Mixed With Carboxylic Acid Or Derivative Reactant Or Polymer Therefrom Patents (Class 525/519)
  • Patent number: 4775725
    Abstract: There is provided a novel product having the formula: ##STR1## where "polymer" is an amine functional polymer, such as amine terminated polyethylene imine, amine terminated polyalkylene glycols, amine terminated anilineformaldehyde, amine terminated nylons, amine functional silicones; R.sup.1, R.sup.2, and R.sup.3 are C.sub.1 -C.sub.8 monovalent hydrocarbyl radicals, m is 1 to 3 and n is 1 to 10.
    Type: Grant
    Filed: April 3, 1987
    Date of Patent: October 4, 1988
    Assignee: PCR, Inc.
    Inventors: Ralph J. DePasquale, Michael E. Wilson
  • Patent number: 4758615
    Abstract: Polymers which contain urethane groups and are capable of being crosslinked by extraneous crosslinking agents, solutions thereof and aqueous dispersions thereof, prepared without the use of isocyanates by reacting polyamino compounds with polycarbonates and, if appropriate, reacting the reaction product further with polycarboxylic acids to give products having an acid number between 0 and 100, and, if appropriate, neutralizing the resulting products partly or completely by adding basic compounds, preferably organic bases, and, if appropriate, mixing the partly or completely neutralized products vigorously with an amount of water such that aqueous polymer dispersions having a solids content of up to 75% by weight, relative to the dispersion, are obtained.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: July 19, 1988
    Assignee: Hoechst AG
    Inventors: Dieter Engel, Christoph Just, Gerhard Brindopke, Gerd Walz
  • Patent number: 4740566
    Abstract: A thermosetting high gloss color-keyed primer-surfacer comprises 50-70% by weight of a film-forming component consisting essentially of, by weight, 40-70% of a polyester polyol formed by reaction of dimethyl 1,4-dicyclohexanedicarboxylate, dicarboxylic acids, and branched-chain glycols; 20-40% of an aminoplast resin; and 5-10% of an epoxy resin.
    Type: Grant
    Filed: May 23, 1986
    Date of Patent: April 26, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Henry S. Tremper, III
  • Patent number: 4736000
    Abstract: A method for curing an aromatic polythioether sulfone, which comprises mixing an aromatic polythioether sulfone polymer with a member selected from the group consisting of (a) a compound having at least two epoxy, isocyanate or maleimide groups per molecule, (b) an aminoplast resin, (c) a metal chelate compound of acetylacetone, and (d) a halide of a metal belonging to Group VIII or IB of the Periodic Table, followed by heat treatment.
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: April 5, 1988
    Assignee: Asahi Glass Company Ltd.
    Inventors: Josho Kashiwame, Shigeyuki Kozawa, Takao Doi, Nobuyuki Tamai
  • Patent number: 4714657
    Abstract: A protective coating composition containing certain polyester polyols and an aminoplast derivative is applied to a thermoplastic substrate to produce a thermoformable article having mar- and solvent-resistance.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: December 22, 1987
    Assignee: General Electric Company
    Inventors: Clayton B. Quinn, Richard R. McClish, James E. Moore
  • Patent number: 4680347
    Abstract: Thermosettable prepolymers or resins are prepared by reacting (1) a pyrazine compound containing at least two substituent groups which have a hydrogen atom attached to a carbon atom which is attached to the ring such as tetramethylpyrazine, (2) a material containing at least two aromatic aldehyde groups, and (3) at least one of (a) a nitrogen containing aromatic heterocyclic compound containing at least one hydrogen atom attached to a carbon atom attached to the ring and a polymerizable unsaturated group such as 2-methyl-5-vinylpyridine or (b) an aldehyde containing at least one polymerizable unsaturated group such as 4-isopropenyl-1-cyclohexene-1-carboxaldehyde. These prepolymers or resins are curable to thermoset products having good mechanical and thermal properties by heat and pressure or by homopolymerization or copolymerization with N,N'-bis-imides such as 1,1'-(methylenedi-4,1-phenylene)-bimaleimide. The prepolymers are suitable for preparing composites.
