Two Or More Organic Nitrogen Compounds As Reactants Patents (Class 523/417)
  • Patent number: 5039787
    Abstract: Methods are disclosed for the production of (I) a cationic water-soluble resin by the reaction of a polyethylene glycol polyhalohydrin ether resulting from the reaction between polyethylene glycol and an epihalohydrin with an aziridine compound and (II) and (III) cationic water-soluble resins by the reaction of (I) the resin with an epihalohydrin and/or a polyfunctional epoxy compound in the presence or absence of a polyalkyleneimine. The resins (I), (II), and (III) are stable over a wide range of pH value and are useful as a water-treating agent.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: August 13, 1991
    Assignee: Nippon Shokubai Kagaku Kogyo, Co., Ltd.
    Inventors: Yasumasa Tanaka, Shigehiro Nishimura, Masatoshi Kurahashi, Yugi Sugiura, Yoshinori Sano
  • Patent number: 5034251
    Abstract: A dimensionally heat-recoverable article carrying a heat curable adhesive coating on a surface thereof, the adhesive coating comprising (a) a mixture of substantially solid particles of a first reactive component with separate substantially solid particles of at least a second reactive component and (b) a water soluble polymeric binder having substantially no hydroxyl groups, the first and second reactive components being present in the adhesive coating as substantially unreacted separate particles capable of reacting together to effect curing when the article is heated to its heat recovery temperature.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: July 23, 1991
    Assignee: Raychem Limited
    Inventors: Michael J. Read, Michael R. Read, Stephen J. Osborne, Geoffrey P. Hakes
  • Patent number: 5034435
    Abstract: The present invention is directed to an aqueously dispersed, ambient temperature curable composition containing(a) an epoxy resin which is rendered water-dispersible by chemically incorporated emulsifiers and/or by being admixed with external emulsifiers and(b) an isocyanate-terminated prepolymer(i) which is rendered water-dispersible by chemically incorporated emulsifiers and/or by being admixed with external emulsifiers,(ii) which is prepared from a mixture containing a polyisocyanate and a compound having a molecular weight of at least 500 and at least two hydroxyl groups and(iii) wherein the isocyanate groups are blocked with a phenolic compound.The present invention is also directed to a process for preparing polyurethanes by reacting the above blends with polyamines at ambient or elevated temperature and to the polyurethanes produced therefrom.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: July 23, 1991
    Assignee: Mobay Corporation
    Inventors: Edward P. Squiller, Peter H. Markusch
  • Patent number: 5032629
    Abstract: Novel hardening agents for epoxy compounds which are produced by reaction of polyalkylene, polyether amines having a mean molecular weight of 148 to 5,000 with di and/or polyepoxy compounds to a preliminary product, the ratio of the hydrogen atoms possibly remaining after reaction with monoepoxy compounds and bound to nitrogen and which are capable of reaction with epoxide groups, to epoxide groups of diepoxy compounds or polyepoxy compounds in the range of 1:1.4 to 6, and reaction of this preliminary product with a primary or secondary amine, the employed amine or amine mixture being used in an amount such that the ratio of epoxide groups capable of reaction to hydrogen atoms attached to nitrogen is 1:2 to 10.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: July 16, 1991
    Assignee: Rutgerswerke AG
    Inventors: Achim Hansen, Alfred Mathes, Jurgen Zehrfeld
  • Patent number: 5019606
    Abstract: Aqueous solutions of polyamidoamine-epichlorohydrin resins and preparation and use thereof.A stable aqueous resin solution having a pH of not more than 7 and containing as the resin a water-thinnable polyamidoamine-epichlorohydrin resin (A) obtained by reaction of a water-thinnable basic polyamidoamine (B) comprising an acid component (B.sub.1) and an amine component (B.sub.2) with epichlorohydrin (C), the level of organically bound chlorine in the resin (A) being not more than 4% by weight.The present invention further relates to a process for preparing these products and to the use thereof in particular for increasing the wet strength of paper.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: May 28, 1991
    Assignee: Hoechst AG
    Inventors: Manfred Marten, Walter Kamutzki
  • 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: 5008351
    Abstract: Self-crosslinking cationic paint binders based on ureide-modified epoxy resins; the preparation of these binders and their use, particularly in electrodeposition paints, is described. The modification is effected with carboxylic compounds carrying ureide groups, blocked isocyanate groups and, optionally, tertiary amino groups. The carboxylic compounds are obtained through reaction of dicarboxylic acid anhydrides or compounds carrying dicarboxylic acid anhydrides with a substituted urea or a substituted biuret. The products show excellent resistance and adhesion characteristics.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: April 16, 1991
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 4992525
