Classifications

• • 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
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
  • A61Q1/14—Preparations for removing make-up
• • 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
  • 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
  • C09K23/44—Ether carboxylic acids
• • 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
  • C11D9/00—Compositions of detergents based essentially on soap

Definitions

• the present invention relates to surfactant compositions and cleaning agents.
• Surfactants such as anionic surfactants are used in detergents for human skin and hair, and they exhibit moderate viscosity and produce foam with excellent foaming power, foam stability, and moisturizing power.
• a cleaning agent a cleaning agent containing sodium dodecanediol acetate is known (Patent Document 1).
• An object of the present invention is to provide a surfactant composition that can provide a detergent with excellent detergency against sebum and excellent moisturizing properties after washing.
• the present invention contains an alkyl hydroxy ether acetic acid (salt) (A) represented by the following general formula (1) and an alkyl hydroxy ether acetic acid (salt) (B) represented by the following general formula (2).
• a surfactant composition in which the total weight proportion of alkyl hydroxy ether acetic acid and its salt (B) is 0.05 to 1% by weight based on the total weight of alkyl hydroxy ether acetic acid and its salt (A), and the above surfactant
• This is a cleaning agent containing a cleaning agent composition.
• R 1 -CH(OH)-CH 2 -OCH 2 COOM 1 (1)
• R 1 represents an alkyl group having 8 to 12 carbon atoms
• M 1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.
• R 2 -O-CH(X 1 )CH(X 2 )-OCH 2 COOM 2 (2) [In the formula, one of X 1 and X 2 is a hydrogen atom, the other is an alkyl group having 8 to 12 carbon atoms, R 2 is a hydroxyalkyl group in which any one hydrogen atom bonded to the carbon atom bonded to the carbon atom with position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced with a hydroxyl group, When the number of carbon atoms in the alkyl group having 8 to 12 carbon atoms represented by X 1 or X 2 is n, the number of carbon atoms in R 2 is n+2, M 2 represents a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium. ]
• the detergent containing the surfactant composition of the present invention has excellent detergency against sebum, it is less sticky after washing. In addition, since the natural moisturizing factors present in the skin are not washed away, the skin remains highly moisturized after washing.
• the surfactant composition which is the first invention of the present application contains an alkyl hydroxy ether acetic acid (salt) (A) represented by the general formula (1) as the alkyl hydroxy ether acetic acid (salt) (A).
• R 1 -CH(OH)-CH 2 -OCH 2 COOM 1 (1) [In the formula, R 1 represents an alkyl group having 8 to 12 carbon atoms, and M 1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium. ]
• alkyl hydroxy ether acetic acid means alkyl hydroxy ether acetic acid and/or alkyl hydroxy ether acetate.
• R 1 represents an alkyl group having 8 to 12 carbon atoms.
• alkyl groups having 8 to 12 carbon atoms include n-octyl group, isooctyl group, 2-ethylhexyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, undecyl group, n-dodecyl group and isododecyl group. etc.
• R 1 from the viewpoint of detergency against sebum, an alkyl group having 8 to 10 carbon atoms is preferred, an alkyl group having 10 carbon atoms is more preferred, and an n-decyl group is particularly preferred. Further, preferably a straight-chain alkyl group.
• M 1 is a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.
• M1 from the viewpoint of detergency against sebum, sodium atom or triethanolammonium is preferable, and sodium atom is more preferable.
• alkyl hydroxy ether acetic acid (A) represented by general formula (1) include decyl hydroxy ether acetic acid (2-hydroxydecyl acetate), isodecyl hydroxy ether acetic acid (2-hydroxyisodecyl acetate), ethyl octyl hydroxy Etheracetic acid (2-hydroxyethyloctyl acetate), undecylhydroxyetheracetic acid (2-hydroxyundecyl acetate), isoundecylhydroxyetheracetic acid (2-hydroxyisoundecyl acetate), dodecylhydroxyetheracetic acid (2-hydroxyacetic acid) dodecyl), isododecyl hydroxyether acetate (2-hydroxyisododecyl acetate), tridecyl hydroxyether acetate (2-hydroxytridecyl acetate), tetradecyl hydroxyether acetate (2-hydroxytetradecyl acetate) and iso
• alkyl hydroxy ether acetate (A) represented by general formula (1) include sodium decyl hydroxy ether acetate, sodium isodecyl hydroxy ether acetate, sodium ethyl octyl hydroxy ether acetate, sodium undecyl hydroxy ether acetate, Sodium undecyl hydroxy ether acetate, sodium dodecyl hydroxy ether acetate, sodium isododecyl hydroxy ether acetate, sodium tridecyl hydroxy ether acetate, sodium tetradecyl hydroxy ether acetate, sodium isotetradecyl hydroxy ether acetate, potassium decyl hydroxy ether acetate, isodecyl Potassium hydroxy ether acetate, potassium ethyl octyl hydroxy ether acetate, potassium undecyl hydroxy ether acetate, potassium isoundecyl hydroxy ether acetate,
• alkyl hydroxy ether acetic acid represented by the general formula (1) and its salt (A) from the viewpoint of detergency against sebum, an alkyl hydroxy ether acetate represented by the general formula (1) is preferable, and a decyl hydroxy ether acetate represented by the general formula (1) is more preferable.
• the alkyl hydroxy ether acetic acid represented by the general formula (1) and its salt (A) can be obtained by a known method described in JP 2017-197732 A and the like. Specifically, 1.04 mol of sodium monochloroacetate is added to 1 mol of 1,2-diol having 10 to 14 carbon atoms, preferably at 30 to 80°C, more preferably at 50 to 70°C. After obtaining an aqueous solution containing crude sodium alkyl hydroxy ether acetate through the reaction, by adding hydrochloric acid, an aqueous surfactant solution containing alkyl hydroxy ether acetic acid (A) can be obtained.
• the alkyl hydroxy ether acetate (A) is obtained by neutralizing the obtained surfactant aqueous solution containing the alkyl hydroxy ether acetic acid (A) with an alkaline compound such as sodium hydroxide, potassium hydroxide, and triethanolamine.
• an alkaline compound such as sodium hydroxide, potassium hydroxide, and triethanolamine.
• the aqueous surfactant solution containing alkyl hydroxy ether acetic acid or its salt (A) may be used as it is in producing the surfactant composition of the present invention, or the aqueous surfactant solution may be desorbed by a known method such as an evaporator.
• a powder containing the alkyl hydroxy ether acetic acid or its salt (A) obtained by solvent may be used for producing a surfactant composition, or a surfactant aqueous solution containing the alkyl hydroxy ether acetic acid or its salt (A) may be used. and a powder containing alkyl hydroxy ether acetic acid or its salt (A) may be mixed and used for producing a surfactant composition.
• the molecular structure of alkyl hydroxy ether acetic acid can be determined by nuclear magnetic resonance (NMR) spectroscopy, and the types of cations that make up alkyl hydroxy ether acetate can be determined by radio frequency inductively coupled plasma emission (ICP) analysis and nuclear magnetic resonance. It can be identified by resonance (NMR) spectroscopy.
• NMR nuclear magnetic resonance
• a sodium standard solution [1,000 ppm ⁇ Fujifilm Wako Pure Chemical Industries, Ltd. ⁇ ] is diluted with ultrapure water to 50, 100, 200, 500, and 1,000 ppm to prepare a calibration curve solution. Furthermore, the surfactant aqueous solution or the powder containing the surfactant is diluted 200,000 times with ultrapure water. From the ICP-OES [product name: ICP-OES5900 ⁇ manufactured by Agilent Technologies, Inc. ⁇ ] measurement results, the sodium concentration contained in the surfactant aqueous solution or the surfactant-containing powder is calculated.
