With Carboxylic Acid Or Derivative Reactant Or Polymer Derived Therefrom Patents (Class 525/488)
  • Patent number: 4755542
    Abstract: Flexible thermoplastic epoxy resins are prepared by reacting (1) an advanced epoxy resin prepared by reacting a mixture of an aromatic based epoxy resin and an aliphatic based epoxy resin with a polyhydric phenol in the presence of an advancement catalyst with (2) a monocarboxylic acid or anhydride thereof; reacting the resultant product with a mixture of an aromatic based epoxy resin and a monofunctional material reactive with vicinal epoxy groups; and reacting the resultant product with a carboxyl terminated elastomer. These resins are particularly useful in formulating pavement marking paints.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: July 5, 1988
    Assignee: The Dow Chemical Company
    Inventors: Michael B. Cavitt, David J. Duncan
  • Patent number: 4751267
    Abstract: A high solids coating composition comprises a low molecular weight polymeric blend of acrylic polymer, polyester polymer, and amine cross-linking resin. The acrylic and polyester polymers contain primary hydroxyl groups adapted to coreact and cross-link with active amine cross-linking resin such as aminoplast resins. All of the polymers have a number average molecular weight below about 3000.
    Type: Grant
    Filed: May 1, 1987
    Date of Patent: June 14, 1988
    Assignee: The Glidden Company
    Inventor: Wellington F. Berghoff
  • Patent number: 4711934
    Abstract: A process for producing self-crosslinking cationic paint binders, water-dilutable upon protonation, on the basis of urea group carrying reaction products of modified phenols and epoxy resins as well as with the binders produced according to the process and their use in stoving paints, particularly in electrodeposition paints is described. The process is characterized in that either an aminoalkylation product of a phenol and a semi-blocked diisocyanate carrying an average of at least one secondary amino group, or a substituted urea prepared from a semi-blocked diisocyanate and an amine, which is further reacted with formaldehyde and a phenol, are reacted with an epoxy compound. The paints formulated with these products, at stoving temperatures of from 150.degree. to 170.degree. C., give films with excellent corrosion resistance and adhesion.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: December 8, 1987
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Michael Honel, Johann Gmoser
  • Patent number: 4686248
    Abstract: The preparation of water-thinnable thermosetting resin binder compositions for coatings is described wherein a polyglycidyl ether prepared by reacting a multifunctional polyglycidyl ether with a monofunctional phenol is reacted with a dicarboxylic acid in the presence of an esterification catalyst.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: August 11, 1987
    Assignee: Shell Oil Company
    Inventors: Jurrianus Bekooij, Petrus G. Kooijmans, Werner T. Raudenbusch, Stephen A. Stachowiak
  • Patent number: 4680346
    Abstract: A coating composition contains an organic polyol, a polyepoxide, a blocked polyisocyanate crosslinking agent, and a phenolic resin. The coating composition also can be formulated as a two package coating composition with a free polyisocyanate crosslinking agent. The composition is flexible, having an elongation of at least 10 percent when cured. This coating composition is particularly suitable as a primer in preparing substrates with a multilayer coating having good flexibility.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: July 14, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Dennis W. Carson, Robert J. Schmitt, Carl A. Seneker, Thomas A. Van Kuren, David R. Wallace
  • Patent number: 4611036
    Abstract: An epoxy resin composition having excellent handling properties, solvent resistance and heat resistance and particularly excellent low-temperature curability is provided which comprises (A) a polyfunctional epoxy resin having an epoxy equivalent of 160 to 2,000 obtained by reacting an epoxy resin having an epoxy equivalent of 100 to 800 with a molecular weight increasing agent containing 2.1 to 10 functional groups (phenolic hydroxyl groups) on an average per molecule and (B) a curing agent for the epoxy resin) as essential ingredients.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: September 9, 1986
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hisashi Sekiguchi, Norio Kobayashi, Hideo Ohgishi
  • Patent number: 4609686
    Abstract: 100 percent solids epoxy, nitrile coating compositions comprising:(a) epoxy resins, and(b) epoxy-nitrile monomers which are useful for protective coatings.The invention further includes a process for producing the 100 percent solids epoxy nitrile coating compositions comprising:(1) forming a mixture of the epoxy resins with the epoxy nitrile monomers and curing agents,(2) applying the mixture to a substrate to form a coating, and(3) curing the coating so that in situ copolymerization of the epoxy resin and epoxy-nitrile monomer results in a multifunctional epoxy nitrile coating system.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: September 2, 1986
    Assignee: The Standard Oil Company
    Inventors: Paul Giordano, Jr., Richard C. Smierciak
  • Patent number: 4601769
    Abstract: A method is described for stabilizing the viscosity of a liquid epoxy-anhydride system which is a blend of a liquid epoxy resin, a liquid anhydride curing agent and a quaternary ammonium salt promoter for an epoxy-anhydride reaction. This system is especially useful in the manufacture of tubing, piping and other geometric structures. The method employs at least one of the following modifications:(1) adding a minor amount of a solid epoxy resin to the liquid epoxy resin;(2) adding to the liquid anhydride a minor amount of solid anhydride of high reactivity;(3) adding to the epoxy-anhydride system a solid resinous particulate material in finely ground form which is capable of reacting with the epoxy resin and acid anhydride, and is soluble in the epoxy-anhydride system at temperatures below the gelation temperature; and(4) adding a metallo-organic compound which lowers the initiation temperature or accelerates the epoxy-anhydride reaction.
