Exactly One Azo Group Containing Or Azo Attached Indirectly To An Additional Azo Group By Ionic Bonding Patents (Class 534/838)
  • Publication number: 20140221632
    Abstract: The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.
    Type: Application
    Filed: April 7, 2014
    Publication date: August 7, 2014
    Inventors: Chun-Hsu LIN, Chian-Yi SUN, Yung-Yu YIN, Chun-Shih LI, Yo-Chun CHOU
  • Publication number: 20140011986
    Abstract: The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.
    Type: Application
    Filed: September 21, 2012
    Publication date: January 9, 2014
    Inventors: Chun-Hsu LIN, Chien-Yi SUN, Yung-Yu YIN, Chun-Shih LI, Yo-Chun CHOU
  • Patent number: 8592565
    Abstract: The invention relates to carbon surfaces modified with one or more azide groups. The invention also relates to methods of modifying carbon surfaces with one or more azide groups.
    Type: Grant
    Filed: January 10, 2008
    Date of Patent: November 26, 2013
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Christopher E. D. Chidsey, Anando Devadoss, Neal K. Devaraj
  • Publication number: 20130289174
    Abstract: A pigment preparation is provided, said preparation comprises an organic pigment comprising a chromophore Q1 and a derivative thereof comprising specific organic substituents via an aliphatic carbon atom in an amount of from 0.1 to 30 mol, based on 100 mol of the organic pigment as well as a process for its preparation and to its use in coloring an organic material such as plastics, coatings or inks.
    Type: Application
    Filed: December 15, 2011
    Publication date: October 31, 2013
    Applicant: BASF SE
    Inventors: Philippe Bugnon, Peter Nesvadba
  • Publication number: 20130244267
    Abstract: The present disclosure features a strain-promoted [2+2+2] reaction that can be carried out under physiological conditions. In general, the reaction involves reacting a pi-electrophile with a low lying LUMO with a quadricyclane on a biomolecule, generating a covalently modified biomolecule. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo and in vitro. The reaction is compatible with modification of living cells. In certain embodiments, the pi-electrophile can comprise a molecule of interest that is desired for delivery to a quadricyclane-containing biomolecule via [2+2+2] reaction.
    Type: Application
    Filed: September 6, 2012
    Publication date: September 19, 2013
    Inventors: Ellen May Sletten, Carolyn Ruth Bertozzi
  • Patent number: 7812141
    Abstract: The present invention relates to novel dyestuffs of formula (I) wherein the substituents have the meanings defined in the claims, the production of such dyestuffs, the use of these dyestuffs and material dyed or printed by such dyestuffs.
    Type: Grant
    Filed: December 12, 2005
    Date of Patent: October 12, 2010
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Robert Egli, Thomas Grabenstein
  • Patent number: 7781044
    Abstract: A recording layer including a novel organic compound for a high density optical recording medium is provided. The information may be recorded on the recording layer at a 2× speed or higher speed with a relatively lower writing power so that heat distribution of the recording layer in the irradiated area is not likely to become steep both in time and space. The organic compound incorporated in the recording layer has the following general chemical structural formula (I).
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: August 24, 2010
    Assignee: Industrial Technology Research Institute
    Inventors: Ming-Chia Li, An-Tse Lee, Chien-Liang Huang, Chung-Ta Cheng, Kuo-Chi Chiu, Tzuan-Ren Jeng
  • Publication number: 20090299042
    Abstract: This present disclosure relates to a process for manufacturing 3(R)-(2-hydroxy-2,2-dithien-2-ylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide by reacting 2-hydroxy-2,2-dithien-2-ylacetic acid 1-azabicyclo[2.2.2]oct-3(R)yl ester and 3-phenoxypropyl bromide, wherein the reaction takes place in a solvent or mixtures of solvents having a boiling point from 50° C. to 210° C. and chosen from ketones and cyclic ethers.
