WO2017212803A1 - 非イオン界面活性剤 - Google Patents
非イオン界面活性剤 Download PDFInfo
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- WO2017212803A1 WO2017212803A1 PCT/JP2017/016051 JP2017016051W WO2017212803A1 WO 2017212803 A1 WO2017212803 A1 WO 2017212803A1 JP 2017016051 W JP2017016051 W JP 2017016051W WO 2017212803 A1 WO2017212803 A1 WO 2017212803A1
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- Prior art keywords
- ring
- nonionic surfactant
- formula
- carbon atoms
- group
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- 239000002736 nonionic surfactant Substances 0.000 title claims abstract description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 33
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract 3
- 239000003995 emulsifying agent Substances 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 30
- 239000012459 cleaning agent Substances 0.000 claims description 18
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 16
- 235000011187 glycerol Nutrition 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 230000001804 emulsifying effect Effects 0.000 abstract description 13
- 230000003381 solubilizing effect Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 25
- -1 aliphatic alcohols Chemical class 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 229910001868 water Inorganic materials 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003513 alkali Substances 0.000 description 14
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- 238000000034 method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 3
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- 229920003002 synthetic resin Polymers 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- LQXBZWFNAKZUNM-UHFFFAOYSA-N 16-methyl-1-(16-methylheptadecoxy)heptadecane Chemical compound CC(C)CCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC(C)C LQXBZWFNAKZUNM-UHFFFAOYSA-N 0.000 description 2
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000036541 health Effects 0.000 description 2
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- 230000007062 hydrolysis Effects 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/678—Tocopherol, i.e. vitamin E
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
-
- 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
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
Definitions
- the present invention relates to a nonionic surfactant that exhibits an excellent emulsifying action for various oils and solvents.
- Alkylphenol ethoxylates such as octylphenol ethoxylate and nonylphenol ethoxylate obtained by addition polymerization of ethylene oxide with alkylphenol are aromatic nonionic surfactants having excellent surface activity.
- these compounds and their decomposition products alkylphenol, short-chain alkylphenol ethoxylate, etc.
- oxides have recently been feared for adverse effects on the environment and ecosystems.
- polyalkylene oxide chains obtained by the addition polymerization of C2-C4 alkylene oxides such as ethylene oxide to aliphatic alcohols are hydrophilic.
- An aliphatic nonionic surfactant having a functional group is used (see Patent Document 1).
- the aliphatic nonionic surfactant has a problem that its surface activity tends to decrease with time. This is because, when an aliphatic hydrocarbon group is included as a hydrophobic group, the association force between the polyalkylene oxide chain, which is a hydrophilic group, and water is weak, and the hydrophilicity (or affinity for water) decreases with time. It was because it was easy.
- a nonionic interface that is environmentally friendly, has an excellent surface active action comparable to alkylphenol ethoxylates such as octylphenol ethoxylate and nonylphenol ethoxylate, and can stably maintain the excellent surface active ability over time At present, no active agent has been found.
- an object of the present invention is a nonionic surfactant that is environmentally friendly, has excellent surface activity (emulsification power, solubilization power), and can maintain the excellent surface activity stably over time. Is to provide.
- a nonionic surfactant having a polyalkylene oxide chain as a hydrophilic group is a compound that exhibits hydrophilicity by hydrogen bonding with water molecules, so Although it is easily affected and its hydrophilicity tends to decrease with temperature, nonionic surfactants with polyglycerin chains as hydrophilic groups show stable hydrophilicity over a wide temperature range, and surface activity over time
- a nonionic surfactant comprising a polyglycerin chain as a hydrophilic group and an aryl group having an aliphatic hydrocarbon group having a specific chain length as a hydrophobic group Compared to nonionic surfactants with a polyglycerin chain as a hydrophilic group and an aliphatic hydrocarbon group as a hydrophobic group, it exhibits even better surface activity. It found that it is possible to suppress further reduce the decrease in the surface activity of. The present invention has been completed based on these findings and further research.
- ring Z represents a condensed ring of an aromatic hydrocarbon ring having 6 to 14 carbon atoms and a 3 to 6 membered heterocyclic ring containing an oxygen atom as a hetero atom.
- R 1 is bonded to ring Z.
- a substituent which is an aliphatic hydrocarbon group having 14 to 25 carbon atoms, and the ring Z may have one or more other substituents in addition to R 1 , and n is glycerin.
- the average number of isomers is 2 to 20
- the nonionic surfactant containing the polyglycerol monoether represented by these is provided.
- the present invention also provides the heterocyclic moiety in ring Z, wherein R 1 is a condensed ring of an aromatic hydrocarbon ring having 6 to 14 carbon atoms and a 3 to 6 membered heterocyclic ring containing an oxygen atom as a hetero atom.
- a nonionic surfactant as described above is provided, which is a substituent bonded to the above-mentioned nonionic surfactant.
- the present invention also provides the nonionic surfactant, wherein the polyglycerol monoether represented by the formula (1) is a compound represented by the following formula (1-1) or (1-2): To do. (Wherein R 2 , R 3 and R 4 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a hydroxyl group. N is the average number of glycerin monomers; 20 indicates the number)
- the present invention also provides the nonionic surfactant used as a cleaning agent.
- the present invention also provides the nonionic surfactant used as an emulsifier.
- the present invention also provides the nonionic surfactant used as an emulsifier for emulsion polymerization.
- the present invention also provides the nonionic surfactant described above for use as a solubilizer.