    Type: Grant
    Filed: March 17, 1986
    Date of Patent: July 14, 1987
    Assignee: The Dow Chemical Company
    Inventor: Duane S. Treybig
  • Patent number: 4629770
    Abstract: Thermosettable prepolymers or resins are prepared by reacting (1) a pyrazine compound containing at least two substituent groups which have a hydrogen atom attached to a carbon atom which is attached to the ring such as tetramethylpyrazine, (2) a material containing at least two aromatic aldehyde groups, and (3) at least one of (a) a nitrogen containing aromatic heterocyclic compound containing at least one hydrogen atom attached to a carbon atom attached to the ring and a polymerizable unsaturated group such as 2-methyl-5-vinylpyridine or (b) an aldehyde containing at least one polymerizable unsaturated group such as 4-isopropenyl-1-cyclohexene-1-carboxaldehyde. These prepolymers or resins are curable to thermoset products having good mechanical and thermal properties by heat and pressure or by homopolymerization or copolymerization with N,N'-bis-imides such as 1,1'-(methylenedi-4,1-phenylene)-bismaleimide. The prepolymers are suitable for preparing composites.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: December 16, 1986
    Assignee: The Dow Chemical Company
    Inventor: Duane S. Treybig
  • Patent number: 4598021
    Abstract: A protective coating composition containing a polycaprolactone polyol and an aminoplast derivative is applied to a thermoplastic substrate to produce a thermoformable article having abrasion resistance, solvent resistance and weatherability.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: July 1, 1986
    Assignee: General Electric Company
    Inventor: James E. Moore
  • Patent number: 4578439
    Abstract: Styryl pyridine and styryl pyrazine cyanates are prepared by cyanating the reaction product of (A) a substituted pyridine and/or pyrazine with (B) a substituted aromatic aldehyde with the proviso that at least one of the components (A) or (B) contains a hydroxyl group which is susceptible to being cyanated. These cyanates can be homopolymerized or copolymerized with other materials to produce polymers having excellent high temperature resistance, good mechanical strength and excellent processability.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: March 25, 1986
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4575542
    Abstract: Thermosettable compositions are disclosed which are prepared by reacting (A) a pyridine compound containing at least two substituent groups which have at least one hydrogen atom attached to a carbon atom which is attached to the ring or mixture of such pyridines; (B) at least one material having at least two aldehyde groups; and (C) at least one aldehyde containing at least one polymerizable unsaturated group; wherein components (A), (B) and (C) are employed in quantities which provide a mole ratio of (C):(B):(A) of from about 0.25:0.25:1 to about 4:4:1. These thermosettable compositions can be cured by heat and pressure or by homopolymerization in the presence of or by copolymerization with an N,N'-bis-imide. The compositions are useful as light weight fire resistant interior and exterior parts or panels for the aerospace and/or aircraft industry and the like.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: March 11, 1986
    Assignee: The Dow Chemical Company
    Inventor: Duane S. Treybig
  • Patent number: 4552936
    Abstract: A protective coating composition containing a polycaprolactone polyol and an aminoplast derivative is applied to a thermoplastic substrate to produce a thermoformable article having abrasion resistance, solvent resistance and weatherability.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: November 12, 1985
    Assignee: General Electric Company
    Inventor: James E. Moore
  • Patent number: 4518746
    Abstract: An essentially linear polyester oligomer having hydroxyl and carboxyl terminal groups for subsequent cure and its production are disclosed. This polyester oligomer is produced by first adducting approximately equimolar amounts of diol carrying two primary hydroxyl groups and a dicarboxylic acid anhydride to form an hydroxy acid. The carboxyl groups of this hydroxy acid are then esterified by reaction with an approximately stoichiometric proportion of diol carrying one primary hydroxyl group and one secondary hydroxyl group, the stoichiometry being based on the total hydroxyl content of the diol and the carboxyl content of the hydroxy acid, to form an hydroxyl-terminated oligomer. This hydroxyl-terminated oligomer is then adducted with a polycarboxylic acid monoanhydride having a carboxyl functionality of at least 3, this monoanhydride being used in an amount of 0.01 to 0.15 equivalents of anhydride per hydroxyl equivalent in the hydroxyl-terminated oligomer.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: May 21, 1985
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah, Ronald J. Lewarchik, Kevin P. Murray
  • Patent number: 4499255
    Abstract: Epoxy resins are prepared by reacting an excess of an epihalohydrin with a phenolic hydroxyl-containing compound in the presence of the incremental addition of a basic catalyst while removing water by codistilling with a solvent and epihalohydrin.