    Type: Application
    Filed: July 16, 2007
    Publication date: December 3, 2009
    Inventors: Nuria Busquets Baque, Francesca Pajuelo Lorenzo
  • Patent number: 7029502
    Abstract: The present invention relates to an azo dye of formula wherein D is the radical of a diazo component of the benzene, naphthalene, diphenyl, thiophene, benzothiazole, benzisothiazole, thiadiazole, indazole, benzotriazole, pyrazole, anthraquinone, naphthalic acid imide, chromone, phthalimide or diphenylene oxide series, R1 is an unsubstituted or substituted aryl radical and R2 is an unsubstituted or substituted aryl radical, with the exception of the compounds of formulae (1a) and (1b) to a process for its preparation and to its use in a process for the production of mass-colored plastics or polymeric color particles, and in the dyeing or printing of semi-synthetic or synthetic hydrophobic fiber materials.
    Type: Grant
    Filed: January 18, 2002
    Date of Patent: April 18, 2006
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Antoine Clément, Anton Andreoli, Urs Lauk, Athanassios Tzikas
  • Publication number: 20040103820
    Abstract: A 2-methoxyphenol derivative and an ink composition containing the 2-methoxyphenol derivative, an aqueous medium, and a colorant enhance light resistance by absorbing ultraviolet (UV) light, provide wettability and stabilize a colorant. The ink composition prepared using the 2-methoxyphenol derivative also has improved light resistance, wettability and stabilizes a colorant and does not require an additional light-resistant agent.
    Type: Application
    Filed: November 12, 2003
    Publication date: June 3, 2004
    Applicant: SAMSUNG Electronics Co., Ltd.
    Inventors: Yeon-Kyoung Jung, Seung-Min Ryu
  • Publication number: 20030224298
    Abstract: Sulfonyldiazomethane compounds containing a long-chain alkylcyclohexyl group are novel and useful as photoacid generators. Chemical amplification type resist compositions comprising the same are suited for microfabrication because of many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris left after coating, development and peeling, and improved pattern profile after development.
    Type: Application
    Filed: May 1, 2003
    Publication date: December 4, 2003
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Koji Hasegawa, Takao Yoshihara, Kazunori Maeda, Toshihiko Fujii
  • Patent number: 6407219
    Abstract: The invention concerns a method for preparing an azoiminoether hydrochloride which consists in reacting an azonitrile with an alcohol and hydrochloric acid in an aromatic solvent, wherein the molar ratio R=HCl/azonitrile is >2 when the alcohol is methanol and >3 when the alcohol is ethanol or a higher alcohol. The invention also concerns a method for preparing an azocarboxylic acid ester which consists in the synthesis of an azoiminoether hydrochloride by the inventive method and, hydrolysis in the presence of the resulting azoiminoether hydrochloride. Said methods enable to obtain liquid composition of azocarboxylic acid esters. The invention further concerns mixed azoiminoether salts of formula (II′). The invention also concerns mixed azoiminocarboxylic acid esters corresponding to the formula (III′).
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: June 18, 2002
    Assignee: Atofina
    Inventor: Paul Bourdauducq
  • Patent number: 6335431
    Abstract: A method of separation of a racemic isomer and a meso isomer from a mixture of a racemic isomer and a meso isomer of a compound shown by the general formula [1] (wherein R1 and R2 are each independently a lower alkyl group or a cyano group, which are different from each other, R3 and R4 are each independently a lower alkyl group, and R5 is a hydrogen atom or a lower alkoxy group), which comprises treating the mixture with a water soluble organic solvent.
