The Cyano Group Is Bonded Directly To The Carbon Adjacent To The Carbonyl Carbon (e.g., Alpha Cyano Acrylates, Etc.) Patents (Class 558/443)
  • Patent number: 5637752
    Abstract: A cyanoacetic acid higher ester represented by the general formula: NCCH.sub.2 COOR', wherein R' represents an alkyl group having 4 to 20 carbon atoms, is prepared by subjecting a cyanoacetic acid ester represented by the general formula: NCCH.sub.2 COOR.sup.1, wherein R.sup.1 represents an alkyl group having 1 to 3 carbon atom, to a transesterification with an alcohol represented by the general formula: R'OH, wherein R' represents an alkyl group having 4 to 20 carbon atoms, in the presence of a specific tin compound as the catalyst. According to the present invention, the cyanoacetic acid higher esters which are useful as intermediates for pharmaceuticals and agricultural chemicals as well as intermediates for industrial products can be prepared easily and in higher yield as compared with conventional methods, by using a cyanoacetic acid ester and an alcohol which are less expensive and easily available as raw materials.
    Type: Grant
    Filed: August 17, 1995
    Date of Patent: June 10, 1997
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Katsumi Nakamura, Yasuyuki Takayanagi, Masaaki Seya
  • 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: 5504252
    Abstract: A method of preparing an .alpha.-cyanoacrylate ester of a desired alcohol includes the steps ofpreparing a compound which is an .alpha.-selenoaryl-.alpha.-cyanopropionate ester of the desired alcohol,oxidizing said .alpha.-selenoaryl-.alpha.-cyanopropionate ester to the corresponding selenoxide,eliminating arylselenic acid from the selenoxide to produce said .alpha.-cyanoacrylate ester, andseparating said .alpha.-cyanoacrylate ester from the selenic acid.At temperatures of about 0.degree. C. or higher, the elimination step occurs concurrently with the oxidizing step using a peroxide or ozone oxidizing agent. The desired cyanoacrylate ester is obtained in good yield and very high purity. The method can be used to prepare difficult to synthesize plural functional cyanoacrylate monomers and mono- cyanoacrylate monomers regardless of alcohol chain length.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: April 2, 1996
    Assignee: Loctite Corporation
    Inventor: Philip Klemarczyk
  • Patent number: 5468870
    Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: November 21, 1995
    Assignee: AGFA-GAVAERT, N.V.
    Inventor: Luc J. Vanmaele
  • 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: 5405826
    Abstract: Pyrido[2,3-d]pyridazin-5-one and pyrido[2,3-d]pyridazin-5-thione derivatives of general formula (I): ##STR1## wherein R and R.sup.1 independently represent hydrogen, optionally halogenated alkyl, alkenyl or alkynyl, optionally substituted heterocycle or a group --[CR.sup.41 R.sup.42 ].sub.n -(phenyl)-(R.sup.3).sub.q ;R.sup.2 represents halogen, optionally halogenated alkyl, alkenyl or alkynyl, CN; --CO.sub.2 R.sup.4 ; --S(O).sub.r R.sup.4 ; --NO.sub.2 ; --NR.sup.41 R.sup.42 ; --OH; --COR.sup.4, --S(O).sub.r R.sup.5, --CO.sub.2 R.sup.5, --OR.sup.5 ; --CONR.sup.41 R.sup.42, --OSO.sub.2 R.sup.5, --OSO.sub.2 R.sup.6, --OCH.sub.2 R.sup.5, --N(R.sup.41)COR.sup.6, --N(R.sup.41)SO.sub.2 R.sup.5, --N(R.sup.41)SO.sub.2 R.sup.6, --SO.sub.2 NR.sup.41 R.sup.42, optionally substituted phenyl, alkoxy or haloalkoxy;X represents oxygen or sulphur;R.sup.3 represents halogen, optionally halogenated alkyl, alkenyl, alkoxy, alkynyl, --OH, --S(O).sub.r R.sup.4, --CO.sub.2 R.sup.4, COR.sup.4, --CN, --NO.sub.2, --NR.sup.41 R.sup.
    Type: Grant
    Filed: January 13, 1993
    Date of Patent: April 11, 1995
    Assignee: Rhone Poulenc Agriculture Limited
    Inventors: Richard H. Hewett, Simon N. Pettit, Philip H. G. Smith
  • Patent number: 5347032
    Abstract: A process for the preparation of C.sub.4 -C.sub.10 alkyl cyanoacetates by the reaction of cyanoacetic acid with C.sub.4 -C.sub.10 alkanols at a temperature of from 35.degree. to 150.degree. C. and under a pressure of from 70 to 1013 mbar, in the presence of catalytic amounts of acid, while a C.sub.4 -C.sub.10 alkanol/water azeotrope is separated during the reaction.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: September 13, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Reichelt, Clemens Grund
  • Patent number: 5266702
    Abstract: Disclosed are reactive anionic initiators of the general formula [ArCHR.sub.1 R.sub.2 N(R.sub.3 R.sub.4 R.sub.5 R.sub.6 ] wherein Ar=phenyl, substituted phenyl, or a heterocyclic compound, R.sub.1 =R.sub.2 =H, ester, cyano, alkyl, aryl, 1,3-oxazoline, N,N-dimethyl amide and other similar alpha activating groups, or combination of them, or one of R.sub.1 or R.sub.2 together with Ar, where Ar is a phenyl or substituted phenyl, is a nitrogen atom containing heterocyclic compound and the other being a nitrile group, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be same or different and represent substituted alkyl, cycloalkyl, arylalkyl or aryl or to of the R.sub.3, R.sub.4, R.sub.5 and R.sub.6 together with nitrogen atom form a heterocycle with the condition that the sum of all carbon atoms of all R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is from 12 to 50 and no more than one of the R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is an aryl derivative.
