WO2018162554A1 - Solvant biodégradable - Google Patents

Solvant biodégradable Download PDF

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Publication number
WO2018162554A1
WO2018162554A1 PCT/EP2018/055601 EP2018055601W WO2018162554A1 WO 2018162554 A1 WO2018162554 A1 WO 2018162554A1 EP 2018055601 W EP2018055601 W EP 2018055601W WO 2018162554 A1 WO2018162554 A1 WO 2018162554A1
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composition
organic solvent
alkyl
solubility parameter
hansen
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PCT/EP2018/055601
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English (en)
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Henning Urch
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/11—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids from solid polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/095—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/096—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D127/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers
    • C09D127/02—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D127/04—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C09D127/06—Homopolymers or copolymers of vinyl chloride
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02—Homopolymers or copolymers of hydrocarbons
    • C08J2325/04—Homopolymers or copolymers of styrene
    • C08J2325/08—Copolymers of styrene
    • C08J2325/12—Copolymers of styrene with unsaturated nitriles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08J2327/06—Homopolymers or copolymers of vinyl chloride
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers

Definitions

  • the present invention refers to a composition
  • a composition comprising a) from 1 to 60 wt.-%, based on the total weight of the composition, of at least one polymeric resin, and b) from 40 to 99 wt.-%, based on the total weight of the composition, of an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0, and the use of an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 as biodegradable solvent as well as the use of the composition in the manufacturing process of enameled copper wires.
  • Organic solvents such as N-methylpyrrolidone (NMP), N-ethyl-2-pyrrolidone (NEP), N,N- dimethyl acetamide (DMAc), dimethyl formamide (DMF) and the like, are considered as common and important solvents in many applications, e.g. in the manufacturing of enemaled copper wires, polyurethane coatings, paint strippers, and agricultural chemical formulations. These solvents are usually highly polar, aprotic organic solvents having a low viscosity and are easily miscible with water and other organic solvents.
  • NMP N-methylpyrrolidone
  • NEP N-ethyl-2-pyrrolidone
  • DMAc ⁇ , ⁇ -dimethyl acetamide
  • DMF dimethyl formamide
  • enameled copper wires is to provide organic solvents having an improved solubility for the polymeric resins used, e.g. for polyamidimide, polyurethane, poly(styrene-co-acrylnitrile), polyvinylchloride, polyamide, polyalkylenetherephthalate and the like.
  • organic solvents suitable for solubilizing polymeric resins such as polyamidimide, polyurethane, poly(styrene-co-acrylnitrile), polyvinylchloride, polyamide, polyalkylenetherephthalate and the like. Accordingly, it is an object of the present invention to provide an organic solvent. Furthermore, it is an object of the present invention to provide a solvent which is biodegradable. It is an even further object of the present invention to provide a solvent that has an excellent solubility for polymeric resins such as polyamidimide, polyurethane, poly(styrene-co-acrylnitrile),
  • polyvinylchloride polyamide, polyalkylenetherephthalate and the like.
  • a composition comprising a) from 1 to 60 wt.-%, based on the total weight of the composition, of at least one polymeric resin, and b) from 40 to 99 wt.-%, based on the total weight of the composition, of an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 shows excellent solubility for polymeric resins and thus can be used as organic solvent for such resins. Furthermore, organic solvents having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 are based on renewable resources, and thus are biodegradable, and further do not cause health and/or environmental concerns.
  • the use of an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 as defined herein, as biodegradable solvent is provided.
  • the organic solvent is used as dissolution agent, cleaning agent, dilution agent, extraction agent, absorption agent, reaction medium, stripping agent, removing agent, degreasing agent and/or dispersion agent for at least one polymeric resin selected from the group comprising polyamidimide, polyurethane, poly(styrene-co-acrylnitrile), polyvinylchloride, polyamide, polyalkylenetherephthalate and mixtures thereof.
  • composition comprising two or more compounds of the general formula (I), as defined herein, as surfactant.
  • composition comprising two or more compounds of the general formula (I), as defined herein, is used as surfactant in a laundry process.
  • the composition comprises from 1 to 40 wt.-%, based on the total weight of the composition, of the at least one polymeric resin and from 60 to 99 wt.-%, based on the total weight of the composition, of the organic solvent.