    Type: Grant
    Filed: January 10, 2001
    Date of Patent: January 1, 2002
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventor: Toshiyasu Ito
  • Patent number: 6333425
    Abstract: The invention is related to ionic compounds, derivatives of malononitrile, in which the anionic load has been displaced. An ionic compound disclosed by the invention includes an anionic portion combined with at least one cationic portion M+m in sufficient number to ensure overall electronic neutrality; the compound is further comprised of M as a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation with the valence m, an organic cation with the valence m, or an organometallic cation with the valence m. The anionic portion corresponds to one of the formulas RD—Y—C(C≡N)2− or Z—C(C≡N)2− in which Z is an electroattractive group, RD is an organic radical, and Y is a carbonyl, a thiocarbonyl, a sulfonyl, a sulfinyl, or a phosphonyl. The compounds can be used notably for ionic conducting materials, electronic conducting materials, colorants, and the catalysis of various chemical reactions.
    Type: Grant
    Filed: November 19, 1998
    Date of Patent: December 25, 2001
    Assignees: Hydro-Quebec, Centre National de la Recherche Scientifique
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Yves Choquette
  • Publication number: 20010020088
    Abstract: A method for separation of a racemic isomer and a meso isomer from a mixture of a racemic isomer and a meso isomer of a compound shown by the general formula [1] 1
    Type: Application
    Filed: January 10, 2001
    Publication date: September 6, 2001
    Applicant: Wako Pure Chemical Industries, Ltd.,
    Inventor: Toshiyasu Ito
  • Patent number: 6013826
    Abstract: A method for an addition reaction with the formation of an additional carbon--carbon bond comprising reacting an .alpha.-halogeno carboxylic acid derivative with an alkene in the presence of a catalyst shown by the general formula (1): ##STR1## wherein R.sub.1 is a lower alkyl group.
    Type: Grant
    Filed: April 22, 1998
    Date of Patent: January 11, 2000
    Assignee: Waco Pure Chemical Industries
    Inventors: Yasuyuki Kita, Atsunori Sano, Takahiro Yamaguchi, Masahisa Oka, Masato Matsugi, Kentoku Gotanda
  • Patent number: 5973125
    Abstract: An azoamide compound of the formula: ##STR1## wherein R.sup.1 through R.sup.4 are independently an alkyl group; X is an alkylene groupl Y is --O-- or --NH--; and n is an integer of 2 or more, is effective for producing a macroazo compound, which is a useful initiator for producing block copolymers.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: October 26, 1999
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Tsuneaki Maesawa, Kazuo Shiraki, Nobutaka Shimamura
  • Patent number: 5964899
    Abstract: Azo dyes containing sulphur dye entities as a constitutional component are dyes of valuable properties, in particular for the dyeing of leather.
    Type: Grant
    Filed: October 8, 1997
    Date of Patent: October 12, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Jordi Berenguer, Manuel Jose Domingo, Jose Rocas
  • Patent number: 5854406
    Abstract: An azoamide compound of the formula: ##STR1## wherein R.sup.1 through R.sup.4 are independently an alkyl group; X is an alkylene group; Y is --O-- or --N--; and n is an integer of 2 or more, is effective for producing a macroazo compound, which is a useful initiator for producing block copolymers.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: December 29, 1998
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Tsuneaki Maesawa, Kazuo Shiraki, Nobutaka Shimamura
  • Patent number: 5847091
    Abstract: A fluorine-containing azo compound having a fluorine segment at a molecular terminal is useful as a polymerization initiator for producing, for example, fluorine-containing polymers.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: December 8, 1998
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Kazuo Shiraki, Nobutaka Shimamura
  • Patent number: 5834603
    Abstract: A polymerization initiator composition, comprising an azobisamidine salt represented by the general formula (1) ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group or a cycloalkyl group, providing that R.sup.1 and R.sup.2 may together form an aliphatic ring, and Y represents --C(.dbd.NR.sup.3)--NH--R.sup.4 or a guanyl group represented by the formula (2) ##STR2## wherein R.sup.3 and R.sup.4 independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, an allyl group, a phenyl group, or a substituted phenyl group, R.sup.5 represents a lower alkylene group optionally containing a substituent group, and R.sup.6 represents a hydrogen atom or a hydroxyalkyl group, and X represents a chlorine atom, a bromine atom, or a CH.sub.3 COO-- group, and a hydrophilic organic compound.
