With Organic Nitrogen Or Organic Sulfur Reactant Patents (Class 523/404)
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Patent number: 6303672Abstract: A self-dispersing curable epoxy composition is prepared upon contacting an epoxy resin with a polyoxyalkylenemonoamine having a molecular weight of from about 3,000 to about 15,000 in a ratio of about 0.001 to 0.060 reactive equivalents of polyoxyalkylenemonoamine to about 1.0 reactive equivalents of epoxy resin. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: June 7, 1995Date of Patent: October 16, 2001Assignee: Henkel CorporationInventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 6300395Abstract: A hydrophilic coating having excellent hydrophilicity, which can prevent offensive odor generation, and which has a good antibacterial performance and formability, is formed on an aluminum-containing metal material by coating an aqueous hydrophilization treating liquid containing (A) a glycidyl group-containing, water-soluble organic compound; (B) a water-soluble polymeric or polymerizable compound having a tert-amino group and at least one hydrophilic functional group selected from sulfonic, phosphonic, carboxyl, polyalkyleneglycol, hydroxyl and amide groups; and (C) an antibacterial agent not decomposing at 100° C. or lower, on an aluminum-containing metal material; and heat-drying the coated liquid.Type: GrantFiled: December 5, 1995Date of Patent: October 9, 2001Assignee: Nikon Parkerizing, Co., Ltd.Inventors: Ryosuke Sako, Tomohiro Ohsako, Tatsuo Hibino
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Patent number: 6294596Abstract: A self-dispersing curable epoxy composition is prepared upon contacting an epoxy resin with a polyoxyalkyleneamine having a molecular weight of from about 3,000 to about 15,000 in a ratio of about 0.001 to 0.060 reactive equivalents of polyoxyalkyleneamine to about 1.0 reactive equivalents of epoxy resin. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: September 15, 1995Date of Patent: September 25, 2001Assignee: Henkel CorporationInventors: John G. Papalos, Shailesh Shah, Reuben H. Grinstein, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 6291554Abstract: Disclosed is an anionic, self-emulsified aqueous epoxy resin dispersion prepared through the semi-esterification reaction between a dicarboxylic acid anhydride and the secondary hydroxy group of an epoxy resin, followed by neutralization of the carboxylic acid thus introduced into the epoxy resin with a tertiary amine and then adding only water, without the need of any emulsifier, to the resulting hydrophilic amine salt of the carboxylic acid. The stable aqueous epoxy resin contains both carboxyl and epoxy groups which are reactive functional groups. Also disclosed is a “single-pack” curable aqueous epoxy resin system “cross-linkable” at normal temperature prepared by adding a compound containing polyaziridine as a cross-linking agent into the aqueous epoxy resin dispersion. Upon drying, the liberated carboxyl group in the aqueous epoxy resin reacts with the polyaziridine to form an amino ester via a ring opening reaction.Type: GrantFiled: October 29, 1999Date of Patent: September 18, 2001Assignee: Chinese Petroleum Corp.Inventors: Tsorng-Wen Chen, Jen-Taut Yeh, Kan-Nan Chen, Yun-Shan Lin
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Patent number: 6277928Abstract: A water-dispersible curing agent for epoxy resins is prepared by the reaction of (a) an epoxy-functional compound obtained from the reaction of at least one epoxy resin and an amidoamine derived from the reaction of an acid-terminated polyalkylene glycol and a diamine in an active amine hydrogen:epoxy groups ratio of from 1:15 to 1:350, (b) at least one polyamine in an active amine hydrogen:epoxy groups ratio of from 2:1 to 30:1 which yields an amine-terminated product having an amine equivalent weight of at least 50, and, optionally, (c) a monoepoxy in a remaining active amine hydrogen:epoxy groups ratio of from 5:1 to 20:1.Type: GrantFiled: June 10, 1998Date of Patent: August 21, 2001Inventors: Charles J. Stark, by Ann E. Stark, adminstrator, Gayle Edward Back, Jimmy D. Elmore, Kalyan Ghosh, Pen-Chung Wang, Kailash Dangayach
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Patent number: 6274649Abstract: The present invention relates to an aqueous binder dispersion for cathodic electrodeposition coatings obtained A) by reacting I. a precursor prepared at temperatures of from 120 to 180° C. from a) a diepoxide compound or a mixture of diepoxide compounds and b) an aromatic or aliphatic compound hydroxyl, carboxyl, phenol and/or thiol groups, or a mixture of such compounds with reaction of the phenolic hydroxyl groups with epoxide groups, II. with at least one organic amine or a mixture of organic amines at a temperature between 60 and about 130° C. to give an epoxide/amine adduct; B) subsequently or simultaneously reacting at least one secondary hydroxyl group of the precursor with an unreacted epoxide group of the epoxide/amine adduct prepared in step A) at a temperatures of from about 110 to about 150° C.; C) adding a crosslinking agent at a temperature of less than about 150° C.Type: GrantFiled: September 2, 1999Date of Patent: August 14, 2001Assignee: BASF Coatings AGInventors: Günther Ott, Hardy Reuter, Walter Jouck, Thierry Herning, Susanne Piontek, Ulrich Heimann, Karl-Heinz Grosse-Brinkhaus