- ring Z represents a condensed ring of an aromatic hydrocarbon ring having 6 to 14 carbon atoms and a 3- to 6-membered heterocycle containing an oxygen atom as a hetero atom.
- R 1 is a substituent bonded to ring Z and represents an aliphatic hydrocarbon group having 14 to 25 carbon atoms, and ring Z has one or more other substituents in addition to R 1 .
- N is an average number of glycerin monomers, and represents a number of 2 to 20).
- R 1 is bonded to the heterocyclic moiety in ring Z, which is a condensed ring of an aromatic hydrocarbon ring having 6 to 14 carbon atoms and a 3 to 6-membered heterocyclic ring containing an oxygen atom as a hetero atom.
- the heterocyclic ring constituting the ring Z is a 4- to 6-membered heterocyclic ring, a 5- or 6-membered heterocyclic ring, or a 6-membered heterocyclic ring, according to any one of [1] to [4] Nonionic surfactant.
- the nonionic surfactant as described in.
- substituents in ring Z are alkyl groups having 1 to 5 carbon atoms, halogen atoms, oxo groups, hydroxyl groups, alkoxy groups having 1 to 5 carbon atoms, carboxyl groups, and alkoxy having 1 to 5 carbon atoms.
- the number of other substituents in the ring Z is 0 to 12, 1 to 8, 2 to 6, or 3 to 5 [1] to any one of [8] Nonionic surfactant.
- the polyglycerin monoether represented by the formula (1) is the above formula (1-1) or (1-2) (wherein R 2 , R 3 , R 4 are the same or different and hydrogen An atom, an alkyl group having 1 to 5 carbon atoms, or a hydroxyl group, wherein n is an average number of glycerin monomers and represents a number of 2 to 20) [1] to [10]
- the nonionic surfactant as described in any one of these.
- the nonionic surfactant according to any one of [1] to [12] which is used as an emulsifier.
- the nonionic surfactant of the present invention has a configuration in which a specific hydrophilic group and a specific hydrophobic group are combined, a change in hydrophilicity due to a temperature change is suppressed, and a variety of mineral oil, vegetable oil, silicone oil, etc. It has excellent surface active action (emulsifying power, solubilizing power) comparable to alkylphenol ethoxylates such as octylphenol ethoxylate and nonylphenol ethoxylate for oils, solvents and synthetic resins. The surface active ability can be maintained stably over time (for example, 30 days or more, preferably 40 days or more, more preferably 60 days or more). It is also environmentally friendly. Therefore, the nonionic surfactant of the present invention is useful as a cleaning agent, an emulsifier, an emulsifier for emulsion polymerization, or a solubilizer.
- the nonionic surfactant of the present invention contains a polyglycerin monoether represented by the following formula (1).
- the ring Z having the substituent R 1 in the following formula (1) is a hydrophobic group, and the polyglycerin chain is a hydrophilic group.
- ring Z represents a condensed ring of an aromatic hydrocarbon ring having 6 to 14 carbon atoms and a 3 to 6 membered heterocyclic ring containing an oxygen atom as a hetero atom.
- R 1 is bonded to ring Z.
- a substituent which is an aliphatic hydrocarbon group having 14 to 25 carbon atoms, and the ring Z may have one or more other substituents in addition to R 1 , and n is glycerin.
- the average number of isomers is 2 to 20)
- the aromatic hydrocarbon ring having 6 to 14 carbon atoms constituting the ring Z is preferably an aromatic hydrocarbon ring having 6 to 10 carbon atoms, and examples thereof include a benzene ring and a naphthalene ring.
- the 3- to 6-membered heterocycle containing an oxygen atom as a heteroatom constituting the ring Z is a heterocycle containing at least an oxygen atom as a heteroatom, and may contain a heteroatom other than the oxygen atom.
- a heterocyclic ring include a 3-membered ring such as an oxirane ring; a 4-membered ring such as an oxetane ring; a 5-membered ring such as a furan ring, tetrahydrofuran ring, oxazole ring, isoxazole ring, and ⁇ -butyrolactone ring; 4 Examples thereof include 6-membered rings such as -oxo-4H-pyran ring, tetrahydropyran ring and morpholine ring.
- R 1 represents an aliphatic hydrocarbon group having 14 to 25 carbon atoms, and the upper limit of the carbon number is preferably 23, particularly preferably 22, and most preferably 20. Further, the lower limit of the carbon number is preferably 15, particularly preferably 16.
- the aliphatic hydrocarbon group includes a linear or branched aliphatic hydrocarbon group. In the present invention, among these, branched aliphatic hydrocarbon groups (branched saturated or unsaturated aliphatic hydrocarbon groups) are preferable in terms of water solubility, and in particular, branched alkyl groups or branched alkenyls. Groups are preferred.
- R 1 is a substituent bonded to the ring Z, and the ring Z in the ring Z which is a condensed ring of an aromatic hydrocarbon ring having 6 to 14 carbon atoms and a 3 to 6 membered heterocycle containing an oxygen atom as a hetero atom. It may be bonded to the aromatic hydrocarbon ring portion or may be bonded to the heterocyclic portion. In the present invention, it is particularly preferable that R 1 has a configuration in which it is bonded to the heterocyclic moiety in the ring Z.
- Ring Z may have one or more other substituents in addition to R 1 .
