Nitrogen-containing Reactant Contains The -n-c(=o)-n- Group Patents (Class 528/164)
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Patent number: 8759471Abstract: The invention relates a mixture of a urethane-aldehyde resin UA prepared by condensation of an aldehyde A1 and an alkyl urethane U, and of a novolak PA, to a process for the preparation of the said mixture, and a method of use thereof as adhesion promoter in rubber goods.Type: GrantFiled: May 19, 2010Date of Patent: June 24, 2014Assignee: Allnex Germany GmbHInventors: Ralph Schäfer, Peter Ziegler
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Publication number: 20110306735Abstract: The invention relates to a hydroxy-aromatic resin, prepared by bringing together and letting react a hydroxy-aromatic compound of formula (I) and an alkanol hemiacetal compound of formula (II). Formula (I) is: wherein R1, R2, R3, R4 and R5 may be the same or may be different and are H, OH, a C1-C20 alkyl group, or an oligomeric or polymeric system, whereby at least one of the set consisting of R1, R3, and R5 is H, Formula (II) is: wherein R6 is a C1-C12 alkyl group, aryl group, aralkyl group or cycloalkyl group and wherein R12 is H, a C1-C12 alkyl group, aryl group, aralkyl group or cycloalkyl group. The invention further relates to use of the resin in adhesives, laminates, and coatings.Type: ApplicationFiled: August 24, 2011Publication date: December 15, 2011Applicant: DSM IP Assets B.V.Inventor: Rudolfus Antonius Theodorus Maria VAN BENTHEM
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Patent number: 7989575Abstract: A composition is disclosed, which comprises a hydroxyaromatic-aldehyde resole resin comprising an aldehyde and a hydroxyaromatic compound, modified with a urea-aldehyde condensate. The hydroxyaromatic-aldehyde resole resin is prepared without ammonia or a primary amine and the composition does not contain a triazone or a substituted triazone compound. The composition has improved premix stability, improved cure efficiency, comparable tensile strength, and lower volatiles than the hydroxyaromatic-aldehyde resole resin unmodified with a urea-aldehyde condensate. Also disclosed are articles prepared therefrom.Type: GrantFiled: December 14, 2007Date of Patent: August 2, 2011Assignee: Momentive Specialty Chemicals Inc.Inventor: Stephen W. Arbuckle
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Patent number: 7910667Abstract: A heat curable epoxy composition comprising the contact product of an epoxy resin, an epoxy curing agent and an accelerator for the epoxy curing agent, the curing agent or the accelerator comprising the reaction product of (a) a phenolic resin and (b) a urea compound which is the reaction product of an isocyanate and an alkylated polyalkylenepolyamine having one primary or secondary amine and at least two tertiary amines of the general formula: where R1, R2, R3, R4 and R5 independently represent hydrogen, methyl or ethyl; n and m are independently integers from 1 to 6 and; X is an integer from 1 to 10.Type: GrantFiled: September 11, 2009Date of Patent: March 22, 2011Assignee: Air Products and Chemicals, Inc.Inventors: Gamini Ananda Vedage, Atteye Houssein Abdourazak
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Patent number: 7511114Abstract: Colored aromatic polycarbonate resin compositions are prepared by dispersing a colorant (b) selected from phthalocyanine-based compounds, anthraquinone-based compounds and ultramarine blue in a polyalkyleneglycol compound (c) having a number-average molecular weight of 62 to 4000 of formula (2): HO—[—CHR1—CHR2—]m—OH??(2) where R1, R2, R3 and R4 are independently hydrogen atoms or alkyl groups, and m is not less than 1. The dispersion is added to an aromatic polycarbonate resin (a) kept in a molten state which has a viscosity-average molecular weight of not less than 16000 and contains a branched constitutional unit of formula (1): in an amount of 0.3 to 0.95 mol % where X is a single bond, an alkylene group having 1 to 8 carbon atoms, an alkylidene group having 2 to 8 carbon atoms, a cycloalkylene group having 5 to 15 carbon atoms, a cycloalkylidene group having 5 to 15 carbon atoms, or a divalent connecting group —O—, —S—, —CO—, —SO— and —SO2—.Type: GrantFiled: November 28, 2006Date of Patent: March 31, 2009Assignee: Mitsubishi Chemical CorporationInventors: Masaaki Miyamoto, Takao Tayama, Kiyoji Kuma, Eiji Fujimoto
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Patent number: 7323534Abstract: A composition is disclosed, which comprises a hydroxyaromatic-aldehyde resole resin comprising an aldehyde and a hydroxyaromatic compound, modified with a urea-aldehyde condensate. The composition has improved premix stability, improved cure efficiency, comparable tensile strength, and lower volatiles than the hydroxyaromatic-aldehyde resole resin unmodified with a urea-aldehyde condensate. Also disclosed are articles prepared therefrom.Type: GrantFiled: October 12, 2005Date of Patent: January 29, 2008Assignee: Hexion Specialty Chemicals, Inc.Inventor: Stephen W. Arbuckle