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Patent number: 6268409Abstract: The invention relates to a binder (A) in aqueous dispersion which is obtainable by neutralization of the tertiary amino groups of an amino-epoxy resin a1) with acid and reaction of the resulting product with a polyepoxide a2) to form quaternary ammonium groups and conversion into an aqueous dispersion with water. The invention furthermore relates to a process for the preparation of binders (A) in aqueous dispersion and their use in cathodic electrodeposition lacquers.Type: GrantFiled: September 17, 1999Date of Patent: July 31, 2001Assignee: Herberts GmbH & Co. KGInventors: Klausjörg Klein, Helmut Hönig
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Publication number: 20010008692Abstract: A cationic electrodeposition coating composition is provided which contains blocked isocyanate curing agent which is blocked with a substance not recognized as a HAPs (hazardous atmospheric pollutant).Type: ApplicationFiled: January 5, 2001Publication date: July 19, 2001Inventors: Shinsuke Shirakawa, Keisuke Tsutsui, Mitsuo Yamada
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Patent number: 6262146Abstract: An aliphatic hydrocarbon group-containing resin composition for cationic electrocoating, which comprises a resin having a skeleton of epoxy resin and has a number average molecular weight of 500 to 20,000, and which contains, per 100 grams of the nonvolatile matter in said resin composition, (a) 5 to 400 millimoles of sulfonium group, (b) 80 to 355 millimoles of at least one aliphatic hydrocarbon group containing 8 to 24 carbon atoms and optionally containing unsaturated double bond within its chain, and (c) 10 to 315 millimoles of at least one member selected from among propargyl group and a terminal unsaturated double bond-containing organic group containing 3 to 7 carbon atoms; the total content of said (a), said (b) and said (c) being not more than 500 millimoles per 100 grams of the nonvolatile matter in said resin composition.Type: GrantFiled: July 22, 1999Date of Patent: July 17, 2001Assignee: Nippon Paint Co., Ltd.Inventors: Hiroyuki Sakamoto, Saori Yoshimatsu, Ichiro Kawakami, Koji Izumiya, Toshitaka Kawanami, Takao Saito
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Patent number: 6245835Abstract: An emulsified reactive epoxy polymer composition which is readily dispersed in water particularly suited for use in a coating composition which may be cured at ambient temperatures. The emulsified composition incorporates a hydrophilic polyoxyalkylene segment.Type: GrantFiled: November 20, 1998Date of Patent: June 12, 2001Assignee: The Dow Chemical CompanyInventors: Dieter H. Klein, Hans Juergen Wessely, Karin C. Joerg
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Patent number: 6225376Abstract: An emulsified reactive epoxy polymer composition which is readily dispersed in water and is particularly suited for use in a coating composition which may be cured at ambient temperatures. The emulsifiable epoxy composition incorporates a hydrophilic polyoxyalkylene segment.Type: GrantFiled: November 20, 1998Date of Patent: May 1, 2001Assignee: The Dow Chemical CompanyInventors: Dieter H. Klein, Karin C. Joerg
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Patent number: 6221980Abstract: A latent curing agent is disclosed for epoxy resin, comprising a reaction product obtainable by allowing (A) an epoxy compound having more than one epoxy groups on the average in the molecule and (B) a compound having in the molecule both a tertiary amino group and at least one functional group selected from the group consisting of OH group, SH group, NH group, NH2 group, COOH group and CONHNH2 group, to react on each other in the presence of 0.05-5.0 equivalents of water per 1 equivalent of the epoxy group of Compound (A); and a curable epoxy resin composition comprising such curing agent and an epoxy compound having more than one epoxy group on the average in the molecule.Type: GrantFiled: April 16, 1999Date of Patent: April 24, 2001Assignee: Ajinomoto Co., Inc.Inventors: Junji Ohashi, Tetsuo Hinoma
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Patent number: 6221934Abstract: Stable aqueous emulsions of epoxy resins are provided using an epoxy-functional surfactant prepared by reacting an amidoamine having the formula: wherein R1 is an alkyl, aryl, or arylalkyl group or mixtures thereof having 1 to 15 carbon atoms, R2 is aliphatic, cycloaliphatic, or aromatic group having 2 to 18 carbon atoms optionally containing non-reactive oxygen or at most all average of 4 secondary and/or tertiary nitrogen atoms per structure in the backbone, X and Y are independently a hydrogen, methyl or ethyl group with the provision that if X is methyl or ethyl, Y is hydrogen or if Y is methyl or ethyl, X is hydrogen, and n+m+o is a real number from 40 to 400, and n+o is a real number in an amount effective to provide resin emulsification, and the ratio of (I) to (II) by weight.Type: GrantFiled: July 17, 1998Date of Patent: April 24, 2001Assignee: Shell Oil CompanyInventors: Charles J. Stark, Jimmy D. Elmore, Gayle Edward Back, Pen-Chung Wang, Ernest Charles Galgoci, Jr.
