WO2018030328A1 - 界面活性剤組成物 - Google Patents
界面活性剤組成物 Download PDFInfo
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- WO2018030328A1 WO2018030328A1 PCT/JP2017/028559 JP2017028559W WO2018030328A1 WO 2018030328 A1 WO2018030328 A1 WO 2018030328A1 JP 2017028559 W JP2017028559 W JP 2017028559W WO 2018030328 A1 WO2018030328 A1 WO 2018030328A1
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- ICZKASVWFUJTEI-UHFFFAOYSA-N n,n-dimethyldocosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN(C)C ICZKASVWFUJTEI-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- HTKPDYSCAPSXIR-UHFFFAOYSA-N octyltrimethylammonium ion Chemical class CCCCCCCC[N+](C)(C)C HTKPDYSCAPSXIR-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- GLFDLEXFOHUASB-UHFFFAOYSA-N trimethyl(tetradecyl)azanium Chemical class CCCCCCCCCCCCCC[N+](C)(C)C GLFDLEXFOHUASB-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C11D1/83—Mixtures of non-ionic with anionic compounds
- C11D1/831—Mixtures of non-ionic with anionic compounds of sulfonates with ethers of polyoxyalkylenes without phosphates
-
- 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
- C11D1/83—Mixtures of non-ionic with anionic 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
- A61K8/30—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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- 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
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- 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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- 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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- 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
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/345—Phosphates or phosphites
-
- 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
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
-
- 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
Definitions
- the present invention relates to a surfactant composition. Specifically, the present invention relates to a surfactant composition containing a surfactant at a high concentration and having fluidity in a wide concentration range.
- liquid cleaning agents are provided for a wide range of cleaning applications, from clothing to residential, hair, and body use.
- Liquid detergents have the advantage of being easy to use and exhibiting a stable and high detergency because they are highly soluble in water and less concerned about remaining undissolved even in winter.
- the liquid cleaning agent can be used in various bottles such as a dispenser and a pump former, it has a wide range of applications as a cleaning agent. Because of these advantages, liquid detergents are growing in the market. In particular, concentrated liquid detergents that contain a high concentration of surfactants to reduce the size of the detergent itself can reduce the amount of each use. Therefore, it is easy to use, and because it becomes a more compact product, it leads to reduction of container resin amount, transportation cost, and energy.
- Patent Document 1 discloses a concentrated liquid cleaning composition that is liquid and uniform at normal storage temperatures, including a polyalkoxy nonionic surfactant and an ionic surfactant having a non-terminal ionic functional group. ing.
- Patent Document 2 includes an internal olefin sulfonate having 8 to 26 carbon atoms, and at least 25% by weight of the internal olefin sulfonate has a ⁇ -hydroxyalkanesulfonate structure. Is disclosed.
- Patent Document 3 discloses an anionic surfactant (i) which is an internal olefin sulfonate, vinylidene sulfonate, or a mixture thereof, and a nonionic surfactant having an HLB value of 10.5 or less (A detergent composition is disclosed wherein ii) is the main component and the weight ratio of (i) to (ii) is 9: 1 to 1: 9.
- Patent Document 4 discloses a cleansing composition for skin or hair that contains an internal olefin sulfonate (A) having 12 to 24 carbon atoms and has good foam persistence and rinsing properties. Yes.
- Patent Document 5 excludes an internal olefin sulfonate (A) having 12 to 24 carbon atoms, an internal olefin sulfonate (A) and an anionic surfactant having two or more carboxylic acid groups.
- a skin or hair cleaning composition containing an anionic surfactant (B) containing no sulfate group is disclosed.
- Patent Document 6 discloses a sulfonate containing an internal olefin sulfonate (A) having 16 carbon atoms and an internal olefin sulfonate (B) having 18 carbon atoms in an aqueous medium. Disclosed are mixtures containing the mixture as well as at least one foam enhancer or foam enhancer.
- Patent Document 7 discloses a detergent composition containing an internal olefin sulfonate having 8 to 26 carbon atoms and containing at least 25% by weight of ⁇ -hydroxysulfonate with respect to the total sulfonate. Has been.
- a detergent composition containing a surfactant in a high concentration has a problem that the solubility is lowered and precipitates or a strong gel is formed, so that the usability is remarkably impaired. Therefore, in many liquid detergents, a large amount of organic solvent is used in combination in order to sufficiently dissolve the surfactant and maintain fluidity. On the other hand, many organic solvents are mostly petrochemical substances, and it is desired to refrain from using organic solvents from the viewpoints of sustainability, environmental burden, safety, and the like. Further, by ensuring the fluidity of the cleaning agent without depending on the organic solvent, foaming at the time of using the liquid cleaning agent and viscosity control suitable for various applications are facilitated.
- the present invention relates to a surfactant composition containing a surfactant at a high concentration and having fluidity in a wide concentration range.
- the present invention contains the following components A, B, C and D,
- the total content of components A, B and C is 30% by mass or more and 80% by mass or less
- the mass ratio (A + B) / C of the total content of components A and B and the content of component C is 20/80 to 80/20
- the present invention relates to a surfactant composition having a mass ratio A / B of the content of component A to the content of component B of 98/2 to 45/55.
- a Internal olefin sulfonic acid and / or salt thereof Anionic surfactant other than component A
- a surfactant composition containing a surfactant at a high concentration and having fluidity in a wide concentration range can be obtained. Therefore, the usage-amount of the organic solvent mix
- the surfactant composition of the present invention is characterized in that fine bubbles can be obtained even at a high concentration or diluted, and the fine foam state can be maintained for a long time after foaming.
- the surfactant composition of the present invention contains the following components A, B, C and D,
- the total content of components A, B and C is 30% by mass or more and 80% by mass or less
- the mass ratio (A + B) / C of the total content of components A and B and the content of component C is 20/80 to 80/20
- the mass ratio A / B of the content of component A and the content of component B is 98/2 to 45/55.
- a Internal olefin sulfonic acid and / or salt thereof Anionic surfactant other than component A
- the surfactant composition of the present invention is excellent in fluidity from a high concentration to a low concentration by containing the components A, B and C in specific amounts and in specific content ratios.
- the reason why such characteristics are manifested is not clear, but is considered as follows.
- the molecular structure of surfactants is largely classified into hydrophilic groups and hydrophobic groups, but in high-concentration surfactant aqueous solutions, the interaction between hydrophobic groups is strong, resulting in the formation of liquid crystals and solid precipitation. Causes thickening.
- the regularity of the orientation of the hydrophobic group is lowered by containing the components A, B and C in a specific amount and a specific content ratio, and the liquid crystal formation and solid precipitation can be suppressed. .
- this effect is an estimate and does not limit the scope of the present invention.
- the carbon number of the internal olefin sulfonic acid and / or the salt thereof is preferably Is 12 or more, more preferably 14 or more, still more preferably 16 or more, and is preferably 24 or less, more preferably 22 or less, still more preferably 20 or less, and still more preferably 18 or less. These may be used alone or in combination of two or more different carbon numbers.
- the internal olefin sulfonate is a sulfonate obtained by sulfonating, neutralizing and hydrolyzing the internal olefin (olefin having a double bond inside the olefin chain) as a raw material.
- the internal olefin has a broad meaning including a case where a so-called ⁇ -olefin containing a trace amount of a double bond is located at the 1st position of the carbon chain.
- the product obtained is mainly a mixture of these, part of which is a hydroxyalkane sulfonate having a hydroxy group at the end of the carbon chain, or an olefin having a double bond at the end of the carbon chain.
- a sulfonate may be contained in a trace amount.
- each of these products and mixtures thereof are collectively referred to as internal olefin sulfonates.
- the hydroxyalkane sulfonate is also referred to as a hydroxy form of internal olefin sulfonate (hereinafter also referred to as HAS), and the olefin sulfonate is also referred to as an olefin form of internal olefin sulfonate (hereinafter also referred to as IOS).
- HAS internal olefin sulfonate
- IOS internal olefin form of internal olefin sulfonate
- the internal olefin sulfonic acid is in the acid state of the internal olefin sulfonate.
- Component A is preferably an internal olefin sulfonate.
- the internal olefin sulfonate is a hydroxyalkane sulfonate, an olefin sulfonate, or a mixture containing these, but is preferably a mixture containing these.
- the mass ratio of the hydroxyalkane sulfonate content to the olefin sulfonate content (hydroxy product / olefin product) is preferably 50/50 to 99 / from the viewpoint of improving productivity and reducing impurities. 1, more preferably 60/40 to 99/1, still more preferably 70/30 to 99/1, still more preferably 75/25 to 99/1, and still more preferably 75 / 25-95 / 5.
- the mass ratio of the content of the hydroxyalkane sulfonate and the content of the olefin sulfonate in Component A or the surfactant composition is determined by HPLC from the component A or the resulting surfactant composition. And the olefin sulfonate can be separated and then measured by the method described in Examples.
- the total content of hydroxyalkane sulfonate and olefin sulfonate in the internal olefin sulfonate is 90% by mass or more, preferably 95% by mass or more, more preferably 98% by mass or more, and 100%. It is below mass%.
- the said internal olefin sulfonic acid and / or its salt contain 5 mass% or more of what the position of a sulfonic acid group is 2nd from a viewpoint of further expressing the effect of this invention. Further, it is preferable that the sulfonic acid group is located at the 2-position at 40% by mass or less, more preferably 35% by mass or less, still more preferably 30% by mass or less, and still more preferably 28% by mass. % Or less.
- the internal olefin sulfonic acid and / or salt thereof preferably contains 80% by mass or more, more preferably 90% by mass or more, and still more preferably 95% by mass of the sulfonic acid group at the 2-position or more. Including, more preferably 98% by mass or more, and 100% by mass or less.
- the internal olefin sulfonic acid or a salt thereof can be produced by a known method, for example, by sulfonating, neutralizing and hydrolyzing the internal olefin.
- a known method for example, by sulfonating, neutralizing and hydrolyzing the internal olefin.
- each step will be specifically described.
- the internal olefin is an olefin having a double bond inside the carbon chain.
- the internal olefin used in the reaction may contain a small amount of so-called ⁇ -olefin in which the double bond is located at the 1st position of the carbon chain.
- the internal olefin preferably contains 40% by mass or less, more preferably 35% by mass or less, and more preferably 35% by mass or less. Is 30% by mass or less, more preferably 28% by mass or less, and preferably 10% by mass or more, more preferably 15% by mass or more from the viewpoint of the productivity of internal olefins.
