Ibaraki, Japan
Ibaraki, Japan

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A mixture of polyfluoroalkene carboxylic acids or salts thereof represented by the general formulas:C_(n)F_(2n+1)CH=CF(CF_(2)CF_(2))_(m)CF_(2)COOMandC_(n-1)F_(2n-1)CF=CHCF_(2)(CF_(2)CF_(2))_(m)CF_(2)COOMwherein M is a hydrogen atom, an ammonium salt, an organic amine salt or an alkali metal, n is an integer of 1 to 6 and m is an integer of 0 to 2. The mixture of polyfluoroalkene carboxylic acids or salts thereof is produced by subjecting a polyfluoroalkane carboxylic acids represented by the general formula:C_(n)F_(2n+1)(CH_(2)CF_(2))(CF_(2)CF_(2))_(m)CF_(2)COOHto a dehydrofluorination reaction in the presence of a nitrogen-containing heterocyclic compound catalyst, and has a lower critical micelle concentration and less surface tension at that time, therefore, the mixture of polyfluoroalkene carboxylic acids or salts thereof can be effectively used as a surfactant in the polymerization of fluorine-containing monomers.


Patent
Unimatec Co. and Hirosaki University | Date: 2016-01-13

Fluorine-containing nano composite particles comprising a condensate of a fluorine-containing alcohol represented by the general formula:R_(F)-A-OH[I]wherein R_(F) is a perfluoroalkyl group or a polyfluoroalkyl group in which some of the fluorine atoms of the perfluoroalkyl group are replaced by hydrogen atoms, and A is an alkylene group having 1 to 6 carbon atoms; and an alkoxysilane,or fluorine-containing nano composite particles comprising a condensate of a fluorine-containing alcohol represented by the general formula:R_(F)-A-OH[Ia]or the general formula:HO-A-R_(F)-A-OH[Ib]wherein R_(F) is a linear or branched perfluoroalkyl group containing an O, S, or N atom, R_(F) is a linear or branched perfluoroalkylene group containing an O, S, or N atom, and A is an alkylene group having 1 to 6 carbon atoms; and an alkoxysilane.


Disclosed is a fluorine-containing oligomer comprising a copolymer of a fluoroalkyl alcohol (meth)acrylic acid derivative represented by the general formula:C_(n)F_(2n+1)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)(CH_(2)CH_(2))_(c)OCOCR_(=)CH_(2)[1]wherein R is a hydrogen atom or a methyl group, n is an integer of 1 to 6, 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; and a (meth)acrylic acid derivative represented by the general formula:(CH_(2=)CRCO)_(m)R[II]wherein R is a hydrogen atom or a methyl group, m is 1, 2, or 3; and when m is 1, R is OH group, NH_(2) group that is unsubstituted or mono- or di-substituted with an alkyl group having 1 to 6 carbon atoms, or a monovalent group derived from an alkylene glycol or polyalkylene glycol group containing an alkylene group having 2 or 3 carbon atoms; when m is 2 or 3, R is a divalent or trivalent organic group derived from a diol or triol. The copolymerization reaction is performed using a hydrocarbon-based peroxide or azo compound polymerization initiator. Also disclosed are nano-silica composite particles formed as a condensate of the fluorine-containing oligomer and an alkoxysilane with nano-silica particles.


Fluorine-containing calcium composite particles comprising an aggregate of a fluorine-containing alcohol represented by the general formula:C_(n)F_(2n+1)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)(CH_(2)CH_(2))_(c)OHwherein n is an integer of 1 to 6, 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; and a calcium compound,or fluorine-containing calcium composite particles comprising a condensate of a fluorine-containing alcohol represented by the general formula: R_(F)-A-OH or the general formula: HO-A-R_(F)-A-OH wherein R_(F) is a liner or branched perfluoroalkyl group that may contain an O, S, or N atom, or a polyfluoroalkyl group in which some of the fluorine atoms of the perfluoroalkyl group are replaced by hydrogen atoms; R_(F) is a linear or branched perfluoroalkylene group containing an O, S, or N atom; and A is an alkylene group having 1 to 6 carbon atoms; alkoxysilane, and a calcium compound. The latter fluorine-containing calcium composite particles are used as an active ingredient of water- and oil-repellent.


Patent
Unimatec Co. and Hirosaki University | Date: 2016-01-13

Fluorine-containing nano-silica composite particles comprising a condensate of a fluorine-containing alcohol represented by the general formula:R_(F)-A-OH[I]wherein R_(F) is a perfluoroalkyl group or a polyfluoroalkyl group in which some of the fluorine atoms of the perfluoroalkyl group are replaced by hydrogen atoms, and A is an alkylene group having 1 to 6 carbon atoms; and an alkoxysilane with nano-silica particles,or fluorine-containing nano-silica composite particles comprising a condensate of a fluorine-containing alcohol represented by the general formula:R_(F)-A-OH[Ia]or the general formula:HO-A-R_(F)-A-OH[Ib]wherein R_(F) is a linear or branched perfluoroalkyl group containing an O, S, or N atom, R_(F) is a linear or branched perfluoroalkylene group containing an O, S, or N atom, and A is an alkylene group having 1 to 6 carbon atoms; and an alkoxysilane with nano-silica particles.