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Patent number: 7084233Abstract: A subject for the invention is to provide a branched aromatic polycarbonate which is excellent in hue and in melt characteristics such as melt strength. The invention provides a branched aromatic polycarbonate having a viscosity-average molecular weight of 16,000 or higher obtained by the transesterification method, characterized in that the ratio of the weight-average molecular weight (Mw) to number-average molecular weight (Mn) as measured by gel permeation chromatography and calculated for standard polystyrene (Mw/Mn) is in the range of from 2.8 to 4.5 and that the proportion of the number of moles of all structural units yielded by a rearrangement reaction in the course of melt polymerization reaction to 1 mol of structural units having the framework of an aromatic dihydroxy compound used as a starting material is higher than 0.3 mol % and not higher than 0.95 mol.Type: GrantFiled: March 31, 2004Date of Patent: August 1, 2006Assignees: Mitsubishi Chemical Corporation, Mitsubishi Engineering-Plastics CorporationInventors: Masaaki Miyamoto, Takao Tayama, Hiroshi Nakano
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Patent number: 6916505Abstract: A water-soluble composition including a water soluble polyamine adduct which is a reaction product of: (a) an alkoxy group modified polyepoxide resin containing an average of at least 1.5 epoxide groups per molecule; and (b) a Mannich base polyamine. The Mannich base polyamine is a reaction product of a polyamine containing at least two amino groups with a N-Mannich condensate prepared from a reaction of a phenolic compound, an aldehyde, and a secondary amine wherein the secondary amine of the N-Mannich condensate is replaced by one of the at least two amino groups of the polyamine, and wherein the ratio of the Mannich base polyamine to the alkoxy group modified polyepoxide resin contains an excess of an active amine hydrogen relative to epoxide groups so that the water soluble polyamine adduct has an amine hydrogen equivalent weight of at most 1000 based on solids content.Type: GrantFiled: March 4, 2003Date of Patent: July 12, 2005Assignee: Air Products and Chemicals, Inc.Inventors: William R. Raymond, Michael Cook
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Patent number: 6706809Abstract: Infinitely water soluble, storage stable, low molecular weight, amine-modified resins/binders (e.g., phenol-formaldehyde resole resins and binders made therefrom) are used to produce low odor fiberglass products, such as fiberglass insulation for automobile headliners and room dividers. The cured, bonded fiberglass products have low TMA (trimethylamine) emission because the free formaldehyde in the resin has been scavenged with melamine, which resists thermal decomposition, and because the binder contains a relatively low urea content, which is a TMA contributor. The resole resin production process includes adding two different formaldehyde scavengers (e.g., melamine and urea) to produce a modified phenol-formaldehyde resole resin. This resole resin is produced into a binder by mixing with water, optionally in the presence of a latent acid catalyst (e.g., an ammonium salt of a strong acid).Type: GrantFiled: November 21, 2001Date of Patent: March 16, 2004Assignee: Georgia-Pacific Resins, Inc.Inventors: Kim Tutin, W. Hayes Ingram, Mary L. Epling, Kurt D. Gabrielson, James T. Wright, Carl R. White
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Patent number: 6699958Abstract: The present invention is directed to compositions and a process leading to colorless or light colored aqueous phicinol-formaldelhyde resoles. Unlike previous technologies, these compositions lead to clear storage stable fast curing, high molecular weight resins. These materials are also capable of producing composite wood panels with superior water absorption and thickness swell test results when soaked in water. The invention essentially consists of an aqueous copolymer of phenol, formaldehyde, and a phenolic carboxylate (e.g. salicylic acid). Methylol phenols are formed under alkaline conditions in the presence of metal chelating agents. These are then condensed into a polymer under alkaline, neutral or acidic conditions. The finished aqueous polymer solution is then acidified to the desired pH using a benzoic acid or a phelnol-carboxylic acid.Type: GrantFiled: February 13, 2003Date of Patent: March 2, 2004Assignee: Borden Chemical, Inc.Inventor: William D. Detlefsen
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Patent number: 6657016Abstract: A polyester resin composition comprising 50 equivalents/ton or more of an aromatic ring in the resin and at least one thermosetting resin selected from the group consisting of melamine resin, urea resin, benzoguanamine resin and phenol resin. The aromatic ring in the polyester resin has a phenolic hydroxyl group and at least one of ortho-position and para-position of the aromatic ring to the phenolic hydroxyl group is a hydrogen atom. The resin composition has excellent toughness at ambient temperature and heat resistance.Type: GrantFiled: March 14, 2002Date of Patent: December 2, 2003Assignee: Toyo Boseki Kabushiki KaishaInventor: Takeshi Yatsuka
