Abstract: A polyfluoroalkylphosphonic acid ester represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OR)2 (R is an alkyl group having 1 to 4 carbon atoms, 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) is produced by a process of reacting a polyfluoroalkyl iodide represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with a trialkyl phosphite represented by the general formula: P(OR)3 or by a process of reacting a polyfluoro-1-alkene represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)bCH?CH2 with a dialkyl phosphite represented by the general formula: (RO)2P(O)H.

Abstract: A fluorine-containing vinyl ether compound of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOCH?CH2 is produced by subjecting a fluorine-containing alcohol of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOH 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, and 2-haloethyl vinyl ether of the formula: XCH2CH2OCH?CH2 to XCH2CH2OH-elimination reaction in the presence of a palladium-based catalyst and an aliphatic amine. The fluorine-containing vinyl ether compound contain a perfluoroalkyl group having 6 or less carbon atoms, which is said to have low bioaccumulation potential.

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 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: A fluorine-containing vinyl ether compound of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOCH?CH2 is produced by subjecting a fluorine-containing alcohol of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOH 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, and 2-haloethyl vinyl ether of the formula: XCH2CH2OCH?CH2 to XCH2CH2OH-elimination reaction in the presence of a palladium-based catalyst and an aliphatic amine. The fluorine-containing vinyl ether compound contain a perfluoroalkyl group having 6 or less carbon atoms, which is said to have low bioaccumulation potential.

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: 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 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: Disclosed is a polyfluoroalkylphosphonic acid oxyalkylene ester of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)[O(RO)mR?]d(OH)2-d (RO is a C2-C6 linear or branched oxyalkylene group, R? is a hydrogen atom or a C1-C20 alkyl group or aralkyl group, n is 1 to 6, a is 1 to 4, b is 1 to 3, c is 1 to 3, d is 1 or 2, and m is 1 to 100), which is a compound having a perfluoroalkyl group containing 6 or less carbon atoms and referred to as having low bioaccumulation potential, and exhibiting, 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. This compound is produced by subjecting a polyfluoroalkylphosphonic acid of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 and a polyalkyleneglycol or a monoether thereof of the formula: HO(RO)mR? to a condensation reaction.

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 an emulsifier comprising, as an active ingredient, a polyfluoroalkylphosphonic acid salt represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OM1)(OM2), wherein M? is a hydrogen atom, an alkali metal, an ammonium base, or an organic amine base, M2 is an alkali metal, an ammonium base, or an organic amine base, 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. An aqueous solution or organic solvent solution of the emulsifier can be effectively used to emulsify a perfluoropolyether oil or a perfluorocarbon compound. The resulting emulsion exhibits excellent emulsification stability, and thus can be effectively used as a mold-releasing agent.

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: Disclosed is a mold-releasing agent comprising, as active ingredients, a polyfluoroalkylphosphonic acid represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 (n: an integer of 1 to 6, a: an integer of 1 to 4, b: an integer of 1 to 3, c: an integer of 1 to 3), or a salt thereof and a polyfluoroalkylphosphonic acid oxyalkylene ester represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)[O(RO)mR?]d(OH)2?d (RO: a C2-C6 linear or branched oxyalkylene group, R?: a hydrogen atom, a C1-C20 alkyl group, or aralkyl group, n: an integer of 1 to 6, a: an integer of 1 to 4, b: an integer of 1 to 3, c: an integer of 1 to 3, d: an integer of 1 or 2, m: an integer of 1 to 100).

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 an emulsifier comprising, as an active ingredient, a polyfluoroalkylphosphonic acid salt represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OM1)(OM2), wherein M? is a hydrogen atom, an alkali metal, an ammonium base, or an organic amine base, M2 is an alkali metal, an ammonium base, or an organic amine base, 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. An aqueous solution or organic solvent solution of the emulsifier can be effectively used to emulsify a perfluoropolyether oil or a perfluorocarbon compound. The resulting emulsion exhibits excellent emulsification stability, and thus can be effectively used as a mold-releasing agent.

Abstract: Disclosed is a polyfluoroalkylphosphonic acid oxyalkylene ester of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)[O(RO)mR?]d(OH)2?d (RO is a C2-C6 linear or branched oxyalkylene group, R? is a hydrogen atom or a C1-C20 alkyl group or aralkyl group, n is 1 to 6, a is 1 to 4, b is 1 to 3, c is 1 to 3, d is 1 or 2, and m is 1 to 100), which is a compound having a perfluoroalkyl group containing 6 or less carbon atoms and referred to as having low bioaccumulation potential, and exhibiting, 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. This compound is produced by subjecting a polyfluoroalkylphosphonic acid of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 and a polyalkyleneglycol or a monoether thereof of the formula: HO(RO)mR? to a condensation reaction.

Abstract: Disclosed is a mold-releasing agent comprising, as active ingredients, a polyfluoroalkylphosphonic acid represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 (n: an integer of 1 to 6, a: an integer of 1 to 4, b: an integer of 1 to 3, c: an integer of 1 to 3), or a salt thereof and a polyfluoroalkylphosphonic acid oxyalkylene ester represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)[O(RO)mR?]d(OH)2-d (RO: a C2-C6 linear or branched oxyalkylene group, R?: a hydrogen atom, a C1-C20 alkyl group, or aralkyl group, n: an integer of 1 to 6, a: an integer of 1 to 4, b: an integer of 1 to 3, c: an integer of 1 to 3, d: an integer of 1 or 2, m: an integer of 1 to 100).

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 polyfluoroalkylphosphonic acid ester represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OR)2 (R is an alkyl group having 1 to 4 carbon atoms, 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) is produced by a process of reacting a polyfluoroalkyl iodide represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cI with a trialkyl phosphite represented by the general formula: P(OR)3 or by a process of reacting a polyfluoro-1-alkene represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)bCH?CH2 with a dialkyl phosphite represented by the general formula: (RO)2P(O)H.

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.