Specified Material Contains Nitrogen Patents (Class 525/486)
  • Patent number: 4923912
    Abstract: An epoxy resin composition consisting essentially of(A) an epoxy resin,(B) a curing agent,(C) a curing promoter,(D) an organic silicon compound having at least one phenolic hydroxyl group per molecule, and(E) a filler.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: May 8, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yukio Sasaki, Takayuki Watanabe, Hiroshi Takamiya, Kazuo Watanabe, Yoko Yamazaki
  • Patent number: 4904516
    Abstract: A process for preparing a water soluble phenol-formaldehyde resole resin having improved storage stability employs a calcium compound to catalyze the condensation reaction which occurs under basic conditions. Sulfamic acid is used to neutralize the resole solution, yielding a soluble calcium salt which will not settle out of the solution or clog transfer lines or spray nozzles as may a calcium salt precipitated during the neutralization. Glass fiber insulation produced using a binder prepared with the aqueous resole solution shows enhanced thickness recovery and lower odor potential.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: February 27, 1990
    Inventor: Albert W. Creamer
  • Patent number: 4833204
    Abstract: An epoxy resin composition for a copper-clad laminate comprising an epoxy resin having at least two epoxy groups in one molecule, a phenolic compound having at least two functional groups in one molecule as a hardener, an imidazole compound having a masked imino group as a hardening accelerator, and one or more of nitrogen compounds selected from the group consisting of urea derivatives represented by the formula R.sup.1 --NH--CO--NH.sub.2, wherein R.sup.1 is hydrogen or an organic group; acid amide compounds; and guanidine derivatives, which is advantageously used for the material of a copper-clad laminate. Accordingly, the copper-clad laminate is especially used for the production of printed circuit boards, and its drilling property, peeling resistance of the copper foil, adhesive property, and heat resistance are improved remarkably. In addition, this epoxy resin composition has an excellent storing stability.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: May 23, 1989
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Masami Yusa, Katsuji Shibata, Yasuo Miyadera
  • Patent number: 4800215
    Abstract: Uncured compositions are prepared from dialkanolamines and polyglycidyl ethers of tris(hydroxyphenyl)alkanes. These compositions are water soluble or water miscible.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: January 24, 1989
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Willie L. Myles, Michael P. Kubisiak
  • Patent number: 4754003
    Abstract: Novel epoxidised phenol ethers of formula I ##STR1## are described wherein R.sup.1 denotes C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.9 cycloalkyl or C.sub.7 -C.sub.14 aralkyl, R.sup.2 has one of the meanings of R.sup.1 or is, in addition hydrogen or a radical or formula II ##STR2## R.sup.3 denotes C.sub.1 -C.sub.6 alkyl or halogen, R.sup.4 and R.sup.5 denotes hydrogen or C.sub.1 -C.sub.6 alkyl, R.sup.6 denotes hydrogen or methyl, m is 0, 1 or 2 and n is an integer from 0 to 30, with the proviso that at least two radicals, R.sup.2, must be epoxide groups of formula II. The compounds are especially suitable for encasing electronic components.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: June 28, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles E. Monnier, Martin Roth
  • Patent number: 4740540
    Abstract: A resin composition for a molding material is provided which comprises a resol-type phenolic resin, an epoxy resin and an amine compound having hydrogen atoms directly bonded to the nitrogen atom. The amine compound is contained in such a proportion that the amount of its hydrogen atoms directly bonded to the nitrogen atom is 0.5 to 2.0 equivalents per equivalent of the epoxy groups of the epoxy resin.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: April 26, 1988
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Mamoru Kameda, Masaru Furukawa, Nobuhiko Yamauchi
  • Patent number: 4725652
    Abstract: Latent catalysts for epoxy reactions are prepared by reacting a tetrasubstituted onium compound such as tetrabutylphosphonium acetate.acetic acid complex or an amine compound with an acid having a weak-nucleophilic anion such as fluoboric acid. These catalysts provide stable latent catalysts for epoxy resins for advancement or curing reactions.
    Type: Grant
    Filed: March 4, 1987
    Date of Patent: February 16, 1988
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Van I. W. Stuart
  • Patent number: 4701378
    Abstract: Adhesion between surfaces of metal, reinforced plastics, glass, friction material or ceramics is effected using an adhesive comprising(a) an epoxide resin(b) a nitrogen-containing latent curing agent for this resin, such as dicyandiamide, isophthalic acid dihydrazide or adipic acid dihydrazide, and(c) as accelerator for the cure, and dispersed as a powder in (a) and (b), a solid solution of a nitrogen base having a boiling point above 130.degree. C. and a phenol-aldehyde resin.Typical nitrogen bases used in (c) include benzyldimethylamine, benzimidazole and 2-methylimidazole. Typical phenolic resins are those prepared from phenol and formaldehyde.