    Type: Grant
    Filed: September 27, 1985
    Date of Patent: July 22, 1986
    Inventor: Ronald L. DeHoff
  • Patent number: 4596840
    Abstract: Mixture for the production of acid-resistant sealing materials or acid-resistant impregnating materials based on epoxy resins, resols, hardening catalysts and further customary additives, which are in the form of a cement or impregnating solution and contain, as essential constituents, (A) at least one bifunctional, low-molecular epoxy resin having an epoxide equivalent weight between 87 and 1,000, (B) at least one resol formed from at least one trifunctional phenol and formaldehyde in a molar ratio of 1:1 to 1:3, having a viscosity between 50 and 2,500 mPa.s at 20.degree. C. and having a solids content of at least 50% by weight, and (C) hardening catalysts, cements also containing (D) fillers, in addition, and a process for the preparation of hardening products from the compounds. Thus, for example, cements or impervious, initially porous shaped articles which are resistant to solvents and weak acids and which have a low shrinkage after processing, are obtained.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: June 24, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hesse, Klaus Rauhut
  • Patent number: 4578438
    Abstract: Water-dilutable resinous products are obtained by reacting(A) a resin having at least one phenolic hydroxyl group and a free position ortho and/or para to a phenolic hydroxyl group, and containing a residue formed by polymerization of a vinyl monomer in the resin or in a precursor thereof,(B) an aldehyde, and(C) sulphurous acid or an organic acid containing a primary or secondary amino group or a mercaptan group and a carboxylic, sulphonic or phosphonic acid group, or a water-soluble salt thereof.Aqueous compositions containing the resinous products and, if required, and aminoplast, a phenoplast or a blocked polyisocyanate, usually together with a minor amount of an organic solvent, are useful in the formation of surface coatings.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: March 25, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Christopher G. Demmer, Roderick D. Hathaway
  • Patent number: 4567102
    Abstract: A hot melt, non-aqueous glass size composition consists of an ethylene-ethylacrylate copolymer, a micro-crystalline wax, a phenolic-modified terpene resin and a silane.
    Type: Grant
    Filed: May 24, 1984
    Date of Patent: January 28, 1986
    Assignee: Owens-Corning Fiberglas Corporation
    Inventors: Jean-Claude Pollet, Gordon P. Armstrong, Martin C. Flautt
  • Patent number: 4552935
    Abstract: Heat-curable mixtures containing (a) epoxy compounds having on average more than one 1,2-epoxy group per molecule, (b) monoimides or polyimides of specific unsaturated dicarboxylic acids of the formula I ##STR1## wherein A is an x-valent aromatic or aliphatic radical, R.sup.1 is hydrogen or methyl, and x is 1, 2 or 3, and (c) products of condensing specific phenols, specific amines and aldehydes or ketones in an acid medium.The novel curable mixtures have a long shelf life and give rise to moulded materials which are highly resistant to chemicals and resistant to boiling water.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: November 12, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Theobald Haug, Friedrich Stockinger
  • Patent number: 4543376
    Abstract: Heat-curable surface-coating agents useful in organically dissolved baking finishes, for powder coating and for cathodic electrocoating contain, as a binder, a mixture of a polyadduct, polycondensate or other polymer which has an average molecular weight M.sub.n of from 500 to 10,000 and, per molecule, on average two or more OH and/or NH groups, and a reaction product of a polyamine which contains on average two or more primary amino groups per molecule and a cyclic carbonic acid ester of the formula (I) ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each are hydrogen, methyl or ethyl.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: September 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Schupp, Werner Loch, Rolf Osterloh, Klaas Ahlers
  • Patent number: 4532309
    Abstract: A stable water soluble epoxy resin suitable for use as a coating material is made by grafting an acid functional vinyl monomer onto unsaturated functional sites on an epoxy resin backbone.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: July 30, 1985
    Assignee: Parker Chemical Company
    Inventor: Andreas Lindert
  • Patent number: 4526939
    Abstract: High solids thermosetting organic solvent solution coating compositions are disclosed which are particularly useful for sealing the pores in fiber reinforced plastics. These compositions contain a mixture of resins comprising (1) from 30% to 70% of one or more hydroxy functional resins having a number average molecular weight of at least about 700, a Gardner bubble viscosity less than about Z.sub.4 measured in methyl ethyl ketone at 90% solids at 25.degree. C., and at least 5% of the hydroxy groups thereof being primary hydroxy groups, (2) from 10% to 70% of low molecular weight epoxy ester made by esterifying one or more resinous polyepoxides having a 1,2-epoxy equivalency of at least 1.2 with an approximately stoichiometric proportion of monocarboxylic fatty acid to provide an essentially epoxy-free ester having a Gardner bubble viscosity less than Z.sub.4 at 75% solids in xylol at 25.degree. C.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: July 2, 1985
    Assignee: DeSoto, Inc.