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Patent number: 6207731Abstract: A cathodic electrocoating composition comprises an aqueous carrier, a film forming binder, comprising an epoxy-amine adduct and a blocked polyisocyanate crosslinking agent, dispersed in the carrier, and a novel additive comprising the reaction product of (1) a polyoxy alkylene di or monoamine; (2) a glycidoxy alkyl alkoxy silane; and (3) a glycidyl compound selected from the group consisting of a glycidyl ester of a carboxylic acid and an alkyl glycidyl ether, which reaction product is hydrolyzed in the presence of acid and water to convert alkoxysilane moieties to silanol moieties. The electrocoat composition produces coatings having a smoother appearance with better edge coverage and fewer craters.Type: GrantFiled: September 23, 1999Date of Patent: March 27, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: Allisa Gam
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Patent number: 6187856Abstract: An antistatic composition containing a crosslinked thermosetting resin formed by reacting, in the presence of a water-soluble solvent, (a) a polyaminoamide having unreacted primary and secondary amine groups and (b) a polychlorohydrin derivative.Type: GrantFiled: March 18, 1998Date of Patent: February 13, 2001Assignee: Henkel CorporationInventors: Michael J. Incorvia, Stephen A. Fischer
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Patent number: 6183616Abstract: A method of stabilization of electrolyte bath in electrocoating by immersing a substrate in the bath filled with a cationic electrocoating composition containing a basic resin and an amine compound and carrying out electrocoating; wherein said basic resin in said bath contains, per 100 grams of the resin solids, 10 to 300 millimoles of sulfonium group and 50 to 2,000 millimoles of carbon—carbon unsaturated bond, and said amine compound is contained in an amount of 1 to 50 millimoles per 100 grams of the basic resin solids in the bath, said amount being not less than 5 mole percent relative to the sulfonium group content in said basic resin, so that the sulfonium group remaining in the coat amount to not more than 50% relative to the sulfonium group contained in the electrocoating composition in said bath.Type: GrantFiled: July 22, 1999Date of Patent: February 6, 2001Assignee: Nippon Paint Co., Ltd.Inventors: Hiroyuki Sakamoto, Takayuki Kokubun, Ichiro Kawakami, Toshitaka Kawanami, Hitoshi Hori, Takao Saito
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Patent number: 6160040Abstract: There is provided a surfactant composition, a stable, self emulsifiable water borne curing agent composition, and methods for the manufacture of each, and two component water borne curable epoxy resin compositions. The surfactant composition comprises the reaction product of an a) a phenolic acid substituted with at least one carboxyl group and at least one hydrocarbyl group having at least 1 carbon atom; b) a polyepoxide compound; c) a polyamine compound having at least two primary amine groups; d) a reactive surfactant; and optionally e) a monoglycidyl, monocarboxylic acid, or monoisocyanate capping agent; wherein the reactive surfactant comprises an epoxide, a carboxylic acid or anhydrides thereof, or an isocyanate functional moeity, and a hydrophilic moiety comprising a polyoxyalkylene monool or polyol residue.Type: GrantFiled: December 31, 1997Date of Patent: December 12, 2000Assignee: Shell Oil CompanyInventor: Kalyan Ghosh
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Patent number: 6156823Abstract: An improved aqueous cathodic electrocoating composition having a binder of an epoxy-amine adduct and a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of a catalytic amount of bismuth trioxide dispersed in the electrocoating composition.Type: GrantFiled: December 4, 1998Date of Patent: December 5, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Robert John Sikora
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Patent number: 6143809Abstract: A process to provide an aqueous dispersion is provided comprising the steps of:a) emulsifying a mixture comprisingi) water,ii) at least one epoxy resin having a functionality of greater than 0.8 epoxide group per molecule,iii) from 0.1 to 20 weight percent, based on the epoxy resin, of at least one polyoxyalkylene surfactant, andiv) optionally an acetone-free solvent solution to produce a resin-surfactant emulsion; andb) adding a solvent mixture to said resin-surfactant emulsion, said solvent mixture comprising i) acetone and ii) a non-volatile hydrophobic liquid resin or resin modifier to produce the aqueous dispersion.Type: GrantFiled: July 17, 1998Date of Patent: November 7, 2000Assignee: Shell Oil CompanyInventors: Jimmy D. Elmore, Vincent James Maksymowski, Richard William Henning, Jr., Ernest Charles Galgoci, Jr.