    Type: Grant
    Filed: April 2, 1986
    Date of Patent: October 20, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Madan M. Bagga, Christopher H. Bull
  • Patent number: 4698426
    Abstract: Cyclic amidines which are modified by the incorporation of additional polar groups, may be used as catalysts for hardening heat-curable resin compositions comprising polyepoxides and optionally carboxyl group-containing polymers. Such amidine catalysts yield a high reactivity, an excellent storage stability and result in elastic coatings which show a high gloss and a good resistance to solvents.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: October 6, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf-Volker Meyer, Hans-Joachim Kreuder, Erwin Hohl
  • Patent number: 4680346
    Abstract: A coating composition contains an organic polyol, a polyepoxide, a blocked polyisocyanate crosslinking agent, and a phenolic resin. The coating composition also can be formulated as a two package coating composition with a free polyisocyanate crosslinking agent. The composition is flexible, having an elongation of at least 10 percent when cured. This coating composition is particularly suitable as a primer in preparing substrates with a multilayer coating having good flexibility.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: July 14, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Dennis W. Carson, Robert J. Schmitt, Carl A. Seneker, Thomas A. Van Kuren, David R. Wallace
  • Patent number: 4644023
    Abstract: A heat curable epoxy adhesive composition has been developed which is substantially insoluble in cold hydraulic fluid before it is cured and resistant to degradation in hot hydraulic fluid after it is heat cured. The adhesive comprises a diglycidyl ether of bisphenol-A, a lesser amount of an epoxy novolac resin and a catalytic amount of 2-ethyl-4-methyl imidazole curing agent. The adhesive is particularly adapted to automatically and permanently calibrate the relief pressure of check valves in hydraulic systems.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: February 17, 1987
    Assignee: General Motors Corporation
    Inventor: Richard K. Gray
  • Patent number: 4611036
    Abstract: An epoxy resin composition having excellent handling properties, solvent resistance and heat resistance and particularly excellent low-temperature curability is provided which comprises (A) a polyfunctional epoxy resin having an epoxy equivalent of 160 to 2,000 obtained by reacting an epoxy resin having an epoxy equivalent of 100 to 800 with a molecular weight increasing agent containing 2.1 to 10 functional groups (phenolic hydroxyl groups) on an average per molecule and (B) a curing agent for the epoxy resin) as essential ingredients.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: September 9, 1986
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hisashi Sekiguchi, Norio Kobayashi, Hideo Ohgishi
  • Patent number: 4604314
    Abstract: Improved printed circuit boards of laminated thermosetting sheets with epoxy resin as the bonding agent contain for inhibiting copper migration 0.1% to 10% N,N'-bis-salicyloyl hydrazine, based on the weight of the hardened epoxy resin.
    Type: Grant
    Filed: January 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Siemens Aktiengesellschaft
    Inventors: Wolfgang von Gentzkow, Maximilian Hodl, Wolfgang Kleeberg, Helmut Markert
  • Patent number: 4594291
    Abstract: Relatively high molecular weight epoxy resins cured with conventional curing agents are disclosed wherein the relatively high molecular weight epoxy resin is prepared in the presence of the curing agents. The resultant cured epoxy resin has an improvement in Tg or toughness and the mixture prior to reaction and curing is much easier to apply as a coating or in the preparation of castings, laminates and the like as compared to applications of mixtures of relatively high molecular weight epoxy resins and the curing agents.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Jody R. Berman, James A. Clarke
  • Patent number: 4568727
    Abstract: Storage stable, heat curable mixtures obtained from epoxy resins as a binder system containing latent hardening agents as well as fillers and additive materials which have outstanding mechanical and electrical properties and which are obtained as epoxy resin components of an adduct of a high molecular solid epoxy resin and 4,4'-diaminodiarylalkane in a molecular ratio of 1:0.01 to 0.05. The preferred economical curing agent is a phenol formaldehyde condensation product.