• the molar ratio of the sodium concentration contained in the obtained surfactant aqueous solution or surfactant-containing powder to the content of alkyl hydroxy ether acetate contained in the surfactant aqueous solution or surfactant-containing powder is If it is 0.8 to 1.2, it can be said that the alkyl hydroxy ether acetate contained in the obtained surfactant aqueous solution or surfactant-containing powder is a sodium salt.
• the molar ratio of the potassium concentration contained in the obtained surfactant aqueous solution or surfactant-containing powder to the content of alkyl hydroxy ether acetate contained in the surfactant aqueous solution or surfactant-containing powder is If it is 0.8 to 1.2, it can be said that the alkyl hydroxy ether acetate contained in the obtained surfactant aqueous solution or surfactant-containing powder is a potassium salt.
• the peak of the methylene group at the ⁇ -position in the carboxylic acid group of the alkyl hydroxy ether acetate appears at 3.0 to 3.2 ppm in the obtained H-NMR spectrum, and the peak of the alkyl hydroxy ether acetate appears at 3.6 to 3.7 ppm. If the peak area ratio to the peak of triethanolammonium is 1:2.4 to 1:3.6, the alkyl hydroxy ether acetate contained in the surfactant aqueous solution or the surfactant-containing powder is triethanolic. It can be said that it is an ethanol ammonium salt.
• alkyl hydroxy ether acetic acid and its salt (A) contained in the surfactant aqueous solution or surfactant was determined using high performance liquid chromatography (hereinafter sometimes abbreviated as HPLC), respectively, as described below. It can be measured by the method described in ⁇ Method for quantitative analysis of alkyl hydroxy ether acetic acid (salt) (A) by HPLC>.
• the concentration of undecanoic acid is 0.0006 g/L
• the concentration of undecanoic acid is 1.2 g/L
• the concentration of the surfactant aqueous solution or the powder containing the surfactant is 9.0 g/L.
• a sample solution having an undecanoic acid concentration of 1.2 g/L is prepared.
• sample solution and calibration curve solutions 1 to 3 were analyzed under the HPLC measurement conditions described below, and the peak of 1,2-dodecanediol that appeared at retention time 11.7 to 12.2 minutes in the obtained HPLC spectrum and retention time 13 Based on the peak area ratio of the alkyl hydroxy ether acetic acid (salt) (A) peak that appears at a retention time of 4 to 14.7 minutes and the undecanoic acid peak that appears at a retention time of 12.1 to 19.6 minutes, the sampled surfactant was determined.
• alkyl hydroxy ether acetic acid (salt) (A) contained in the aqueous surfactant solution or powder containing a surfactant. calculate.
• R 1 of the alkyl hydroxy ether acetic acid (salt) (A) is an alkyl group having a carbon number other than 10
• the corresponding 1,2-diol can be used instead of 1,2-dodecanediol. , can be quantified.
• the surfactant composition which is the first invention of the present application, contains an alkyl hydroxy ether acetic acid (salt) (B) represented by the general formula (2).
• R 2 -O-CH(X 1 )CH(X 2 )-OCH 2 COOM 2 (2)
• one of X 1 and X 2 is a hydrogen atom, the other is an alkyl group having 8 to 12 carbon atoms, R 2 is a hydroxyalkyl group in which any one hydrogen atom bonded to the carbon atom bonded to the carbon atom with position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced with a hydroxyl group
• M 2 represents a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium.
• one of X 1 and X 2 is a hydrogen atom, and the other is an alkyl group having 8 to 12 carbon atoms.
• alkyl groups having 8 to 12 carbon atoms include n-octyl group, isooctyl group, 2-ethylhexyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group, undecyl group, n-dodecyl group and isododecyl group. etc.
• the alkyl group having 8 to 12 carbon atoms is preferably an alkyl group having 8 to 10 carbon atoms, more preferably an alkyl group having 10 carbon atoms, particularly preferably an alkyl group having 10 carbon atoms, from the viewpoint of moisturizing the skin after washing. It is an n-decyl group. Further, preferably a straight-chain alkyl group.
• R 2 is a hydroxyalkyl group in which the hydrogen atom bonded to the carbon atom bonded to the carbon atom at position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced with a hydroxyl group.
• a hydroxyalkyl group means an alkyl group substituted with one or more hydroxyl groups.
• the carbon atom at position number 1 in the alkyl group having 10 to 14 carbon atoms represented by R 2 means the carbon atom bonded to the oxygen atom of the ether bond to which R 2 is bonded.
• Examples of the hydroxyalkyl group having 10 to 14 carbon atoms include hydroxydecyl group, hydroxyundecyl group, hydroxydodecyl group, hydroxytridecyl group, and hydroxytetradecyl group.
• R2 from the viewpoint of moisturizing the skin after washing, a hydroxyalkyl group having 10 to 12 carbon atoms is preferred, a hydroxyalkyl group having 10 carbon atoms is more preferred, and a hydroxydecyl group is particularly preferred. be.
• M 2 is a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.
• M2 from the viewpoint of moisturizing the skin after washing, sodium atom or triethanolammonium is preferable, and sodium atom is more preferable.
• alkyl hydroxy ether acetic acid (B) represented by the general formula (2) include 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetic acid, 2-(( 1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl)oxy)acetic acid, 2- ((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)acetic acid, 2 -((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)acetic acid, 2-((1-((2-hydroxyisotridecyl)oxy)isotride
• alkyl hydroxy ether acetate (B) represented by the general formula (2) which is a sodium salt is 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetic acid.
• Sodium 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)sodium acetate, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl )oxy) Sodium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)sodium acetate, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl- 2-yl)oxy)sodium acetate, 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)sodium acetate,
• alkyl hydroxy ether acetate (B) represented by the general formula (2) which is a potassium salt is 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy)acetic acid. Potassium, 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxyundecyl)oxy)undecyl-2-yl )oxy) potassium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)potassium acetate, 2-((1-((2-hydroxyisododecyl)oxy)isododecyl- 2-yl)oxy)potassium acetate, 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)potassium acetate,
• alkyl hydroxy ether acetate (B) represented by the general formula (2), which is a triethanol ammonium salt, is 2-((1-((2-hydroxydecyl)oxy)decyl-2-yl)oxy.
• Triethanolammonium acetate 2-((1-((2-hydroxyisodecyl)oxy)isodecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxyundecyl)oxy) )undecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-(( 2-hydroxyisododecyl)oxy)isododecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-((2-hydroxytridecyl)oxy)tridecyl-2-yl)oxy)triethanolammonium acetate, 2-((1-(
• an alkyl hydroxy ether acetate represented by the general formula (2) is preferable, and more preferably is 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)sodium acetate, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)sodium acetate, 2 -((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)sodium acetate, 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl) oxy) sodium acetate, 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)potassium acetate
• Sodium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate has the general formula (2) in which R 2 is a 2-hydroxydodecyl group, X 1 is a hydrogen atom, and X 2 is a decyl group, and M2 is a sodium atom.
• R 2 has a structure in which the hydrogen atom bonded to the 1st-position carbon atom of 2-dodecanol is replaced so as to bond to the oxygen atom of the ether bond.
• 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy)sodium acetate has the general formula (2) in which R 2 is a 2-hydroxydodecyl group, X 1 is a decyl group, and X 2 is a hydrogen atom. , M2 is a sodium atom. R 2 has a structure in which the hydrogen atom bonded to the 1st-position carbon atom of 2-dodecanol is replaced so as to bond to the oxygen atom of the ether bond.
• 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)sodium acetate has the general formula (2), where R 2 is a hydroxydodecyl group and X 1 is a hydrogen atom. , X 2 is a decyl group, and M 2 is a sodium atom. R 2 has a structure in which the hydrogen atom bonded to the 2-position carbon atom of 1-dodecanol is replaced so as to bond to the oxygen atom of the ether bond.
• R 2 is described as "1-hydroxydodecyl-2-yl" in the above compound name, but the carbon atom at position number 1 in R 2 in the present invention refers to 1 in the above compound name.
