Organic Nitrogen Compound Contains Three Or More Nitrogen Atoms Other Than As Solid Polymer, E.g., Diethylene Triamine, Etc. Patents (Class 523/420)
  • Patent number: 5589049
    Abstract: The invention relates to a method of of coating electrically conductive substrates using cathodically depositable electrodip paints. The invention is notable in that the electrodip paints employed contain crosslinked polymer microparticles which can be prepared by reacting(A) a compound which contains on average more than 1.0 epoxide groups per molecule, or a mixture of such compounds, and(B) a compound which contains not only a group reactive toward epoxide groups but also at least one ketimine or aldimine group in the molecule, or a mixture of such compoundsto give a noncrosslinked intermediate product (C), which still contains on average at least one epoxide group per molecule, and dispersing this intermediate product in the presence of a Br onsted acid in an aqueous medium.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: December 31, 1996
    Assignee: BASF Lacke +Farben, AG
    Inventors: G unther Ott, Hardy Reuter, Walter Jouck, Susanne Piontek, Ulrich Heimann, John Gilbert
  • Patent number: 5569687
    Abstract: A multi-component waterborne corrosion resistant coating composition used as an organic zinc rich primer for protecting metal substrate from corrosion. The composition includes zinc dust, a crosslinking component and a polymeric component produced from a low Tg polymer and an amine functional curing agent. These components of the composition are stored separately and then mixed prior to applying the coat of the composition over metal substrate.The coating composition of the present invention has longer pot life than conventional waterborne corrosion resistant coating composition.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: October 29, 1996
    Assignee: Rohm and Haas Company
    Inventors: Timothy P. Sanborn, Joseph M. Beno, Jr., Roy W. Flynn
  • Patent number: 5567748
    Abstract: A water miscible or soluble amine terminated resin useful as a curing agent comprising the reaction product of: A) a polyamine component comprising one or more hydrophilic poly(oxyalkylene) amines, and optionally one or more hydrophobic polyamines; B) a polyepoxide component comprising one or more diglycidyl ethers of a polyalkylene glycol, one or more diglycidyl ethers of a cycloalkylene glycol and optionally one or more hydrophobic polyglycidyl ethers, wherein the mixture is optionally advanced by an amine extender; C) optionally, a reactive diluent which is capable of reacting with an epoxy resin, and D) optionally, a catalyst for the reaction of an amine with an epoxy resin; wherein Component A is employed in an equivalent excess with respect to Component B such that the terminal moieties of the reaction product are amine moieties capable of reacting with an epoxy resin; the composition has an amine hydrogen equivalent weight of from 140 to 240; and the composition is water soluble or water miscible.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: October 22, 1996
    Assignee: The Dow Chemical Company
    Inventors: Dieter H. Klein, Hans J. Wessely
  • Patent number: 5559086
    Abstract: In one embodiment, an epoxy resin composition is provided comprising: an epoxy resin and a partially reduced aromatic amine hardening agent. In another embodiment, a well treating composition is provided comprising: an epoxy resin; a partially reduced aromatic amine hardening agent; a solid particulate material; and a carrier fluid. In yet another embodiment, a method of treating a subterranean formation is provided. The inventive method comprises the step of placing the inventive well treating composition into the formation.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: September 24, 1996
    Assignee: Halliburton Company
    Inventors: Brahmadeo Dewprashad, Jimmie D. Weaver
  • Patent number: 5491204
    Abstract: Barrier materials for reducing the permeability of plastic packaging materials are provided, characterized as containing at least about seven percent by weight amine nitrogen, or a total of at least about 17 percent amine nitrogen plus hydroxyl groups. The barrier materials exhibit oxygen permeability of less than about 1.5 cc-mil/100 in.sup.2 -day-atmosphere and a carbon dioxide permeability of less than about 15 cc-mil/100 in.sup.2 -day-atmosphere at 23.degree. C. and zero percent relative humidity. The barrier material is formed from a polyepoxide, a polyamine and an alkanolamine. Optionally the polyamine may comprise prereacted polymeric resin formed from a polyepoxide and a polyamine. Multilayer packaging materials and multilayer containers including the polyamine-polyepoxide barrier material are part of the invention.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: February 13, 1996
    Assignee: PPG Industries, Inc.
    Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
  • Patent number: 5385962
    Abstract: An electrodepositable primer composition having improved delamination resistance with regard to automotive topcoats is disclosed. The composition is particularly useful in conjunction with topcoats which transmit ultraviolet radiation. The composition includes an ionic resin and a hindered amine light stabilizer (HALS) which is preferably a hindered aminoether light stabilizer. A preferred hindered aminoether light stabilizer is bis-(1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl)sebacate. The invention also includes a process for coating a substrate by applying the above-described primer composition and subsequently applying a topcoat. The process can alternatively include applying a standard primer composition to a substrate and subsequently applying a HALS compound to the electrodeposited substrate.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: January 31, 1995
    Assignee: PPG Industries, Inc.
    Inventors: Victor G. Corrigan, Gerald W. Gruber, Michael A. Polack, Robert R. Zwack
  • Patent number: 5371119
    Abstract: A process for the preparation of polyether polyamines comprising the steps ofA) reacting a polyol with an epihalohydrin in the presence of a catalyst;B) adding an at least equimolar quantity of an aqueous alkali metal hydroxide, based on the weight of catalyst, to the reaction mixture formed in step A);C) distilling volatile constituents from the reaction mixture from step B) at a temperature below about 150.degree. C. and under a pressure below about 1.33.times.10.sup.4 Pa.;D) filtering the reaction mixture remaining after step C) at a temperature in the range of from about 80.degree. C. to about 100.degree. C. to remove insoluble components thereof from the bishalohydrin reaction product; andE) reacting the bishalohydrin reaction product with ammonia and/or an amine in the presence of an alkaline catalyst to form a polyether polyamine.
    Type: Grant
    Filed: January 26, 1993
    Date of Patent: December 6, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Ralf Bohlander, Guenter Uphues, Uwe Ploog
  • Patent number: 5358982
    Abstract: Crosslinked polymer microparticles based on epoxy resin obtained by polymerization of aqueous dispersions (A) of compounds containing epoxide groups in the presence of up to 0.2 mol, preferably 0.02 to 0.15 mol (based on the nitrogen contained in (B)) of a nitrogen-containing organic compound (B) per epoxide equivalent and subsequent isolation which are preferably in the form of aqueous dispersions thereof, and are suitable as organic fillers, pigments, matting agents and/or reinforcing agents for binder systems and individual components thereof, paint formulations, coating and molding compositions, intermediate coatings, adhesives and the like, preferably based on water.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: October 25, 1994
    Assignee: Hoechst Aktiengesellschaft AG
    Inventors: Joerg-Peter Geisler, Stefan Petri
  • Patent number: 5356961
    Abstract: There is disclosed an aqueous epoxy resin composition which comprises an epoxy resin; an amidoamine obtained by the reaction of a carboxylic acid with a polyamine compound represented by the general formula (I) ##STR1## wherein n is an integer of 0 or 1 or greater indicating the number of the repeating units which compound is obtained by the reaction of epichlorohydrin with xylylenediamine, especially m-xylenediamine; and water. The above-mentioned epoxy resin composition can be utilized in a wide variety of industrial applications such as a coating material used for the purpose of anticorrosion or decoration, an adhesive for civil and building work or the like.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: October 18, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshiaki Nishimura, Kiichiro Seki, Yasushi Ohnuma
  • Patent number: 5354366
    Abstract: An amine functional water reducible resin and an ink composition incorporating an amine functional water reducible resin which is water insoluble under certain pH conditions and selectively water washable under certain other pH conditions. The method aspect of the present invention relates to a method of making, using and recovering the ink composition and a method of making the water reducible resin.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: October 11, 1994
    Assignee: Deluxe Corporation
    Inventors: Thomas J. Pennaz, Paul F. Schacht
  • Patent number: 5354789
    Abstract: An aqueous resin dispersion containing as an aqueous resin component a polyamide-modified epoxy-polyamine resin comprising a reaction product of a phenolic hydroxyl group-terminated polyamide compound obtained by the reaction of a polyamine compound containing at least two primary and/or secondary amino groups in a molecule and having a number average molecular weight of 40 to 8,000, a polycarboxylic acid having a number average molecular weight of 100 to 8,000 and a compound containing at least one phenolic hydroxyl group and one carboxyl group in a molecule, a bisphenol compound and a bisphenol diglycidyl ether compound, and an active hydrogen-containing amine compound. Said aqueous resin dispersion is excellent in corrosion resistance and especially suited for use in cathodic electrodeposition coating.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: October 11, 1994
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Koji Kamikado
  • Patent number: 5348635
    Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.
