Sulfur Or Halogen Attached Indirectly To The Thiocyano Group By Acyclic Nonionic Bonding Patents (Class 558/15)
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Patent number: 8212064Abstract: An oligomer of the formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]mG??(I) wherein G is an I; OH; OC(O)CH?CH2; OC(O)CCH3?CH2; OC(O)CCl?CH2; NR1H; N3; NCO; SQ wherein Q is H, alkyl, (CH2)nOH, (CH2)nNH2, (CH2)nOC(O)C(Me)=CH2, or (CH2)nNHC(O)C(Me)=CH2; SCN; COOH; SO3H; NHCOCH?CH2; NHCOC(CH3)?CH2); OC(O)NHCH2CH2OC(O)C(CH3)?CH2; or OC(O)NHCH2CH2OC(O)C(CH3)?CH2; subscript n is an integer from 1 to about 6, subscript x is an integer from 1 to about 6, subscripts y, z and m are each independently 1, 2 or 3, or a mixture thereof, the total number of carbons in said formula (I) excluding G ranges from about 8 to about 22, and a process for preparation thereof.Type: GrantFiled: May 14, 2008Date of Patent: July 3, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
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Patent number: 8153846Abstract: The present invention provides a method of making sulfur containing fluoroalkyl amines which overcomes the problems of previously known methods. Sulfur containing fluoroalkyl amines are useful as intermediates for compounds which are in turn useful for imparting water and oil repellency to textiles. Sulfur containing fluoroalkyl amines used in this manner may be found in Example 8 of Rondestvedt et al. (U.S. Pat. No. 3,655,732) wherein they are made by reacting an iodo-fluoroalkyl with an aminoalkyl thiol. Specifically, Rondestvedt et al. teaches reacting CF3(CF2)5(CH2)2I (an iodo-fluoroalkyl) with HS—CH2CH2—NH2 (an aminoalkyl thiol) to make CF3(CF2)5(CH2)2—S—CH2CH2—NH2 (a sulfur containing fluoroalkyl amine). Unlike previously known methods, the method of the present invention can achieve higher yields of sulfur containing fluoroalkyl amines without resorting to costly solvents.Type: GrantFiled: November 18, 2008Date of Patent: April 10, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Axel Hans-Joachim Herzog, Hollis Thomas Warren, Brent Ryan Gonska
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Publication number: 20090287010Abstract: An oligomer of the formula (I): CnF2n+1(CH2)x[(CF2CF2)y(CH2CH2)z]mG??(I) wherein G is an I; OH; OC(O)CH?CH2; OC(O)CCH3?CH2; OC(O)CCl?CH2; NR1H; N3; NCO; SQ wherein Q is H, alkyl, (CH2)nOH, (CH2)nNH2, (CH2)nOC(O)C(Me)?CH2, or (CH2)nNHC(O)C(Me)?CH2; SCN; COOH; SO3H; NHCOCH?CH2; NHCOC(CH3)?CH2); OC(O)NHCH2CH2OC(O)C(CH3)?CH2; or OC(O)NHCH2CH2OC(O)C(CH3)?CH2; subscript n is an integer from 1 to about 6, subscript x is an integer from 1 to about 6, subscripts y, z and m are each independently 1, 2 or 3, or a mixture thereof, the total number of carbons in said formula (I) excluding G ranges from about 8 to about 22, and a process for preparation thereof.Type: ApplicationFiled: May 14, 2008Publication date: November 19, 2009Applicant: E.I. du Pont de Nemours and CompanyInventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
