Hydroxy Containing (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/622)
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Patent number: 4726909Abstract: Relates to deodorizing a polyoxypropylene group terminated polyoxyalkylene polyether polyol composition by removing allyloxypropan-2-ol in sufficient amount to reduce the content to less than 200 ppm.Type: GrantFiled: December 23, 1985Date of Patent: February 23, 1988Assignee: BASF CorporationInventors: Jay G. Otten, Edward J. Parker
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Patent number: 4727199Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.Type: GrantFiled: July 10, 1985Date of Patent: February 23, 1988Assignee: Union Carbide CorporationInventor: Stephen W. King
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Patent number: 4719032Abstract: Cyclohexane derivatives of formula IR.sup.1 --Cy--CH.sub.2 --Q--(Cy).sub.m --O--(CO).sub.n --CH.sub.2 --R.sup.2 IwhereR.sup.1 denotes alkyl with 1 to 12 C atoms in which also one or two non-adjacent CH.sub.2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,R.sup.2 denotes H, alkyl with 1 to 12 C atoms in which also one or two non-adjacent CH.sub.2 groups may be replaced by --O--, --CO--, --O--CO-- or --CO--O--,Cy denotes trans-1,4-cyclohexyleneQ denotes --CH.sub.2 -- or --O--,m denotes 1 or 2, andn denotes 0 or 1,are suitable as components of liquid-crystalline phases.Type: GrantFiled: March 21, 1986Date of Patent: January 12, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Andreas Wachtler, Joachim Krause, Reinhard Hittich, Bernhard Scheuble
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Patent number: 4691048Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.Type: GrantFiled: May 10, 1985Date of Patent: September 1, 1987Assignee: Institut Francais du PetroleInventors: Francois Hugues, Dominique Commereuc, Yves Chauvin
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Patent number: 4689435Abstract: Alkylene oxide adducts of organic compounds having an active hydrogen are prepared by a process in which an active hydrogen reactant and an alkylene oxide reactant are reacted in the presence of a catalytically effective amount of one or more bimetallic oxo compounds of the formula (RO).sub.n M--O--M'--O--M(OR).sub.n, wherein each R is (independently) an optionally-substituted organic moiety, M' is a divalent metal selected from the elements of Groups Va, VIa, and VIIa of the Periodic Table, each M is (independently) a trivalent or tetravalent metal, and each n is 2 if the adjacent M is trivalent of 3 if the adjacent M is tetravalent. The products are useful, for instance, as nonionic surfactants in detergent formulations. In certain preferred embodiments, the process yields a product having a very desirable distribution of alkylene oxide adducts.Type: GrantFiled: April 3, 1986Date of Patent: August 25, 1987Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 4665236Abstract: Alkylene oxide adducts of organic compounds having an active hydrogen are prepared by a process in which an active hydrogen reactant and an alkylene oxide reactant are reacted in the presence of a catalytically effective amount of one or more bimetallic oxo compounds of the formula (RO).sub.n M--O--M'--O--M(OR).sub.n, wherein each R is (independently) an optionally-substituted organic moiety, M' is a divalent metal selected from the elements of Groups VIII, Ib, IIb, IIIb, and IVb of the Periodic Table, each M is (independently) a trivalent or tetravalent metal, and each n is 2 if the adjacent M is trivalent of 3 if the adjacent M is tetravalent. The products are useful, for instance, as nonionic surfactants in detergent formulations. In certain preferred embodiments, the process yields a product having a very desirable distribution of alkylene oxide adducts.Type: GrantFiled: April 3, 1986Date of Patent: May 12, 1987Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 4640946Abstract: Polyvinyl alcohol based sizing solution containing a small amount of low ethylene oxide adduct of branched alcohol provides superior operability during sizing and weaving, and yields fabric that exhibits improved finishing performance.Type: GrantFiled: August 14, 1985Date of Patent: February 3, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Donald A. Vassallo, David W. Zunker
