Sulfur Or Halogen Attached Indirectly To The Thiocyano Group By Acyclic Nonionic Bonding Patents (Class 558/15)
  • Patent number: 8212064
    Abstract: 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: Grant
    Filed: May 14, 2008
    Date of Patent: July 3, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
  • Patent number: 8153846
    Abstract: 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: Grant
    Filed: November 18, 2008
    Date of Patent: April 10, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Axel Hans-Joachim Herzog, Hollis Thomas Warren, Brent Ryan Gonska
  • Publication number: 20090287010
    Abstract: 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: Application
    Filed: May 14, 2008
    Publication date: November 19, 2009
    Applicant: E.I. du Pont de Nemours and Company
    Inventors: Weiming Qiu, Anilkumar Raghavanpillai, Michael Francis Vincent
  • Patent number: 7393961
    Abstract: (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: Grant
    Filed: March 8, 2005
    Date of Patent: July 1, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 6222057
    Abstract: 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: Grant
    Filed: April 7, 2000
    Date of Patent: April 24, 2001
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideki Matsuda, Goro Asanuma, Manzo Shiono
  • Patent number: 6103921
    Abstract: 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: Grant
    Filed: January 5, 1999
    Date of Patent: August 15, 2000
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideki Matsuda, Goro Asanuma, Manzo Shiono
  • Patent number: 6077866
    Abstract: 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: Grant
    Filed: May 10, 1996
    Date of Patent: June 20, 2000
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Yoshinori Kitagawa, Katsuaki Wada, Yoshiko Kyo, Yuichi Otsu, Yumi Hattori, Toru Obinata, Takahisa Abe, Katsuhiko Shibuya, Wolfram Andersch
  • Patent number: 5894073
    Abstract: 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: Grant
    Filed: February 21, 1997
    Date of Patent: April 13, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideki Matsuda, Goro Asanuma, Manzo Shiono
  • Patent number: 5726337
    Abstract: 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: Grant
    Filed: December 13, 1996
    Date of Patent: March 10, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Stephen Ernest Jacobson
  • Patent number: 5369104
    Abstract: 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: Grant
    Filed: December 28, 1992
    Date of Patent: November 29, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5227509
    Abstract: 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: Grant
    Filed: May 7, 1990
    Date of Patent: July 13, 1993
    Assignee: ISP Investments Inc.
    Inventors: Kolazi S. Narayanan, Paul D. Taylor
  • Patent number: 5145850
    Abstract: 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: Grant
    Filed: February 25, 1991
    Date of Patent: September 8, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuko Ashida
  • Patent number: 4994495
    Abstract: 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: Grant
    Filed: May 11, 1989
    Date of Patent: February 19, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Michael G. Hutchings, Ian Ferguson
  • Patent number: 4962123
    Abstract: 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: Grant
    Filed: August 29, 1988
    Date of Patent: October 9, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Peter W. Austin
  • Patent number: 4879249
    Abstract: 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: Grant
    Filed: March 17, 1986
    Date of Patent: November 7, 1989
    Inventors: Thomas O. Baldwin, Thomas F. Holzman, Paul S. Satoh, Frederick S. Yein