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Patent number: 7393961Abstract: (Per)haloethers having formula: X-(Rf)L-O—CF2CF2—O—CX1X2—CFX3X4 , ??(I) process for obtaining them and hypofluorites usable in the synthesis of said (per)haloethers.Type: GrantFiled: March 8, 2005Date of Patent: July 1, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 6222057Abstract: According to the present invention, provided are (1) a process for the preparation of 2-chloro-5-chloromethyl-1,3-thiazole, by reacting 3-chloro-1-isothiocyanato-1-propene with a chlorinating agent, (2) a process for the preparation of 3-chloro-1-isocyanato-1-propene, by rearranging 3-chloro-1-thiocyanato-2-propene in the presence of a salt of one or more than one metal selected from the group consisting of metals belonging to Group 2A, Group 7A, Group 8 and Group 1B of the long-form periodic table, and (3) a process for the preparation of 3-chloro-1-thiocyanato-2-propene, by reacting 1,3-dichloropropene and a thiocyanate salt (a) in the presence of water, (b) in the presence of an organic solvent which is water-soluble and has a boiling point of 150° C. or lower, or (c) in an organic solvent in the presence of a phase transfer catalyst.Type: GrantFiled: April 7, 2000Date of Patent: April 24, 2001Assignee: Kuraray Co., Ltd.Inventors: Hideki Matsuda, Goro Asanuma, Manzo Shiono
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Patent number: 6103921Abstract: According to the present invention, provided are(1) a process for the preparation of 2-chloro-5-chloromethyl-1,3-thiazole, by reacting 3-chloro-1-isothiocyanato-1-propene with a chlorinating agent,(2) a process for the preparation of 3-chloro-1-isocyanato-1-propene, by rearranging 3-chloro-1-thiocyanato-2-propene in the presence of a salt of one or more than one metal selected from the group consisting of metals belonging to Group 2A, Group 7A, Group 8 and Group 1B of the long-form periodic table, and(3) a process for the preparation of 3-chloro-1-thiocyanato-2-propene, by reacting 1,3-dichloropropene and a thiocyanate salt(a) in the presence of water,(b) in the presence of an organic solvent which is water-soluble and has a boiling point of 150.degree. C. or lower, or(c) in an organic solvent in the presence of a phase transfer catalyst.Type: GrantFiled: January 5, 1999Date of Patent: August 15, 2000Assignee: Kuraray Co., Ltd.Inventors: Hideki Matsuda, Goro Asanuma, Manzo Shiono
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Patent number: 6077866Abstract: Novel benzophenonehydrazone derivatives represented by the formula (I): ##STR1## wherein, R.sup.1 is halogen; R.sup.2 is hydrogen or C.sub.1-4 alkyl; R.sup.3 is cyano, optically substituted C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.1-4 alkyl-carbonyl or C.sub.1-4 alkoxy-thiocarbonyl; R.sup.4 is hydrogen, phenyl, optionally substituted C.sub.1-6 alkyl, optionally substituted C.sub.2-8 alkenyl, --CO--R.sup.8, --CO--O--R.sup.9 or ##STR2## R.sup.5 is hydrogen, formyl, phenyl, optionally substituted C.sub.1-8 alkyl, optionally substituted C.sub.2-8 alkenyl, optionally substituted C.sub.3-8 alkynyl, optionally substituted C.sub.1-8 alkyl-arbonyl, optionally substituted C.sub.1-6 alkyl-oxalyl, optionally substituted C.sub.1-8 alkoxy-carbonyl, optionally substituted C.sub.1-8 alkoxy-oxalyl, optionally substituted C.sub.3-8 cycloalkyl-carbonyl, optionally substituted C.sub.2-8 alkenyl-carbonyl or optionally substituted benzoyl; R.sup.6 is hydrogen or halogen; R.sup.7 is hydrogen, halogen or C.sub.Type: GrantFiled: May 10, 1996Date of Patent: June 20, 2000Assignee: Nihon Bayer Agrochem K.K.Inventors: Yoshinori Kitagawa, Katsuaki Wada, Yoshiko Kyo, Yuichi Otsu, Yumi Hattori, Toru Obinata, Takahisa Abe, Katsuhiko Shibuya, Wolfram Andersch