• This refers to the carbon atom that is bonded to the oxygen atom of the ether bond to which R 2 is bonded, rather than the carbon atom that is assumed to be the carbon atom in the ether bond. That is, the carbon atom corresponding to the carbon atom at the 2-position of 1-dodecanol is the carbon atom whose position number is 1 for R 2 in the present invention.
• 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)sodium acetate has the general formula (2) in which R 2 is a hydroxydodecyl group, X 1 is a decyl group, and X 2 is a decyl group.
• the hydrogen atom, M2 is a sodium atom.
• R 2 has a structure in which the hydrogen atom bonded to the 2-position carbon atom of 1-dodecanol is replaced so as to bond to the oxygen atom of the ether bond.
• R 2 is described as "1-hydroxydodecyl-2-yl" in the above compound name, but the carbon atom at position number 1 in R 2 in the present invention refers to 1 in the above compound name.
• This refers to the carbon atom that is bonded to the oxygen atom of the ether bond to which R 2 is bonded, rather than the carbon atom that is assumed to be the carbon atom in the ether bond. That is, the carbon atom corresponding to the carbon atom at the 2-position of 1-dodecanol is the carbon atom whose position number is 1 for R 2 in the present invention.
• the method for producing the alkyl hydroxy ether acetic acid and its salt (B) represented by the general formula (2) is as follows. First, 1,2-diol having 10 to 14 carbon atoms is subjected to dehydration condensation between two molecules to obtain a dimer of 1,2-diol. 1.04 mol of sodium monochloroacetate is added to 1 mol of the obtained 1,2-diol dimer, and the mixture is purified by SN2 reaction at preferably 30 to 80°C, more preferably 50 to 80°C. After obtaining an aqueous solution containing sodium alkyl hydroxy ether acetate, by adding hydrochloric acid, an aqueous surfactant solution containing alkyl hydroxy ether acetic acid (B) can be obtained.
• the alkyl hydroxy ether acetate (B) is obtained by neutralizing the resulting aqueous surfactant solution containing the alkyl ether hydroxy acetic acid (B) with an alkali compound such as sodium hydroxide, potassium hydroxide, and triethanolamine.
• an alkali compound such as sodium hydroxide, potassium hydroxide, and triethanolamine.
• the aqueous surfactant solution containing alkyl hydroxy ether acetic acid or its salt (B) may be used as it is in producing the surfactant composition of the present invention, or the aqueous surfactant solution may be desorbed by a known method such as an evaporator.
• a powder containing the alkyl hydroxy ether acetic acid or its salt (B) obtained by solvent may be used for producing a surfactant composition, or a surfactant aqueous solution containing the alkyl hydroxy ether acetic acid or its salt (B) and a powder containing alkyl hydroxyether acetic acid or its salt (B) may be mixed and used for producing a surfactant composition.
• the molecular structure of alkyl hydroxy ether acetate (B) can be determined by NMR spectroscopy, and the type of cations constituting alkyl hydroxy ether acetate (B) can be determined by ICP analysis and NMR spectroscopy. can.
• the ICP analysis method and NMR spectroscopy are based on the above-mentioned ⁇ Method for identifying the type of cations constituting the alkyl hydroxy ether acetate by ICP analysis method> and ⁇ Method for identifying the types of cations constituting the alkyl hydroxy ether acetate by NMR spectroscopy. Identification method>.
• alkyl hydroxy ether acetic acid and its salt (B) is measured using HPLC according to the method described in ⁇ Quantitative analysis method by HPLC of alkyl hydroxy ether acetic acid (salt) (B)> described below. be able to.
• the concentration of undecanoic acid is 1.2 g/L
• the concentration of the dimer of 5,1,2-dodecanediol is 0.0006 g/L
• the concentration of undecanoic acid is 1.2 g. /L
• a sample solution in which the concentration of the surfactant aqueous solution or the powder containing the surfactant is 9.0 g/L
• the concentration of undecanoic acid is 1.2 g/L.
• the sample solution and calibration curve solutions 4 to 6 were analyzed under the HPLC measurement conditions described below, and a mixture of 1,2-dodecanediol dimers appeared at a retention time of 9.0 to 9.5 minutes in the obtained HPLC spectrum.
• R 2 of the alkyl hydroxy ether acetic acid (salt) (B) is an alkyl group having a carbon number other than 12, and either X 1 or X 2 is an alkyl group having a carbon number other than 10, 1, Quantification can be achieved by using the corresponding 1,2-diol instead of 2-dodecanediol.
• the surfactant composition which is the first invention of the present application contains an alkyl hydroxy ether acetic acid (salt) (A) and an alkyl hydroxy ether acetic acid (salt) (B).
• the total weight proportion is 0.05 to 1% by weight based on the total weight of alkyl hydroxyether acetic acid and its salt (A).
• the surfactant composition if the total weight proportion of the alkyl hydroxy ether acetic acid and its salt (B) is less than 0.05% by weight based on the total weight of the alkyl hydroxy ether acetic acid and its salt (A), after washing.
• the moisture retention of the skin becomes insufficient and the total weight proportion of alkyl hydroxy ether acetic acid and its salt (B) exceeds 1% by weight with respect to the total weight of alkyl hydroxy ether acetic acid and its salt (A), Foam quality during cleaning becomes insufficient.
• the surfactant composition which is the first invention of the present application, has a moisture retention property in which the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) is greater than the total weight of the alkyl hydroxy ether acetic acid and its salt (A). From this point of view, the amount is preferably 0.1 to 0.8% by weight, more preferably 0.2 to 0.6% by weight.
• the total weight ratio of alkyl hydroxy ether acetic acid and its salt (A) is preferably preferably based on the total weight of the surfactant composition from the viewpoint of storage stability.
• the amount is 10 to 20% by weight, more preferably 15 to 18% by weight.
• the total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) is preferably set to the total weight of the surfactant composition from the viewpoint of storage stability.
• the amount is 0.01 to 0.9% by weight, more preferably 0.01 to 0.2% by weight, particularly preferably 0.01 to 0.05% by weight.
• the surfactant composition which is the first invention of the present application, contains alkyl hydroxy ether acetic acid and its salt (A) and alkyl hydroxy ether acetic acid and its salt (B) so that the content thereof becomes a predetermined ratio.
• the surfactant composition of the present invention may further contain any other components, and preferably contains water.
• the surfactant composition of the first invention of the present application contains water
• the water content is preferably 60 to 90% by weight based on the total weight of the surfactant composition. Preferably, it is more preferably 65 to 85% by weight.
• the water contained in the surfactant composition includes the water used as a reaction solvent when producing the alkyl hydroxy ether acetic acid or its salt (A) and the alkyl hydroxy ether acetic acid or its salt (B).
• alkaline ionized water In addition to regular water, purified water, hard water, soft water, natural water, deep ocean water, hot spring water, electrolyzed alkaline ionized water, electrolyzed acidic ionized water, ion-exchanged water, cluster water, etc., so as to maintain the specified weight ratio.
• purified water hard water, soft water, natural water, deep ocean water, hot spring water, electrolyzed alkaline ionized water, electrolyzed acidic ionized water, ion-exchanged water, cluster water, etc.
• B alkyl hydroxy ether acetic acid and its salt
• the surfactant composition which is the first invention of the present application is an amphoteric surfactant, alkyl hydroxy ether acetic acid and its salt (A), and alkyl hydroxy ether acetic acid and its salt (B), which are contained in the cleaning agent described below.
• amphoteric surfactant alkyl hydroxy ether acetic acid and its salt (A)
• alkyl hydroxy ether acetic acid and its salt (B) alkyl hydroxy ether acetic acid and its salt
• other anionic surfactants cationic surfactants
• nonionic surfactants water, oily components, solvents, humectants, chelating agents, conditioning agents, thickeners
• the surfactant composition may contain unreacted substances and residues of reaction catalysts during the synthesis of alkyl hydroxy ether acetic acid or its salt (A) and alkyl hydroxy ether acetic acid or its salt (B). good.