    Abstract: Cationic resins based on epoxy resins which are modified through the introduction of phosphoric acid segments and the process of producing the resins are described. The reaction of the phosphoric acid is carried out in a multiple-step process whereby, in a first step, the diester is formed through reaction of ortho-phosphoric acid with 2 moles of a monoepoxy compound or through reaction of a polyphosphoric acid with n-1 moles of a monoalcohol and subsequent reaction with n+1 moles of a monoepoxy compound. The remaining acid group is reacted with a di- or polyepoxy resin. The products obtained can still contain unreacted epoxy groups. The protonable groups are introduced via the epoxy groups and/or via the hydroxy groups present or set free by opening of the oxirane ring. The binders can be combined with hardening components or may be formulated as self-crosslinking binders. The binders have excellent resistance to corrosion when stoved as electrodeposited coatings.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: February 12, 1991
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Ingo Kriessmann, Willibald Paar
  • Patent number: 4980397
    Abstract: A method for preparing an advanced epoxy cationic resin from an opoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electro-deposition are prepared from the product obtained by the process.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: December 25, 1990
    Assignee: The Dow Chemical Company
    Inventors: Nancy A. Rao, Richard A. Hickner
  • Patent number: 4980399
    Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes, the said binders containing latent primary amino groups. In order to prepare the binders, an epoxy resin is reacted with a polyamine, which in addition to a sterically hindered primary amino group also contains at least one primary amino group blocked by reaction with a ketone or aldehyde, and, if appropriate, further primary or secondary amines.
    Type: Grant
    Filed: February 5, 1990
    Date of Patent: December 25, 1990
    Assignee: BASF Lacke & Farben AG
    Inventors: Michael Geist, Gunther Ott, Georg Schon
  • 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: 4977202
    Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a digylcidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electrodeposition are prepared from the product obtained by the process.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: December 11, 1990
    Assignee: The Dow Chemical Company
    Inventors: Nancy A. Rao, Richard A. Hickner
  • Patent number: 4977201
    Abstract: The present invention provides a polyvinyl chloride plastisol composition characterized by containing a specified epoxy resin, a blocked isocyanate and, if necessary, a latent curing agent for an epoxy resin as tackifiers. This plastisol composition is excellent in storage stability and can strongly adhere to various metals and various undercoate of metals (such as electro-deposit) by baking even at a relatively low temperature to give a coating which is free from blowing and exhibits excellent adhesion after the immersion in hot water or the heating. Therefore, the composition is useful as a body sealer or undercoat for an automotive body.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: December 11, 1990
    Assignees: Asahi Denka Kogyo K.K., A,C,R. Co., Ltd.
    Inventors: Akio Ogawa, Masahiko Shimada, Kazuhiko Ando
  • Patent number: 4973613
    Abstract: Cathodically depositable electrodeposition paints contain binder combinations of cationic film-forming resins with organic titanium compounds which are obtained by reacting tetraalkyl orthotitanates or titanium acetyl acetonates with NH-functional .beta.-hydroxyalkylamine compounds, subsequently reacting with formaldehyde and with removal of the alcohol and/or acetyl acetone formed. The stoved paint films exhibit an excellent anti-corrosion effect on non-pretreated sheet steel.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: November 27, 1990
    Assignee: Vianova Kunstharz A.G.
    Inventor: Willibald Paar
  • 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: 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: 4933379
    Abstract: A process is disclosed for preparing an aqueous paint composition including the steps of(a) mixing a pigment powder having a particle size less than about 20 micrometers, a cross-linking agent and an epoxy resin to form a liquid, solvent-free paste;(b) reacting the resultant paste with a secondary amine to provide at least one N-H function per epoxy group of the epoxy resin; and(c) neutralizing the resulting suspension of particles coated with an epoxy-amine adduct and a cross-linking agent.Also provided is a coating process employing the invention aqueous paint composition containing a transesterification-promoting metal compound.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: June 12, 1990
    Assignee: Shell Oil Company
    Inventors: Henricus P. H. Scholten, Tette J. Dijkstra, Roeland Van Iperen
  • Patent number: 4931157
    Abstract: An ungelled reaction product of a polyepoxide and an active hydrogen-containing material containing at least two active hydrogens per molecule is disclosed. The active hydrogen-containing material being a hydroxyalkyl-substituted urethane in which the hydroxy group is in the beta position to the urethane group. The reaction product is useful as a precursor in making cationic resins for use in cationic electrodeposition.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: June 5, 1990
    Assignee: PPG Industries, Inc.