  • the at least one polymeric resin is selected from the group comprising polyamidimide, polyurethane, poly(styrene-co-acrylnitrile), polyvinylchloride, polyamide, polyalkylenetherephthalate and mixtures thereof, preferably the at least one polymeric resin is selected from the group comprising polyamidimide, polyurethane,
  • the organic solvent further has i) a Hansen dispersion solubility parameter 5 D of greater than 16.8, and i) a Hansen polar solubility parameter ⁇ ⁇ of greater than 7.0.
  • the organic solvent has i) a Hansen hydrogen bonding solubility parameter ⁇ ⁇ in the range from 1 1.0 to 28.0, more preferably from 12.0 to 24.0, ii) a Hansen dispersion solubility parameter 5 D in the range from 16.8 to 24.0, more preferably from 16.9 to 21.0 and iii) a Hansen polar solubility parameter ⁇ ⁇ in the range from 7.0 to 17.0, more preferably from 9.0 to 14.0.
  • the organic solvent is a compound according to formula (I)
  • R 1 and R 2 are independently selected from C1 to C6 alkyl, R 3 is selected from H or C1 to C4 alkyl, R 4 is selected from H or C1 to C8 alkyl.
  • R 1 and R 2 and R 3 in formula (I) are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is selected from H or C1 to C8 alkyl.
  • R 1 and R 2 in formula (I) are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is selected from H or C1 to C8 alkyl.
  • R 1 and R 2 and R 3 in formula (I) are the same.
  • the organic solvent is selected from the group comprising ⁇ , ⁇ -dimethyl lactamide, ⁇ , ⁇ -diethyl lactamide, N,N-dimethyl-2-hydroxybutanoic amide, N,N- diethyl-2- hydroxybutanoic amide, C1 to C8 ester of N,N-diethyl-2- hydroxybutanoic amide and mixtures thereof.
  • the organic solvent is selected from ⁇ , ⁇ -dimethyl lactamide and ⁇ , ⁇ -diethyl lactamide, preferably ⁇ , ⁇ -dimethyl lactamide.
  • the composition is free of water or water vapor and/or additives selected from polyvinylpyrrolidone, polyalkylene oxides such as polyethylene oxide, polypropylene oxide and polyethyleneoxide/polypropylene oxide block copolymers.
  • inventive composition comprising at least one polymeric resin, and an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 will be described in more detail. It is to be understood that these technical details and embodiments also apply to the inventive uses.
  • a composition comprising a) from 1 to 60 wt.-%, based on the total weight of the composition, of at least one polymeric resin, and b) from 40 to 99 wt.-%, based on the total weight of the composition, of an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 is provided. It was surprisingly found out by the inventors that a composition comprising an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 shows excellent solubility for polymeric resins and thus can be used as solvent for such resins.
  • organic solvents Due to the excellent solubility of such organic solvent for polymeric resins, the corresponding compositions can be advantageously used in the manufacturing process of enameled copper wires.
  • organic solvents are biodegradable and do not cause health and/or environmental concerns.
  • one essential component of the composition is the at least one polymeric resin.
  • the term "at least one" means that the polymeric resin comprises, preferably consists of, one or more polymeric resin(s).
  • the at least one polymeric resin comprises, preferably consists of, one polymeric resin.
  • the at least one polymeric resin comprises, preferably consists of, two or more polymeric resins.
  • the at least one polymeric resin comprises, preferably consists of, two or three polymeric resins.
  • the at least one polymeric resin comprises, preferably consists of, a mixture of different polymeric resins.
  • the mixture comprises, preferably consists of, two to five polymeric resins.
  • the mixture of polymeric resins comprises, preferably consists of, two or three polymeric resins.
  • Suitable polymeric resins are in principle all polymers that are suitable for making enameled copper wires.
  • the at least one polymeric resin is selected from the group comprising polyamidimide, polyurethane, poly(styrene-co-acrylnitrile), polyvinylchloride, polyamide, polyalkylenetherephthalate and mixtures thereof.
  • the at least one polymeric resin is selected from the group comprising
  • polyamidimide polyurethane, poly(styrene-co-acrylnitrile), polyvinylchloride and mixtures thereof.