• the surfactant composition which is the first invention of the present application, comprises a paddle containing alkyl hydroxy ether acetic acid and its (A), alkyl hydroxy ether acetic acid and its salt (B), and water used as necessary in a predetermined ratio. It can be obtained by mixing in a known mixing device equipped with a stirring device such as a type stirring blade or a spiral type stirring blade.
• the content of alkyl hydroxy ether acetic acid and its salt (A) contained in the surfactant composition can be measured by HPLC.
• the HPLC measurement method and conditions are the same as the HPLC quantitative analysis method of alkyl hydroxy ether acetic acid (salt) (A) described above.
• the content of alkyl hydroxy ether acetic acid and its salt (B) contained in the surfactant composition can be measured by HPLC.
• the HPLC measurement method and conditions are the same as the HPLC quantitative analysis method of alkyl hydroxy ether acetic acid (salt) (B) described above.
• the surfactant composition which is the first invention of the present application, has excellent foaming properties and storage stability, so it can be preferably used as a raw material for cleaning agents.
• the second invention of the present application is a cleaning agent containing the surfactant composition of the first invention of the present application, and the alkyl hydroxy ether acetic acid ( (A) and alkyl hydroxyether acetic acid (salt) (B).
• cleaning agent in the present application refers to cleaning agents for hair or skin (shampoo, face wash, body soap, bar soap, cleansing, liquid soap, etc.), and the like.
• the detergent composition contains the surfactant composition of the first invention of the present application in an amount of 0.0% based on the total weight of the detergent.
• the content is preferably 1 to 10.0% by weight, and more preferably 1.0 to 3.0% by weight.
• the cleaning agent which is the second invention of the present application has a total weight ratio of the alkyl hydroxy ether acetic acid and its salt (B) to the total weight of the alkyl hydroxy ether acetic acid and its salt (A) from the viewpoint of moisture retention. It is preferably 0.05 to 1% by weight, more preferably 0.1 to 0.8% by weight, particularly preferably 0.2 to 0.6% by weight.
• the total weight ratio of alkyl hydroxy ether acetic acid and its salt (A) and alkyl hydroxy ether acetic acid and its salt (B) contained in the cleaning agent which is the second invention of the present application is 0.00175 to 1. .75% by weight is preferred, and 0.175-1.05% by weight is more preferred.
• the content of alkyl hydroxy ether acetic acid and its salt (A) contained in the cleaning agent can be measured by HPLC.
• the HPLC measurement method and conditions are the same as the HPLC quantitative analysis method of alkyl hydroxy ether acetic acid (salt) (A) described above.
• the total weight ratio of alkyl hydroxy ether acetic acid and its salt (A) is preferably 0.01 to 1.75 with respect to the total weight of the cleaning agent from the viewpoint of cleaning power. % by weight, more preferably 0.10 to 1.25% by weight.
• the content of alkyl hydroxy ether acetic acid and its salt (B) contained in the cleaning agent can be measured by HPLC.
• the HPLC measurement method and conditions are the same as the HPLC quantitative analysis method of alkyl hydroxy ether acetic acid (salt) (B) described above.
• the total weight ratio of alkyl hydroxy ether acetic acid and its salt (B) is preferably 0.000006 to 0.003 with respect to the total weight of the cleaning agent from the viewpoint of cleaning power. % by weight, more preferably 0.001 to 0.002% by weight.
• the cleaning agent according to the second invention of the present application may contain any other components.
• Optional other ingredients include amphoteric surfactants, other anionic surfactants, cationic surfactants, nonionic surfactants, water, oily ingredients, solvents, humectants, chelating agents, conditioning agents, thickeners.
• Known cosmetic ingredients such as whitening agents, pH adjusters, refreshing agents, coloring agents, ultraviolet scattering agents, ultraviolet absorbers, preservatives, and antioxidants may be mentioned.
• amphoteric surfactants include alkyl dimethyl acetate betaines, fatty acid amidopropyl betaines, alkylimidazolinium betaines, sulfobetaine-type amphoteric surfactants, and amphoteric amino acid-based surfactants.
• alkyldimethylaminoacetic acid betaine examples include lauryldimethylaminoacetic acid betaine [also known as laurylbetaine], myristyldimethylaminoacetic acid betaine [also known as myristylbetaine], and stearyldimethylaminoacetic acid betaine [also known as stearylbetaine].
• fatty acid amidopropyl betaine examples include amidopropyl betaine laurate [also known as lauramidopropyl betaine], amidopropyl betaine myristate [also known as myristamidopropyl betaine], amidopropyl betaine isostearate, and amidopropyl betaine coconut oil fatty acid [also known as: cocamidopropyl betaine] and the like.
• alkylimidazolinium betaines examples include 2-coconut oil fatty acid-N-hydroxyethyl-N-hydroxyethylimidazolinium betaine, N-lauroyl-N'-carboxymethyl-N'-hydroxyethylethylenediamine sodium [also known as lauroamphoacetic acid] Na] and N-coconut oil fatty acid acyl-N'-carboxymethyl-N'-hydroxyethylethylenediamine sodium [also known as sodium cocoamphoacetate].
• sulfobetaine type amphoteric surfactants examples include lauramidopropylhydroxysultaine and cocamidopropylhydroxysultaine.
• amphoteric amino acid surfactants include sodium lauryl aspartate, sodium myristyl aspartate, sodium lauryl- ⁇ -aminopropionate, and sodium lauroylmethyl- ⁇ -alanine [also known as lauroylmethylalanine Na].
• anionic surfactants include ether carboxylic acids or salts thereof (hereinafter referred to as ether carboxylates or salts thereof) other than alkyl hydroxy ether acetic acids and their salts (A) and alkyl hydroxy ether acetic acids and their salts (B). ), sulfuric acid ester salts, sulfonic acid salts, phosphoric acid ester salts, fatty acid salts, and acylated amino acid salts.
• ether carboxylates or salts thereof include polyoxyethylene (average degree of polymerization 4) sodium lauryl ether carboxylate [also known as polyoxyethylene (average degree of polymerization 4) sodium lauryl ether acetate, sodium laureth-4 carboxylate], Oxyethylene (average degree of polymerization 6) sodium lauryl ether carboxylate [also known as: Na laureth-6 carboxylate], polyoxyethylene (average degree of polymerization 4) sodium tridecyl ether carboxylate [also known as Na trideceth-4 carboxylate], and Examples include polyoxyethylene (average degree of polymerization 7) sodium tridecyl ether carboxylate [also known as sodium trideceth-7 carboxylate].
• Sulfate ester salts include sodium lauryl sulfate [also known as Na lauryl sulfate], polyoxyethylene (average degree of polymerization 2) sodium lauryl ether sulfate [also known as Na laureth-2 sulfate], polyoxyethylene (average degree of polymerization 3) lauryl Sodium ether sulfate [also known as: Na laureth-3 sulfate], polyoxyethylene (average degree of polymerization 3) lauryl ether sulfate triethanolamine [also known as laureth-3 sulfate TEA], polyoxyethylene (average degree of polymerization 3) coconut oil fatty acid Sodium monoethanolamide sulfate [also known as PEG-3 coconut fatty acid amide MEA sodium sulfate] and polyoxyethylene (average degree of polymerization 3) alkyl (carbon number 12-13) ether sodium sulfate [also known as (C12, C13) Pareth-3] Na sulfate] and
• sulfonate salts include sodium olefin (C14-16) sulfonate [also known as Na olefin (C14-16) sulfonate], sodium dodecylbenzenesulfonate [also known as Na dodecylbenzenesulfonate], polyoxyethylene (average polymerized Degree 2) Disodium lauryl sulfosuccinate [also known as 2Na laureth sulfosuccinate], disodium lauryl sulfosuccinate [also known as 2Na lauryl sulfosuccinate], polyoxyethylene (average degree of polymerization 5) disodium lauroyl ethanolamide sulfosuccinate, etc. Can be mentioned.
