Abstract: Disclosed is a graft copolymer in which a polyalkylene glycol or an alkyl ether thereof is graft-copolymerized with a polyfluoro-1-alkene represented by the general formula: CnF2n+(CH2CF2)a(CF2CF2)bCH?CH2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3). The graft copolymer is an oligomer compound having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, and having, when used as an active ingredient of a mold-releasing agent, mold release performance equivalent to that of a compound having a perfluoroalkyl group containing 8 or more carbon atoms.

Abstract: Disclosed is a mixture of fluoroolefin iodides represented by the general formulae: CnF2n+1CF2CH?CF(CF2CF2)mI [Ia] and CnF2n+1CF?CHCF2(CF2CF2)mI [Ib] wherein n is an integer of 0 to 5, and m is an integer of 1 to 3. The fluoroolefin iodide mixture is produced by subjecting a fluoroalkyl iodide represented by the general formula: CnF2n+1CF2CH2CF2(CF2CF2)mI [II] wherein n is an integer of 0 to 5, and m is an integer of 1 to 3, to an HF-elimination reaction in the presence of a basic compound.

Abstract: A polyfluoroalkane carboxylic acid represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COOM (M: an alkali metal, a NH4 group or H; n: an integer of 1 to 6; m: an integer of 1 to 4; and l: 1 or 2) can be produced by hydrolysis reaction of polyfluoroalkane carboxylic acid fluoride represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COF, where its carboxylic acid salt can be formed as an alkali metal salt, or a NH4 salt. The polyfluoroalkane carboxylic acid (or its salt) can act as a surfactant having distinguished monomer emulsifiability and latex stability when used as an emulsifying agent or as a dispersing agent for polymerization reaction of fluorine-containing monomers, or as an effective surfactant capable of enhancing the micelles solubility of fluorine-containing monomers such as vinylidene fluoride, etc., when used as an emulsifying agent or a dispersing agent for homopolymerization or copolymerization reaction of vinylidene fluoride.

Abstract: Disclosed is a mold-releasing agent comprising, as active ingredients, a graft copolymer (A) in which a polyalkylene glycol or an alkyl ether thereof is graft-copolymerized with a polyfluoro-1-alkene represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)bCH?CH2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3), and a polyfluoroalkylphosphonic acid represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3, and c is an integer of 1 to 3) or a salt thereof (B). The mold-releasing agent comprises, as an active ingredient, a compound having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, and having mold release performance equivalent to or more than that of a mold-releasing agent comprising a compound having a perfluoroalkyl group containing 8 or more carbon atoms as an active ingredient.

Abstract: A fluorine-containing polyether carboxylic acid amide represented by the general formula: CnF2n+1O(C3F6O)mRfCONHAr, wherein Rf is a fluorocarbon group having 1 to 2 carbon atoms, Ar is a nitrogen-containing heterocyclic group, n is an integer of 1 to 3, and m is an integer of 10 to 30, is produced by reacting a fluorine-containing polyether carboxylic acid fluoride represented by the general formula: CnF2n+1(C3F6O)mRfCOF, wherein Rf, n, and m are as defined above, with a nitrogen-containing heterocyclic amine compound represented by the general formula: ArNH2, wherein Ar is as defined above; wherein the reaction is carried out while a reaction temperature is first increased to 80 to 100° C., and then increased at a temperature increase rate that produces a temperature difference of 3 to 5° C. after 48 hours.

Abstract: Disclosed is a polyfluoroalkylphosphonic acid represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2, wherein n is an integer of 1 to 6, a is an integer of 1 to 4, b is an integer of 1 to 3, and c is an integer of 1 to 3, or a salt thereof, which is a compound having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, and being usable as an active ingredient of a mold-releasing agent. The polyfluoroalkylphosphonic acid is produced by hydrolyzing a polyfluoroalkylphosphonic acid diester represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP (O)(OR)2, wherein R is a C1-C4 alkyl group, n is an integer of 1 to 6, a is an integer of 1 to 4, b is an integer of 1 to 3, and c is an integer of 1 to 3.

Abstract: A polyfluoroalkane carboxylic acid represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COOM (M: an alkali metal, a NH4 group or H; n: an integer of 1 to 6; m: an integer of 1 to 4; and l: 1 or 2) can be produced by hydrolysis reaction of polyfluoroalkane carboxylic acid fluoride represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COF , where its carboxylic acid salt can be formed as an alkali metal salt, or a NH4 salt. The polyfluoroalkane carboxylic acid (or its salt) can act as a surfactant having distinguished monomer emulsificability and latex stability when used as an emulsifying agent or as a dispersing agent for polymerization reaction of fluorine-containing monomers, or as an effective surfactant capable of enhancing the micelles solubility of fluorine-containing monomers such as vinylidene fluoride, etc., when used as an emulsifying agent or a dispersing agent for homopolymerization or copolymerization reaction of vinylidene fluoride.

