Unimatec Co., Ltd

Nisshinbo Holdings Inc.

Keisuke Kokin

Rie Aotsu

Junya Seino

Seiichiro Murata

Kimihiko Urata

Takehiro Sonoi

Hideki Abe

Takashi Enokida

Mitsuru Maeda

Jun Kanega

Haruyoshi Tatsu

Satoru Saito

Gen Masuda

Katsuyuki Sato

Sunao Ikeda

Daisuke Murai

Yusuke Takahashi

Katsumi Suzuki

Ji-Shan Jin

Takuhiro Miyamura

Daisuke Ito

Hideyuki Ono

Soichiro Murakami

A fluorine-containing pyrimidine compound is provided represented by general formula (1), (2), or (3): wherein: W and X each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CFwhere n is an integer of 1 to 10, a nitro group, —OA, —SOA, —SA, —NAA, —B(OA)(OA), —COA, —COOA, or —CONAA; Y represents a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CFwhere n is an integer of 1 to 10, a cyano group, a nitro group, —OA, —SOA, —SA, —NAA, —B(OA)(OA), —COA, —COOA, or —CONAA; Z represents a halogen atom or —OA; Aand Aeach independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms; and Arepresents a hydrocarbon group having 1 to 12 carbon atoms.

Fluorine-containing pyrimidine compound and fluorine-containing pyrimidinone compound

A fluorine-containing pyrimidine compound represented by formula (1), (2) or (3) is provided: wherein in formulae (1) to (3), R represents a hydrocarbon group having 1 to 12 carbon atoms, X and Y each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CF, a nitro group, a boronic acid group, -OA, —SOA, -NAA, —COOAor —CONAA, Z represents CW or N, W represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CF, a nitro group, a boronic acid group, —OA, —SOA, —NAA, —COOAor —CONAA, n is an integer of 1 to 10 and m is an integer of 0 to 3, and Aand Aeach independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

Fluorine-containing pyrimidine compound and method for producing same

A fluorine-containing fused ring pyrimidine compound is provided represented by the following formula (1): wherein in the above formula (1): R represents a hydrocarbon group having 1 to 12 carbon atoms; X, Y and Z each independently represent a carbon atom or a nitrogen atom; X and Y optionally form ring Qwith a carbon atom or a nitrogen atom bonded to each other; Y and Z optionally form ring Qwith a carbon atom or a nitrogen atom bonded to each other; and ring Qand ring Qeach represent a monocyclic ring or fused ring having 6, 10 or 14 π electrons constituting the ring and optionally comprise a heteroatom.

Fluorine-containing fused ring pyrimidine compound and method for producing same

A fluorine-containing pyrimidine compound is represented by the following formula (1) or (2): wherein R represents a hydrocarbon group having 1 to 12 carbon atoms; and X and Y each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CFwhere n is an integer of 1 to 10, a nitro group, a boronic acid group, —OA, —SOAwhere m is an integer of 0 to 3, —NAA, —COOA, or —CONAA, where Aand Aeach independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

Fluorine-containing pyrimidine compound and manufacturing method for same

A fluorine-containing pyrimidine compound is provided represented by formula (1): wherein in the above formula (1), R represents a hydrocarbon group having 1 to 12 carbon atoms, Band Beach independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CFwhere n is an integer of 1 to 10, a nitro group, a boronic acid group, —OA, —SOAwhere m is an integer of 0 to 3, —NAA, —COOAor —CONAA, W, X, Y and Z each independently represent CV or N, V represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, —CFwhere n is an integer of 1 to 10, a nitro group, a boronic acid group, —OA, —SOAwhere m is an integer of 0 to 3, —NAA, —COOAor —CONAA, and Aand Aeach independently represent a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

A fluorine-containing pyrimidine compound is provided represented by general formula (1), (2), (3), (4), (5), or (6) below.

Fluorine-containing pyrimidine compound and method for manufacturing the same

Provided are: an ionic liquid including the fluorine-containing phosphate ester anions represented by formula (1); and a lubricating oil composition including said ionic liquid. (In the formula, Rf represents a C1-14 perfluoroalkyl group. Rrepresents a C1-8 alkyl group.)