• phosphate ester salts include sodium lauryl phosphate [also known as Na lauryl phosphate] and sodium polyoxyethylene lauryl ether phosphate [also known as trilaureth-4 phosphate].
• fatty acid salts include salts of myristic acid (sodium myristate [also known as Na myristate], potassium myristate [also known as K myristate], triethanolamine myristate [also known as TEA myristate], etc.), lauric acid salts, etc.
• Salts sodium laurate [also known as: Na laurate], potassium laurate [also known as: K laurate], triethanolamine laurate [also known as: TEA laurate], etc.
• salts of stearic acid sodium stearate [also known as: salts of palmitic acid (sodium palmitate [also known as Na palmitate] and triethanolamine palmitate [also known as TEA palmitate]), etc.
• acylated amino acid salts include N-coconut oil fatty acid acylglycine potassium [also known as cocoylglycine K], N-coconut oil fatty acid methyltaurine sodium [also known as cocoyl methyltaurine Na], and N-coconut oil fatty acid sarcosine sodium [also known as: cocoylsarcosine Na], N-lauroylsarcosine sodium [also known as lauroylsarcosine Na], N-coconut oil fatty acid sarcosine triethanolamine [also known as acylglutamate TEA], N-coconut oil fatty acid acyl-L-glutamate triethanolamine [also known as : cocoyl glutamate TEA], sodium N-coconut oil fatty acyl-L-glutamate [also known as: Na cocoyl glutamate], and lauroyl-L-glutamate triethanolamine [also known as: lauroyl glutamate TE
• cationic surfactants include quaternary ammonium salts and amine salts.
• Quaternary ammonium salts include stearyltrimethylammonium chloride [alias: steartrimonium chloride], behenyltrimethylammonium chloride [alias: behentrimonium chloride], distearyldimethylammonium chloride [alias: distearyldimonium chloride], and ethyl Examples include lanolin sulfate fatty acid aminopropylethyldimethylammonium [also known as quaternium-33].
• amine salts include stearic acid diethylaminoethylamide lactate [also known as stearamide ethyl diethylamine lactate] and behenic acid dimethylaminoethylamide lactate [also known as behenamide propyl dimethylamine lactate].
• nonionic surfactants include alkylene oxide (carbon numbers 2 to 8) adducts of alcohols having carbon numbers of 4 to 24, and polymers of fatty acids having carbon numbers of 8 to 24 and alcohols or alkylene oxides (carbon numbers 2 to 8).
• examples include esters or ethers of, alkylene oxide adducts of higher fatty acid esters of polyhydric (divalent to decavalent) alcohols, glycerin fatty acid esters, polyglycerin fatty acid esters, and fatty acid alkanolamides.
• alkylene oxide (carbon number 2 to 8) adducts of alcohols having 4 to 24 carbon atoms examples include polyoxyethylene (average degree of polymerization 10) polyoxypropylene (average degree of polymerization 7) butyl ether [also known as PPG-7 buteth-10 ], polyoxyethylene (average degree of polymerization 20) lauryl ether [also known as Laureth-20], polyoxyethylene (average degree of polymerization 20) oleyl ether [also known as Oles-20], polyoxyethylene (average degree of polymerization 12) poly Examples include oxypropylene (average degree of polymerization 2) cetyl ether [also known as: PPG-2 Ceteth-12] and a mixture of polyoxyethylene cetearyl ether and polyoxyethylene oleyl ether [also known as Ceretos-5].
• esters or ethers of fatty acids having 8 to 24 carbon atoms and polymers of alcohols or alkylene oxides (having 2 to 8 carbon atoms) include glyceryl monostearate [also known as glyceryl stearate], glyceryl monocaprylate [also known as caprylic acid] Glyceryl monomyristate [also known as glyceryl myristate], glyceryl monooleate [also known as glyceryl oleate], ethylene glycol monostearate [also known as glycol stearate], sorbitan monolaurate [also known as sorbitan laurate] , sorbitan monopalmitate [also known as sorbitan palmitate], sorbitan monostearate [also known as sorbitan stearate], sorbitan monooleate [also known as sorbitan oleate], sorbitan coconut oil fatty acid, polyoxyethylene monooleate (average Polymerization
• Alkylene oxide adducts of higher fatty acid esters of polyhydric (divalent to decavalent) alcohols include addition polymerization of polyethylene oxide (average degree of polymerization 6) to glycerin esters of caprylic acid and capric acid [also known as (caprylic acid) / capric acid) PEG-6 glycerides], polyoxyethylene monolaurate (average degree of polymerization 10) sorbitan [also known as PEG-10 sorbitan laurate], polyoxyethylene monolaurate (average degree of polymerization 80) sorbitan [also known as lauric acid PEG-80 sorbitan], polyoxyethylene monooleate (average degree of polymerization 6) sorbitan [also known as PEG-6 sorbitan oleate], polyoxyethylene monooleate (average degree of polymerization 3) sorbitan [also known as PEG- oleate] 3 sorbitan], polyoxyethylene monooleate (average degree of polymerization 40)
• polyglycerin fatty acid esters examples include decaglyceryl monooleate [also known as polyglyceryl oleate-10], decaglyceryl monolaurate [also known as polyglyceryl laurate], decaglyceryl isostearate [also known as polyglyceryl isostearate-10], Polyglyceryl distearate [also known as polyglyceryl distearate-10], polyglyceryl stearate [also known as polyglyceryl stearate-10], hexaglyceryl polyricinoleate [also known as polyglyceryl-6 polyricinoleate], and diglyceryl monoisostearate [also known as: Polyglyceryl-2 isostearate] and the like.
• decaglyceryl monooleate also known as polyglyceryl oleate-10
• decaglyceryl monolaurate also known as polyglyceryl laurate
• decaglyceryl isostearate
• fatty acid alkanolamides examples include coconut oil fatty acid monoethanolamide [also known as cocamide MEA], coconut oil fatty acid N-methylethanolamide [also known as cocamide methyl MEA], and coconut oil fatty acid diethanolamide [also known as cocamide DEA].
• Examples of water include ordinary water, purified water, hard water, soft water, natural water, deep ocean water, hot spring water, electrolyzed alkaline ionized water, electrolyzed acidic ionized water, ion-exchanged water, cluster water, and the like.
• oily components include liquid oils, solid oils, hydrocarbon oils, synthetic ester oils, silicone oils, and essential oils.
• Liquid oils include avocado oil, camellia oil, turtle oil, macadamia seed oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, sasanqua oil, castor oil, linseed oil, Safflower oil, cottonseed seed oil, soybean oil, peanut oil, tea seed oil, rice bran oil, jojoba oil, rice germ oil, glyceryl tri-2-ethylhexanoate [also known as triethylhexanoin], and triisopalmitic acid Examples include glyceryl [also known as triisopalmitine].
• Solid fats and oils include cacao butter, coconut oil, candelilla wax, beeswax, shea butter, horse oil, hydrogenated coconut oil, palm oil, beef tallow, lanolin, hydrogenated beef tallow, palm kernel oil, hydrogenated palm oil, pork fat. , Japanese owl oil, hydrogenated castor oil, and the like.
• Hydrocarbon oils include 2,2,4,6,6-pentamethylheptane [also known as isododecane], 2,2,4,4,6,8,8-heptamethylnonane [also known as isohexadecane], and hexadecane.
• Methyltetracosane also known as squalane
• 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene also known as squalene
• petrolatum, paraffin, water examples include added polyisobutene, ozokerite, 2,6,10,14-tetramethylpentadecane, ceresin, and microcrystalline wax.