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Patent number: 5894073Abstract: According to the present invention, provided are(1) a process for the preparation of 2-chloro-5-chloromethyl-1,3-thiazole, by reacting 3-chloro-1-isothiocyanato-1-propene with a chlorinating agent,(2) a process for the preparation of 3-chloro-1-isocyanato-1-propene, by rearranging 3-chloro-1-thiocyanato-2-propene in the presence of a salt of one or more than one metal selected from the group consisting of metals belonging to Group 2A, Group 7A, Group 8 and Group 1B of the long-form periodic table, and(3) a process for the preparation of 3-chloro-1-thiocyanato-2-propene, by reacting 1,3-dichloropropene and a thiocyanate salt(a) in the presence of water,(b) in the presence of an organic solvent which is water-soluble and has a boiling point of 150.degree. C. or lower, or(c) in an organic solvent in the presence of a phase transfer catalyst.Type: GrantFiled: February 21, 1997Date of Patent: April 13, 1999Assignee: Kuraray Co., Ltd.Inventors: Hideki Matsuda, Goro Asanuma, Manzo Shiono
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Patent number: 5726337Abstract: A process for the preparation of a thiocyanate of Formula IIR.sub.f --A.sub.m --(CH.sub.2).sub.n --SCN IIwherein R.sub.f is a C.sub.2 -C.sub.20 perfluoroalkyl radical, or a C.sub.5 -C.sub.38 perfluoroalkyl radical having at least one ether oxygen atom; n is 1 to 3; m is 0 or 1; A is O, S, CO.sub.2, N(R.sub.1)R.sub.2, CON(R.sub.1)R.sub.2, SO.sub.2 N(R.sub.1 R.sub.2 or (OCH.sub.2 CHR.sub.3).sub.a O; wherein a is 3 to about 15; R.sub.1 is H or alkyl radical of 1 to about 4 carbon atoms; R.sub.2 is C.sub.1 -C.sub.12 alkylene; and R.sub.3 is H or CH.sub.2 Cl; said process comprising reacting a fluorinated iodide of Formula IR.sub.f --A.sub.m --(CH.sub.2).sub.n --I Iwherein R.sub.f, A, m and n are as defined above, with a thiocyanate salt M.sup.+ (SCN).sup.- wherein M is sodium or potassium, in the presence of a catalyst comprising a quaternary ammonium salt of formula (R.sub.4).sub.3 (R.sub.5)N.sup.+ Y.sup.-wherein R.sub.4 is butyl; R.sub.5 is methyl or butyl; and Y is Cl, Br, I, or HSO.sub.Type: GrantFiled: December 13, 1996Date of Patent: March 10, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Stephen Ernest Jacobson
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Patent number: 5369104Abstract: Novel compound represented by the formula: ##STR1## wherein X stands for a methine (i.e. the group --CH.dbd.) group or a nitrogen atom; R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, or, taken together, may form a 5- to 7-membered ring combined with the adjacent --C.dbd.C--; R.sup.4 and R.sup.5 respectively stands for a hydrogen atom or an optionally substituted lower alkyl group or, taken together, form a 3- to 7-membered homo- or heterocyclic ring combined with the adjacent carbon atom; A stands for an optionally substituted amino group; m and n denote 1 to 4, respectively, or salts thereof which has an antiallergic, antiinflammatory and anti-PAF activity and is useful as an antiasthmatic agent.Type: GrantFiled: December 28, 1992Date of Patent: November 29, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
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Patent number: 5227509Abstract: A method for preparing (R)X.sub.m-p A.sub.p by reacting (R)X.sub.m and MA in N-methylpyrrolidone and recovering the by-product MX as a precipitate wherein:X is halide;R contains from 1 to 8 carbon atoms, can be substituted or unsubstituted, and is straight or branched chain alkyl, cycloaliphatic, aralkyl, alkylene, alkenyl, alkenylene, alkynyl or alkynylene with the proviso that X is not attached to a carbon atom having a double bond;A.sup.- is a monovalent anion soft base selected from the group consisting of halide different from X, SCN.sup.-, SH.sup.-, SO.sub.3 H.sup.-, R.sub.2 PO.sub.4.sup.-, PF.sub.6.sup.-, and [SP(Z) (OR.sup.1).sub.2 ].sup.- wherein R.sup.1 is lower alkyl and z i sulfur or oxygen;M is an alkali metal or NH.sub.4.sup.+ ;m is an integer from 1 to 3 with the proviso that m is 1 or 2 when R has one carton; andP is an integer from 1 to m.Type: GrantFiled: May 7, 1990Date of Patent: July 13, 1993Assignee: ISP Investments Inc.Inventors: Kolazi S. Narayanan, Paul D. Taylor