    Inventors: Joseph T. Valko, Joseph E. Plasynski, Robert D. Miller
  • Patent number: 4916019
    Abstract: A cationic electrodeposition coating composition for forming a multilayer film, said composition comprising(A) an epoxy-type cationic electrodepositable resin which is an addition-reaction product formed between an epoxy resin and a basic amino compound, having a surface tension of 40 to 60 dynes/cm and being capable of forming a cathodically depositable aqueous bath by neutralization with an acid,(B) a non-ionic, non-selfcurable, film-forming resin having a surface tension of 25 to 45 dynes/cm, and(C) a blocked polyisocyanate compound as a curing agent,the weight ratio of resin (A) to resin (B) being from 60:40 to 98:2, and the surface tension of resin (A) being at least 5 dynes/cm higher than that of resin (B), and resin (A), resin (B) and the polyisocyanate compound (C) having substantially no ethylenically double bond.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: April 10, 1990
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Eisaku Nakatani, Akira Tominaga, Haruo Nagaoka, Yoichi Masubuchi, Masafumi Kume, Tadayoshi Hiraki
  • Patent number: 4879325
    Abstract: A paint composition for cation electrodeposition painting, used for painting automotive vehicle body etc. The paint composition comprises basic unsaturated modified epoxy ester expressed by the general formula: ##STR1## where R.sub.1 and R.sub.2 are functional groups at least one of which is .alpha., .beta.-ethylenic double bond containing groups and the remainder is an unsaturated fatty acid chain; R.sub.3 is a group expressed by the formula: ##STR2## and X and Y are functional groups whose total number is n+1 in which not less than one functional group is a group containing both a tertiary amine function and a urethane function, and the remainder are hydroxyl groups (--OH), n being an integer ranging from 1 to 20.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: November 7, 1989
    Assignees: Nissan Motor Co., Ltd., Shinto Paint Co., Ltd.
    Inventors: Hitoshi Kimura, Shigenori Kazama, Akitoshi Shirasaka, Kiyoshi Taki, Yukihiro Manabe
  • Patent number: 4871807
    Abstract: Water-dilutable paint binders for the formulation of ecological stoving paints containing only minor quantities of organic solvents are described. The binders are partial condensation products of (A) a polycondensation, polymerization, or polyaddition resin as the film-forming polycarboxy compound (PC-component), and (B) an epoxy resin amine adduct (PH-component) carrying hydroxy groups and being water-insoluble under normal processing conditions. The products afford improved corrosion resistance and are particularly suited for the formulation of primers, intercoats (primer surfacers), and single coat paints.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: October 3, 1989
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Werner Staritzbichler, Gert Dworak, Wolfgang Daimer
  • Patent number: 4870119
    Abstract: Water-soluble cross-linked polyamides are produced by reacting (B) a cross-linking agent with (A) the product of reacting (A.sub.1) a dicarboxylic acid and (A.sub.2) a polyamine, provided that at least one of (A.sub.1) (A.sub.2) and (B) contains an aromatic moiety or that the product of reacting (B) with (A) is further reacted with a compound containing an aromatic moiety. The products are useful as binders for aqueous printing inks.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: September 26, 1989
    Assignee: Sandoz Ltd.
    Inventors: Benjamin K. C. Yee, William L. Younan
  • Patent number: 4857567
    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: July 24, 1987
    Date of Patent: August 15, 1989
    Assignee: BASF Corporation, Inmont Division
    Inventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
  • Patent number: 4851486
    Abstract: Self-crosslinking cationic paint binders based on ureide-modified epoxy resins; the preparation of these binders and their use, particularly in electrodeposition paints, is described. The modification is effected with carboxylic compounds carrying ureide groups, blocked isocyanate groups and, optionally, tertiary amino groups. The carboxylic compounds are obtained through reaction of dicarboxylic acid anhydrides or compounds carrying dicarboxylic acid anhydrides with a substituted urea or a substituted biuret. The products show excellent resistance and adhesion characteristics.
