The Cyano Group Is Bonded Directly To The Carbon Adjacent To The Carbonyl Carbon (e.g., Alpha Cyano Acrylates, Etc.) Patents (Class 558/443)
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Patent number: 5637752Abstract: 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: GrantFiled: August 17, 1995Date of Patent: June 10, 1997Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Katsumi Nakamura, Yasuyuki Takayanagi, Masaaki Seya
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Patent number: 5589554Abstract: An adhesive composition is here disclosed which comprises a 2-cyanoacrylate and at least one of compounds (a) and (b):(a) an addition reaction product of an epoxy group and a compound having a cyano group and a carboxylic acid group in its molecule, and(b) a compound having a cyano group and a carboxylic acid group in its molecule. A process for preparing the adhesive composition is also disclosed herein. According to the present invention, the 2-cyanoacrylate-based adhesive composition can be obtained which is excellent in storage stability and hardening properties of thick films and which has a high hardening rate and remarkably improved surface hardening properties of the adhesive composition itself bulged from between adherends. Particularly, the 2-cyanoacrylate bulged from between the adherends can harden rapidly, so that the vaporization of the 2-cyanoacrylate can be minimized.Type: GrantFiled: September 16, 1994Date of Patent: December 31, 1996Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5504252Abstract: 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: GrantFiled: May 5, 1995Date of Patent: April 2, 1996Assignee: Loctite CorporationInventor: Philip Klemarczyk
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Patent number: 5468870Abstract: 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: GrantFiled: October 20, 1994Date of Patent: November 21, 1995Assignee: AGFA-GAVAERT, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5466764Abstract: There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate. In particular, the adhesive strength of the 2-cyanoacrylate-based adhesive composition can be remarkably increased without lowering the hardening rate, and so the 2-cyanoacrylate-based adhesive composition can exert a sufficient resistance to impact and the like at the time of the adhesion of metals, rubbers, plastics and lumbers and the reliability of adherends can be improved.Type: GrantFiled: September 16, 1994Date of Patent: November 14, 1995Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5405826Abstract: 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: GrantFiled: January 13, 1993Date of Patent: April 11, 1995Assignee: Rhone Poulenc Agriculture LimitedInventors: Richard H. Hewett, Simon N. Pettit, Philip H. G. Smith
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Patent number: 5347032Abstract: 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: GrantFiled: August 2, 1993Date of Patent: September 13, 1994Assignee: BASF AktiengesellschaftInventors: Helmut Reichelt, Clemens Grund
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Patent number: 5266702Abstract: 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: GrantFiled: September 19, 1990Date of Patent: November 30, 1993Assignee: Council of Scientific & Industrial ResearchInventors: Durairaj Bhaskaran, Pradeep K. Dhal, Sanjay P. Kashikar, Ratnaprabha S. Khisti, Babanrao M. Shinde, Swaminathan Sivaram
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Patent number: 5210280Abstract: 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: GrantFiled: February 19, 1992Date of Patent: May 11, 1993Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5175337Abstract: A novel neopentyl .alpha.-cyanoacrylate is provided. It has superior adhesive properties even at high temperatures and whitening-preventing property.Type: GrantFiled: July 18, 1991Date of Patent: December 29, 1992Assignee: Three Bond Co., Ltd.Inventors: Hiroyuki Mikuni, Toshiyuki Chikusa
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Patent number: 4986884Abstract: 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: GrantFiled: October 28, 1987Date of Patent: January 22, 1991Assignee: Bayer AktiengesellschaftInventors: Wolfgang Arlt, Helmut Waniczek, Richard Viard, Dieter Bruck
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Patent number: 4927954Abstract: 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: GrantFiled: April 19, 1989Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
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Patent number: 4902334Abstract: 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: GrantFiled: October 31, 1984Date of Patent: February 20, 1990Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
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Patent number: 4769459Abstract: 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: GrantFiled: November 3, 1986Date of Patent: September 6, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ranjan C. Patel, Ian J. Ferguson, Herbert J. Pennicott
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Patent number: 4764545Abstract: 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: GrantFiled: January 8, 1987Date of Patent: August 16, 1988Assignee: Ohara Paragium Chemical, Co., Ltd.Inventor: Ethuo Yosida
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Patent number: 4734520Abstract: 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: GrantFiled: May 29, 1986Date of Patent: March 29, 1988Assignee: Vianova Kunstharz, A.G.Inventors: Helmut Plum, Willibald Paar
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Patent number: 4705650Abstract: 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: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4584145Abstract: 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: GrantFiled: June 19, 1985Date of Patent: April 22, 1986Assignee: Montedison S.p.A.Inventors: Roberto Santi, Giuseppe Cometti, Anselmo Pagani