- the carbon number of the internal olefin is preferably 12 or more, more preferably 14 or more, still more preferably 16 or more, and preferably 24 or less, more preferably 22 Hereinafter, it is more preferably 20 or less, and still more preferably 18 or less.
- the internal olefin can be produced by a known method, for example, a method described in International Publication No. 2011/052732.
- the sulfonation step is not particularly limited, it is a step of obtaining an internal olefin sulfonate by reacting an internal olefin with sulfur trioxide.
- the neutralization step is not particularly limited, but is a step of obtaining a neutralized product by reacting the internal olefin sulfonate with an alkali compound.
- the hydrolysis step is not particularly limited, but is a step of reacting the obtained neutralized product with water to hydrolyze the neutralized product.
- the obtained internal olefin sulfonic acid and / or salt thereof can be used as it is, but further purification such as desalting and decolorization may be performed.
- anionic surfactants other than the component A can be used without particular limitation.
- examples of the anionic surfactant include alkyl sulfates having 10 to 22 carbon atoms, alkenyl sulfates having 10 to 22 carbon atoms, polyoxyalkylene alkyl ether sulfates having 10 to 22 carbon atoms, and those having 10 to 22 carbon atoms.
- C10-22 sulfate ester salt such as polyoxyalkylene alkenyl ether sulfate, C10-22 polyoxyalkylene alkylphenyl ether sulfate; C10-22 sulfosuccinic acid alkyl ester salt, C10-22 22 polyoxyalkylene sulfosuccinic acid alkyl ester salts, alkane sulfonates having 10 to 22 carbon atoms, acyl isethionates having 10 to 22 carbon atoms, acyl methyl taurates having 10 to 22 carbon atoms, and 10 to 22 carbon atoms C10-22 sulfonates such as alkyl sulfoacetic acid; carbon number Fatty acid salt having 0 to 22 carbon atoms, polyoxyalkylene alkyl ether carboxylate having 10 to 22 carbon atoms, polyoxyalkylene alkenyl ether carboxylate having 10 to 22 carbon atoms, polyoxyalkylene alkyl phen
- C10-22 phosphate ester Salts Amino acid salts having an acyl group having 10 to 22 carbon atoms such as acyl glutamate, acylalanine, acyl glycine, acyl sarcosine and acyl arginine. These may be used alone or in combination of two or more.
- alkyl sulfates having 10 to 22 carbon atoms from the viewpoint of improving the foaming of the solution and obtaining fine foams, alkyl sulfates having 10 to 22 carbon atoms, polyoxyalkylene alkyl ether sulfates having 10 to 22 carbon atoms and the like are preferable.
- An amino acid salt having an acyl group having 10 to 22 carbon atoms such as an acyl glutamate salt, an acyl alanine salt, an acyl glycine salt, and an acyl arginine salt, more preferably carbon
- An alkyl sulfate having a number of 10 to 22, a polyoxyalkylene alkyl ether sulfate having a carbon number of 10 to 22, and a fatty acid salt having a carbon number of 8 to 12 are used.
- Nonionic surfactant can be used without particular limitation.
- the nonionic surfactant include polyoxyalkylene alkyl ether having 10 to 22 carbon atoms, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene fatty acid ester, carbon Polyalkylene glycol type nonionic surfactants such as polyoxyethylene alkylphenyl ethers having several tens to twenty-two and polyoxyalkylene (hardened) castor oil having ten to twenty-two carbons; sucrose fatty acid esters, polyglycerin having ten to twenty-two carbons; Polyhydric alcohol type nonionic surfactants such as alkyl ethers, polyglycerin fatty acid esters, alkyl glycosides having 10 to 22 carbon atoms, and acylated alkyl glucamides; fatty acid alkanolamides and the like It is.
- the fatty acid or acyl group of the nonionic surfactant represents a fatty acid having 10 to 22 carbon atoms.
- Specific examples include fatty acid monoalkanolamides such as coconut oil fatty acid monoethanolamide and coconut oil fatty acid N-methylmonoethanolamide. These may be used alone or in combination of two or more.
- polyoxyalkylene alkyl ethers having 10 to 22 carbon atoms and alkyl glycosides having 10 to 22 carbon atoms are preferably used from the viewpoint of effectively reducing the solution viscosity, and more preferably the following general formula.
- the polyoxyalkylene alkyl ether represented by (1) is used.
- R—O— (AO) n —H (1) In the formula, R is a hydrocarbon group having 8 to 22 carbon atoms, AO is an alkyleneoxy group, and n is 5 or more.
- the carbon number of the hydrocarbon group is preferably 10 or more, more preferably 12 or more, and preferably 18 or less, more preferably 16 or less, and still more preferably 14 from the viewpoint of effectively reducing the solution viscosity. It is as follows.
- the hydrocarbon group may be a straight chain or a branched chain.
- alkyleneoxy group examples include an ethyleneoxy group, a propyleneoxy group, and a butyleneoxy group.
- n represents the average number of moles of the alkyleneoxy group, and is preferably 7 or more, more preferably 10 or more, still more preferably 12 or more, and preferably 100 or less from the viewpoint of effectively reducing the solution viscosity. More preferably, it is 40 or less, More preferably, it is 30 or less.
- the AO may be one kind of alkyleneoxy group or may contain two or more kinds of alkyleneoxy groups. From the viewpoint of effectively reducing the solution viscosity, the AO is preferably one or more selected from ethyleneoxy groups and propyleneoxy groups, more preferably includes both ethyleneoxy groups and propyleneoxy groups, and more preferably. Is an ethyleneoxy group and a propyleneoxy group having a block structure.
- polyoxyalkylene alkyl ether examples include, for example, lauryl ether to which 15 to 25 moles of ethyleneoxy groups have been added, lauryl ether to which 15 to 25 moles of ethyleneoxy groups and propyleneoxy groups have been added, and 15 to 15 ethyleneoxy groups.
- Component D contained in the surfactant composition of the present invention is water, and is not particularly limited, but purified water such as ion exchange water, distilled water, and reverse osmosis membrane water is preferable.
- the surfactant composition of the present invention contains at least the components A, B, C and D.
- the total content of components A, B and C is 30% by mass or more and 80% by mass or less from the viewpoint of manifesting the effects of the present invention.
- the total content of components A, B, and C is 40% by mass or more, 45% by mass or more, 50% by mass or more, 55% by mass or more, or 60% by mass or more from the viewpoint of further developing the effects of the present invention. And can be 75 mass% or less, 70 mass% or less, or 65 mass% or less.
- the mass ratio (A + B) / C of the total content of components A and B and the content of component C is 20/80 to 80/20 from the viewpoint of manifesting the effects of the present invention.
- the mass ratio (A + B) / C is preferably 30/70 to 70/30, more preferably 40/60 to 70/30, and still more preferably 45 from the viewpoint of further developing the effects of the present invention. / 55 to 60/40.
- the mass ratio A / B of the content of component A and the content of component B is 98/2 to 45/55 from the viewpoint of manifesting the effects of the present invention.
- the mass ratio A / B is preferably 95/5 to 50/50, more preferably 95/5 to 70/30, and still more preferably 90/10 from the viewpoint of further manifesting the effects of the present invention. Is 70/30, more preferably 90/10 to 80/20.
- the content of component A is not particularly limited as long as it satisfies the above blending conditions.
- the content of component A may be, for example, 5% by mass or more, 10% by mass or more, 15% by mass or more, or 20% by mass or more in the composition.
- content of the component A may be 60 mass% or less, 55 mass% or less, and 50 mass% or less, for example.
- the content of component B is not particularly limited as long as it satisfies the above blending conditions.
- the content of Component B in the composition may be, for example, 0.2% by mass or more, 1% by mass or more, 5% by mass or more, and 30% by mass or less, 25% by mass or less, and 20% by mass or less. It's okay.
- the content of Component C is not particularly limited as long as it satisfies the above blending conditions.
- the content of Component C may be, for example, 5% by mass or more, 10% by mass or more, 15% by mass or more, or 20% by mass or more in the composition.
- content of the component C may be 60 mass% or less, 50 mass% or less, and 40 mass% or less, for example.
- Component D that is, water can be used in an amount that is the balance other than components A, B, C and other components.
- the content of component D is 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, 40% by mass in the composition. 70 mass% or less, 65 mass% or less, 60 mass% or less, 55 mass% or less, 50 mass% or less, 45 mass% or less, 40 mass% or less, or 35 mass% or less. Can do.
- the viscosity at 25 ° C. of the surfactant composition of the present invention is preferably 3000 mPa ⁇ s or less, more preferably 2000 mPa ⁇ s or less, still more preferably 1500 mPa ⁇ s or less, and still more preferably 1000 mPas, from the viewpoint of ease of handling.
- ⁇ S or less more preferably 500 mPa ⁇ s or less, still more preferably 200 mPa ⁇ s or less.
- the lower limit of the viscosity at 25 ° C. is not particularly limited.
- the viscosity is measured by a tuning fork type vibration viscometer (VIBRO VISCOMETER SV-10, manufactured by A & D Co., Ltd.) by the method described in the examples.
- the viscosity at 25 ° C. may be 0 mPa ⁇ s or more.
- the viscosity of 0 mPa ⁇ s includes a case where measurement cannot be performed with a tuning fork type vibration viscometer because the viscosity is too low.
- ⁇ s or more may be, for example, 5 mPa ⁇ s or more, 10 mPa ⁇ s or more, 20 mPa ⁇ s or more, 30 mPa ⁇ s or more, 40 mPa ⁇ s or more, or 50 mPa ⁇ s or more.
- the surfactant composition of the present invention is preferably uniformly dissolved at 25 ° C. from the viewpoint of composition stability.
- the surfactant composition of the present invention is a surfactant other than components A, B, C and D, components other than components A, B, C and D, solvent, fragrance, dye, and storage as long as the effects of the present invention are not impaired.
- Optional ingredients used in detergents such as humectants, moisturizers, antibacterial agents, antidandruff agents, pearlizing agents, vitamins, thickeners, pH adjusters, bleaches, chelating agents, water-soluble salts, and oils Can be contained.
- Surfactants other than components A, B, and C examples include amphoteric surfactants and cationic surfactants.
- amphoteric surfactants include betaine surfactants such as imidazoline betaines, alkyldimethylaminoacetic acid betaines, fatty acid amidopropyl betaines, and sulfobetaines; amine oxide surfactants such as alkyldimethylamine oxides, and the like.
