Glycidyl Ester Formed By Bonding The Oxy Of A -coo- Group Directly To An Acyclic Carbon Which Is Bonded Directly To An Oxirane Ring Patents (Class 549/515)
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Patent number: 10954206Abstract: The present invention relates to a method for preparing a glycidyl ester compound which comprises performing a reaction under reduced pressure without using a reaction solvent.Type: GrantFiled: March 27, 2017Date of Patent: March 23, 2021Assignee: KOLON INDUSTRIES, INC.Inventors: Jong Un Sung, Sang Youb Seong, Yu Sung Kim, Jun Hyo Park
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Patent number: 10081737Abstract: The curing agent for coatings includes at least 1,3,5-triglycidyl benzenetricarboxylate and 1,3,5-diglycidyl benzenetricarboxylate. To produce the curing agent, 1,3,5-benzenetricarboxylic acid reacts with a base and chloropropene to produce triallyl benzene-1,3,5-tricarboxylate. Then the triallyl benzene-1,3,5-tricarboxylate reacts with a surfactant, hydrogen peroxide and a catalyst to produce 1,3,5-triglycidyl benzenetricarboxylate and/or 1,3,5-diglycidyl benzenetricarboxylate. The 1,3,5-triglycidyl benzenetricarboxylate can be applied to coatings as a curing agent.Type: GrantFiled: May 17, 2017Date of Patent: September 25, 2018Assignee: SHANGHAI YAO HE BIOCHEMICAL TECHNOLOGY CO., LTD.Inventor: Shun-Ming Hung
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Patent number: 9303003Abstract: Provided is glycidyl(meth)acrylate which is reduced in the content of impurities including chlorine. This process comprises reacting epichlorohydrin with an alkali metal (meth)acrylate in the presence of a catalyst to produce glycidyl(meth)acrylate, the process including a step in which the reaction is conducted while making a Bronsted acid present in the reaction system in an amount of 0.0001-0.08 mol per mol of the alkali metal (meth)acrylate.Type: GrantFiled: March 11, 2014Date of Patent: April 5, 2016Assignee: MITSUBISHI RAYON CO., LTD.Inventors: Naoshi Murata, Hiroyuki Mori
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Patent number: 8981127Abstract: The present invention relates to a process for the preparation of nebivolol and, more particularly, to an improved process of synthesizing an alpha-haloketone of formula a key intermediate in the preparation of nebivolol.Type: GrantFiled: September 22, 2009Date of Patent: March 17, 2015Assignee: Zach SystemInventors: Yvon Derrien, Eric Chenard, Alain Burgos
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Patent number: 8829216Abstract: Provided herein are poly-capped estolides, including those of the Formula IV in which n is an integer equal to or greater than 0; m is an integer equal to or greater than 2; R1 is selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R3 and R4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched. Hydroxy estolides are also described herein, which may be suitable end products, or serve as intermediates to provide poly-capped estolides. Also provided are compositions containing poly-capped estolides and methods of making both said poly-capped estolides and compositions thereof.Type: GrantFiled: August 31, 2012Date of Patent: September 9, 2014Assignee: Biosynthetic Technologies, LLCInventors: Jeremy Forest, Travis Thompson, Jakob Bredsguard
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Patent number: 8802872Abstract: Accordingly, the invention relates to a process for the preparation of a glycidyl ester of a branched monocarboxylic acid by reacting an aliphatic monocarboxylic acid of the formula R1R2R3CCOOH, wherein R1, R2, and R3 each independently represent an alkyl radical of normal or branched structure containing from 1 to 20 carbon atoms and an epoxyalkyl halide containing from 3 to 13 carbon atoms in the presence of a catalyst, wherein a greater than stoichiometric amount of epoxyalkyl halide is reacted with the acid (e.g., preferably in the molar ratio of epoxyalkyl halide to acid that is in the range of from 1.02:1 to 1.50:1) to form an intermediate reaction product comprising a halohydrin, the epoxyalkyl halide is added to the acid with appropriate cooling of the reactants and/or the reaction mixture to keep the temperature of the reaction mixture below 80° C., whereupon the epoxyalkyl halide and the acid are reacted at a temperature below 80° C. (preferably in the range of from 55 to 75° C.Type: GrantFiled: June 2, 2010Date of Patent: August 12, 2014Assignee: Momentive Specialty Chemicals Inc.Inventors: Jan Gouman, Sandra Rens-van der Lee, Robert van t Sand