    Inventors: Ronald J. Lewarchik, Kevin P. Murray, Marcella G. Donovan, Arthur T. Jones
  • Patent number: 4517343
    Abstract: A cathodic electrocoating binder comprises a mixture of(A) from 50 to 95 percent by weight of one or more polyadducts, polymers and/or polycondensates which possess basic nitrogen groups and(B) from 50 to 5 percent by weight of one or more amide-amines obtained by reacting monocarboxylic and/or dicarboxylic acids, or their esters, with diamines which possess one primary and one secondary amino group per molecule, the secondary amino group carrying a .beta.
    Type: Grant
    Filed: November 15, 1982
    Date of Patent: May 14, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Schupp, Fritz E. Kempter
  • Patent number: 4511701
    Abstract: Curable epoxy resin compositions are provided resulting from the use of a silylnorbornane functional anhydride or imidoamine. The cured products show improved thermal and physical properties as compared to conventional curing agents.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: April 16, 1985
    Assignee: General Electric Company
    Inventor: Hong-Son Ryang
  • Patent number: 4497946
    Abstract: Epoxy phosphate-carboxyl copolymers substantially free of epoxy functionality and aqueous coatings containing the same are disclosed. These copolymers are formed by copolymerizing monoethylenically unsaturated monomers, including carboxyl-functional monomer, in an organic solvent solution containing an epoxy-functional epoxy phosphate, there being at least 5% of carboxyl-functional monomer and at least 10% of total monomers present in the copolymer. The copolymer is converted into a water soluble salt with volatile amine and phenoplast resins are preferably used to provide at least part of the curing agent.
    Type: Grant
    Filed: April 13, 1983
    Date of Patent: February 5, 1985
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4465806
    Abstract: The compositions disclosed herein comprise a mixture of:(1) An unsaturated polyester resin; such as the polymeric ester of maleic acid or anhydride and a glycol such as ethylene glycol; and(2) The reaction product of a polyepoxy compound, such as the diglycidyl ether of bisphenol-A, and an unsaturated monocarboxylic acid, such as acrylic or methacrylic acid, in which reaction product there remains unreacted at the time of mixing with said polyester resin at least 5 percent of the original epoxy groups of said polyepoxy compound.This mixture when molded or cured gives improvement with respect to thermal and humid aging as compared to similar compositions in which the epoxy groups of said reaction product are substantially all reacted prior to mixture with said unsaturated polyester resin. The flexural strength, in particular, of the compositions are better retained on aging without adverse effect on other properties.
    Type: Grant
    Filed: February 16, 1983
    Date of Patent: August 14, 1984
    Assignee: Plastics Engineering Company
    Inventor: Chung J. Lee
  • Patent number: 4465816
    Abstract: A stable, water soluble epoxy resin suitable for use as a coating material is made by grafting a thio-acid onto an unsaturated functional site on an epoxy resin backbone.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: August 14, 1984
    Assignee: Parker Chemical Company
    Inventor: Andreas Lindert
  • Patent number: 4433119
    Abstract: There are described liquid compositions of a hemiformal of phenol and/or a hemiformal of a methylolated phenol with a miscible polymers such as phenol-formaldehyde resoles, phenol-formaldehyde, novolacs, aromatic polyesters, unsaturated polyesters, poly(aryl-ethers), aromatic polycarbonates urea-formaldehyde resins, or melamine-formaldehyde resins. The compositions are useful for forming thermoset plastic materials.