- substituents include an alkyl group having 1 to 5 carbon atoms, a halogen atom, an oxo group, a hydroxyl group, an alkoxy group having 1 to 5 carbon atoms, a carboxyl group, and an alkoxycarbonyl group having 1 to 5 carbon atoms. Can be mentioned. These can be used alone or in combination of two or more.
- the number of other substituents in the ring Z is not particularly limited, but is, for example, 0 to 12, preferably 1 to 8, more preferably 2 to 6, and further preferably 3 to 5.
- the hydrophobic group in the polyglycerin monoether represented by the formula (1) among them, the group represented by the following formula (z-1) or (z-2) is environmentally friendly and has a surface activity.
- a residue obtained by removing a hydroxyl group from the structural formula of tocopherol or tocotrienol is preferable.
- the polyglycerol monoether represented by the formula (1) is preferably a compound represented by the following formula (1-1) or (1-2), and in particular, a polyglycerol monotocopheryl ether or a polyglycerol monotocotriate.
- Enil ether is preferred.
- R 2 , R 3 and R 4 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a hydroxyl group.
- N is the average number of glycerin monomers; 20 indicates the number
- alkyl group having 1 to 5 carbon atoms examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group and the like.
- n is the average number of glycerin monomers and represents a number of 2 to 20. n is preferably a number of 5 to 20, particularly preferably a number of 8 to 15.
- the nonionic surfactant of the present invention may contain one kind of polyglycerin monoether represented by the above formula (1), or may contain two or more kinds in combination.
- the nonionic surfactant of the present invention can be produced by various methods, for example, (I) Following formula (2) (In the formula, ring Z and R 1 are the same as above. In addition, ring Z may have one or more other substituents in addition to R 1. ) A method of addition polymerization of epichlorohydrin to an alcohol represented by (for example, tocopherol, tocotrienol, etc.) (Ii) A method of subjecting the alcohol represented by the formula (2) to addition polymerization of glycidol.
- the polyglycerol monoether represented by Formula (1) can be selectively manufactured.
- nonionic surfactant containing polyglycerin monoether represented by formula (1) with high purity is a nonionic surfactant having a low polyglycerin monoether concentration represented by formula (1).
- the amount of use can be suppressed as compared with the surfactant, and an increase in environmental load due to excessive use of the surfactant, rough skin, and the like can be suppressed.
- the method of adding glycidol to the alcohol represented by the formula (2) is performed by a method in which an alkali catalyst is added to the alcohol represented by the formula (2) to form an alkoxide, and then glycidol is added to cause a dehydration condensation reaction. be able to.
- the alkali catalyst used in the present invention is preferably a compound that easily removes the residue after the alcohol represented by formula (2) is converted into an alkoxide.
- the alkali catalyst include basic compounds obtained by substituting a part of protons in a protic solvent with an alkali metal or alkaline earth metal cation (for example, potassium hydroxide, sodium hydroxide, lithium hydroxide, magnesium hydroxide, water Calcium oxide, sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, butoxypotassium, butoxysodium, etc.), basic compounds obtained by substituting a part of the saturated hydrocarbon with an alkali metal or alkaline earth metal cation (for example, , Butyl lithium, methyl lithium, ethyl lithium, etc.), basic metals (for example, sodium, potassium, lithium, etc.) and the like. These can be used alone or in combination of two or more.
- the amount of the alkali catalyst used is, for example, 4 to 40 mol%, preferably 5 to 30 mol%, based on the alcohol represented by the formula (2).
- amount of the alkali catalyst used is less than 4 mol%, glycidol tends to be self-polymerized before reacting with the alkoxide to easily produce polyglycerol as a by-product.
- usage-amount of an alkali catalyst exceeds 40 mol%, there exists a tendency for many reduction products to byproduce.
- the alkali catalyst it is preferable to add the alkali catalyst to the alcohol represented by the formula (2) before adding glycidol. Further, the alkali catalyst can be added to the reaction system all at once or dividedly. Furthermore, after the addition of the alkali catalyst, the alkoxideation can be promoted while distilling water under heating or reduced pressure heating to promote the conversion of the alcohol represented by the formula (2) to the alkoxide. This is preferable.
- reaction of dehydrating and condensing glycidol to alkoxide is preferably performed under an inert gas stream (for example, under a nitrogen gas stream) in order to suppress hydrolysis of the alkoxide.
- an inert gas stream for example, under a nitrogen gas stream
- polyglycerin tends to be easily produced as a by-product using the alkali compound produced thereby as an initiator.
- the reaction may be pressurized as necessary.
- the reaction temperature of the above reaction is, for example, 0 to 150 ° C., preferably 60 to 140 ° C., more preferably 80 to 130 ° C.
- the reaction temperature is less than 0 ° C., it is difficult to stir the reaction system, and the progress of the reaction may be inhibited.
- the reaction temperature exceeds 150 ° C., glycidol tends to be self-polymerized before reacting with the alkoxide to easily produce polyglycerin.
- a low-boiling compound having a low reactivity with glycidol or an inert solvent may be added for the purpose of preventing the reaction temperature from rising and reducing the viscosity of the reaction solution.
- a compound or solvent include acetone, ethyl acetate, butyl acetate, hexane, toluene, xylene and the like. These can be used individually by 1 type or in combination of 2 or more types.
- the obtained reaction product can be separated and purified by separation means such as filtration, concentration, distillation, extraction, crystallization, adsorption, recrystallization, column chromatography, etc., or a combination means combining these.
- the reaction product contains an alkali catalyst or a salt thereof, but a purification treatment for removing these may be performed. It is preferable in terms of health and safety and the environment.
