Material Contains A Group Ia Metal Atom (li, Na, K, Rb, Cs, Fr) Patents (Class 528/147)
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Patent number: 4431783Abstract: Polymerization of vinyl chloride in aqueous suspension using a polymerization reactor having adherently deposited on internal surfaces thereof a build-up suppressant coating comprising a product of build-up suppressant activity formable by (and preferably formed by) the condensation of an effective 1-naphthol (preferably 1-naphthol itself) and formaldehyde. The condensation is preferably effected in a base-catalyzed reaction; it may also (less preferably) be effected in an acid-catalyzed reaction. The coating product itself and a process for its production are also claimed.Type: GrantFiled: October 26, 1981Date of Patent: February 14, 1984Assignee: Imperial Chemical Industries PLCInventors: Robert W. Walker, John Stuart-Webb
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Patent number: 4420571Abstract: Compositions useful as friction particles comprised of tri- and/or tetrafunctional phenol, difunctional phenol, aldehyde, a protective colloid, and a reaction promoting compound. The friction particles are formulated into friction elements. A process for producing the friction particles in particulate form.Type: GrantFiled: July 13, 1982Date of Patent: December 13, 1983Assignee: Union Carbide CorporationInventors: John R. Blickensderfer, Luba A. Pacala
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Patent number: 4414378Abstract: A granular or powdery resin which is a condensation product of a phenol and formaldehyde, said granular or powdery resin being characterized by(A) containing spherical primary particles and secondary particles resulting from the agglomeration of the primary particles, each of the particles having a particle diameter of 0.1 to 150 microns,(B) having such a size that at least 50% by weight thereof can pass through a 100 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 50 ppm,(D) having a D.sub.990-1015 /D.sub.1600 ratio of from 0.2 to 9.0 and a D.sub.890 /D.sub.1600 ratio of from 0.09 to 1.0 in its infrared absorption spectrum measured by a KBr tablet method, wherein D.sub.1600 represents the absorption intensity of an absorption peak at 1600 cm.sup.-1, D.sub.990-1015 represents the highest absorption intensity of absorption peaks at 990 to 1015 cm.sup.-1, and the D.sub.890 represents the absorption intensity of an absorption peak at 890 cm.sup.Type: GrantFiled: April 15, 1982Date of Patent: November 8, 1983Assignee: Mitsubishi Chemical Industries LimitedInventors: Hiroaki Koyama, Shigeo Shimizu
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Patent number: 4395535Abstract: A process for the manufacture of condensation products of phenols and isobutyraldehyde by reacting the phenols and isobutyraldehyde at elevated temperature in a mole ratio of 0.5:1 to 1.5:1 in the presence of acid or compounds hydrolyzable to acids as catalysts, subsequent neutralization and removal of the resultant reaction water by distillation wherein the reaction products obtained in this manner are also subjected to a water-vapor distillation.Type: GrantFiled: October 6, 1981Date of Patent: July 26, 1983Assignee: BASF AktiengesellschaftInventors: Juergen Nieberle, Karl-Clemens Peters, Wolfgang Reuther, Heinz-Hilmar Bankowsky
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Patent number: 4393189Abstract: A method of preparing a thermoplastic, water-soluble, phenolic aldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the aldehyde are reacted to less than 100 percent completion in an amount so that the aldehyde to phenolic compound ratio is in the range of about 0.6 to about 1.5 and at an acidic pH and for a period of time equivalent to about 3 hours to about 10 hours when the temperature is in the range of about 55.degree. F. (13.degree. C.) to about 90.degree. F. (32.degree. C.) to produce a resinous mixture. In the second stage the pH of the reaction is adjusted within the range above about 7.0 to about 7.Type: GrantFiled: November 16, 1981Date of Patent: July 12, 1983Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
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Patent number: 4381369Abstract: A water-base well drilling, workover or completion fluid containing a fluid loss control agent prepared by pre-reacting sulfonated phenol with formaldehyde under alkaline conditions and then reacting the mixture with phenol under controlled conditions is described.Type: GrantFiled: October 9, 1981Date of Patent: April 26, 1983Assignee: Georgia-Pacific CorporationInventor: Howard W. Holmquist