  • the at least one polymeric resin is selected from the group comprising polyamidimide, polyurethane, poly(styrene-co-acrylnitrile) and polyvinylchloride.
  • the at least one polymeric resin is polyamidimide or polyurethane.
  • the at least one polymeric resin is poly(styrene-co-acrylnitrile) or polyvinylchloride.
  • the at least one polymeric resin is polyamidimide.
  • the polyamidimide being the at least one polymeric resin is preferably selected from aromatic, aromatic/aliphatic and aliphatic polyamidimides.
  • the polyamidimide is selected from aromatic and aliphatic polyamidimides.
  • the polyamidimide is an aromatic polyamidimide.
  • aromatic polyamidimide refers to polyamidimide in which the individual structural components are made of aromatic compounds. That is to say, the "aromatic polyamidimide” consists of individual structural components that are made of aromatic compounds.
  • aliphatic polyamidimide refers to polyamidimide in which the individual structural components are made of aliphatic compounds. That is to say, the “aliphatic polyamidimide” consists of individual structural components that are made of aliphatic compounds.
  • aromatic/aliphatic polyamidimide refers to polyamidimide in which the individual structural components are made of aromatic and aliphatic compounds. That is to say, the “aromatic/aliphatic polyamidimide” consists of individual structural components that are made of aromatic and aliphatic compounds.
  • Polyamidimides are prepared by a great variety of methods, which are well known in the art.
  • the polyamidimides can be prepared by a direct polymerization method as described in US 5,532,334 A which comprises the direct polymerization of an aromatic diamine (such as MDI, TDI or HDMI) with an aromatic tricarboxylic acid anhydride in the presence of dehydration catalyst as disclosed in U.S. Pat. No. 3,860,559 and Japanese Patent Publication No. SHO 58- 180532.
  • the documents are thus incorporated herewith by reference.
  • the polyamidimide is preferably prepared from an aromatic diamine selected from the group comprising m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylsulfon, 4,4'-diaminodiphenylmethane, 4,4'-diaminodipheylsulfide, 4-methyl-1 ,3-diaminobenzene, 4,4'- diaminodiphenylmethane, 3,4'-diaminodiphenylether, 3,3'-dichloro-4,4'- diaminodiphenylmethane, 3,3'-dimethoxy-4,4'-diaminodiphenylmethane, m-bis(p- aminophenoxy)benzene, p-bis(p-aminophenoxy)benzene, m-xylenediamine and mixtures thereof, and an aromatic tricarboxylic acid anhydride selected from an aromatic
  • aromatic tricarboxylic acid derivative may be suitable as the aromatic tricarboxylic acid anhydride.
  • suitable aromatic tricarboxylic acid derivatives include an ester of trimellitic acid anhydride with alcohol, for example trimellitic acid monoester compounds such as trimellitic acid monomethyl ester and trimellitic acid monoethyl ester.
  • Polymeric resins e.g. polyamidimide, polyurethane, poly(styrene-co-acrylnitrile),
  • polyvinylchloride polyamide, polyalkylenetherephthalate and mixtures thereof, are well known to those skilled in the art and thus a further detailed description thereof is not necessary.
  • the composition comprises from 1 to 60 wt.-%, based on the total weight of the composition, of the at least one polymeric resin. In one embodiment, the composition comprises from 1 to 40 wt.-%, based on the total weight of the composition, of the at least one polymeric resin. For example, the composition comprises from 2 to 35 wt.-%, based on the total weight of the composition, of the at least one polymeric resin.
  • Another essential component of the composition is the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0.
  • the composition comprises from 40 to 99 wt.-%, based on the total weight of the composition, of the organic solvent.
  • the composition comprises from 60 to 99 wt.-%, based on the total weight of the composition, of the organic solvent.
  • the composition comprises from 65 to 98 wt.-%, based on the total weight of the composition, of the organic solvent.