- betaine surfactants such as imidazoline betaines, alkyldimethylaminoacetic acid betaines, fatty acid amidopropyl betaines, and sulfobetaines
- amine oxide surfactants such as alkyldimethylamine oxides, and the like.
- Specific examples include coconut oil fatty acid amidopropyldimethylcarbobetaine, lauramidopropyldimethylcarbobetaine, laurylcarboxymethylhydroxyimidazolium betaine, lauryldimethylaminoacetic acid betaine, and laurylhydroxysulfobetaine. These may be used alone or in combination of two or more
- Examples of the cationic surfactant include a quaternary ammonium salt having a hydrocarbon group having 12 to 28 carbon atoms which may be separated by an amide group, an ester group or an ether group; a pyridinium salt; a mineral of a tertiary amine Examples thereof include salts of acids or organic acids. Specifically, for example, octyltrimethylammonium salt, decyltrimethylammonium salt, lauryltrimethylammonium salt, myristyltrimethylammonium salt, cetyltrimethylammonium salt, stearyltrimethylammonium salt, behenyltrimethylammonium salt, okdadecyloxypropyltrimethylammonium salt, etc.
- Di-long chain alkyldimethylammonium salts such as salts; stearyldimethyl Min, behenyl dimethylamine, octadecenyl siloxy dimethylamine, hydrochloride of dimethylaminopropyl stearic acid amide, mono-long chain alkyl dimethyl amine salts, such as citric acid or lactic acid salts. These may be used alone or in combination of two or more.
- the surfactant composition of the present invention can contain a solvent for the purpose of improving low temperature stability and cleaning performance.
- the solvent include alcohol, glycol ether, alkylene glycol alkyl ether, and the like.
- the alcohol include monohydric alcohols such as ethanol, isopropyl alcohol, and butanol, ethylene glycol, propylene glycol, butylene glycol, hexylene glycol (2-methyl-2,4-pentanediol), 1,5-pentanediol, 1, Examples thereof include polyhydric alcohols such as 6-hexanediol and glycerin, and aromatic alcohols such as benzyl alcohol.
- alkylene glycol ether examples include diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, and tripropylene glycol.
- alkylene glycol alkyl ether examples include diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, tripropylene glycol monomethyl ether, diethylene glycol monobutyl ether, 1-methoxy-2 -Propanol and 1-ethoxy-2-propanol, 2-phenoxyethanol, diethylene glycol monophenyl ether, triethylene glycol monophenyl ether. These may be used alone or in combination of two or more.
- the content of the solvent is not limited, but from the viewpoint of sustainability, environmental load, safety, etc., the content of the solvent in the surfactant composition is preferably 10% by mass or less. More preferably, it is 4 mass% or less, More preferably, it is 1 mass% or less, More preferably, it is 0.1 mass% or less, More preferably, it is 0 mass%, ie, it is preferable not to contain a solvent.
- the surfactant composition of the present invention can be prepared by mixing components A, B, C, D and other components.
- the order in which the components A, B, C and D are mixed is not particularly limited. After mixing the components A, B and C, the components A, B and C may be diluted with water and adjusted to a predetermined concentration. And water may be mixed in advance, component B and water may be mixed in advance, component C and water may be mixed in advance, and then the mixed solution thereof may be mixed. Also, component A and water are premixed, component B and water are premixed, component C and water are premixed, then the mixture is mixed, and further diluted with water to adjust to a predetermined concentration May be.
- the order of preparation is not particularly limited. For example, after preparing a surfactant composition containing components A, B, C and D, the other components are added. You may mix
- the standing temperature is preferably 10 ° C. or higher, more preferably 15 ° C. or higher, further preferably 20 ° C. or higher, and still more preferably 25 ° C. or higher from the viewpoint of obtaining a uniformly dissolved surfactant composition. From the viewpoint of economy, it is preferably 80 ° C. or less, more preferably 70 ° C.
- the standing time varies depending on the temperature, but from the viewpoint of sufficiently uniform dissolution, it is preferably 1 hour or more, more preferably 5 hours or more, still more preferably 12 hours or more, still more preferably 18 hours or more, and even more preferably.
- the surfactant composition of the present invention contains a surfactant at a high concentration, has excellent fluidity from a high concentration to a low concentration, can greatly reduce the amount of organic solvent used, and is suitably used as a liquid detergent. can do.
- the surfactant composition of the present invention can provide fine bubbles even at a high concentration or diluted, and can maintain a fine bubble state for a long time after stirring, thus giving a feeling of washing. In addition to being able to obtain an excellent cleaning effect.
- the surfactant composition of the present invention is used as a cleaning agent such as a liquid detergent for clothes, a detergent for dishes, a detergent for hair, a detergent for body, a detergent for precision parts, and a detergent for hard surfaces. .
- the surfactant composition of the present invention can be used for each of the above cleaning applications by adding it to water and dissolving it.
- ⁇ 1> Contains the following components A, B, C and D,
- the total content of components A, B and C is 30% by mass or more and 80% by mass or less
- the mass ratio (A + B) / C of the total content of components A and B and the content of component C is 20/80 to 80/20
- a surfactant composition having a mass ratio A / B of the content of component A to the content of component B of 98/2 to 45/55.
- the carbon number of the internal olefin sulfonic acid and / or salt thereof is preferably 12 or more, more preferably 14 or more, still more preferably 16 or more, and preferably 24 or less, more preferably 22 or less, still more preferably.
- the surfactant composition according to ⁇ 1> which is 20 or less, more preferably 18 or less.
- HAS hydroxyalkane sulfonate
- IOS olefin sulfonate
- the mass ratio of the hydroxyalkane sulfonate content to the olefin sulfonate content (hydroxy product / olefin product) is preferably 50/50 to 99/1, more preferably 60/40 to 99/1. More preferably, it is 70/30 to 99/1, still more preferably 75/25 to 99/1, and still more preferably 75/25 to 95/5, according to ⁇ 3>.
- Surfactant composition is preferably 50/50 to 99/1, more preferably 60/40 to 99/1. More preferably, it is 70/30 to 99/1, still more preferably 75/25 to 99/1,
- the total content of hydroxyalkane sulfonate and olefin sulfonate in the internal olefin sulfonate is 90% by mass or more, preferably 95% by mass or more, more preferably 98% by mass or more, and 100%.
- the internal olefin sulfonic acid and / or the salt thereof preferably contains 5% by mass or more, preferably 40% by mass or less, more preferably 35% by mass of the sulfonic acid group at the 2-position.
- the internal olefin sulfonic acid and / or salt thereof preferably contains 80% by mass or more, more preferably 90% by mass or more, and still more preferably 95% by mass or more, in which the position of the sulfonic acid group is 2 or more.
- the anionic surfactant includes a sulfate ester salt having 10 to 22 carbon atoms, a sulfonate salt having 10 to 22 carbon atoms, a fatty acid salt having 10 to 22 carbon atoms, a carboxylate salt having 10 to 22 carbon atoms, and 10 to 10 carbon atoms.
- the surface activity according to any one of ⁇ 1> to ⁇ 7>, which is at least one selected from the group consisting of 22 phosphate ester salts and amino acid salts having an acyl group having 10 to 22 carbon atoms. Agent composition.
- the nonionic surfactant is at least one selected from the group consisting of a polyalkylene glycol type nonionic surfactant, a polyhydric alcohol type nonionic surfactant, and a fatty acid alkanolamide, from ⁇ 1> to ⁇ 8>
- R—O— (AO) n —H (1)
- R is a hydrocarbon group having 8 to 22 carbon atoms
- AO is an alkyleneoxy group
- n is 5 or more.
- the number of carbon atoms of the hydrocarbon group is preferably 10 or more, more preferably 12 or more, and preferably 18 or less, more preferably 16 or less, still more preferably 14 or less, the interface according to ⁇ 10>.
- Activator composition. ⁇ 12> N represents the average number of moles of an alkyleneoxy group, preferably 7 or more, more preferably 10 or more, still more preferably 12 or more, and preferably 100 or less, more preferably 40 or less, and still more preferably 30.
- the surfactant composition according to ⁇ 10> or ⁇ 11> which is the following.
- the AO is preferably at least one selected from an ethyleneoxy group and a propyleneoxy group, more preferably includes both an ethyleneoxy group and a propyleneoxy group, and more preferably an ethyleneoxy group and a propyleneoxy group have a block structure.
- the polyoxyalkylene alkyl ether is preferably lauryl ether to which 15 to 25 mol of ethyleneoxy group has been added, lauryl ether to which 15 to 25 mol of ethyleneoxy group and propyleneoxy group have been added in total, and 15 to 25 of ethyleneoxy group.
- the surfactant composition according to any one of ⁇ 10> to ⁇ 13>, wherein the surfactant composition is a lauryl ether prepared.
- the total content of components A, B, and C is 30% by mass or more and 80% by mass or less, and 40% by mass, 45% by mass, 50% by mass, 55% by mass, or 60% by mass or more.
- the surfactant composition according to any one of ⁇ 1> to ⁇ 14> which can be 75% by mass or less, 70% by mass or less, or 65% by mass or less.
- ⁇ 15-2> The surfactant composition according to any one of ⁇ 1> to ⁇ 14>, wherein the total content of components A, B and C is 55% by mass or more.
- the mass ratio (A + B) / C of the total content of components A and B to the content of component C is 20/80 to 80/20, preferably 30/70 to 70/30, more preferably 40
- ⁇ 16-1> The surface activity according to any one of ⁇ 1> to ⁇ 15-2>, wherein the mass ratio (A + B) / C of the total content of components A and B to the content of component C is 40/60 or more Agent composition.
- ⁇ 16-2> The surface activity according to any one of ⁇ 1> to ⁇ 15-2>, wherein the mass ratio (A + B) / C of the total content of components A and B to the content of component C is 45/55 or more Agent composition.
- ⁇ 16-3> The surface activity according to any one of ⁇ 1> to ⁇ 16-2>, wherein the mass ratio (A + B) / C of the total content of components A and B to the content of component C is 60/40 or less. Agent composition.
- ⁇ 16-4> The surface activity according to any one of ⁇ 1> to ⁇ 16-2>, wherein the mass ratio (A + B) / C of the total content of components A and B to the content of component C is 70/30 or less Agent composition.
- the mass ratio A / B between the content of component A and the content of component B is 98/2 to 45/55, preferably 95/5 to 50/50, more preferably 95/5 to 70 /.
- ⁇ 17-1> The surfactant composition according to any one of ⁇ 1> to ⁇ 16-4>, wherein the mass ratio A / B of the content of component A and the content of component B is 70/30 or more.