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Patent number: 4378453Abstract: An adhesive consisting comprising an alkoxyphenol derivative/resorcin derivative/formaldehyde cocondensate has a high adhesive strength and can bond firmly polyester fibrous material with rubber.Type: GrantFiled: April 6, 1982Date of Patent: March 29, 1983Assignee: Bridgestone Tire Co., Ltd.Inventors: Toshihiro Yotsumoto, Kazuo Koyama
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Patent number: 4374962Abstract: An adhesive comprising a cocondensate of formaldehyde with m-alkylphenol or its derivative and alkylresorcin is excellent in the adhesion, heat resistance and flexibility and can bond firmly polyester fibrous material with rubber.Type: GrantFiled: April 6, 1982Date of Patent: February 22, 1983Assignee: Bridgestone Tire Company LimitedInventors: Toshihiro Yotsumoto, Kazuo Koyama
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Patent number: 4373062Abstract: Phenol-formaldehyde and phenol-resorcinol-formaldehyde resinous aqueous syrups useful as thermosetting binders or adhesives are prepared by reacting, a phenol-formaldehyde resin composition firstly at atmospheric reflux temperature at a substantially neutral pH of 5.8 to 8.5 and a formaldehyde to phenol mol ratio between 1.7 to 2.8 for a period of 20 to 120 minutes; reacting secondly with added formaldehyde, if necessary, and also needed alkali metal hydroxide to produce mol ratios of 2.1 to 2.8 and 0.10 to 0.38, respectively, per mol of phenol, for a period of at least two minutes at reflux to produce a liquid phenol-formaldehyde thermosetting resin. The setting time can be decreased, if desired, by using two portions of syrup, reacting one portion for a greater time-temperature period than the other and combining the two portions.Type: GrantFiled: April 20, 1981Date of Patent: February 8, 1983Inventor: Gordon E. Brown
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Patent number: 4366303Abstract: Particulate resoles are produced by mixing phenol, formaldehyde and amine in an aqueous medium containing a protective colloid. The resoles exhibit improved cure rate and sinter resistance when an alkaline compound is added to the reaction mixture after particulate formation.Type: GrantFiled: December 11, 1981Date of Patent: December 28, 1982Assignee: Union Carbide CorporationInventor: Peter W. Kopf
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Patent number: 4362853Abstract: Carboxylate salts, prepared by a Mannich reaction and useful in the preparation of water-borne coatings, have the general formula ##STR1## where R.sup.1 represents an aliphatic, aromatic, or araliphatic divalent group which may contain a further --COO.sup.- M.sup.+ ; R.sup.2 represents --H, --CH(R.sup.3)N(R.sup.10)R.sup.1 COO.sup.- M.sup.+, or alkyl which may be substituted by --COO.sup.- M.sup.+, --CH(R.sup.3)OH, or --CH(R.sup.3)OR.sup.8, R.sup.1 and R.sup.2 containing together not more than one --COO.sup.- M.sup.+ ; R.sup.3 represents --H or alkyl; each R.sup.4 represents --H, halogen, alkyl, or alkenyl; R.sup.5 represents --H, halogen, alkyl, alkenyl, or a group --CH(R.sup.3)OH, --CH(R.sup.3)OR.sup.8, or --CHR.sup.3 --NR.sup.2 --R.sup.1 --COO.sup.- M.sup.+ ; either R.sup.6 represents --H and R.sup.7 represents the residue of a polyepoxide, preferably of average mol. wt. 1000-5000, or R.sup.6 represents a covalent bond linked to the group R.sup.7, and R.sup.Type: GrantFiled: October 13, 1981Date of Patent: December 7, 1982Assignee: Ciba-Geigy CorporationInventor: Christopher G. Demmer
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Patent number: 4350800Abstract: A process for the preparation of synthetic resins based on resorcinol compounds which comprises reacting a resorcinol pitch which is obtained in the manufacture of resorcinol from benzenedisulfonic acid in at least one step with an oxo-compound selected from aldehydes, ketones and compounds based on or splitting off at least one of these substances, and the use of the products as binders for abrasive articles.Type: GrantFiled: September 14, 1981Date of Patent: September 21, 1982Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Franz Landauer, Klaus Schmiedel
