Heterocyclic Nitrogen Reactant Or Polymer Therefrom, E.g., Melamine, Etc. Patents (Class 525/497)
  • Patent number: 10252966
    Abstract: A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yield and purity without resorting to solvent intense purification methods. Zinc acetate was shown to be selective catalyst for ortho-coupling of formaldehyde but was unreactive with more sterically demanding aldehydes. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the phenol. Acid solutions could be recycled and used multiple times without decreases in activity or yield.
    Type: Grant
    Filed: April 11, 2013
    Date of Patent: April 9, 2019
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Benjamin G. Harvey, Heather A. Meylemans
  • Patent number: 8278443
    Abstract: The present invention relates to a resin composition for an optical film, comprising a polyarylate resin and an amino resin having a triazine structure, and to an optical film prepared by using the same. By using the resin composition for an optical film, a thickness direction retardation can be controlled, while having a negative value, during a step of fabricating the optical film, an in-plane retardation can be controlled, and the optical film can be used as a substrate of a display instead of a glass substrate without an additional retardation compensation film.
    Type: Grant
    Filed: January 4, 2008
    Date of Patent: October 2, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Sang-Uk Ryu, Dong-Ryul Kim, Dae-Woo Nam
  • 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: 7872088
    Abstract: Disclosed are binders including urea-extended phenol-formaldehyde alkaline resole resins to which melamine-containing resin has been added, and non-woven fiber compositions made therewith. The disclosed binders may be cured to low formaldehyde-emission and low trimethylamine-emission, water-resistant thermoset binders.
    Type: Grant
    Filed: February 15, 2007
    Date of Patent: January 18, 2011
    Assignee: Knauf Insulation GmbH
    Inventors: William S. Miller, Brian L. Swift, Scott L. Stillabower
  • Patent number: 7345101
    Abstract: A corrosion resistant, alkali resistant coating composition is disclosed. The composition comprises a binder comprising a reaction product of an epoxy-containing material and a phosphorus-containing material together with a curing agent. Aminoplasts, especially melamine-based aminoplasts, are particularly suitable curing agents. A source of silicon can optionally be included. The compositions also provide excellent adhesion and can be used with or without a weldable primer. The compositions are applied to and cured on a metal substrate.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: March 18, 2008
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Michael J. Pawlik, Dennis W. Jones, Ralph C. Gray, Richard M. Nugent, Jr., Yves Le Disert, Laurent Deronne
  • 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: 7087664
    Abstract: A resin film comprising (A) an epoxy resin having two or more glycidyl groups in a molecule, (B) an epoxy resin curing agent, (C) a thermoplastic resin, and (D) a filler, wherein the filler content in at least either one of the surface regions on the cross-section of the film is less than the filler concentration in the central region. The resin film has not only toughness but also fire retardancy, high interlayer adhesion strength and good processability of metal plating.
    Type: Grant
    Filed: January 23, 2004
    Date of Patent: August 8, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiaki Hayashi, Katsuhiro Furuta
  • Patent number: 6992151
    Abstract: The present invention discloses an active-hydrogen-containing curing agent having a phosphorus group, and a flame retardant cured epoxy resin which can be prepared via an addition reaction between the active hydrogen and the epoxide group of an epoxy resin. The cured flame retardant epoxy resin is environmentally friendly and is suitable for printed circuit board and semiconductor encapsulation applications. The phosphorus group of the curing agent has a chemical structure as follows: wherein Ar is a substituted or un-substituted phenyl or phenoxy.
    Type: Grant
    Filed: July 14, 2003
    Date of Patent: January 31, 2006
    Assignee: National Science Council
    Inventors: Chun-Shan Wang, Jeng-Yueh Shieh
  • Patent number: 6936651
    Abstract: A composition for forming a crystalline thermoplastic (such as polyacetal) composition for improving compatibility using a ternary blend that includes a mineral filler and elastomer material and an article made therefrom. The mineral filler may be coated or uncoated.