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Patent number: 4624299Abstract: A method of indirect liquid phase heat transfer which comprises continuously circulating between a heat generating and a heating source or water-soluble or water-dispersible polymer having a viscosity of less than about 100 centistokes at 100.degree. F., of the formula:R(OAR').sub.xwhereinR is a C.sub.5 to C.sub.36 linear branched or alicyclic aliphatic hydrocarbyl group;O is oxygen;A is a polyoxyalkylene residue having oxyalkylene units derived from ethylene oxide or ethylene oxide and at least one other lower alkylene oxide having 3 or 4 carbon atoms;R' is hydrogen, a C.sub.1 to C.sub.8 alkyl group or nonbornyl; andx is an integer having a value of 1 to 6, wherein for values of x greater than 1 each AR' may be the same or different.Type: GrantFiled: June 28, 1985Date of Patent: November 25, 1986Assignee: Union Carbide CorporationInventors: Ronald H. Harding, George E. Totten
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Patent number: 4617984Abstract: A method of indirect liquid phase heat transfer utilizing as a heat transfer fluid a composition comprising polytetra(methylene oxide) or poly(trimethylene oxide) homopolymers having molecular weights of from about 300 to about 1,000.Type: GrantFiled: June 28, 1985Date of Patent: October 21, 1986Assignee: Union Carbide CorporationInventors: Ronald H. Harding, George E. Totten
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Patent number: 4606837Abstract: Water soluble thickeners made by alkoxylating monohydric alcohol hydrophobes are described. The monohydric alcohol should have at least 18 carbon atoms to be properly hydrophobic. In addition, a large proportion of ethylene oxide must be added, such that the molar ratio of ethylene oxide to monohydric alcohol hydrophobe is at least 40:1. Improved results are obtained if 8-15 moles of propylene oxide are added as a block to the single mole of hydrophobe first. The alkoxylations are necessary to provide the desired viscosities and hydrophilic nature. These thickeners are particularly useful in the glycol-water based fluids of this invention.Type: GrantFiled: January 30, 1985Date of Patent: August 19, 1986Assignee: Texaco Inc.Inventors: Edward E. McEntire, Edward C. Y. Nieh, Robert A. Grigsby, Jr., David R. McCoy
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Patent number: 4600523Abstract: An additive for cleaning preparations comprising a foam-inhibitive effective amount of a compound of the formulaR.sup.1 --CHOH--CHR.sup.2 --O--(CH.sub.2 CH.sub.2 O).sub.n --R.sup.3wherein:R.sup.1 is a straight-chain C.sub.6-16 -alkyl;R.sup.2 is H or a C.sub.1-8 -alkyl;R.sup.3 is a straight-chain or branched C.sub.4-8 -alkyl; andn is a number average of about 7 to 12;with the proviso that the total number of carbon atoms in R.sup.1 and R.sup.2 is between 6 and 16; and a method of inhibiting foam.Type: GrantFiled: December 13, 1984Date of Patent: July 15, 1986Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Robert Piorr, Hans-Joachim Schluessler, Peter Nikolaus
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Patent number: 4582596Abstract: The invention is a process for recovering coal or mineral values from raw coal or mineral ore which comprises subjecting the raw coal or mineral ore in the form of an aqueous pulp, to a floatation process in the presence of a floatation collector, and a flotating amount of a floatation frother which comprises the reaction product of an alitphatic C.sub.6 alcohol and between about 1 and 5 moles of propylene oxide, butylene oxide or mixtures thereof, under conditions such that the coal or mineral values are recovered.Type: GrantFiled: June 4, 1984Date of Patent: April 15, 1986Assignee: The Dow Chemical CompanyInventors: Robert D. Hansen, Roger W. Bergman, Richard R. Klimpel
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Patent number: 4579980Abstract: An ether compound is advantageously produced by an ether exchange reaction of a different ether compound and a hydroxy group containing compound in the presence of a heteropoly acid or an acidic salt thereof as the catalyst. The catalyst is novel and is extremely effective to the present process and brings about less by-products compared to other processes or other catalysts.Type: GrantFiled: February 19, 1985Date of Patent: April 1, 1986Assignee: Nippon Soda Co. Ltd.Inventors: Kiyoshi Kogoma, Norio Sone, Takashi Tobita, Masahiro Shiozaki