Abstract: Disclosed is a mixture of fluoroolefin iodides represented by the general formulae: CnF2n+1CF2CH?CF(CF2CF2)mI [Ia] and CnF2n+1CF?CHCF2(CF2CF2)mI [Ib] wherein n is an integer of 0 to 5, and m is an integer of 1 to 3. The fluoroolefin iodide mixture is produced by subjecting a fluoroalkyl iodide represented by the general formula: Cn2n+1CF2CH2CF2(CF2CF2)mI [II] wherein n is an integer of 0 to 5, and m is an integer of 1 to 3, to an HF-elimination reaction in the presence of a basic compound.

Abstract: Disclosed is a peroxide-crosslinkable fluoroelastomer obtained by copolymerization of 0.1 to 20 mol % of a mixture of fluoroolefin iodides represented by the general formulae: CnF2n+1CF2CH?CF(CF2CF2)mI [Ia] and CnF2n+1CF?CHCF2(CF2CF2)mI [Ib], wherein n is an integer of 0 to 5, and m is an integer of 1 to 3. The peroxide-crosslinkable fluoroelastomer is copolymerized with a monomer having a side chain containing a peroxide-crosslinkable halogen atom, and has excellent vulcanizate physical properties and improved compression set characteristics when subjected to peroxide crosslinking.

Abstract: A polyfluoro-1-alkene represented by the general formula: CF3(CF2)nCH2(CF2)mCH?CH2 [I], wherein n is an integer of 0 to 5, and m is an integer of 1 to 7, is produced by reacting a polyfluoroalkyl iodide represented by the general formula: CF3(CF2)nCH2(CF2)m(CH2CH2)I [II], wherein n is an integer of 0 to 5, and m is an integer of 1 to 7, with an inorganic basic compound in the presence of a phase transfer catalyst. Alternatively, the polyfluoro-1-alkene is produced by reacting the polyfluoroalkyl iodide [II] with a nitrogen-containing organic basic compound, and is obtained product [I] as one fraction thereof. By the copolymerization of the polyfluoro-1-alkene with other fluorinated olefin monomers, a fluorine-containing copolymer having excellent light transmittance in the visible light range is formed.

Abstract: A mixture of polyfluoroalkadienes represented by the general formulae: CF3(CF2)nCF?CH(CF2)m+1CH?CH2 [Ia] and CF3(CF2)n+1CH?CF(CF2)mCH?CH2 [Ib], wherein n is an integer of 0 to 5, and m is an integer of 0 to 6, is obtained as a mixture fraction of products [Ia] and [Ib] by reacting a polyfluoroalkyl iodide represented by the general formula: CF3(CF2)n+1CH2(CF2)m+1(CH2CH2)I [II], with an organic basic compound. The polyfluoroalkadiene mixture is compounds having a perfluoroalkyl group in which the number of successive CF2 groups is 5 or less, and is effectively used as a copolymerizable monomer in the production of resinous or elastomeric fluorine-containing copolymers, which are used as active ingredients of surface-treating agents, such as water- and oil-repellents and mold-release agents.

Abstract: A polyfluoro-1-alkene represented by the general formula: CF3(CF2)nCH2(CF2)mCH?CH2[I], wherein n is an integer of 0 to 5, and m is an integer of 1 to 7, is produced by reacting a polyfluoroalkyl iodide represented by the general formula: CF3(CF2)nCH2(CF2)m(CH2CH2)I [II], wherein n is an integer of 0 to 5, and m is an integer of 1 to 7, with an inorganic basic compound in the presence of a phase transfer catalyst. Alternatively, the polyfluoro-1-alkene is produced by reacting the polyfluoroalkyl iodide [II] with a nitrogen-containing organic basic compound, and is obtained product [I] as one fraction thereof. By the copolymerization of the polyfluoro-1-alkene with other fluorinated olefin monomers, a fluorine-containing copolymer having excellent light transmittance in the visible light range is formed.

Abstract: A fluorine-containing polymer comprising a fluoroalkyl alcohol (meth)acrylic acid derivative represented by a general formula, CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOCOCR?CH2 (in the formula, R is a hydrogen atom or a methyl group, n is an integer of 1 to 6, preferably 2 to 4, a is an integer of 1 to 4, b is an integer of 0 to 3, and c is an integer of 1 to 3) containing in 5 to 100 wt % as a polymerization unit. A organic solvent solution or aqueous dispersion of the fluorine-containing polymer is effectively used as, for example, a surface-modifying agent such as a water- and oil-repellent or an oil barrier.

Abstract: Disclosed is a mixture of fluoroalkyl alcohols represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)cOH [Ia] and CF3(CF2)n-1(CF?CH)aCF2(CF2CF2)b(CH2CH2)cOH [Ib], wherein n is an integer of 1 to 5, a is an integer of 1 to 4, b is an integer of 0 to 3, and c is an integer of 1 to 3. This fluoroalkyl alcohol mixture is produced by the reaction of a fluoroalkyl iodide represented by the general formula: CF3(CF2)n(CH2CF2)a(CF2CF2)b(CH2CH2)cI [II], with N-methylformamide, followed by hydrolysis in the presence of a basic compound.