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Patent number: 6136894Abstract: An aqueous epoxy resin system suitable for coatings comprises (a) water, (b) at least one epoxy resin and (c) a curing agent prepared by (i) reacting at least one polyamine having at least 3 active amine hydrogen atoms per molecule and at least one epoxy resin in an epoxy equivalent to to polyamine mole ratio of from 0.9:1 to 1:10 to obtain an amine-terminated intermediate; (ii) reacting the amine-terminated intermediate with from 0.5 to 25 weight percent, based on the amine-terminated intermediate, of an acid-terminated polyalkylene glycol to yield an amine-terminated curing agent. The amine-terminated intermediate can be capped with a monoepoxide in an amine hydrogen to epoxy groups ratio of from about 1.5:1 to 30:1 prior to reaction with the acid-terminated polyalkylene glycol, or the amine-terminated curing agent following step (ii) can be capped with a monoepoxide in an amine hydrogen atoms to epoxy groups ratio of from about 2:1 to 30:1.Type: GrantFiled: November 19, 1999Date of Patent: October 24, 2000Assignee: Shell Oil CompanyInventors: Charles J. Stark, deceased, Gayle Edward Back, Jimmy D. Elmore, Kalyan Ghosh, Pen-Chung Wang, Kailash Dangayach
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Patent number: 6127459Abstract: A water-compatible curing agent for epoxy resins is prepared by (a) reacting at least one polyamine having at least 3 active amine hydrogen atoms per molecule and at least one epoxy resin in an epoxy equivalent to polyamine mole ratio of from 0.9:1 to 1:10 to obtain an amine-terminated intermediate; (b) reacting the amine-terminated intermediate with from 0.5 to 25 weight percent, based on the amine-terminated intermediate, of an acid-terminated polyalkylene glycol to yield an amine-terminated curing agent. The amine-terminated intermediate can be capped with a monoepoxide in an amine hydrogen atoms to epoxy groups ratio of from about 1.5:1 to 30:1 prior to reaction with the acid-terminated polyalkylene glycol, or the amine-terminated curing agent produced following step (b) can be capped with a monoepoxide.Type: GrantFiled: June 10, 1998Date of Patent: October 3, 2000Assignee: Shell Oil CompanyInventors: Charles J. Stark, deceased, Gayle Edward Back, Jimmy D. Elmore, Kalyan Ghosh, Pen-Chung Wang, Kailash Dangayach
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Patent number: 6124380Abstract: The invention comprises a curable composition comprising: (i) a blocked reactive component wherein the blocked reactive component is a blocked isocyanate or a blocked isothiocyanate; (ii) a functional compound reactive with the blocked reactive component, the functional compound containing reactive hydrogen; (iii) a catalyst for promoting the reaction of the reactive component with the blocked functional compound, wherein said catalyst is based on the reaction product of manganese, cobalt, nickel, copper, zinc, germanium, antimony, or bismuth, or the oxides thereof with a mercaptan, or an organic acid, wherein said organic acid is hexanoic, oxalic, adipic, lactic, tartaric, salicylic, thioglycolic, succinic, or mercapto succinic acid, or the reaction product of copper or germanium, or the oxides thereof with a lower aliphatic acid.Type: GrantFiled: March 12, 1999Date of Patent: September 26, 2000Assignee: Elf Atochem North America, Inc.Inventors: Emily C. Bossert, Kevin Cannon, William D. Honnick, Wayne Ranbom
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Patent number: 6096806Abstract: Epoxy resins, particularly those based on bisphenol A, can constitute the principal film forming polymer component of a storage stable autodepositable composition wherein the particle size distribution of all the film forming polymers in the composition satisfies certain criteria of size distribution, and an accelerator component which is an acid, oxidizing agent or complexing agent is present in amount sufficient to provide an oxidation-reduction potential at least 100 mV more oxidizing than a standard hydrogen electrode. Such dispersions can conveniently be prepared using a two stage process in which a solution of the film forming polymers is emulsified into water to form a preliminary dispersion and this preliminary dispersion is subjected to at least one particle size refinement stage in which the preliminary dispersion is forced through a narrow aperture.Type: GrantFiled: February 17, 1998Date of Patent: August 1, 2000Assignee: Henkel CorporationInventors: Brian L. Mueller, Elizabeth J. Siebert
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Patent number: 6087444Abstract: A water reducible polyurethane resin for use in coating compositions is provided with humidity resistance at relatively low cost by employing a urethane prepolymer which is the reaction product of (i) a polyisocyanate, (ii) a polyhydroxy compound which is the reaction product of an organic acid and an epoxy compound, at least one of which includes a hydrocarbon group of at least six carbon atoms, and (iii) a monomer having an anionic group and functionality reactive with isocyanate. Preferred embodiments employ C.sub.36 dimer diacid and the propylene oxide ester of neodecanoic acid to make the polyhydroxy compound.Type: GrantFiled: September 20, 1996Date of Patent: July 11, 2000Assignee: PPG Industries Ohio, Inc.Inventors: Shanti Swarup, Anbazhagan Natesh, Gina M. Terrago, Cathy A. Taylor