• Synthetic ester oils include isopropyl myristate, cetyl ethylhexanoate, octyldodecyl myristate, cetyl palmitate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl ethylhexanoate, Cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl hydroxystearate, glycol diethylhexanoate, neopentyl glycol dicaprate, triester of caprylic acid, capric acid, and glycerin [also known as tri(capryl)] Glyceryl acid/capric acid], hydroxystearic acid, hydroxystearic acid, hexaester of
• silicone oil examples include chain polysiloxanes, cyclic polysiloxanes, and modified polysiloxanes (amino-modified polysiloxanes, polyether-modified siloxanes, alkyl-modified polysiloxanes, fluorine-modified polysiloxanes, etc.).
• linear polysiloxanes examples include methylphenylpolysiloxane [also known as diphenyl dimethicone], caprylylmethicone, dimethicone, dimethylpolysiloxane crosslinked with divinyldimethylpolysiloxane [also known as (dimethicone/vinyl dimethicone) crosspolymer], and phenylvinyl dimethyl.
• examples include dimethylpolysiloxane copolymer crosslinked with polysiloxane [also known as (dimethicone/phenylvinyl dimethicone) crosspolymer], etc.
• cyclic polysiloxane examples include decamethylcyclopentasiloxane [also known as cyclopentasiloxane] and dodecamethylcyclohexasiloxane [also known as cyclohexasiloxane].
• Modified polysiloxanes include aminopropyl dimethicone, alkyl (C26-28) dimethicone, alkyl (C30-45) dimethicone, polyoxyethylene (average degree of polymerization 10)/methylpolysiloxane copolymer [also known as PEG-10 dimethicone] , polyoxyethylene (average degree of polymerization 12)/methylpolysiloxane copolymer [also known as PEG-12 dimethicone] and polyoxyethylene (average degree of polymerization 9) dimethylsiloxyethyl dimethicone [also known as PEG-9 polydimethylsiloxyethyl dimethicone] ] etc.
• Solvents include ethanol, isoprene diol [also known as isopentyldiol], denatured alcohol, dipropylene glycol [also known as DPG], 1,2-hexanediol [also known as 1,2-hexanediol], isododecane, isopropanol, acetic acid.
• examples include butyl, diethylene glycol monoethyl ether [also known as ethoxydiglycol], and propylene glycol [also known as PG].
• Moisturizers include glycerin, 1,3-butylene glycol [also known as BG], hydrogenated rapeseed oil alcohol [also known as hydrogenated rapeseed oil alcohol], sorbitol, sodium acetate [also known as sodium lactate], sodium pyrrolidone carboxylate [also known as :PCN-Na], sodium hyaluronate [also known as hyaluronate Na], and sodium chondroitin sulfate [also known as chondroitin sulfate Na].
• BG 1,3-butylene glycol
• hydrogenated rapeseed oil alcohol also known as hydrogenated rapeseed oil alcohol
• sorbitol sodium acetate [also known as sodium lactate]
• sodium pyrrolidone carboxylate also known as :PCN-Na
• sodium hyaluronate also known as hyaluronate Na
• sodium chondroitin sulfate Na also known as chondroitin
• Chelating agents include ethylenediaminetetraacetic acid [also known as EDTA], disodium salt of ethylenediaminetetraacetic acid [also known as EDTA-2Na], sodium polyphosphate [also known as Na polyphosphate], disodium pyrophosphate [also known as pyrophosphoric acid] 2Na], gluconic acid, sodium gluconate [also known as Na gluconate], and ascorbic acid.
• Conditioning agents include polymers of quaternary ammonium salts obtained by adding glycidyltrimethylammonium chloride to hydroxyethylcellulose [also known as polyquaternium-10], polymers of quaternary ammonium salts obtained from acrylic acid amide and dimethyldiallylammonium chloride, and Copolymer [also known as: polyquaternium-7], copolymer of dimethyldiallylammonium chloride and acrylic acid [also known as polyquaternium-22], copolymer of vinyl acetate and vinyl pyrrolidone [also known as (VP/VA) copolymer], guar gum Quaternary ammonium salt added with glycidyltrimethylammonium chloride [also known as guar hydroxypropyltrimonium chloride], polyethylene glycol 20000 [also known as PEG-400], sodium polyacrylate [also known as Na polyacrylate], hydroxyethyl cellulose, and Examples include D-pantothenyl alcohol [also known as panth
• Thickeners include guar gum, xanthan gum, starch, behenyl alcohol, stearyl alcohol, cetearyl alcohol, cetanol, myristyl alcohol, carboxyvinyl polymer [also known as carbomer], hydroxypropyl methylcellulose, polyvinyl alcohol, sodium polyacrylate [also known as poly Sodium acrylate], sodium salt of starch grafted with acrylic acid [also known as Na acrylate grafted starch], dimethyl distearylammonium hectorite [also known as disteardimonium hectorite], talc, coconut oil fatty acid N- Methylethanolamide [also known as cocamide methyl MEA], glycol distearate and acrylic acid/alkyl methacrylate (C10-30) copolymer [also known as (acrylates/alkyl acrylate (C10-30)) crosspolymer], etc. Can be mentioned.
• whitening agents examples include tranexamic acid, arbutin, and hydroquinone.
• pH adjuster examples include lactic acid, citric acid, phosphoric acid, malic acid, tartaric acid, hydrochloric acid, acetic acid, sodium hydroxide, potassium hydroxide, and triethanolamine.
• refreshing agents include menthol, peppermint oil, thymol, methyl salicylate, and camphor.
• colorants examples include Blue No. 1, Blue No. 2, Green No. 3, and Red No. 1.
• Examples of the ultraviolet scattering agent include titanium oxide and zinc oxide.
• ultraviolet absorber examples include ethylhexyl methoxycinnamate, ester of dimethyl para-aminobenzoic acid and 2-ethylhexyl alcohol [also known as dimethyl PABA ethylhexyl], and t-butylmethoxydibenzoylmethane.
• preservatives examples include phenoxyethanol, o-cymen-5-ol, methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, and isobutylparaben.
• Antioxidants include vitamin E [also known as tocopherol], dibutylated hydroxytoluene [also known as BHT], butylated hydroxyanisole [also known as BHA], dipotassium glycyrrhizinate [also known as 2K glycyrrhizinate], ascorbyl palmitate, and rosemary. Examples include leaf extract.
• the types and contents of known cosmetic ingredients that can be used as needed in the cleaning agent, which is the second invention of the present application, are as follows.
• the amphoteric surfactant, other anionic surfactant, cationic surfactant, nonionic surfactant, water, oily component, solvent, and humectant are each preferably 50% by weight based on the total weight of the cleaning agent. % or less, more preferably 10% by weight or less.
• the content of the chelating agent, conditioning agent, thickener, and whitening agent is preferably 30% by weight or less, and more preferably 10% by weight or less, based on the total weight of the detergent.
• the pH adjuster, cooling agent, coloring agent, ultraviolet scattering agent, ultraviolet absorber, preservative, and antioxidant are each preferably 10% by weight or less, and more preferably 5% by weight, based on the total weight of the cleaning agent. It is as follows.
• the cleaning agent which is the second invention of the present application, can be manufactured by mixing the surfactant composition and any other components using a known stirrer.
• agitators used in manufacturing the cleaning agent, which is the second invention of the present application include Henschel mixers, ball mills, jet mills, kneaders, planetary mixers, sand mills, attritors, ribbon blenders, disper mixers, and homomixers.
• a disper mixer can be preferably used.
• the cleaning agent which is the second invention of the present application, is preferably solid, liquid or paste at 25°C, and liquid is more preferable from the viewpoint of ease of handling.
• the cleaning agent of the present invention is a shampoo
• the shampoo preferably contains, for example, the following components.
• an active ingredient means a component obtained by removing water from the raw material of each component.