- the purification treatment it is preferable to neutralize the alkali catalyst with an acid and remove the deposited alkali metal or alkaline earth metal salt by filtration treatment.
- Examples of the acid used for neutralizing the alkali catalyst include inorganic acids such as phosphoric acid, sulfuric acid, hydrochloric acid and nitric acid; and organic acids such as formic acid, acetic acid, butyric acid and valeric acid. These can be used alone or in combination of two or more. In the present invention, it is preferable to use an inorganic acid, and hydrochloric acid and / or phosphoric acid are particularly preferable.
- the reaction product it is preferable to neutralize the alkali catalyst with an acid and then subject the reaction product to a distillation treatment to remove low-boiling components before subjecting it to a filtration treatment.
- the distillation treatment is preferably performed under an inert gas stream or under reduced pressure in order to prevent by-products due to oxidation or the like.
- the reaction product when the viscosity of the reaction product is high, in order to improve the efficiency of the filtration treatment, the reaction product is a poor solvent for the salt and a good solvent for the polyglycerol monoether represented by the formula (1). (E.g., if the filtration equipment uses a filter press capable of pressurization at a pressure of 4 kg / cm ⁇ 2 >, lower the viscosity of the reaction product to 30 cps or less) It may be filtered.
- solvent used for diluting the reaction product examples include polar solvents such as alcohols; nonpolar solvents such as pentane, hexane, octane, benzene, acetone, ethyl acetate, and diethyl ether. These can be used alone or in combination of two or more.
- a polar solvent is preferable, and alcohols are particularly preferable.
- the alcohols include saturated aliphatic alcohols (for example, methanol, ethanol, etc.), unsaturated aliphatic alcohols, aromatic alcohols (for example, phenol). Also included are alcohols having linear, branched and cyclic structures. Furthermore, polyhydric alcohols such as dihydric alcohols are also included. In the present invention, an alcohol having 1 to 8 carbon atoms is particularly preferable, and an alcohol having 1 to 4 carbon atoms is particularly preferable.
- the nonionic surfactant of the present invention obtained by the above production method may be further subjected to purification treatment as necessary.
- the purification method include (a) a deodorization method in which saturated heating steam is blown under reduced pressure to perform steam deodorization, and (b) a decolorization method such as bleaching with sodium hypophosphite or hydrogen peroxide.
- the nonionic surfactant according to the present invention contains at least a polyglycerol monoether represented by the above formula (1).
- the proportion of the polyglycerol monoether represented by the formula (1) in the total nonvolatile content (100 wt%) of the nonionic surfactant according to the present invention is, for example, 75 wt% or more, preferably 80 wt% or more, particularly Preferably it is 85 weight% or more, Most preferably, it is 90 weight% or more.
- the upper limit is 100% by weight.
- the nonionic surfactant according to the present invention may contain polyglycerin, and the content of polyglycerin is, for example, the non-volatile amount of the nonionic surfactant according to the present invention (100% by weight), for example, It is 20 wt% or less, preferably 10 wt% or less.
- the content of polyglycerin exceeds the above range, the water dispersibility of the nonionic surfactant according to the present invention tends to decrease.
- the nonionic surfactant according to the present invention may further contain a polyglycerin polyether such as polyglycerin diether or polyglycerin triether, but the content of polyglycerin polyether (when two or more are contained) The total amount) is, for example, 5% by weight or less, preferably 1% by weight or less of the total nonvolatile content (100% by weight) of the nonionic surfactant according to the present invention.
- the content of the polyglycerin polyether exceeds the above range, the water dispersibility of the nonionic surfactant according to the present invention tends to decrease.
- the nonionic surfactant according to the present invention is excellent in solubility in water. Therefore, even if the nonionic surfactant according to the present invention contains water (for example, water is added to the polyglycerol monoether represented by the formula (1), for example, 70:30 to 99.9: 0.1 [polyglycerin monoether represented by the formula (1): water (weight ratio)]), appearance and uniformity can be maintained well.
- water for example, water is added to the polyglycerol monoether represented by the formula (1), for example, 70:30 to 99.9: 0.1 [polyglycerin monoether represented by the formula (1): water (weight ratio)]
- the nonionic surfactant according to the present invention may further contain one or more other components as long as the effects of the present invention are not impaired.
- the other components include surfactants other than the polyglycerol monoether represented by the formula (1) (for example, sodium polyoxyethylene alkyl ether sulfate having an average addition mole number of 5 to 10, sucrose fatty acid ester, Glycerin fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid monoethanolamide, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, carboxybetaine type amphoteric surfactant, imidazolinium type Amphoteric surfactants, sulfobetaine type amphoteric surfactants, alanine type amphoteric surfactants, etc.), builders (eg, sodium pyrophosphate, sodium tripolyphosphate, zeolite, sodium citrate,
- the nonionic surfactant according to the present invention exhibits excellent emulsifying power or solubilizing power for various oils and solvents having a kinematic viscosity at 25 ° C. of, for example, about 0.1 to 3000 mm 2 / s. .
- it can be suitably used as an emulsifier for mineral oils, vegetable oils, aliphatic hydrocarbon solvents, alicyclic hydrocarbon solvents, and aromatic hydrocarbon solvents.
- emulsifiers and dispersants for synthetic resins such as silicones, modified silicones, polyolefins, polyesters, diene polymers (eg, polybutadiene, etc.), and emulsifiers and solubilizers for essential oils and fragrances Etc.