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Patent number: 8258326Abstract: Provided herein are compounds of the formula: in which n is an integer equal to or greater than 1; m is an integer equal to or greater than 1; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R1, R3, and R4, independently for each occurrence, are selected from optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched, wherein at least one of R1, R2, R3, or R4 is sulfurized or epoxidized. Also provided are compositions containing the compounds and methods of making both the compounds and compositions thereof.Type: GrantFiled: March 2, 2012Date of Patent: September 4, 2012Assignee: LubriGreen Biosynthetics, LLCInventors: Jeremy Forest, Jakob Bredsguard
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Publication number: 20120095244Abstract: Accordingly, the invention relates to a process for the preparation of a glycidyl ester of a branched monocarboxylic acid by reacting an aliphatic monocarboxylic acid of the formula R1R2R3COOH, wherein R1, R2, and R3 each independently represent an alkyl radical of normal or branched structure containing from 1 to 20 carbon atoms and an epoxyalkyl halide containing from 3 to 13 carbon atoms in the presence of a catalyst, wherein a greater than stoichiometric amount of epoxyalkyl halide is reacted with the acid (e.g., preferably in the molar ratio of epoxyalkyl halide to acid that is in the range of from 1.02:1 to 1.50:1) to form an intermediate reaction product comprising a halohydrin, the epoxyalkyl halide is added to the acid with appropriate cooling of the reactants and/or the reaction mixture to keep the temperature of the reaction mixture below 80° C., whereupon the epoxyalkyl halide and the acid are reacted at a temperature below 80° C. (preferably in the range of from 55 to 75° C.Type: ApplicationFiled: June 2, 2010Publication date: April 19, 2012Inventors: Jan Gouman, Sandra Rens-van der Lee, Robert van t Sand
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Patent number: 7459572Abstract: There is provided a process for preparing a glycidyl derivative from 3-chloro-1,2-propanediol, comprising i) adding a phosphate salt to a solution into which 3-chloro-1,2-propanediol is dissolved into a solvent to produce glycidol, and ii) adding to the solution of step i) a base capable of releasing a glycidyl group from the glycidol and a substrate susceptible to nucleophilic attack to produce the desired glycidyl derivative by nucleophilic attack of the glycidyl group to the substrate.Type: GrantFiled: August 19, 2004Date of Patent: December 2, 2008Assignee: RSTECH CorporationInventors: Seong-Jin Kim, Ho-Seong Lee, Jin-Won Yun, Ho-Cheol Kim
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Patent number: 7176328Abstract: In the production of glycidyl methacrylate from an alkali metal salt of methacrylic acid and epichlorohydrin, at least one water-soluble polymerization inhibitor is added at an appropriate stage of the production. The addition of the water-soluble polymerization inhibitor prevents the formation of insoluble solid matters to increase the efficiency of phase separation in the washing operation for removing a by-produced salt and form a clear interface between the phases, thereby minimizing the recovery loss. In addition, the troubles such as clogging of pipe lines of production apparatus and equipment for waster water treatment can be avoided.Type: GrantFiled: November 8, 2005Date of Patent: February 13, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Taiji Matsuzaki
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Patent number: 7074946Abstract: A method of stably producing glycidyl 2-hydroxyisobutyrate at high purity and high yield is provided. A reactive diluent is provided for an epoxy resin including the above-mentioned glycidyl 2-hydroxyisobutyrate, and an epoxy resin composition.Type: GrantFiled: December 1, 2004Date of Patent: July 11, 2006Assignee: Mitsubishi Gas Chemical Co., Ltd.Inventors: Takatoshi Shida, Syu Suzuki
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Patent number: 6982349Abstract: The present invention relates to an improved process for producing optically active (S)-atenolol of formula (1) in high optical purity by reacting a phenol with an epichlorohydrin.Type: GrantFiled: November 5, 2003Date of Patent: January 3, 2006Assignee: Emcure Pharmaceuticals LimitedInventors: Satish Ramanlal Mehta, Baburao Manikroa Bhawal, Vishnu Hari Deshpande, Mukund Keshav Gurjar