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Patent number: 4314050Abstract: A method of preparing a thermoplastic, long-chain water-soluble, phenolic formaldehyde resin and the composition are provided to enhance the flexibility and resistance to compression fatigue breakage of glass fibers to which the resin has been applied. The method involves two steps. In the first step, the phenolic compound and the formaldehyde are reacted to less than 100 percent completion in an amount so that the formaldehyde to resorcinol ratio is in the range of about 0.6 to about 2.0 and at an acidic pH and for a period of time equivalent to about 1 hour to about 20 hours when the temperature is in the range of about 30.degree. F.(-31 1.1.degree. C.) to about 122.degree. F. (50.degree. C.) to produce a resinous mixture having a predominant amount of trimer polymer along with minor amounts of dimer and higher oligomer polymers and along with unreacted phenolic compound and aldehyde. In the second stage the pH of the reaction is adjusted within the range above of about 7.0 to about 7.Type: GrantFiled: October 30, 1978Date of Patent: February 2, 1982Assignee: PPG Industries, Inc.Inventor: Mikhail M. Girgis
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Patent number: 4269949Abstract: A finished resin comprising a highly condensed phenol formaldehyde resole resin which has green groups formed by a low condensation phenol formaldehyde resin, the finished resin being modified by addition of a weak acid and a non-cellulosic protective colloid to improve reactivity and flow properties thereof.Type: GrantFiled: June 27, 1979Date of Patent: May 26, 1981Assignee: Borden, Inc.Inventors: Charles H. Hickson, Pitchaiya Chandramouli
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Patent number: 4268657Abstract: Improved friction elements suited for use for example in an automotive or similar brake or in a clutch are provided by employing therein as a binder the reaction product of phenol, formaldehyde, and monoalkylphenol having from 4 to about 20 carbon atoms in the alkyl group. The mole ratio range of phenol:alkylphenol:formaldehyde is about 2:1-5:1-7 and the number of moles of phenol and alkylphenol combined exceeds the number of moles of formaldehyde. An improved method of making friction elements is also provided which uses such binder.Type: GrantFiled: December 10, 1979Date of Patent: May 19, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Anthony P. Manzara
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Patent number: 4264671Abstract: Low-color or white, dilutable condensation products of formaldehyde and phenol in molar ratios of 1.9-5.0:1, characterized by carbon-13 nuclear magnetic resonance spectra as having at least about 30 molar percent of the total formaldehyde content of the resin bound to phenol nuclei in benzyl formal groups of the form Ph--(CH.sub.2 O).sub.n --CH.sub.2 OH wherein n.gtoreq.1, and less than about 40 molar percent of the total formaldehyde content of the resin bound to phenol nuclei in methylol groups of the form Ph--CH.sub.2 OH, wherein Ph is a phenol nucleus. Phenol, water and an alkaline catalyst, limited to 0.5-2.2 moles of catalyst per 100 moles of phenol and preferably lithium carbonate, are mixed with formaldehyde at 1.9-5.0 formaldehyde to phenol ratios. The reaction mixture is heated at a uniform rate over 1 hour to reflux temperature and refluxed until a viscosity of 400-500 centipoise at 50-75% solids is attained. The mixture is cooled to 50.degree. C.Type: GrantFiled: August 2, 1978Date of Patent: April 28, 1981Assignee: Weyerhaeuser CompanyInventors: M. Frank Gillern, Katashi Oita, Robert J. Teng, George T. Tiedeman
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Patent number: 4260730Abstract: A bisphenol is reacted with formaldehyde in solution in alcohol in the presence of an alkali metal hydroxide, preferably at a pH of from 7-10, to provide a polymethylol derivative. Nitric acid is then added to precipitate the hydroxide and an excess is preferably used to provide an acid pH, preferably pH 1-3, and the acidic mixture is heat reacted to remove water of etherification. The nitric acid catalyst is then precipitated with alkali metal hydroxide to enable easy removal of both acid and alkali as an insoluble salt.Type: GrantFiled: January 3, 1980Date of Patent: April 7, 1981Assignee: DeSoto, Inc.Inventors: Kazys Sekmakas, Thomas H. Plaisance
