Unimatec Co., Ltd

Seiichiro Murata

Katsuyuki Sato

Yoshiyama Kaneumi

Masayosi Horiuti

Hideki Abe

Daisuke Murai

Keisuke Kokin

Mitsuru Maeda

Satoshi Kurihara

Akihiko Ikeda

Haruyoshi Tatsu

Takashi Enokida

Sumiko Mouri

Ji-Shan Jin

Yusuke Takahashi

Soichiro Murakami

A polyfluoroalkylphosphonic acid ester represented by the general formula: CF(CHCF)(CFCF)(CHCH)P(O)(OR)(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: CF(CHCF)(CFCF)(CHCH)I with a trialkyl phosphite represented by the general formula: P(OR)or by a process of reacting a polyfluoro-1-alkene represented by the general formula: CF(CHCF)(CFCF)CH&#x2550;CHwith a dialkyl phosphite represented by the general formula: (RO)P(O)H.

Polyfluoroalkylphosphonic acid ester and process for producing the same

A fluorine-containing vinyl ether compound of the formula: CF(CHCF)(CFCF)(CHCH)OCH&#x2550;CHis produced by subjecting a fluorine-containing alcohol of the formula: CF(CHCF)(CFCF)(CHCH)OH 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: XCHCHOCH&#x2550;CHto XCHCHOH-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.

Fluorine-containing vinyl ether compound and method for producing the same

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: CFCFCH&#x2550;CF(CFCF)I [Ia] and CFCF&#x2550;CHCF(CFCF)I [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.

Peroxide-crosslinkable fluoroelastomer

A fluorine-containing polymer comprising a fluoroalkyl alcohol (meth)acrylic acid derivative represented by a general formula, CF(CHCF)(CFCF)(CHCH)OCOCR&#x2550;CH(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.

Fluorine-containing polymer and surface-modifying agent containing the same as active ingredient

Disclosed is (1) a mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives represented by the general formulae: CF(CF)(CH&#x2550;CF)(CFCF)(CHCH)OCOCR&#x2550;CHand CF(CF)(CF&#x2550;CH)CF(CFCF)(CHCH)OCOCR&#x2550;CH, 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: CF(CF)(CH&#x2550;CF)(CFCF)(CHCH)OH and CF(CF)(CF&#x2550;CH)CF(CFCF), (CHCH)OH, with acrylic acid or methacrylic acid.

Mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives, polymer of the mixture, and water-and oil-repellent containing the polymer as active ingredient

A fluorine-containing polyether carboxylic acid amide represented by the general formula: CFO(CFO)RfCONHAr, 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: CF(CFO)RfCOF, wherein Rf, n, and m are as defined above, with a nitrogen-containing heterocyclic amine compound represented by the general formula: ArNH, wherein Ar is as defined above; wherein the reaction is carried out while a reaction temperature is first increased to 80 to 100&#xb0; C., and then increased at a temperature increase rate that produces a temperature difference of 3 to 5&#xb0; C. after 48 hours.

Method for producing fluorine-containing polyether carboxylic acid amide

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: CF(CHCF)(CFCF)CH&#x2550;CH(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: CF(CHCF)(CFCF)(CHCH)P(O)(OH)(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.

Mold-releasing agent

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: CF(CHCF)(CFCF)CH&#x2550;CH(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.

Graft copolymer and mold-releasing agent comprising same as active ingredient

Disclosed is a polyfluoroalkylphosphonic acid oxyalkylene ester of the formula: CF(CHCF)(CFCF)(CHCH)P(O)[O(RO)R'](OH)(RO is a C-Clinear or branched oxyalkylene group, R&#x2032; is a hydrogen atom or a C-Calkyl 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: CF(CHCF)(CFCF)(CHCH)P(O)(OH)and a polyalkyleneglycol or a monoether thereof of the formula: HO(RO)R&#x2032; to a condensation reaction.

Polyfluoroalkylphosphonic acid oxyalkylene ester, method for producing the same, and mold-releasing agent comprising the same as active ingredient

Disclosed is an emulsifier comprising, as an active ingredient, a polyfluoroalkylphosphonic acid salt represented by the general formula: CF(CHCF)(CFCF)(CHCH)P(O)(OM)(OM), wherein M' is a hydrogen atom, an alkali metal, an ammonium base, or an organic amine base, Mis 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.

Polyfluoroalkylphosphonic acid salt emulsifier and mold-releasing agent comprising the same as active ingredient

Provided is a terminally iodized polyfluoroalkane represented by the general formula:CF(CHXCFY)(CFCF)I&#x2003;&#x2003;[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&#x2550;CFY and tetrafluoroethylene, successively, to CFI in the presence of a peroxide initiator.

Terminally iodized polyfluoroalkane and method for producing the same

Disclosed is a mold-releasing agent comprising, as active ingredients, a polyfluoroalkylphosphonic acid represented by the general formula: CF(CHCF)(CFCF)(CHCH)P(O)(OH)(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: CF(CHCF)(CFCF)(CHCH)P(O)[O(RO)R'](OH)(RO: a C-Clinear or branched oxyalkylene group, R&#x2032;: a hydrogen atom, a C-Calkyl 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). This mold-releasing agent comprises, as an active ingredient, a polyfluoroalkylphosphonic acid oxyalkylene ester having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, but exhibits mold release performance equivalent to that of a mold-releasing agent comprising a compound having a perfluoroalkyl group containing 8 or more carbon atoms as an active ingredient.

Disclosed is a mixture of fluoroalkyl alcohols represented by the general formulae: CF(CF)(CH&#x2550;CF)(CFCF)(CHCH)OH [Ia] and CF(CF)(CF&#x2550;CH)CF(CFCF)(CHCH)OH [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: CF(CF)(CHCF)(CFCF)(CHCH)I [II], with N-methylformamide, followed by hydrolysis in the presence of a basic compound.

Fluoroalkyl alcohol mixture and method for producing the same

Disclosed is a polyfluoroalkylphosphonic acid represented by the general formula: CF(CHCF)(CFCF)(CHCH)P(O)(OH), 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: CF(CHCF)(CFCF)(CHCH)P(O)(OR), wherein R is a C-Calkyl 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.

Polyfluoroalkylphosphonic acid, method for producing the same and mold-releasing agent comprising the same as active ingredient

A mixture of polyfluoroalkadienes represented by the general formulae: CF(CF)CF&#x2550;CH(CF)CH&#x2550;CH[Ia] and CF(CF)CH&#x2550;CF(CF)CH&#x2550;CH[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: CF(CF)CH(CF)(CHCH)I [II], with an organic basic compound. The polyfluoroalkadiene mixture is compounds having a perfluoroalkyl group in which the number of successive CFgroups 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.

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Ibaraki, Japan

Seiichiro Murata