    Type: Grant
    Filed: May 18, 1988
    Date of Patent: July 25, 1989
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 4829100
    Abstract: Methods of continuously forming and suspending consolidatable resin composition coated particulate material in a gelled aqueous carrier liquid and transporting the coated particulate material by way of the gelled aqueous carrier liquid to a zone in which the sand is consolidated. In accordance with the methods, substantially continuous streams of a gelled aqueous carrier liquid, uncoated particulate material, a resin composition which will subsequently harden and a surface active agent are admixed whereby the particulate material is continuously coated with the resin composition and suspended in the gelled aqueous carrier liquid.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: May 9, 1989
    Assignee: Halliburton Company
    Inventors: Joseph R. Murphey, Kenneth D. Totty
  • Patent number: 4824927
    Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: April 25, 1989
    Assignee: BASF Lacke & Farben AKT
    Inventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
  • Patent number: 4818356
    Abstract: The invention relates to a process for coating an electrically conductive substrate, the said substrate being immersed in an aqueous bath based on a cationic synthetic resin binder which is at least in part neutralized with acids and contains amino and/or hydroxyl groups. The said bath contains a mixture of crosslinking agents as well as pigments, fillers, corrosion inhibitors, paint auxiliary substances, and, if appropriate, catalysts, as well as organic solvents in an amount of up to 15% by weight based on the total weight of the coating, the said substrate being cathodically connected. By the action of direct current, a film is deposited on the substrate, after which the said substrate is removed from the bath and the film is cured by stoving, the mixture of crosslinking agents comprising at least two crosslinking agents of different reactivities based on activated esters and/or polyisocyanates blocked by different blocking agents.
    Type: Grant
    Filed: September 25, 1986
    Date of Patent: April 4, 1989
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Michael Geist, Gunther Ott, Georg Schon, Arnold Dobbelstein, Wolfgang Batzill
  • Patent number: 4789696
    Abstract: Cationic paint binders, particularly binders of the type used in cathodic electrodeposition coatings which crosslink through transesterification, transamidation, transurethanization, or through the reaction of chain end double bonds catalyzed with a condensation product of a dialkyltinoxide and a compound carrying at least one hydroxyl group are described. The hydroxyl compounds are the aliphatic alcohols, phenols, alkanolamines, or the reaction products of primary amines with monoepoxy compounds. The catalysts of the invention provide very good stability and good compatibility in aqueous cationic paint materials.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: December 6, 1988
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Johann Gmoser
  • Patent number: 4771087
    Abstract: The invention discloses crosslinking components for hydroxy and/or primary and/or secondary amine groups containing cationic resins which can be used as binders for stoving paints, particularly for cathodically depositable electrodeposition paints. The crosslinking components are obtained through partial transesterification of transamidation of oligomeric KNOEVENAGEL-reaction products of C-H-active esters and carbonyl compounds with polyols or amines. The products can also be obtained through partial transesterification or transamidation of the C-H-active esters and subsequent KNOEVENAGEL-reaction.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: September 13, 1988
    Assignee: Vianova Kunstharz A.G.
    Inventors: Rudolf Schipfer, Gerhard Schmolzer, Wolfgang Daimer
  • Patent number: 4762903
    Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes, the said binders containing latent primary amino groups. In order to prepare the binders, an epoxy resin is reacted with a polyamine, which in addition to a sterically hindered primary amino group also contains at least one primary amino group blocked by reaction with a ketone or aldehyde, and, if appropriate, further primary or secondary amines.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: August 9, 1988
    Assignee: BASF Lacke & Farben AG
    Inventors: Michael Geist, Gunther Ott, Georg Schon
  • Patent number: 4761337
    Abstract: Cathodic electrodepositable resin compositions and aqueous electrodeposition coating baths comprising these resins are disclosed. The resin compositions comprise a cationic amine epoxy resin adducts and a cationic polyurethane resin adduct dispersion. The resin compositions when combined with a cross-linking agent and cathodically electrodeposited produce films which cure to durable, flexible, smooth corrosion-resistant, impact and chip-resistant films.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: August 2, 1988
    Assignee: BASF Corporation
    Inventors: Matthew Guagliardo, Tapan K. DebRoy, John Pucknat
  • Patent number: 4721742
    Abstract: Curable amide modified epoxy resins are prepared by polymerizing (I) the reaction product of (A) the reaction product of (1) an epoxy resin having an average of more than one 1,2-epoxy group per molecule and an average of from about 0 to about 30 aliphatic hydroxyl groups per molecule such as a diglycidyl ether of bisphenol A and (2) (a) a material having only one primary amine group per molecule such as monoethanolamine and (b) a material having only one secondary amine group per molecule such as diethanolamine wherein (a) and (b) are added sequentially with (a) being added first, or as a mixture with (B) an anhydride of an unsaturated dicarboxylic acid such as maleic anhydride with (II) a polymerizable ethylenically unsaturated monomer or mixture of monomers such as styrene and methacrylic acid. The resultant resin can be employed as is in the preparation of organic solvent borne coatings or it can be neutralized with a base so as to improve its stability in the preparation of aqueous coatings.
