With Preservative Or Stabilizer Patents (Class 568/421)
  • Patent number: 9029606
    Abstract: A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.
    Type: Grant
    Filed: June 27, 2012
    Date of Patent: May 12, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
  • Publication number: 20140187822
    Abstract: A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.
    Type: Application
    Filed: June 27, 2012
    Publication date: July 3, 2014
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masashi Takimoto, Tomonori Yamaoka, Yoshio Onogawa
  • Patent number: 8278332
    Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from retinoid compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of retinoid compounds in a composition by at least 3-fold.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: October 2, 2012
    Assignee: Hallstar Innovations Corp.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 8263051
    Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from resveratrol compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of resveratrol compounds in a composition by at least 3-fold and as much as 10-fold or greater. The ability of the alkoxycrylene compounds to stabilize the resveratrol compound is concentration dependent, with the amount of resveratrol photostabilization increasing with the concentration of the alkoxycrylene compound.
    Type: Grant
    Filed: April 5, 2011
    Date of Patent: September 11, 2012
    Assignee: Hallstar Innovations Corp.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Publication number: 20110251242
    Abstract: The photostabilizing electronic excited state energy—particularly singlet state energy from resveratrol compounds—has been found to be readily transferred to (accepted by) ?-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, preferably C1-C8, more preferably methoxy, and the non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, preferably C2-C20. The alkoxycrylene compounds of formula (I) significantly increase the photostability of resveratrol compounds in a composition by at least 3-fold and as much as 10-fold or greater. The ability of the alkoxycrylene compounds to stabilize the resveratrol compound is concentration dependent, with the amount of resveratrol photostabilization increasing with the concentration of the alkoxycrylene compound.
    Type: Application
    Filed: April 5, 2011
    Publication date: October 13, 2011
    Applicant: HALLSTAR INNOVATIONS CORP.
    Inventors: Craig A. Bonda, Anna Pavlovic, Jean Zhang
  • Patent number: 6818587
    Abstract: The invention relates to double-metal cyanide (DMC) catalysts for preparing polyether polyols by the polyaddition of alkylene oxides on to starter compounds containing active hydrogen atoms, wherein the DMC catalysts are composed of: a) at least one DMC compound; b) at least one organic complexing ligand which is not a cyclic polyol; and c) at least one cyclic polyol. The DMC catalysts of the present invention have increased activity compared to known catalyst.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: November 16, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Schäfer, Jörg Hofmann, Pieter Ooms
  • Patent number: 6803356
    Abstract: A method for the preparation of polymers derived from acrolein and including poly(2-propenal, 2-propenoic acid), characterised in that the polymers are exposed to the presence of water, whereby such polymers exhibit increased antimicrobial activity. The polymers may be heated in the range of 40 to 150° C. Further, the polymers may be prepared in the presence of polyethylene glycols, polyols and/or alkanols.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: October 12, 2004
    Assignee: Chemeq Ltd.
    Inventors: Graham John Hamilton Melrose, Gerry Daly, Andrew James Huxham
  • Patent number: 6624330
    Abstract: The present invention relates to a method for stabilizing phenylacetaldehyde by adding at least one additive, in which case the additive contains one or more polybasic carboxylic acids.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: September 23, 2003
    Assignee: Haarmann & Reimer GmbH
    Inventor: Walter Kuhn
  • Publication number: 20020128518
    Abstract: The present invention relates to a method for stabilizing phenylacetaldehyde by adding at least one additive, in which case the additive contains one or more polybasic carboxylic acids.
    Type: Application
    Filed: December 4, 2001
    Publication date: September 12, 2002
    Inventor: Walter Kuhn
  • Patent number: 6150563
    Abstract: Aliphatic alkanals with a water content of greater than 300 ppm which are stable in storage, and a method of improving the storage stability of these aliphatic alkanals, especially of substituted, sulfur-containing alkanals. The formation of oligomers, polymers and condensation products from elimination reactions and oxidation and the subsequent reactions of the products formed results in undesired impurities that are largely prevented by the addition of an organic acid that forms metal complexes and, optionally, alkanolamines or trialkanolamines.