    Type: Grant
    Filed: March 12, 1985
    Date of Patent: February 4, 1986
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Rolf Herzog, Dietrich Tichy, Harald Heerdegen, Rolf Kraas, Ulrich Grundke
  • Patent number: 4544432
    Abstract: A method has been developed to use a structural epoxy adhesive to bond together surfaces of phosphated steel electrodeposited with an organic primer. The specially formulated epoxy adhesive contains a cross-linkable epoxy novolac resin, an epoxy reactive diluent, and an imidazole curing agent substituted in at least one position with an alkyl or a hydroxyalkyl group. The amount of the curing agent used in the formulation is much lower than that in a conventional two-part epoxy adhesive such that the adhesive will not attack or degrade the primer layer to weaken the bond strength. The reactive diluent used reduces the viscosity of the mixed adhesive system to facilitate dispersion and wetting of the adhesive on the coated steel surface. Bond strength achieved by this method is adequate for automotive structural applications and is capable of withstanding extended exposure to humidity, salt spray, and other hostile automotive environments without appreciable loss.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: October 1, 1985
    Assignee: General Motors Corporation
    Inventors: Robert T. Foister, Richard K. Gray
  • Patent number: 4510288
    Abstract: Cyclic amidines which are modified by the incorporation of additional polar groups, may be used as catalysts for hardening heat-curable resin compositions comprising polyepoxides and optionally carboxyl group-containing polymers. Such amidine catalysts yield a high reactivity, an excellent storage stability and result in elastic coatings which show a high gloss and a good resistance to solvents.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: April 9, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf-Volker Meyer, Hans-Joachim Kreuder, Erwin Hohl
  • Patent number: 4499246
    Abstract: A catalyst and accelerator for an epoxy system which consists of a halogeisphenate of a catalytically active tertiary amine and which is obtained in a solid form practically water insoluble and odor free but which nevertheless possess the catalytic activity of the tertiary amine. The application describes the proportion of the catalyst by reacting an aqueous suspension of the halogenobisphenol with the tertiary amine, the proportion of epoxy resin systems containing the catalyst and the epoxy resin systems thus formed.
    Type: Grant
    Filed: February 13, 1984
    Date of Patent: February 12, 1985
    Assignee: Societe Anonyme Dite "Manufacture de Produits Chimiques Protex"
    Inventors: Gerard Tesson, Christian Joseph
  • Patent number: 4481311
    Abstract: Binders based on co-condensates of epoxy resins and resols with amines, the epoxy resin being partially defunctionalized and still containing on average 0.5-1.3 epoxide groups per molecular unit, the resol component being composed of methylol compounds of oligomethylene compounds, which are additionally substituted by hydrocarbon or hydroxyalkyl or hydroxyaralkyl radicals, and the amine containing at least one primary or secondary amino group and at most 2 hydroxyl groups.The invention further relates to a process for the preparation of a binder and for the electrophoretic deposition of a cationic resin from an aqueous dispersion onto an article connected as the cathode and to an aqueous electrophoresis bath for carrying out this process.
    Type: Grant
    Filed: August 31, 1982
    Date of Patent: November 6, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Jurgen Ritz, Rolf Zimmermann
  • Patent number: 4440914
    Abstract: Solid epoxy resin systems comprising the reaction products of a polyepoxide compound with a functionality greater than two, a diglycidyl ether of a polyhydric phenol and a polyhydric phenol; said systems being applicable for use in a variety of applications and particularly in combination with phenolic novolac hardeners for molding applications.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: April 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: David Helfand, Ralph F. Sellers
  • Patent number: 4414250
    Abstract: Thermosetting resin coatings are provided which cure rapidly and exothermically at ambient temperatures. Accelerated crosslinking is accomplished by the reaction of oxalic acid esters with amine-containing polymeric compositions.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: November 8, 1983
    Assignee: Celanese Corporation
    Inventors: John R. Costanza, Louis E. Trapasso
  • Patent number: 4393179
    Abstract: A synthetic resin is in the form of a metal complex compound. The resin is the reaction product of:(a) Mannich bases which are free from epoxide groups; with(b) epoxide resins;wherein aliphatic hydroxyl groups originating from (a), (b), or a mixture thereof, are at least partially converted into urethane groups by reaction with partially blocked isocyanate, said Mannich bases (a) formed from components selected from:(a.sub.1) condensed phenols which are free from ether groups and contain at least two aromatic rings and at least two phenolic hydroxyl groups;(a.sub.2) condensed phenols which contain ether groups and contain at least two aromatic rings and at least two phenolic hydroxyl groups;(a.sub.5) formaldehyde or compounds which split off formaldehyde;(a.sub.3) secondary amines having at least one hydroxyalkyl group; and(a.sub.4) dialkylamines or dialkoxyalkylamines which do not contain free hydroxyl groups; or from the components:(a.sub.1) and (a.sub.2) with (a.sub.5) and (a.sub.3);(a.sub.1) with (a.sub.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: July 12, 1983
    Assignee: BASF Farben & Fasern A.G.
