WO2005113488A1 - フルオロアルキル基と炭化水素基を有する分岐型界面活性剤 - Google Patents
フルオロアルキル基と炭化水素基を有する分岐型界面活性剤 Download PDFInfo
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- WO2005113488A1 WO2005113488A1 PCT/JP2005/008893 JP2005008893W WO2005113488A1 WO 2005113488 A1 WO2005113488 A1 WO 2005113488A1 JP 2005008893 W JP2005008893 W JP 2005008893W WO 2005113488 A1 WO2005113488 A1 WO 2005113488A1
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- surfactant
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- hydrogen atom
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 54
- 125000003709 fluoroalkyl group Chemical group 0.000 title claims abstract description 22
- 125000001183 hydrocarbyl group Chemical group 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 7
- 125000005647 linker group Chemical group 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 40
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 22
- 239000001569 carbon dioxide Substances 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 229920001774 Perfluoroether Polymers 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- -1 phosphate ester Chemical class 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LQUPKVMEAATBSL-UHFFFAOYSA-L zinc;2,3,4-trichlorophenolate Chemical compound [Zn+2].[O-]C1=CC=C(Cl)C(Cl)=C1Cl.[O-]C1=CC=C(Cl)C(Cl)=C1Cl LQUPKVMEAATBSL-UHFFFAOYSA-L 0.000 description 3
- INSCMIFABOJDRE-UHFFFAOYSA-N 2-(heptoxymethyl)oxirane Chemical compound CCCCCCCOCC1CO1 INSCMIFABOJDRE-UHFFFAOYSA-N 0.000 description 2
- MCFBUIIRFZBRCU-UHFFFAOYSA-N 4-[1-[5-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]pyridin-2-yl]piperidin-4-yl]oxycyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1OC1CCN(C=2N=CC(=CC=2)C=2NC3=CC(=CC=C3N=2)C(F)(F)F)CC1 MCFBUIIRFZBRCU-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- OJFKUJDRGJSAQB-UHFFFAOYSA-N TAK-632 Chemical compound C1=C(NC(=O)CC=2C=C(C=CC=2)C(F)(F)F)C(F)=CC=C1OC(C(=C1S2)C#N)=CC=C1N=C2NC(=O)C1CC1 OJFKUJDRGJSAQB-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- IBIKHMZPHNKTHM-RDTXWAMCSA-N merck compound 25 Chemical compound C1C[C@@H](C(O)=O)[C@H](O)CN1C(C1=C(F)C=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C1CC1 IBIKHMZPHNKTHM-RDTXWAMCSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/02—Alkyl sulfonates or sulfuric acid ester salts derived from monohydric alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
- C07C307/10—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/004—Surface-active compounds containing F
Definitions
- Branched surfactant having fluoroalkyl group and hydrocarbon group
- the present invention relates to a branched surfactant having a fluoroalkyl group and a hydrocarbon group.
- the surfactant of the present invention when used with liquid, subcritical or supercritical carbon dioxide, can improve its function as a solvent for chemical reaction, washing, extraction, staining and the like.
- wastewater treatment costs may be greatly reduced, and large wastewater treatment costs such as dyeing, plating, organic synthesis, chemical reaction, washing, and extraction will lead to industrial fields. The application of is particularly noticed.
- a surfactant is required for mixing the carbon dioxide and the polar conjugate.
- H (CF CF) (CH 2 CH 2) OOCCH (OSO Na) CH 2 COOR
- Patent Document 1 H (CF CF) is described in Patent Document 1 as an additive for improving the coating properties of photosensitive materials.
- CH OCH CH (OSO Na) R is patented as an additive to improve coating properties of photosensitive materials.
- Patent Document 3 It is described in Patent Document 3 as an antistatic material.
- Non-Patent Documents 1-3 There is a need for a hydrophobic group having a double-stranded or branched structure.
- Non-Patent Document 4 reports that C F CH (OSO Na) CH has a high function of taking up water into carbon dioxide.
- Non-Patent Documents 5 to 8 the synthesis of a stable and highly functional hybrid surfactant has been reported in recent years.
- these known hybrid surfactants exhibit sufficient functions in diacid carbon (Non-Patent Document 3).