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Patent number: 5145850Abstract: An imidazo [1,2-b]pyridazine compound of the formula (I): ##STR1## wherein R.sub.1 is a halogen atom or a lower alkyl group optionally having substituent(s), R.sub.2 and R.sub.3 are, independently, a hydrogen atom, a lower alkyl group optionally having substituent(s), a cycloalkyl group or a phenyl group optionally having substituent(s) or R.sub.2 and R.sub.3 together with the adjacent nitrogen atom to which they bond may form a heterolcyclic ring optionally having substituent(s), X is an oxygen atom or S(O).sub.k (k is zero to two), a group --.circle.A-- is a bivalent three to seven membered homocyclic or heterocyclic group optionally having substituent(s), m.sup.1 and m.sup.2 each is an integer of 0 to 4 and n is an integer of 0 or 1; or its salt, which is useful as antiasthmatics.Type: GrantFiled: February 25, 1991Date of Patent: September 8, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Yasuko Ashida
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Patent number: 4994495Abstract: Fungicidal compounds having the formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is optionally substituted C.sub.2-10 alkenyl, optionally substituted C.sub.5-6 cycloalkenyl, optionally substituted C.sub.2-10 alkynyl, or C.sub.1-10 alkyl substituted with --CN, --NC, --COR.sup.2, --CO.sub.2 R.sup.2, --NO.sub.2 or --SCN; X is O, S(O)n or NR.sup.2 and is attached to the 3- or the 4-position of the phenyl ring; Y and Z, which may be the same or different, are H, halogen, --CH.sub.3, --C.sub.2 H.sub.5, or --OCH.sub.3 ; R.sup.2 is H, C.sub.1-4 alkyl, C.sub.1-4 alkenyl, or, when R.sup.2 is C.sub.1-4 alkyl in the group --COR.sup.2, it joins with the alkyl group to which --COR.sup.2 is attached to form a 5- or 6-membered aliphatic ring; and n is 0, 1 or 2.Type: GrantFiled: May 11, 1989Date of Patent: February 19, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Michael G. Hutchings, Ian Ferguson
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Patent number: 4962123Abstract: A halogenated ethylene compound of the formula:X CR.sub.1 R.sub.2 C(Y.sub.1).dbd.C(Y.sub.2)CR.sub.1 R.sub.2 SCNwhere R.sub.1 and R.sub.2 are hydrogen, optionally substituted alkyl or together form a cyclohexyl group; X is bromine, chlorine or iodine and Y.sub.1 and Y.sub.2 are chlorine, bromine or iodine. A compound of this type is 2,3-dibromo-1-chloro-4-thiocyanato-2-butene. The compound has good anti-fungal and anti-bacterial properties. The compound can be used as an industrial biocide.Type: GrantFiled: August 29, 1988Date of Patent: October 9, 1990Assignee: Imperial Chemical Industries PLCInventor: Peter W. Austin
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Patent number: 4879249Abstract: Novel immunoassay which utilizes an enzyme linked ligand or receptor wherein the enzyme is bacterial luciferase; mercantile kit useful in performing said immunoassay; and compounds utilized in performing said assay.Type: GrantFiled: March 17, 1986Date of Patent: November 7, 1989Inventors: Thomas O. Baldwin, Thomas F. Holzman, Paul S. Satoh, Frederick S. Yein