  • the composition comprises from 1 to 60 wt.-%, based on the total weight of the composition, of at least one polymeric resin, and from 40 to 99 wt.-%, based on the total weight of the composition, of the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • the composition comprises from 1 to 40 wt.-%, based on the total weight of the composition, of the at least one polymeric resin, and from 60 to 99 wt.-%, based on the total weight of the composition, of the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0. More preferably, the composition comprises from 2 to 35 wt.-%, based on the total weight of the composition, of the at least one polymeric resin, and from 65 to 98 wt.-%, based on the total weight of the composition, of the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • the composition consists of the at least one polymeric resin and the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • the composition consists of 1 to 60 wt.-%, based on the total weight of the composition, of the at least one polymeric resin, and from 40 to 99 wt.-%, based on the total weight of the composition, of the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • the composition consists of from 1 to 40 wt.-%, based on the total weight of the composition, of the at least one polymeric resin and from 60 to 99 wt.-%, based on the total weight of the composition, of the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0. More preferably the composition consists of from 2 to 35 wt.- %, based on the total weight of the composition, of the at least one polymeric resin and from 65 to 98 wt.-%, based on the total weight of the composition, of the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 comprises one or more co-sol vent(s). If the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 comprises one or more co-solvent(s), the one or more co-solvent(s) is/are present in an amount of up to 20 wt.-%, based on the total weight of the organic solvent and co-solvent(s).
  • the organic solvent comprises the one or more co-solvent(s) in an amount from 1 to 20 wt.-%, preferably from 1 to 15 wt.-% and most preferably from 1 to 12 wt.-%, based on the total weight of the organic solvent and co-sol vent(s).
  • the weight ratio of the organic solvent to the one or more co-solvent(s) [organic solvent:co-solvent] is typically from 99:1 to 80:20, preferably from 99:1 to 85:15 and most preferably from 99:1 to 88:12.
  • the organic solvent comprises the one or more co-solvent(s) preferably in an amount of ⁇ 10 wt.-%, more preferably of ⁇ 8 wt.-%, and most preferably of ⁇ 5 wt.-%, based on the total weight of the organic solvent and co-solvent(s).
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 comprises one co-solvent.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 comprises two or three co-solvents.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 comprises one co-solvent.
  • the one or more co-solvent(s), if present, is/are an organic solvent differing from the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0.
  • the one or more co-solvent(s), if present, has/have a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of ⁇ 1 1.0.
  • the one or more co-solvent(s), if present, is/are preferably selected from the group consisting of N-methylpyrrolidone, N,N-dimethylacetamide, ⁇ -butyrolactone, xylene, solvent naphtha and alcohols, preferably divalent alcohols or trivalent alcohols.
  • Suitable alcohols include n-butanol, sec.-butanol, iso-butanol, n-pentanol, sec.-pentanol, iso-pentanol, 1 ,2-ethanediol, ethylene glycol, diethylene glycol, triethylene glycol, propyleneglycol, dipropyleneglycol, glycerol, neopentylglycol, 1 ,4-butanediol and/or 1 ,5-pentanediol.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 is free of one or more co-solvent(s).
  • the organic solvent may further comprise a polymerization inhibitor. Suitable polymerization inhibitor are selected from the group comprising benzene, methanol, methanol, ethanol, isobutanol, phosphoric acid and mixtures thereof.
  • the organic solvent is characterized in that it shows an excellent solubility for the at least one polymeric resin. It is thus required that the organic solvent has a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0.
  • the Hansen hydrogen bonding solubility parameter ⁇ ⁇ , the Hansen dispersion solubility parameter ⁇ 0 as well as the Hansen polar solubility parameter ⁇ ⁇ are determined in accordance with the method described in Amol Shivajirao Hukkerikar et.al., Fluid Phase Equilibria 321 (2012) 25-43.
  • the Hansen solubility parameters are described in standard textbooks such as Hansen Solubility Parameters: A User's Handbook, C. M. Hansen, 2007, 2 nd Edition.
  • a modelling software such as HSPI P 3.1 .14 (3rd Edition) of CM. Hansen or Propred 4.4 can be used.
  • Hansen solubility parameters described in the present application refer to the solubility at room temperature, i.e. at about 23 °C.
  • the organic solvent has a Hansen hydrogen bonding solubility parameter ⁇ ⁇ in the range from 1 1.0 to 28.0, more preferably from 12.0 to 24.0.