    Type: Grant
    Filed: September 11, 2003
    Date of Patent: August 30, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Edmund Arthur Flexman, Mark Gary Weinberg
  • Patent number: 6864344
    Abstract: Sulfonated condensation products that are stable in storage and have increased thermal stability are based on aminoplastic formers having at least two amino groups or naphthalene and formaldehyde and, optionally include organic nitrogen bases which additionally contain, as nitrogenous formulation auxiliary agents, compounds of general formula (I) R1—NH—X—Y—R2, wherein R1 and R2 independently represent H, —CH3, —C2H5, —C3H7, —(CH2)n—CH2—; X?—CH2, CO, CS; Y?S, NH, —(CH2)m—; n=0 to 9; m=1 to 4; and/or compounds of general formula (II), wherein Z?—OCH3, —SO3—H, —SO3Na+, —NO2, —NH2, —NH—NH2, —CO2—Na+, —CHO. The mole ratio of aminoplastic formers: formaldehyde: sulfite: nitrogenous formulation auxiliary agents rangin from 1:1.9 to 6.0:1.0 to 2.0:0.01 to 1.5 and/or the mole ratio of naphthalene sulfonic acid: formaldehyde; nitrogenous formulation auxiliary agents equals 1:0.7 to 3.0:0.01 to 1.5. Method for preparing these condensation products of using them, e.g.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: March 8, 2005
    Assignee: SKW Polymers GmbH
    Inventors: Uwe Holland, Martin Matzinger, Johann Plank
  • Patent number: 6846567
    Abstract: A surface-protected plastic composite material comprising a transparent plastic, a coating layer (I) as a first layer stacked on the transparent plastic and a thermally cured coating layer (II) as a second layer stacked on the first layer, the coating layer (I) being formed of a resin composition containing at least 50% by weight, based on the resin content thereof, of an acrylic resin which is an acrylic resin containing at least 50 mol % of recurring unit based on an alkyl methacrylate, the thermally cured coating layer (II) being made of an organosiloxane resin formed from the following components a, b and c, (A) colloidal silica (component a), (B) a hydrolysis condensate (component b) of a trialkoxysilane, (C) a hydrolysis condensate (component c) of a tetraalkoxysilane, the organosiloxane resin containing 5 to 45% by weight of the component a, 50 to 80% by weight of the component b and 2 to 30% by weight of the component c, and use of the composite material as a window glass.
    Type: Grant
    Filed: January 31, 2000
    Date of Patent: January 25, 2005
    Assignee: Teijin Chemicals, Ltd.
    Inventors: Tatsuya Ekinaka, Yoshihiko Imanaka
  • Patent number: 6800717
    Abstract: Non-gelled polymeric polyols are prepared by the acid catalyzed copolymerization of epoxy resins and water. When the starting resin is an epoxy resin derived from bisphenol-A, the resulting product has much lower levels of bisphenol-A and diglycidyl ether of bisphenol-A (DGEBA) compared to traditional epoxy resins of comparable molecular weight prepared by the advancement process. The product can be cured with OH reactive crosslinkers such as amino resins and polyisocyanates to yield thermosetting coatings with useful properties.
    Type: Grant
    Filed: January 31, 2002
    Date of Patent: October 5, 2004
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick Herbert Walker, John Bartram Dickenson
  • Patent number: 6613848
    Abstract: A hardener for an epoxy resin comprises a phenolic, thiophenolic, aminophenyl, tris-phenolic, tris-thiophenolic, tris-aminophenyl, tetrakis-phenolic, tetrakis-thiophenolic, or tetrakis-aminophenyl compounds; or phenol-formaldehyde or phenol-formaldehyde/melamine-formaldehyde resins wherein the phenyl rings are substituted with at least one of the structures wherein R1 and R2 independently are H, C1-C18 alkyl, C6-C18 aryl, C6-C18 substituted aryl, C6-C18 aryl methylene, or C6-C18 substituted aryl methylene; X is O, S or NH and Ar is wherein R is C1-C4 alkyl and n=0-5.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: September 2, 2003
    Assignee: National Science Council
    Inventors: Chun-Shan Wang, Jeng-Yueh Shieh
  • Patent number: 6566459
    Abstract: A melamine-urea-formaldehyde resin modified with a cyclic urea prepolymer and sodium metabisulfite. Products prepared with the binder include wood composites such as particleboard and medium density fiberboard.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: May 20, 2003
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Pablo G. Dopico, Stacey L. Wertz, James C. Phillips, George E. Mirous
  • Patent number: 6528595
    Abstract: A composition useful as a sealant, coating, a potting agent for a printed circuit board, a prepreg or an adhesive comprises a compound (A) wherein all or a part of the oxirane rings in an epoxy compound is replaced with thiirane rings represented by the following formula (1): or compound (A) and compound (B) which contains oxirane rings and no thiirane ring in the molecule, wherein the ratio of oxirane ring/thiirane ring is from 90/10 to 10/90.