- Non-Patent Document 9 Although the phosphate ester reported in Non-Patent Document 9 exhibits a high function in diacid carbon, the phosphate ester may be hydrolyzed and has a long-term stability. There are issues. Moreover, 0 which Make that the phosphoric acid esters are also insufficient functions by additional tests by the present inventors
- Patent Document 1 JP-A-51-32322
- Patent Document 2 Japanese Patent Publication No. 52-25087
- Patent Document 3 Japanese Patent Publication No. 52-26687
- Non-Patent Document l Progr, Colloid Polym, Sci. 2000, 115, 214
- Non-patent document 2 Langmulr 2001, 17 volumes, 274 pages
- Non-Patent Document 3 Langmuir 2003, 19 volumes, 220 pages
- Non-Patent Document 4 Langmuir 1994, 10 volumes, 3536 pages
- Non-Patent Document 5 Langmuirl 995, Vol. 11, p. 466
- Non-Patent Document 6 Abstracts of Lectures by the Oil Chemistry Symposium 2000, 305, 306
- Non-Patent Document 7 Abstracts of Lecture Meeting on Oil Chemistry 2002, 101 pages
- Non-Patent Document 8 J. Am. Chem. SOC. 2002, 124, 6516
- Non-Patent Document 9 J. Am. Chem. SOC. 2002, 124, 1834
- the present invention provides the following surfactants.
- Rf has an ether bond and may be a fluoroalkyl group, and Rh may be an alkyl group.
- r represents 1 or 0.
- Z 1 represents (CH 2) — (X 1 ) —
- Z 2 represents — (X 2 ) —.
- Z 1 represents (CH Y) —CH—
- Z 2 represents — (CH Y) —.
- X 1 and X 2 are the same or different and represent a divalent linking group, pi is 0 or 1, and ql is 0 or 1. nl represents an integer of 1 to 10.
- Y is 0, S or NR (R represents a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or t-butyl).
- p2 and q2 are not 0 at the same time but are 0 or 1.
- M represents a hydrogen atom, an alkali metal, 1Z2 alkaline earth metal or ammonium.
- Rf has an ether bond and may be a fluoroalkyl group
- Rh may be an alkyl group.
- X 1 and X 2 may be the same or different and represent a divalent linking group.
- Pi is 0 or 1
- ql is 0 or 1.
- nl represents an integer of 1 to 10.
- M represents a hydrogen atom, an alkali metal, 1Z2 alkaline earth metal or ammonium.
- Rf represents a (per) fluoroalkyl group, a (per) fluoroether group, or a (per) fluoropolyether group
- Rh represents an alkyl group
- Y is 0, S or NR (R represents a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or t-butyl).
- p2 and q2 are not 0 or 0 or 1 at the same time.
- M represents a hydrogen atom, an alkali metal, 1Z2 alkaline earth metal or ammonium.
- the water intake value is sufficiently high
- a surfactant having a sufficient micelle-forming ability can be provided.
- FIG. 1 (A) is a schematic view showing a device for measuring a W value.
- (B) is a detailed view cell view. In Fig. 1 (B), put the sample in the part "a".
- the surfactant of the present invention includes a polar compound such as CO (supercritical, subcritical or liquid) and water.
- organic compounds that handle polar compounds such as water using co2 as a solvent, and electrochemical reactions such as electroplating and plating, as well as efficiency improvements such as washing, staining, and extraction. .
- it is stable enough to withstand repeated use in CO-water systems.
- Such a surfactant is preferably a hybrid surfactant having a sulfate ester group or a sulfonic acid group, and having one fluoroalkyl group and one alkyl group.
- Examples of the polar conjugate to be mixed with the CO solvent include water, alcohol (methanol and ethanol).
- Water water-miscible organic solvents such as glycols such as DMF, DMSO, formamide, ethylene glycol, propylene glycol, etc., acetonitrile, THF, etc.
- a mixed solvent with a solvent is exemplified, and preferably, water is exemplified.
- Further examples include metal fine particles, inorganic salts, organic salts, and biological compounds such as phospholipids, saccharides, proteins, and carbohydrates.
- Rf is a fluoroalkyl group having an ether bond, and may be a linear or branched, specifically, (per) fluoroalkyl A (per) fluoroether group and a (per) fluoropolyether group.
- Rf has a carbon number of 4 to 50, and in the case of a fluoroalkyl group having no R1 ether bond, the carbon number is 4 to 20, preferably 5 to 18, more preferably 5 to 12, and a Ri ether bond.