  • the organic solvent preferably has excellent solubility values with regard to the Hansen dispersion solubility parameter 5 D and the Hansen polar solubility parameter ⁇ ⁇ .
  • the organic solvent thus also has
  • the organic solvent has
  • the organic solvent has
  • a Hansen dispersion solubility parameter ⁇ 0 in the range from 16.8 to 24.0 a Hansen polar solubility parameter ⁇ ⁇ in the range from 7.0 to 17.0.
  • the organic solvent has
  • the organic solvent is preferably an polar aprotic organic solvent.
  • Suitable organic solvents have a boiling point in the range from 80 to 320°C, preferably from 100 to 280°C, and most preferably from 150 to 250°C.
  • the organic solvent is preferably a compound according to formula (I)
  • R 1 and R 2 are independently selected from C1 to C6 alkyl
  • R 3 is selected from H or C1 to C4 alkyl
  • R 4 is selected from H or C1 to C8 alkyl.
  • alkyl is a radical of a saturated aliphatic group. It is appreciated that the term “alkyl” comprises linear and branched alkyl. Preferably, the term “alkyl” refers to linear alkyl.
  • linear is intended to mean that the average number of branching in the alkyl group does not exceed 0.5 and preferably is 0.
  • the expression "branched” means that the average number of branching in the alkyl group exceeds 0.5.
  • the phrase average number of branches refers to the average number of branches per branched alkyl, as measured by 13 C Nuclear Magnetic Resonance ( 13 C NMR). The average number of carbon atoms are determined by gas chromatography.
  • R 1 and R 2 are independently selected from C1 to C4 alkyl. More preferably, R 1 and R 2 are independently selected from C1 to C3 alkyl. For example, R 1 and R 2 are independently C1 or C2 alkyl. It is appreciated that the term "independently" means that the respective substituents are the same or different. For example, if it is stated that R 1 and R 2 (and R 3 ) are independently selected from C1 to C4 alkyl, R 1 and R 2 (and R 3 ) can be the same or different substituent selected from C1 to C4 alkyl. Preferably, R 1 and R 2 are the same.
  • R 1 and R 2 are methyl. In an alternative embodiment, R 1 and R 2 are ethyl.
  • R 3 is methyl. In an alternative embodiment, R 3 is ethyl.
  • R 1 and R 2 and R 3 are preferably independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, Preferably, R 1 and R 2 and R 3 are the same.
  • R 1 and R 2 and R 3 are methyl. In an alternative embodiment, R 1 and R 2 and R 3 are ethyl.
  • R 1 and R 2 are the same and R 3 is different from R 1 and R 2 .
  • R 1 and R 2 are C2 or C3 alkyl and R 3 is C1 alkyl.
  • R 1 and R 2 are C1 alkyl and R 3 is C2 alkyl.
  • R 4 is selected from H or C1 to C8 alkyl.
  • R 4 is H.
  • R 1 and R 2 are independently selected from C1 to C6 alkyl, R 3 is selected from H or C1 to C4 alkyl and R 4 is H.
  • R 1 and R 2 and R 3 are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is H.
  • R 1 and R 2 are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is H.
  • R 1 and R 2 and R 3 are the same, i.e. are selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is H.
  • R 4 is C1 to C8 alkyl.
  • R 4 is C1 to C6 alkyl. More preferably, R 4 is C1 to C4 alkyl.
  • R 4 is methyl
  • R 4 is ethyl
  • R 4 is propyl
  • R 4 is butyl
  • R 1 and R 2 are independently selected from C1 to C6 alkyl
  • R 3 is selected from H or C1 to C4 alkyl
  • R 4 is C1 to C8 alkyl.
  • R 4 is C1 to C6 alkyl. More preferably, R 4 is C1 to C4 alkyl.
  • R 1 and R 2 and R 3 are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is C1 to C8 alkyl.
  • R 4 is C1 to C6 alkyl. More preferably, R 4 is C1 to C4 alkyl.
  • R 1 and R 2 are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is C1 to C8 alkyl.
  • R 4 is C1 to C6 alkyl. More preferably, R 4 is C1 to C4 alkyl.
  • R 1 and R 2 and R 3 are the same, i.e. are selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is C1 to C8 alkyl.