    Type: Grant
    Filed: November 7, 1986
    Date of Patent: January 26, 1988
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Willie L. Myles
  • Patent number: 4704437
    Abstract: Process for the preparation of soluble synthetic resins which are free from monomeric amines and have NH bonds by reaction of (A) compounds which carry epoxide groups with (B) polyamines, in which the reaction is carried out in a homogeneous phase system in the absence or presence of resin solvents, the polyamine (B) being employed in excess and the resulting reaction product being freed from the unreacted polyamine portions by circulatory distillation in the presence of a resin solvent with the addition of water and supply of heat. The synthetic resins thus prepared are employed as self-crosslinking binders and in combination with crosslinking agents or in modified form for coatings or impregnations.
    Type: Grant
    Filed: October 28, 1986
    Date of Patent: November 3, 1987
    Assignee: Hoechst AG
    Inventor: Hans-Joachim Kiessling
  • Patent number: 4699937
    Abstract: A synthetic resin carrying basic nitrogen groups, its preparation, coating materials prepared from this resin, and a process for cathodic electrocoating.This synthetic resin is obtained by reacting(A) an epoxy resin which(B) a diketimine of a diprimary amineand, if required,(C) with a secondary amine, which may additionally contain a tertiary amino group, with a ketimine of a primary monoamine and/or with a ketimine of a primary/tertiary diamine,a diketimine obtained from(B.sub.1) a ketone and(B.sub.2) a branched aliphatic diprimary diamine of 5 to 9 carbon atoms and/or(B.sub.3) one or more diaminodiamides which are obtained by condensation of 2 moles of diamine (B.sub.2) and 1 mole of a dicarboxylic acidbeing employed as component (B).After protonation with an acid, this synthetic resin is useful as a binder for cathodic electrocoating.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: October 13, 1987
    Assignee: BASF Farben+Fasern Aktiengesellschaft
    Inventors: Werner Loch, Eberhard Schupp, Rolf Osterloh, Klaas Ahlers
  • Patent number: 4600485
    Abstract: Aqueous electrodip lacquer coating compound capable of being deposited cathodically, containing, as synthetic resin binder,(A) 55 to 95% by weight of synthetic resin binder which can be rendered water soluble by protonation with acid and(B) 5 to 45% by weight of a cross-linking agent containing ester groups capable of transesterification and/or transamidation and having terminal ester groups which are substantially stable in a neutral aqueous medium but capable of reacting with synthetic resin binder (A) in an alkaline medium at temperatures above 140.degree. C., component (A) containing in its molecule at least one molecule-enlarging diamine of the formula ##STR1## wherein the symbol Y stands for H or C.sub.m H.sub.2m+1 (m=1 to 8) or an organic group used for defunctionalization, which is formed by the reaction of the primary amino group with monoepoxides, and the symbol X represents a molecular grouping having at least one amide and/or urea group.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: July 15, 1986
    Assignee: Herberts Gesellschaft mit beschraenkter Haftung
    Inventors: Hans-Peter Patzschke, Armin Goebel, Klausjorg Klein
  • Patent number: 4596844
    Abstract: The present invention relates to a water-dispersible self-hardenable resin composition, and particularly to a self-hardenable resin composition, which has a low-temperature hardenability and is adapted for the cationic electrodeposition painting wherein a material to be painted is used as a cathode.The present invention provides a self-hardenable resin composition consisting essentially of a Michael type addition reaction product consisting of 65-95% by weight (in solid base) of a polyamine resin having amino groups and/or imino groups and 35-5% by weight of an ethylenically unsaturated compound having an amine-imido group.