    Type: Grant
    Filed: November 19, 1997
    Date of Patent: November 10, 1998
    Assignee: Nippoh Chemicals Co., Ltd.
    Inventors: Tsuneo Tsubakimoto, Toshiyasu Sato, Hisayuki Suzuki
  • Patent number: 5760192
    Abstract: An azodinitrile composition comprising a mixture of at least six different azodinitriles of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each independently acyclic aliphatic hydrocarbon radicals of 1-9 carbon atoms, said mixture having a freezing point of a maximum of 25.degree. C. and a process for its preparation are disclosed.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: June 2, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ernest Byron Wysong
  • Patent number: 5650498
    Abstract: The present invention provides a process for producing a spherical granule of a water-soluble azo compound, which comprises dispersing a water-soluble azo compound in a water-insoluble solvent and then add dropwise water or a hydrophilic solvent dissolving the water-soluble azo compound with stirring to granulate the water-soluble azo compound in the solution, and produce the spherical granule of the water-soluble azo compound.
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: July 22, 1997
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Hideo Amo, Masaya Kajimoto, Akihiko Goto
  • Patent number: 5563276
    Abstract: Acrylic acid or water-soluble derivatives thereof can be polymerized effectively in a short time using as a polymerization initiator an inorganic acid salt or organic acid salt of 2,2'-azobis(2-methylpropionamidoxime).
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: October 8, 1996
    Assignee: Waco Pure Chemical Industries, Ltd.
    Inventors: Hideo Takeuchi, Toshiyasu Ito, Yutaka Kojima
  • Patent number: 5554739
    Abstract: Processes for preparing a carbon product having an organic group attached to a carbon material. The carbon material is selected from graphite powder, a graphite fiber, a carbon fiber, a carbon cloth, a vitreous carbon product, and an activated carbon product. In one process at least one diazonium salt reacts with a carbon material in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon material in a protic reaction medium.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: September 10, 1996
    Assignee: Cabot Corporation
    Inventor: James A. Belmont
  • Patent number: 5324827
    Abstract: Nonlinearly optically active monomer species comprising at least two carbon-carbon activated double bonds, i.e., the polymerization of which is facilitated by the presence of an electron attracting function, and a non-centrosymmetric system of pi (.pi.
    Type: Grant
    Filed: September 9, 1993
    Date of Patent: June 28, 1994
    Assignee: Flamel Technologies
    Inventors: Yves Camberlin, Gerard Mignani, Remi Meyrueix, Gilles Tapolsky
  • Patent number: 5268509
    Abstract: This invention relates to a process for the preparation of an iron catalyst used for the hydrogenation of organic compounds comprising partially oxidizing iron or an iron alloy in particulate form at an elevated temperature in the presence of gaseous oxygen until a weight gain of from 5% to 32% is obtained; and then reducing the partially oxidized iron or iron alloy at an elevated temperature in a stream of hydrogen.The invention also relates to a process for the preparation of primary amines comprising catalytically hydrogenating nitriles corresponding to said primary amines in the presence of an iron catalyst of the invention.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: December 7, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Dietrich Liebsch, Hans-H. Schwarz, Stephan Wendel, Peter Fischer
  • Patent number: 5053496
    Abstract: The present invention generally relates to statistical monofunctional terminated reactive liquid rubbers including a statistical monofunctional carboxylic-terminated reactive liquid rubber, a statistical monofunctional amine-terminated reactive liquid rubber, and a statistical monofunctional epoxy-terminated reactive liquid rubber. These polymers are pourable, making them useful in a variety of applications particularly as toughening agents for epoxy resins to which they impart good physical properties.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: October 1, 1991