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Patent number: 4482753Abstract: The composition of and method for preparing a novel catalyst is disclosed for use in the hydrogenolysis of methyl glycol formals. The novel catalyst is prepared by impregnating a porous alumina substrate with a solution of compounds of nickel and ruthenium, and evaporating and reducing the resulting slurry to provide a substrate impregnated with a catalytic surface composition comprised of a mixture of metallic nickel and metallic ruthenium. When this catalyst is used as the catalyst in the hydrogenolysis of methyl glycol formals, improved reaction rates in the formation of the desired glycol dimethyl ether are obtained.Type: GrantFiled: March 28, 1983Date of Patent: November 13, 1984Assignee: Olin CorporationInventors: Tai-Nang Huang, Carlos G. Fernandez
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Patent number: 4474678Abstract: Detergent compositions particularly useful in hard-surface cleaning comprise an alkanol ethoxylate component which consists essentially of a mixture of compounds of the formula R--O--CH.sub.2 CH.sub.2 O--.sub.x H, wherein R is an alkyl group of from 8 to 18 carbon atoms, said alkyl group having a linear carbon chain in at least about 50 percent of the ethoxylate molecules; wherein the --O--CH.sub.2 --CH.sub.2 --O--.sub.x H ether substituent is, in at least 40 percent of the molecules of the mixture, bound to R at a carbon atom which is neither a terminal carbon atom nor a carbon atom adjacent to a terminal carbon atom; and wherein x has an average value for all ethoxylate molecules of the mixture which is in the range from about 3 to 9; said ethoxylate component being further characterized as having a hydrophile-lipophile balance that is between about 10.4 and 12.Type: GrantFiled: March 29, 1982Date of Patent: October 2, 1984Assignee: Shell Oil CompanyInventors: Eugene F. Lutz, Donald L. Wood, Hans E. Kubitschek
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Patent number: 4465877Abstract: Alkanol alkoxylates having utility, for instance, as nonionic surfactants in detergent formulations are prepared by the reaction of C.sub.6 to C.sub.30 alkanols with C.sub.2 to C.sub.4 alkylene oxides in the presence of a catalytically effective amount of one or more soluble basic compounds of magnesium and additionally in the presence of as a reaction activator at least about 2 percent by mole, calculated on moles of alkanol, of alkoxylates of one or more C.sub.1 to C.sub.30 alkanols having in the alkoxylate molecules from one to about 30 adducts of one or more alkylene oxides selected from the class consisting of C.sub.2 to C.sub.4 alkylene oxides.Type: GrantFiled: August 3, 1983Date of Patent: August 14, 1984Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 4453023Abstract: The process for preparing nonionic surfactants wherein a narrower molecular weight distribution is obtained by the use of a barium catalyst which comprises reacting a reactive hydrogen compound selected from the group consisting of monohydric alcohols having from about 8 to about 20 carbon atoms and a difunctional polypropylene oxide polymer having an average molecular weight in the range of 1000 to 5000 with an alkylene oxide having 2 to 4 carbon atoms at a temperature at which the reaction proceeds in the presence of at least a catalytic amount of a barium salt selected from the group consisting of barium hydroxide, barium alkoxides, barium phenoxides, hydrates thereof or mixtures thereof and a catalytic amount of an oxyalkylation catalyst promoter.Type: GrantFiled: December 30, 1982Date of Patent: June 5, 1984Assignee: Union Carbide CorporationInventors: James H. McCain, Louis F. Theiling, Jr.
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Patent number: 4453022Abstract: The process for preparing nonionic surfactants wherein a narrower molecular weight distribution is obtained by the use of a calcium and/or strontium catalyst which comprises reacting a reactive hydrogen compound selected from the group consisting of monohydric alcohols having from about 8 to about 20 carbon atoms and a difunctional polypropylene oxide polymer having an average molecular weight in the range of 1000 to 5000 with an alkylene oxide having 2 to 4 carbon atoms at a temperature at which the reaction proceeds in the presence of at least a catalytic amount of a basic salt of calcium and/or strontium selected from the group consisting of hydroxide, alkoxide and phenoxides and a catalytic amount of an oxyalkylation catalyst promoter.Type: GrantFiled: April 21, 1982Date of Patent: June 5, 1984Assignee: Union Carbide CorporationInventors: James H. McCain, Louis F. Theiling, Jr.