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Patent number: 6071565Abstract: A water-borne epoxy resin coating composition comprised of: (a) particles of an epoxy resin having a neutral or positive surface charge dispersed in (b) water, an amount of (c) surfactant sufficient to disperse the epoxy resin in the water, the surfactant being a nonionic surfactant, amphoteric surfactant or mixture thereof and (d) a latent curing agent, may be applied to a metal substrate absent a primer coating and, subsequently, heated to form a cured coating on the substrate. The latent curing agent is (i) at least partially dissolved in the water, (ii) essentially insoluble with the epoxy resin and (iii) present in a sufficient amount to cure the epoxy resin. An example of a suitable latent curing agent is dicyandiamide. The cured coating displays excellent adherence, wear resistance and resistance to solvents such as acetone, a 1N HCl solution and a 1N KOH solution.Type: GrantFiled: April 20, 1998Date of Patent: June 6, 2000Assignee: The Dow Chemical CompanyInventor: Yi-Hung Chiao
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Patent number: 6063839Abstract: Disclosed are epoxy resin compositions for fiber-reinforced composite materials, comprising an epoxy resin containing 70 parts by weight or more, per 100 parts by weight of the epoxy resin, of a bi-functional epoxy resin, fine particles comprising a rubber phase and substantially insoluble in epoxy resins and a curing agent. Also disclosed are prepregs and fiber-reinforced composite materials comprising the composition.Type: GrantFiled: May 9, 1996Date of Patent: May 16, 2000Assignee: Toray Industries, Inc.Inventors: Hiroki Oosedo, Shunsaku Noda
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Patent number: 6063893Abstract: A curing agent having less odor and providing a cured resin which is excellent in appearance, mechanical properties, water resistance and chemical resistance, and a one-component type humidity-curing resin composition having excellent storage stability and providing a cured matter which is excellent in appearance and physical properties. Specifically, provided are polyaminoamide or ketimine obtained by dehydration of 2,5- and/or 2,6-bis(aminomethyl)-bicyclo[2.2.1]heptane with carboxylic acids or ketones, a curing agent for epoxy resins using the same and a one-component type humidity-curing epoxy resin or urethane prepolymer composition containing the curing agent.Type: GrantFiled: May 26, 1998Date of Patent: May 16, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Minato Karasawa, Takeya Abe, Takuji Shimizu, Takeshi Iwaki
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Patent number: 6045857Abstract: Unsaturated hydrophobic resins modified with labile hydrophillic groups exhibit reversible solubility in water. Beta-dialkyl amino carboxylate derivatives of novolak resins are useful to make baking enamels and resists.Type: GrantFiled: June 19, 1997Date of Patent: April 4, 2000Assignee: MacDermid Acumen, Inc.Inventor: Goutam Gupta
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Patent number: 6046256Abstract: A water-based dispersion composition obtained by partially or wholly neutralizing a mixture of a modified epoxy resin (A) as an emulsifying resin and an aromatic epoxy resin (B) having a number average molecular weight of 1,000 to 30,000 as a resin to be emulsified, with ammonia and/or an amine, the modified epoxy resin (A) being a modified epoxy resin obtained by reacting an aromatic epoxy resin (a1) having an epoxy equivalent of 2,000 to 20,000 with an acrylic resin (a2) having an acid value of 50 to 450 and containing acrylic acid and/or methacrylic acid, the water-based dispersion composition is applied to an internal surface of a metal can particularly required to have high processability and corrosion resistance by coating it directly on a metal material or coating it on an undercoating, baking it and drying it.Type: GrantFiled: April 9, 1998Date of Patent: April 4, 2000Assignee: Toyo Ink Manufacturing Co., Ltd.Inventors: Tetsuhisa Nakamura, Teruo Shiono, Masami Yamada, Sanji Harada, Masahiro Ihara, Takeshi Tsuyama
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Patent number: 6037435Abstract: The present application to an underwater curable coating composition which is used for protecting or imparting an aesthetic appearance to various structures. An underwater curable coating composition consisting essentially of an epoxy resin component and its curing agent, wherein the epoxy resin component is a mixture comprising a liquid hydrophobic epoxy resin and a self-emulsifiable liquid epoxy resin. The curing agent is composed partly or solely of a ketimine.Type: GrantFiled: September 25, 1998Date of Patent: March 14, 2000Assignee: Dai Nippon Toryo Co., Ltd.Inventors: Toshiharu Hayashi, Toshimoto Tsuji
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Patent number: 5962571Abstract: Process for making organic solvent-free aqueous crosslinkable polymer composition comprising: a) preparing an aqueous solution of an acid-functional oligomer with Tg 10 to 125.degree. C. and having crosslinker functional groups; b) conducting an aqueous emulsion polymerization to make an aqueous emulsion of an olefinic hydrophobic polymer in the presence of the aqueous oligomer solution, the hydrophobic polymer having Tg at least 25.degree. C. below that of the oligomer and optionally crosslinker functional groups, and c) combining with a crosslinking agent reactable with the crosslinker groups of the oligomer and polymer, said composition having Koenig hardness of .gtoreq.40 sec and minimum film forming temperature (MFFT) .ltoreq.55.degree. C. Also the aqueous composition so formed and its use in various applications. The aqueous composition has excellent properties and in particular an advantageous balance of MFFT and Koenig hardness.Type: GrantFiled: November 1, 1996Date of Patent: October 5, 1999Assignee: Zeneca Resins B.V.Inventors: Gerardus Cornelis Overbeek, Yvonne Wilhelmina Smak, Alfred Jean Paul Buckmann