- Q is 4 to 50, preferably 5 to 40, more preferably 5 to 35 in the case of a fluoroalkyl group having
- (Per) fluoroalkyl groups include:
- HC F (CH) (n represents an integer of 5 to 12, m represents an integer of 0 to 10) n 2n 2 m
- Rfl—O—Rf2 such as C F OCF (CF) —
- Rfl is a C to C linear or branched (per) fluoroalkyl group
- Examples of (per) fluoropolyether groups include CF OCF (CF) CF OCF (CF)-
- Rh is a linear or branched alkyl group having 3 to 18, preferably 4 to 12, and more preferably 4 to 10 carbon atoms.
- Preferred specific examples of Rh include (n-, sec-, iso-, tert_) butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl: C02 affinity portion (Rf) and hydrophilicity The balance of the group (Rh)
- M is a hydrogen atom, alkali metal (Na, K, Li, Cs), lZ2 alkaline earth metal (Ca, Mg, Ba), ammonium-NH (NH), quaternary ammonium-NR (NR; R is C1-C4 linear or branched
- Z 1 represents (CH 2) — (X 1 ) —
- Z 2 represents — (X 2 ) —.
- Len group for example, (CH2) m, (CF2) n, CF (CF3), (CF2) n (CH2), etc., m and n are integers of 1-3
- Preferred examples of the divalent linking group represented by X 1 and X 2 include the following.
- n represents an integer of 0 to 4, preferably 0 or 1)
- pl is 0 or 1.
- ql is 0 or 1.
- nl is an integer from 1 to: L0, preferably from 1 to 5.
- Z 1 represents (CH Y) —CH—
- Z 2 represents — (CH Y) —.
- Y is O, S or NR (R represents a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or t-butyl), preferably 0 or NR, more preferably It is 0.
- p2 and q2 are not 0 at the same time but are 0 or 1.
- the surfactant of the present invention is commercially available, and can be produced by known methods (for example, Patent Documents 1 to 3). It can be easily manufactured by those skilled in the art.
- the amount of the surfactant used in the present invention is about 0.001 to 2000 wt%, preferably about 0.01 to 1000 wt%, more preferably 0.01 to 500 wt% with respect to the polar compound handled in the aqueous solution or carbon dioxide. %, Especially about 0.1 to 100 wt%.
- Alcohols such as methanol, ethanol, propanol, butanol and pentanol; ketones such as acetone; esters such as acetonitrile and ethyl acetate; ethers such as ethyl ether; freons; methylene chloride; There are halides, especially those with low toxicity and low molecular weight are desirable.
- the amount of the surfactant to be used is different from that of a surfactant in a usual two-phase system, and the weight of the surfactant may be larger depending on the target polar conjugate. For example, when a metal salt or the like is used as a catalyst in C02 to carry out a chemical reaction, the amount of surfactant used may exceed 100 wt%.
- the surfactant of the present invention is characterized in that CO (liquid, subcritical, supercritical state) and water or a polar compound
- It is preferably used in a two-phase system between objects.
- Compounds having two fluoroalkyl groups (6A to 8A) were synthesized according to Bull. Chem. SOC. Jpn. 1991, 64, 3262.
- the product obtained by the 492 2 2 cal addition reaction was synthesized in a similar manner using the alcohol C F CH CH CH CH OH obtained by further reducing with lithium aluminum hydride. Further
- a surfactant is introduced into a portion of a in a pressure-resistant device (view cell) with a visible window in an amount of 2% by weight based on the amount of carbon dioxide.
- W value (number of water molecules / number of surfactant molecules) in micelle
- Water uptake weight of water dissolved in diacid carbon per lg of surfactant
- the hybrid type sulfonic acid ester having both a fluorine group having one carbon atom power or more in the molecule and a hydrocarbon chain having the same length as that in the molecule, and having a branched structure, is formed by diacid carbon. It can be seen that a high function is exhibited when handling a polar conjugated substance such as water.
- Compound 3B was synthesized from dodecafluoroheptyl glycidyl ether (3.88 g, 10 mmol) and hexanol (2.94 g, 30 mmol) in the same manner as in Example IB (3.1 g, two steps, 52%).
- W value (number of water molecules / number of surfactant molecules) in micelle
- Water uptake weight of water dissolved in diacid / carbon per lg of surfactant
- Water uptake weight of water dissolved in carbon dioxide per gram of surfactant
- the present inventor synthesized the above compounds 8B and 9B and evaluated them under the same conditions as the compound of the present invention. As a result, although compound 8B functions at relatively low pressure, water uptake of the compound was reported. It was much lower than the data!