    Type: Grant
    Filed: August 14, 1998
    Date of Patent: November 21, 2000
    Assignee: Degussa-Huls AG
    Inventors: Hans Joachim Hasselbach, Klaus Huthmacher, Katja Kelm, Horst Weigel
  • Patent number: 6137013
    Abstract: A method of stabilizing aliphatic C.sub.3 -C.sub.14 -aldehydes against polymerization and autocondensation by the addition of alkaline substances to the aldehydes wherein the alkaline substances used are alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates or alkali metal carboxylates which are added to the aldehyde to be stabilized in amounts of 0.05-20 ppm, based on the aldehyde.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: October 24, 2000
    Assignee: Celanese GmbH
    Inventors: Michael Riedel, Wolfgang Zgorzelski, Michael Messerschmidt, Klaus Bergrath
  • Patent number: 5917094
    Abstract: Acrolein-releasing emulsion homopolymers release acrolein in aqueous systems. They are produced by adding acrolein, at least 95% by weight pure, to a solution of an alkali hydroxide, with the temperature not exceeding 25.degree. C. during the addition, and then adjusting the pH to 5 to 7 by adding a mineral acid.
    Type: Grant
    Filed: December 16, 1997
    Date of Patent: June 29, 1999
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Peter Werle, Hans Peter Krimmer, Martin Trageser
  • Patent number: 5912389
    Abstract: A stabilizer for an aqueous aliphatic aldehyde solution comprising acetic acid, a halogenated acetic acid or a compound capable of releasing acetic acid or a halogenated acetic acid in water.
    Type: Grant
    Filed: October 14, 1997
    Date of Patent: June 15, 1999
    Assignee: Katayama Chemical, Inc.
    Inventor: Shinichi Matsumoto
  • Patent number: 5874631
    Abstract: A method for increasing the shelf life of liquid hydroxy- and alkoxyalkyl ketones by adding from 0.0001 to 1% by weight of a base is described.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: February 23, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl-Heinz Ross, Ludwig Wambach, Harro Wache
  • Patent number: 5723498
    Abstract: A composition which is capable of releasing acrolein and is easy to handle contains (i) an acetal of acrolein with a C.sub.1-6 alcohol with 1 to 4 hydroxyl groups and (ii) an acid soluble therein and chemically compatible with a pK.sub.s value of less than 4 and (iii) is anhydrous. A preferred composition contains 2-vinyl-1,3-dioxolane as acetal, anhydrous oxalic acid, fumaric acid or maleic acid or a mixture of mono- and di(C.sub.1 - to C.sub.3 -)alkyl phosphate as acid and, in addition, a non-ionic surfactant. The acrolein is released at the site of use upon contact with for example water for the purpose of combatting microbial, vegetable and animal pests.
    Type: Grant
    Filed: September 13, 1995
    Date of Patent: March 3, 1998
    Assignee: Degussa Aktiengellschaft
    Inventors: Peter Werle, Martin Trageser, Oswald Helmling, Harold Jakob
  • Patent number: 5364969
    Abstract: A novel and very effective method is proposed for the stabilization of a higher aliphatic compound having at least one double bond in a molecule such as the sex pheromone compounds of agricultural pest insects used for the elimination of the pest insect by the method of mating disruption. The method comprises admixing the sex pheromone compound with each a specified amount of (a) a specific phenolic compound, e.g., tert-butyl hydroquinone, di-tert-butyl hydroquinone, di-tert-amyl hydroquinone, di-tert-butyl p-cresol, methyl hydroquinone and p-methoxy phenol, as an antioxidant and (b) 2-(2'-hydroxy-3'-tert-butyl-5'-methyl phenyl)-5-chloro benzotriazole in combination.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: November 15, 1994
    Assignee: Shiu-Etsu Chemical Co., Ltd.