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Patent number: 5961802Abstract: A cationic resin having latent primary amine functionality is described. The latent amine functionality is obtained by reacting a cyclic anhydride with an amine compound having two primary amine groups and one secondary amine group. The cationic resin is combined with a curing agent having a plurality of cyclic carbonate groups in an electrocoat bath.Type: GrantFiled: September 30, 1997Date of Patent: October 5, 1999Assignee: BASF CorporationInventors: Timothy S. December, Paul J Harris
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Patent number: 5936011Abstract: Provided are a modified polyamine which comprises a reaction product between a polyamine and a chlorohydrin synthesized by the reaction of a polyoxyalkylene polyether with an epichlorohydrine and having a total chlorine content of 1,000 ppm or below, and an aqueous epoxy resin curing agent using the same.Type: GrantFiled: April 30, 1996Date of Patent: August 10, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shuta Kihara, Shinichi Yonehama, Kichiro Seki
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Patent number: 5936012Abstract: An electrodepositable composition that has: (A) an active hydrogen-containing cationic resin, electrodepositable on a cathode, having: (1) a polyepoxide; (2) an oxygen-substituted diamine compound having the following formula: ##STR1## where n is an integer from 2 to 4; and where R.sup.1 or R.sup.2 are the same or different and either one or both contain at least one oxygen and are alkyl, cycloalkyl, substituted alkyl, or substituted cycloalkyl having from 1 to 6 carbon atoms, or R.sup.1 and R.sup.2 are alkanol groups having from 2 to 6 carbon atoms, or R.sup.1, R.sup.2, and the N atom form a cyclic group which is substituted or unsubstituted such as morpholine and 1-(3-aminopropyl) imidazole; and (B) at least partially blocked isocyanate or polyisocyanate curing agent. The diamine compound of Formula I can be used alone or in conjunction with one or more secondary amines, nonhydroxy group containing amines and/or amines with ring structures.Type: GrantFiled: October 7, 1998Date of Patent: August 10, 1999Assignee: PPG Industries Ohio, Inc.Inventors: Marvin L. Kaufman, Patrick O'Neill, Richard F. Karabin, Gregory J. McCollum
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Patent number: 5935710Abstract: This invention relates to coating compositions including one or more resins having amino-reactive groups; one or more polyamine curing agents; and one or more aminourethanes. The aminourethanes can be reaction products of (i) oligomeric or polymeric compounds which contain at least one, preferably two or more terminal 2-oxo-1,3-dioxolane groups (cyclic carbonate groups), and (ii) amines containing at least one primary, preferably two or more primary and, if desired, also secondary and tertiary amino groups. The ratios of equivalents of C1):C2) typically is from 1:1 to 1:10, preferably from 1:1.05 to 1:5 and particularly preferably from 1:1.1 to 1:2, and the end product preferably contains one or more free primary amino groups. The composition further may contain, if desired, pigments, fillers, one or more organic solvents, water and conventional additives.Type: GrantFiled: November 17, 1997Date of Patent: August 10, 1999Assignee: Vianova Resins GmbHInventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
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Patent number: 5925694Abstract: Aqueous, low-solvent coating compositions comprising a base resin dispersion comprising of an epoxy resin, prepared by condensation of one or more epoxide compounds having at least two epoxide groups per molecule and an aromatic polyol; a dispersant comprising a condensation product of an aliphatic polyol having a weight-average molar mass (M.sub.w) of from 200 to 20,000 g/mol and an epoxide compound having at least two epoxide groups per molecule, and low molar mass, liquid, epoxy-functional compounds as diluents, and also water; an aqueous curing agent for the modified epoxy resin (I), which is suitable for curing at room temperature or at elevated temperatures (forced drying), components (I) and (II) being employed in mass fractions such that the ratio of the number of reactive epoxide groups in (I) to the number of amine hydrogen atoms in (II) is between 1:0.75 and 1:2. The coating compositions exhibit an extended pot life. They can be used to produce coatings and in water-soluble adhesives.Type: GrantFiled: September 25, 1996Date of Patent: July 20, 1999Assignee: Vianova Resins GmbHInventors: Bernhard Stengel-Rutkowski, Claus Godau, Armin Pfeil
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Patent number: 5925719Abstract: A substantially ester-free, acid-functional thiol-functional resin is prepared via the reaction of an epoxy compound with a thiolacetic acid in the presence of an amine catalyst and heat to form a thioacetate derivative which is hydrolyzed to yield an ester-free, .beta.-hydroxy thiol-functional resin. The .beta.-hydroxy thiol-functional resin can then be reacted with a material capable of insert a group conferring aqueous-base developability such as a cyclic anhydride.Type: GrantFiled: June 19, 1997Date of Patent: July 20, 1999Assignee: MacDermid, IncorporatedInventors: John S. Hallock, Donald E. Herr
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Patent number: 5910369Abstract: A system for protecting surfaces and facilitating the removal of unwanted substances therefrom is disclosed, the system including a polymeric coating having a low volatile organics content (VOC) which is safe for the environment, and a cleaner for application to the coating to remove material from the coating, such as graffiti. The coating may be either a water-based epoxy comprising a bisphenol A resin and polyamide resin, or an aliphatic urethane comprising a polymer having reactive sites which react with a isocyanate and an aliphatic isocyanate. The cleaner is suitable for removing all manner of epoxy and urethane based spray paints, indelible inks, industrial chemicals, and the like. The cleaner comprises N-methyl pyrrolidone in a concentration of fifty percent by weight or greater and a surfactant.Type: GrantFiled: June 7, 1995Date of Patent: June 8, 1999Assignee: American Polymer, Inc.Inventors: Michael N. Macris, David Dobney