- ⁇ 17-2> The surfactant composition according to any one of ⁇ 1> to ⁇ 16-4>, wherein the mass ratio A / B of the content of component A and the content of component B is 90/10 to 80/20 object.
- the content of component A in the composition may be 5% by mass or more, 10% by mass or more, 15% by mass or more, and 20% by mass or more, and 60% by mass or less, 55% by mass or less, and 50% by mass.
- the surfactant composition according to any one of ⁇ 1> to ⁇ 17-2> which may be: ⁇ 19>
- the content of Component B in the composition may be 0.2% by mass or more, 1% by mass or more, 5% by mass or more, and 30% by mass or less, 25% by mass or less, or 20% by mass or less.
- the content of Component C may be 5% by weight or more, 10% by weight or more, 15% by weight or more, 20% by weight or more in the composition, and 60% by weight or less, 50% by weight or less, 40% by weight.
- the surfactant composition according to any one of ⁇ 1> to ⁇ 19> which may be: ⁇ 21> Content of component D is 5 mass% or more, 10 mass% or more, 15 mass% or more, 20 mass% or more, 25 mass% or more, 30 mass% or more, 35 mass% or more, 40 mass% or more in a composition. 70 mass% or less, 65 mass% or less, 60 mass% or less, 55 mass% or less, 50 mass% or less, 45 mass% or less, 40 mass% or less, or 35 mass% or less.
- ⁇ 1> to ⁇ 20> The surfactant composition according to any one of ⁇ 1> to ⁇ 20>.
- the surfactant composition has a viscosity at 25 ° C.
- preferably 3000 mPa ⁇ s or less preferably 2000 mPa ⁇ s or less, still more preferably 1500 mPa ⁇ s or less, still more preferably 1000 mPa ⁇ s or less, and even more preferably 500 mPa ⁇ s.
- S or less more preferably 200 mPa ⁇ s or less, and 0 mPa ⁇ s or more, 5 mPa ⁇ s or more, 10 mPa ⁇ s or more, 20 mPa ⁇ s or more, 30 mPa ⁇ s or more, 40 mPa ⁇ s or more, or 50 mPa ⁇ s.
- the surfactant composition according to any one of ⁇ 1> to ⁇ 21> which may be s or more.
- ⁇ 23> The surfactant composition according to any one of ⁇ 1> to ⁇ 22>, wherein the surfactant composition is preferably uniformly dissolved at 25 ° C.
- the content of the solvent in the surfactant composition is preferably 10% by mass or less, more preferably 4% by mass or less, still more preferably 1% by mass or less, still more preferably 0.1% by mass or less, and still more.
- the surfactant composition according to any one of ⁇ 1> to ⁇ 23> which is preferably 0% by mass.
- ⁇ 25> The surfactant composition according to any one of ⁇ 1> to ⁇ 24>, wherein the surfactant composition is a cleaning agent.
- ⁇ 26> A cleaning method using the surfactant composition according to any one of ⁇ 1> to ⁇ 24>.
- ⁇ 27> Use of the surfactant composition according to any one of ⁇ 1> to ⁇ 24> as a cleaning agent.
- GC gas chromatography
- dimethyl disulfide was reacted with an internal olefin to obtain a dithiolated derivative, and then each component was separated by GC.
- the double bond position of the internal olefin was determined from each peak area.
- the apparatus and analysis conditions used for the measurement are as follows.
- GC device “HP6890” manufactured by HEWLETT PACKARD
- column “Ultra-Alloy-1HT capillary column” (30 m ⁇ 250 ⁇ m ⁇ 0.15 ⁇ m, manufactured by Frontier Laboratories), detector (hydrogen flame ion detector (FID))
- Injection temperature 300 ° C. detector temperature 350 ° C.
- ⁇ Method of measuring mass ratio of hydroxy body / olefin body The mass ratio of the hydroxy body / olefin body of the internal olefin sulfonate was measured by HPLC-MS. Specifically, the hydroxy body and the olefin body were separated by HPLC, and each was identified by subjecting to MS. As a result, each ratio was determined from the HPLC-MS peak area.
- the apparatus and conditions used for the measurement are as follows.
- ⁇ Measurement method of content of internal olefin contained in internal olefin sulfonate The content of internal olefin contained in the internal olefin sulfonate was measured by GC. Specifically, ethanol and petroleum ether were added to the aqueous solution of internal olefin sulfonate, followed by extraction to obtain an internal olefin in the petroleum ether phase. The amount of internal olefin was quantified from the GC peak area.
- the apparatus and analysis conditions used for the measurement are as follows.
- GC device “Agilent Technology 6850” (manufactured by Agilent Technologies), column “Ultra-Alloy-1HT capillary column” (15 m ⁇ 250 ⁇ m ⁇ 0.15 ⁇ m, manufactured by Frontier Laboratories), detector (hydrogen ion detector (FID) )), Injection temperature 300 ° C., detector temperature 350 ° C., He flow rate 3.8 mL / min.
- the content of the paraffin component was measured by GC. Specifically, ethanol and petroleum ether were added to the internal olefin sulfonate aqueous solution, followed by extraction to obtain paraffin in the petroleum ether phase. As a result, the amount of paraffin was quantified from the GC peak area.
- the apparatus and analysis conditions used for the measurement are the same as the measurement of the content of the raw material internal olefin.
- GC device (trade name: Agilent Technology 6850, manufactured by Agilent Technologies), column (trade name: HP-1 capillary column 30 m ⁇ 320 ⁇ m ⁇ 0.25 ⁇ m, manufactured by Agilent Technologies), detector (hydrogen ion detector (FID)) ), Injection temperature 300 ° C., detector temperature 300 ° C., He flow rate 1.0 mL / min. , Oven (60 ° C. (0 min.) ⁇ 10 ° C./min. ⁇ 300° C. (10 min.)
- ⁇ Method for Measuring Viscosity of Surfactant Composition The prepared surfactant composition is allowed to stand at room temperature for 1 day or longer, and then the viscosity of the surfactant composition at 25 ° C. is measured with a tuning fork type vibration viscometer (VIBRO VISCOMETER SV-10, manufactured by A & D Co., Ltd.). did. Continuous measurement was performed for 3 minutes from the start of measurement (data update interval: 5 seconds), and the average value was taken as the viscosity of the surfactant composition. The results are shown in Table 1. In addition, when the viscosity was 12000 mPa ⁇ s or more and exceeded the measurement limit of the viscometer, it was described as “no fluidity”.
- the results are shown in Table 1.
- the particle size of the foam is 100 ⁇ m or less.
- the particle size of the foam is 101 to 500 ⁇ m.
- 3 The particle size of the foam is 501 to 1000 ⁇ m.
- 2 The bubble particle size is 1001 ⁇ m or more. 1: No bubbles at all.
- the obtained crude internal olefin was transferred to a distillation flask and distilled at 136 to 160 ° C./4.0 mmHg to obtain a C16 internal olefin having an olefin purity of 100%.
- the double bond distribution of the obtained internal olefin is as follows: C1-position 0.5 mass%, C2-position 16.5 mass%, C3-position 15.4 mass%, C4-position 16.4 mass%, C5-position 17.2 mass%. %, C6 position 14.2% by mass, and C7, position 8 total was 19.8% by mass.
- Production example B 7000 g (28.9 mol) of 1-hexadecanol (product name: Calcoal 6098, manufactured by Kao Corporation) in a flask equipped with a stirrer, 700 g of ⁇ -alumina (STREM Chemicals, Inc.) as a solid acid catalyst (based on the raw alcohol) 10% by mass), and the reaction was carried out for 3 hours while flowing nitrogen (7000 mL / min) through the system at 280 ° C. with stirring. After the reaction, the alcohol conversion was 100%, and the C16 internal olefin purity was 99.6%.
- 1-hexadecanol product name: Calcoal 6098, manufactured by Kao Corporation
- the obtained crude internal olefin was transferred to a distillation flask and distilled at 136 to 160 ° C./4.0 mmHg to obtain a C16 internal olefin having an olefin purity of 100%.
- the double bond distribution of the obtained internal olefin is as follows: C1-position 0.5 mass%, C2-position 30.1 mass%, C3-position 25.5 mass%, C4-position 18.9 mass%, C5-position 11.1 mass%. %, C6 position 7.0 mass%, C7, the total of 8th position was 7.0 mass%.
- the obtained crude internal olefin was transferred to a distillation flask and distilled at 148 to 158 ° C./0.5 mmHg to obtain an 18-carbon internal olefin having an olefin purity of 100%.
- the double bond distribution of the obtained internal olefin is as follows: C1-position 0.5 mass%, C2-position 25.0 mass%, C3-position 22.8 mass%, C4-position 19.1 mass%, C5-position 14.0 mass. %, C6 position 7.4 mass%, C7 position 5.4 mass%, C8, the 9th position total was 5.8 mass%.
- the neutralized product was hydrolyzed by heating in an autoclave at 160 ° C. for 1 hour to obtain a crude product of C16 sodium olefin sulfonate.
- 300 g of the obtained crude product was transferred to a separatory funnel, 300 mL of ethanol was added, and 300 mL of petroleum ether was added at one time to extract and remove oil-soluble impurities.
- the inorganic compound (main component is sodium nitrate) precipitated at the oil / water interface by addition of ethanol was also separated and removed from the aqueous phase by the oil / water separation operation, and this operation was performed three times.
- the aqueous phase was evaporated to dryness to obtain sodium olefin sulfonate (A-1) having 16 carbon atoms.
- the content of the raw material internal olefin in the obtained sodium internal olefin sulfonate is less than 100 ppm (below the GC detection lower limit), the content of the inorganic compound is 0.2% by mass, and the content of the paraffin component is 0.2% by mass. there were.
- the content of sodium olefin sulfonate having a sulfonic acid group at the 2-position was 9.3% by mass.
- HAS body hydroxy body
- IOS body olefin body
- Production Example 2 A sodium olefin sulfonate having 16 carbon atoms (A-2) was obtained under the same conditions as in Production Example 1, except that the 16-carbon internal olefin produced in Production Example B was used.
- the content of the raw material internal olefin in the obtained sodium internal olefin sulfonate was less than 100 ppm (below the GC detection lower limit), the inorganic compound content was 0.2 mass%, and the paraffin component content was below the detection limit. .
- the content of sodium olefin sulfonate having a sulfonic acid group at the 2-position was 19.9% by mass.