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Patent number: 4259473Abstract: Self-curing or curable materials are obtained from the distillation residues of coal hydrogenation by condensing a residue of this type having a softening point of 30.degree. to 54.degree. C. in a first stage with a mono- or dihydroxybenzene and/or a methylhydroxybenzene and/or an ethylene substituted benzene. These reactants are used at a ratio of residue to benzene derivative between 1:1 and 2:1 and the reaction is carried out in the presence of acid at a pH of 1 to 2 and at a temperature of 90.degree. to 100.degree. C. In a second stage the thus obtained reaction product is then further reacted at about the same temperature with an aldehyde. As a result a novolak-type resin is obtained. The invention permits the making of inexpensive self-curing or curable materials with properties similar to those of phenolic acids. Besides, the invention also provides an outlet for the high boiling residue of the extractive coal hydrogenation which otherwise had little use.Type: GrantFiled: January 15, 1980Date of Patent: March 31, 1981Assignee: Bergwerksverband GmbHInventors: Ingo Romey, Menachem El-Roy
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Patent number: 4244906Abstract: Phenol-aldehyde resins are prepared by condensing phenol with formaldehyde and isobutyraldehyde in the presence of an alkali. The resulting resins are particularly suited for manufacturing products such as fiberboard and chipboard.Type: GrantFiled: May 14, 1979Date of Patent: January 13, 1981Assignee: Deutsche Texaco AktiengesellschaftInventors: Karl-Heinz Heinemann, Georg Michalczyk, Gerd Ripkens
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Patent number: 4221873Abstract: A method for producing a phenol foam plastic, consisting in that polycondensation of phenols with formaldehyde is conducted with simultaneous foaming and curing in the presence of a foaming agent and an acid or alkaline catalyst. Used as the phenols are pyrocatechol, hydroquinone, resorcinol, 5-methyl resorcinol, shale alkyl resorcinols, shale total phenols, or various combinations of said phenols. The method is simple and permits obtaining a foam plastic with improved physico-mechanical properties.Type: GrantFiled: April 17, 1978Date of Patent: September 9, 1980Inventors: Leonid V. Volodko, Mikhail A. Ksenofontov, Ljudmila E. Ostrovskaya, Galina G. Dzivitskaya, Igor D. Goretsky, Vasily M. Khoruzhy, Nikolai M. Denisjuk, Anatoly Y. Volokh, Oleg N. Pogorelsky
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Patent number: 4216088Abstract: The present invention relates to the field of environmental protection.The proposed method of treatment of phenolic waters formed in the manufacture of phenol-formaldehyde resins consists in that said phenolic waters are mixed with formaldehyde and the product of phenol-formaldehyde condensation taken in the quantity of 15-25 percent parts by weight per 100 parts by weight of phenolic waters, and the mixture is heated in the presence of alkali.Type: GrantFiled: November 13, 1978Date of Patent: August 5, 1980Inventors: Anatoly M. Juferov, Galina I. Shakhova, Olga M. Nesterova
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Patent number: 4198499Abstract: Resol type phenol resins containing scarcely or no phenol mononucleus compounds (monomers) and phenol dinuclei compounds (dimers) and their methylolated derivatives and scarcely containing molecules having an apparent molecular weight of more than 2500 are produced by reacting phenol with formaldehyde in the presence of an alkaline catalyst in a molar ratio of 3.0 to 6.0 moles of formaldehyde and 0.05 to 2.0 moles of the alkaline catalyst per mole of phenol, neutralizing the reaction solution with an acid to pH 4.5 to 6.5 and precipitating the resulting product for separation.Type: GrantFiled: August 28, 1978Date of Patent: April 15, 1980Assignee: Hitachi Chemical Company, Inc.Inventors: Susumu Konii, Masatoshi Yoshida, Yukio Yoshimura, Takehiko Ishibashi, Shizuo Sakamoto
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Patent number: 4182732Abstract: A coating and adhesive composition that may be in finely divided powder form is provided comprising a solid phenolic resole (one-step) resin having a gel time of between 150 seconds to about 250 seconds at 150.degree. C., said resin being the reaction product of bisphenol-A and formaldehyde at a mole ratio between about 2.11 to 2.64 moles of formaldehyde per mole of bisphenol-A in the presence of a catalytic quantity of a condensation catalyst at a temperature of at least about 70.degree. C. that is acidified to a pH from about 3 up to 7 and dehydrated.Type: GrantFiled: September 28, 1977Date of Patent: January 8, 1980Assignee: Union Carbide CorporationInventor: John S. Fry