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Patent number: 5908902Abstract: A selif-emulsifying epoxy resin (A), prepared from proportions by mass of(A-1) from 50 to 95% of one or more epoxide compounds having at least two epoxide groups per molecule and an epoxide group content of from 300 to 11,200 mmol/kg;(A-2) from 5 to 50% of an aromatic polyol;(A-3) from 0 to 25% of modifying compounds having at least two epoxide-reactive groups;(A-4) from 5 to 25% of an emulsifying product of the condensation of(A-4-a) an aliphatic polyol having a weight-average molar mass M.sub.W of from 200 to 20,000 g/mol and(A-4-b) an epoxide compound having at least two epoxide groups per molecule and an epoxide group content of from 500 to 10,000 mmol/kg,whereby the ratio of the number of OH groups to the number of EP groups is from 1:2 to 1:10 and the epoxide group content of these condensation products (A-4) is between 100 and 6700 mmol/kg.Type: GrantFiled: June 7, 1996Date of Patent: June 1, 1999Assignee: Hoechst AktiengesellschaftInventors: Armin Pfeil, Dieter Dreischhoff, Claus Godau
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Patent number: 5906864Abstract: Aqueous coating composition, containingI) one or more amine hardeners,II) one or more water-dilutable epoxy resins,III) one or more pigments and/or fillers andIV) water and optionally one or more solvents and/or conventional lacquer additives,wherein the composition of the coating composition is selected in such a way that a hardened free film formed from the coating composition with a coat thickness between 30 and 80 .mu.m has a storage modulus E' of 10.sup.8 Pa to 5.times.10.sup.9 Pa in a temperature range from -50.degree. C. to 150.degree. C.Type: GrantFiled: June 23, 1997Date of Patent: May 25, 1999Assignee: Herberts Gesellschaft mit Beschrankter HaftungInventors: Michael Osterhold, Werner Lenhard, Wilfried Collong, Willi Schlesing
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Patent number: 5905103Abstract: The invention relates to a process for the preparation of pigment paste resins for cathodically depositable coating compositions, wherein diepoxide compounds which contain polyoxyalkylene structures and alkyl and/or alkylene and/or hydroxyalkyl radicals having more than 3 carbon atoms are first reacted to form epoxy resin/amine adducts and final products with oxazolidine structures are obtained by a partial or complete reaction of secondary amino groups with formaldehyde.Type: GrantFiled: March 15, 1993Date of Patent: May 18, 1999Assignee: Vianova Resins, AGInventors: Helmut Honig, Georg Pampouchidis, Willibald Paar, Herbert Matzer, Manfred Valtrovic
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Patent number: 5894071Abstract: Two-component adhesive-, sealing- or coating compositions are being described which are separately packed, and comprise the component A and the component D, whereby the component A is curing as soon as it gets in touch with water or the component D which contains the curing agent for the component A.The component D can be, or a component B containing an ingredient which is curing at the contact of water, or, possibly, at the contact with the component A, orthe component D can also be a mixture of solid matter and a volatile ingredient which is causing the cross-linking of the component A.The advantage of the novel two-component systems is that the component D is working as a curing agent for the component A, however, a surplus thereof is, or self-curing, or it does not leave a nuissance residue in the cured composition.Type: GrantFiled: December 6, 1996Date of Patent: April 13, 1999Assignee: Sika AG, vorm. Kaspar Winkler & Co.Inventors: Peter Merz, Norman E. Blank, Hans-Peter Tschan, Reinhard Ernst Wappmann, Lutz Zabel
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Patent number: 5883276Abstract: An improved aqueous electrocoating composition that contains an anticrater agent which is a reaction product of polyoxyalkylene diamine and glycidoxy alkyl alkoxy silane which is hydrolyzed and has a number average molecular weight of about 700-5,000; electrodeposited finishes are formed that have a significant reduction in craters and are smooth and even finishes.Type: GrantFiled: October 22, 1997Date of Patent: March 16, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Allisa Gam, Ding Yu Chung
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Patent number: 5880178Abstract: The present invention comprises a curable composition comprising:(i) a blocked reactive component comprising a blocked isocyanate or a blocked isothiocyanate;(ii) a functional compound containing reactive hydrogen;(iii) a triorganotin catalyst for promoting the reaction of the blocked reactive component with the functional compound.The composition may also be admixed with water.Type: GrantFiled: November 7, 1996Date of Patent: March 9, 1999Assignee: Elf Atochem North America, Inc.Inventors: Emily Carol Bossert, Wayne Ranbom, William Albert Larkin
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Patent number: 5874490Abstract: There is disclosed a self-dispersing curable epoxy resin composition comprising the addition product of reactants comprising (a) 1.0 reactive equivalent of an epoxy resin, (b) from about 0.40 to 0.95 reactive equivalents of a polyhydric phenol, and (c) from about 0.005 to 0.5 reactive equivalents of an amine-epoxy adduct comprising the addition product of reactants comprising 1.0 reactive equivalent of a polyepoxide and from about 0.3 to 0.9 reactive equivalents of a polyoxyalkyleneamine with the structural formulaH.sub.2 N--CH(R.sub.2)CH.sub.2 --O--R.sub.1 --CH.sub.2 CH(R.sub.2)--NH.sub. 2wherein:R.sub.1 represents a polyoxyalkylene chain having the structural formula:(CH.sub.2 --CH.sub.2 --O).sub.a --(CH.sub.2 --CH(R.sub.3)--O).sub.bwherein:R.sub.3 is a monovalent organic radical selected from the group consisting of C.sub.1 to C.sub.4 aliphatic hydrocarbons,`a` designates a number of ethoxy groups (CH.sub.2 --CH.sub.2 --O),`b` designates a number of monosubstituted ethoxy groups (CH.sub.2 --CH(R.sub.Type: GrantFiled: October 30, 1996Date of Patent: February 23, 1999Assignee: Henkel CorporationInventors: Kartar S. Arora, John G. Papalos, Grannis S. Johnson