    Assignee: The BF Goodrich Company
    Inventors: Robert J. Bertsch, Alan R. Siebert
  • Patent number: 5037963
    Abstract: The preparation of symmetrical azodinitriles prepared from keto acids is disclosed. A keto acid of the formula ##STR1## is reacted with M(CN).sub.x and an ammonia source to obtain an aminonitrile metal carboxylate of the formula ##STR2## The aminonitrile metal carboxylate is reacted with M.sub.1 (OCl).sub.x with the proviso that no alcohol or surface active agent is utilized to form a metal salt of an azo compound. This metal salt is reacted with mineral acid to give the symmetrical azodinitrile compound of the formula ##STR3## R.sub.1 is an alkyl group containing from 1 to about 12 carbon atoms and R.sub.2 is an alkylene group containing from 1 to about 12 carbon atoms. M is a metal comprising lithium, sodium, potassium, magnesium or calcium; M.sub.1 is a metal comprising sodium, potassium or calcium; and x is the valence of M and M.sub.1.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: August 6, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5010178
    Abstract: Disclosed are processes for the preparation of mixed azodinitriles initiators of the formulae ##STR1## These initiators are prepared by reacting a keto acid of the formula ##STR2## with M(CN).sub.x, a hydrazine source, a ketone of the formula ##STR3## and hydrochloric acid to form ##STR4## The hydrazo intermediates are reacted with chlorine gas in the presence of acetone solvent to oxidize the mixture of hydrazo intermediates to the mixed azonitrile initiators. R.sub.1 is an alkyl group containing from about 1 to about 12 carbon atoms, R.sub.2 is non-existent or an alkylene group containing from 1 to about 12 carbon atoms, or a cycloalkylene or alkyl cycloalkylene group containing from about 3 to about 12 carbon atoms, R.sub.3 and R.sub.4 are alkyl groups containing from 1 to about 12 carbon atoms, or one of R.sub.3 and R.sub.4 is an alkoxy group containing from 1 to about 4 carbon atoms and M is a metal comprising lithium, sodium, potassium, magnesium, or calcium.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: April 23, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5010177
    Abstract: Disclosed are processes for the preparation of an azonitrile initiator having both a low salt and low water content of the formula ##STR1## This initiator is prepared by reacting a keto acid of the formula ##STR2## with M(CN).sub.x, a hydrazine source, and hydrochloric acid to form ##STR3## The hydrazo intermediate is reacted with chlorine gas in the presence of acetone to oxidize the hydrazo intermediate to the azonitrile initiator. After oxidation, the reaction mixture is permitted to separate into layers. The bottom aqueous layer is removed and discarded. The upper acetone-azonitrile initiator level is treated with solid calcium chloride or a saturated calcium chloride or sodium chloride solution. This salting out procedure generates an additional water layer that further contains (M(Cl).sub.x. The final acetone-azonitrile initiator solution has a low salt and low water content.R.sub.1 is an alkyl group containing from about 1 to about 12 carbon atoms, R.sub.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: April 23, 1991
    Assignee: The B. F. Goodrich Company
    Inventors: John T. Lai, Deborah S. Filla
  • Patent number: 5010179
    Abstract: The preparation of mixed, symmetrical azonitrile initiators prepared from keto acids and aminonitrile is disclosed. A keto acid of the formula ##STR1## is reacted with M(CN).sub.x and an ammonia source to obtain an aminonitrile metal carboxylate of the formula ##STR2## The aminonitrile metal carboxylate is reacted with M.sub.1 (OCl).sub.x in the presence of a surfactant to form an azonitrile metal carboxylate. The excess M.sub.1 (OCl).sub.x is reacted with an aminonitrile of the formula ##STR3## in the presence of the surfactant to form a symmetrical azonitrile initiator ##STR4## The aminonitrile metal carboxylate is reacted with mineral acid to give the symmetrical azonitrile compound of the formula ##STR5## R.sub.1 is an alkyl group containing from about 1 to about 12 carbon atoms and R.sub.2 is an alkylene group containing from 1 to about 12 carbon atoms. M is a metal comprising lithium, sodium, potassium, magnesium or calcium; M.sub.