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Patent number: 4436638Abstract: An additive composition effective in the release of stuck pipe in a borehole during a drilling operation which composition contains propoxylated C.sub.18 -C.sub.32 alkanols, an oil-soluble emulsifier-wetting agent and a liquid hydrocarbon diluent.Type: GrantFiled: July 29, 1981Date of Patent: March 13, 1984Assignee: Exxon Research & Engineering Co.Inventors: Thad O. Walker, Patricia C. Matthews
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Patent number: 4399313Abstract: Non-ionic products of the formula:R--X--[C.sub.2 H.sub.3 (OCH.sub.2 CH.sub.2).sub.n (OH)--CH.sub.2 --Y--R'in which R and R' denote alkyl or alkenyl radicals having from 6 to 20 carbon atoms, the sum of the numbers of carbon atoms in R and R' being 24 to 32; X denotes an oxygen atom, a sulphur atom or a sulphoxide group; Y denotes a sulphur atom, a sulphoxide group or a methylene group (if Y denotes methylene, the sum of the numbers of carbon atoms in R and R' is 22 to 30); and n denotes an integer or decimal number from 1 to 40 are disclosed. These non-ionic compounds are suitable for use in pharmaceutical or cosmetic applications, in particular for the care of the skin or hair.Type: GrantFiled: October 14, 1980Date of Patent: August 16, 1983Assignee: Societe Anonyme dite: L'OrealInventors: Guy Vanlerberghe, Henri Sebag
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Patent number: 4375564Abstract: Alkanol alkoxylates having utility, for instance, as nonionic surfactants in detergent formulations are prepared by the reaction of C.sub.1 to C.sub.30 alkanols with C.sub.2 to C.sub.4 alkylene oxides in the presence of a catalytically effective amount of a co-catalyst combination comprising as a first component one or more soluble, basic compounds of magnesium and as a second component one or more soluble compounds of at least one element selected from the group consisting of aluminum, boron, zinc, titanium, silicon, molybdenum, vanadium, gallium, germanium, yttrium, zirconium, niobium, cadmium, indium, tin, antimony, tungsten, hafnium, tantalum, thallium, lead, and bismuth.Type: GrantFiled: December 23, 1981Date of Patent: March 1, 1983Assignee: Shell Oil CompanyInventor: Charles L. Edwards
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Patent number: 4375565Abstract: The subject invention relates to compositions of matter having the following structural formula: ##STR1## In this formula, R.sup.1 represents a C.sub.8 -C.sub.20 alkyl radical, R.sup.2 stands for a C.sub.1 -C.sub.5 alkyl radical, and n is a number, 4 through 15. These compounds are low foaming and have acceptable biodegradability. They are particularly useful in the formulation of automatic dishwashing detergents.Type: GrantFiled: October 15, 1981Date of Patent: March 1, 1983Assignee: BASF AktiengesellschaftInventors: Norbert Greif, Erhard Klahr, Wolfgang Trieselt
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Patent number: 4368337Abstract: A process is described for converting glycol dialkyl ether without substantial formation of olefin oligomers by reaction with water, comprising reacting a feed glycol di-tertiary alkyl ether represented by structural formula (A) with water using a strongly acidic cation-exchange resin as a catalyst and a reaction temperature of from 40.degree. C. to 150.degree. C. under a pressure of from 1 to 70 kg/cm.sup.2 (absolute pressure) in a molar ratio of water/feed glycol di-tertiary alkyl ether represented by the structural formula (A) of from 0.Type: GrantFiled: March 30, 1981Date of Patent: January 11, 1983Assignee: Maruzen Oil Co., Ltd.Inventors: Kinya Tawara, Hiroki Kamiyama, Shigenori Nakashizu, Takashi Kaneko, Tadahiro Wakui, Tadashi Matsumoto
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Patent number: 4317938Abstract: A process for the preparation of C.sub.8 to C.sub.20 secondary alkanol alkoxylates from C.sub.8 to C.sub.20 olefins and alkylene and/or polyether glycols, which comprises sulfating the olefins with sulfuric acid to obtain C.sub.8 to C.sub.20 secondary monoalkyl sulfuric acids, introducing said monoalkyl sulfuric acids and said glycols into an alkoxylation reaction zone, and reacting said monoalkyl sulfuric acids and said glycols under specified conditions of time and temperature.Type: GrantFiled: December 31, 1980Date of Patent: March 2, 1982Assignee: Shell Oil CompanyInventor: Eugene F. Lutz
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Patent number: 4302613Abstract: Strontium and barium-based catalyzed alkoxylation of alcohols of all classes is carried out more rapidly and produces a more peaked reaction product when carried out in the presence of co-catalysts such as calcium oxide, calcium carbide, calcium hydroxide, magnesium metal, magnesium hydroxides, zinc oxide, and aluminum metal.Type: GrantFiled: August 22, 1980Date of Patent: November 24, 1981Assignee: Conoco Inc.Inventors: Kang Yang, Gerald L. Nield, Paul H. Washecheck