    Type: Grant
    Filed: February 3, 1993
    Date of Patent: September 20, 1994
    Assignee: BASF Corporation
    Inventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
  • Patent number: 5331026
    Abstract: The present invention is directed to a process for producing an aqueous cathodic electrocoating composition comprisingA) mixingi) a powder comprising a dispersion of a pigment in a solid resinii) a principal resiniii) a crosslinker and optionallyiv) an additive selected from the group consisting of organic solvents, catalysts, wetting agents, conditioning agents, thickeners, rheology control agents, antioxidants, surfactants, leveling agents and mixtures thereofB) salting with an acid andC) dispersing in deionized water.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: July 19, 1994
    Assignee: BASF Corporation
    Inventors: James W. Benefiel, Peter D. Clark, Laura M. Lanni
  • Patent number: 5321062
    Abstract: A substituted alkoxy benzene having the formula ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are each a hydrocarbon radical having from 1 to 8 carbon atoms and x is 0 or 1 is provided. The substituted alkoxy benzene is very useful as a wetting aid for enhancing the ability of hardenable polyepoxide resin compositions to coat and bond to material (e.g., particulate material) in high temperature applications. The substituted alkoxy benzene does not significantly accelerate the curing rate of the resins. A polyepoxide resin composition for coating and bonding to a material, a composition useful for forming a hard permeable mass in a remote location and a method of continuously forming and suspending consolidatible resin composition coated particulate material in a gelled aqueous carrier liquid and transporting the coated particulate material to a remote location where the material is consolidated are also provided.
    Type: Grant
    Filed: October 20, 1992
    Date of Patent: June 14, 1994
    Assignee: Halliburton Company
    Inventors: Bruce E. Landrum, Jimmie D. Weaver, Joseph R. Murphey
  • Patent number: 5319004
    Abstract: Hardeners for epoxy resins, comprising reaction products of(A) polyamidoamines that were obtained by polycondensation of (a) dicarboxylic acids containing oxyalkylene groups, or their derivatives, with (b) polyamines containing at least two amino groups capable of undergoing condensation with (a),(B) polyamines containing at least two secondary amino groups, and(C) adducts of (c) polyepoxy compounds and (d) polyalkylene polyether polyols.Epoxy resins that have been cured with these hardeners exhibit in particular a very good water resistance.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: June 7, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Marten, Bernhard Stengel-Rutkowski, Claus Godau
  • Patent number: 5300541
    Abstract: Barrier materials for reducing the permeability of plastic packaging materials are provided, characterized as containing at least about seven percent by weight amine nitrogen, or a total of at least about 17 percent amine nitrogen plus hydroxyl groups. The barrier materials exhibit oxygen permeability of less than about 1.5 cc-mil/100 in.sup.2 -day-atmosphere and a carbon dioxide permeability of less than about 15 cc-mil/100 in.sup.2 -day-atmosphere at 23.degree. C. and zero percent relative humidity. The barrier material can be formed from polyepoxide and polyamine. Optionally the polyamine may comprise prereacted polymeric resin formed from a polyepoxide and a polyamine. Multilayer packaging materials and multilayer containers including the polyamine-polyepoxide barrier material are part of the invention.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: April 5, 1994
    Assignee: PPG Industries, Inc.
    Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
  • Patent number: 5298538
    Abstract: Plasticizing resins, aqueous dispersions of cationic resins, and methods of making the same for use in cathodic electrodeposition are disclosed. The resins are formed from reacting a polyoxyalkylenepolyamine, a phenol, and a formaldehyde. The reactants may further include a block building unit derived from a polyepoxide. When used in combination with other conventional electrodepositable resins, deposited films with improved mechanical properties and descreased tendency toward cratering are obtained.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: March 29, 1994
    Assignee: BASF Corporation
    Inventors: Klaus Cibura, Yali F. Hallock, John A. Gilbert, John D. McGee
  • Patent number: 5227414
    Abstract: An ambient temperature-curing aqueous urethane-epoxy emulsion coating composition is provided comprising an essentially organic solvent-free emulsion in water of:(a) a urethane oligomer, terminated with primary amine functional groups which are reactive with epoxides, said oligomer being the reaction product of an isocyanate-terminated polyurethane prepolymer and a mono- or polyketimine compound containing one other functional group bearing a single active hydrogen atom which reacts with the isocyanate groups to yield a ketimine-terminated urethane oligomer, said ketimine-terminated urethane oligomer being emulsified into the water by conversion of the ketimine groups into primary amine groups and formation of acid salt of 25-50% of the amine groups by a volatile organic acid; and(b) a polyepoxide in an amount sufficient to provide a ratio of total primary amino group hydrogen atoms to epoxide groups of about 0.9 to 2.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: July 13, 1993
    Assignee: Tennant Company
    Inventors: G. Dale Ernst, Joseph S. Keute, Alan R. Schuweiler
  • Patent number: 5219914
    Abstract: A washout resistant roof mastic is disclosed in which an emulsion is applied and contacted with a second material that causes the emulsion to flocculate and set quickly. The emulsion can be applied for example through an applicator that simultaneously applies the emulsion and the flocculant.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: June 15, 1993
    Assignee: Rohm and Haas Company
    Inventor: Charles E. Warburton, Jr.
  • Patent number: 5177122
    Abstract: This invention relates to stable one-part latex compositions prepared by aqueous emulsion polymerization wherein a core-shell polymer is found, the core formed by emulsion polymerization of an ethylenically unsaturated monomer in the presence of an epoxy resin and the shell polymer formed by emulsion polymerization of a hydroxy carboxyl containing monomer composition in the presence of the core, providing that the monomers in both the core and the shell do not contain amino functional groups, and post-adding to the formed core-shell polymer an organic compound having at least one amino functional group which is available for later reaction with the epoxy resin upon drying to produce a crosslinked polymer product.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: January 5, 1993
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Yen-Jer Shih
  • Patent number: 5177125
    Abstract: A two-phase cathodic electrocoat is obtainable by coating an electrically conducting substrate with a mixture containingA) an aqueous cationic dispersion of a polycondensation or polyaddition product,B) an aqueous cationic dispersion of a polycondensation or polyaddition product having a glass transition temperature of from -80.degree. to 20.degree. C., the polymers of dispersions (A) and (B) being mutually incompatible, and C) optionally a crosslinking agent, a pigment paste, auxiliaries and/or additives, and then baking.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: January 5, 1993