  • R 4 is C1 to C6 alkyl. More preferably, R 4 is C1 to C4 alkyl.
  • R 1 and R 2 are independently selected from C1 to C6 alkyl, R 3 is selected from H or C1 to C4 alkyl and R 4 is methyl.
  • R 1 and R 2 and R 3 are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is methyl. More preferably, R 1 and R 2 are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is methyl.
  • R 1 and R 2 and R 3 are the same, i.e. are selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is methyl.
  • R 1 and R 2 are independently selected from C1 to C6 alkyl, R 3 is selected from H or C1 to C4 alkyl and R 4 is ethyl.
  • R 1 and R 2 and R 3 are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is ethyl.
  • R 1 and R 2 are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is ethyl.
  • R 1 and R 2 and R 3 are the same, i.e. are selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is ethyl.
  • R 1 and R 2 are independently selected from C1 to C6 alkyl, R 3 is selected from H or C1 to C4 alkyl and R 4 is propyl.
  • R 1 and R 2 and R 3 are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is propyl.
  • R 1 and R 2 are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is propyl.
  • R 1 and R 2 and R 3 are the same, i.e. are selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is propyl.
  • R 1 and R 2 are independently selected from C1 to C6 alkyl, R 3 is selected from H or C1 to C4 alkyl and R 4 is butyl.
  • R 1 and R 2 and R 3 are independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is butyl. More preferably, R 1 and R 2 are independently selected from C1 to C3 alkyl and R 3 is C1 alkyl, and R 4 is butyl.
  • R 1 and R 2 and R 3 are the same, i.e. are selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl, and R 4 is butyl.
  • the organic solvent is a compound according to formula (II)
  • R 1 and R 2 are independently selected from C1 to C6 alkyl and R 3 is selected from H or C1 to C4 alkyl.
  • R 1 and R 2 are independently selected from C1 to C4 alkyl. More preferably, R 1 and R 2 are independently selected from C1 to C3 alkyl. For example, R 1 and R 2 are independently C1 or C2 alkyl.
  • R 1 and R 2 are the same.
  • R 1 and R 2 are methyl. In an alternative embodiment, R 1 and R 2 are ethyl.
  • R3 is selected from C1 to C4 alkyl. More preferably, R 3 is selected from C1 to C3 alkyl. For example, R 3 is C1 or C2 alkyl.
  • R 3 is methyl. In an alternative embodiment, R 3 is ethyl.
  • R 1 and R 2 and R 3 are preferably independently selected from C1 to C4 alkyl, preferably from C1 to C3 alkyl and most preferably from C1 or C2 alkyl,
  • R 1 and R 2 and R 3 are the same.
  • R 1 and R 2 and R 3 are methyl. In an alternative embodiment, R 1 and R 2 and R 3 are ethyl.
  • R 1 and R 2 are the same and R 3 is different from R 1 and R 2 .
  • R 1 and R 2 are independently C2 or C3 alkyl and R 3 is C1 alkyl.
  • the organic solvent is preferably selected from the group comprising ⁇ , ⁇ -dimethyl lactamide, ⁇ , ⁇ -diethyl lactamide, N,N-dimethyl-2-hydroxybutanoic amide, N,N-diethyl-2- hydroxybutanoic amide, C1 to C8 ester of N,N-diethyl-2- hydroxybutanoic amide and mixtures thereof.
  • the organic solvent is selected from ⁇ , ⁇ -dimethyl lactamide and N,N-diethyl lactamide. More preferably, the organic solvent is ⁇ , ⁇ -dimethyl lactamide.
  • the composition can optionally comprise further additives being typically used in the
  • the composition comprises a friction reducer, such as polysiloxanes, and/or additives increasing the corona resistance, such as fumed silica particles.
  • a friction reducer such as polysiloxanes
  • additives increasing the corona resistance such as fumed silica particles.
  • the composition is free of water or water vapour.
  • composition is free of additives selected from
  • polyvinylpyrrolidone polyalkylene oxides such as polyethylene oxide, polypropylene oxide and polyethyleneoxide/polypropylene oxide block copolymers.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 provides an excellent solubility for the at least one polymeric resin.
  • the composition of the present invention can thus be preferably used in the manufacturing process of enameled copper wires.