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Patent number: 6646094Abstract: A phenol-formaldehyde resole resin is prepared using a high level of catalyst at a polymerization temperature of about 63° C. The endpoint, measured by salt water tolerance, is selected so that the resulting resin has a water dilutability of 20:1 at neutral pH after storage for three weeks at a temperature of about 13° C., with a free phenol level of no more than 0.50 percent.Type: GrantFiled: December 17, 2001Date of Patent: November 11, 2003Assignees: CertainTeed Corporation, Borden Chemical, Inc.Inventors: Vinay Malhotra, Wayne Walliser, Susan G. Watson, Pierre C. Herault, Domenic Tessari, Philippe Espiard, Serge Tetart, Bruno Malhieuxe
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Patent number: 6541576Abstract: A catalyst curing system or hardener for resorcinolic resins, such as resorcinol-formaldehyde or phenol-resorcinol-formaldehyde resins including methylolurea. The methylolurea may be used in combination with oxazolidine in ratios ranging from 5:95 to 95:, by molar basis. The hardener crosslinks the resins which permits reduction or “fuming” of formaldehyde as well as control of gel times of the resulting adhesive. The hardener of the present invention if of particular utility in adhesives for use in the forest products industry.Type: GrantFiled: August 11, 1998Date of Patent: April 1, 2003Assignee: Borden Chemical, Inc.Inventors: Earl K. Phillips, Arthur J. Garwood, William D. Detlefsen
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Patent number: 5763558Abstract: A process for hardening a composition and a hardenable composition, in wh there are used:at least one novolac resin;at least one hardener of the resin, selected from the group consisting of substituted melamines;at least one compound comprising at least one ##STR1## group, this compound being without methylol group and ether group corresponding to methylol, and/or at least one reagent capable of giving such a compound under the conditions of the hardening.The hardening of the resin is caused by the action of heat.Type: GrantFiled: June 11, 1996Date of Patent: June 9, 1998Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & CieInventors: Brigitte Marie Chauvin, Olivier Durel
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Patent number: 5681916Abstract: Urea-modified, highly reactive phenolic resins useful as center-layer bonding agents in the manufacture of particleboard are provided by condensing phenol and formaldehyde until shortly before gelation takes place such that, after addition of urea, relatively low-alkaline, urea-modified phenolic resins are obtained which my optionally be stored and to which, shortly before processing them into glues for center-layer particles, alkali is added in sufficient quantities to ensure rapid cross-linking of the phenolic resin.Type: GrantFiled: June 29, 1995Date of Patent: October 28, 1997Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Adolf Buschfeld, Matthias Lattekamp, Manfred Gramse, Hans-Jurgen Krezmin
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Patent number: 5629083Abstract: A process for the production of modified phenol-aldehyde resins includes the use of a modifier selected from melamine, urea, and other suitable nonvolatile organic compounds. The phenolic component of the resins preferably includes a difunctional phenolic compound. The inventive resins resist precuring and are particularly useful in blowline blending procedures.Type: GrantFiled: June 7, 1995Date of Patent: May 13, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5623032Abstract: A process for preparing ashless and low-ash phenolic resole resins having no amine odor, and a process for preparing storage-stable mixtures or premix solutions of phenol-formaldehyde resin and urea or unrea-formaldehyde resins. These processes react phenol and formaldehyde in the presence of an effective catalytic amount of a low-volatile and strongly basic tertiary amino alcohol either alone or in combination with an inorganic base.Type: GrantFiled: June 23, 1995Date of Patent: April 22, 1997Assignee: Angus Chemical CompanyInventor: Gaoming Wu