    Assignee: BASF Lacke & Farben Aktiengeselllschaft
    Inventors: Thomas Schwerzel, Hans Schupp, Klaus Huemke, Ulrich Heimann
  • Patent number: 5171765
    Abstract: This application describes a water dispersible polymeric vehicle comprising epoxy polymers having about 5 to 50 weight percent mesogens or a cross-linkable blend of an amine salt of a mesogenic carboxylic acid, cross-linker resin and an epoxy polymer, the mesogenic acid providing about 5 to 50 weight percent mesogenic groups to the blend.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: December 15, 1992
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
  • Patent number: 5147905
    Abstract: Advanced resins and unadvanced epoxy resins are disclosed wherein the unadvanced compound and at least a portion of the advanced epoxy resin contains at least one --O--R.sup.1 --O-- or --(O--CH.sub.2 --CHR.sup.2).sub.n --O-- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula ##STR1## or (4) a group represented by the formula ##STR2## Also disclosed are nucleophilic derivatives thereof, as well as curable compositions and coating compositions containing the advanced or unadvanced epoxy resins or nucleophilic modified advanced or unadvanced epoxy resins. These advanced resins and unadvanced epoxy resins provide coatings with good flexibility or formability as exhibited by good flexural or formable properties determined by reverse impact, T-bend and wedge-bend tests, chip resistance, and with good corrosion resistance and throwpower.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: September 15, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
  • Patent number: 5135970
    Abstract: The invention relates to the use of crosslinked polymer microparticles having an average particle size of at most 5 .mu.m and a glass transition temperature (Tg) of at least +30.degree. C. in aqueous paint preparations as filler and/or as partial substitute of white pigments, in particular of titanium dioxide.Among other things, the corresponding paints show increased spreading power, less tendency for sedimentation and reduced crater formation.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: August 4, 1992
    Assignee: Hoechst AG
    Inventors: Michael Honel, Gerd Walz, Peter Ziegler, Uwe Kubillus
  • Patent number: 5130004
    Abstract: A pigment paste suitable for use in cationic electrodeposition is disclosed. The pigment paste comprises a cationic resinous grinding vehicle derived from an epoxy resin containing both quaternary ammonium and ternary sulfonium salt groups. Also disclosed are cationic electrodeposition paints containing the pigment paste and the use of these paints in the process of cationic electrodeposition. The paste improves the stability of lead-containing cationic electrodeposition paints.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: July 14, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Mark W. Johnson, Gregory J. McCollum
  • Patent number: 5116887
    Abstract: An amine-epichlorohydrin resin is prepared in a water-polyol solvent in order to facilitate the polymerization and crosslinking reactions. The reaction product is useful as a wet strength resin composition which has a flash point high enough to be used in commercial paper making operations.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: May 26, 1992
    Assignee: Henkel Corporation
    Inventors: Stephen A. Fischer, Reuben H. Grinstein
  • Patent number: 5108575
    Abstract: Disclosed herein is a cathodic electrodepositable resin containing polyamine enamine. It has been discovered that reacting epoxy resins with polyamine enamine is a viable method of introducing amine functionality to the epoxy resin. The polyamine enamine route results in the desired high pH and stable dispersion in the electrocoat bath.