    Type: Grant
    Filed: October 6, 2000
    Date of Patent: March 4, 2003
    Assignee: The Yokohama Rubber Co., Ltd.
    Inventors: Masahiro Ikawa, Hiroyuki Okuhira, Keisuke Chino
  • Patent number: 6500447
    Abstract: The present invention provides pH-sensitive micro-capsules, compositions containing them, methods for their preparation and methods for their use.
    Type: Grant
    Filed: August 13, 1999
    Date of Patent: December 31, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Robin William Dexter, Brian Eric Benoff
  • Patent number: 6399719
    Abstract: A melamine-containing resin modified with a cyclic urea prepolymer comprising urea, formaldehyde and ammonia or a primary amine. The prepolymer-modified melamine-containing resin provides useful binders alone, or when combined or coreacted with other resins. Products prepared with the binder include wood composites such as particleboard and medium density fiberboard.
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: June 4, 2002
    Assignee: Georgia-Pacific Resins, Inc.
    Inventors: Pablo G. Dopico, Brian M. Peek, Benjamin D. Gapud, Kelly A. Shoemake, James C. Phillips
  • Patent number: 6391967
    Abstract: This invention discloses a flame retarding thermoplastic resin composition, which is comprised of (i) a thermoplastic resin and (ii) a phenolic resin compound as a flame retardant, wherein the phenolic resin compound contains a nitrogen-containing heterocycle and phosphorus. Since the flame retarding thermoplastic resin composition of this invention does not contain halogen, and has excellent flame retardant properties and high heat resistance, it is useful in producing parts and products in the fields of electronics, electricity and automobile.
    Type: Grant
    Filed: February 11, 2000
    Date of Patent: May 21, 2002
    Assignee: Chang Chun Plastics Co., Ltd.
    Inventors: Kuen-Yuan Hwang, Hong-Hsing Chen, Ying-Ling Liu, Wen-Tsai Tsai
  • Publication number: 20010049421
    Abstract: The present invention modifies a cross-linkable thermoset polymer with a thermoplastic polymer to create a spinnable thermoset/thermoplastic polymer composition that may be spun into thermoset/thermoplastic fibers.
    Type: Application
    Filed: January 2, 2001
    Publication date: December 6, 2001
    Inventors: Dominick A. Burlone, Doris Carolyn Morgan
  • Patent number: 5847058
    Abstract: A process for the production of a storage-stable, modified phenol-aldehyde resol resin includes the use of an alkylresorcinol modifier and preferably a readily-available mixture of alkylresorcinols. A binder system includes the modified phenol-aldehyde resin combined with a curing agent that includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The resin and binder system are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: December 8, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5760104
    Abstract: A binder solution of a phenolic novolak resin in solvent, preferably furfuryl alcohol containing at least one chemical agent such as amines containing one to five, preferably two to four, nitrogen atoms, glycerine or mixtures thereof. Preferably, the binder solution contains about 0.2 to about 1.5 weight percent water. The binder solution is for binding refractory objects, preferably those containing doloma (calcined dolomite) aggregate. Methods of mixing these ingredients and using the mixture are also disclosed. Bricks made from the doloma aggregate mixed with the binder solution show good ambient temperature green strength and enhanced modulus of rupture after curing and coking.
    Type: Grant
    Filed: July 9, 1997
    Date of Patent: June 2, 1998
    Assignee: Borden Chemical, Inc.
    Inventor: Arthur Harry Gerber
  • Patent number: 5756599
    Abstract: A process for producing a phenol-aldehyde (e.g., cresol-aldehyde) resin that is modified with a dihydroxybenzene compound. The resin may form a binder system when combined with a curing agent which includes an additional source of an aldehyde. The resin and adhesive are useful in the production of wood composite articles by a steam injection process.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: May 26, 1998
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5646219
    Abstract: A process for the production of a modified phenol-aldehyde resin which may form a binder system when combined with a curing agent which includes an additional source of an aldehyde, e.g., a phenol-formaldehyde resin. The inventive phenol-aldehyde resin may be modified with compounds from one of the following classes: (1) dihydroxybenzenes, (2) aminophenols, and (3) phenylenediamines. The resin and adhesive are useful in the production of a wood composite (such as plywood, oriented strandboard, or fiberboard).
