Nitrogen-containing Alcohol, Inorganic Alcoholate, Or Ether Patents (Class 528/111)
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Patent number: 4420606Abstract: An epoxy resin composition is disclosed. The epoxy resin is useful as a flexible adhesive.The composition comprises a modified epoxy base resin with a curing agent. The resin is modified by partial reaction with a polyoxyalkylene monoamine. No solvent is present in the formulation.Type: GrantFiled: October 15, 1982Date of Patent: December 13, 1983Assignee: Texaco Inc.Inventor: Harold G. Waddill
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Patent number: 4417010Abstract: A liquid curing agent for polyepoxides having terminal epoxide groups is made from a blend of a normally solid aliphatic polyol and a monoimidazole. Cured compositions made from the curing agent and the polyepoxide are useful in various types of plastics applications.Type: GrantFiled: February 2, 1983Date of Patent: November 22, 1983Assignee: Celanese CorporationInventor: David A. Shimp
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Patent number: 4405662Abstract: A thermosetting resinous binder composition, heat-curable in combination with a transesterification-promoting metal compound as a catalyst to provide an insoluble infusible coating, comprising a mixture of:(1) a non-acidic resinous compound essentially free of ethylenical unsaturation, having a molecular weight of at least 900 and a hydroxyl content of at least 0.Type: GrantFiled: September 24, 1982Date of Patent: September 20, 1983Assignee: Shell Oil CompanyInventors: Werner T. Raudenbusch, Adrianus J. M. Barnhoorn, Petrus G. Kooijmans, Willem L. Sederel, Adrianus M. C. Van Steenis, Theresia F. M. Schets
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Patent number: 4403078Abstract: A novel epoxy resin curing agent comprises a polyoxyalkylenediamine biguanide salt. This novel group of compounds has an extended pot life and good adhesive properties.Type: GrantFiled: September 7, 1982Date of Patent: September 6, 1983Assignee: Texaco Inc.Inventors: David R. McCoy, Harold G. Waddill
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Patent number: 4401777Abstract: Disclosed is a curable resin composition comprising (a) at least one maleimide compound selected from the group consisting of N-(alkenylphenyl)maleimide derivatives, and dimers and polymers thereof and (b) one or more kinds of epoxy resins, each having at least one epoxy group in the unit molecule thereof. The resin composition may contain, besides the above two components, an amino compound as a further component (c). The resin composition may comprise a prepolymer of any two components among the three components (a), (b) and (c) and the remaining component. The resin compositions are useful as molding materials, for the fabrication of laminates, and as varnishes, including insulation varnishes and impregnating varnishes.Type: GrantFiled: October 20, 1981Date of Patent: August 30, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Hikotada Tsuboi, Motoo Kawamata, Masayuki Oba, Nobuhito Koga
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Patent number: 4396649Abstract: Tertiary nitrogen-containing chain-extended epoxy resins, capable of forming stable aqueous emulsions, may be produced by chain-extending an epoxy resin using a tertiary nitrogen containing ether or ester polyol for example, particularly, polycaprolactone which has been polymerization initiated by a tertiary amine polyol such as N-methyl diethanolamine. The corresponding amine salt is formed by treatment with an acid for example acetic acid and the resulting cationic polymer may be dispersed in water to form a cationic emulsion capable of being coated onto a substrate by electrodeposition. The chain extended resins, by virtue by their content of free epoxy groups are also usable for cross-linking and other uses.Type: GrantFiled: November 20, 1981Date of Patent: August 2, 1983Assignee: Interox Chemicals LimitedInventors: Brian E. Bailey, Joseph W. Lister
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Patent number: 4383118Abstract: Glycidyl polyethers of polyphenols are prepared by reacting at least one alkali metal salt of a polyphenol with at least one 1-halogeno-2,3-epoxyalkane, in an anhydrous and essentially aprotic reaction medium, and in the presence of a catalytically effective amount of a catalyst which comprises a cross-linked organic polymeric support, said support having a plurality of catalytically active functional groups covalently coupled thereto, the free valence of said functional groups having the structural formula: ##STR1## The subject process is admirably suited, for example, for the preparation of epoxy resins from the disodium salt of bisphenol A and epichlorohydrin.Type: GrantFiled: August 25, 1981Date of Patent: May 10, 1983Assignee: Rhone-Poulenc IndustriesInventors: Jean-Louis Locatelli, Gerard Soula