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Patent number: 5621052Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: December 29, 1992Date of Patent: April 15, 1997Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5605986Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: May 23, 1995Date of Patent: February 25, 1997Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5538761Abstract: Emissions of formaldehyde and ammonia from urea-extended alkaline phenol/formaldehyde resole fiberglass binders are sharply reduced by using as a catalyst an emission-reducing effective amount of an acidifying agent which is a hydrolyzable inorganic salt, mineral acid, monomeric carboxylic acid or partial ester of a polycarboxylic acid such that the instantaneous pH of the binder solution is lower than 5.5. Use of the catalysts of the subject process also allow for additional urea-extension without degradation of fiberglass product physical properties. The preferred catalyst is aluminum sulfate in an amount of from 2.0 weight percent to about 4.0 weight percent based on the resin solids.Type: GrantFiled: June 13, 1995Date of Patent: July 23, 1996Assignee: Schuller International, Inc.Inventor: Thomas J. Taylor
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Patent number: 5473012Abstract: A phenolic binder for glass fibers is prepared using an aqueous mixture including a phenol-formaldehyde resole resin, modified with urea in the presence of ammonia. The urea and ammonia are added after the basic mixture including the resole resin has been neutralized. The urea-modified resole resin shows greater stability than urea-modified resins prepared without ammonia.Type: GrantFiled: November 22, 1994Date of Patent: December 5, 1995Assignee: CertainTeed CorporationInventors: Kathleen H. Coventry, David A. Segal, Jacky Joachim
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Patent number: 5368803Abstract: A fibrous resinated panel is provided which when used in a closed environment releases relatively minor amounts of trimethylamines, aldehydes and phenolic compounds into the closed environment. The panel is formed by compressing a fibrous mat impregnated with a thermosetting resin system in a mold cavity defined between an upper and a lower inner mold surface at a temperature between 400.degree. to 600.degree. for 45 to 90 seconds whereby the thermosetting resin is substantially cured and the mat is shaped to conform to a desired contour prior to removing the mat from the mold cavity. The thermosetting resin system used to impregnate the mat includes an essentially aqueous A-stage form resole-melamine composition containing residues of free melamine(s) to free aldehyde(s) to free phenolic compound(s) in a molar equivalent ratio ranging from about 0.2:1.5:1 to about 0.8:3.5:1.Type: GrantFiled: February 12, 1993Date of Patent: November 29, 1994Assignee: United Technologies Automotive, Inc.Inventors: Mark J. Brow, Ronald P. Pitsch
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Patent number: 5340903Abstract: The invention concerns a phenolic resin.The resin is a liquid, contains phenol-formaldehyde, formaldehyde-urea and phenol-formaldehyde-amine condensates, and has a free formaldehyde content of less than 3%, this proportion being expressed as a percentage of the total fluid weight, and a dilutability rate in water which equals or surpasses 1,000%. Furthermore, the resin is stable when heated. Application to less-polluting sizing compositions for mineral fibers; and use of the fibers thus sized for the manufacture of insulating products and soilless cultivation substrates.Type: GrantFiled: August 27, 1993Date of Patent: August 23, 1994Assignee: Isover Saint-GobainInventors: M. Serge Tetart, M. David Segal
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Patent number: 5300562Abstract: A phenolic binder for glass fibers is prepared using an aqueous mixture including a phenol-formaldehyde resole resin, modified with urea in the presence of ammonia. The urea and ammonia are added after the basic mixture including the resole resin has been neutralized. The urea-modified resole resin shows greater stability than urea-modified resins prepared without ammonia.Type: GrantFiled: June 8, 1993Date of Patent: April 5, 1994Assignee: CertainTeed CorporationInventors: Kathleen H. Coventry, David A. Segal
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Patent number: 5270434Abstract: The invention concerns a phenolic resin.The resin is a liquid, contains phenol-formaldehyde, formaldehyde-urea and phenol-formaldehyde-amine condensates, and has a free formaldehyde content of less than 3%, this proportion being expressed as a percentage of the total fluid weight, and a dilutability rate in water which equals or surpasses 1,000%. Furthermore, the resin is stable when heated. Application to less-polluting sizing compositions for mineral fibers; and use of the fibers thus sized for the manufacture of insulating products and soilless cultivation substrates.Type: GrantFiled: November 2, 1992Date of Patent: December 14, 1993Assignee: Isover Saint-GobainInventors: M. Serge Tetart, M. David Segal