- synthetic resins such as silicones, modified silicones, polyolefins, polyesters, diene polymers (eg, polybutadiene, etc.), and emulsifiers and solubilizers for essential oils and fragrances Etc.
- it can also be suitably used as an emulsifier for emulsion polymerization of monomers such as acrylic monomers, styrene monomers, diene monomers and vinyl monomers.
- the nonionic surfactant according to the present invention can exhibit very excellent performance as a cleaning agent in various applications and fields.
- industrial and commercial cleaners, automotive cleaners, industrial process chemicals for example, fiber refining agents, metal surface treatment agents, metal degreasing agents, metal component cleaners, electronic component cleaners, leather Cleaning agents, depitching agents, linen supply related cleaning agents, dry cleaning additives, etc.
- kitchen cleaning agents for example, finger cleaning agents, skin cleaning agents, hair cleaning agents and the like.
- the nonionic surfactant according to the present invention can exhibit a very excellent detergency against mineral oil stains, vegetable oil stains, soils to which inorganic substances, waxes, and resins are attached.
- the nonionic surfactant according to the present invention can maintain a stable surface activity over a long period of time and can suppress phase separation over time. Moreover, since the polyglycerin monoether represented by the above formula (1) is contained (for example, 75% by weight or more), the amount of the surfactant used can be kept to a minimum, and the environment due to excessive use. The occurrence of problems such as contamination and rough skin can be suppressed.
- Emulsifier, Solubilizer, Emulsifier for Emulsion Polymerization, Detergent Since the nonionic surfactant which concerns on this invention has the said characteristic, it can be used conveniently as an emulsifier, a solubilizer, an emulsifier for emulsion polymerization, a washing
- the emulsifier, solubilizer, emulsion polymerization emulsifier, or cleaning agent in the present invention contains at least the nonionic surfactant.
- the proportion of the polyglycerol monoether represented by the formula (1) in the total nonvolatile content (100 wt%) of the emulsifier, the solubilizer, the emulsifier for emulsion polymerization, or the detergent of the present invention is, for example, 75 wt% or more, Preferably it is 80 weight% or more, Most preferably, it is 85 weight% or more. The upper limit is 100% by weight.
- the emulsifier, the solubilizer, the emulsion polymerization emulsifier, or the cleaning agent in the present invention may contain polyglycerin, and the content of polyglycerin is the emulsifier, the solubilizer, the emulsion polymerization emulsifier in the present invention. Or, for example, 20% by weight or less, preferably 10% by weight or less, of the total nonvolatile content (100% by weight) of the cleaning agent. When the content of polyglycerin exceeds the above range, the water dispersibility of the emulsifier, the solubilizer, the emulsifier for emulsion polymerization, or the detergent in the present invention tends to decrease.
- the emulsifier, the solubilizer, the emulsifier for emulsion polymerization, or the detergent in the present invention may further contain a polyglycerin polyether such as polyglycerin diether or polyglycerin triether, but it contains polyglycerin polyether.
- the amount is, for example, 5% by weight or less, preferably 1% by weight or less of the total nonvolatile content (100% by weight) of the emulsifier, solubilizer, emulsifier for emulsion polymerization, or cleaning agent in the present invention.
- the content of the polyglycerin polyether exceeds the above range, the water dispersibility of the emulsifier, the solubilizer, the emulsifier for emulsion polymerization, or the detergent in the present invention tends to decrease.
- HPLC analysis conditions HPLC body: Waters 2690 (Waters) Column: Wakosil 5C18 (manufactured by Wako Pure Chemical Industries, Ltd .; reverse phase distribution column having octadecylsilyl group as a functional group) Developing solvent: Methanol flow rate: 0.5 mL / min Column oven temperature: 40 ° C. Detection method: RI Sample concentration: 5% (solvent: methanol) Injection volume: 10 ⁇ L The retention time of each component is 6 minutes for polyglycerol, 10 to 25 minutes for polyglycerol monotocopheryl ether, and 28 to 40 minutes for polyglycerol ditocopheryl ether.
- Production Example 1 A four-necked flask was charged with 430.79 g (1.0 mol) of dl- ⁇ -tocopherol and 4.08 g (0.05 mol) of sodium hydroxide. Next, for the purpose of removing water in the reaction system, the pressure was reduced to 10 mmHg using an aspirator while heating at 100 ° C. for 90 minutes. Thereafter, the inside of the reaction system was returned to normal pressure, and 740.08 g (10 mol) of glycidol was added dropwise over 20 hours while maintaining the reaction temperature at 130 ° C. while sufficiently stirring the reaction solution under nitrogen flow.
- reaction solution (1) 85% by weight phosphoric acid aqueous solution is added to the reaction solution to neutralize to pH 7, and the inside of the reaction system is depressurized while heating again to distill off low-boiling components.
- the average number of glycerin monomers (n) of the compound in the obtained reaction solution (1) was about 10.1 (by 1 H-NMR analysis).
- the reaction solution (1) was separated by HPLC (high performance liquid chromatography) and the peak area was calculated with an infrared absorption detector, the area ratio of polyglycerol to polyglycerol monotocopheryl ether (the former: the latter) was 6. 5: 93.5, and the polyglycerol ditocopheryl ether content was 0.5% or less (below the detection limit).