    Type: Grant
    Filed: August 16, 1983
    Date of Patent: February 12, 1985
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Ha Q. Pham, James L. Bertram
  • Patent number: 4465815
    Abstract: A novel polyhydroxy oligomer crosslinkable with amine-aldehyde to form a coating composition adapted for use as an automotive topcoat which upon curing forms a hard, glossy, durable coating with outstanding weatherability and excellent resistance to solvents and water. The coating composition comprises:(A) a polyhydroxy oligomer having a number average (M.sub.n) molecular weight of between about 300-2000 and being the reaction product of:(i) an acid ester made by reacting(a) a C.sub.3 -C.sub.10 aliphatic branched diol, and(b) an alkyl hexahydrophthalic anhydride, wherein (a) and (b) are combined in the reaction mixture in amounts and under conditions sufficient to result in reaction in a molar ratio of greater than 1:1 up to 1:2; and(ii) a monoepoxide C.sub.2 -C.sub.10 monomer, the monomer is included in an amount sufficient to provide reaction of about 1.0 epoxide groups for each acid group of the acid ester;(B) an amine-aldehyde crosslinking agent; and(C) optionally a hydroxy functional additive.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: August 14, 1984
    Assignee: Ford Motor Company
    Inventor: Mohinder S. Chattha
  • Patent number: 4404332
    Abstract: Amino-formaldehyde products with activated carboxylic ester groups cross-link compounds containing pendant primary or secondary amine groups.This is a continuation, of application Ser. No. 232,455, filed Feb. 9, 1981, which is a continuation of Ser. No. 128,613, filed 3/10/80, which is a division of Ser. No. 32,982, filed 4/25/79, which is a continuation-in-part of Ser. No. 926,762, filed 7/21/78, all now abandoned.
    Type: Grant
    Filed: October 26, 1982
    Date of Patent: September 13, 1983
    Assignee: American Cyanamid Company
    Inventors: Girish G. Parekh, Werner J. Blank, Peter J. Schirmann
  • Patent number: 4396733
    Abstract: The present invention relates to new azulmic acids stabilized by condensation with carbonyl compounds, several processes for their preparation and their use for various purposes.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: August 2, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kuno Wagner, Kurt Findeisen
  • Patent number: 4395521
    Abstract: Latent catalysts comprising the phenyl esters of certain carboxylic acids are disclosed for use in the cure thermosetting resins curable by an acid catalyst.
    Type: Grant
    Filed: January 20, 1982
    Date of Patent: July 26, 1983
    Assignee: Union Carbide Corporation
    Inventors: Sui-Wu Chow, George L. Brode
  • Patent number: 4384070
    Abstract: Pigmented coating solutions are disclosed which deposit coatings possessing improved resistance to ultraviolet radiation-induced auto-oxidation. These solutions contain organic solvent, including aromatic hydrocarbon solvent, having dissolved therein an aromatic hydrocarbon-soluble, normally liquid, polysulfide or polydisulfide derivative having terminal -SH groups which have been reacted with a monofunctional reactant providing a C.sub.1 -C.sub.22 alkyl terminal group to provide an essentially nonreactive derivative. The solvent also has dissolved therein a polar polymeric binder (preferably thermosetting) which degrades by a photo-oxidative mechanism and which has only limited compatibility with the derivative. The pigment protects the bulk of a deposited coating, and the limited compatibility causes a heated film of the coating solution to stratify as the solvent evaporates to concentrate the derivative at the surface of the cured coating to protect the same.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: May 17, 1983
    Assignee: DeSoto, Inc.
    Inventors: Joseph E. Gaske, Thomas H. Plaisance, Hannu K. Pennanen
  • Patent number: 4380611
    Abstract: Cross-linking agents are produced by reacting an ester of a di- or poly-carboxylic acid with a molar excess of ammonium hydroxide, thereby forming a di- or polyamide, which in turn is then methylolated and etherified with a lower alkanol. These products are cross-linkers for resins such as alkyds, oil-free polyesters, acrylic which can be either acid or hydroxy functional, phenolics, epoxies or melamines.
    Type: Grant
    Filed: October 27, 1981
    Date of Patent: April 19, 1983
    Assignee: Cook Paint and Varnish Company
    Inventors: Howard J. Wright, Joseph H. Scherrer
  • Patent number: 4379911
    Abstract: Amino-formaldehyde products with activated carboxylic ester groups cross-link compounds containing pendant primary or secondary amine groups.