    Inventors: Karl Hoppe, Udo Strauss
  • Patent number: 4383073
    Abstract: Water-compatible compositions are described which consist essentially of at least one resinous compound whose backbone is linear or substantially linear and consists essentially of at least one oxyaryleneoxyalkylene or oxyaryleneoxy(1,3-(2-hydroxy)alkylene) unit and which bears at least two functional organic moieties through which cross-linking can occur (preferably groups having active hydrogen, more preferably aliphatic hydroxyl groups) and at least one terminal carbamoylpyridinium group covalently bonded through the ring nitrogen atom combined with an acid curable cross-linking agent. The compositions are useful coating compositions which find particular utility in cathodic electrodeposition. The compounds are prepared, for example, by reacting a linear or substantially linear epoxy resin with a carbamoylpyridine in the presence of sufficient amount of a Bronsted acid and water to stabilize the carbamoylpyridinium salt thus formed.
    Type: Grant
    Filed: August 20, 1981
    Date of Patent: May 10, 1983
    Assignee: The Dow Chemical Company
    Inventors: Ritchie A. Wessling, Larry D. Yats, William O. Perry
  • Patent number: 4374963
    Abstract: This invention relates to a heat curable composition comprising(a) a liquid, ethylenically unsaturated monomer, oligomer or prepolymer of the formula: ##STR1## wherein R is H or CH.sub.3, R.sub.1 is an organic moiety and n is at least 2,(b) an epoxy resin containing at least two ##STR2## groups, and (c) a thermal initiator member of the group consisting of(1) a substituted or unsubstituted diaryliodonium salt in combination with a free radical initiator,(2) a BF.sub.3 adduct,(3) a BF.sub.3 adduct in combination with a free radical initiator, and(4) dicyandiamide in combination with a free radical initiator.The system is stable at ordinary temperatures, but on heating the thermal initiator catalyzes the curing of the acrylate and the epoxy resin.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: February 22, 1983
    Assignee: W. R. Grace & Co.
    Inventors: Charles R. Morgan, David R. Kyle
  • Patent number: 4368299
    Abstract: A composition comprising an epoxy resin having at least two epoxy groups in the molecule and a hardener selected from the group consisting of (1) a resorcinol novolak having an unreacted resorcinol content of 10% by weight or less, (2) a mixed novolak of a resorcinol novolak and a monohydric phenol novolak having a total unreacted resorcinol and monohydric phenol content of 8% by weight or less, and (3) a resorcinol/monohydric phenol polycondensation novolak having a polycondensed resorcinol content of 30 mole % or more and a total unreacted resorcinol and monohydric phenol content of 8% by weight or less.The composition is useful for moldings, laminates, paints, and adhesives with excellent thermal resistance, durability and electrical characteristics.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: January 11, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuyoshi Watanabe, Makoto Andoh, Yasuhisa Saito, Yasuteru Maeda, Yoshiya Fukuyama
  • Patent number: 4343924
    Abstract: Disclosed is an improved method for coating a substrate with a film of a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary-amine catalyst. The pot life of the coating composition is substantially increased without deleterious loss of properties of the ultimately cured film wherein the coating composition comprises three components. The first component is a phenol-functional condensation product of (a) a phenol-aldehyde reaction product bearing a plurality of methylol and phenol groups, and (b) a polyol, polycarboxylic acid, or polyepoxide, wherein the condensation product is reacted with a selective transmethylolating agent for substantially transforming residual methylol groups into non-active hydrogen groups. The second component is a multi-isocyanate cross-linking agent and the third component is an organic solvent. The coating composition is applied to a substrate and cured by exposure of the coated substrate to a vaporous tertiary amine catalyst.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: August 10, 1982
    Assignee: Ashland Oil, Inc.
    Inventor: Gary L. Linden
  • Patent number: 4341681
    Abstract: Cationic solution addition copolymers of monoethylenically unsaturated copolymerizable monomers are described having Mannich base side chains with the structure: ##STR1## where R and R' are selected from C.sub.1 -C.sub.8 alkyl and C.sub.1 -C.sub.8 alkanol, or are together constituted by a C.sub.2 -C.sub.8 alkylene group. This copolymer is preferably reacted with a diepoxide in a stoichiometric deficiency with respect to the amine groups in the side chains. At least a portion of the tertiary amine groups are then reacted with a solubilizing acid to form a salt which enables the copolymer to be dissolved in water.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: July 27, 1982
    Assignee: De Soto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah, Aurelio J. Parenti
  • Patent number: 4246162
    Abstract: A moulding composition consisting of an epoxy resin adduct of a low molecular diglycidyl ether of bisphenols and an aromatic diamine together with a filler, an accelerator, and an aromatic polyol as hardener. Mouldings having excellent resistance to cracking can be obtained from this moulding composition.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: January 20, 1981
    Assignee: Ciba-Geigy Corporation
    Inventor: Bruno Schreiber