    Type: Grant
    Filed: January 19, 1982
    Date of Patent: February 21, 1984
    Assignee: Union Carbide Corporation
    Inventors: George L. Brode, Sui-Wu Chow
  • Patent number: 4385166
    Abstract: Novel vehicles for printing inks are thermoplastic alcohol-soluble low molecular weight poly(amide-ester) resins that are prepared by a two-step process from a dimerized fatty acid, a polyamine, and a bisphenol A-epichlorohydrin epoxy resin.
    Type: Grant
    Filed: November 9, 1981
    Date of Patent: May 24, 1983
    Assignee: Sun Chemical Corporation
    Inventors: Daniel J. Carlick, Arnold H. Gruben, Shih-chung Chen
  • Patent number: 4369306
    Abstract: A method for treating an olefin polymer, which comprises contacting an olefin polymer obtained by polymerizing an olefin in the presence of a catalyst composed of (A) a highly active transition metal compound, (B) an organoaluminum compound and (C) a carbonyl- or Si-containing electron donor, with (D) an organometallic compound of a metal of Groups I to III of the periodic table after the polymerization. This method can markedly reduce the amount of an electron donor remaining in an olefin polymer after polymerization, the electron donor being an ingredient of a catalyst used in the polymerization and constituting the main cause of an offensive odor which the resulting polymer gives off.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: January 18, 1983
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Akinori Toyota, Norio Kashiwa
  • Patent number: 4343924
    Abstract: Disclosed is an improved method for coating a substrate with a film of a coating composition rapidly curable at room temperature in the presence of a vaporous tertiary-amine catalyst. The pot life of the coating composition is substantially increased without deleterious loss of properties of the ultimately cured film wherein the coating composition comprises three components. The first component is a phenol-functional condensation product of (a) a phenol-aldehyde reaction product bearing a plurality of methylol and phenol groups, and (b) a polyol, polycarboxylic acid, or polyepoxide, wherein the condensation product is reacted with a selective transmethylolating agent for substantially transforming residual methylol groups into non-active hydrogen groups. The second component is a multi-isocyanate cross-linking agent and the third component is an organic solvent. The coating composition is applied to a substrate and cured by exposure of the coated substrate to a vaporous tertiary amine catalyst.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: August 10, 1982
    Assignee: Ashland Oil, Inc.
    Inventor: Gary L. Linden
  • Patent number: 4317858
    Abstract: Disclosed is a wire enamel blend which is curable to the B-stage with UV light then to the C stage with heat. The blend comprises up to about 40% of an acrylated epoxy dissolved in a monoacrylate, about 2 to about 26% of an acrylated polybutadiene, about 3 to about 26% of an acrylated polyester-amide-imide dissolved in a monoacrylate and in an unsatured diester, about 30 to about 65% of an end-blocked urethane dissolved in a monoacrylate and hydroxy terminated unsaturated diesters, up to about 15% of a cresol formaldehyde dissolved in monoacrylates, about 1.5 to about 5% of a UV photoinitiator, up to about 5% of an acrylated methoxymethyl melamine, and up to about 0.1% of a flow control agent.
    Type: Grant
    Filed: June 27, 1980
    Date of Patent: March 2, 1982
    Assignee: Westinghouse Electric Corp.
    Inventor: Frank A. Sattler
  • Patent number: 4296219
    Abstract: A bisimide-ether compound having the general formula is obtained by reacting an ethylenically unsaturated dicarboxylic acid anhydride, a diamine compound and a phenolic compound having in the molecule at least two hydroxyl groups, or by reacting a prepolymer of the anhydride and diamine compound with the phenolic compound: ##STR1## wherein R.sub.1 is a group containing at least two carbon atoms, R.sub.2 is a group containing at least two carbon atoms, R'.sub.2 is a group containing at least two carbon atoms and a carbon-carbon double bond, R.sub.3 is an aromatic group, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R.sub.1, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R.sub.2 or R'.sub.2, the oxygen atoms between the groups R.sub.2 and R.sub.3 being directly connected to an aromatic nucleus of the group R.sub.3, and n is an integer of zero, one or more than 1.
    Type: Grant
    Filed: January 22, 1979
    Date of Patent: October 20, 1981
    Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.