    Inventors: Toyohisa Sakurada, Hiroshi Suzuki, Ryuichi Saguchi
  • Patent number: 5352841
    Abstract: Liquid acrolein, whose hazardous properties make handling difficult, is used to dose aqueous systems with acrolein in a biocidally effective concentration. Disclosed are agents which increase the ease and safety of acrolein handling and which are characterized by a content of 30 to 95% by weight acrolein and 5 to 70% by weight inorganic carrier materials. Silicas are the preferred carrier materials. The powdery or highly viscous mixture of substances will preferably exist in molded form and is additionally provided with a cladding that is impermeable to acrolein vapor. In dosing the aqueous systems, the agents are introduced directly in the water whereupon the acrolein is released.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: October 4, 1994
    Assignee: Degussa Aktiengesellschaft
    Inventors: Peter Werle, Werner Pahling, Martin Trageser
  • Patent number: 5183944
    Abstract: Aqueous solutions can be doped in a simple, safe and economic manner with acrolein in biocidally effective concentration by converting acrolein acetals in aqueous phase in the presence of a strongly acidic deacetalation catalyst into acrolein, cleaving the alcohol component, constantly removing the formed acrolein from the decetalation mixture and transferring it by means of an inert gas stream or a liquid jet pump with the aqueous solution to be doped as jet fluid into the aqueous solution to be doped.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: February 2, 1993
    Assignee: Degussa AG
    Inventors: Peter Werle, Martin Trageser, Hermann Piana
  • Patent number: 5103053
    Abstract: A tert-amine which contains an acid-activated color body precursor is treated to prevent it or a derivative thereof, e.g., an amine oxide, betaine, or quaternary ammonium compound, from turning pink when exposed to acidic conditions by contacting it with a dialkylacetal.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: April 7, 1992
    Assignee: Ethyl Corporation
    Inventors: Joe D. Sauer, Kim R. Smith, James E. Borland
  • Patent number: 4599456
    Abstract: Novel compositions are disclosed consisting essentially of aldehydes of the structure R--CHO (wherein R is a C.sub.8 -C.sub.30 carbon radical) and about 0.1 to about 5 parts by weight of a triarylphosphine per 100 parts of aldehyde. In addition, a process for the recovery of essentially pure high boiling aldehyde by fractional distillation is provided wherein about 0.1 to about 5 parts by weight of a triarylphosphine per 100 parts of high boiling aldehyde is added to the aldehyde prior to distillation. Further, process for improving the high temperature storage stability of high boiling aldehydes is provided, which comprises adding about 0.1 to about 5 parts by weight of a triarylphosphine per 100 parts high boiling aldehyde to the aldehyde.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4568771
    Abstract: Aliphatic higher aldehyde compounds, e.g. Z-11-hexadecenal and Z-9-tetradecenal, can be stabilized against oxidation to form a carboxylic acid and trimer formation by the addition of a stabilizer compound including a tertiary amine compound, benzophenone compound, salicylate compound, benzotriazole compound and cyanoacrylate compound together with or without further admixture of an antioxidant.
    Type: Grant
    Filed: January 13, 1984
    Date of Patent: February 4, 1986
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshinobu Ishihara, Akira Yamamoto, Mitsuyoshi Ohshima, Nobolu Aiba
  • Patent number: 4546205
    Abstract: An amino/phenolic composition effective for enhancing the storage stability of aldehydes, particularly sulfur-containing aliphatic aldehydes of low molecular weight, i.e., those containing from 3 to 10 carbon atoms.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: October 8, 1985
    Assignee: Pennwalt Corporation
    Inventor: Stanley R. Sandler
  • Patent number: 4526998
    Abstract: Deodorized formalin produced by mixing formalin with additives comprising methyl salicylate and ethanol or methanol. A desired mixing ratio of these components is required.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: July 2, 1985
    Inventor: Naoyuki Takeuchi
  • Patent number: 4491676
    Abstract: Described herein is a process for rapidly obtaining a stable freeze point depressed aqueous solution comprising a dialdehyde and an aliphatic monohydroxyl alcohol and/or polyhydroxyl alcohol by adding thereto a catalytic amount of a strong acid. Also included herein is a method for liberating the dialdehyde in the aqueous solution by dilution with water and the addition of a catalytic amount of a strong acid.
    Type: Grant
    Filed: June 28, 1983
    Date of Patent: January 1, 1985
    Assignee: Union Carbide Corporation
    Inventors: Robert G. Eagar, Jr., Gerald J. Murphy
  • Patent number: 4448977
    Abstract: A storage stable composition of glutaraldehyde acetals and an organic acidic catalyst, which can be converted to glutaraldehyde at the site and upon demand, by the addition of water.