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Patent number: 6265531Abstract: A glycidylester of the general formula I in which R1 and R4 are the same or different C1-C6 alkyl or C6-C10 cycloalkyl groups, and R2 and R3 are the same or different and are H or C1-C6 alkyl or C6-C10 cycloalkyl groups. The glycidylester is used in a thermosetting resin composition, comprising also a curing compound and preferably an advanced resin product. The thermosetting resin composition can be applied for outdoor durable coatings, having excellent resistance against acid rain.Type: GrantFiled: May 20, 1998Date of Patent: July 24, 2001Assignee: Shell Oil CompanyInventors: Johannes Adrianus Van Doorn, Jozef Jacobus Titus Smits
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Patent number: 5892065Abstract: A 2,3-epoxypropyl derivative or a 2-methyl-2,3-epoxypropyl derivative of a compound having carboxyl groups or amido groups is produced as a purified product having an epoxide equivalent of 1.0 to 1.1 times the theoretical epoxide equivalent of the derivative, an ionic halogen content of 10 ppm or less, transparency when molten and a stability against increase in the epoxide equivalent when stored at 150.degree. C. for 24 hours, by a process comprising steps (A) reacting 1.Type: GrantFiled: July 14, 1997Date of Patent: April 6, 1999Assignee: Nissan Chemical Industries, Ltd.Inventors: Suketoshi Tsukamoto, Takami Ono, Hisao Ikeda, Motohiko Hidaka
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Patent number: 5750739Abstract: There is disclosed a process for producing a glycidyl ester of acrylic acid or methacrylic acid which comprises the steps of neutralizing acrylic acid or methacrylic acid with a carbonate or a bicarbonate of an alkali metal in an excess amount of epichlorohydrin while an oxygen-containing gas is blown into the liquid reaction system; subjecting water formed by the neutralization and epichlorohydrin to azeotropic distillation to discharge them outside the reaction system and to form an alkali metal salt of acrylic acid or methacrylic acid; adding a quaternary ammonium salt as a catalyst to the reaction system to react the alkali metal salt of the acid with the epichlorohydrin and thus synthesize the glycidyl ester of the acid; cooling the liquid reaction product while recovering part of the excess epichlorohydrin under reduced pressure; adding aqueous solution of an alkali hydroxide to the liquid reaction product to separate into aqueous layer and organic layer; adding a catalyst deactivator to the organic phaType: GrantFiled: August 7, 1996Date of Patent: May 12, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tsuyoshi Isozaki, Masahiro Kurokawa, Akihiro Honma
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Patent number: 5589554Abstract: An adhesive composition is here disclosed which comprises a 2-cyanoacrylate and at least one of compounds (a) and (b):(a) an addition reaction product of an epoxy group and a compound having a cyano group and a carboxylic acid group in its molecule, and(b) a compound having a cyano group and a carboxylic acid group in its molecule. A process for preparing the adhesive composition is also disclosed herein. According to the present invention, the 2-cyanoacrylate-based adhesive composition can be obtained which is excellent in storage stability and hardening properties of thick films and which has a high hardening rate and remarkably improved surface hardening properties of the adhesive composition itself bulged from between adherends. Particularly, the 2-cyanoacrylate bulged from between the adherends can harden rapidly, so that the vaporization of the 2-cyanoacrylate can be minimized.Type: GrantFiled: September 16, 1994Date of Patent: December 31, 1996Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5576399Abstract: Novel epoxy acrylates and carboxyl group-containing epoxy acrylates of formulae II and III of the claims that are relatively highmolecular and are chemically crosslinkable can be used in photoresist formulations with the additional use of highly polymerized polymer binders. Such resist formulations are used in particular in the field of printed circuit boards and printing plates, are applicable from aqueous medium, are almost tack-free and have very good edge coverage, especially on conductors.Type: GrantFiled: June 28, 1994Date of Patent: November 19, 1996Assignee: Ciba-Geigy CorporationInventors: Martin Roth, Roger Salvin, Kurt Meier, Bernhard Sailer, Rolf Wiesendanger