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: Masonite Corporation
    Inventor: Zygmunt Teodorczyk
  • Patent number: 5342916
    Abstract: Condensation polymers of sulfonated phenols, urea, other organic nitrogen-bases and formaldehyde, obtainable by(A) sulfonation of phenols with from 1.0 to 1.5 moles of sulfuric acid per mole of phenol and(B) condensation of these sulfonation products with(a) from 0.5 to 1.8 moles of urea per mole of phenol,(b) from 0.001 to 0.5 moles of at least one other organic nitrogen-base per mole of phenol, and(c) from 1.0 to 3.0 moles of formaldehyde per mole of phenol.The condensation polymers are suitable for use as tanning agents in the leather and skin-producing industry and as spraying aids for redispersible polymer powders.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: August 30, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Weiser, Wolfgang Reuther, Karl Stork, Ortwin Schaffer, Gernot Franzmann, Thomas Schwerzel, Maximilian Angel, Joachim Pakusch, Brigitte Wegner
  • Patent number: 5304456
    Abstract: A negative photoresist composition containing an alkali-soluble resin which is obtainable through a condensation reaction of an aldehyde with a phenol compound containing a compound of the general formula: ##STR1## wherein R.sup.1 to R.sup.9 are independently a hydrogen atom, an alkyl group, an alkenyl group, an alkylcarbonyl group, a halogen atom or a hydroxyl group, provided that at least one of R.sup.1 to R.sup.9 is a hydroxyl group and, at the ortho- or para-position to the hydroxyl group, at least two hydrogen atoms are present; a cross linking agent; and a photo-acid generator, and a negative photoresist composition comprising an alkali-soluble resin, a cross linking agent and a photo-acid generator having a trifluoromethanesulfonic acid ester group, which can increase resolution and contrast of a photoresist pattern.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: April 19, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuji Ueda, Hiromi Ueki, Naoki Takeyama, Takehiro Kusumoto
  • Patent number: 5296584
    Abstract: The invention relates to a composition consisting of a melamine solid suspended or dispersed in a resole resin. The method of the invention favors the intermolecular condensation polymerization reaction between phenol and melamine, rather than homopolymerization between phenol molecules or between melamine molecules. This invention reduces formaldehyde emissions by favoring a reaction whose by-product is water rather than formaldehyde. The compositions are useful for bonding glass fiber mats used for thermal and acoustical insulation.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: March 22, 1994
    Assignee: Borden, Inc.
    Inventor: Wayne R. Walisser
  • Patent number: 5260405
    Abstract: A binding agent for molding compositions and molded bodies produced by reacting a low molecular weight lignin from the Organosolv process with phenol in a weight ratio of 1:20 to 3:1 at 100.degree. to 180.degree. C., adjusting the pH to an acidic value and condensing the mixture with 0.2 to 0.9 moles of formaldehyde per mole of phenol at 60.degree. to 120.degree. C. to form the binding agent useful for producing curable molding compositions, high-temperature molding compositions, refractory products, textile fleeces and friction coatings as well as carbon materials.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: November 9, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5254639
    Abstract: A binding agent for molded bodies and molding compositions produced by prereacting a mixture of 5 to 60% by weight of lignin or a lignin fraction produced by the Organosolv process and 40 to 95% by weight of a phenol novolac resin and subjecting the latter to high shear forces in a kneader or extruder and optionally mixing the same with a curing agent useful in molding compositions and high temperature-stable molded products such as refractory products, friction coatings, textile fleeces and carbon or graphite materials.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: October 19, 1993
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Arno Gardziella, Achim Hansen, Stephan Schroter, Josef Suren
  • Patent number: 5171797
    Abstract: An hydrolytically stable, heat-curable composition useful as an hermetic varnish for electrical conductors comprising an aqueous solution with or without organic co-solvents of:1) an adduct of an epoxide of a phenol-formaldehyde condensate and a dialkanolamine, and2) a water-soluble curing agent comprising both a phenoplast alcohol and an aminoplast such as a melamine for example, hexamethoxymethylmelamine;the cured products thereof which are useful as hermetic varnishes for electrical conductors. i.e. varnishes exposed to refrigerants such as fluorocarbons.