    Type: Grant
    Filed: December 26, 1989
    Date of Patent: April 23, 1991
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4950742
    Abstract: An azoimino ether, which is an intermediate for preparing polymerization initiators, is prepared by reacting a hydrazonitrile having a hydrazo group and at least one cyano group in the molecule with chlorine in the presence of an alcohol, in a non-aqueous organic solvent.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: August 21, 1990
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Kazuo Ichiriki, Motoaki Tanaka, Toru Okugawa, Hiroyoshi Nawa
  • Patent number: 4916216
    Abstract: Granules of azobisamidine salt can be produced by granulating a powder of azobisamidine salt using a limited amount of water or a mixture of water and a water-soluble organic solvent such as methanol are convenient in handling without deteriorating the quality and can be used as a water-soluble polymerization initiator.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: April 10, 1990
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Motoaki Tanaka, Takanori Toyama, Hiroki Sugioka
  • Patent number: 4889923
    Abstract: Azo compounds corresponding to the general formula (1) ##STR1## in which m represents the number 1 or 2, the cyano groups being attached to D in the ortho-position relative to the azo group,n denotes the number 1 or 2,Y is the vinyl group or a .beta.-sulfatoethyl group,D denotes a radical of a diazo component of the benzene or naphthalene series which is optionally additionally substituted, but is otherwise free from anionic groups, andK denotes a radical of a coupling component which is optionally additionally substituted, but is otherwise free from anionic groups.The compounds have valuable fiber-reactive dyestuff properties and are suitable for dyeing both hydrophilic and hydrophobic materials, in particular fiber materials, such as, for example, cellulose, wool, synthetic polyamide and polyester.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: December 26, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Mischke, Hans J. Schladetsch
  • Patent number: 4831096
    Abstract: Mixtures of azolakanes of varying thermal stabilities at least one of which is an unsymmetrical azoalkane (R--N.dbd.N--R'), are prepared by reacting 4 equivalents of a mixture of two or more primary alkyl, cycloalkyl or aralkylamines with 1 equivalent of sulfuryl chloride in an inert solvent and oxidizing the resulting mixture of sulfamide products with basic bleach. The unsymmetrical azoalkanes can be separated from the symmetrical azoalkanes by a variety of conventional techniques. The azoalkane mixtures are excellent polymerization initiators for vinyl monomers and curing agents for unsaturated polyester resins.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: May 16, 1989
    Assignee: Pennwalt Corporation
    Inventor: Ronald E. MacLeay
  • Patent number: 4826959
    Abstract: A mixture of an isomer of 2,2'-azobis(2,4-dimethylvaleronitrile) having a low melting point in an amount of about 70% by weight or more and an isomer of 2,2'-azobis(2,4-dimethylvaleronitrile) having a high melting point in an amount of about 30% by weight or less shows excellent solvent solubility, which is higher than that of the isomer having a low melting point. The mixture is useful as a polymerization initiator, and also as a blowing agent.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 2, 1989
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Motoaki Tanaka, Tsutomu Miyagawa, Hideo Takeuchi
  • Patent number: 4684717
    Abstract: A process for the preparation of a diazocyano acid, which comprises reacting a keto-acid or its sodium salt with a cyanogen compound such as sodium cyanide or hydrogen cyanide and a hydrazine in water to form a concentrated aqueous solution of a hydrazo compound, adding acetone or acetone and water to the concentrated aqueous solution to form an acetone-water solution of the hydrazo compound, adding an oxidant such as chlorine gas to the solution to oxidize the hydrazo compound and form a diazocyano acid, forming at least two transparent liquid layers by adding acetone and/or water to the obtained reaction mixture during or after oxidation if necessary, and further adding sodium chloride to the reaction mixture if necessary, and separating and recovering the upper layer of the acetone-water solution containing the diazocyano acid from the mixture.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: August 4, 1987
    Assignee: UBE Industries, Ltd.