- the compound of the present invention was found to be an excellent surfactant when handling a polar conjugate such as water in a medium using carbon dioxide as a solvent.
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Developing Agents For Electrophotography (AREA)
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05739356A EP1762566B1 (en) | 2004-05-20 | 2005-05-16 | Branched surfactant having fluoroalkyl group and hydrocarbon group |
DE602005027070T DE602005027070D1 (de) | 2004-05-20 | 2005-05-16 | Verzweigtes tensid mit fluoralkylgruppe und kohlenwasserstoffgruppe |
AT05739356T ATE502915T1 (de) | 2004-05-20 | 2005-05-16 | Verzweigtes tensid mit fluoralkylgruppe und kohlenwasserstoffgruppe |
US11/596,672 US7811473B2 (en) | 2004-05-20 | 2005-05-16 | Branched surfactant having fluoroalkyl group and hydrocarbon group |
US12/696,694 US7906042B2 (en) | 2004-05-20 | 2010-01-29 | Branched surfactant having fluoroalkyl group and hydrocarbon group |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP2004-149934 | 2004-05-20 | ||
JP2004149934A JP4497292B2 (ja) | 2004-05-20 | 2004-05-20 | フルオロアルキル基と炭化水素基を有する分岐型界面活性剤 |
JP2004-183077 | 2004-06-21 | ||
JP2004183077A JP4497297B2 (ja) | 2004-06-21 | 2004-06-21 | フルオロアルキル基と炭化水素基を有する分岐型界面活性剤 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US11/596,672 A-371-Of-International US7811473B2 (en) | 2004-05-20 | 2005-05-16 | Branched surfactant having fluoroalkyl group and hydrocarbon group |
US12/696,694 Division US7906042B2 (en) | 2004-05-20 | 2010-01-29 | Branched surfactant having fluoroalkyl group and hydrocarbon group |
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WO2005113488A1 true WO2005113488A1 (ja) | 2005-12-01 |
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PCT/JP2005/008893 WO2005113488A1 (ja) | 2004-05-20 | 2005-05-16 | フルオロアルキル基と炭化水素基を有する分岐型界面活性剤 |
Country Status (5)
Country | Link |
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US (2) | US7811473B2 (ja) |
EP (1) | EP1762566B1 (ja) |
AT (1) | ATE502915T1 (ja) |
DE (1) | DE602005027070D1 (ja) |
WO (1) | WO2005113488A1 (ja) |
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US7638650B2 (en) | 2007-08-06 | 2009-12-29 | E.I. Du Pont De Nemours And Company | Fluoroalkyl surfactants |
US7728163B2 (en) | 2007-08-06 | 2010-06-01 | E.I. Du Pont De Nemours And Company | Mixed fluoroalkyl-alkyl surfactants |
JP2018193373A (ja) * | 2012-07-18 | 2018-12-06 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | フッ素化界面活性剤 |
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US8173848B2 (en) * | 2008-07-01 | 2012-05-08 | E.I. Du Pont De Nemours And Company | Fluorinated alcohols |
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- 2005-05-16 DE DE602005027070T patent/DE602005027070D1/de active Active
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7638650B2 (en) | 2007-08-06 | 2009-12-29 | E.I. Du Pont De Nemours And Company | Fluoroalkyl surfactants |
US7728163B2 (en) | 2007-08-06 | 2010-06-01 | E.I. Du Pont De Nemours And Company | Mixed fluoroalkyl-alkyl surfactants |
US8242301B2 (en) | 2007-08-06 | 2012-08-14 | E. I. Du Pont De Nemours And Company | Mixed fluoroalkyl-alkyl surfactants |
JP2018193373A (ja) * | 2012-07-18 | 2018-12-06 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | フッ素化界面活性剤 |
Also Published As
Publication number | Publication date |
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US20080093582A1 (en) | 2008-04-24 |
US7811473B2 (en) | 2010-10-12 |
DE602005027070D1 (de) | 2011-05-05 |
US20100176345A1 (en) | 2010-07-15 |
ATE502915T1 (de) | 2011-04-15 |
EP1762566B1 (en) | 2011-03-23 |
EP1762566A1 (en) | 2007-03-14 |
US7906042B2 (en) | 2011-03-15 |
EP1762566A4 (en) | 2008-07-02 |
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