    Type: Grant
    Filed: August 8, 1990
    Date of Patent: April 28, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Tapan K. Debroy
  • Patent number: 5095051
    Abstract: An improved electrodepositable cationic resin is disclosed. Prior art electrodepositable cationic resins are formed from polyepoxides which are chain extended with polyether or polyester polyols to internally flexibilize the resin. Our polyepoxide resin is chain extended with amide diol which gives a resin which is hydrolytically stable and does not tend to absorb moisture.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: March 10, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Tapan K. Debroy, Robert A. Tessmer
  • Patent number: 5089100
    Abstract: Disclosed herein is a method of incorporating amine functionality onto a polyepoxy resin to be used for cathodic electrocoat. This method has the following steps:a) reacting an epoxy resin with an amount of secondary amine so that unreacted epoxy functional groups remain; andb) further reacting the reaction product of a) with a polyamine so that there is a minimum of one equivalent of epoxy for every mole of polyamine. This method results in an electrocoat bath with the desired high pH and a stable dispersion.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: February 18, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: / Tapan K. Debroy, Ding Y. Chung
  • Patent number: 5086090
    Abstract: The invention relates to a process for the preparation of aqueous dispersions to be further processed to electrocoating paints with baking temperatures below 160.degree. C. and baking times.ltoreq.30 minutes, which dispersions contain modified epoxide-amine adducts as binders and polyisocyanates blocked by hydroxyl groups as cross-linking agents.In this process polyepoxides and compounds containing one or more, preferably 2, hydroxyl groups per molecule are reacted at elevated temperatures in the presence of catalysts to furnish epoxide-containing intermediates.A solvent or a mixture of solvents is then added with external cooling ahd the solution is boiled under reflux, if necessary in vacuo, until the temperature of the solution drops to 95.degree. C. to 20.degree. C.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: February 4, 1992
    Assignee: BASF Lacke & Farben AG
    Inventors: Michael Geist, Klaus Cibura, Walter Jouck, Gunther Ott, Jurgen Sadlowski, Manfred Dangschaft, Manfred Reimann
  • Patent number: 5066689
    Abstract: The invention relates to an aqueous coating agent which contains an organic synthetic resin binding agent which can be made dilutable with water by protonization with acids, containing crosslinking agents and a synthetic resin component containing organic amino groups and hydroxyl groups, and, in some cases, crosslinking catalysts and, if desired, pigments, fillers, corrosion inhibitors or anticorrosives, conventional lacquer adjuvants, and, in some cases, organic solvents in an amount up to 10% of the total weight of the coating agent.
    Type: Grant
    Filed: August 28, 1990
    Date of Patent: November 19, 1991
    Assignee: Herberts GmbH
    Inventors: Hans-Peter Patzschke, Armin Goebel
  • Patent number: 5057557
    Abstract: Epoxy resins are modified by reaction with an acidified polytertiary amine-containing compound. These modified epoxy resins when cured result in products having improved properties.
    Type: Grant
    Filed: May 11, 1990
    Date of Patent: October 15, 1991
    Assignee: The Dow Chemical Company
    Inventors: Duane S. Treybig, Pong S. Sheih, John M. McIntyre
  • Patent number: 5057559
    Abstract: Cationic paint binders based on the reaction products of epoxide compounds with substituted carbamic acid derivatives and the use thereof in the formulation of cathodically deposited paints are described. The carbamic acid derivatives are urethanes, ureas, allophanates, and biuret compounds. Crosslinking functionality and/or protonatable groups are introduced by a suitable selection of blocking agents for the isocyanate compounds utilized. The reaction between the epoxide compounds and carbamic acid derivatives takes place in the presence of basic groups under relatively mild conditions; and, even when several carbamic acid moieties are present in a molecule, a readily soluble product is obtained.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: October 15, 1991
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Rudolf Schipfer
  • Patent number: 5039720
    Abstract: An aqueous electrophoretic coating material, which can be deposited at the cathode and contains(A) 90 to 50% by weight, based on the total portion of synthetic resin vehicle, of one or several polycondensation, polymerization and/or poly-addition resins, the resin or, in the event that several resins are present, their mixture(a) having a number average molecular weight (Mn) of 700 to 10,000(b) having 1.2.times.10.sup.23 to 21.7.times.10.sup.23 lateral or terminal double bonds per 1,000 g, corresponding to a hydrogenation iodine number of 5 to 90,(c) optionally containing primary and/or secondary hydroxyl groups, corresponding to a hydroxyl number of 0 to 450 mg KOH/g of resin, and(d) tertiary amino groups corresponding to an amine number of 30 to 450 mg KOH/g of resin.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: August 13, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dietrich Saatweber, Georg Hendriux, Gerhard Brindopke, Helmut Plum
  • Patent number: 5021471
    Abstract: Epoxy resins are modified by reaction with a pyridine compound and a Bronsted acid. These modified epoxy resins when cured result in products having improved properties.