- HAS body hydroxy body
- IOS body olefin body
- Production Example 4 Using the internal olefin having 18 carbon atoms produced in Production Example C and carrying out the sulfonation reaction under the same conditions as in Production Example 1, the resulting sulfonated product was stirred at 60 ° C. for 1 hour for isomerization reaction. Went. Subsequently, the obtained sulfonated product was added to an alkaline aqueous solution to which sodium hydroxide was added so as to be 1.2 mole times the theoretical acid value (AV), and neutralized at 30 ° C. for 1 hour with stirring. Then, hydrolysis reaction and extraction operation were carried out under the same conditions as in Production Example 1 to obtain sodium olefin sulfonate (A-4) having 18 carbon atoms.
- A-4 sodium olefin sulfonate
- the content of the raw material internal olefin in the obtained sodium internal olefin sulfonate was less than 100 ppm (below the GC detection lower limit), the inorganic compound content was 0.1% by mass, and the paraffin component content was below the detection limit. .
- the content of sodium olefin sulfonate having a sulfonic acid group at the 2-position was 15.0% by mass.
- content of the hydroxy body (HAS) in internal olefin sulfonate sodium was 55.1 mass%
- content of the olefin body (IOS) was 44.9 mass%.
- Example 1 16-carbon internal olefin sulfonate sodium (A-1), polyoxyalkylene alkyl ether sulfate (manufactured by Kao Corporation, EMAL20C) (B-1) produced in Production Example 1 and poly represented by the following formula Take the oxyalkylene alkyl ether (C-1) in a beaker with the composition shown in Table 1, add an appropriate amount of water, heat to 60 ° C., mix, cool to room temperature, and add the surfactant composition. Prepared.
- C-1 is a block addition reaction of 9 moles of ethylene oxide, 2 moles of propylene oxide, and 9 moles of ethylene oxide per mole of primary linear alcohol having 10 to 14 carbon atoms derived from coconut oil.
- R is a linear alkyl group having 10 to 14 carbon atoms, a is 9, b is 2, and c is 9.
- Examples 2 to 22, Comparative Examples 1 to 9 A surfactant composition was prepared in the same manner as in Example 1 except that the raw materials and blends shown in Tables 1 to 3 were used.
- Tables 1 to 3 A-2 to A-4, B-2 to B-8, C-2, and C-3 are the following compounds. Further, when using B-3, B-6, or B-7, a sodium hydroxide aqueous solution was mixed and used so as to be 1 equivalent to B-3, B-6, or B-7. .
- A-2 Sodium olefin sulfonate having 16 carbon atoms produced in Production Example 2
- A-3 Sodium olefin sulfonate having 18 carbon atoms produced in Production Example 3
- A-4 Carbon number produced in Production Example 4 18 sodium olefin sulfonate
- B-2 sodium dodecyl sulfate (MP Biomedicals, Inc.)
- B-3 Lauric acid (Lunac L-98, manufactured by Kao Corporation)
- B-4 Sodium di (2-ethylhexyl) sulfosuccinate (manufactured by Wako Pure Chemical Industries, Ltd.)
- B-5 Sodium ⁇ -sulfopalmitic acid methyl ester prepared in Production Example 5
- B-6 Polyoxyethylene dodecyl ether carboxylic acid (Akipo LM-26C, manufactured by Kao Chemicals GmbH)
- B-7 N-lauroyl glutamic acid (Ajinomoto Co., Am
- the surfactant compositions of Examples 1 to 22 have low viscosity and fluidity in a wide concentration range.
- the surfactant compositions of Examples 1 to 22 have fine bubbles even at high concentrations, and have maintained a fine bubble state for a long time after foaming.
- the surfactant compositions of Comparative Examples 1 to 9 have a high viscosity at a high concentration and do not have fluidity. Further, it can be seen that the surfactant compositions of Comparative Examples 1 to 9 do not foam at all even when stirred.
- the surfactant composition of the present invention is useful as a cleaning agent for various applications.
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Abstract
Description
一方、有機溶剤の多くは石化系物質が多く、サステナビリティ、環境負荷、及び安全性等の観点から、有機溶剤の使用を控えることが望まれている。また、有機溶剤に依存することなく洗浄剤の流動性を担保することで、液体洗浄剤使用時における泡立ちや、各種用途に適した粘度コントロールが容易になる。
そこで、界面活性剤を高濃度に配合し、有機溶剤の使用量を低減しても均一溶解しゲル化することなく、かつ希釈するなど濃度を変えても流動性を損なわず、広い濃度域で流動性を保つことができる洗浄剤組成物が求められる。
しかしながら、前記特許文献に開示された技術では、界面活性剤を高濃度で含有し、かつ広い濃度域で流動性を保ち低粘度である洗浄剤組成物を提供するには十分でなかった。
成分A、B及びCの合計含有量が30質量%以上80質量%以下であり、
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cが、20/80~80/20であり、
成分Aの含有量と成分Bの含有量の質量比A/Bが、98/2~45/55である界面活性剤組成物、に関する。
A 内部オレフィンスルホン酸及び/又はその塩
B 成分A以外のアニオン界面活性剤
C ノニオン界面活性剤
D 水
成分A、B及びCの合計含有量が30質量%以上80質量%以下であり、
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cが、20/80~80/20であり、
成分Aの含有量と成分Bの含有量の質量比A/Bが、98/2~45/55である。
A 内部オレフィンスルホン酸及び/又はその塩
B 成分A以外のアニオン界面活性剤
C ノニオン界面活性剤
D 水
内部オレフィンスルホン酸又はその塩は、公知のものを特に制限なく使用することができるが、本発明の効果をさらに発現させる観点から、前記内部オレフィンスルホン酸及び/又はその塩の炭素数は、好ましくは12以上、より好ましくは14以上、更に好ましくは16以上であり、また、好ましくは24以下、より好ましくは22以下、更に好ましくは20以下、より更に好ましくは18以下である。これらは1種で用いてもよく、炭素数が異なるものを2種以上併用してもよい。
また、内部オレフィンスルホン酸及び/又はその塩は、スルホン酸基の位置が2位以上であるものを80質量%以上含むことが好ましく、より好ましくは90質量%以上含み、更に好ましくは95質量%以上含み、より更に好ましくは98質量%以上含み、100質量%以下である。
前記成分A以外のアニオン界面活性剤は、公知のものを特に制限なく使用することができる。当該アニオン界面活性剤としては、例えば、炭素数10~22のアルキル硫酸塩、炭素数10~22のアルケニル硫酸塩、炭素数10~22のポリオキシアルキレンアルキルエーテル硫酸塩、炭素数10~22のポリオキシアルキレンアルケニルエーテル硫酸塩、炭素数10~22のポリオキシアルキレンアルキルフェニルエーテル硫酸塩等の炭素数10~22の硫酸エステル塩;炭素数10~22のスルホコハク酸アルキルエステル塩、炭素数10~22のポリオキシアルキレンスルホコハク酸アルキルエステル塩、炭素数10~22のアルカンスルホン酸塩、炭素数10~22のアシルイセチオネート、炭素数10~22のアシルメチルタウレート、炭素数10~22のアルキルスルホ酢酸等の炭素数10~22のスルホン酸塩;炭素数10~22の脂肪酸塩、炭素数10~22のポリオキシアルキレンアルキルエーテルカルボン酸塩、炭素数10~22のポリオキシアルキレンアルケニルエーテルカルボン酸塩、炭素数10~22のポリオキシアルキレンアルキルフェニルエーテルカルボン酸塩等の炭素数10~22のカルボン酸塩;炭素数10~22のアルキルリン酸塩、炭素数10~22のポリオキシアルキレンアルキルエーテルリン酸塩等の炭素数10~22のリン酸エステル塩;アシルグルタミン酸塩、アシルアラニン塩、アシルグリシン塩、アシルサルコシン塩、アシルアルギニン塩等の炭素数10~22のアシル基を有するアミノ酸塩等が挙げられる。これらは1種単独で用いてもよく、2種以上を併用してもよい。
ノニオン界面活性剤は、公知のものを特に制限なく使用することができる。当該ノニオン界面活性剤としては、例えば、炭素数10~22のポリオキシアルキレンアルキルエーテル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンソルビット脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、炭素数10~22のポリオキシエチレンアルキルフェニルエーテル、炭素数10~22のポリオキシアルキレン(硬化)ヒマシ油等のポリアルキレングリコール型ノニオン界面活性剤;ショ糖脂肪酸エステル、炭素数10~22のポリグリセリンアルキルエーテル、ポリグリセリン脂肪酸エステル、炭素数10~22のアルキルグリコシド、アシル化アルキルグルカミド等の多価アルコール型ノニオン界面活性剤;脂肪酸アルカノールアミド等が挙げられる。なお、上記ノニオン界面活性剤の脂肪酸又はアシル基は炭素数10~22の脂肪酸を示す。具体的には、例えば、ヤシ油脂肪酸モノエタノールアミド、ヤシ油脂肪酸N-メチルモノエタノールアミド等の脂肪酸モノアルカノールアミドが挙げられる。これらは1種単独で用いてもよく、2種以上を併用してもよい。
R-O-(AO)n-H (1)
(式中、Rは炭素数8以上22以下の炭化水素基であり、AOはアルキレンオキシ基であり、nは5以上である。)
本発明の界面活性剤組成物に含有される成分Dは水であり、特に制限されるものではないが、イオン交換水、蒸留水、及び逆浸透膜水などの精製水が好ましい。
本発明の界面活性剤組成物は、少なくとも前記成分A、B、C及びDを含有する。
25℃における粘度は、0mPa・s以上であってよい。ここで、粘度が0mPa・sとは、粘度が低すぎるために音叉型振動式粘度計では計測不能な場合を含む。