• anionic surfactants include polyoxyethylene (average degree of polymerization 2) sodium lauryl ether sulfate, polyoxyethylene (average degree of polymerization 4) sodium lauryl ether acetate, sodium N-coco fatty acid acyl-L-glutamate, At least one selected from the group consisting of sodium N-lauroylsarcosinate and sodium olefin (C14-16) sulfonate is preferred.
• the shampoo may contain 3.0 to 10.0% by weight of polyoxyethylene (average degree of polymerization 2) sodium lauryl ether sulfate as an active ingredient, based on the weight of the entire shampoo.
• the shampoo may contain 1.0 to 5.0% by weight of polyoxyethylene (average degree of polymerization 4) sodium lauryl ether acetate as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 3.0 to 10.0% by weight of N-coconut fatty acyl-L-sodium glutamate as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 1.0 to 5.0% by weight of N-lauroylsarcosinate sodium, calculated as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 1.0 to 10.0% by weight of sodium olefin (C14-16) sulfonate, calculated as an active ingredient, based on the total weight of the shampoo.
• the amphoteric surfactant is preferably at least one selected from the group consisting of cocamidopropyl betaine and 2-coconut oil fatty acid-N-hydroxyethyl-N-hydroxyethylimidazolinium betaine.
• the shampoo may contain 1.0 to 5.0% by weight of cocamidopropyl betaine as an active ingredient, based on the total weight of the shampoo.
• the shampoo contains 1.0 to 5.0% by weight of 2-coconut oil fatty acid-N-hydroxyethyl-N-hydroxyethylimidazolinium betaine as an active ingredient, based on the weight of the entire shampoo. Good too.
• the shampoo may contain 1.0 to 5.0% by weight of 1,3-butylene glycol as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 1.0 to 5.0% by weight of glycerin as an active ingredient, based on the total weight of the shampoo.
• the conditioning agent is preferably at least one selected from the group consisting of polyquaternium-22, polyquaternium-7, and polyquaternium-10.
• the shampoo may contain 0.1 to 1.0% by weight of polyquaternium-22 as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 0.05 to 0.5% by weight of polyquaternium-7 as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 0.1 to 1.0% by weight of polyquaternium-10 as an active ingredient, based on the total weight of the shampoo.
• Dimethicone is preferred as the oily component.
• the shampoo may contain 0.1 to 1.0% by weight of dimethicone as an active ingredient, based on the total weight of the shampoo.
• the shampoo may contain 0.05 to 0.5% by weight of EDTA-2Na as an active ingredient, based on the total weight of the shampoo.
• coconut oil fatty acid N-methylethanolamide is preferred.
• the shampoo may contain 1.0 to 5.0% by weight of coconut oil fatty acid N-methylethanolamide as an active ingredient, based on the total weight of the shampoo.
• PEG-160 sorbitan triisostearate is preferred.
• the shampoo may contain 1.0 to 5.0% by weight of PEG-160 sorbitan triisostearate as an active ingredient, based on the total weight of the shampoo.
• Menthol is preferred as a refreshing agent.
• the shampoo may contain 0.5 to 3.0% by weight of menthol as an active ingredient, based on the total weight of the shampoo.
• Citric acid is preferred as the pH adjuster.
• the shampoo may contain 0.05 to 0.5% by weight of citric acid as an active ingredient, based on the total weight of the shampoo.
• compositions of each component in terms of active ingredients include the following compositions.
• Alkyl hydroxy ether acetic acid (salt) (A): 0.15-1.30% by weight Alkyl hydroxy ether acetic acid (salt) (B): 0.00010 to 0.0040% by weight
• Other anionic surfactants 3.0 to 20.0% by weight
• Amphoteric surfactant 1.0 to 5.0% by weight
• Moisturizer 1.0-5.0% by weight
• Conditioning agent 0.1-1.0% by weight
• Oily component 0.1-1.0% by weight
• Chelating agent 0.05-0.5% by weight
• Thickener 1.0-5.0% by weight
• Nonionic surfactant 1.0 to 5.0% by weight
• Coolant 0.5-3.0% by weight pH adjuster: 0.05-0.5% by weight
• the cleansing agent of the present invention is a facial cleanser for pump formers
• the facial cleanser for pump formers contains, for example, the following components.
• the other anionic surfactant at least one selected from the group consisting of lauroyl-L-glutamate triethanolamine and sodium olefin (C14-16) sulfonate is preferred.
• the face wash for pump formers may contain 1.0 to 10.0% by weight of lauroyl-L-glutamate triethanolamine as an active ingredient, based on the entire weight of the face wash for pump formers. good.
• the face wash for pump formers contains 0.5 to 3.0% by weight of sodium olefin (C14-16) sulfonate as an active ingredient, based on the entire weight of the face wash for pump formers. Good too.
• cocamidopropyl betaine is preferred.
• the pump former facial cleanser may contain 0.5 to 3.0% by weight of cocamidopropyl betaine as an active ingredient, based on the entire weight of the pump former facial cleanser.
• polyquaternium-7 is preferred.
• the pump former facial cleanser may contain 0.05 to 0.5% by weight of polyquaternium-7 as an active ingredient, based on the entire weight of the pump former facial cleanser.
• compositions of each component calculated as active ingredients include the following compositions.
• Alkyl hydroxy ether acetic acid (salt) (A): 0.20 to 1.00% by weight
• Other anionic surfactants 1.0 to 10.0% by weight
• Amphoteric surfactant 0.5-3.0% by weight
• Conditioning agent 0.05-0.5% by weight
• the cleansing agent of the present invention is a cream facial cleanser
• the cream facial cleanser preferably contains, for example, the following components.
• the cream facial cleanser may contain 1.0 to 3.0% by weight of sodium N-coconut oil fatty acyl-L-glutamate as an active ingredient, based on the weight of the entire cream facial cleanser.
• the cream facial cleanser may contain 5.0 to 20.0% by weight of N-coconut oil fatty acid acylglycine potassium as an active ingredient, based on the total weight of the cream facial cleanser.
• the cream facial cleanser may contain 0.5 to 5.0% by weight of lauric acid salt as an active ingredient, based on the total weight of the cream facial cleanser.
• the cream facial cleanser may contain 0.5 to 20.0% by weight of stearic acid salt as an active ingredient, based on the total weight of the cream facial cleanser.
• the cream facial cleanser may contain 5.0 to 20.0% by weight of palmitic acid salt as an active ingredient, based on the total weight of the cream facial cleanser.
• the other anionic surfactant contains a fatty acid salt, it is assumed that all the fatty acids are potassium salts, and the weight of the potassium salt of the fatty acid is regarded as the weight of the fatty acid salt.
• cocamidopropyl betaine is preferred.
• the cream facial cleanser may contain 0.5 to 3.0% by weight of cocamidopropyl betaine as an active ingredient, based on the weight of the entire cream facial cleanser.
• Glycerin is preferred as a humectant.
• the cream facial cleanser may contain 5.0 to 20.0% by weight of glycerin as an active ingredient, based on the total weight of the cream facial cleanser.
• polyquaternium-7 is preferred.
• the cream facial cleanser may contain 0.01 to 0.10% by weight of polyquaternium-7 as an active ingredient, based on the weight of the entire cream facial cleanser.
• the cream facial cleanser may contain 0.05 to 0.30% by weight of vitamin E as an active ingredient, based on the total weight of the cream facial cleanser.
• the thickener is preferably at least one selected from the group consisting of coconut oil fatty acid N-methylethanolamide and glycol distearate.
• the cream facial cleanser may contain 1.0 to 3.0% by weight of coconut oil fatty acid N-methylethanolamide as an active ingredient, based on the total weight of the cream facial cleanser.
• the cream facial cleanser may contain 1.0 to 3.0% by weight of glycol distearate as an active ingredient, based on the total weight of the cream facial cleanser.