    Inventors: Hidetomo Ashitaka, Kazuya Jinda, Yoshiyuki Miwa
  • Patent number: 4684718
    Abstract: A process for the preparation of a diazocyano acid, which comprises reacting a keto-acid or its sodium salt with a cyanogen compound such as sodium cyanide or hydrogen cyanide and a hydrazine in water to form a concentrated aqueous solution of a hydrazo compound, adding acetone and/water to the concentrated aqueous solution to form a solution of the hydrazo compounds, adding chlorine gas to the solution to oxidize the hydrazo compound and form a diazocyano acid, adding acetone to the obtained reaction mixture during or after the oxidation if necessary, and separating and recovering the supernatant layer of the acetone-water solution containing the diazocyano acid from the mixture.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: August 4, 1987
    Assignee: UBE Industries, Ltd.
    Inventors: Hidetomo Ashitaka, Kazuya Jinda, Yoshiyuki Miwa
  • Patent number: 4604455
    Abstract: Mixtures of azoalkanes of varying thermal stabilities at least one of which is an unsymmetrical azoalkane (R--N.dbd.N--R'), are prepared by reacting 4 equivalents of a mixture of two or more primary alkyl, cycloalkyl or aralkylamines with 1 equivalent of sulfuryl chloride in an inert solvent and oxidizing the resulting mixture of sulfamide products with basic bleach. The unsymmetrical azoalkanes can be separated from the symmetrical azoalkanes by a variety of conventional techniques. The azoalkane mixtures are excellent polymerization initiators for vinyl monomers and curing agents for unsaturated polyester resins.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: August 5, 1986
    Assignee: Pennwalt Corporation
    Inventor: Ronald E. MacLeay
  • Patent number: 4585857
    Abstract: Di-t-octyldiazene is prepared in improved yield, purity and economics by oxidizing N,N'-di-t-octylsulfamide with sodium hypochlorite solution in a strongly basic medium at a temperature of 65.degree.-90.degree. C. in a minimal amount of hydrocarbon or chlorinated hydrocarbon solvent for about 2 to 5 hours until completion of the reaction. The employment of phase transfer catalysts or t-butyl alcohol in the oxidation is optional. Di-t-octyldiazene is used as a polymerization initiator for vinyl monomers and as a curing agent for unsaturated polyester resins.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: April 29, 1986
    Assignee: Pennwalt Corporation
    Inventor: Ronald E. MacLeay
  • Patent number: 4546174
    Abstract: There is described a process for the production of a compound of formula I, ##STR1## in which at least one each of R.sub.1, R.sub.2 and R.sub.3, and of R.sub.4, R.sub.5 and R.sub.6, represents an electron withdrawing group, or one of R.sub.1, R.sub.2 and R.sub.3 together with one of R.sub.4, R.sub.5 and R.sub.6 form a --CO-- group, and the remainder of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6, which may be the same or different, each represent an electron withdrawing group, alkyl, cycloalkyl, phenyl or phenylalkyl,or R.sub.1 and R.sub.2, or R.sub.4 and R.sub.5 , and R.sub.1 and R.sub.4, may together form a --(CH.sub.2).sub.n --chain, in which n is a whole number up to 5,the alkyl, cycloalkyl, phenyl or phenylalkyl group or the --(CH.sub.2).sub.n --chain optionally being substituted, which comprises reacting a compound of formula II, ##STR2## in which R.sub.1 a, R.sub.2 a and R.sub.3 a have the same significances as R.sub.1, R.sub.2, and R.sub.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: October 8, 1985
    Assignee: FBC Limited
    Inventors: Martyn W. Whitmore, Michael D. Pollard, Stephen R. Smythe