Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Reexamination Certificate
2007-08-06
2010-06-01
Shiao, Rei-tsang (Department: 1628)
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
Reexamination Certificate
active
07728163
ABSTRACT:
A surfactant of formula 1in-line-formulae description="In-line Formulae" end="lead"?(Rf-A)a-Q-([B]k—R)b Formula 1in-line-formulae description="In-line Formulae" end="tail"?whereina and b are each independently 1 or 2;Rfis a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen;R is a C1to C20linear, branched or cyclic alkyl, or a C6to C10aryl;B is —(CH2CHR1O)x—,k is 0 or 1, x is 1 to about 20,A is —(CH2)m[(CHR1CH2O)]s—[(CH2)m(CH)tCHOH(CH2)m]e—,whereineach m is independently 0 to 3, s is 0 to about 30, t is 0 or 1, and e is 0 or 1,R1is H or CH3,Q is:—OP(O)(O−M+)(O)—,—O—,—S—(CH2)m—C(O)—O—,—SO2—O——CH2CH2O—C(O)CH2C(OH)(V)CH2C(O)O—;—(CH2CH2O)xCH2CH(OH)—(CH2CH2O)x—(CH2)m—Si[OSi(R2)3]2—, —SO2NR2—,—(CH2CH2O)zC(O)CH(SO3−M+)CH2C(O)(OCH2CH2)z—wherein z is 1 to about 15, ora bond when s is a positive integer,V is —C(O)OR3and R3is H, CH3or Rf;R2is C1to C4alkyl, andM+is a Group 1 metal or an ammonium (NHxR2y)+cation wherein x+y=4, and R2is C1to C4alkyl,provided that when Q is —OP(O)(O−M+)(O)— or when Q is —(CH2CH2O)z—C(O)CH(SO3−M+)CH2C(O)(OCH2CH2)z—, then at least one of s or e is a positive integer.
REFERENCES:
patent: 3128272 (1964-04-01), Wear et al.
patent: 3719698 (1973-03-01), Tesoro et al.
patent: 4296034 (1981-10-01), Bouvet et al.
patent: 5502251 (1996-03-01), Pohmer et al.
patent: 5608116 (1997-03-01), Halling et al.
patent: 6060626 (2000-05-01), Fujii et al.
patent: 6180740 (2001-01-01), Fitzgerald
patent: 6451717 (2002-09-01), Fitzgerald et al.
patent: 6506806 (2003-01-01), Taylor et al.
patent: 6979711 (2005-12-01), Franchina
patent: 7164041 (2007-01-01), Moore et al.
patent: 7553985 (2009-06-01), Shtarov et al.
patent: 2004/0138080 (2004-07-01), DeSimone et al.
patent: 2005/0107645 (2005-05-01), Furukawa
patent: 2005/0197273 (2005-09-01), Savu et al.
patent: 2006/0148671 (2006-07-01), Dams et al.
patent: 2007/0049646 (2007-03-01), Moore et al.
patent: 0150942 (1985-08-01), None
patent: 0164124 (1985-12-01), None
patent: 1462434 (2004-09-01), None
patent: 1496073 (2005-01-01), None
patent: 1505098 (2005-02-01), None
patent: 2797764 (2001-03-01), None
patent: 1372037 (1974-10-01), None
patent: 61291677 (1986-12-01), None
patent: 04080282 (1992-03-01), None
patent: 08208425 (1996-08-01), None
patent: 2003131334 (2003-05-01), None
patent: 2004161838 (2004-06-01), None
patent: 2005054020 (2005-03-01), None
patent: WO 02/26921 (2002-04-01), None
patent: WO 2004067579 (2004-08-01), None
patent: WO 2005/113488 (2005-01-01), None
patent: WO2008/070490 (2008-06-01), None
Shtarov et al, 2007, CAS: 146:464128.
Yoshino et al., 2005, CAS: 144:56985.
Stone et al., 2004, CAS: 140:255324.
Keiper et al: “New Phosphate Fluorosurfactants for Carbon Dioxide” J. Am. Chem. Soc., vol. 124, No. 9, 2002, pp. 1834-1835, XP002499301 compound 2, figures 1-3, p. 1835, col. 2, line 1-line 8.
Keiper at al: “Self-Assembly of Phosphate Fluorosurfactants in Carbon Dioxide”, Langmuir, 20(4), 1065-1072 CODEN: LANGD5; ISSN: 0743-7463, 2004, XP002499490 Abstract, compounds 5-13.
Selve Claude et al: “Synthesis of monodisperse perfluoroalkyl oxyethylene surfactants with methoxy capping: surfactants of high chemical inertness”, Journal of The Chemical Society, Chemical Communications, Chemical Society. Letchworth, GB, Jan. 1, 1990, pp. 911-912, XP009112323.
Burger-Guerrisi et al: Research Article Temperature-induced phase transitions in fluorinated microemulsions: correlations between kinetics and structural observations:, J. Phys. Chem., vol. 92, No. 17, 1988, pp. 4974-4979, XP002520241, Abstract.
Tamura et al: “New Syntetic Method of Alky Perfluoroalkyl Ethers”, SYNLETT, 2000, pp. 343-344, XP002520242.