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Patent number: 5194331Abstract: The present invention is a fiber comprising cyanato group containing phenolic resin comprising repeating units of the formula: ##STR1## wherein p is 0 or an integer of one or more, q is O or an integer of 1 or more, X is a radical selected from the group consisting of: --CH.sub.2 --, --CO--, --SO.sub.2 --, ##STR2## and R is the same or different and is selected from the group consisting of hydrogen and methyl radicals. The fiber of the present invention can be made a phenolic triazine derived from the cyanato group containing phenolic resin.Type: GrantFiled: September 16, 1991Date of Patent: March 16, 1993Assignee: Allied-Signal Inc.Inventors: Sajal Das, Dusan C. Prevorsek
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Patent number: 5155164Abstract: Products of the condensation of phenolmonosulfonic acids, dihydroxydiphenyl sulfones, urea and formaldehyde can be obtained by(A) preparing a homogeneous reaction mixture in sulfuric acid from the phenolmonosulfonic acid and dihydroxydiphenyl sulfone in the molar ratio of from 3:1 to 10:1, with the proviso that the water content of the mixture is not more than 10% of the total weight of the components, and the mixture contains from 0.3 to 1.5 moles of sulfuric acid per mole of dihydroxydiphenyl sulfone, at from 100.degree. to 180.degree. C.,(B) subsequently, at from 40.degree. to 90.degree. C., carrying out a precondensation with 1 to 2 moles of formaldehyde and 0.5 to 1.5 moles of urea per mole of phenol units present in aqueous medium,(C) partially neutralizing the reaction mixture,(D) adding to the partially neutralized reaction mixture 0 to 0.5 mole of phenol per mole of phenol units present and then 0.1 to 0.8 mole of formaldehyde per mole of phenol units then present,(E) further condensing at from 40.Type: GrantFiled: May 8, 1991Date of Patent: October 13, 1992Assignee: BASF AktiengesellschaftInventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
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Patent number: 5102972Abstract: A class of di-ortho-substituted bismaleimides undergo uncatalyzed Michael addition with polyhydric phenols to afford chain-extended bismaleimides having a significantly wider processing window than the non-extended parent. The fully cured resins show improved fracture toughness, generally have comparable or superior dielectric constant and dielectric loss, and show no degradation in other properties such as resistance to moisture, to methylene chloride, and coefficient of thermal expansion.Type: GrantFiled: July 25, 1990Date of Patent: April 7, 1992Assignee: Allied-Signal Inc.Inventors: Raymond J. Swedo, Joseph J. Zupancic
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Patent number: 5011886Abstract: The inventive concept is to condense the phenol formaldehyde resins to a higher molecular weight than usual so far. Subsequent addition of urea thereto reduces viscosity to normal levels and increases solid content.The added urea does not take part in condensation reaction but partly reacts in the alkaline medium with formaldehyde to methylol urea (in a so called equilibrium reaction), which is formaldehyde donor for the phenol formaldehyde crosslinking reaction during the pressing of the particle board.The present invention relates to a process for producing modified phenolic resin bonding agents, characterized by preparing as known per se phenol-formaldehyde resins with a viscosity of more than 300 mPa.s (at 20.degree. C.Type: GrantFiled: February 26, 1990Date of Patent: April 30, 1991Assignee: Rwe-Dea Aktiengesellschaft fur Mineraloel und ChemieInventors: Adolf Buschfeld, Matthias Lattekamp, Gerd Ripkens, Hans Schittek
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Patent number: 4960826Abstract: The titled compositions are useful binding adhesives, especially, for example, with engineered glass fiber-containing products, and the like. In the A-stage, the compositions are typically exceptionally water soluble and low temperature storage stable. Such compositions can be prepared initially by a procedure in which a resole or the like is copolymerized with free melamine(s) and is conditioned to include acidic stage conditioning. For example, phenol per se, formaldehyde and sodium hydroxide followed by melamine per se and aqueous sulfamic acid solution, with subsequent neutralization, can yield the exceptionally water soluble low temperature storage stable A-stage composition. The C-stage composition is non-punking and can be structurally hard and sound.Type: GrantFiled: February 19, 1988Date of Patent: October 2, 1990Assignee: Borden, Inc.Inventor: Wayne R. Walisser
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Patent number: 4857581Abstract: Cationic paint binders obtained through reaction of substituted ureas with formaldehyde and phenols are described. The substituted ureas are obtained through reaction of an isocyanate compound carrying at least one free, and optionally also blocked, NCO-group with equivalent quantities of a secondary non-aromatic amine. After partial protonation, the binders are used in water-dilutable paints, particularly in cathodically depositable electrodeposition paints.Type: GrantFiled: December 15, 1987Date of Patent: August 15, 1989Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Anton Arzt