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Patent number: 4383103Abstract: Aminoalkoxyamides are provided of the formula: ##STR1## wherein R.sub.4 is selected from H and ##STR2## and R.sub.1, R.sub.2 and R.sub.3 are all independently selected from H or a lower alkyl group having from 1 to about 6 carbon atoms. Also provided are epoxy resin compositions containing such amine-containing compounds as epoxy curing agents and methods for curing epoxy resins where such curing agents may be employed.Type: GrantFiled: February 8, 1982Date of Patent: May 10, 1983Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4376844Abstract: Resin-forming polyepoxides are mixed with polyoxazolidinyl compounds or polymers containing pendant oxazolidinyl groups in which the carbon atom in the 2-position of the heterocyclic ring is substituted with saturated hydrocarbon groups, such as dialkyl, or with an alkylene group forming a saturated ring with the carbon atom in the 2-position of the oxazolidinyl ring to form, in the absence of water, a stable composition which can be stored in closed containers for months without undergoing gelation. When such compositions are spread into films and the films exposed to moisture at ambient temperature, e.g., to ambient air having a relative humidity of at least 20% and temperature of about 15.degree. to 25.degree. C., the polymer serves to react with and cure the polyepoxide.Type: GrantFiled: January 20, 1982Date of Patent: March 15, 1983Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Wayne E. Feely
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Patent number: 4367319Abstract: Auto-crosslinking, cathodically depositable binders which are water-dilutable upon neutralization comprising the reaction product of:(A) 2 moles of a polyepoxy compound with from 2 to 10 epoxy groups per molecule and an epoxy equivalent of from 100 to 1000;(B) 0.1 to 2.0 moles of a diamine, the nitrogen atoms being secondary-secondary or primary-tertiary;(C) from 1 to 10 moles of an alpha,beta-unsaturated monocarboxylic acid; and(D) from 0.5 to 10 moles of dialkanol amine and/or of a monoalkanol monoalkyl amine,whereby the weight ratios of the components are chosen in order that the sum of the epoxy-reactive hydrogen atoms of components (B) through (D) substantially correspond to the number of epoxy groups of component (A), and the binder contains from 0.5 to 2.5 basic nitrogen atoms and from 0.5 to 2.5 polymerizable double bonds per 1000 molecular weight units.Type: GrantFiled: December 15, 1980Date of Patent: January 4, 1983Assignee: Vianova Kunstharz, A.G.Inventors: Georg Pampouchidis, Helmut Honig
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Patent number: 4366274Abstract: Auto-crosslinkable, cathodically depositable aqueous coating compositions which are the reaction product of 2 moles of a diepoxide, 1 mole of a secondary-secondary or primary-tertiary diamine, 0-1 moles of a saturated and/or unsaturated monocarboxylic acid, and 2-1 moles of a secondary amine with optional subsequent partial or total reaction of the hydroxy groups of the reaction product with an alpha,beta-unsaturated monoisocyanate. The binders are rendered water-soluble by neutralization with inorganic and/or organic acids. The binders are capable of being neutralized with low levels of neutralizing acids to provide a component of a coating composition which will cure at low temperatures to give films having excellent surface qualities.Type: GrantFiled: December 15, 1980Date of Patent: December 28, 1982Assignee: Vianova Kunstharz, A.G.Inventors: Georg Pampouchidis, Helmut Honig
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Patent number: 4362856Abstract: Poly-(2-aminoalkyl)polyamine compounds are provided having the following formula: ##STR1## wherein: n is an integer of from 2 to about 12;R.sub.1 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms;R.sub.2 and R.sub.3 are each independently selected from H and a lower alkyl group containing from 1 to about 6 carbon atoms;R.sub.4 is selected from H and ##STR2## and R.sub.5 is selected from an amine terminated polyol moiety having a molecular weight of from about 150 to about 5,000, from about 2 to about 80 ether linkages, and a valence of from about 2 to about 12.Type: GrantFiled: September 16, 1981Date of Patent: December 7, 1982Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4360649Abstract: A curable resin composition comprising an epoxy resin, a hardener and an epoxy compound-dialkylamine adduct as a latent hardener. The composition is excellent in storage stability at ambient temperatures and rapidly curable under heating conditions, and is usable as adhesives, paints, molding materials, casting materials and so on.Type: GrantFiled: April 15, 1981Date of Patent: November 23, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Kunimasa Kamio, Koichi Okuno, Satoru Haraguchi, Hiroyuki Yamaguchi, Koichi Ohashi
