UNIMATEC Co.

Ibaraki, Japan

UNIMATEC Co.

Ibaraki, Japan
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Patent
Unimatec Co. and Hirosaki University | Date: 2017-01-18

Fluorine-containing boric acid composite capsule particles comprising a condensate of a fluorine-containing alcohol, a guest compound, and boric acid particles, wherein the fluorine-containing alcohol is represented by the general formula:R_(F)-A-OHwherein R_(F) is:a perfluoroalkyl group having 6 or less carbon atoms,a linear or branched perfluoroalkyl group containing a terminal perfluoroalkyl group having 6 or less carbon atoms and a perfluoroalkylene group having 6 or less carbon atoms, and containing an O, S, or N atom, ora polyfluoroalkyl group in which some of the fluorine atom or atoms of the perfluoroalkyl group are replaced by hydrogen atom or atoms, and which contains a terminal perfluoroalkyl group having 6 or less carbon atoms and a perfluoroalkylene group having 6 or less carbon atoms, wherein the perfluoroalkylene group may contain an O, S, or N atom, and one fluorine atom of the terminal perfluoroalkyl group may be replaced by -(CH_(2))_(f)OH (wherein f is an integer of 1 to 3); andA is an alkylene group having 1 to 6 carbon atoms.


Patent
Unimatec Co. and Hirosaki University | Date: 2017-01-18

The present invention provides fluorine-containing boric acid composite particles comprising a condensate of boric acid and a fluorine-containing alcohol represented by the general formula:R_(F)-A-OH[I]wherein R_(F) is a perfluoroalkyl group having 6 or less carbon atoms, or a polyfluoroalkyl group, in which some of the fluorine atoms of the perfluoroalkyl group are replaced by a hydrogen atom or atoms, and which contains a terminal perfluoroalkyl group having 6 or less carbon atoms and a perfluoroalkylene group having 6 or less carbon atoms; and A is an alkylene group having 1 to 6 carbon atoms. The fluorine-containing boric acid composite particles may also be a condensate of boric acid, the said fluorine-containing alcohol, and an alkoxysilane at a molar ratio of 1.0 or less based on the fluorine-containing alcohol. These fluorine-containing boric acid composite particles has excellent adhesion to inorganic substrates, and the like.


Patent
Unimatec Co. and Hirosaki University | Date: 2017-01-18

Fluorine-containing titanium oxide - nano-silica composite particles comprising a condensate of a fluorine-containing alcohol and an alkoxysilane, and titanium oxide and nano-silica particles, wherein the fluorine-containing alcohol is represented by the general formula:R_(F)-A-OH[I](wherein R_(F) is a perfluoroalkyl group having 6 or less carbon atoms, or a polyfluoroalkyl group, in which some of the fluorine atom or atoms of the perfluoroalkyl group are replaced by a hydrogen atom or atoms, and which contains a terminal perfluoroalkyl group having 6 or less carbon atoms and a perfluoroalkylene group having 6 or less carbon atoms; and A is an alkylene group having 1 to 6 carbon atoms). The fluorine-containing titanium oxide - nano-silica composite particles do not have difficulty in handling as with hydrogen fluoride, can be produced by using a fluorine-containing alcohol, which can be easily handled, and can produce a product capable of suppressing a decrease in the function of the titanium oxide as a photocatalyst even when subjected to a high-temperature heat treatment.


Patent
Unimatec Co. | Date: 2017-08-09

A polyfluoroalkyl allyl compound represented by the general formula:CF_(3)(CF_(2))_(n)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)CH_(2)CH=CH_(2)[I](n : 0 to 5, a : 1 or 2, b : 0 to 3). The polyfluoroalkyl allyl compound is produced by reacting a carboxylic acid allyl adduct represented by the general formula:CF_(3)(CF_(2))_(n)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)CH_(2)CHICH_(2)OCOR[II](n, a, and b are as defined above, and R : a C_(1)-C_(3) alkyl group) with a transition metal. This method for producing provides a polyfluoroalkyl allyl compound used as a synthetic intermediate for a fluorine-containing alkylsilane compound that can remove free iodine derived from the raw material compound, before a hydrosilylation reaction is performed, without using a metal reagent having a high environmental impact, and that has excellent handling properties.


A fluorine-containing alkylsilane compound represented by the general formula:CF_(3)(CF_(2))_(n)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)(CH_(2))_(3)SiR_(3-d)X_(d)[I]wherein n is an integer of 0 to 5; a is 1 or 2; b is an integer of 0 to 3; R is a C_(1)-C_(3) alkoxy group, a fluorine-containing alkoxy group, or an alkenyl group; X is halogen; and d is an integer of 0 to 3. The fluorine-containing alkylsilane compound is produced by reacting, in the presence of a transition metal catalyst, a polyfluoroalkyl allyl compound represented by the general formula:CF_(3)(CF_(2))_(n)(CH_(2)CF_(2))_(a)(CF_(2)CF_(2))_(b)CH_(2)CH=CH_(2)[II]wherein n, a, and b are as defined above, with:- an alkoxysilane, or- a chlorosilane, followed by a reaction with lower alcohol or metal alkenyl. The production method gives a fluorine-containing alkylsilane compound that can remove free iodine derived from the raw material compound, before a hydrosilylation reaction is performed, without using a metal reagent having a high environmental load, and that also has excellent handling properties.


Provided are a fluorine-containing monomer soluble in a hydrocarbon-based solvent as well as excellent in water and oil repellence, and a manufacturing method therefor. The fluorine-containing monomer is a carboxylic acid ester/carbamate compound having a polymerizable functional group and a fluorine atom group, and represented by the following general formula: C_(a)F_(2a+1)O-(C_(b)F_(2b)O)_(c)-C_(2)F_(4)COO-Z-(CONHR)_(d). The method for manufacturing the carboxylic acid ester/carbamate compound is comprised of the steps of making an isocyanate compound having a polymerizable functional group react with an alcohol such as a polyalkylene glycol, a cycloalkane dimethanol, or a polyhydric alcohol to produce a hydroxycarbamate, and subsequently making the resulting hydroxycarbamate react with a perfluoropolyether carboxylic acid halide.


Patent
Unimatec Co. and Hirosaki University | Date: 2017-01-18

A resin - fluorine-containing boric acid composite particles composite material comprising a resin, and a condensate of boric acid and a fluorine-containing alcohol represented by the general formula R_(F)-A-OH (wherein R_(F) is a perfluoroalkyl group having 6 or less carbon atoms, or a polyfluoroalkyl group, in which some of the fluorine atom or atoms of the perfluoroalkyl group are replaced by a hydrogen atom or hydrogen atoms, and which contains a terminal perfluoroalkyl group having 6 or less carbon atoms and a perfluoroalkylene group having 6 or less carbon atoms; and A is an alkylene group having 1 to 6 carbon atoms, or comprising a resin, and a condensate of boric acid, the said fluorine-containing alcohol and an alkoxysilane at a molar ratio of 1.0 or less based on the fluorine-containing alcohol. These resin - fluorine-containing boric acid composite particles composite material has good adhesion to inorganic substrates, and the like.


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.


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.


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.

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