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Patent number: 5859112Abstract: Process for making organic solvent-free aqueous crosslinkable polymer composition comprising: a) preparing an aqueous solution of an acid-functional olgiomer with Tg below 50.degree. C. and having crosslinker functional groups; b) conducting an aqueous emulsion polymerisation to make an aqueous emulsion of an olefinic hydrophobic polymer in the presence of the aqueous oligomer solution, the hydrophobic polymer having Tg at least 25.degree. C. higher than that of the oligomer and optionally crosslinker functional groups, and c) combining with a crosslinking agent reactable with the crosslinker groups of the oligomer and polymer, said composition having Koenig hardness of .gtoreq.40 sec and minimum film forming temperature (MFFT).ltoreq.55.degree. C. Also the aqueous composition so formed and its use in various applications. The aqueous composition has excellent properties and in particular an advantageous balance of MFFT and Koenig hardness.Type: GrantFiled: November 1, 1996Date of Patent: January 12, 1999Assignees: Zeneca Resins B.V., Zeneca LimitedInventors: Gerardus Cornelis Overbeek, Yvonne Wilhelmina Smak, Alfred Jean Paul Buckmann, John Christopher Padget
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Patent number: 5854312Abstract: Described are aqueous emulsions of active amino groups-displaying epoxide adduct hardeners for curing epoxy resin systems, which are obtained by converting an aqueous solution of a conventional hardener, which contains reactive amino groups and can emulsify the epoxy resin used for adduct formation, under increase of the amine-H-equivalent weight, to an emulsion by mixing with an epoxy resin having a functionality of 1,2-3,5. The viscosity generally is 5 to 40 Pa.s. The values lie on an emulsion viscosity curve with a rising and falling viscosity profile. The hardeners are especially suitable for curing aqueous epoxy resin systems and for application together with epoxy resins as additive for hydraulic binders such as cement.Type: GrantFiled: July 26, 1996Date of Patent: December 29, 1998Assignee: Air Products and Chemicals, Inc.Inventor: Achim Klippstein
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Patent number: 5847027Abstract: Hardeners for elastic epoxy resin systems, obtained by reaction of(A) reaction products of epoxide compounds (A1) with sterically hindered amines (A3), and/or(B) cyclic carbonates prepared from the compounds (A) and carbon dioxide, and/or(C) cyclic carbonates prepared from reaction products(C1) of epoxide compounds (C11) with polyoxyalkyleneamines (C13) and carbon dioxide, and, if desired(D) additional epoxide compounds or unreacted residues of the initial epoxides for the preparation of (A), (B) and (C), with(E) polyamines having at least two secondary amino groups, and(F) if desired, further reactants, each of the epoxide compounds (A1) and (C11) containing at least two epoxide groups, and it being possible for monoepoxides to be admixed in each case, if desired.Type: GrantFiled: April 1, 1996Date of Patent: December 8, 1998Assignee: Vianova Resins GmbHInventors: Manfred Marten, Claus Godau, Uwe Neumann
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Patent number: 5820987Abstract: An electrodepositable composition that has: (A) an active hydrogen-containing cationic resin, electrodepositable on a cathode, having: (1) a polyepoxide; (2) an oxygen-substituted diamine compound having the following formula: ##STR1## where n is an integer from 2 to 4; and where R.sup.1 or R.sup.2 are the same or different and either one or both contain at least one oxygen and are alkyl, cycloalkyl, substituted alkyl, or substituted cycloalkyl having from 1 to 6 carbon atoms, or R.sup.1 and R.sup.2 are alkanol groups having from 2 to 6 carbon atoms, or R.sup.1, R.sup.2, and the N atom form a cyclic group which is substituted or unsubstituted such as morpholine and 1-(3-aminopropyl) imidazole; and (B) at least partially blocked isocyanate or polyisocyanate curing agent. The diamine compound of Formula I can be used alone or in conjunction with one or more secondary amines, nonhydroxy group containing amines and/or amines with ring structures.Type: GrantFiled: August 21, 1996Date of Patent: October 13, 1998Assignee: PPG Industries, Inc.Inventors: Marvin L. Kaufman, Patrick O'Neill, Richard F. Karabin, Gregory J. McCollum
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Patent number: 5798398Abstract: It has been found that non-blushing coatings of high gloss, long pot life and fast cure time may be obtained by using an epoxy curing agent which comprises an epichlorohydrin-metaxylylenediamine reaction product selected from the group consisting of N,N'-bis(3-aminomethylbenzyl)-2-hydroxytrimethylenediamine, the higher oligomers of N,N'-bis(3-aminomethylbenzyl)-2-hydroxytrimethylenediamine and mixtures thereof and a melting point depressant such as a benzyl alcohol or water and an alcohol solvent and, optionally, a tertiary amine such as N,N'-bis(3-(dimethylamino)propyl)-urea.Type: GrantFiled: October 18, 1996Date of Patent: August 25, 1998Assignee: Henkel CorporationInventors: Shailesh Shah, Ronald J. Cash, Ronald LaFreeda, James Aloye, Joseph L. Mulvey