25℃における粘度は、例えば、5mPa・s以上、10mPa・s以上、20mPa・s以上、30mPa・s以上、40mPa・s以上、又は50mPa・s以上であってよい。
本発明の界面活性剤組成物は、本発明の効果を阻害しない範囲で、成分A、B、C及びD以外に、成分A、B及びC以外の界面活性剤、溶剤、香料、染料、保存料、保湿剤、抗菌剤、抗フケ剤、パール化剤、ビタミン剤、増粘剤、pH調整剤、漂白剤、キレート剤、水溶性塩類、及び油剤等の洗浄剤に用いられる成分を任意に含有することができる。
成分A、B及びCの界面活性剤としては、両性界面活性剤、カチオン界面活性剤が挙げられる。
本発明の界面活性剤組成物は、低温安定性や洗浄性能を高める等の目的で、溶剤を含有することができる。溶剤としては、例えば、アルコールやグリコールエーテル、アルキレングリコールアルキルエーテル等が挙げられる。アルコールとしては、エタノール、イソプロピルアルコール、ブタノール等の1価アルコール、エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキシレングリコール(2-メチル-2,4-ペンタンジオール)、1,5-ペンタンジオール、1,6-ヘキサンジオール及びグリセリン等の多価アルコール、ベンジルアルコール等の芳香族アルコールが挙げられる。アルキレングリコールエーテルとしては、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、トリプロピレングリコールが挙げられる。アルキレングリコールアルキルエーテルとしては、ジエチレングリコールモノメチルエーテル、トリエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、トリプロピレングリコールモノメチルエーテル、ジエチレングリコールモノブチルエーテル、1-メトキシ-2-プロパノール及び1-エトキシ-2-プロパノール、2-フェノキシエタノール、ジエチレングリコールモノフェニルエーテル、トリエチレングリコールモノフェニルエーテルが挙げられる。これらは1種単独で用いてもよく、2種以上を併用してもよい。
成分A、B、C及びDを混合する順序は特に制限されるものではなく、成分A、B及びCを混合した後、水で希釈して所定の濃度に調整してもよいし、成分Aと水を予め混合し、成分Bと水を予め混合し、成分Cと水を予め混合した後、それらの混合液を混合してもよい。また、成分Aと水を予め混合し、成分Bと水を予め混合し、成分Cと水を予め混合した後、それらの混合液を混合し、更に、水で希釈して所定の濃度に調整してもよい。
その他の成分を含有する界面活性剤組成物を調製する場合、調製順序に特に制限はないが、例えば成分A、B、C及びDを含有する界面活性剤組成物を調製した後にその他の成分を配合してもよい。
均一に溶解した界面活性剤組成物を得る観点から、混合した後、所定の温度にて所定の時間静置することが好ましい。静置する温度としては、均一に溶解した界面活性剤組成物を得る観点から、好ましくは10℃以上、より好ましくは15℃以上、更に好ましくは20℃以上、より更に好ましくは25℃以上であり、経済性の観点から好ましくは80℃以下、より好ましくは70℃以下、更に好ましくは60℃以下、より更に好ましくは50℃以下、より更に好ましくは40℃以下、より更に好ましくは30℃以下である。静置する時間は、温度により変わるが、十分に均一溶解する観点から、好ましくは1時間以上、より好ましくは5時間以上、更に好ましくは12時間以上、より更に好ましくは18時間以上、より更に好ましくは24時間以上、より更に好ましくは2日以上、より更に好ましくは3日以上であり、経済性の観点から好ましくは1月以下、より好ましくは20日以下、更に好ましくは10日以下である。
<1>
下記の成分A、B、C及びDを含有し、
成分A、B及びCの合計含有量が30質量%以上80質量%以下であり、
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cが、20/80~80/20であり、
成分Aの含有量と成分Bの含有量の質量比A/Bが、98/2~45/55である界面活性剤組成物。
A 内部オレフィンスルホン酸及び/又はその塩
B 成分A以外のアニオン界面活性剤
C ノニオン界面活性剤
D 水
<2>
前記内部オレフィンスルホン酸及び/又はその塩の炭素数は、好ましくは12以上、より好ましくは14以上、更に好ましくは16以上であり、また、好ましくは24以下、より好ましくは22以下、更に好ましくは20以下、より更に好ましくは18以下である、<1>に記載の界面活性剤組成物。
<3>
前記内部オレフィンスルホン酸塩は、ヒドロキシアルカンスルホン酸塩(HAS)とオレフィンスルホン酸塩(IOS)を含む、<1>又は<2>に記載の界面活性剤組成物。
<4>
ヒドロキシアルカンスルホン酸塩の含有量とオレフィンスルホン酸塩の含有量の質量比(ヒドロキシ体/オレフィン体)は、好ましくは50/50~99/1であり、より好ましくは60/40~99/1であり、更に好ましくは70/30~99/1であり、より更に好ましくは75/25~99/1であり、より更に好ましくは75/25~95/5である、<3>に記載の界面活性剤組成物。
<5>
内部オレフィンスルホン酸塩中のヒドロキシアルカンスルホン酸塩とオレフィンスルホン酸塩の合計含有量は、90質量%以上であり、好ましくは95質量%以上であり、更に好ましくは98質量%以上であり、100質量%以下である、<3>又は<4>に記載の界面活性剤組成物。
<6>
前記内部オレフィンスルホン酸及び/又はその塩は、スルホン酸基の位置が2位であるものを5質量%以上含むことが好ましく、また、40質量%以下で含むことが好ましく、より好ましくは35質量%以下であり、更に好ましくは30質量%以下であり、より更に好ましくは28質量%以下である、<1>~<5>のいずれか1項に記載の界面活性剤組成物。
<7>
前記内部オレフィンスルホン酸及び/又はその塩は、スルホン酸基の位置が2位以上であるものを80質量%以上含むことが好ましく、より好ましくは90質量%以上含み、更に好ましくは95質量%以上含み、より更に好ましくは98質量%以上含み、100質量%以下である、<1>~<6>のいずれか1項に記載の界面活性剤組成物。
<8>
前記アニオン界面活性剤は、炭素数10~22の硫酸エステル塩、炭素数10~22のスルホン酸塩、炭素数10~22の脂肪酸塩、炭素数10~22のカルボン酸塩、炭素数10~22のリン酸エステル塩、及び炭素数10~22のアシル基を有するアミノ酸塩からなる群より選択される少なくとも1種である、<1>~<7>のいずれか1項に記載の界面活性剤組成物。
<9>
前記ノニオン界面活性剤は、ポリアルキレングリコール型ノニオン界面活性剤、多価アルコール型ノニオン界面活性剤、及び脂肪酸アルカノールアミドからなる群より選択される少なくとも1種である、<1>~<8>のいずれか1項に記載の界面活性剤組成物。
<10>
前記ポリアルキレングリコール型ノニオン界面活性剤は、下記一般式(1)で表されるポリオキシアルキレンアルキルエーテルである、<9>に記載の界面活性剤組成物。
R-O-(AO)n-H (1)
(式中、Rは炭素数8以上22以下の炭化水素基であり、AOはアルキレンオキシ基であり、nは5以上である。)
<11>
前記炭化水素基の炭素数は、好ましくは10以上、より好ましくは12以上であり、また、好ましくは18以下、より好ましくは16以下、更に好ましくは14以下である、<10>に記載の界面活性剤組成物。
<12>
前記nは、アルキレンオキシ基の平均モル数を表し、好ましくは7以上、より好ましくは10以上、更に好ましくは12以上であり、また、好ましくは100以下、より好ましくは40以下、更に好ましくは30以下である、<10>又は<11>に記載の界面活性剤組成物。
<13>
前記AOは、好ましくはエチレンオキシ基及びプロピレンオキシ基から選ばれる1種以上であり、より好ましくはエチレンオキシ基とプロピレンオキシ基の両方を含み、更に好ましくはエチレンオキシ基とプロピレンオキシ基がブロック構造を有するものである、<10>~<12>のいずれか1項に記載の界面活性剤組成物。
<14>
前記ポリオキシアルキレンアルキルエーテルは、好ましくはエチレンオキシ基が15~25モル付加されたラウリルエーテル、エチレンオキシ基とプロピレンオキシ基が合計で15~25モル付加されたラウリルエーテル、エチレンオキシ基が15~25モル付加されたミリスチルエーテル、及びエチレンオキシ基とプロピレンオキシ基が合計で15~25モル付加されたミリスチルエーテルであり、更に好ましくは、エチレンオキシ基とプロピレンオキシ基が合計で15~25モル付加されたラウリルエーテルである、<10>~<13>のいずれか1項に記載の界面活性剤組成物。
<15>
成分A、B及びCの合計含有量は、30質量%以上80質量%以下であり、40質量%以上、45質量%以上、50質量%以上、55質量%以上又は60質量%以上とすることができ、75質量%以下、70質量%以下又は65質量%以下とすることができる、<1>~<14>のいずれか1項に記載の界面活性剤組成物。
<15-1>
成分A、B及びCの合計含有量は、40質量%以上である、<1>~<14>のいずれか1項に記載の界面活性剤組成物。
<15-2>
成分A、B及びCの合計含有量は、55質量%以上である、<1>~<14>のいずれか1項に記載の界面活性剤組成物。
<16>
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cは、20/80~80/20であり、好ましくは30/70~70/30であり、より好ましくは40/60~70/30であり、更に好ましくは45/55~60/40である、<1>~<15-2>のいずれか1項に記載の界面活性剤組成物。
<16-1>
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cは、40/60以上である、<1>~<15-2>のいずれか1項に記載の界面活性剤組成物。
<16-2>
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cは、45/55以上である、<1>~<15-2>のいずれか1項に記載の界面活性剤組成物。
<16-3>
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cは、60/40以下である、<1>~<16-2>のいずれか1項に記載の界面活性剤組成物。
<16-4>
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cは、70/30以下である、<1>~<16-2>のいずれか1項に記載の界面活性剤組成物。
<17>
成分Aの含有量と成分Bの含有量の質量比A/Bは、98/2~45/55であり、好ましくは95/5~50/50であり、より好ましくは95/5~70/30であり、更に好ましくは90/10~70/30であり、より更に好ましくは90/10~80/20である、<1>~<16-4>のいずれか1項に記載の界面活性剤組成物。
<17-1>
成分Aの含有量と成分Bの含有量の質量比A/Bは、70/30以上である、<1>~<16-4>のいずれか1項に記載の界面活性剤組成物。
<17-2>
成分Aの含有量と成分Bの含有量の質量比A/Bは、90/10~80/20である、<1>~<16-4>のいずれか1項に記載の界面活性剤組成物。
<18>
成分Aの含有量は、組成物中、5質量%以上、10質量%以上、15質量%以上、20質量%以上であってよく、また、60質量%以下、55質量%以下、50質量%以下であってよい、<1>~<17-2>のいずれか1項に記載の界面活性剤組成物。
<19>
成分Bの含有量は、組成物中、0.2質量%以上、1質量%以上、5質量%以上であってよく、30質量%以下、25質量%以下、20質量%以下であってよい、<1>~<18>のいずれか1項に記載の界面活性剤組成物。
<20>
成分Cの含有量は、組成物中、5質量%以上、10質量%以上、15質量%以上、20質量%以上であってよく、また、60質量%以下、50質量%以下、40質量%以下であってよい、<1>~<19>のいずれか1項に記載の界面活性剤組成物。
<21>
成分Dの含有量は、組成物中、5質量%以上、10質量%以上、15質量%以上、20質量%以上、25質量%以上、30質量%以上、35質量%以上、40質量%以上とすることができ、70質量%以下、65質量%以下、60質量%以下、55質量%以下、50質量%以下、45質量%以下、40質量%以下、35質量%以下とすることができる、<1>~<20>のいずれか1項に記載の界面活性剤組成物。
<22>
前記界面活性剤組成物の25℃における粘度は、好ましくは3000mPa・s以下、より好ましくは2000mPa・s以下、更に好ましくは1500mPa・s以下、より更に好ましくは1000mPa・s以下、より更に好ましくは500mPa・s以下、より更に好ましくは200mPa・s以下であり、また、0mPa・s以上、5mPa・s以上、10mPa・s以上、20mPa・s以上、30mPa・s以上、40mPa・s以上、又は50mPa・s以上であってよい、<1>~<21>のいずれか1項に記載の界面活性剤組成物。
<23>
前記界面活性剤組成物は、好ましくは25℃において均一溶解している、<1>~<22>のいずれか1項に記載の界面活性剤組成物。
<24>
前記界面活性剤組成物中の溶剤の含有量は、好ましくは10質量%以下、より好ましくは4質量%以下、更に好ましくは1質量%以下、より更に好ましくは0.1質量%以下、より更に好ましくは0質量%である、<1>~<23>のいずれか1項に記載の界面活性剤組成物。
<25>
前記界面活性剤組成物は、洗浄剤である<1>~<24>のいずれか1項に記載の界面活性剤組成物。
<26>
<1>~<24>のいずれか1項に記載の界面活性剤組成物を用いる洗浄方法。
<27>
<1>~<24>のいずれか1項に記載の界面活性剤組成物の洗浄剤としての使用。
内部オレフィンの二重結合位置は、ガスクロマトグラフィー(以下、GCと省略)により測定した。具体的には、内部オレフィンに対しジメチルジスルフィドを反応させることでジチオ化誘導体とした後、各成分をGCで分離した。それぞれのピーク面積より内部オレフィンの二重結合位置を求めた。なお、測定に使用した装置および分析条件は次の通りである。GC装置「HP6890」(HEWLETT PACKARD社製)、カラム「Ultra-Alloy-1HTキャピラリーカラム」(30m×250μm×0.15μm、フロンティア・ラボ株式会社製)、検出器(水素炎イオン検出器(FID))、インジェクション温度300℃、ディテクター温度350℃、He流量4.6mL/min.
