The polymerization solvent can remain in the resin to become a solvent employed in the higher solids coating containing the thus-formed acrylic resins and provides improved electrical resistivity, improved solvency and decreased surface tensions over prior art polymerization solvents.Type: GrantFiled: October 24, 1984Date of Patent: June 3, 1986Assignee: Exxon Research & Engineering Co.Inventors: Constantine J. Bouboulis, Irving Kuntz
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Patent number: 4568731Abstract: The use of a cyclic compound containing a ##STR1## group, i.e., methone, has been found to allow a poor acrylamide or acrylic acid or 2-acrylamide-2-methylpropane sulfonic acid and its salts monomer to be polymerized to a polymer having improved performance characteristics and/or improved rates of polymerization. Optionally, urea is added with the methone.Type: GrantFiled: September 15, 1983Date of Patent: February 4, 1986Assignee: American Cyanamid CompanyInventors: Peter A. Jarovitzky, Roger E. Neff
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Patent number: 4562234Abstract: An ionically cross-linked acrylic elastomer having a glass transition temperature below 30.degree. C. is prepared by precipitation polymerization of a di- or polyvalent metal salt of acrylic, methacrylic and/or itaconic acid and/or a higher ester of methacrylic acid in an anhydrous organic solvent in which the polymer is insoluble. The metal ions comprise 0.1 to 15% of the monomer mixture.Type: GrantFiled: April 8, 1982Date of Patent: December 31, 1985Assignee: Rohm GmbH Chemische FabrikInventors: Siegmund Besecke, Gunter Schroder