- Example 1 0.4 g of the reaction liquid (1) obtained in Production Example 1 (polyglycerin monotocopheryl ether content: 95% by weight), silicon oil as an oil to be emulsified (dimethylpolysiloxane, kinematic viscosity at 25 ° C .: 1000 mm 2 / S) Take 4.0 g in a graduated test tube, stir with a test tube touch mixer (IWAKI) for 30 seconds, then add 5.6 mL of distilled water at 25 ° C., and further with a test tube touch mixer for 1 minute.
- silicon oil as an oil to be emulsified
- Emulsifying power (%) [amount of charged water (5.6 mL) ⁇ amount of water separation layer (mL)] / amount of charged water (5.6 mL) ⁇ 100 (5)
- Example 1 The results of Example 1 and Comparative Examples 1 to 4 are summarized in the following table.
- Example 2 The emulsifying power (%) of the reaction liquid (1) was calculated in the same manner as in Example 1 except that 4.0 g of liquid paraffin (kinematic viscosity at 25 ° C .: 9.8 mm 2 / s) was used as the oil to be emulsified. .
- Example 3 The emulsifying power (%) of the reaction liquid (1) was calculated in the same manner as in Example 1 except that 4.0 g of olive oil (kinematic viscosity at 25 ° C .: 80.1 mm 2 / s) was used as the oil to be emulsified. .
- the nonionic surfactant of the present invention has a configuration in which a specific hydrophilic group and a specific hydrophobic group are combined, a change in hydrophilicity due to a temperature change is suppressed, and a variety of mineral oil, vegetable oil, silicone oil, etc. It has excellent surface active action (emulsifying power, solubilizing power) comparable to alkylphenol ethoxylates such as octylphenol ethoxylate and nonylphenol ethoxylate for oils, solvents and synthetic resins. The surface active ability can be maintained stably over time (for example, 30 days or more, preferably 40 days or more, more preferably 60 days or more). It is also environmentally friendly. Therefore, the nonionic surfactant of the present invention is useful as a cleaning agent, an emulsifier, an emulsifier for emulsion polymerization, or a solubilizer.
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Abstract
Description
(式中、環Zは、炭素数6~14の芳香族炭化水素環と、ヘテロ原子として酸素原子を含む3~6員の複素環との縮合環を示す。R1は環Zに結合する置換基であり、炭素数14~25の脂肪族炭化水素基を示す。また、環ZはR1以外にも他の置換基を1個又は2個以上有していてもよい。nはグリセリンの平均量体数であり、2~20の数を示す)
で表されるポリグリセリンモノエーテルを含む非イオン界面活性剤を提供する。
(式中、R2、R3、R4は、同一又は異なって、水素原子、炭素数1~5のアルキル基、又はヒドロキシル基を示す。nはグリセリンの平均量体数であり、2~20の数を示す)
[1]前記式(1)(式中、環Zは、炭素数6~14の芳香族炭化水素環と、ヘテロ原子として酸素原子を含む3~6員の複素環との縮合環を示す。R1は環Zに結合する置換基であり、炭素数14~25の脂肪族炭化水素基を示す。また、環ZはR1以外にも他の置換基を1個又は2個以上有していてもよい。nはグリセリンの平均量体数であり、2~20の数を示す)で表されるポリグリセリンモノエーテルを含む非イオン界面活性剤。
[2]R1が、炭素数6~14の芳香族炭化水素環と、ヘテロ原子として酸素原子を含む3~6員の複素環との縮合環である環Zにおける前記複素環部分に結合する置換基である、[1]に記載の非イオン界面活性剤。
[3]環Zを構成する芳香族炭化水素環の炭素数が6~10である[1]又は[2]に記載の非イオン界面活性剤。
[4]環Zを構成する芳香族炭化水素環がベンゼン環、又はナフタレン環である[1]~[3]の何れか1つに記載の非イオン界面活性剤。
[5]環Zを構成する複素環が4~6員の複素環、5若しくは6員の複素環、又は6員の複素環である[1]~[4]の何れか1つに記載の非イオン界面活性剤。
[6]R1の脂肪族炭化水素基の炭素数の上限が、23、22、又は20であり、炭素数の下限が、15又は16である[1]~[5]の何れか1つに記載の非イオン界面活性剤。
[7]環Zにおける他の置換基が、炭素数1~5のアルキル基、ハロゲン原子、オキソ基、ヒドロキシル基、炭素数1~5のアルコキシ基、カルボキシル基、及び炭素数1~5のアルコキシカルボニル基からなる群より選択される少なくとも1つである[1]~[6]の何れか1つに記載の非イオン界面活性剤。