    Type: Grant
    Filed: May 20, 1985
    Date of Patent: June 24, 1986
    Assignee: Nippon Oil and Fats Company
    Inventors: Akira Ohsawa, Syuichi Manabe
  • Patent number: 4595717
    Abstract: Aqueous electrodip lacquer coating compound capable of being deposited cathodically, containing, as synthetic resin binder,(A) 55 to 95% by weight of synthetic resin binder which can be rendered water soluble by protonation with acid and(B) 5 to 45% by weight of a cross-linking agent containing ester groups capable of transesterification and/or transamidation and having terminal ester groups which are substantially stable in a neutral aqueous medium but capable of reacting with synthetic resin binder (A) in an alkaline medium at temperatures above 140.degree. C., component (A) containing in its molecule at least one molecule-enlarging diamine of the formula ##STR1## wherein the symbol Y stands for H or C.sub.m H.sub.2m+1 (m=1 to 8) or an organic group used for defunctionalization, which is formed by the reaction of the primary amino group with monoepoxides, and the symbol X represents a molecular grouping having at least one amide and/or urea group.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: June 17, 1986
    Assignee: Herberts Gesellschaft mit beschraenkter Haftung
    Inventors: Hans-Peter Patzschke, Armin Gobel, Klausjorg Klein
  • Patent number: 4576979
    Abstract: Heat-curable surface-coating agents useful not only for application as solvent-containing finishes and for powder coating but also, in their protonated form, for cathodic electrocoating contain, as a binder, a mixture of (A) a polyadduct, polycondensate or other polymer having an average molecular weight M.sub.n of from 500 to 10,000 and, per molecule, on average two or more OH and/or primary and/or secondary amino groups and (B) a reaction product of (a) one or more polyisocyanates, (b) one or more secondary monoamines and, if appropriate, (c) one or more polyalcohols having two or more hydroxyl groups.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: March 18, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Schupp, Werner Loch, Rolf Osterloh, Klaas Ahlers
  • Patent number: 4568710
    Abstract: The invention relates to cathodically electrodepositable coating compositions comprising an aqueous dispersion of self-crosslinkable resin. The self-crosslinkable resin is amine and epoxide functional and prepared by reacting epoxide resin with fatty amidopolyamine at about room temperature so as to form a partially crosslinked resin, wherein at least about 50 percent of the amine groups have been neutralized with a water soluble acid. The partially crosslinked resin can be deposited from the bath onto a metal substrate and cured at elevated temperatures to form a coating offering excellent corrosion protection and having excellent adhesion to the substrate.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: February 4, 1986
    Assignee: Ford Motor Company
    Inventors: Robert A. Swider, Martha E. Horsch
  • Patent number: 4568709
    Abstract: Cathodically depositable electrodeposition paint binders comprising the reaction product of an epoxy resin with at least two epoxy groups with amines carrying primary amino groups and, optionally, with a carboxylic acid compound to provide an epoxy resin-amino adduct which is then reacted with a phenol and formaldehyde. The binders have excellent corrosion resistance and crosslink to provide coating films at relatively low stoving temperatures without splitting off of substances harmful to the environment.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: February 4, 1986
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Johann Gmoser, Helmut Honig, Wolfgang Daimer
  • Patent number: 4565838
    Abstract: Cathodically depositable electrodeposition paint binders comprising a mixture of (A) 95-50% by weight of the reaction product of an epoxy resin with at least two epoxy groups with amines carrying primary amino groups and, optionally, with a carboxylic acid compound to provide an epoxy resin-amino adduct which is then reacted with a phenol and formaldehyde; and (B) 5-50% by weight of an addition component which is substantially water-insoluble under the conditions of electrodeposition and being compatible with Component A. The presence of Component B in the binder provides increased resistance to corrosion, improvements in the surface quality of the stoved films, and enhanced crosslinking of the binder.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: January 21, 1986
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Wolfgang Daimer
  • Patent number: 4565852
    Abstract: A crosslinkable composition of matter is provided, which comprises first and second chain extended diepoxide resins, one or both of which are prepared using an excess of diepoxide reactant and modified by reaction with hydroxy functional secondary amine. The first resin, diene functional aminoepoxy resin, and the second resin, blocked dieneophile functional aminoepoxy resin, are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene. The blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional blocked dieneophile chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional blocked dieneophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resins.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: January 21, 1986