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Patent number: 4282387Abstract: The invention describes an improved process for preparing polyols by reacting a mono-epoxy compound such as propylene oxide with a hydroxyl-containing initiator compound such as glycerine in the presence of a catalyst, the improvement being that the catalyst is added in the form of a calcium, strontium or barium salt of an organic acid such as acetic acid.Polyols prepared by this process can be employed to prepare polyurethanes without removing the catalyst.Type: GrantFiled: December 26, 1979Date of Patent: August 4, 1981Assignee: The Dow Chemical CompanyInventors: Franciszek Olstowski, John L. Nafziger
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Patent number: 4228310Abstract: Covers a method of preparing polyether polyols useful in making a polyisocyanurate polymer by oxyalkylating an alcohol by the catalytic addition of an alkylene oxide to said alcohol in presence of a catalyst selected from the group consisting of carbamate salts, aminophenols, hexahydro-s-triazines and tetrahydrooxadiazines.Type: GrantFiled: March 19, 1979Date of Patent: October 14, 1980Assignee: Texaco Development Corp.Inventors: George P. Speranza, Robert L. Zimmerman, Thomas H. Austin
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Patent number: 4223164Abstract: Basic compounds of strontium catalyzed the ethoxylation of alcohols in the presence of phenol or alkylphenol co-catalyst. Strontium-produced ethoxylates have sharper ethylene oxide distributions, lower free alcohol, lower pour points, and better detergency than the ethoxylates obtained from alkali base catalysis.Type: GrantFiled: July 2, 1979Date of Patent: September 16, 1980Assignee: Conoco, Inc.Inventors: Kang Yang, Gerald L. Nield, Paul H. Washecheck
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Patent number: 4193892Abstract: In a process for the preparation of an olefin oxide polymerization catalyst comprising:(i) admixing calcium, ammonia, an alkylene oxide modifier, and an organic nitrile modifier, the alkylene oxide consisting of carbon, hydrogen, and oxirane oxygen atoms and the organic nitrile consisting of carbon, nitrogen, and hydrogen atoms, at least one hydrogen atom being acidic, to form a slurry of modified calcium hexammine in ammonia; and(ii) evaporating ammonia to provide a solid residue,the improvement comprising:aging the solid residue at a temperature in the range of about 150.degree. C. to about 225.degree. C.Type: GrantFiled: July 28, 1978Date of Patent: March 18, 1980Assignee: Union Carbide CorporationInventors: George L. Goeke, Frederick J. Karol
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Patent number: 4182918Abstract: A process has been invented for the preparation of dihydric substituted phenols which comprises reacting a solution, which is essentially anhydrous and free from hydrogen peroxide, of a percarboxylic acid in an inert organic solvent with a monohydric substituted phenol, which is derived from benzene, naphthalene or anthracene and still contains at least one free hydrogen atom in the aromatic nucleus, at temperatures from about -20.degree. C. to about 120.degree. C.The dihydric substituted phenols obtained according to the invention are known, important industrial intermediate products used in the fields of photography, dyestuffs and plastics, as well as in the scent and flavoring areas.Type: GrantFiled: December 5, 1977Date of Patent: January 8, 1980Assignee: Bayer AktiengesellschaftInventors: Hermann Seifert, Helmut Waldmann, Wulf Schwerdtel, Wolfgang Swodenk
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Patent number: 4155742Abstract: A unit dosage form comprising one or more active ingredients and a water-soluble binder in which the water-soluble binder comprises, as a main component, a product obtained by condensing a polyoxyethylene alkyl, alkylphenyl or alkenyl ether having the following formula (I):r-o--(ch.sub.2 ch.sub.2 o).sub.n H (I)wherein R is alkyl or alkenyl having 8 to 22 carbon atoms or alkylphenyl group having 8 to 22 carbon atoms in the alkyl group, and n is an integer of from 50 to 500, with 1-epoxyethyl-3,4-epoxycyclohexane having the following formula (II): ##STR1## the molar ratio of the compound of the formula (II) to the compound of the formula (I) being in the range of from 0.05 to 2.5.Type: GrantFiled: January 18, 1978Date of Patent: May 22, 1979Assignee: Kao Soap Co., Ltd.Inventors: Akira Sakurai, Yoshimi Tsuchiya, Mikio Kanno
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Patent number: 4139567Abstract: Copolyether glycols are prepared by copolymerizing alkylene oxides or cyclic acetals and tetrahydrofuran, using(1) a polymeric catalyst which contains sulfonic acid groups; and(2) a chain terminator which is water or an alkanediol.Type: GrantFiled: January 9, 1978Date of Patent: February 13, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerfried Pruckmayr