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Patent number: 4855394Abstract: Condensates based on substituted ureas, their reaction products with di- and/or polyisocyanates, derivatives of di- and/or polycarboxylic acids or p-substituted phenols and/or their methylol derivatives, their preparation and their use. These condensates each contain two or more cyclic urea units and can be prepared either by reacting primary di- or polyamines with ureas and reacting the product with predominantly CH-acidic aldehydes or by reacting primary amines with isocyanates and reacting the product with predominantly CH-acidic aldehydes in the presence of an acidic catalyst. The said condensates and their reaction products are useful for the preparation of heat-curable coating materials and of binders for cathodic electrocoating.Type: GrantFiled: January 25, 1989Date of Patent: August 8, 1989Assignee: BASF AktiengesellschaftInventors: Ulrich Goeckel, Harro Petersen, Rolf Osterloh, Eberhard Schupp, Werner Loch, Thomas Schwerzel
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Patent number: 4839445Abstract: The present invention relates to a process for producing spherical thermosetting phenolic resin particles having a size of no larger than about 1,000 microns, and the spherical thermosetting phenolic resin particles produced by this process.In accordance with the process of the present invention, a novolak resin, and a nitrogenous basic compound, and, optionally, an aldehyde, are reacted while they are suspended in an aqueous medium in the presence of a suspension stabilizer.The thermosetting phenolic resin produced by the process of the present invention not only displays superior thermal curing characteristics during molding; the cured product fabricated by molding this resin also exhibits good physical properties such as improved mechanical strength and heat resistance. Therefore, the spherical thermosetting phenolic resin particles produced by the process of the present invention can be extensively used as molding materials, binders, adhesives, and in many other applications.Type: GrantFiled: January 6, 1988Date of Patent: June 13, 1989Assignee: Unitika, Ltd.Inventors: Yoshiaki Echigo, Kenichi Sugawara, Mutsunori Yamao, Yoshiyuki Suematu, Keiichi Asami, Tuneyuki Ohsawa
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Patent number: 4757108Abstract: A water soluble phenolic resole-urea composition useful as a binder which remains infinitely water-dilutable and free of sediment after one month of storage at 0.degree. C. and is made by the reaction of urea with the free formaldehyde in a phenolic resole under acid conditions, followed by the further addition of urea at neutral or slightly basic conditions.Type: GrantFiled: June 18, 1986Date of Patent: July 12, 1988Assignee: Borden, Inc.Inventor: Wayne R. Walisser
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Patent number: 4731430Abstract: Phenol resins which are modified with compounds possessing amide and/or imide groups and are based on phenol resol ethers bonded via o,o'-methylene ether groups, and a process for their preparation.The novel modified phenol resol ethers are useful for the preparation of coating systems, in particular as crosslinking agents for cathodic electrocoating binders, and for the preparation of adhesives and rubber assistants.Type: GrantFiled: July 9, 1986Date of Patent: March 15, 1988Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Juergen Nieberle
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Patent number: 4722991Abstract: A terpolymer is prepared from phenol, furfuryl alcohol and formaldehyde wherein a substantial amound of the furfuryl alcohol is catalytically reacted by means of a water soluble multivalent metal salt catalyst, and wherein the reaction is carried out under essentially hydrous conditions.Type: GrantFiled: May 23, 1986Date of Patent: February 2, 1988Assignee: Acme Resin CorporationInventor: David R. Armbruster
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Patent number: 4710406Abstract: A condensation product of phenol, formaldehyde and urea condensed in the presence of a basic catalyst, said condensation product being a liquid and having a free phenol content below 0.5%, a free formaldehyde content below 3%, expressed by weight based on the total weight of liquid, and a dilutability, measured at 20.degree. C., of at least equal to 1000%.Type: GrantFiled: January 20, 1987Date of Patent: December 1, 1987Assignee: Isover Saint-GobainInventors: Roger Fugier, Charles de Goys de Mezerac, Jacky Joachim, Michel Decagny
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Patent number: 4663419Abstract: A condensation product of phenol, formaldehyde and urea condensed in the presence of a basic catalyst, said condensation product being a liquid and having a free phenol content below 0.5%, a free formaldehyde content below 3%, expressed by weight based on the total weight of liquid, and a dilutability, measured at 20.degree. C., of at least equal to 1000%.Type: GrantFiled: November 19, 1984Date of Patent: May 5, 1987Assignee: Isover Saint-GobainInventors: Roger Fugier, Charles D. de Mezerac, Jacky Joachim, Michel Decagny
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Patent number: 4659787Abstract: A new class of epoxy curing agents has been discovered that utilizes the monomer of (a) urea-formaldehyde, (b) phenol modified urea-formaldehyde, or (c) thiourea-formaldehyde as the center of a polyamine molecule. The ether monomers are reacted with conventional aliphatic, cycloaliphatic, and aromatic polyamines to split off alcohol and water-yielding urea-formaldehyde etc., polyamine epoxy curing agents.Type: GrantFiled: November 14, 1985Date of Patent: April 21, 1987Assignee: Chemcrete International PartnershipInventor: Lowell O. Cummings
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Patent number: 4574145Abstract: A new class of epoxy curing agents has been discovered that utilizes the monomer of (a) urea-formaldehyde, (b) phenol modified urea-formaldehyde, or (c) thiourea-formaldehyde as the center of a polyamine molecule. The ether monomers are reacted with conventional aliphatic, cycloaliphatic, and aromatic polyamines to split off alcohol and water-yielding urea-formaldehyde etc., polyamine epoxy curing agents.Type: GrantFiled: September 28, 1984Date of Patent: March 4, 1986Assignee: Chemcrete InternationalInventor: Lowell O. Cummings
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Patent number: 4546168Abstract: A thermosetting resin composition comprising (A) at least one dicyanamide compound and (B) at least one polyvalent imide having one or more unsaturated bonds and, if necessary (C) at least one polymerizable compound of epoxy compounds, phenolic compounds and triallyl isocyanurate compounds, and a prepolymer thereof obtained by subjecting the composition to a preliminary reaction with heating to the B stage can give a cured product having excellent heat resistance of class C and flexibility.Type: GrantFiled: August 9, 1984Date of Patent: October 8, 1985Assignee: Hitachi, Ltd.Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
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Patent number: 4491654Abstract: A water-insoluble curing agent for epoxy resins, made by mixing a major amount by weight of a water-insoluble propylene diamine chosen from the group consisting of the C.sub.8 to C.sub.20 fatty propylene diamines and the C.sub.12 to C.sub.15 ether propylene diamines with a minor amount by weight of a water-soluble polyamine suitable for rapid cure of epoxy resins, mixing the resulting mixture with a water-insoluble substituted phenol to give a water-insoluble reaction product, and then reacting said reaction product with formaldehyde. A novel cured epoxy resin is produced by reacting the agent with an uncured epoxy resin, and the reaction can be done in a wet environment or even under water.Type: GrantFiled: July 11, 1984Date of Patent: January 1, 1985Inventor: Lowell O. Cummings
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Patent number: 4481346Abstract: A method of producing polymers of the polyurethane type without the use of isocyanates is characterized by that compounds containing active atoms of hydrogen, preferably oligoesterols or oligoetherols, are amidated with isocyanic acid, preferably obtained "in statu nascendi", and then amide compounds thus obtained, preferably oligourethanes, oligoallophanates or oligourethanallophanates, are condensed with an aldehyde in a medium of pH not higher than 10, till obtaining a polymer.It is preferable to amidate oligoesterols or oligoetherols with isocyanic acid obtained from urea in the presence of hydrochloride of a tertiary amine. Oligourethanes, oligoallophanates or oligourethanallophanates can be condensed alone with formaldehyde or in the presence of other compounds able to react with formaldehyde or their hydroxymethyl derivatives.Type: GrantFiled: July 5, 1983Date of Patent: November 6, 1984Assignee: Wyzsza Szkola Inzynierska Im. Kazimierza PulaskiegoInventors: Zygmunt Wirpsza, Krzysztof Kowalski
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Patent number: 4480055Abstract: Amino-resin products, which include aminoplast foams, can be modified by reacting an aminoplast precondensate, which contains an excess of formaldehyde or to which supplemental formaldehyde or another lower monoaldehyde or dialdehyde has been added before processing, with a hardening agent or with a solution of hardening agent, surfactant, and foamer in the presence of an additive that consists of one or more mononuclear or binuclear phenols, phenolic ethers, or acenaphthene derivatives with the overall formulas ##STR1## in which X is H, OH, SO.sub.3 H, Cl, CH.sub.3, or C.sub.2 H.sub.5 andR is H or an alkyl radical, with 1 to 9 carbon atoms, at a pH between about 1 and 2, mixed if necessary with aromatic sulphonic acids, at a pH between about 1 and 2. The modified products can be employed wherever free formaldehyde is undesirable.Type: GrantFiled: February 26, 1982Date of Patent: October 30, 1984Assignee: Schaum-Chemie Wilhelm Bauer G.m.b.H. & Co. KGInventor: Heinz Baumann
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Patent number: 4454298Abstract: A granular or powdery resin which is a condensation product of a phenol and an aldehyde and optionally a nitrogen-containing compound having at least two active hydrogens, 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 said 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 500 ppm, and(D) having a methanol solubility (S) of more than 20% by weight when about 10 g of the resin is heated under reflux in 500 ml of substantially anhydrous methanol.Type: GrantFiled: December 23, 1982Date of Patent: June 12, 1984Assignee: Kanebo Ltd.Inventors: Hiroaki Koyama, Shigeo Shimizu
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Patent number: 4414379Abstract: A granular or powdery nitrogen-containing phenol-aldehyde copolymer resin which is a condensation product of a phenol, a nitrogen-containing compound having at least two active hydrogen atoms and an aldehyde, 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 said particles having a particle diameter of 0.1 to 100 microns,(B) having such a size that at least 50% by weight thereof can pass through a 150 Tyler mesh sieve,(C) having a free phenol content, determined by liquid chromatography, of not more than 50 ppm, and(D) having a D.sub.960-1020 /D.sub.1450-1500 ratio of from 0.1 to 2.0 in its infrared absorption spectrum.Type: GrantFiled: June 16, 1982Date of Patent: November 8, 1983Assignees: Kanebo Ltd., Mitsubishi Chemical Industries LimitedInventors: Hiroaki Koyama, Shigeo Shimizu
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Patent number: 4345061Abstract: This invention relates to cellular plastic compositions of condensation products of phenol-urea and formaldehyde useful for thermal and acoustical insulation and methods for their preparation in which the phenol is present in amounts of about 1 to about 20 percent by weight wherein the condensation product prior to foaming and setting as a rigid cellular plastic has a viscosity at room temperature of approximately 30 to 36 seconds, No. 1 Zahn cup, and a pH maintained in the range of about 6 to 8.Type: GrantFiled: December 15, 1980Date of Patent: August 17, 1982Assignee: C.P. Chemical Co., Inc.Inventor: Walter Hasselman, Jr.
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Patent number: 4311619Abstract: A phenol-aldehyde resin useful in such applications as a cold-set binder for cores and molds used in the foundry industry and reactive prepolymers used in reaction injection molding compositions produced by the steps of reacting a phenol and aldehyde in a mole ratio of 1 to 1-2.3 in the presence of catalytic amounts of an organic compound of aluminum, zirconium or titanium.Type: GrantFiled: April 14, 1980Date of Patent: January 19, 1982Assignee: Aristo CorporationInventors: Charles E. Seeney, John F. Kraemer, Larry J. Hoffman
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Patent number: 4266045Abstract: An etherified phenolic chelate resin prepared by stabilizing and protecting the chelate groups of a phenolic chelate resin and then converting some or all of the phenolic hydroxyl groups into ether groups; a process for the production of the etherified phenolic chelate resin; and a method for separating a heavy metal ion from an aqueous solution having a pH of at least 7 by using this etherified phenolic chelate resin.Type: GrantFiled: September 11, 1978Date of Patent: May 5, 1981Assignee: Unitika Ltd.Inventors: Hiroyuki Uejima, Masahide Hirai, Tsutomu Sakaida
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Patent number: 4252938Abstract: An acid agent comprises a liquid water-insoluble product of concurrent reaction of:(a) one mole of an hydroxy(R)-methyl derivative of phenol in which 0.4-2.0 moles of HO--CH(R)-groups are present per one mole of phenol, wherein R equals H--, CH.sub.3 --, or(b) one mole of phenol and 0.3-2.0 moles of an aldehyde and(c) 0.03-100.0 moles of an aryl sulphonic acid, having an acid number from 10 to 300 (mg.KOH/g) with a maximum water content of 35% by weight.The process of reacting said components is conducted in a flow reactor for 0.1-10 minutes at 50.degree.-150.degree. C.The acid agent according to the invention may be modified with other substances, such as amines, alcohols, or acids to impart additional useful properties thereto. The acid agent has low viscosity, low corrosive activity, improves the strength of phenol-formaldehyde resins cured therewith by 30% and lowers their water absorption capacity by 2-10 times.Type: GrantFiled: August 29, 1977Date of Patent: February 24, 1981Inventors: Vasily D. Valgin, Alexandr M. Vasilenko, Dmitry V. Valgin, Ljudmila A. Istratova