    Type: Grant
    Filed: December 3, 1991
    Date of Patent: December 15, 1992
    Assignee: The P.D. George Company
    Inventors: James I. Crowley, Ronald W. Goetter
  • Patent number: 4978711
    Abstract: Aqueous aminoresin solutions for low-formaldehyde surface bonding, based on condensates of melamine, urea, phenol and formaldehyde having a molar ratio of from 1.4 to 1.8 moles of formaldehyde, from 0.04 mole to 0.1 mole of melamine and from 0.015 to 0.04 mole of phenol per mole of urea, relative to the total amount of the aminoresin, are obtainable by mixing(A) from 20 to 40% by weight of melamine/urea/phenol/formaldehyde consensate with(B) from 60 to 80% by weight of a urea/formaldehyde condensate.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: December 18, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Christof Schmidt-Hellerau, Engelbert Weber, Guenther Matthias
  • Patent number: 4954581
    Abstract: The invention relates to a resin for the production of cellulose based products, such as particle boards. The resin is a condensation product of formaldehyde, urea and phenol and optionally melamine with a molar ratio of 1.4-0.8 moles of urea, 0.006-0.04 moles of phenol and 0-0.04 moles of melamine per mole formaldehyde. The invention also relates to a method of producing such a resin. According to the method a separately prepared cross-linking agent containing a co-condensate of phenol, formaldehyde and urea or containing a co-condensate of phenol and formaldehyde together with urea, is added to a pre-condensate of formaldehyde, urea and optionally melamine, whereafter the mixture is condensed. As an alternative the cross-linking agent can be added to a finished condensate of formaldehyde, urea and optionally melamine.The invention also relates to a method of manufacturing glued cellulose based products.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: September 4, 1990
    Assignee: Dynobel A/S
    Inventors: Leif A. Flodman, Per E. G. Gabrielsson
  • Patent number: 4857609
    Abstract: The invention relates to a resin for the production of cellulose based products, such as particle boards. The resin is a condensation product of formaldehyde, urea and phenol and optionally melamine with a molar ratio of 1.4-0.8 moles of urea, 0.006-0.04 moles of phenol and 0-0.04 moles of melamine per mole formaldehyde. The invention also relates to a method of producing such a resin. According to the method a separately prepared cross-linking agent containing a co-condensate of phenol, formaldehyde and urea or containing a co-condensate of phenol and formaldehyde together with urea, is added to a pre-condensate of formaldehyde, urea and optionally melamine, whereafter the mixture is condensed. As an alternative the cross-linking agent can be added to a finished condensate of formaldehyde, urea and optionally melamine.The invention also relates to a method of manufacturing glued cellulose based products.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: August 15, 1989
    Assignee: Dynobel A/S
    Inventors: Leif A. Flodman, Per Erik G. Gabrielsson
  • Patent number: 4845162
    Abstract: The present invention relates to a composition comprising a phenolic resin, as for example phenol formaldehyde, an active hydrogen containing polymer as for example a polyamide, and a curing agent, such as a polyepoxide.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: July 4, 1989
    Assignee: Allied-Signal Inc.
    Inventors: George J. Schmitt, Dusan C. Prevorsek, Hong B. Chin, Kwok W. Lem
  • Patent number: 4831089
    Abstract: The invention relates to a method for the production of a resin which is used for manufacturing of an adhesive for cellulose based products. According to the method 30-70% by weight of a urea phenol resin with a molar ratio of 1.4-0.6 moles or urea, 0.006-0.3 moles of phenol and 0-0.04 moles of melamine per mole formaldehyde, are mixed with 70-30% by weight of a melamine resin with a molar ratio formaldehyde: melamine of 1.7-2.4. The urea-phenol resin has been prepared by adding a cross-linking agent containing a co-condensate of phenol, formaldehyde and urea to a pre-condensate of formaldehyde, urea and optionally melamine and condensing under acid conditions.According to a further embodiment the cross-linking agent is added to a evaporated condensate of formaldehyde, urea and optionally melamine.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: May 16, 1989
    Assignee: Dynobel A/S
    Inventors: Leif A. Flodman, Per E. G. Gabrielsson
  • Patent number: 4699949
    Abstract: Compounds of formula I or II ##STR1## in which n is 1 or 2, R.sup.1 is phenyl, substituted phenyl, alkyl, substituted alkyl, hydrogen, --OH or amino, R.sup.2 is hydrogen, R.sup.3 is hydrogen, alkyl, substituted alkyl, phenyl or substituted phenyl, R.sup.4 is alkyl, phenyl, substituted phenyl, alkylene or arylene, X is --O--, --S--, --CH.sub.2 -- and Y is a direct bond or --CH.sub.2 -- are latent hardening catalysts for acid curable resins. The catalysts are activated by heat and are used in heat-hardening high-solids industrial varnishes and for coil-coatings, can and wood varnishes.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: October 13, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Werner Rutsch
  • Patent number: 4598110
    Abstract: A resin composition comprising(I) a granular or powdery resin which is a condensation product of a phenol, an aldehyde and optionally a nitrogen-containing compound having at least two active hydrogens and is characterized by (A) containing spherical primary particles and their secondary agglomerated particles each 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, and (C) having a free phenol content, determined by liquid chromatography, of not more than 500 ppm, and(II) at least one member selected from the group consisting of (1) a rubbery elastic material, (2) a thermoplastic resin and (3) a curable resin other than said granular or powdery resin (I) and/or a filler material other than said granular or powdery resin (I).