    Type: Grant
    Filed: August 26, 1982
    Date of Patent: May 15, 1984
    Assignee: Union Carbide Corporation
    Inventors: Glenn H. Warner, Louis F. Theiling, Jr., Marvin G. Freid
  • Patent number: 4414419
    Abstract: Aldehydes having 3 to 14 carbon atoms are stabilized against polymerization and autocondensation by the addition thereto of triethanolamine or dimethylethanolamine in an amount at least 10 ppm (based on the amount of aldehyde) and preferably 20 to 100 ppm.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: November 8, 1983
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Volker Falk, Claus Kniep
  • Patent number: 4335002
    Abstract: Described are cis-3-hexenyl derivatives having the generic structure: ##STR1## wherein R is one of the moieties: ##STR2## which are useful in foodstuffs, flavorings, fragrances, perfumed articles (e.g. anionic, cationic or nonionic detergents, dryer-added fabric softener articles and cosmetic powders) and smoking tobacco flavorings; processes for producing such cis-3-hexenyl derivatives and products produced according to such processes which include chemical compounds in addition to said cis-3-hexenyl derivatives.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: June 15, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Granda, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4320231
    Abstract: Described herein is an aqueous solution comprising a dialdehyde of from 2 to 6 carbon atoms and an aliphatic ketone. This solution may be stored under conditions under which the aqueous dialdehyde solution would normally freeze.
    Type: Grant
    Filed: November 20, 1980
    Date of Patent: March 16, 1982
    Assignee: Union Carbide Corporation
    Inventor: Gerald J. Murphy
  • Patent number: 4312766
    Abstract: Described are cis-3-hexenyl derivatives having the generic structure: ##STR1## wherein R is one of the moieties: ##STR2## which are useful in foodstuffs, flavorings, fragrances, perfumed articles (e.g. anionic, cationic or nonionic detergents, dryer-added fabric softener articles and cosmetic powders) and smoking tobacco flavorings; processes for producing such cis-3-hexenyl derivatives and products produced according to such processes which include chemical compounds in addition to said cis-3-hexenyl derivatives.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: January 26, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Granda, Joaquin F. Vinals, Jacob Kiwala
  • Patent number: 4289912
    Abstract: The tendency of liquid paraformaldehyde containing water and paraformaldehyde in, for example, approximately 80% to approximately 90% concentration to precipitate solid paraformaldehyde therefrom is retarded by the incorporation thereinto of an effective amount of a moderator or stabilizer selected from the group consisting of polyacrylic acid, tartaric acid, dl-malic acid, ethylenediaminetetraacetic acid, and citric acid. The prior-art stabilizers known and used for lower-concentration formaldehyde solutions of, for example, about 50% strength are not effective. Conversely, the present moderators are not effective in the lower-concentration solutions.
    Type: Grant
    Filed: May 2, 1980
    Date of Patent: September 15, 1981
    Assignee: Celanese Corporation
    Inventors: Marvin E. Harris, Jr., Hubert H. Thigpen
  • Patent number: 4244876
    Abstract: A storage stable composition of glutaraldehyde acetals and an organic acidic catalyst, which can be converted to glutaraldehyde at the site and upon demand, by the addition of water.
    Type: Grant
    Filed: November 17, 1978
    Date of Patent: January 13, 1981
    Assignee: Union Carbide Corporation
    Inventors: Glenn H. Warner, Louis F. Theiling, Marvin G. Freid
  • Patent number: 4241098
    Abstract: Described is a method for augmenting or enhancing the aroma or flavor of a foodstuff comprising adding to the foodstuff from 0.05 up to about 500 parts per million of a mixture of cis-3-hexenal, trans-2-hexenal, cis-3-hexenyl formate, cis-3-hexenol and cis-3-hexenyl-cis-3-hexenoate prepared by the process of reacting cis-3-hexenol with pyridinium chlorochromate.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: December 23, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Granda, Joaquin F. Vinals, Jacob Kiwala