    Type: Grant
    Filed: July 29, 1982
    Date of Patent: April 12, 1983
    Assignee: American Cyanamid Company
    Inventors: Girish G. Parekh, Werner J. Blank, Peter J. Schirmann
  • Patent number: 4345052
    Abstract: Method for manufacturing polyether ester amides by polycondensing at ordinary or reduced pressure, optionally in the presence of catalysts. A hot melt of:(a) polyamides having carboxyl end groups with polyethers having hydroxyl end groups and amino end groups;(b) polyamides having carboxyl end groups and polyethers having hydroxyl end groups;(c) polyamides having carboxyl end groups with polyethers having amino end groups; or(d) polyamides having amino end groups with polyethers having carboxyl end groups;is treated at temperatures from about 200.degree. to 300.degree. C. and at a water vapor pressure of about 5 to 25 bars with mechanical agitation and after water is removed by decompression the polycondensation of the polyether ester amide is carried out.
    Type: Grant
    Filed: July 10, 1980
    Date of Patent: August 17, 1982
    Assignee: Chemische Werke Huls AG
    Inventors: Salih Mumcu, Hans J. Panoch
  • Patent number: 4343925
    Abstract: Coating compositions capable of liquid application to substrates consist essentially of a curable film forming polyol-containing component and an organic reactive diluent. The reactive diluent is an organic compound containing a primary or secondary hydroxyl group and further characterized by having a retained solids value of greater than about 80 percent, a hydroxyl equivalent weight of from about 180 to about 800, and a liquid viscosity of less than about 10 poise at 60.degree. C. The coating compositions can be formulated to contain little or no volatile organic solvent and/or water.
    Type: Grant
    Filed: December 7, 1979
    Date of Patent: August 10, 1982
    Assignee: PPG Industries, Inc.
    Inventors: Wen-Hsuan Chang, James B. O'Dwyer, John R. Peffer
  • Patent number: 4336297
    Abstract: An electrical laminate comprising layers of a polyester resin-impregnated fibrous cellulosic substrate is disclosed. The substrate is preimpregnated with a nitrogen-containing composition having (a) an N-methylol or N-lower alkoxymethyl group attached to said nitrogen atom, and (b) an unsaturated group capable of copolymerizing with a cross-linking monomer present in the polyester resin.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: June 22, 1982
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yasuo Fushiki, Masaharu Abe, Masakazu Uekita
  • Patent number: 4314918
    Abstract: Reactive diluents are derived from the reaction of a glycidyl ester and a hydroxyl and/or carboxyl functional compound. The diluents are useful in coating compositions together with crosslinking agents and, optionally, polyols.
    Type: Grant
    Filed: June 26, 1980
    Date of Patent: February 9, 1982
    Assignee: PPG Industries, Inc.
    Inventors: William J. Birkmeyer, Ronald J. Lewarchik, Joseph A. Klanica, Carl C. Anderson
  • Patent number: 4310447
    Abstract: Curable, modified aminotriazine condensation product prepared by reacting an aminotriazine condensation product pre-condensed to a dilutability ratio with water of 1:0.5 to 1:5, with 65 to 500% by weight, relative to the triazine, of a lactam of an aminocarboxylic acid having 3 to 18 carbon atoms, or a diaminedicarboxylate salt of a diamine having 2 to 18 carbon atoms and a dicarboxylic acid having 2 to 18 carbon atoms, or a mixture thereof, at a temperature of no more than 65.degree. C.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: January 12, 1982
    Assignee: Cassella Aktiengesellschaft
    Inventors: Wilhelm Weber, Wilhelm Adam
  • Patent number: 4279800
    Abstract: A pigment-containing high solids coating composition is prepared from a blend of ester diols as binder and a curing agent for the binder, characterized in that as ester diol there is used a mixture of (a) 20-80 mole % of a compound having the general formula: ##STR1## where R.sub.1 represents the group formed by abstraction of the two carboxyl group from a cycloaliphatic and/or aromatic dicarboxylic acid having 8 to 20 carbon atoms and R.sub.2 and R.sub.3 may be the same or different and represent a hydrogen atom and/or a hydrocarbon group having 1 to 9 carbon atoms, and m is a number of 1-4, and of (b) 80-20 mole % of a compound having the general formula ##STR2## where R.sub.4 represents the group formed by abstraction of the two carboxyl groups from a cycloaliphatic and/or aromatic dicarboxylic acid having 8 to 20 carbon atoms, and R.sub.5 represents the group formed by abstraction of the two hydroxyl groups from a terminal diol having 4 to 12 carbon atoms in the main chain, and n is a number of 1-4.