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Patent number: 4176106Abstract: The present invention provides particular phenol/formaldehyde resoles which are especially useful as foamable resins, and further provides cellular phenolic products having physical properties which are especially attractive for end-use application as construction foam. The resoles are characterized by a particular relationship between their viscosity and water content, expressed as the area bounded by certain points on a plot of resole viscosity on a logarithmic scale, as a function of water content of the resole, the particular area depending upon the mole ratio of formaldehyde-to-phenol at which the resole has been condensed. It has been found that phenol-formaldehyde resoles having the defined viscosity/water relationship are capable of providing phenolic foam having acceptable foam processability, a foam density from about 1.90 to about 3.Type: GrantFiled: July 28, 1977Date of Patent: November 27, 1979Assignee: Union Carbide CorporationInventors: Wallace G. Reid, Rakesh Saini, Kenneth E. Atkins
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Patent number: 4170697Abstract: Silicon halides will react chemically with polyols to produce polyol silicate resinous products which will react chemically with polyisocyanates to produce polyisocyanate silicate solid or cellular solid products.Type: GrantFiled: June 23, 1978Date of Patent: October 9, 1979Inventor: David H. Blount
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Patent number: 4168365Abstract: A flame-retardant phenolic resin which comprises the product obtained on(a) reacting at least one halogenated compound represented by the general formula (I) ##STR1## wherein A is --CH.dbd.CH.sub.2 or --O--CH.sub.2 --CH.dbd.CH.sub.2, X is a chlorine atom or a bromine atom, and n is an integer of 1, 2 or 3, with at least one phenol in the presence of an acidic catalyst; and(b) reacting the resulting reaction product with at least one phosphoric acid ester compound containing a phenolic OH group represented by the general formula (II), (III) or (IV). ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents an unsubstituted or substituted hydrocarbyl group, where R.sub.1 and R.sub.2 may be the same or different, and n is 1, 2 or 3, and at least one aldehyde or a precursor thereof in the presence of an acidic or alkali catalyst; and a process for producing the flame-retardant phenolic resin.Type: GrantFiled: November 30, 1977Date of Patent: September 18, 1979Assignee: Matsushita Electric Works, Ltd.Inventors: Hidekazu Takano, Toshiharu Mikawa, Kazuhiko Nemoto
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Patent number: 4137220Abstract: A Novolak epoxy resin is prepared by adding an aqueous solution of alkali metal hydroxide to a solution of Novolak phenolic resin in epichlorohydrin, distilling off water during said addition in the form of an azeotrope with epichlorohydrin and recycling the latter, while maintaining the reaction medium at 60-80.degree. C and at a pH between 7 and 8 and a water content of from 0.5 to 2.5 wt.% in said medium.The thermosetting resin thus obtained can be used in applications requiring resins with low chlorine contents, low viscosity and high epoxy value.Type: GrantFiled: December 6, 1976Date of Patent: January 30, 1979Assignee: Societa' Italiana Resine S.I.R. S.p.A.Inventors: Giorgio Lazzerini, Silvio Vargiu, Mario Pitzalis
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Patent number: 4098770Abstract: A method of preparing a modified phenol-formaldehyde resin in solid particulate form comprising reacting together, in an aqueous medium, phenol and formaldehyde, in a ratio of 1.0 mole phenol to between 1.8 and 3.5 moles of formaldehyde, in the presence of between 0.1 and 1.0 moles of a basic catalyst; continuing this reaction until a desired viscosity is reached; modifying the reaction system by adding thereto between 0 and 30%, based on the weight of phenol originally taken of a non-phenolic polyhydroxy compound; spray drying the thus modified liquid resin in a pressure nozzle drier, and chilling the spray dried particulate solid. These solid resins are redispersible in water and stable on storage, compared to the known aqueous, equivalent, systems.Type: GrantFiled: September 15, 1976Date of Patent: July 4, 1978Assignee: Reichhold Chemicals LimitedInventors: Antoine Berchem, Krishan Kumar Sudan, Edward Michael Gres