[8]環Zにおける他の置換基が、炭素数1~5のアルキル基である[1]~[7]の何れか1つに記載の非イオン界面活性剤。
[9]環Zにおける他の置換基の数が、0~12個、1~8個、2~6個、又は3~5個である[1]~[8]の何れか1つに記載の非イオン界面活性剤。
[10]nが5~20の数、又は8~15の数である[1]~[9]の何れか1つに記載の非イオン界面活性剤。
[11]式(1)で表されるポリグリセリンモノエーテルが、前記式(1-1)又は(1-2)(式中、R2、R3、R4は、同一又は異なって、水素原子、炭素数1~5のアルキル基、又はヒドロキシル基を示す。nはグリセリンの平均量体数であり、2~20の数を示す)で表される化合物である[1]~[10]の何れか1つに記載の非イオン界面活性剤。
[12]洗浄剤として使用する、[1]~[11]の何れか1つに記載の非イオン界面活性剤。
[13]乳化剤として使用する、[1]~[12]の何れか1つに記載の非イオン界面活性剤。
[14]乳化重合用乳化剤として使用する、[1]~[13]の何れか1つに記載の非イオン界面活性剤。
[15]可溶化剤として使用する、[1]~[14]の何れか1つに記載の非イオン界面活性剤。
本発明の非イオン界面活性剤は、下記式(1)で表されるポリグリセリンモノエーテルを含む。下記式(1)中の置換基R1を有する環Zが疎水性基であり、ポリグリセリン鎖が親水性基である。
(式中、環Zは、炭素数6~14の芳香族炭化水素環と、ヘテロ原子として酸素原子を含む3~6員の複素環との縮合環を示す。R1は環Zに結合する置換基であり、炭素数14~25の脂肪族炭化水素基を示す。また、環ZはR1以外にも他の置換基を1個又は2個以上有していてもよい。nはグリセリンの平均量体数であり、2~20の数を示す)
(式中、R2、R3、R4は、同一又は異なって、水素原子、炭素数1~5のアルキル基、又はヒドロキシル基を示す)
(式中、R2、R3、R4は、同一又は異なって、水素原子、炭素数1~5のアルキル基、又はヒドロキシル基を示す。nはグリセリンの平均量体数であり、2~20の数を示す)
-CH2-CHOH-CH2O- (a)
-CH(CH2OH)CH2O- (b)
(i) 下記式(2)
(式中、環Z、R1は上記に同じ。また、環ZはR1以外にも他の置換基を1個又は2個以上有していてもよい。)
で表されるアルコール(例えば、トコフェロール、トコトリエノール等)にエピクロルヒドリンを付加重合する方法や、
(ii) 前記式(2)で表されるアルコールにグリシドールを付加重合する方法
等が挙げられる。
本発明に係る非イオン界面活性剤は上記特性を有するため、例えば、乳化剤、可溶化剤、乳化重合用乳化剤、洗浄剤等として好適に使用することができる。
HPLC本体:Waters2690(Waters社製)
カラム:Wakosil 5C18(和光純薬工業(株)製;オクタデシルシリル基を官能基として持つ逆相分配カラム)
展開溶媒:メタノール
流速:0.5mL/分
カラムオーブン温度:40℃
検出方法:RI
試料濃度:5%(溶媒:メタノール)
注入量:10μL
各成分のリテンションタイムは、ポリグリセリンが6分、ポリグリセリンモノトコフェリルエーテルが10分~25分、ポリグリセリンジトコフェリルエーテルが28分~40分である。
dl-α-トコフェロール430.79g(1.0モル)と水酸化ナトリウム4.08g(0.05モル)とを4つ口フラスコに仕込んだ。次に、反応系内の水分を除去する目的で、90分間、100℃に加熱しながらアスピレーターを使用して10mmHgまで減圧した。その後、反応系内を常圧に戻し、窒素流通下、反応液を十分撹拌しながら、反応温度を130℃に保持した状態で、グリシドール740.08g(10モル)を20時間かけて滴下した。次に、反応液に85重量%リン酸水溶液を添加してpH7に中和し、再び、加熱しながら反応系内を減圧にして、低沸点成分を留去し、その後、濾過により中和塩を除去して、反応液(1)を得た。
得られた反応液(1)中の化合物の平均グリセリン量体数(n)は約10.1であった(1H-NMR分析による)。
反応液(1)をHPLC(高速液体クロマトグラフィー)で分離し、赤外線吸収検出器でピーク面積を算出したところ、ポリグリセリンとポリグリセリンモノトコフェリルエーテルの面積比(前者:後者)は、6.5:93.5であり、ポリグリセリンジトコフェリルエーテル含有量は0.5%以下(検出限界以下)であった。
製造例1で得られた反応液(1)(ポリグリセリンモノトコフェリルエーテル含有量:95重量%)0.4g、被乳化油としてのシリコンオイル(ジメチルポリシロキサン、25℃における動粘度:1000mm2/s)4.0gを目盛り付き試験管にとり、試験管用タッチミキサー(IWAKI社製)で30秒間撹拌し、次いで、25℃の蒸留水5.6mLを加えて、さらに試験管用タッチミキサーで1分間撹拌した後、2時間静置し、離水層の量(mL)を試験管についている目盛りを使用して測定し、下記式(5)から乳化力(%)を算出した。
乳化力(%)=[仕込み水量(5.6mL)-離水層の量(mL)]/仕込み水量(5.6mL)×100 (5)
製造例1で得られた反応液(1)に代えて、ポリグリセリンモノイソステアリルエーテル((株)ダイセル製、モノエーテル体含有率:90重量%、平均グリセリン量体数:約10.3)を使用した以外は実施例1と同様にして、乳化力(%)を算出した。
製造例1で得られた反応液(1)に代えて、ポリグリセリンモノラウリルエーテル((株)ダイセル製、モノエーテル体含有率:94重量%、平均グリセリン量体数:約4.1)を使用した以外は実施例1と同様にして、乳化力(%)を算出した。
製造例1で得られた反応液(1)に代えて、ポリオキシエチレンイソセチルエーテル(商品名「EMALEX 1605」、日本エマルジョン(株)製)を使用した以外は実施例1と同様にして、乳化力(%)を算出した。
製造例1で得られた反応液(1)に代えて、ポリオキシエチレンイソステアリルエーテル(商品名「EMALEX 1805」、日本エマルジョン(株)製)を使用した以外は実施例1と同様にして、乳化力(%)を算出した。
被乳化油として流動パラフィン(25℃における動粘度:9.8mm2/s)4.0gを使用した以外は実施例1と同様にして、反応液(1)の乳化力(%)を算出した。
被乳化油としてオリーブオイル(25℃における動粘度:80.1mm2/s)4.0gを使用した以外は実施例1と同様にして、反応液(1)の乳化力(%)を算出した。
Claims (7)
- R1が、炭素数6~14の芳香族炭化水素環と、ヘテロ原子として酸素原子を含む3~6員の複素環との縮合環である環Zにおける前記複素環部分に結合する置換基である、請求項1に記載の非イオン界面活性剤。
- 洗浄剤として使用する、請求項1~3の何れか1項に記載の非イオン界面活性剤。
- 乳化剤として使用する、請求項1~3の何れか1項に記載の非イオン界面活性剤。
- 乳化重合用乳化剤として使用する、請求項1~3の何れか1項に記載の非イオン界面活性剤。
- 可溶化剤として使用する、請求項1~3の何れか1項に記載の非イオン界面活性剤。