    Type: Grant
    Filed: June 12, 1984
    Date of Patent: July 1, 1986
    Assignee: Kanebo Ltd.
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4593078
    Abstract: The present invention is directed to polyglycidyl ethers having, on average, n epoxy groups per molecule, where 1<n.ltoreq.2, which comprise the reaction products of multifunctional polyglycidyl ethers having, on average, x epoxy groups per molecule, where x>2, with (x-n) mol of monofunctional phenols per mol of the multifunctional polyglycidyl ether and to a process for their preparation and their use in preparing thermosetting coating compositions, particularly for use in electrodeposition coating of articles.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: June 3, 1986
    Assignee: Shell Oil Company
    Inventors: Petrus G. Kooymans, Stephen A. Stachowiak, Jurrianus Bekooij, Werner T. Raudenbusch
  • Patent number: 4476277
    Abstract: A resin composition comprising(I) a granular or powdery resin which is a condensation product of a phenol, an aldehyde and optionally a nitrogen-containing compound having at least two active hydrogens and is characterized by (A) containing spherical primary particles and their secondary agglomerated particles each 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, and (C) having a free phenol content, determined by liquid chromatography, of not more than 500 ppm, and(II) at least one member selected from the group consisting of (1) a rubbery elastic material, (2) a thermoplastic resin and (3) a curable reisn other than said granular or powdery resin (I) and/or a filler material other than said granular or powdery resin (I).
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: October 9, 1984
    Assignee: Kanebo Ltd.
    Inventors: Hiroaki Koyama, Shigeo Shimizu
  • Patent number: 4433119
    Abstract: There are described liquid compositions of a hemiformal of phenol and/or a hemiformal of a methylolated phenol with a miscible polymers such as phenol-formaldehyde resoles, phenol-formaldehyde, novolacs, aromatic polyesters, unsaturated polyesters, poly(aryl-ethers), aromatic polycarbonates urea-formaldehyde resins, or melamine-formaldehyde resins. The compositions are useful for forming thermoset plastic materials.
    Type: Grant
    Filed: January 19, 1982
    Date of Patent: February 21, 1984
    Assignee: Union Carbide Corporation
    Inventors: George L. Brode, Sui-Wu Chow
  • Patent number: 4350800
    Abstract: A process for the preparation of synthetic resins based on resorcinol compounds which comprises reacting a resorcinol pitch which is obtained in the manufacture of resorcinol from benzenedisulfonic acid in at least one step with an oxo-compound selected from aldehydes, ketones and compounds based on or splitting off at least one of these substances, and the use of the products as binders for abrasive articles.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: September 21, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Franz Landauer, Klaus Schmiedel
  • Patent number: 4345054
    Abstract: A high-molecular-weight novolak type substituted phenolic resin having a number average molecular weight of at least 1500 is prepared by reacting (A) (i) a phenol comprised mainly of a bifunctional phenol or (ii) a low-molecular-weight novolak type substituted phenolic resin derived from this phenol and an aldehyde with (B) a chain extender selected from the group consisting of (i) a dimethylolated product of a bifunctional or trifunctional phenol, (ii) a low-molecular-weight resol type substituted phenolic resin derived from a phenol comprised mainly of a bifunctional phenol and an aldehyde, (iii) an aldehyde, (iv) a ketone, (v) a diol and (vi) a dihalide in the presence of an acid catalyst, with the proviso that if the reactant (A) is the phenol (i), the chain extender is the resol type substituted phenolic resin (ii).