    Type: Grant
    Filed: May 11, 1990
    Date of Patent: June 4, 1991
    Assignee: The Dow Chemical Company
    Inventor: Duane S. Treybig
  • Patent number: 5017675
    Abstract: Use of polyamidoamines as curing agents for epoxy resins and curable mixtures containing these substances.The invention relates to the use of polyamidoamines (A) containing primary and/or secondary amino groups as curing agents for epoxy-containing compounds (B), wherein the polyamidoamines (A) used are those compounds which have been obtained by polycondensation of (a) compounds from the group of dicarboxylic acids containing oxyalkylene groups, or derivatives thereof (esters), with (b) polyamines containing at least two amino groups which are condensable with (a).The invention furthermore relates to curable mixtures containing the abovementioned components (A) and (B). The cured products obtainable according to the invention have advantages with regard to impact strength and shock resistance, to flexibility even at relatively low temperatures and crack-bridging properties.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: May 21, 1991
    Assignee: Hoechst AG
    Inventors: Manfred Marten, Claus Godau, Heinz Schmelzer
  • Patent number: 5015671
    Abstract: A thermosetting, powder coating composition is disclosed which comprises an epoxy resin, a nitrogen-containing curing agent and an inorganic filler consisting essentially of aluminum hydroxide and silica, the weight ratio of the aluminum hydroxide to the silica being 1:4 to 4:1 and the filler being used in an amount of 40-300 parts by weight per 100 parts by weight of the epoxy resin.
    Type: Grant
    Filed: December 29, 1989
    Date of Patent: May 14, 1991
    Assignee: Somar Corporation
    Inventors: Kazuya Ono, Tetsuo Miyake, Katsuji Kitagawa
  • Patent number: 5015672
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 300 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amino group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: May 14, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 5015673
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 300 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amino group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: May 14, 1991
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 4999388
    Abstract: Branched polyester resins comprising a polyepoxy compound, a hindered phenol and a catalyst compound having enhanced melt viscosity are disclosed.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: March 12, 1991
    Assignee: General Electric Company
    Inventor: Kevin T. Okamoto
  • Patent number: 4987163
    Abstract: The invention relates to a stable epoxy resin dispersions and also a process for the preparation thereof and the use thereof, in particular for coatings. The epoxy resin dispersions which are remarkable, in particular, for good storage stability with a low content of organic solvents at the same time and little tendency to skin formation and yield coatings with good surface properties, contain, in addition to water, optionally small quantities of organic solvents and also optionally usual additives, as an essential constituent a condensation product of(a) 50 to 80% by weight of an epoxy compound containing at least two epoxy groups per molecule and having an epoxy equivalent to of 100 to 2,000.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: January 22, 1991
    Assignee: Hoechst AG
    Inventors: Wilhelm Becker, Claus Godau, Dieter Dreischhoff
  • Patent number: 4980398
    Abstract: Disclosed herein is a cathodic electrodepositable resin containing polyamine enamine. It has been discovered that reacting epoxy resins with polyamine enamine is a viable method of introducing amine functionality to the epoxy resin. The polyamine enamine route results in the desired high pH and stable dispersion in the electrocoat bath.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: December 25, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Tapan K. Debroy
  • Patent number: 4977203
    Abstract: A coating resin composition comprising, as a coating-forming resin binder, an epoxy resin derivative containing a functional group represented by the following formula ##STR1## wherein R.sub.1 represents a hydrogen atom or methyl group; each of R.sub.2 and R.sub.3 represents a C.sub.1 -C.sub.5 alkyl group independently of the other;R.sub.4 represents a C.sub.2 -C.sub.6 alkylene group in which an ether group (--O--) may be present in the carbon chain; andn represents an integer from 1 to 6.This coating resin composition is useful for cathodic electrodeposition coating.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: December 11, 1990
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Michiharu Kitabatake
  • Patent number: 4968730
    Abstract: Preparation of pigment paste resins for cathodically depositable coating compositions based on epoxy resin-amine adducts obtained from unmodified or modified epoxy resins, which by partial or complete reaction of secondary amino groups with formaldehyde contain oxazolidine structures; whose tertiary amino groups introduced via primary-tertiary diamines are quaternized to at least 20 mol % using an organic acid and a monoglycidyl compound and which in a solution adjusted with water to a correct application viscosity contain a total of 80 to 100 millimoles of acid per 100 g of solid resin are described. The pigment pastes possess, both in concentrated and dilute form, a stability which meets practical requirements and, because of their rheology, are readily processed to ensure formation of defect-free films both during deposition and crosslinking by stoving. The applied films have good properties.