  • the present invention refers in a further aspect to the use of a composition as defined herein in the manufacturing process of enameled copper wires.
  • the organic solvent being part of the composition of the present invention does not cause health and/or environmental concerns.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 is based on renewable resources and thus is biodegradable.
  • the present invention refers in a further aspect to the use of an organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1 .0 as defined herein, as biodegradable solvent. Due to the excellent solubility properties, the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 is preferably used as dissolution agent, cleaning agent, dilution agent, extraction agent, absorption agent, reaction medium, stripping agent, removing agent, degreasing agent and/or dispersion agent for at least one polymeric resin selected from the group comprising polyamidimide, polyurethane, poly(styrene-co- acrylnitrile), polyvinylchloride, polyamide, polyalkylenetherephthalate and mixtures thereof.
  • the organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 is preferably used as dissolution agent, cleaning agent, dilution agent, extraction agent, absorption agent, reaction medium,
  • organic solvent having a Hansen hydrogen bonding solubility parameter ⁇ ⁇ of greater than 1 1.0 and preferred embodiments thereof it is referred to the comments provided above when defining said organic solvent and embodiments thereof in more detail.
  • the Hansen hydrogen bonding solubility parameter ⁇ ⁇ , the Hansen dispersion solubility parameter ⁇ 0 as well as the Hansen polar solubility parameter ⁇ ⁇ are set out in Table 1 for the organic solvents of the present invention and solvents of the prior art. Furthermore, the Hansen hydrogen bonding solubility parameter ⁇ ⁇ , the Hansen dispersion solubility parameter ⁇ 0 as well as the Hansen polar solubility parameter ⁇ ⁇ are set out in Table 1 for the organic solvents of the present invention and solvents of the prior art. Furthermore, the Hansen hydrogen bonding solubility parameter ⁇ ⁇ , the Hansen dispersion solubility parameter ⁇ 0 as well as the Hansen polar solubility parameter ⁇ ⁇ are set out in Table 1 for the organic solvents of the present invention and solvents of the prior art. Furthermore, the Hansen hydrogen bonding solubility parameter ⁇ ⁇ , the Hansen dispersion solubility parameter ⁇ 0 as well as the Hansen polar solubility
  • Solubility Parameter is described in Table 1 , which is a vector product of the Hansen hydrogen bonding solubility parameter ⁇ ⁇ , the Hansen dispersion solubility parameter ⁇ 0 as well as the Hansen polar solubility parameter ⁇ ⁇ .
  • Hansen solubility parameters were calculated by using the modelling software Propred 4.4.
  • Hansen solubility parameters described refer to the solubility at room temperature, i.e. at about 23 °C.
  • Table 1 results regarding the Hansen solubility parameters of the inventive (IE) and comparative examples (CE)
  • the organic solvent ⁇ , ⁇ -dimethyl lactamide shows excellent solubility parameters and is thus suitable for use as organic solvent for polymeric resins.
  • the organic solvent ⁇ , ⁇ -dimethyl lactamide is based on renewable resources and thus is readily biodegradable. In addition thereto, the organic solvent ⁇ , ⁇ -dimethyl lactamide does not cause any health and environmental concerns.

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Abstract

La présente invention concerne une composition comprenant a) de 1 à 60 % en poids, par rapport au poids total de la composition, d'au moins une résine polymère, et b) de 40 à 99 % en poids, par rapport au poids total de la composition, d'un solvant organique ayant un paramètre de solubilité de liaison hydrogène de Hansen δΗ supérieur à 11,0, et l'utilisation d'un solvant organique ayant un paramètre de solubilité de liaison hydrogène de Hansen δΗ supérieur à 11,0 en tant que solvant biodégradable, ainsi que l'utilisation de la composition dans le procédé de fabrication de fils de cuivre émaillés.