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: August 17, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Nobuyuki Takeda, Tadao Iwata
  • Patent number: 4342852
    Abstract: Disclosed is a setting type resin composition comprising (A) a setting type resin and (B) 10 to 200 parts by weight, per 100 parts by weight of said resin (A), of a substantially linear, high-molecular-weight novolak type substituted phenolic resin which comprises a constituent phenol component comprised mainly of a bifunctional phenol and has a number average molecular weight of at least 1500. This resin composition has highly improved heat resistance and mechanical strength characteristics by virtue of incorporation of the high-molecular-weight novolak type substituted phenolic resin, and this improving effect is especially prominent when an epoxy resin is used as the setting type resin.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: August 3, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Nobuyuki Takeda, Tadao Iwata
  • Patent number: 4285848
    Abstract: Preparation of this adhesive is characterized by initial condensation of phenol and formaldehyde, which is followed by sequential condensation of melamine and then urea to produce a wood adhesive which passes the standard 6-cycle test.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: August 25, 1981
    Assignee: Borden, Inc.
    Inventor: Charles H. Hickson
  • Patent number: 4276209
    Abstract: Co-condensates are prepared by condensing from 0.8 to 2.0 moles of butyraldehyde with 1 mole of a phenol at from 80.degree. to 220.degree. C. with the addition, before, during or after the condensation, of from 5 to 50% by weight, based on the mixture of phenol and butyraldehyde, of one or more thermoplastics containing functional groups, which reacts with phenol, butyraldehyde or the phenol-butyraldehyde resin under the condensation conditions. The co-condensates are used as hot-melt adhesives and as binders for nonwovens.
    Type: Grant
    Filed: October 23, 1979
    Date of Patent: June 30, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Harro Petersen, Hans-Joachim Krause, Kurt Fischer, Adolph Segnitz, Horst Zaunbrecher
  • Patent number: 4195154
    Abstract: The title compounds are of the formula: ##STR1## wherein R is a chemical bond, oxygen, sulfur, alkylene or alkylidene; W is hydrogen or a (--CR.sub.1 R.sub.2 --CR.sub.3 R.sub.4 --NHR.sub.5) group with the proviso that at least two W groups are (--CH.sub.1 R.sub.2 --CR.sub.3 R.sub.4 --NHR.sub.5) groups; wherein R.sub.1 -R.sub.4 are each independently hydrogen, lower alkyl or hydroxy-substituted lower alkyl; R.sub.5 is hydrogen or a ##STR2## group, wherein R.sub.6 is hydrogen, hydrocarbyl or inertly substituted hydrocarbyl; X, Y and Z are each independently inert substituents; m and p are each independently integers of from zero to four, inclusive; n is an integer of from zero to three, inclusive; q is a number of from zero to about ten; and M is alkylene or alkylidene. They are conveniently prepared by reacting a 2-oxazoline of the formula: ##STR3## with a polyhydric polyphenol of the formula: ##STR4## in the presence of certain metal salt catalysts (e.g. zinc acetate).
    Type: Grant
    Filed: August 15, 1977
    Date of Patent: March 25, 1980
    Assignee: The Dow Chemical Company
    Inventors: Mark E. Kaiser, Harry A. Smith
  • Patent number: 4170611
    Abstract: A process for preparing bonding agents for light-colored weatherproof wood materials, based on alkali-condensed phenol-formaldehyde mixed condensates.
    Type: Grant
    Filed: January 5, 1977
    Date of Patent: October 9, 1979
    Assignee: Deutsche Texaco Aktiengesellschaft
    Inventors: Friedrich Josten, Martin Cherubim, Rainer Striso
  • Patent number: RE30375
    Abstract: This specification discloses ecologically desirable, improved binder compositions suitable for bonding fibers. These binders exhibit low pollutant characteristics and improved properties, due to a combination into the binder of aminoplast resins or non phenolic monomeric materials capable of co-condensing with formaldehyde, together with a substantially phenol free, low mono methylolphenol high .[.ortho para di.]. .Iadd.2,4,6-tri .Iaddend.methylol .[.phenol.]. .Iadd.phenols .Iaddend.content, water soluble thermosetting phenol formaldehyde resole solution. The phenolic resole resin is made to conform to the desired composition by mixing together a high mole ratio of formaldehyde with phenol and calcium hydroxide with cooling so that very little reaction takes place.
    Type: Grant
    Filed: January 12, 1978
    Date of Patent: August 19, 1980
    Assignee: Fiberglas Canada Ltd.
    Inventors: Hendrik H. J. Deuzeman, Norman Lumley, Ruben A. Santos