    Type: Grant
    Filed: September 19, 1990
    Date of Patent: November 30, 1993
    Assignee: Council of Scientific & Industrial Research
    Inventors: Durairaj Bhaskaran, Pradeep K. Dhal, Sanjay P. Kashikar, Ratnaprabha S. Khisti, Babanrao M. Shinde, Swaminathan Sivaram
  • Patent number: 5210280
    Abstract: A process for the preparation of alkanedioic acid derivatives comprising reacting an alkenoic acid derivative with carbon monoxide and a nucleophilic compound having a mobile hydrogen atom in the presence of a catalyst system comprising a source of a Group VIII metal, a source of a bidentate diphosphine liquid, a source of an anion and a source of a quinone promoter.
    Type: Grant
    Filed: February 19, 1992
    Date of Patent: May 11, 1993
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5175337
    Abstract: A novel neopentyl .alpha.-cyanoacrylate is provided. It has superior adhesive properties even at high temperatures and whitening-preventing property.
    Type: Grant
    Filed: July 18, 1991
    Date of Patent: December 29, 1992
    Assignee: Three Bond Co., Ltd.
    Inventors: Hiroyuki Mikuni, Toshiyuki Chikusa
  • Patent number: 4986884
    Abstract: A process for the production of monomeric .alpha.-cyanoacrylates by pryrolysis of poly-.alpha.-cyanoacrylates and subsequent distillation of the resulting monomeric .alpha.-cyanoacrylates.
    Type: Grant
    Filed: October 28, 1987
    Date of Patent: January 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Arlt, Helmut Waniczek, Richard Viard, Dieter Bruck
  • Patent number: 4927954
    Abstract: A continuous process for efficiently co-producing secondary alcohols of long-chain olefins and lower carboxylic acid esters, comprising (I) performing an acid/olefin reaction in the presence of a heterogeneous catalyst such as Amberlyst 15, and (II) performing an ester-exchange reaction in the presence of, e.g., titanium alcoholate. A desirable feature of the process is the ability to produce co-products of choice.
    Type: Grant
    Filed: April 19, 1989
    Date of Patent: May 22, 1990
    Assignee: Union Carbide Chemicals and Plastics Company, Inc.
    Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
  • Patent number: 4902334
    Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.
    Type: Grant
    Filed: October 31, 1984
    Date of Patent: February 20, 1990
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
  • Patent number: 4769459
    Abstract: A radiation-sensitive element capable of recording an image upon image-wise exposure to radiation of selected wavelength, the element comprising, as the image-forming components, an effective amount of a bleachable dye in reactive association with an iodonium ion. Suitable dyes include polymethine dyes having an oxidation potential between 0 and +1 volt.
    Type: Grant
    Filed: November 3, 1986
    Date of Patent: September 6, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ranjan C. Patel, Ian J. Ferguson, Herbert J. Pennicott
  • Patent number: 4764545
    Abstract: A process for preparing an .alpha.-cyanoacrylate compound characterized by the steps of thermally depolymerizing a condensation product obtained from a cyanoacetic acid ester, and formaldehyde or a polymer thereof using as a catalyst a polymerizable imine represented by the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and are each CH.sub.3 or H to obtain a crude monomer, and rectifying the crude monomer and an adhesive composition comprising as its main component an .alpha.-cyanoacrylate compound prepared by the above process.
    Type: Grant
    Filed: January 8, 1987
    Date of Patent: August 16, 1988
    Assignee: Ohara Paragium Chemical, Co., Ltd.
    Inventor: Ethuo Yosida
  • Patent number: 4734520
    Abstract: Crosslinking components for hydroxy and/or primary and/or secondary amino group containing paint binders for the crosslinking of synthetic resins carrying at least two groups capable of ester or amide formation with carboxylic acids. In particular there is disclosed the use of the crosslinking components in compositions for electrodeposition (ED) whereby at 120.degree. C. and above coatings with extraordinary paint performance are obtained. The use of methyl or ethyl esters gives extremely low condensation losses. The crosslinking components are obtained through reaction of one mole of a diisocyanate, preferably at room temperature, in the presence of sodium, or preferably sodium phenolate, as catalyst, with at least one mole of a CH-active alkyl ester of the general formula X--CH.sub.2 --COOR, wherein X is --COOR, --CN or CH.sub.3 --CO-- and R is an alkyl radical with 1 to 8 C-atoms and subsequent reaction of the free isocyanate groups with polyamines of the general formula H.sub.2 N--(R--NH).sub.n --R--NH.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: March 29, 1988
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Helmut Plum, Willibald Paar
  • Patent number: 4705650
    Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4584145
    Abstract: There is described a process for preparing carbonyl compounds of formula: ##STR1## by oxidation of compounds of formula: ##STR2## wherein X=--CN, --COOR, Y=--COOR.sub.1, --CN, and R, R.sub.1, like or unlike each other, are inert radicals, by employing oxygen or air as oxidants, at least a catalyst selected from the salts of organic or inorganic acids of Mn, Co, Cu and Fe, from 0 to 60 moles of an alkaline salt of an aliphatic carboxylic acid per gram-atom of catalyst metal, in a polar solvent, at temperatures ranging from 30.degree. C. to 200.degree. C. and maintaining the reaction medium anhydrous.The present invention relates to a process for preparing carbonyl compounds by catalytic oxidation of compounds containing an activated methylene group.
    Type: Grant
    Filed: June 19, 1985
    Date of Patent: April 22, 1986
    Assignee: Montedison S.p.A.
    Inventors: Roberto Santi, Giuseppe Cometti, Anselmo Pagani