    Inventors: Akio Takahashi, Yutaka Itoh, Motoyo Wajima, Hirosada Morishita, Akio Nishikawa
  • Patent number: 4287234
    Abstract: A desensitizing ink for wet offset printing on the acceptor surface of a chemical duplicating set of superimposed sheets where one of the sets has an electrophilic acceptor coating and the other a nucleophilic coating for producing a chromogenic reaction wherein the nucleophilic desensitizing ink contains an alkoxylated nucleophilic compound which permits a continuous ink transfer to the water repellant zones of the wetted impression plate of an offset press and simultaneously neutralizes the corresponding zones of the acceptor surface.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: September 1, 1981
    Assignee: Sipca Holding S.A.
    Inventors: Albert Amon, Roger Weil, Paul Heinzer
  • Patent number: 4278780
    Abstract: A thermosetting resin composition suitable for use as a molding material comprising (a) a reaction product mixture obtained by preferably reacting 1 mole of a dicarboxylic acid anhydride having ethylenic carbon-carbon double bond such as maleic anhydride with 2-20 moles of a diamine such as 4,4'-diaminodiphenylmethane in a molten state and (b) an epoxy compound having more than one 1,2-epoxy group on the average gives a cured product excellent in heat resistance, etc., when cured with heating at a temperature of 150.degree. to 200.degree. C.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: July 14, 1981
    Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.
    Inventors: Akio Nishikawa, Hiroshi Suzuki, Hisashi Kohkame
  • Patent number: 4252935
    Abstract: Esters of glycidyl polyethers of saturated phenols are especially useful in coating compositions having a low organic solvent content. The esters are the reaction products of from about 0.5 to about 1.5 equivalents of a saturated monocarboxylic acid with each epoxy group in a diglycidyl polyether of phenols where the aromatic rings of the phenols are saturated.
    Type: Grant
    Filed: July 31, 1979
    Date of Patent: February 24, 1981
    Assignee: PPG Industries, Inc.
    Inventors: Carl C. Anderson, William J. Birkmeyer, Roger M. Christenson, Rostyslaw Dowbenko, Ronald J. Lewarchik
  • Patent number: 4247659
    Abstract: Water soluble epoxy ester copolymers adapted for sanitary can use comprise an hydroxy functional epoxy ester of a polyepoxide having an average molecular weight of about 300 to about 1100 and a 1,2-epoxy equivalency of about 1.4 to about 2.0, esterified with an at least approximately stoichiometric proportion, based on epoxide functionality, of monocarboxylic acid selected from benzoic acid, C.sub.1 -C.sub.8 alkyl substituted benzoic acid, and C.sub.6 -C.sub.10 alkanoic acid, the esterification reaction being continued to provide an acid number of less than 20, this hydroxy functional epoxy ester is polyesterified with from 1.
    Type: Grant
    Filed: March 9, 1979
    Date of Patent: January 27, 1981
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4200705
    Abstract: A curable vinyl ester composition is prepared by the process wherein an organic hydroxy compound is reacted with a stoichiometric excess of an ethylenically unsaturated carboxylic acid and, after substantial completion of that esterification, reacting an oxirane compound with the unesterified carboxyl groups.
    Type: Grant
    Filed: January 2, 1979
    Date of Patent: April 29, 1980
    Assignee: The Dow Chemical Company
    Inventor: Rhetta Q. Davis
  • Patent number: 4192931
    Abstract: A process for producing a furan-epoxy powder-like binder comprising reaction of an epoxy diane resin (100 parts by weight) with a ketone of the furan series (40 to 500 parts by weight) and a modifying agent (60 to 500 parts by weight). As the ketone of the furan series use is made of monofurfurylideneacetone, difurfurylideneacetone, difurfurylidenecyclohexanone, a mixture of monofurfurylidenacetone with difurfurylidenacetone, 1,9-di-(.alpha.-furyl)-nonanetetraene-1,3,6,8-one-5, or 1,5-di-(.alpha.-furyl)-2,4-dimethylpentadiene-1,4-one-3. As the modifying agent use is made of a phenolformaldehyde resin or anhydrides of dibasic carboxylic acids. The reaction is carried out at a temperature within the range of from 130.degree. to 180.degree. C. in the presence, when required, of trifurylborate (10 to 30 parts by weight). The resulting product is cooled to a temperature of at most 30.degree. C. and disintegrated to a powder-like condition.
    Type: Grant
    Filed: August 7, 1978
    Date of Patent: March 11, 1980
    Inventors: Gennady D. Varlamov, Juldash Mamatov, Ildgam A. Bekbulatov, Shavkat Madaliev