    Type: Grant
    Filed: September 21, 1989
    Date of Patent: November 6, 1990
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Helmut Honig, Georg Pampouchidis, Herbert Matzer
  • Patent number: 4959398
    Abstract: A powdery adhesive comprised of spherical particles comprising 40 to 90 parts by weight of an epoxy resin component, 10 to 60 parts by weight of a rubber component and a latent curing agent contained inside the particles, the average particle size of the particles being from 0.1 to 500 .mu.m. The powdery adhesive may be prepared by a process comprising a step of preparing a compatible mixture comprising an epoxy resin component, a rubber component and a common organic solvent, a step of emulsifying or suspending the compatible mixture in an aqueous medium to form spherical particles, and a step of causing a phase separation of the epoxy resin component and the rubber component in the spherical particles.
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: September 25, 1990
    Assignee: Toray Industries, Inc.
    Inventors: Koichiro Oka, Ikuo Hagiwara
  • Patent number: 4956402
    Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 200 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amimo group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: September 11, 1990
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
  • Patent number: 4933381
    Abstract: A resin compatible size composition for glass fibers having a small fiber diameter is disclosed. The size contains a film former, a nonionic lubricant, a cationic lubricant, at least one silane coupling agent and at least one acid, such as acetic or citric acid. The sized glass fibers are compatible with epoxy and polyester resins and are useful in producing yarns which are then braided, twisted or woven to form structural reinforcements.
    Type: Grant
    Filed: August 27, 1987
    Date of Patent: June 12, 1990
    Assignee: Owens-Corning Fiberglas Corporation
    Inventor: Thomas P. Hager
  • Patent number: 4891111
    Abstract: Cationic electrocoating compositions comprising a cationic electrodepositable resin and particular hydroxyl-free, alkylated polyethers dispersed in an aqueous medium are disclosed. Due to the presence of the polyethers, the compositions electrodeposit at high film builds with good smoothness. However, the polyethers do not result in detrimental effects with regard to the properties of the compositions such as rupture voltage and corrosion resistance of the resultant electrodeposited film. Also, the particular polyethers readily incorporate in the electrodeposition bath, are non-volatile and do not significantly build up in the electrodeposition bath during the electrodeposition process.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: January 2, 1990
    Assignee: PPG Industries, Inc.
    Inventors: Gregory J. McCollum, Robert R. Zwack, Roger L. Scriven
  • Patent number: 4853437
    Abstract: This invention relates to a novel composition comprising a water- and caustic-insoluble, inswellable, fibrous, particulate polymer comprising cross-linked units of a water-soluble polymer and a water-soluble cationic poly(diallylamine)-epichlorohydrin resin. This polymer is useful as an exchange resin, tablet disintegrant, thickener and suspending aid.
    Type: Grant
    Filed: March 4, 1988
    Date of Patent: August 1, 1989
    Assignee: Hercules Incorporated
    Inventors: Carl A. Lukach, Arjun C. Sau
  • Patent number: 4816502
    Abstract: A composition is provided comprising an epoxy resin, a nitroparaffin and a sulfonic acid. The presence of the sulfonic acid retards gellation of nitroparaffin-containing epoxy resin compositions intended for use in water-dispersible coating formulations cured with modified polyamine resins.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: March 28, 1989
    Assignee: Shell Oil Company
    Inventor: John A. Lopez