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Patent number: 4352919Abstract: Aminoalkoxypentaerythritol compounds are provided having the following formula: ##STR1## where R.sub.1, R.sub.2, and R.sub.3 are independently selected from H and ##STR2## where R.sub.4 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms.Type: GrantFiled: February 2, 1981Date of Patent: October 5, 1982Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Calvin D. Welch
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Patent number: 4352920Abstract: Epoxy resin compositions are provided containing aminoalkoxy compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from H and ##STR2## and R.sub.3, R.sub.4 and R.sub.5 are all independently selected from H and a lower alkyl group having from 1 to about 6 carbon atoms. Also provided are methods for curing epoxy resins where aminoalkoxy curing agents may be employed.Type: GrantFiled: February 2, 1981Date of Patent: October 5, 1982Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4352913Abstract: (Dimethylaminoalkyl)carboxylic and -carbamic acid esters and (dimethylaminoalkyl) ethers and ureas are compounds which are especially suitable for use as amine curing agents for polyepoxide compounds. They impart longer curing times to the curable mixtures and thus good processing properties, especially when the mixtures are used as adhesives. In addition, the mechanical properties are often improved. Further, these compounds afford advantages when used as curing agents on account of their low volatility.Type: GrantFiled: August 21, 1981Date of Patent: October 5, 1982Assignee: Ciba-Geigy CorporationInventors: Helmut Zondler, Roland Moser
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Patent number: 4352921Abstract: Aminoalkoxyhexane compounds are provided having the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are independently selected from H and ##STR2## wherein R.sub.6 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms.Type: GrantFiled: February 2, 1981Date of Patent: October 5, 1982Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Calvin D. Welch
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Patent number: 4351934Abstract: Novel epoxy resin compositions are provided, comprising an epoxy resin and at least one aminoalkoxypropane of the formula: ##STR1## where R.sub.1, and R.sub.2 are independently selected from H and ##STR2## where R.sub.3 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms.Type: GrantFiled: February 2, 1981Date of Patent: September 28, 1982Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Calvin D. Welch
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Patent number: 4340717Abstract: Nitrogen-containing compounds are provided which are selected from compounds having the following formula: ##STR1## wherein X is selected from OH and NH.sub.2, R.sub.1 is selected from --CH.dbd.CH.sub.2 and --C.sub.2 H.sub.5, and R.sub.2 is selected from --NH.sub.2 and: ##STR2## where R.sub.1 has the value indicated above.Type: GrantFiled: March 12, 1981Date of Patent: July 20, 1982Assignee: Milliken Research CorporationInventor: Edward W. Kluger
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Patent number: 4339369Abstract: Tertiary amine terminated resinous compositions are prepared by reacting a molar excess of a polyepoxide compound with a dihydric phenol in a large excess of a monoamine which contains one tertiary amine group and one primary hydroxyl group. The resinous composition can be salted with an acid and can be dissolved or dispersed in water. The aqueous dispersions or solutions can be formulated into primer coatings for metal objects.Type: GrantFiled: April 23, 1981Date of Patent: July 13, 1982Assignee: Celanese CorporationInventors: Darrell D. Hicks, David A. Shimp
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Patent number: 4330644Abstract: The present invention is directed to a curable composition comprising (1) a solid epoxy composition prepared by reacting (a) a solid epoxy resin prepared by reacting a normally liquid epoxy resin with a polyhydric phenol in the presence of an etherification catalyst with (b) a small amount of tris(hydroxymethyl) aminomethane and (2) at least one epoxy curing agent.Type: GrantFiled: April 3, 1981Date of Patent: May 18, 1982Assignee: Shell Oil CompanyInventor: Roy A. Allen
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Patent number: 4330660Abstract: Nitrogen-containing compounds are provided having the following formula: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently selected from H and ##STR2## wherein R.sub.4 and R.sub.5 are each independently selected from H and a lower alkyl group having from 1 to about 4 carbon atoms.Type: GrantFiled: January 16, 1981Date of Patent: May 18, 1982Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Tien-Kuei Su
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Patent number: 4326050Abstract: Compounds typified by N,N'-polyoxyalkylene bis (pyrrolidinone-3-carboxylic acid) are useful as epoxy curing accelerators. Salts thereof, including alkali metal salts, are curing agents for isocyanurate foams.Type: GrantFiled: April 1, 1981Date of Patent: April 20, 1982Assignee: Texaco Development CorporationInventors: Heinz Schulze, Robert L. Zimmerman, Harold G. Waddill
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Patent number: 4316003Abstract: An adduct suitable for curing epoxy resins, particularly in water-borne systems, comprises first reacting an epoxy resin, preferably a saturated epoxy resin, with a primary monoamine and then reacting the resulting condensate with a polyfunctional amine.Type: GrantFiled: October 23, 1980Date of Patent: February 16, 1982Assignee: Shell Oil CompanyInventors: Mark F. Dante, Roy A. Allen
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Patent number: 4310695Abstract: Stable adducts suitable for curing epoxy resins are prepared by reacting a saturated epoxy resin with an excess of an amine and then reacting resulting epoxy-amine condensate with a base, preferably a strong base such as potassium or sodium hydroxide to remove at least 75% of the chlorine present in the condensate.Type: GrantFiled: November 17, 1980Date of Patent: January 12, 1982Assignee: Shell Oil CompanyInventor: Mark F. Dante
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Patent number: 4308085Abstract: High molecular linear, thermoplastic, epoxide-amine-adducts containing the structural segment ##STR1## are prepared by a solvent-free reaction of equivalent amounts at 20 to 200.degree. C. of N,N'-bis(aralkyl) diamines (for example, N,N'-dibenzyl-ethylenediamine, N,N'-dibenzyl-p-xylylenediamine, N,N'-dibenzyl-4,4'-diamino-diphenylmethane, N,N'-dibenzyl-3,6-dioxa-octanediamine-1,8) with diepoxides (for example, 2,2-bis(4-glycidyloxyphenyl)propane). The polyadducts are soluble and may be processed by thermoplastic methods. The polyaddition process may be conducted for the forming of shaped objects in a form-shaping vessel, for the production of coatings directly upon the surface to be coated and also in the presence of inserted materials and has, due to these characteristics, the nature of a casting system.Type: GrantFiled: July 28, 1980Date of Patent: December 29, 1981Assignee: Jenoptik Jena GmbHInventors: Hans-Heinrich Horhold, Dieter Klemm, Klaus Bellstedt, Ludwig Haase, Joachim Klee, Klaus Schubert, Helmut Wachs, Rolf Martin
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Patent number: 4308356Abstract: Resin-forming polyepoxides are mixed with polyoxazolidinyl compounds or polymers containing pendant oxazolidinyl groups in which the carbon atom in the 2-position of the heterocyclic ring is substituted with saturated hydrocarbon groups, such as dialkyl, or with an alkylene group forming a saturated ring with the carbon atom in the 2-position of the oxazolidinyl ring to form, in the absence of water, a stable composition which can be stored in closed containers for months without undergoing gelation. When such compositions are spread into films and the films exposed to moisture at ambient temperature, e.g., to ambient air having a relative humidity of at least 20% and temperature of about 15.degree. to 25.degree. C., the polymer serves to react with and cure the polyepoxide.Type: GrantFiled: January 30, 1980Date of Patent: December 29, 1981Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Wayne E. Feely
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Patent number: 4304889Abstract: A solvent resistant epoxy resin composition comprises a vicinal polyepoxide, an aromatic polyamine and a condensation product of a polyoxyalkylenediamine of about 400 molecular weight or below with at least two moles of maleic anhydride.Type: GrantFiled: July 11, 1980Date of Patent: December 8, 1981Assignee: Texaco Inc.Inventors: Harold G. Waddill, Heinz Schulze
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Patent number: 4296231Abstract: The use of compounds of the formula ##STR1## in which m is a number from 3 to 10, X is a grouping of the formula in which R is an alkyl having 4 to 10 C atoms or a phenyl which is unsubstituted or substituted by chlorine, bromine or alkyl or alkoxy each having 1 to 3 C atoms, and Y is a hydrogen atom or has the meaning defined for X, which are obtained by adding on 1 or 2 mols of an aliphatic or aromatic monoglycidyl ether to 1 mol of a dimethylaminoalkylamine, as a curing catalyst for epoxide resins or as a curing accelerator in curable mixtures consisting of epoxide resins and polycarboxylic anhydrides or polyhydric phenols.Type: GrantFiled: May 1, 1980Date of Patent: October 20, 1981Assignee: Ciba-Geigy CorporationInventors: Ferdinand Gutekunst, Rolf Schmid
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Patent number: 4284746Abstract: An epoxy resin composition which comprises (1) an epoxy resin having at least two epoxy groups per molecule and (2) an amine having at least one perfluoroalkyl group and at least one primary and/or secondary amino groups per molecule can be readily cured to afford a cured product, which shows excellent water resistance, oil resistance and stainproof property.Type: GrantFiled: October 12, 1979Date of Patent: August 18, 1981Assignee: Daikin Kogyo Co., Ltd.Inventor: Akira Ohmori
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Patent number: 4284755Abstract: N-Substituted aspartic acid monoesters of the formula ##STR1## wherein for example R.sub.1 is an alkyl group having 1 to 12 C atoms, a cyclohexyl, phenyl, tolyl or benzyl group, R.sub.2 is an alkyl group having 3 or 4 C atoms, or a cyclohexyl, phenyl, tolyl or methoxyphenyl group, and x is 2 or 3, are obtained by adding, by means of an addition reaction, to 1 mol of a maleic acid monoester of the formula ##STR2## 1 mol of an amine of the formulaH.sub.2 N--(CH.sub.2 ).sub.x NH--R.sub.2in the presence of a tertiary amine. The novel N-substituted aspartic acid monoesters are valuable curing agents for epoxide resins, and are particularly suitable for producing storage-stable B-stage resins.Type: GrantFiled: April 30, 1980Date of Patent: August 18, 1981Assignee: Ciba-Geigy CorporationInventors: Friedrich Lohse, Friedrich Stockinger, Sameer H. Eldin
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Patent number: 4284729Abstract: A process is provided for coloring thermosetting resins, made by polyaddition reaction of a nucleophile with an electrophile, with a polymeric liquid reactive coloring agent suitable for incorporation in the resin with the formation of covalent bonds, said coloring agent having the formula:R-(polymeric constituent-X).sub.nwherein R is an organic dyestuff radical; the polymeric constituent is selected from polyalkylene oxides and copolymers of polyalkylene oxides in which the alkylene moiety of the polymeric constituent contains 2 or more carbon atoms and such polyeric constituent has a molecular weight of from about 44 to about 1500; and n is an integer of from 1 to about 6; and X is selected from --OH, --NH.sub.2 and --SH, said coloring agent being added in an amount sufficient to provide coloration of said thermosetting resin.Type: GrantFiled: March 31, 1980Date of Patent: August 18, 1981Assignee: Milliken Research CorporationInventors: John P. Cross, George H. Britton, Jr.
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Patent number: 4281199Abstract: Polyamines are prepared by first reacting a polyoxyalkylene polyol having one to eight active hydrogen sites with an epihalohydrin. The resulting polyether is, then, reacted with an amine to replace the chlorine atoms with amine functions. The polyamines hereof are useful as intermediates for preparing cationic polyelectrolytes, such as drainage aids and the like.Type: GrantFiled: September 24, 1979Date of Patent: July 28, 1981Assignee: BASF Wyandotte CorporationInventor: William K. Langdon
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Patent number: 4273915Abstract: The invention provides a novel process for the preparation of glycidyl polyethers of polyphenols. The process comprises reacting at least one alkali metal salt of a polyphenol with at least one 2,3-epoxy-1-haloalkane in an anhydrous and essentially aprotic medium, in the presence of a compound of the formulaN[CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ]3wherein n is an integer of from 0 to 10 inclusive; R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be the same or different, are each a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms; R.sub.5 is a hydrogen atom, an alkyl radical having 1 to 12 carbon atoms, a cycloalkyl radical having 3 to 12 carbon atoms, a phenyl radical, a ##STR1## radical or a ##STR2## radical; and m is an integer from 1 to 12 inclusive. The process is especially useful in the preparation of glycicyl polyethers of bisphenol A.Type: GrantFiled: February 29, 1980Date of Patent: June 16, 1981Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Jean-Louis Locatelli
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Patent number: 4269879Abstract: The invention relates to a low-viscosity, solvent-free epoxy-based coating composition consisting essentially of:(a) an epoxy fraction consisting of polyphenol epoxy resins and mixtures thereof; and(b) a curing fraction consisting essentially of:(1) a non-volatile, aromatic extender selected from the group consisting of coal tar, distillates of coke and petroleum with boiling points above about 200.degree. C., and mixtures thereof;(2) an amine curing agent having a molecular weight of about 200-600 selected from the group consisting of:(i) cycloaliphatic diamines having a single amine group directly attached to a single ring structure and the other amine group directly attached to a carbon atom in an aliphatic chain or to a second ring structure;(ii) polyamines having polyaliphatic oxide back-bones; and,(iii) mixtures thereof; and,(3) a curing accelerator selected from the group consisting of tertiary amines.Type: GrantFiled: April 20, 1979Date of Patent: May 26, 1981Assignee: The Dampney CompanyInventor: Murray L. Davis
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Patent number: 4268656Abstract: A N-substituted piperazine or N-substituted homopiperazine adduct with a polyepoxide is used as a co-curing agent in epoxy resin systems containing a polyepoxide and a known curing agent such as dicyandiamide, a carboxylic acid anhydride, or a dihydrazide. The preferred adducts have a ratio of epoxy groups to secondary amino groups of between 1.2:1 and 3:1. The preferred polyepoxides are polyglycidyl ethers of 4,4'-isopropylidenediphenol (bisphenol A). Suitable adducts are prepared from N-methyl-, N-(2-hydroxyethyl)-, N-octyl-, N-phenyl- and N-benzyl piperazine and N-methyl homopiperazine.Type: GrantFiled: January 16, 1980Date of Patent: May 19, 1981Assignee: National Starch and Chemical CorporationInventors: Dilip K. Ray-Chaudhuri, Wen B. Chiao, Jules E. Schoenberg
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Patent number: 4263162Abstract: Hardeners for polyepoxides containing more than one, 1,2-epoxide group per molecule comprising a cyanoethylated polyamide amine containing free secondary or primary or secondary and primary amino groups, said cyanoethylated poly-amide amine is a reaction product of polyadded units of(A) 1 mole of a polyamine corresponding to the formula: ##STR1## in which p=0, n=2 or 3, m=0 to 6 and X=NH.sub.2, or p=1, n=2 or 3, m=0 and X=H,(B) from 0.5 to 2.3 moles of a saturated lactam, and(C) from 0.4 to 2.8 moles of acrylonitrile, methacrylonitrile or mixtures thereof.The hardener may be additionally modified with from 0.01 to 1.8 moles of a 1,2-alkylene oxide containing from 2 to 4 carbon atoms or with from 0.001 to 0.3 moles of a carboxylic acid or with the 1,2-alkylene oxide and the carboxylic acid in the quantities indicated, based in each case on 1 mole of the polyamine.Type: GrantFiled: December 10, 1979Date of Patent: April 21, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Hermann Gruber, Wolfgang Wellner, Karl Leiritz
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Patent number: 4247659Abstract: Water soluble epoxy ester copolymers adapted for sanitary can use comprise an hydroxy functional epoxy ester of a polyepoxide having an average molecular weight of about 300 to about 1100 and a 1,2-epoxy equivalency of about 1.4 to about 2.0, esterified with an at least approximately stoichiometric proportion, based on epoxide functionality, of monocarboxylic acid selected from benzoic acid, C.sub.1 -C.sub.8 alkyl substituted benzoic acid, and C.sub.6 -C.sub.10 alkanoic acid, the esterification reaction being continued to provide an acid number of less than 20, this hydroxy functional epoxy ester is polyesterified with from 1.Type: GrantFiled: March 9, 1979Date of Patent: January 27, 1981Assignee: DeSoto, Inc.Inventors: Kazys Sekmakas, Raj Shah
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Patent number: 4226968Abstract: A method of producing furan-epoxy powder-like binder comprising reacting the product of the polycondensation of epichlorohydrin with diphenylpropane (100 weight parts) with a ketone containing a furfurylidene group (33-200 weight parts) and a nitrogen-containing compound (8-100 weight parts). As examples of the ketone containing a furfurylidene group monofurfurylideneacetone, difurfurylideneacetone, difurfurylidenecyclohexanone, a mixture of monofurfurylideneacetone with difurfurylideneacetone in a ratio (weight parts from 1:1 to 1.4:1; 1,9-di-(.alpha.-furyl)nonanetetracene-1,3,6,8-one-5 or 1,5 -di-(.alpha.-furyl)-2,4-dimethylpentadiene-1, 4-one-3 may be mentioned. Triethanolamine, 3-methyl-5-furylpyrazoline, trifurylimidazoline, hexamethylenediamine, and low molecular polyamides with molecular weight of 2000-10000 or polyethylenepolyamine with molecular weight of 1000 are used as a nitrogen-containing compound. The reaction is performed at 130.degree.-200.degree. C.Type: GrantFiled: June 6, 1978Date of Patent: October 7, 1980Inventors: Gennady D. Varlamov, Ildgam A. Bekbulatov, Shavkat Madaliev, Juldash Mamatov, Alexandra V. Proshkina, Svetlana N. Ubiennykh
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Patent number: 4226969Abstract: A threadlocking composition for mating threaded fasteners utilizes an epoxy resin system with a component adapted to effect dispersion of lubricants or other organic films on the mating threaded surfaces to thereby improve the threadlocking capabilities thereof without requiring pretreatment. The threadlocking composition comprises an epoxy resin, an amine hardener therefor and 1-25 percent of an aminoalcohol compound which is soluble in the resin/hardener system and wherein the amine and hydroxyl groups are disposed on a carbon chain and on different carbon atoms of that chain. In using the composition, it is placed upon the threads of at least one of the cooperating members which are then assembled and allowed to remain so assembled to produce curing of the epoxy composition. Pretreatment of the fastener surfaces is not required. At the end of three hours, this results in an increase in the torque required for disassembly to a level equal to at least 75 percent of the torque required for assembly.Type: GrantFiled: February 8, 1979Date of Patent: October 7, 1980Assignee: Allied Products CorporationInventors: Charles R. Watson, Jr., Mary A. Eichner
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Patent number: 4219508Abstract: This invention relates to an improved process for the preparation of a mixture of various low molecular weight hydroxyaldehydes, hydroxyketones and polyhydric alcohols by the condensation of formaldehyde with itself. The essential feature of the improvement is that unpurified synthesis gases of the kind obtained from the large scale industrial production of formaldehyde can be used directly as the source of formaldehyde.Type: GrantFiled: August 30, 1977Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventor: Kuno Wagner
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Patent number: 4218377Abstract: Novel carboxylic acid metal salt/amine complexes of the formula(A.sup..crclbar.).sub.2 Me.sup.2+ .multidot.NH.sub.2 --R.sub.1 --NH.sub.2in which A is the anion of cyanoacetic acid, pyrrolidonecarboxylic acid, maleimidylcarboxylic acid, succinylimidylcarboxylic acid, benzenesulphonic acid or toluenesulphonic acid or of a methanephosphonic acid monoester or benzenephosphonic acid monoester, Me.sup.2+ is a divalent metal cation and R.sub.1 is a long-chain polyoxyalkylene radical, are obtained by reacting 1 mol of a carboxylic acid metal salt of the formula(A.sup..crclbar.).sub.2 Me.sup.2+with 1 mol of a diamine of the formulaH.sub.2 N--R.sub.1 --NH.sub.2in a polar organic solvent and in the temperature range of 25.degree. to 200.degree. C. to give the complex compounds of the formula.The novel complex compounds are valuable curing agents for epoxide resins and in mixtures with epoxide resins have an advantageous storage stability.Type: GrantFiled: October 31, 1978Date of Patent: August 19, 1980Assignee: Ciba-Geigy CorporationInventors: Friedrich Stockinger, Sameer H. Eldin, Friedrich Lohse
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Patent number: 4197389Abstract: A hardening agent for an aqueous epoxy resin composition comprising a reaction product of (a) at least one polyepoxide compound, (b) at least one polyalkylene polyether polyol and (c) at least one compound selected from the group consisting of aliphatic, cycloaliphatic and heterocyclic polyamine and wherein component (c) additionally may be reacted with (d) an unsaturated compound before or after the reaction with the adduct of components (a) and (b), process for preparing said hardening agent and hardenable film forming coating compositions comprising as essential ingredients said hardening agent, at least one polyfunctional epoxy compound (a) and water.Type: GrantFiled: July 12, 1978Date of Patent: April 8, 1980Assignee: Hoechst AktiengesellschaftInventors: Wilhelm Becker, Horst Karasmann
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Patent number: 4195153Abstract: A novel epoxy resin curing accelerator comprises a mixture of N-aminoethylpiperazine (AEP) and triethanolamine (TEA). The resins comprise a vicinal polyepoxide, a curing agent, and an amount of AEP/TEA mixture effective for accelerating the cure of the polyepoxide. The accelerator combination is synergistic for accelerating the curing of an epoxy resin cured with an amine at ambient or elevated temperatures. The epoxy resin products are useful in protective coatings, adhesives, seamless and terrazzo flooring, castings, laminates, and in grouting, potting, encapsulating, caulking and sealing compositions.Type: GrantFiled: October 19, 1978Date of Patent: March 25, 1980Assignee: Texaco Development CorporationInventor: Harold G. Waddill
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Patent number: 4193905Abstract: Curable mixtures comprising a polyepoxide compound having on average more than one epoxide group per molecule and a 1,3-diaminopropane of the formula ##STR1## wherein R.sup.1 denotes hydrogen and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each denote an alkyl having 1 to 12 C atoms, a phenyl or a heterocyclic 5-membered or 6-membered radical, or wherein R.sup.1 and R.sup.2 together with the C atom in the .alpha.-position of the propylenediamine from a substituted or unsubstituted aliphatic 5-membered or 6-membered ring having at most 12 C atoms and R.sup.3 and R.sup.4 together with the two C atoms in the .alpha.-position and the .beta.-position of the propylenediamine form a substituted or unsubstituted aliphatic or N-heterocyclic 5-membered or 6-membered ring having at most 12 C atoms, said mixtures containing 0.5 to 1.5 equivalents of active hydrogen atoms, bonded to nitrogen, in the 1,3-diaminopropane per 1 equivalent of epoxide groups in the epoxide compound.Type: GrantFiled: December 2, 1977Date of Patent: March 18, 1980Assignee: Ciba-Geigy CorporationInventors: Thaddeus Audykowski, Roland Moser
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Patent number: 4191836Abstract: Bis-anthranilates of the formula ##STR1## or mixtures thereof, in which, in the formula, m and n are each 0 or a number from 1 to 5 and the sum of m and n must be at least 1, y is 0 or 1 and X is an alkylene radical having 1 to 8 C atoms, para- or meta-phenylene or para-cyclohexylene.The novel compounds are valuable chain extenders and crosslinking agents for the production of polyurethanes and polyurea resins and are also suitable as curing agents for epoxide resins.Type: GrantFiled: December 4, 1978Date of Patent: March 4, 1980Assignee: Ciba-Geigy CorporationInventors: Jurgen Habermeier, Roland Moser
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Patent number: 4190719Abstract: An epoxy resin curing agent comprising a compound represented by the formula (I): ##STR1## wherein k, m and n, which may be the same or different, each is an integer of 1 to 6, and l is an integer of 0 to 6, and/or a modified product thereof, a curable epoxy resin composition comprising an epoxy resin and the epoxy resin curing agent represented by the formula (I), and a cured product obtained from the epoxy resin composition.Type: GrantFiled: July 5, 1978Date of Patent: February 26, 1980Assignee: Mitsubishi Petrochemical Company LimitedInventors: Hiroshi Samejima, Kaoru Kanayama
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Patent number: 4189564Abstract: A novel epoxy resin curing accelerator comprises a mixture of piperazine, N-aminoethylpiperazine (AEP) and triethanolamine (TEA). The resins comprise a vicinal polyepoxide, a curing agent, and an amount of piperazine, AEP and TEA mixture effective for accelerating the cure of the polyepoxide. The accelerator combination is synergistic for accelerating the curing of an epoxy resin cured with an amine at ambient or elevated temperatures. The epoxy resin products are useful in protective coatings, adhesives, seamless and terrazzo flooring, castings, laminates, and in grouting, potting, encapsulating, caulking and sealing compositions.Type: GrantFiled: October 19, 1978Date of Patent: February 19, 1980Assignee: Texaco Development CorporationInventor: Harold G. Waddill
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Patent number: 4188474Abstract: A novel epoxy resin curing accelerator comprises oligomeric poly(ethylenepiperazine). The resins comprise a vicinal polyepoxide, a curing agent, and an amount of oligomeric poly(ethylenepiperazine) effective for accelerating the cure of the polyepoxide.Type: GrantFiled: September 11, 1978Date of Patent: February 12, 1980Assignee: Texaco Development CorporationInventors: Harold G. Waddill, Philip H. Moss
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Patent number: RE30264Abstract: Polymeric products comprising the acidified reaction product of an organic polyepoxide and a polyamine containing at least two tertiary amine groups are disclosed. The polyamine and the organic polyepoxide are reacted with one another under conditions to form an internally ionized, quaternary ammonium salt group-containing polymer which has a high molecular weight, but relatively low equivalent weight. The polyamine is formed by reacting an organic polyisocyanate .[.or organic polycarboxylic acid.]. with an active hydrogen-containing tertiary amine. The reaction product is acidified to form the quaternary ammonium salt groups. Preparing the polyamine in this manner gives one wide latitude in determining the final structure of the polyamine. In effect, one can "tailor make" the polyamine by appropriate selection of reactants and exert a great measure of control over the properties of the final polymeric product.Type: GrantFiled: January 22, 1979Date of Patent: April 29, 1980Assignee: PPG Industries, Inc.Inventor: Karl F. Schimmel