PCT/EP2018/055601 2017-03-09 2018-03-07 Solvant biodégradable WO2018162554A1 (fr)

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US3393170A (en) * 1966-04-28 1968-07-16 Pennsalt Chemicals Corp Discoloration inhibited amide solutions of vinylidene halide polymers
US3860559A (en) 1973-02-22 1975-01-14 Toray Industries Method of preparing a soluble high molecular weight aromatic polyamide imide composition
JPS58180532A (ja) 1982-04-16 1983-10-22 Sumitomo Chem Co Ltd 芳香族ポリアミドイミドの製造方法
EP0151801A1 (fr) * 1983-12-30 1985-08-21 International Business Machines Corporation Systèmes de solvant à haut point d'inflammation et basse tension superficielle pour revêtements de polyimide
DE4112873A1 (de) * 1991-04-19 1992-10-22 Richard H Dr Sehring Fungicides pflanzenschutzmittel mit wirkung im zierpflanzen und obstbau sowie gegen echten mehltau an getreide, gurken, reben und hopfen
US5532334A (en) 1993-11-12 1996-07-02 Korea Research Institute Of Chemical Technology Process for preparing polyamideimide resins having high molecular weight
WO2007107745A2 (fr) * 2006-03-22 2007-09-27 Syngenta Limited Formulations
WO2008049528A1 (fr) * 2006-10-23 2008-05-02 Cognis Ip Management Gmbh Compositions de polymère
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EP2345702A1 (fr) * 2010-01-13 2011-07-20 Cognis IP Management GmbH Peinture et compositions de décapage
WO2011131272A1 (fr) * 2010-04-22 2011-10-27 Cognis Ip Management Gmbh Compositions de solvant
WO2013107822A1 (fr) * 2012-01-17 2013-07-25 Taminco Utilisation de solvants améliorés de type n-alkyl-pyrrolidone
CN105220520A (zh) * 2015-10-27 2016-01-06 上海华峰超纤材料股份有限公司 无卤革用阻燃聚氨酯树脂浆料及其应用
WO2017045985A1 (fr) * 2015-09-17 2017-03-23 Basf Se Procédé de fabrication de membranes à l'aide de solvants à base de lactame ide

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3393170A (en) * 1966-04-28 1968-07-16 Pennsalt Chemicals Corp Discoloration inhibited amide solutions of vinylidene halide polymers
US3860559A (en) 1973-02-22 1975-01-14 Toray Industries Method of preparing a soluble high molecular weight aromatic polyamide imide composition
JPS58180532A (ja) 1982-04-16 1983-10-22 Sumitomo Chem Co Ltd 芳香族ポリアミドイミドの製造方法
EP0151801A1 (fr) * 1983-12-30 1985-08-21 International Business Machines Corporation Systèmes de solvant à haut point d'inflammation et basse tension superficielle pour revêtements de polyimide
DE4112873A1 (de) * 1991-04-19 1992-10-22 Richard H Dr Sehring Fungicides pflanzenschutzmittel mit wirkung im zierpflanzen und obstbau sowie gegen echten mehltau an getreide, gurken, reben und hopfen
US5532334A (en) 1993-11-12 1996-07-02 Korea Research Institute Of Chemical Technology Process for preparing polyamideimide resins having high molecular weight
WO2007107745A2 (fr) * 2006-03-22 2007-09-27 Syngenta Limited Formulations
WO2008049528A1 (fr) * 2006-10-23 2008-05-02 Cognis Ip Management Gmbh Compositions de polymère
EP2345702A1 (fr) * 2010-01-13 2011-07-20 Cognis IP Management GmbH Peinture et compositions de décapage
WO2011131272A1 (fr) * 2010-04-22 2011-10-27 Cognis Ip Management Gmbh Compositions de solvant
CN101851865A (zh) * 2010-05-31 2010-10-06 上海华峰超纤材料股份有限公司 超细纤维聚氨酯合成革基布及其制备方法
WO2013107822A1 (fr) * 2012-01-17 2013-07-25 Taminco Utilisation de solvants améliorés de type n-alkyl-pyrrolidone
WO2017045985A1 (fr) * 2015-09-17 2017-03-23 Basf Se Procédé de fabrication de membranes à l'aide de solvants à base de lactame ide
CN105220520A (zh) * 2015-10-27 2016-01-06 上海华峰超纤材料股份有限公司 无卤革用阻燃聚氨酯树脂浆料及其应用

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HANSEN; C. M. HANSEN: "Solubility Parameters: A User's Handbook", 2007

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