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)
  • Patent number: 10954206
    Abstract: 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: Grant
    Filed: March 27, 2017
    Date of Patent: March 23, 2021
    Assignee: KOLON INDUSTRIES, INC.
    Inventors: Jong Un Sung, Sang Youb Seong, Yu Sung Kim, Jun Hyo Park
  • Patent number: 10081737
    Abstract: 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: Grant
    Filed: May 17, 2017
    Date of Patent: September 25, 2018
    Assignee: SHANGHAI YAO HE BIOCHEMICAL TECHNOLOGY CO., LTD.
    Inventor: Shun-Ming Hung
  • Patent number: 9303003
    Abstract: 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: Grant
    Filed: March 11, 2014
    Date of Patent: April 5, 2016
    Assignee: MITSUBISHI RAYON CO., LTD.
    Inventors: Naoshi Murata, Hiroyuki Mori
  • Patent number: 8981127
    Abstract: 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: Grant
    Filed: September 22, 2009
    Date of Patent: March 17, 2015
    Assignee: Zach System
    Inventors: Yvon Derrien, Eric Chenard, Alain Burgos
  • Patent number: 8829216
    Abstract: 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: Grant
    Filed: August 31, 2012
    Date of Patent: September 9, 2014
    Assignee: Biosynthetic Technologies, LLC
    Inventors: Jeremy Forest, Travis Thompson, Jakob Bredsguard
  • Patent number: 8802872
    Abstract: 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: Grant
    Filed: June 2, 2010
    Date of Patent: August 12, 2014
    Assignee: Momentive Specialty Chemicals Inc.
    Inventors: Jan Gouman, Sandra Rens-van der Lee, Robert van t Sand
  • Patent number: 8258326
    Abstract: 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: Grant
    Filed: March 2, 2012
    Date of Patent: September 4, 2012
    Assignee: LubriGreen Biosynthetics, LLC
    Inventors: Jeremy Forest, Jakob Bredsguard
  • Publication number: 20120095244
    Abstract: 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: Application
    Filed: June 2, 2010
    Publication date: April 19, 2012
    Inventors: Jan Gouman, Sandra Rens-van der Lee, Robert van t Sand
  • Patent number: 7459572
    Abstract: 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: Grant
    Filed: August 19, 2004
    Date of Patent: December 2, 2008
    Assignee: RSTECH Corporation
    Inventors: Seong-Jin Kim, Ho-Seong Lee, Jin-Won Yun, Ho-Cheol Kim
  • Patent number: 7176328
    Abstract: 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: Grant
    Filed: November 8, 2005
    Date of Patent: February 13, 2007
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Taiji Matsuzaki
  • Patent number: 7074946
    Abstract: 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: Grant
    Filed: December 1, 2004
    Date of Patent: July 11, 2006
    Assignee: Mitsubishi Gas Chemical Co., Ltd.
    Inventors: Takatoshi Shida, Syu Suzuki
  • Patent number: 6982349
    Abstract: 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: Grant
    Filed: November 5, 2003
    Date of Patent: January 3, 2006
    Assignee: Emcure Pharmaceuticals Limited
    Inventors: Satish Ramanlal Mehta, Baburao Manikroa Bhawal, Vishnu Hari Deshpande, Mukund Keshav Gurjar
  • Patent number: 6265531
    Abstract: 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: Grant
    Filed: May 20, 1998
    Date of Patent: July 24, 2001
    Assignee: Shell Oil Company
    Inventors: Johannes Adrianus Van Doorn, Jozef Jacobus Titus Smits
  • Patent number: 5892065
    Abstract: 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: Grant
    Filed: July 14, 1997
    Date of Patent: April 6, 1999
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Suketoshi Tsukamoto, Takami Ono, Hisao Ikeda, Motohiko Hidaka
  • Patent number: 5750739
    Abstract: 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 pha
    Type: Grant
    Filed: August 7, 1996
    Date of Patent: May 12, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tsuyoshi Isozaki, Masahiro Kurokawa, Akihiro Honma
  • Patent number: 5589554
    Abstract: 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: Grant
    Filed: September 16, 1994
    Date of Patent: December 31, 1996
    Assignee: Three Bond Co., Ltd.
    Inventor: Soichiro Hiraoka
  • Patent number: 5576399
    Abstract: 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: Grant
    Filed: June 28, 1994
    Date of Patent: November 19, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Roth, Roger Salvin, Kurt Meier, Bernhard Sailer, Rolf Wiesendanger
  • Patent number: 5466764
    Abstract: 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: Grant
    Filed: September 16, 1994
    Date of Patent: November 14, 1995
    Assignee: Three Bond Co., Ltd.
    Inventor: Soichiro Hiraoka
  • Patent number: 5380884
    Abstract: 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: Grant
    Filed: April 11, 1994
    Date of Patent: January 10, 1995
    Assignee: Osaka Organic Chemical Ind. Co., Ltd.
    Inventors: Hideo Hosokawa, Misao Shikatsu, Takahiro Fujimoto
  • Patent number: 5245057
    Abstract: 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: Grant
    Filed: November 4, 1992
    Date of Patent: September 14, 1993
    Assignee: The Dow Chemical Company
    Inventor: Robert P. Shirtum
  • Patent number: 5242996
    Abstract: 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: Grant
    Filed: May 22, 1991
    Date of Patent: September 7, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
  • Patent number: 5207874
    Abstract: 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: Grant
    Filed: June 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Atochem
    Inventors: Raymond Hess, Christian Lacroix
  • Patent number: 5183539
    Abstract: 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: Grant
    Filed: November 15, 1991
    Date of Patent: February 2, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akihiro Honma, Masahiro Kurokawa
  • Patent number: 5028686
    Abstract: 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: Grant
    Filed: September 18, 1990
    Date of Patent: July 2, 1991
    Assignee: The Dow Chemical Company
    Inventors: Zeng-Kun Liao, Chun S. Wang
  • Patent number: 4924013
    Abstract: 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: Grant
    Filed: July 22, 1988
    Date of Patent: May 8, 1990
    Assignee: Hi-Tek Polymers, Inc.
    Inventor: Joe M. Hunter
  • Patent number: 4877857
    Abstract: 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: Grant
    Filed: January 11, 1989
    Date of Patent: October 31, 1989
    Assignee: The Dow Chemical Company
    Inventors: Robert P. Shirtum, Elaine B. Darby
  • Patent number: 4831101
    Abstract: 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: Grant
    Filed: September 24, 1987
    Date of Patent: May 16, 1989
    Assignee: Rutgerswerke AG
    Inventors: Karl Jellinek, Bert Meier, Rolf Herzog, Gunter Reinsch
  • Patent number: 4810808
    Abstract: 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: Grant
    Filed: July 27, 1987
    Date of Patent: March 7, 1989
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Haruo Tomita, Kazuya Yonezawa
  • Patent number: 4778863
    Abstract: 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: Grant
    Filed: August 13, 1987
    Date of Patent: October 18, 1988
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Zeng-kun Liao
  • Patent number: 4755262
    Abstract: 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: Grant
    Filed: October 26, 1987
    Date of Patent: July 5, 1988
    Assignee: Osaka Yuki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Mitsumasa Matsunaga, Yukio Tanaka, Akio Tani, Shigeaki Matsumoto
  • Patent number: 4540802
    Abstract: 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: Grant
    Filed: May 3, 1983
    Date of Patent: September 10, 1985
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Haruo Tomita, Kazuya Yonezawa
  • 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