Lehmler et al: “Synthesis and Structure of Environmentally Relevant Perfluorinated Sulfonamides”, J. Fluorine Chem., vol. 128, Feb. 6, 2007, pp. 595-607, XP002520454, p. 595, col. 1, line 5.
Benefice-Malouet et al: J. Fluorine Chem., vol. 31, 1986, pp. 319-332, XP002520455.
Fujii et al: “A Convenient Catalytic Method for the Synthesis of Ethers from Alcohols and Carbonyl Compounds”, Bull. Chem. Soc. Jpn., vol. 78, 2005, pp. 456-463, XP002520463.
Kumitake et al., Bilayer Membranes of Triple-Chain, Fluorocarbon Amphiphiles; J. Am. Chem. Soc. (1985), 107, 692-696.
Abenin et al., Synthèse de 3-[2F-alkyléthylamino]-1,2-époxypropanes et obtention de nouveaux tensioactifs mono ou bicaténaires à tête β-hydroxylée; J. of Fluorine Chemistry (1991), 55, 1-11. Abstract.
Guo et al. , Hybrid Surfactants Containing Separate Hydrocarbon and Fluorocarbon Chains; Journal of Physical Chemistry (1992), 96(16), 6738-6742.
Guo et al. , Exchange of Hybrid Surfactant Molecules Between Monomers and Micelles; Journal of Physical Chemistry (1992), 96(24), 10068-74.
Harrison et al., Water-in-Carbon Dioxide Microemulsions with a Fluorocarbon-Hydrocarbon Hybrid Surfactant; Langmuir (1994), 10, 3436-3541.
Myrtil et al., Double-tailed perfluoroalkyl telomeric surfactants derived from tris(hydroxymethyl)acrylamidomethane for medical applications; Macromol. Chem. Phys. (1994), 195, 1289-1304.
Yoshino et al., Surfactants having polyfluoroalkyl chains. II. Syntheses of anionic surfactants having two polyfluoroalkyl chains including a trifluoromethyl group at each tail and their flocculation-redispersion ability for dispersed magnetite particles in water; J. of Fluorine Chemistry (1995), 70, 187-191.
Yoshino et al., Syntheses of Hybrid Anionic Surfactants Containing Fluorocarbon and Hydrocarbon Chains; Langmuir (1995), 11(2), 466-469.
Ito et al., Micellar Solution Properties of Fluorocarbon-Hydrocarbon Hybrid Surfactants; Langmuir (1996), 12(24), 5768-5772.
Církva et al., Chemistry of [(perfluoroalkyl)methyl] oxiranes. Regioselectivity of ring opening with O-nucleophiles and the preparation of amphiphilic monomers; Journal of Fluorine Chemistry (1997) 84, 54-61.
Ito et al., Micelle Aggregating Condition of Fluorocarbon-Hydrocarbon Hybrid Surfactants in Aqueous Solution; Langmuir (1997), 13, 2935-2942.
Abe, Synthesis and applications of surfactants containing fluorine; Current Opinion in Colloid & Interface Science (1999) 4, 354-356.
Huc et al., Gemini surfactants: studying micellisation by1H and19F NMR spectroscopy; Chem Comm, Sep. 1, 1999.
Abe et al., Fluorocarbon Hybrid Surfactants Characterization of Admicelles and Its Solubilization; Ind. Eng. Chem. Res. (2000), 39, 2697-2703.
Oda et al., Aggregation Properties and Mixing Behavior of Hydrocarbon, Fluorocarbon, and Hybrid Hydrocarbon-Fluorocarbon Cationic Dimeric Surfactants; Langmuir (2000), 16, 9759-9769.
Saeki et al., Solubilization of Oily Compounds into Fluorocarbon-Hydrocarbon Hybrid Surfactant Admicelles Formed on Alumina Surfaces; Langmuir (2000), 16(26), 9991-9995.
Chevalier, New surfactants: new chemical functions and molecular architectures; Current Opinion in Colloid & Interface Science (2002), 7, 3-11.
Timperley et al., Fluorinated phosphorus compounds Part 6. The synthesis of bis(fluoroalkyl) phosphites and bis(fluoroalkyl) phosphorohalidates; J. of Fluorine Chemistry (2002), 113, 65-78.
Aydogan et al., Interfacial and Bulk Properties of the New Fluorocarbon-Hydrocarbon Hybrid Unsymmetrical Bolaform Surfactant; Langmuir (2003), 19(26), 10726-10731.
Kirmizialtin et al., New Surfactants design for CO2applications: Molecular dynamics simulations of fluorocarbon-hydrocarbon oligomersa); J. of Chemical Physics (2003), 119(9), 4953-4961.
Dupont et al., Hybrid Fluorocarbon-Hydrocarbon CO2-philic Surfactants. 1. Synthesis and Properties of Aqueous Solutions; Langmuir (2004), 20, 9953-9959.
Genson et al., Interfacial Micellar Structures from Novel Amphiphilic Star Polymers; Langmuir (2004), 20,
Acosta Erick Jose
Michalczyk Michael Joseph
Taylor Charles Kenneth
E.I. du Pont de Nemours and Company
Shiao Rei-tsang
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