Abstract: Disclosed is (1) a mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)c OCOCR?CH2 and CF3(CF2)n?1(CF?CH)a CF2(CF2CF2)b(CH2CH2)cOCOCR?CH2, wherein R is a hydrogen atom or a methyl group, n is an integer of 1 to 5, a is an integer of 1 to 4, b is an integer of 0 to 3, and c is an integer of 1 to 3; (2) a fluorine-containing polymer containing the mixture as a polymerization unit; and (3) a water- and oil-repellent comprising the fluorine-containing polymer as an active ingredient. The fluoroalkyl alcohol-unsaturated carboxylic acid derivatives are produced by an esterification reaction of a mixture of fluoroalkyl alcohols represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)cOH and CF3(CF2)n?1(CF?CH)aCF2(CF2CF2)b, (CH2CH2)cOH, with acrylic acid or methacrylic acid.

Abstract: Provided is a terminally iodized polyfluoroalkane represented by the general formula: CnF2n+1(CHXCFY)s+p(CF2CF2)t+rI ??[I] (in the formula, X and Y are each a hydrogen atom or a fluorine atom, wherein when Y is a fluorine atom, X is also a fluorine atom; n is an integer of 1 to 6; s+p is an integer of 1 to 5 and denotes the number of CHXCFY group; and t+r is 0 or an integer of 1 to 6 and denotes the number of tetrafluoroethylene skeleton). The terminally iodized polyfluoroalkane is produced by telomerizing a fluorine-containing olefin CHX?CFY and tetrafluoroethylene, successively, to CnF2n+1I in the presence of a peroxide initiator.

Abstract: A fluorine-containing polyether phosphonic acid ester compound represented by the following general formula: (R2O)(R1O)P(O)(CH2)aCF(CF3)[OCF2CF(CF3)]bO(CF2)CO[CF(CF3)CF2O]dCF(CF3)(CH2)eP(O)(OR3)(OR4) (where R1, R2, R3 and R4 are hydrogen atoms, alkyl groups, cycloalkyl groups, aryl groups, alkylaryl groups, aralkyl groups, or any of the foregoing groups substituted with halogen atoms, and subscripts a, b, c, d, and e are in conditions of 2?a+e?8, b+d?28, and 1?c?10, and subscripts b and d may be 0). The fluorine-containing polyether phosphonic acid ester compound is produced by reaction of a fluorine-containing polyether dialkyl halide represented by the following general formula: X(CH2)aCF(CF3)[OCF2CF(CF3)]bO(CF2)cO[CF(CF3)CF2O]dCF(CF3)(CH2)eX (X: Cl, Br or I) with a phosphite compound represented by the following general formula: (R1O)(R2O)P(OR) and/or (R3O)(R4O)P(OR) (R: a hydrogen atom or a lower alkyl group).

Abstract: A polyfluoroalkyl alcohol, or a (meth)acrylic acid derivative thereof, represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOR (R:H or (meth)acrylic acid group; n: 1-6; a: 1-4; b: 1-3; and c: 1-3). Polyfluoroalkyl alcohol (R: hydrogen atom) can be produced by reaction of fluoroalkyl iodide represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with N-methyl formamide, followed by hydrolysis in the presence of an acid catalyst, whereas polyfluoroalkyl alcohol (meth)acrylic acid derivative (R: (meth)acrylic acid group) can be produced by reaction of the polyfluoroalkyl alcohol with (meth)acrylic acid.

Abstract: A novel fluorine-containing ether alcohol having a terminal perfluoromethoxy group represented by the following general formula: CF3O[CF(CF3)CF2O]nCF(CF3)CH2OH (where n is an integer of 0-12) can be produced by reduction reaction of a fluorine-containing ether carboxylic acid alkyl ester represented by the following general formula: CF3O[CF(CF3)CF2O]nCF(CF3)COOR (where R is an alkyl group, and n is an integer of 0-12), and the fluorine-containing ether alcohol alone or as a mixture with a fluorine-containing ether alcohol having a terminal perfluoroethoxy group or a terminal perfluoropropoxy group is expected to show a peculiar surfactant characteristic owing to the peculiarity of reaction at the terminal position, and can be used as a dispersing agent or a levelling agent.

Abstract: A polyfluoroalkyl alcohol, or a (meth)acrylic acid derivative thereof, represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOR (R:H or (meth)acrylic acid group; n: 1-6; a: 1-4; b: 1-3; and c: 1-3). Polyfluoroalkyl alcohol (R: hydrogen atom) can be produced by reaction of fluoroalkyl iodide represented by the following general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with N-methyl formamide, followed by hydrolysis in the presence of an acid catalyst, whereas polyfluoroalkyl alcohol (meth)acrylic acid derivative (R: (meth)acrylic acid group) can be produced by reaction of the polyfluoroalkyl alcohol with (meth)acrylic acid.