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Patent number: 5466764Abstract: There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate. In particular, the adhesive strength of the 2-cyanoacrylate-based adhesive composition can be remarkably increased without lowering the hardening rate, and so the 2-cyanoacrylate-based adhesive composition can exert a sufficient resistance to impact and the like at the time of the adhesion of metals, rubbers, plastics and lumbers and the reliability of adherends can be improved.Type: GrantFiled: September 16, 1994Date of Patent: November 14, 1995Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5380884Abstract: Glycidyl methacrylate is produced by the reaction of an alkali metal salt of methacrylic acid with epichlorohydrin in the presence of a quaternary ammonium salt and a polymerization inhibitor in a reaction system where the water content is adjusted to 500 to 2000 ppm. Glycidyl methacrylate is purified by the method of the present invention, wherein the reaction mixture obtained by the above method is washed with a dilute aqueous solution of sodium hydroxide and heated under a reduced pressure to remove unchanged epichlorohydrin by distillation, after which steam is blown into the reaction system under the conditions of reduced pressure and heating to distill away the remaining epichlorohydrin together with glycidyl methacrylate as the first distillate fraction, followed by ceasing the steam blow and carrying out distillation under the conditions of reduced pressure and heating to obtain glycidyl methacrylate as the main distillate fraction.Type: GrantFiled: April 11, 1994Date of Patent: January 10, 1995Assignee: Osaka Organic Chemical Ind. Co., Ltd.Inventors: Hideo Hosokawa, Misao Shikatsu, Takahiro Fujimoto
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Patent number: 5245057Abstract: A continuous horizontal reactor system and process for employing such a system. In one embodiment, a reactor system having a cylindrical multi-compartment vessel, the compartments intercommunicating via a common overhead space or separated spaces from which vapor with reaction product or by-products may be removed, and from which liquid effluent with reaction products or by-products may be removed and reactants and catalyst flowable into each compartment and agitators in each compartment. Such a reactor system for producing liquid epoxy resins. Processes using such a reactor to produce reaction products, e.g. liquid epoxy resins.Type: GrantFiled: November 4, 1992Date of Patent: September 14, 1993Assignee: The Dow Chemical CompanyInventor: Robert P. Shirtum
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Patent number: 5242996Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.Type: GrantFiled: May 22, 1991Date of Patent: September 7, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
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Patent number: 5207874Abstract: The purification by distillation of glycidyl (meth)acrylate containing light products containing epichlorohydrin and light impurities, and heavy impurities comprises: in a first stage, a distillation of the glycidyl (meth)acrylate to be purified is conducted in the presence of a first solvent, e.g., water, capable of forming a low boiling point heteroazeotrope with the light impurities and epichlorohydrin, so as to obtain a head fraction which consists essentially of a solvent-light products heteroazeotrope; and, in a second stage, the glycidyl (meth)acrylate thus freed from the light products is subjected to a distillation in the presence of a second solvent, e.g.Type: GrantFiled: June 20, 1991Date of Patent: May 4, 1993Assignee: AtochemInventors: Raymond Hess, Christian Lacroix
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Patent number: 5183539Abstract: A method of purifying a crude glycidyl (meth)acrylate, by (1) subjecting a crude glycidyl (meth)acrylate containing epichlorohydrin and other chlorine compounds as impurities to a stripping treatment with a mixed gas containing oxygen gas in the presence of a quaternary ammonium salt, and then (2) distilling the treated product to obtain a purified glycidyl (meth)acrylate.Type: GrantFiled: November 15, 1991Date of Patent: February 2, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akihiro Honma, Masahiro Kurokawa
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Patent number: 5028686Abstract: Epoxy resins which are relatively low in total bound halide are prepared by concurrently and continuously adding a mixture of (1) a mixture of an epihalohydrin, a compound containing an average of more than one group reactive with a vicinal epoxide group and a solvent and (2) an aqueous or organic solution of an alkali or alkaline earth metal hydroxide; to (3) a mixture of epihalohydrin and a solvent.Type: GrantFiled: September 18, 1990Date of Patent: July 2, 1991Assignee: The Dow Chemical CompanyInventors: Zeng-Kun Liao, Chun S. Wang