内部オレフィンスルホン酸塩のヒドロキシ体/オレフィン体の質量比は、HPLC-MSにより測定した。具体的には、HPLCによりヒドロキシ体とオレフィン体を分離し、それぞれをMSにかけることで同定した。結果、そのHPLC-MSピーク面積から各々の割合を求めた。
尚、測定に使用した装置および条件は次の通りである。HPLC装置(商品名:アジレントテクノロジー1100、アジレントテクノロジー社製)、カラム(商品名:L-columnODS4.6×150mm、一般財団法人化学物質評価研究機構製)、サンプル調製(メタノールで1000倍希釈)、溶離液A(10mM酢酸アンモニウム添加水)、溶離液B(10mM酢酸アンモニウム添加メタノール)、グラジェント(0分(A/B=30/70%)→10分(30/70%)→55分(0/100%)→65分(0/100%)→66分(30/70%)→75分(30/70%))、MS装置(商品名:アジレントテクノロジー1100MS SL(G1946D)),MS検出(陰イオン検出 m/z60-1600、UV240nm)
内部オレフィンスルホン酸塩に含まれる内部オレフィンの含有量は、GCにより測定した。具体的には、内部オレフィンスルホン酸塩水溶液にエタノールと石油エーテルを添加した後、抽出し、石油エーテル相に内部オレフィンを得た。そのGCピーク面積から内部オレフィン量を定量した。なお、測定に使用した装置および分析条件は次の通りである。GC装置「アジレントテクノロジー6850」(アジレントテクノロジー社製)、カラム「Ultra-Alloy-1HTキャピラリーカラム」(15m×250μm×0.15μm、フロンティア・ラボ株式会社製)、検出器(水素炎イオン検出器(FID))、インジェクション温度300℃、ディテクター温度350℃、He流量3.8mL/min.
無機塩の含有量は、電位差滴定や中和滴定により測定した、具体的にはNa2SO4の含有量は、硫酸イオン(SO4 2-)を電位差滴定によって求めることで定量した。また、NaOHの含有量は、希塩酸で中和滴定することで定量した。
パラフィン成分の含有量は、GCにより測定した。具体的には、内部オレフィンスルホン酸塩水溶液にエタノールと石油エーテルを添加した後、抽出し、石油エーテル相にパラフィンを得た。結果、そのGCピーク面積からパラフィン量を定量した。尚、測定に使用した装置および分析条件は原料内部オレフィンの含有量の測定と同様である。
スルホン酸基の結合位置は、GCにより測定した。具体的には、得られた内部オレフィンスルホン酸塩に対しトリメチルシリルジアゾメタンを反応させることでメチルエステル化誘導体とした後、各成分をGCで分離した。それぞれのピーク面積比を質量比として、スルホン酸基が2位に存在する内部オレフィンスルホン酸塩の含有量を算出した。なお、測定に使用した装置および分析条件は次の通りである。GC装置(商品名:アジレントテクノロジー6850,アジレントテクノロジー社製)、カラム(商品名:HP-1キャピラリーカラム30m×320μm×0.25μm,アジレントテクノロジー社製)、検出器(水素炎イオン検出器(FID))、インジェクション温度300℃、ディテクター温度300℃、He流量1.0mL/min.、オーブン(60℃(0min.)→10℃/min.→300℃(10min.)
調製した界面活性剤組成物を1日以上室温で静置し、その後、界面活性剤組成物の25℃における粘度を音叉型振動式粘度計(VIBRO VISCOMETER SV-10、株式会社A&D製)により測定した。測定開始から3分間連続測定を行い(データ更新間隔:5秒)、その平均値を界面活性剤組成物の粘度とした。結果を表1に示す。なお、粘度が12000mPa・s以上であり、粘度計の測定限度を超えた場合、「流動性なし」と記載した。
10mL用のねじ口試験管(株式会社マルエム製)に、調製した界面活性剤組成物2gを加えて、ペンシルミキサー(アズワン株式会社製、No.11-229-02)を用いて15秒間撹拌した。そして、撹拌直後、5分後、及び1時間後の泡の粒径をデジタルマイクロスコープ(株式会社キーエンス製、VHX-1000)を用いて測定した。具体的には、溶液の泡部分を静かにスポイトでスライドグラス上に採取し、このものをデジタルマイクロスコープにて観察した。観察像の中から目視で平均的大きさのものを3つ選びそれぞれ測定し、それらの平均値を算出した。結果を表1に示す。なお、泡粒子がないため、泡粒子の粒径を測定できなかった場合は×とした。また、得られた平均値をもとにして、泡の粒径を下記基準で評価した。
5:泡の粒径が100μm以下である。
4:泡の粒径が101~500μmである。
3:泡の粒径が501~1000μmである。
2:泡の粒径が1001μm以上である。
1:全く泡立たない。
製造例A
撹拌装置付きフラスコに1-ヘキサデカノール(製品名:カルコール6098、花王株式会社製)7000g(28.9モル)、固体酸触媒としてγ―アルミナ(STREM Chemicals,Inc社)700g(原料アルコールに対して10質量%)を仕込み、撹拌下、280℃にて系内に窒素(7000mL/分)を流通させながら5時間、反応を行った。反応終了後のアルコール転化率は100%、C16内部オレフィン純度は99.7%であった。得られた粗内部オレフィンを蒸留用フラスコに移し、136~160℃/4.0mmHgで蒸留することでオレフィン純度100%の炭素数16の内部オレフィンを得た。得られた内部オレフィンの二重結合分布は、C1位0.5質量%、C2位16.5質量%、C3位15.4質量%、C4位16.4質量%、C5位17.2質量%、C6位14.2質量%、C7、8位の合計が19.8質量%であった。
撹拌装置付きフラスコに1-ヘキサデカノール(製品名:カルコール6098、花王株式会社製)7000g(28.9モル)、固体酸触媒としてγ―アルミナ(STREM Chemicals,Inc社)700g(原料アルコールに対して10質量%)を仕込み、撹拌下、280℃にて系内に窒素(7000mL/分)を流通させながら3時間、反応を行った。反応終了後のアルコール転化率は100%、C16内部オレフィン純度は99.6%であった。得られた粗内部オレフィンを蒸留用フラスコに移し、136~160℃/4.0mmHgで蒸留することでオレフィン純度100%の炭素数16の内部オレフィンを得た。得られた内部オレフィンの二重結合分布は、C1位0.5質量%、C2位30.1質量%、C3位25.5質量%、C4位18.9質量%、C5位11.1質量%、C6位7.0質量%、C7、8位の合計が7.0質量%であった。
撹拌装置付きフラスコに1―オクタデ力ノール(製品名:力ルコール8098、花王株式会社製)7000g(25.9モル)、固体酸触媒としてγ-アルミナ(STREM Chemicals, Inc社)1050g(原料アルコールに対して15質量%)を仕込み、撹拌下、285℃にて系内に窒素(7000mL/分)を流通させながら10時間、反応を行った。反応終了後のアルコール転化率は100%、C18内部オレフィン純度は98.2%であった。得られた粗内部オレフィンを蒸留用フラスコに移し、148~158℃/0.5mmHgで蒸留することでオレフィン純度100%の炭素数18の内部オレフィンを得た。得られた内部オレフィンの二重結合分布は、C1位0.5質量%、C2位25.0質量%、C3位22.8質量%、C4位19.1質量%、C5位14.0質量%、C6位7.4量%、C7位5.4質量%、C8、9位の合計が5.8質量%であった。
製造例1
製造例Aで製造した炭素数16の内部オレフィンを、薄膜式スルホン化反応器(内径14mmφ、長さ4m)を使用してSO3濃度2.8容量%の三酸化硫黄ガス、反応器外部ジャケットに20℃の冷却水を通液することでスルホン化反応を行った。尚、SO3/内部オレフィン反応モル比は1.09に設定した。
得られたスルホン化物を、理論酸価(AV)に対し1.2モル倍になるよう水酸化ナトリウムを添加したアルカリ水溶液へ添加し、撹拌しながら30℃, 1時間中和した。中和物をオートクレーブ中で160℃、1時間加熱することで加水分解を行い、C16内部オレフィンスルホン酸ナトリウム粗生成物を得た。
得られた粗生成物300gを分液漏斗に移し、エタノール300mLを加えた後、1回あたり石油エーテル300mLを加えて油溶性の不純物を抽出除去した。この際、エタノールの添加により油水界面に析出した無機化合物(主成分は芒硝)も、油水分離操作により水相から分離除去し、この操作を3回おこなった。水相側を蒸発乾固して、炭素数16の内部オレフィンスルホン酸ナトリウム(A-1)を得た。得られた内部オレフィンスルホン酸ナトリウム中の原料内部オレフィンの含有量は100ppm未満(GC検出下限未満)、無機化合物の含有量は0.2質量%、パラフィン成分の含有量は0.2質量%であった。また、スルホン酸基が2位に存在する内部オレフィンスルホン酸ナトリウムの含有量は、9.3質量%であった。また、内部オレフィンスルホン酸ナトリウム中のヒドロキシ体(HAS体)の含有量は84.2質量%、オレフィン体(IOS体)の含有量は14.4質量%であった。残分の1.0質量%は水であった。