    Assignee: Ford Motor Company
    Inventor: Saiyed B. A. Qaderi
  • Patent number: 4564648
    Abstract: Dispersion of an epoxy ester graft acrylic in water with a total of no more than 5% of organic volatiles and amines. These dispersions can be used in primer compositions for metal substrates having a minimum of organic solvent emissions and which can crosslink at temperatures from 110.degree.-200.degree. C., giving a good balance of hardness, flexibility, humidity, corrosion resistance and anti-chipping properties.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: January 14, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Jozef T. Huybrechts, Victor R. Vleminckx
  • Patent number: 4559393
    Abstract: A self-crosslinkable resin and composition of matter comprising same is provided, which resin comprises certain diene functional blocked dieneophile functional aminoepoxy resin, which resin is self-crosslinkable at elevated cure temperature. The diene functional blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant, mono-secondary amine functional blocked dieneophile and, optionally, monofunctional end-capping reactant such as mono-secondary amine functional diene and mono-secondary amine functional blocked dienophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resin. The crosslinkable composition of matter is useful in coating and other applications, especially solvent-based primer coating compositions and cathodic electrocoating compositions.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: December 17, 1985
    Assignee: Ford Motor Company
    Inventor: Joseph W. Holubka
  • Patent number: 4536558
    Abstract: This invention relates to water dispersible, cathodically electrodepositable resins which are prepared by reacting chain extended polyepoxides with secondary amines. The polyepoxides have been chain extended with polycarboxylic acids. The resin is dispersible in water with the aid of a water soluble acid to provide cationic groups in the resin. Preferred crosslinking agents for the resin comprises capped isocyanates which may be either incorporated in the resin or preferably co-deposited with the resin from the coating composition bath.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: August 20, 1985
    Assignee: Ford Motor Company
    Inventor: Panagiotis I. Kordomenos
  • Patent number: 4515911
    Abstract: The invention relates to cathodically electrodepositable coating compositions comprising an aqueous dispersion of self-crosslinkable resin. The self-crosslinkable resin is amine and epoxide functional and prepared by reacting epoxide resin with polyamine at about room temperature, wherein at least 50 percent of the amine groups have been neutralized with water soluble acid. The polyamine contains at least one primary amine group and at least one tertiary amine group. The partially crosslinked resin product can be deposited on a metal substrate and cured at elevated temperatures to form a coating offering excellent corrosion protection and having excellent adhesion to the substrate.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: May 7, 1985
    Assignee: Ford Motor Company
    Inventors: Robert A. Swider, Martha E. Horsch
  • Patent number: 4491611
    Abstract: Catalytically self-cross-linking resinous binders are prepared by (a) addition reaction of a primary amine to a beta-hydroxyalkyl ester of an alpha, beta-ethylenically unsaturated acid, and (b) reaction of this secondary amine adduct, optionally in combination with other amines, with an epoxy resin. Curing catalysts are transesterification-promoting metal compounds. Protonized binders can be used in a cathodic electrodeposition bath.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: January 1, 1985
    Assignee: Shell Oil Company
    Inventors: Adrianus J. M. Barnhoorn, Werner T. Raudenbusch
  • Patent number: 4489182
    Abstract: Coating compositions comprising a polymeric polyol with a polyester crosslinking agent having at least two gamma and/or delta-hydroxyester groups per molecule are disclosed. The compositions, when applied to a substrate and cured in the presence of a transesterification catalyst, give solvent-resistant coatings.
    Type: Grant
    Filed: July 29, 1981
    Date of Patent: December 18, 1984
    Assignee: PPG Industries, Inc.
    Inventor: Joseph T. Valko
  • Patent number: 4461857
    Abstract: Aqueous thermosetting coating compositions are disclosed characterized by reduced curing requirements and which produce coatings having superior cured properties. These coatings comprise water containing water miscible organic solvent and the compositions have dispersed therein, based on total resin solids, from 25% to 85% of carboxy-functional organic solvent-soluble copolymer salt with a volatile amine in which the copolymer contains hydroxy groups providing an hydroxyl value in the range of 30 to 300, from 5% to 40% of a water soluble or water dispersible aminoplast or phenoplast curing agent, and from 2% to 35%, of a water dispersible epoxy phosphate ester polymer which is an oxirane-function-free, salt reaction product of (1) a monoester reaction product containing residual epoxy functionality, of (a) a resinous polyepoxide having at least about 1.4 oxirane groups per molecule, and (b) less than 0.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: July 24, 1984
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah