Nitrogen-containing Reactant Contains The -n-c(=o)-n- Group Patents (Class 528/164)
  • Patent number: 8759471
    Abstract: 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: Grant
    Filed: May 19, 2010
    Date of Patent: June 24, 2014
    Assignee: Allnex Germany GmbH
    Inventors: Ralph Schäfer, Peter Ziegler
  • Publication number: 20110306735
    Abstract: 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: Application
    Filed: August 24, 2011
    Publication date: December 15, 2011
    Applicant: DSM IP Assets B.V.
    Inventor: Rudolfus Antonius Theodorus Maria VAN BENTHEM
  • Patent number: 7989575
    Abstract: 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: Grant
    Filed: December 14, 2007
    Date of Patent: August 2, 2011
    Assignee: Momentive Specialty Chemicals Inc.
    Inventor: Stephen W. Arbuckle
  • Patent number: 7910667
    Abstract: 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: Grant
    Filed: September 11, 2009
    Date of Patent: March 22, 2011
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Atteye Houssein Abdourazak
  • Patent number: 7511114
    Abstract: 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: Grant
    Filed: November 28, 2006
    Date of Patent: March 31, 2009
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Masaaki Miyamoto, Takao Tayama, Kiyoji Kuma, Eiji Fujimoto
  • Patent number: 7323534
    Abstract: 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: Grant
    Filed: October 12, 2005
    Date of Patent: January 29, 2008
    Assignee: Hexion Specialty Chemicals, Inc.
    Inventor: Stephen W. Arbuckle
  • Patent number: 7084233
    Abstract: 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: Grant
    Filed: March 31, 2004
    Date of Patent: August 1, 2006
    Assignees: Mitsubishi Chemical Corporation, Mitsubishi Engineering-Plastics Corporation
    Inventors: Masaaki Miyamoto, Takao Tayama, Hiroshi Nakano
  • Patent number: 6916505
    Abstract: 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: Grant
    Filed: March 4, 2003
    Date of Patent: July 12, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William R. Raymond, Michael Cook
  • Patent number: 6706809
    Abstract: 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: Grant
    Filed: November 21, 2001
    Date of Patent: March 16, 2004
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Kim Tutin, W. Hayes Ingram, Mary L. Epling, Kurt D. Gabrielson, James T. Wright, Carl R. White
  • Patent number: 6699958
    Abstract: 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: Grant
    Filed: February 13, 2003
    Date of Patent: March 2, 2004
    Assignee: Borden Chemical, Inc.
    Inventor: William D. Detlefsen
  • Patent number: 6657016
    Abstract: 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: Grant
    Filed: March 14, 2002
    Date of Patent: December 2, 2003
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventor: Takeshi Yatsuka
  • Patent number: 6646094
    Abstract: 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: Grant
    Filed: December 17, 2001
    Date of Patent: November 11, 2003
    Assignees: CertainTeed Corporation, Borden Chemical, Inc.
    Inventors: Vinay Malhotra, Wayne Walliser, Susan G. Watson, Pierre C. Herault, Domenic Tessari, Philippe Espiard, Serge Tetart, Bruno Malhieuxe
  • Patent number: 6541576
    Abstract: 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: Grant
    Filed: August 11, 1998
    Date of Patent: April 1, 2003
    Assignee: Borden Chemical, Inc.
    Inventors: Earl K. Phillips, Arthur J. Garwood, William D. Detlefsen
  • Patent number: 5763558
    Abstract: 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: Grant
    Filed: June 11, 1996
    Date of Patent: June 9, 1998
    Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & Cie
    Inventors: Brigitte Marie Chauvin, Olivier Durel
  • Patent number: 5681916
    Abstract: 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: Grant
    Filed: June 29, 1995
    Date of Patent: October 28, 1997
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Adolf Buschfeld, Matthias Lattekamp, Manfred Gramse, Hans-Jurgen Krezmin
  • Patent number: 5629083
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: May 13, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5623032
    Abstract: 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: Grant
    Filed: June 23, 1995
    Date of Patent: April 22, 1997
    Assignee: Angus Chemical Company
    Inventor: Gaoming Wu
  • Patent number: 5621052
    Abstract: 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: Grant
    Filed: December 29, 1992
    Date of Patent: April 15, 1997
    Assignee: Cytec Technology Corp.
    Inventors: Jeno G. Szita, Paul S. Waterman
  • Patent number: 5605986
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: February 25, 1997
    Assignee: Cytec Technology Corp.
    Inventors: Jeno G. Szita, Paul S. Waterman
  • Patent number: 5538761
    Abstract: 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: Grant
    Filed: June 13, 1995
    Date of Patent: July 23, 1996
    Assignee: Schuller International, Inc.
    Inventor: Thomas J. Taylor
  • Patent number: 5473012
    Abstract: 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: Grant
    Filed: November 22, 1994
    Date of Patent: December 5, 1995
    Assignee: CertainTeed Corporation
    Inventors: Kathleen H. Coventry, David A. Segal, Jacky Joachim
  • Patent number: 5368803
    Abstract: 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: Grant
    Filed: February 12, 1993
    Date of Patent: November 29, 1994
    Assignee: United Technologies Automotive, Inc.
    Inventors: Mark J. Brow, Ronald P. Pitsch
  • Patent number: 5340903
    Abstract: 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: Grant
    Filed: August 27, 1993
    Date of Patent: August 23, 1994
    Assignee: Isover Saint-Gobain
    Inventors: M. Serge Tetart, M. David Segal
  • Patent number: 5300562
    Abstract: 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: Grant
    Filed: June 8, 1993
    Date of Patent: April 5, 1994
    Assignee: CertainTeed Corporation
    Inventors: Kathleen H. Coventry, David A. Segal
  • Patent number: 5270434
    Abstract: 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: Grant
    Filed: November 2, 1992
    Date of Patent: December 14, 1993
    Assignee: Isover Saint-Gobain
    Inventors: M. Serge Tetart, M. David Segal
  • Patent number: 5194331
    Abstract: 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: Grant
    Filed: September 16, 1991
    Date of Patent: March 16, 1993
    Assignee: Allied-Signal Inc.
    Inventors: Sajal Das, Dusan C. Prevorsek
  • Patent number: 5155164
    Abstract: 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: Grant
    Filed: May 8, 1991
    Date of Patent: October 13, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Graf, Adolf Stuebinger, Klaus Lorenz, Ortwin Schaffer, Karl Stork
  • Patent number: 5102972
    Abstract: 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: Grant
    Filed: July 25, 1990
    Date of Patent: April 7, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Raymond J. Swedo, Joseph J. Zupancic
  • Patent number: 5011886
    Abstract: 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: Grant
    Filed: February 26, 1990
    Date of Patent: April 30, 1991
    Assignee: Rwe-Dea Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Adolf Buschfeld, Matthias Lattekamp, Gerd Ripkens, Hans Schittek
  • Patent number: 4960826
    Abstract: 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: Grant
    Filed: February 19, 1988
    Date of Patent: October 2, 1990
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 4857581
    Abstract: 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: Grant
    Filed: December 15, 1987
    Date of Patent: August 15, 1989
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Anton Arzt
  • Patent number: 4855394
    Abstract: 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: Grant
    Filed: January 25, 1989
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Goeckel, Harro Petersen, Rolf Osterloh, Eberhard Schupp, Werner Loch, Thomas Schwerzel
  • Patent number: 4839445
    Abstract: 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: Grant
    Filed: January 6, 1988
    Date of Patent: June 13, 1989
    Assignee: Unitika, Ltd.
    Inventors: Yoshiaki Echigo, Kenichi Sugawara, Mutsunori Yamao, Yoshiyuki Suematu, Keiichi Asami, Tuneyuki Ohsawa
  • Patent number: 4757108
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: July 12, 1988
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 4731430
    Abstract: 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: Grant
    Filed: July 9, 1986
    Date of Patent: March 15, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz E. Kempter, Juergen Nieberle
  • Patent number: 4722991
    Abstract: 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: Grant
    Filed: May 23, 1986
    Date of Patent: February 2, 1988
    Assignee: Acme Resin Corporation
    Inventor: David R. Armbruster
  • Patent number: 4710406
    Abstract: 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: Grant
    Filed: January 20, 1987
    Date of Patent: December 1, 1987
    Assignee: Isover Saint-Gobain
    Inventors: Roger Fugier, Charles de Goys de Mezerac, Jacky Joachim, Michel Decagny
  • Patent number: 4663419
    Abstract: 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: Grant
    Filed: November 19, 1984
    Date of Patent: May 5, 1987
    Assignee: Isover Saint-Gobain
    Inventors: Roger Fugier, Charles D. de Mezerac, Jacky Joachim, Michel Decagny
  • Patent number: 4659787
    Abstract: 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: Grant
    Filed: November 14, 1985
    Date of Patent: April 21, 1987
    Assignee: Chemcrete International Partnership
    Inventor: Lowell O. Cummings
  • Patent number: 4574145
    Abstract: 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: Grant
    Filed: September 28, 1984
    Date of Patent: March 4, 1986
    Assignee: Chemcrete International
    Inventor: Lowell O. Cummings
  • Patent number: 4546168
    Abstract: 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: Grant
    Filed: August 9, 1984
    Date of Patent: October 8, 1985
    Assignee: Hitachi, Ltd.
    Inventors: Akio Takahashi, Takeshi Shimazaki, Motoyo Wajima, Hirosada Morishita
  • Patent number: 4491654
    Abstract: 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: Grant
    Filed: July 11, 1984
    Date of Patent: January 1, 1985
    Inventor: Lowell O. Cummings
  • Patent number: 4481346
    Abstract: 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: Grant
    Filed: July 5, 1983
    Date of Patent: November 6, 1984
    Assignee: Wyzsza Szkola Inzynierska Im. Kazimierza Pulaskiego
    Inventors: Zygmunt Wirpsza, Krzysztof Kowalski
  • Patent number: 4480055
    Abstract: 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: Grant
    Filed: February 26, 1982
    Date of Patent: October 30, 1984
    Assignee: Schaum-Chemie Wilhelm Bauer G.m.b.H. & Co. KG
    Inventor: Heinz Baumann
  • Patent number: 4454298
    Abstract: 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: Grant
    Filed: December 23, 1982
    Date of Patent: June 12, 1984
    Assignee: Kanebo Ltd.
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4414379
    Abstract: 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: Grant
    Filed: June 16, 1982
    Date of Patent: November 8, 1983
    Assignees: Kanebo Ltd., Mitsubishi Chemical Industries Limited
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4345061
    Abstract: 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: Grant
    Filed: December 15, 1980
    Date of Patent: August 17, 1982
    Assignee: C.P. Chemical Co., Inc.
    Inventor: Walter Hasselman, Jr.
  • Patent number: 4311619
    Abstract: 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: Grant
    Filed: April 14, 1980
    Date of Patent: January 19, 1982
    Assignee: Aristo Corporation
    Inventors: Charles E. Seeney, John F. Kraemer, Larry J. Hoffman
  • Patent number: 4266045
    Abstract: 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: Grant
    Filed: September 11, 1978
    Date of Patent: May 5, 1981
    Assignee: Unitika Ltd.
    Inventors: Hiroyuki Uejima, Masahide Hirai, Tsutomu Sakaida
  • Patent number: 4252938
    Abstract: 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: Grant
    Filed: August 29, 1977
    Date of Patent: February 24, 1981
    Inventors: Vasily D. Valgin, Alexandr M. Vasilenko, Dmitry V. Valgin, Ljudmila A. Istratova