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US16/308,105 US10844034B2 (en) | 2016-06-10 | 2017-04-21 | Nonionic surfactant |
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US (1) | US10844034B2 (ja) |
EP (1) | EP3470503B1 (ja) |
JP (1) | JP6957465B2 (ja) |
KR (1) | KR102211353B1 (ja) |
WO (1) | WO2017212803A1 (ja) |
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BR112022024657A2 (pt) * | 2020-06-05 | 2022-12-27 | Basf Se | Uso de pelo menos um composto de fórmula geral, método de polimerização de emulsão, mistura, composto, composição de limpeza, e, processo para preparar um composto |
CN116120269A (zh) * | 2023-01-04 | 2023-05-16 | 山东滨州金盛新材料科技有限责任公司 | 一种水溶性聚甘油基生育酚及其制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH07126690A (ja) | 1993-03-03 | 1995-05-16 | Sanyo Chem Ind Ltd | 界面活性剤 |
JPH11124563A (ja) * | 1997-08-08 | 1999-05-11 | Mitsubishi Chemical Corp | 可溶化剤およびこれを用いたヒドロゾル組成物 |
JP2001114720A (ja) * | 1999-10-15 | 2001-04-24 | Taiyo Kagaku Co Ltd | ポリグリセリンアルキルエーテルおよびその組成物 |
JP2004285099A (ja) * | 2003-03-19 | 2004-10-14 | Mitsubishi Chemicals Corp | ポリグリセリン脂肪酸エステルを含有する食器用水系リンス剤 |
JP2016115801A (ja) | 2014-12-15 | 2016-06-23 | 株式会社東芝 | 半導体装置 |
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US6005126A (en) | 1997-08-08 | 1999-12-21 | Mitsubishiki Chemical Corporation | Solubilizing agent and hydrosol composition obtained by using the same |
US6683222B2 (en) | 1999-02-18 | 2004-01-27 | Taiyo Kagaku Co., Ltd. | Polyether-polyol compound |
JP2010507361A (ja) * | 2006-07-31 | 2010-03-11 | キュアバック ゲーエムベーハー | 具体的には免疫刺激剤/アジュバントとしての、一般式(I):GlXmGn、または一般式(II):ClXmCnで表される核酸 |
JP2009227583A (ja) | 2008-03-19 | 2009-10-08 | Daicel Chem Ind Ltd | ポリグリセリンアルキルエーテル型非イオン界面活性剤 |
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- 2017-04-21 JP JP2018522365A patent/JP6957465B2/ja active Active
- 2017-04-21 EP EP17809985.9A patent/EP3470503B1/en active Active
- 2017-04-21 KR KR1020187036163A patent/KR102211353B1/ko active IP Right Grant
- 2017-04-21 US US16/308,105 patent/US10844034B2/en active Active
- 2017-04-21 WO PCT/JP2017/016051 patent/WO2017212803A1/ja unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07126690A (ja) | 1993-03-03 | 1995-05-16 | Sanyo Chem Ind Ltd | 界面活性剤 |
JPH11124563A (ja) * | 1997-08-08 | 1999-05-11 | Mitsubishi Chemical Corp | 可溶化剤およびこれを用いたヒドロゾル組成物 |
JP2001114720A (ja) * | 1999-10-15 | 2001-04-24 | Taiyo Kagaku Co Ltd | ポリグリセリンアルキルエーテルおよびその組成物 |
JP2004285099A (ja) * | 2003-03-19 | 2004-10-14 | Mitsubishi Chemicals Corp | ポリグリセリン脂肪酸エステルを含有する食器用水系リンス剤 |
JP2016115801A (ja) | 2014-12-15 | 2016-06-23 | 株式会社東芝 | 半導体装置 |
Non-Patent Citations (1)
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Also Published As
Publication number | Publication date |
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JP6957465B2 (ja) | 2021-11-02 |
JPWO2017212803A1 (ja) | 2019-04-04 |
KR102211353B1 (ko) | 2021-02-03 |
KR20190018433A (ko) | 2019-02-22 |
US20190300495A1 (en) | 2019-10-03 |
EP3470503A4 (en) | 2020-01-15 |
EP3470503A1 (en) | 2019-04-17 |
EP3470503B1 (en) | 2024-02-14 |
US10844034B2 (en) | 2020-11-24 |
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