Ionic liquid including fluorine-containing phosphate ester anions, and lubricating oil composition

Provided are a fluorine-containing monomer capable of being dissolved in a general organic solvent such as a hydrocarbon solvent and simultaneously having excellent water and oil repellency, and a method for producing the fluorine-containing monomer. The fluorine-containing monomer is a carboxylic acid ester compound having a polymerizable functional group and a fluorine atom group, represented by the following general formula: CFO&#x2014;(CFO)&#x2014;CFCOOR. The method is a process for producing the carboxylic acid ester compound, characterized by that any one of an isocyanulate derivative, a phthalic acid derivative and a cycloalkane dialcohol modified (meth)acrylate each having a terminal hydroxyl group is made to react with a perfluoropolyether carboxylic acid halide.

Carboxylic acid ester compound having polymerizable functional group and fluorine atom group, and method for producing same

A fluorine-containing ether monocarboxylic acid aminoalkyl ester represented by the general formula:CFO[CF(CF)CFO]CF(CF)COO(CH)NRR(wherein Ris 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; Ris 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 2 to 20, preferably an integer of 4 to 10; and b is an integer of 1 to 12, preferably an integer of 1 to 3). Such a fluorine-containing ether monocarboxylic acid ester having an amino group at the end of the ester group is produced by reacting a perfluoroether carboxylic acid fluoride compound CFO[CF(CF)CFO]CF(CF)COF and a hydroxyalkyl amine compound HO(CH)NRRin the presence of an alkali metal fluoride.

Fluorine-containing ether monocarboxylic acid aminoalkyl ester and a method for producing the same

A perfluorovinyloxy polyether carboxylic acid alkali metal salt represented by the general formula is provided:CF&#x2550;CF[OCFCF(CF)]O(CF)O[CF(CF)CFO]CF(CF)COOM&#x2003;&#x2003;[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&#x2550;CF[OCFCF(CF)]O(CF)O[CF(CF)CFO]CF(CF)COOR&#x2003;&#x2003;[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.

Perfluorovinyloxy polyether carboxylic acid alkali metal salt and method for producing the same

A bis(perfluoroether carboxylic acid alkyl)amino ester represented by the general formula: {CFO[CF(CF)CFO]CF(CF)COO(CH)}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: CFO[CF(CF)CFO]CF(CF)COF and a bis(hydroxyalkyl)amine compound of the formula: HO(CH)NR(CH)OH at a molar ratio of 2:1 in the presence of an alkali metal fluoride.

Bis(perfluoroether carboxylic acid alkyl)amino ester and method 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

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 diurethane compound R(SO)(CH)OCONH&#x2014;R&#x2014;NHCOO(CH)(SO)Rproduced by a method allowing a diamine compound HNRNHto react with a chloroformate compound ClCOO(CH)(SO)Ror a method allowing a diisocyanate compound OCNRNCO to react with a hydroxyl-containing compound R(SO)(CH)OH. The diurethane compound is compounded with multivalent amine crosslinkable group-containing acrylic rubber together with a basic vulcanization accelerator to form an acrylic rubber composition. The acrylic rubber composition including the diurethane compound as a vulcanizing agent decreases a delay in the vulcanization rate due to prevention of scorching and also allows a vulcanized article to satisfy the compression set characteristics.

Diurethane compound, process for producing the same, and acrylic rubber composition containing the same

A fluorine-containing elastomer having a copolymer composition, which comprises (a) 50-85 mol. % of vinylidene fluoride, (b) 0-25 mol. % of tetrafluoroethylene, (c) 7-20 mol. % of perfluoro(methyl vinyl ether), (d) 2.5-15 mol. % of CF&#x2550;CFO[CFCF(CF)O]nCF(n: 2-6), (e) 0.1-2 mol. % of CF&#x2550;CFO[CFCF(CF)O]mCFCF(m: 2-6), and (f) 0.1-2 mol. % of RfX (Rf: an unsaturated fluorohydrocarbon group having 2-8 carbon atoms, which can contain at least one ether bond, X: bromine or iodine), can provide a fluorine-containing elastomer composition, which comprises 100 parts by weight of the fluorine-containing elastomer, 0.1-10 parts by weight of an organic peroxide, 0.1-10 parts by weight of a polyfunctional unsaturated compound, and at least 2 parts by weight of an acid acceptor. The composition can give vulcanizates having a distinguished elongation at break at high temperatures such as 100&#xb0; C., and distinguished compression set characteristics at low temperatures such as 0&#xb0; C.

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Ibaraki, Japan

Keisuke Kokin