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Patent number: 4924013Abstract: A process for the reduction of free epichlorohydrin in epoxy compounds which involves the treatment of an epoxy compound with an alkali metal sulfite, preferably sodium sulfite.Type: GrantFiled: July 22, 1988Date of Patent: May 8, 1990Assignee: Hi-Tek Polymers, Inc.Inventor: Joe M. Hunter
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Patent number: 4877857Abstract: The construction costs of a process for preparing epoxy compounds from aromatic compounds containing an active hydrogen atom reactive with an epihalohydrin by reacting such compounds with an epihalohydrin in the presence of an alkali metal hydroxide while controlling the water content in the reaction mixture and subsequently removing the alkali metal halide salt from the reaction mixture is made less costly by employing a water extraction means to remove the alkali metal halide salts from the reaction product mixture containing the epoxy product.Type: GrantFiled: January 11, 1989Date of Patent: October 31, 1989Assignee: The Dow Chemical CompanyInventors: Robert P. Shirtum, Elaine B. Darby
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Patent number: 4831101Abstract: A process for the preparation of at least one member of the group consisting of monoglycidyl and polyglycidyl compounds comprising reacting a member of the group consisting of mono- and polyvalent phenols, aromatic amines and aromatic carboxylic acids with an epihalohydrin substantially free of halogenated hydrocarbons.Type: GrantFiled: September 24, 1987Date of Patent: May 16, 1989Assignee: Rutgerswerke AGInventors: Karl Jellinek, Bert Meier, Rolf Herzog, Gunter Reinsch
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Patent number: 4810808Abstract: A process for preparing a polyglycidyl compound in which an aromatic hydroxycarboxylic acid having phenolic hydroxyl group is reacted with an epihalohydrin in the presence of a phase transfer catalyst and the dehydrohalogenation is then conducted by acting an aqueous alkali solution on the reaction mixture obtained in the first step.Type: GrantFiled: July 27, 1987Date of Patent: March 7, 1989Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Haruo Tomita, Kazuya Yonezawa
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Patent number: 4778863Abstract: Glycidyl derivatives of compounds containing --OH, --NH.sub.2 and/or --COOH groups are prepared by reacting in the presence of a mixture of solvents, at least one of which is a polar aprotic solvent, an excess of an epihalohydrin with a compound containing --OH, --NH.sub.2 and/or --COOH groups while continuously or incrementally adding an alkali metal hydroxide to the mixture and removing water from the reaction by codistillation with epihalohydrin and the solvents.Type: GrantFiled: August 13, 1987Date of Patent: October 18, 1988Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Zeng-kun Liao
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Patent number: 4755262Abstract: This invention relates to a method for the purification of glycidyl acrylate or glycidyl methacrylate. Specifically, the invention effects the purification by using a residual catalyst-inactivating additive and consequently produces highly purified glycidyl acrylate or glycidyl methacrylate containing substantially no epichlorohydrin and having a low chlorine content.Type: GrantFiled: October 26, 1987Date of Patent: July 5, 1988Assignee: Osaka Yuki Kagaku Kogyo Kabushiki KaishaInventors: Mitsumasa Matsunaga, Yukio Tanaka, Akio Tani, Shigeaki Matsumoto
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Patent number: 4540802Abstract: An epoxy resin of the general formula: ##STR1## wherein X.sub.1 and X.sub.2 are --OH or ##STR2## and X.sub.3 is --OH, ##STR3## or a group of the general formula: ##STR4## in which X.sub.4, X.sub.5 and X.sub.6 are --OH or ##STR5## provided that at least one of X.sub.1 to X.sub.6 is ##STR6## The epoxy resin is prepared by reacting gallic acid or tannic acid with an epihalohydrin in the presence of a phase transfer catalyst and reacting the obtained reaction mixture with an aqueous alkali solution.Type: GrantFiled: May 3, 1983Date of Patent: September 10, 1985Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Haruo Tomita, Kazuya Yonezawa
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Patent number: 4465815Abstract: 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: GrantFiled: December 28, 1981Date of Patent: August 14, 1984Assignee: Ford Motor CompanyInventor: Mohinder S. Chattha