製造例Bで製造した炭素数16の内部オレフィンを用いた以外は、製造例1と同様の条件で、炭素数16の内部オレフィンスルホン酸ナトリウム(A-2)を得た。得られた内部オレフィンスルホン酸ナトリウム中の原料内部オレフィンの含有量は100ppm未満(GC検出下限未満)、無機化合物の含有量は0.2質量%、パラフィン成分の含有量は検出限界以下であった。また、スルホン酸基が2位に存在する内部オレフィンスルホン酸ナトリウムの含有量は、19.9質量%であった。また、内部オレフィンスルホン酸ナトリウム中のヒドロキシ体(HAS体)の含有量は83.6質量%、オレフィン体(IOS体)の含有量は15.1質量%であった。残分の1.1質量%は水であった。
製造例Cで製造した炭素数18の内部オレフィンを用いた以外は、製造例1と同様の条件で、炭素数18の内部オレフィンスルホン酸ナトリウム(A-3)を得た。得られた内部オレフィンスルホン酸ナトリウム中の原料内部オレフィンの含有量は100ppm未満(GC検出下限未満)、無機化合物の含有量は0.4質量%、パラフィン成分の含有量は検出限界以下であった。また、スルホン酸基が2位に存在する内部オレフィンスルホン酸ナトリウムの含有量は、15.0質量%であった。また、内部オレフィンスルホン酸ナトリウム中のヒドロキシ体(HAS)の含有量は84.4質量%、オレフィン体(IOS)の含有量は15.6質量%であった。
製造例Cで製造した炭素数18の内部オレフィンを用い、製造例1と同様の条件でスルホン化反応を行った後、得られたスルホン化物を60℃にて1時間撹拌することで異性化反応を行った。続いて、得られたスルホン化物を、理論酸価(AV)に対し1.2モル倍になるよう水酸化ナトリウムを添加したアルカリ水溶液へ添加し、撹拌しながら30℃、1時間中和した後、製造例1と同様の条件で加水分解反応、抽出操作を行い、炭素数18の内部オレフィンスルホン酸ナトリウム(A-4)を得た。得られた内部オレフィンスルホン酸ナトリウム中の原料内部オレフィンの含有量は100ppm未満(GC検出下限未満)、無機化合物の含有量は0.1質量%、パラフィン成分の含有量は検出限界以下であった。また、スルホン酸基が2位に存在する内部オレフィンスルホン酸ナトリウムの含有量は、15.0質量%であった。また、内部オレフィンスルホン酸ナトリウム中のヒドロキシ体(HAS)の含有量は55.1質量%、オレフィン体(IOS)の含有量は44.9質量%であった。
薄膜式反応器を用いて、パルミチン酸メチルに三酸化硫黄ガスを接触させ、反応モル比(三酸化硫黄ガス/パルミチン酸メチル)=1.2の条件でスルホン化反応を行った。得られたスルホン化物を4つ口フラスコに仕込み、80℃で60分間加熱熟成を行い、スルホン化物に対して5質量%のメタノールを滴下し、更に80℃で60分間加熱熟成を行って、α-スルホパルミチン酸メチルエステルを得た。このα―スルホパルミチン酸メチルエステルを水酸化ナトリウム水溶液中に投入し、pH6.8になるように中和を行い、α-スルホパルミチン酸メチルエステルナトリウム(B-5)を得た。
実施例1
製造例1で作製した炭素数16の内部オレフィンスルホン酸ナトリウム(A-1)、ポリオキシアルキレンアルキルエーテル硫酸塩(花王株式会社製、EMAL20C)(B-1)、及び下記式で表されるポリオキシアルキレンアルキルエーテル(C-1)を表1に記載の配合でビーカーに取り、そこに適量の水を加えて60℃に加温して混合し、室温まで冷却し、界面活性剤組成物を調製した。
R-O-(EO)a-(PO)b-(EO)c-H (C-1)
(C-1は、ヤシ油由来の炭素数10~14の1級直鎖アルコール1モル当りに、エチレンオキサイドを9モル、プロピレンオキサイドを2モル、及びエチレンオキサイドを9モルの順にブロック付加反応させたものである。式中、Rは炭素数10~14の直鎖アルキル基であり、aは9であり、bは2であり、cは9である。)
表1~3に記載の原料及び配合を採用した以外は実施例1と同様の方法で界面活性剤組成物を調製した。なお、表1~3中のA-2~A-4、B-2~B-8、C-2、及びC-3は以下の化合物である。また、B-3、B-6、又はB-7を用いる際は、B-3、B-6、又はB-7に対して1当量となるように水酸化ナトリウム水溶液を混合して使用した。
A-2:製造例2で作製した炭素数16の内部オレフィンスルホン酸ナトリウム
A-3:製造例3で作製した炭素数18の内部オレフィンスルホン酸ナトリウム
A-4:製造例4で作製した炭素数18の内部オレフィンスルホン酸ナトリウム
B-2:ドデシル硫酸ナトリウム(MP Biomedicals, Inc社製)
B-3:ラウリン酸(花王株式会社製、ルナック L-98)
B-4:ジ(2-エチルヘキシル)スルホこはく酸ナトリウム(和光純薬工業株式会社製)
B-5:製造例5で作製したα―スルホパルミチン酸メチルエステルナトリウム
B-6:ポリオキシエチレンドデシルエーテルカルボン酸(Kao Chemicals GmbH社製、アキポ LM-26C)
B-7:N-ラウロイルグルタミン酸(味の素株式会社製、アミソフトLA-D)
B-8:N-ラウロイルサルコシン酸ナトリウム(和光純薬工業株式会社製)
C-2:ラウリルグリコシド(花王株式会社製、マイドール12)
C-3:ポリオキシエチレンアルキルエーテル(花王株式社製、エマルゲン 147)
Claims (10)
- 下記の成分A、B、C及びDを含有し、
成分A、B及びCの合計含有量が30質量%以上80質量%以下であり、
成分A及びBの合計含有量と成分Cの含有量の質量比(A+B)/Cが、20/80~80/20であり、
成分Aの含有量と成分Bの含有量の質量比A/Bが、98/2~45/55である界面活性剤組成物。
A 内部オレフィンスルホン酸及び/又はその塩
B 成分A以外のアニオン界面活性剤
C ノニオン界面活性剤
D 水 - 前記内部オレフィンスルホン酸及び/又はその塩の炭素数は、12以上24以下である請求項1に記載の界面活性剤組成物。
- 前記内部オレフィンスルホン酸及び/又はその塩は、スルホン酸基の位置が2位であるものを5質量%以上40質量%以下で含む請求項1又は2に記載の界面活性剤組成物。
- 前記内部オレフィンスルホン酸塩は、ヒドロキシアルカンスルホン酸塩(HAS)とオレフィンスルホン酸塩(IOS)を含む請求項1~3のいずれか1項に記載の界面活性剤組成物。
- 前記アニオン界面活性剤は、炭素数10~22の硫酸エステル塩、炭素数10~22のスルホン酸塩、炭素数10~22の脂肪酸塩、炭素数10~22のカルボン酸塩、炭素数10~22のリン酸エステル塩、及び炭素数10~22のアシル基を有するアミノ酸塩からなる群より選択される少なくとも1種である請求項1~4のいずれか1項に記載の界面活性剤組成物。
- 前記ノニオン界面活性剤は、ポリアルキレングリコール型ノニオン界面活性剤、多価アルコール型ノニオン界面活性剤、及び脂肪酸アルカノールアミドからなる群より選択される少なくとも1種である請求項1~5のいずれか1項に記載の界面活性剤組成物。
- 25℃における音叉型振動式粘度計で測定した粘度が、3000mPa・s以下である請求項1~6のいずれか1項に記載の界面活性剤組成物。
- 前記界面活性剤組成物は、洗浄剤である請求項1~7のいずれか1項に記載の界面活性剤組成物。
- 請求項1~7のいずれか1項に記載の界面活性剤組成物を用いる洗浄方法。
- 請求項1~7のいずれか1項に記載の界面活性剤組成物の洗浄剤としての使用。
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US16/324,209 US10941369B2 (en) | 2016-08-09 | 2017-08-07 | Surfactant composition |
CN201780048236.4A CN109563440A (zh) | 2016-08-09 | 2017-08-07 | 表面活性剂组合物 |
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WO2021100691A1 (ja) * | 2019-11-21 | 2021-05-27 | 花王株式会社 | 洗浄剤組成物 |
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TW201831665A (zh) | 2018-09-01 |
US10941369B2 (en) | 2021-03-09 |
TWI731140B (zh) | 2021-06-21 |
RU2019106318A (ru) | 2020-09-14 |
EP3498811A1 (en) | 2019-06-19 |
EP3498811A4 (en) | 2020-04-08 |
RU2742374C2 (ru) | 2021-02-05 |
JPWO2018030328A1 (ja) | 2019-06-13 |
US20190169536A1 (en) | 2019-06-06 |
AU2017310702A1 (en) | 2019-03-07 |
CN109563440A (zh) | 2019-04-02 |
RU2019106318A3 (ja) | 2020-09-14 |
JP7051685B2 (ja) | 2022-04-11 |
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