    Type: Grant
    Filed: April 15, 1980
    Date of Patent: July 21, 1981
    Assignee: Akzo NV
    Inventors: Ritse E. Boomgaard, Roelof Buter, Aleidus A. Kiffen
  • Patent number: 4271277
    Abstract: Thermosetting powder coatings comprising reactive polymers containing reactive carboxyl, hydroxyl, and/or amide groups and adapted to be cross-linked with aminoplast resins are substantially improved by the inclusion of at least about 0.25% by weight of a heat curing catalyst. The catalyst is an amine salt of cyclohexyl sulfamic acid.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: June 2, 1981
    Assignee: SCM Corporation
    Inventor: Robert F. Golownia
  • Patent number: 4271062
    Abstract: A pigment-containing high solids coating composition is prepared from a curing agent and and ester diol which is a mixture of (a) 20-80 mole % of a compound having the general formula: ##STR1## where R.sub.1 represents the group formed by abstraction of the two carboxyl groups from maleic acid and/or fumaric acid and/or a cycloaliphatic and/or aromatic dicarboxylic acid having 8 to 20 carbon atoms and R.sub.2 and R.sub.3 may be the same or different and represent a hydrogen atom and/or a hydrocarbon group having 1 to 9 carbon atoms, and m is a number of 1-4, and of (b) 80-20 mole % of a compound having the general formula ##STR2## where R.sub.4 represents the group formed by abstraction of the two carboxyl groups from maleic acid and/or fumaric acid and/or a cycloaliphatic and/or aromatic dicarboxylic acid having 8 to 20 carbon atoms, and R.sub.
    Type: Grant
    Filed: April 15, 1980
    Date of Patent: June 2, 1981
    Assignee: Akzo N.V.
    Inventors: Ritse E. Boomgaard, Roelof Buter, Aleidus A. Kiffen
  • Patent number: 4263181
    Abstract: The present invention relates to certain new azulmic acids stabilized by reaction with aminoplast-forming agents and carbonyl compounds or condensation products thereof, to a process for their preparation and to their use for various purposes.
    Type: Grant
    Filed: August 3, 1979
    Date of Patent: April 21, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kuno Wagner, Kurt Findeisen
  • Patent number: 4258105
    Abstract: A curing agent package is provided for polymercaptan-terminated polymers comprising selected metal oxides and organonitrogen accelerators and promoters commonly considered as rubber vulcanization accelerators. More specifically, sealant and coating compositions are prepared by curing a mixture comprising a mercaptan-terminated polyether-polyester liquid polymer, a curing agent package of a non-lead metal oxide curing agent and an organonitrogen accelerator or promoter, and, optionally, non-elastomeric materials.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: March 24, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Ralph P. Williams
  • Patent number: 4248753
    Abstract: Resinous compositions which are the Michael adducts of primary and/or secondary amines and polymers containing alpha, beta-ethylenically unsaturated moieties in conjugation with carbonyl moieties are disclosed. The compositions are depositable on substrates to form films. The films are amenable to oxidative and aminoplast cures and cure with light color. The compositions are desirable for use in cationic electrodeposition.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: February 3, 1981
    Assignee: PPG Industries, Inc.
    Inventors: Stephen L. Buchwalter, Joseph F. Bosso, Roger M. Christenson
  • Patent number: RE31022
    Abstract: Resinous compositions which are the Michael adducts of primary and/or secondary amines and polymers containing alpha, beta-ethylenically unsaturated moieties in conjugation with carbonyl moieties are disclosed. The compositions are depositable on substrates to form films. The films are amenable to oxidative and aminoplast cures and cure with light color. The compositions are desirable for use in cationic electrodeposition.
    Type: Grant
    Filed: March 26, 1981
    Date of Patent: August 31, 1982
    Assignee: PPG Industries, Inc.
    Inventors: Stephen L. Buchwalter, Joseph F. Bosso, Roger M. Christenson