A bis(perfluoroether carboxylic acid alkyl)amino ester represented by the general formula: {C_(n)F_(2n+1)O[CF(CF_(3))CF_(2)O]_(a)CF(CF_(3))COO(CH_(2))_(b)}_(2)NR, wherein R is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group; preferably an alkyl group having 1 to 6 carbon atoms or an aryl group; n is an integer of 1 to 3; a is an integer of 0 to 20, preferably an integer of 1 to 6; and b is an integer of 1 to 12, preferably an integer of 1 to 4. The bis(perfluoroether carboxylic acid alkyl)amino ester having an amino group at the end of the ester group is produced by reacting a perfluoroether carboxylic acid fluoride compound of the formula: C_(n)F_(2n+1)O[CF(CF_(3))CF_(2)O]_(a)CF(CF_(3))COF and a bis(hydroxyalkyl)amine compound of the formula: HO(CH_(2))_(b)NR(CH_(2))_(b)OH at a molar ratio of 2:1 in the presence of an alkali metal fluoride.


A perfluorovinyloxy polyether carboxylic acid alkali metal salt represented by the general formula is provided:CF_(2)=CF[OCF_(2)CF(CF_(3))]_(b)O(CF_(2))_(a)O[CF(CF_(3))CF_(2)O]_(c)CF(CF_(3))COOM[I],wherein M is alkali metal, preferably sodium or potassium, a is an integer of 1 to 6, preferably 2, and b+c is an integer of 0 to 6, preferably 0 or 1. This perfluorovinyloxy polyether carboxylic acid alkali metal salt is produced by subjecting a perfluorovinyloxy polyether carboxylic acid alkyl ester represented by the general formula:CF_(2)=CF[OCF_(2)CF(CF_(3))]_(b)O(CF_(2))_(a)O[CF(CF_(3))CF_(2)O]_(c)CF(CF_(3))COOR[II],wherein R is an alkyl group having 1 to 12 carbon atoms, a is an integer of 1 to 6, and b+c is an integer of 0 to 6; to hydrolysis or solvolysis in the presence of an alkali metal hydroxide.


A fluorine-containing copolymer comprising a copolymer of (A) C_(n)F_(2n+1)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)(CH_(2)CH_(2))_(c)OCOCR=CH_(2) (R : H, a methyl group, n : 1-6, a : 1-4, b : 1-3, c : 1-3), (B) CH_(2)=CRCOOR^(1) (R : H, a methyl group, R^(1) : C_(1)-C_(30) alkyl group, or an aralkyl group; and (C) CH_(2)=CRCOOR^(2)NCO or CH_(2)=CRCOOR^(2)NHCOR^(3) (R : H, a methyl group, R^(2) : C_(1)-C_(30) alkylene group, R^(3) : blocked group of an isocyanate group, and a surface-modifying agent containing the fluorine-containing copolymer as an active ingredient. The surface-modifying agent has excellent adhesion to substrates and improved processing durability.


Patent
Unimatec Co. | Date: 2016-11-02

The object of the present invention is to provide a fluorine-containing macroinitiator, particularly a fluorine-containing macroinitiator that enables production of a fluorine-containing block copolymer containing a non-fluorine vinyl-based monomer having a long side chain. The fluorine-containing macroinitiator of the present invention comprises a polymer represented by the following formula (1) and having a number-average molecular weight of 3, 000 to 100,000. In the following formula (1), R^(2), R^(3) and R^(4) are each a specific group, and Q is a polymer segment composed of a structural unit represented by the following formula (2). In the following formula (2), R^(1) is a hydrogen atom or a methyl group, Rf is a fluoroalkyl group having a specific structure, and k is an appropriate integer that is not 0.


Patent
Unimatec Co. | Date: 2016-11-02

The object of the present invention is to provide a fluorine-containing diblock copolymer having good water and oil repellency by using, as a raw material, a fluorine-containing (meth)acrylic ester having low bioaccumulation potential. The fluorine-containing diblock copolymer of the present invention is producedby: (process A) a process for producing a fluorine-containing diblock copolymer by polymerizing a fluorine-containing (meth) acrylic ester represented by the following formula (1) in the presence of a trithiocarbonic ester compound and a radical polymerization initiator and then polymerizing a non-fluorine vinyl-based monomer, or (process B) a process for producing a fluorine-containing diblock copolymer by polymerizing a non-fluorine vinyl-based monomer in the presence of a trithiocarbonic ester compound and a radical polymerization initiator and then polymerizing a fluorine-containing (meth) acrylic ester represented by the following formula (1).

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