• the cream facial cleanser may contain 3.0 to 10.0% by weight of PEG-190 distearate as an active ingredient, based on the total weight of the cream facial cleanser.
• the cream facial cleanser may contain 3.0 to 10.0% by weight of potassium hydroxide as an active ingredient, based on the total weight of the cream facial cleanser.
• compositions of each component calculated as active ingredients include the following compositions.
• Alkyl hydroxy ether acetic acid (salt) (A): 0.015-1.5% by weight Alkyl hydroxy ether acetic acid (salt) (B): 0.000005 to 0.003% by weight
• Other anionic surfactants 10.0 to 40.0% by weight
• Amphoteric surfactant 0.5-3.0% by weight
• Moisturizer 5.0-20.0% by weight
• Conditioning agent 0.01-0.10% by weight
• Thickener 1.0-10.0% by weight
• Nonionic surfactant 3.0 to 10.0% by weight pH adjuster: 3.0 to 10.0% by weight
• the present disclosure (1) comprises an alkyl hydroxy ether acetic acid (salt) (A) represented by the following general formula (1) and an alkyl hydroxy ether acetic acid (salt) (B) represented by the following general formula (2).
• R 1 -CH(OH)-CH 2 -OCH 2 COOM 1 (1)
• R 1 represents an alkyl group having 8 to 12 carbon atoms
• M 1 represents a hydrogen atom, a sodium atom, a potassium atom, or triethanolammonium.
• R 2 -O-CH(X 1 )CH(X 2 )-OCH 2 COOM 2 (2) [In the formula, one of X 1 and X 2 is a hydrogen atom, the other is an alkyl group having 8 to 12 carbon atoms, R 2 is a hydroxyalkyl group in which any one hydrogen atom bonded to the carbon atom bonded to the carbon atom with position number 1 in an alkyl group having 10 to 14 carbon atoms is replaced with a hydroxyl group, When the number of carbon atoms in the alkyl group having 8 to 12 carbon atoms represented by X 1 or X 2 is n, the number of carbon atoms in R 2 is n+2, M 2 represents a hydrogen atom, a sodium atom, a potassium atom or triethanolammonium. ]
• the present disclosure (2) is a cleaning agent containing the surfactant composition according to the present disclosure (1).
• ⁇ Manufacture example 1> In a 1 L four-necked flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer, 50 g of 1,2-dodecanediol [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.] and toluene [manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.] were added.
• Powder 1 containing a surfactant was a powder containing 40% by weight of sodium decylhydroxyether acetate as alkylhydroxyether acetic acid (salt) (A).
• a sample solution was prepared in which the concentration of the calibration curve solution 3 and the powder 1 containing a surfactant was 9.0 g/L, and the concentration of undecanoic acid was 1.2 g/L.
• the sample solution and calibration curve solutions 1 to 3 were analyzed by HPLC under the conditions described below, and the peak of 1,2-dodecanediol that appeared at retention time 11.7 to 12.2 minutes in the obtained HPLC spectrum and retention time 13 Based on the peak area ratio of the alkyl hydroxy ether acetic acid (salt) (A) peak that appears at a retention time of 4 to 14.7 minutes and the undecanoic acid peak that appears at a retention time of 12.1 to 19.6 minutes, the sampled surfactant was determined. Based on the content of undecanoic acid contained in Powder 1 containing surfactant, the content of alkyl hydroxy ether acetic acid (salt) (A) contained in Powder 1 containing surfactant was calculated.
• ⁇ Manufacture example 2> In a 300 mL beaker, add 100 g of the surfactant-containing powder 1 produced in Production Example 1, 2 g of ion-exchanged water, and 21.8 g of a 35% hydrochloric acid aqueous solution [manufactured by Kishida Chemical Co., Ltd.], and heat to 70°C. The mixture was stirred for 60 minutes to obtain 124 g of surfactant aqueous solution 1.
• ⁇ Manufacture example 3> In a 50 mL beaker, add 33.3 g of the surfactant aqueous solution 1 produced in Production Example 2, 16.5 g of ion exchange water, and 6 g of triethanolamine [manufactured by Tokyo Kasei Kogyo Co., Ltd.], and heat it to 70°C. After stirring for several minutes, 55.8 g of surfactant aqueous solution 2 was obtained.
• ⁇ Manufacture example 4> In a 50 mL beaker, add 33.3 g of the surfactant aqueous solution 1 produced in Production Example 2, 17.5 g of ion-exchanged water, and potassium hydroxide [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.], and heat to 70°C. The mixture was stirred for 60 minutes to obtain 52.8 g of surfactant aqueous solution 3.
• ⁇ Manufacture example 5> In a 1 L four-necked flask equipped with a stirrer, reflux condenser, and thermometer, 200 g of 1,2-dodecanediol [manufactured by Tokyo Chemical Industry Co., Ltd.] and toluene [manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.] were added. ], and 4 g of 97% sulfuric acid [special grade, manufactured by Kishida Chemical Co., Ltd.] were charged, and after purging with nitrogen, the temperature was raised to 90°C, and at the same temperature, the pressure was reduced until the gauge pressure became 2.7 kPa, and dehydration condensation was carried out. The reaction was carried out for 7 hours.
• Intermediate 1 containing a dehydrated condensate of 1,2-dodecanediol.
• Intermediate 1 was sampled, and the structure and content of the dehydrated condensate of 1,2-dodecanediol contained in the sampled Intermediate 1 were measured by NMR and gas chromatography (GC) described below.
• GC gas chromatography
• ⁇ GC measurement conditions Equipment: GC-2014 (manufactured by Shimadzu Corporation) Detector: FID GC capillary column: Ultra2 (inner diameter 0.2 mm, length 25 m, film thickness 0.11 ⁇ m, manufactured by Agilent J&W) Column temperature: 100°C ⁇ 300°C (heating rate: 10°C/min) Sample injection volume: 2 ⁇ L
• ⁇ Manufacture example 6> In a 1 L four-necked flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer, 386 g of Intermediate 1, 77 g of toluene [manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.], and sodium monochloroacetate [Denac] were added. After adding 121.2 g of sodium hydroxide (manufactured by Tosoh Corporation) and purging with nitrogen, the temperature was raised to 50°C, and while stirring, 40.4 g of granular sodium hydroxide (manufactured by Tosoh Corporation) was gradually added over 5 hours. and then aged for 3 hours.
• sodium hydroxide manufactured by Tosoh Corporation
• Powder 2 containing a surfactant is alkyl hydroxy ether acetic acid (salt) (B) containing 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)sodium acetate, 2-(( 2-((2-hydroxydodecyl)oxy)dodecyl)oxy)sodium acetate, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)sodium acetate and 2- It was a powder containing a total of 40% by weight of sodium ((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetate.
• Calibration curve solution 5 1,2-dodecanediol dimer is 0.0004 g/L and the concentration of undecanoic acid is 1.2 g/L and the concentration of undecanoic acid is 0.0006 g/L
• a sample solution was prepared in which the concentration of the calibration curve solution 6 was 1.2 g/L, the concentration of the powder 2 containing a surfactant was 9.0 g/L, and the concentration of undecanoic acid was 1.2 g/L. .
• the sample solution and calibration curve solutions 4 to 6 were analyzed by HPLC, and the peak of the dimer of 1,2-dodecanediol that appeared at the retention time of 9.0 to 9.52 minutes in the obtained HPLC spectrum and the retention time of 12 Based on the peak area ratio of the alkyl hydroxy ether acetic acid (salt) (B) that appears between .5 and 13.0 minutes and the peak of undecanoic acid that appears between 12.1 and 19.6 minutes, it is determined that the sampled surfactant is included. Based on the content of undecanoic acid contained in Powder 2, the content of alkyl hydroxy ether acetic acid (salt) (B) contained in Powder 2 containing a surfactant was calculated.
• ⁇ Manufacture example 7> In a 300 mL beaker, add 100 g of the surfactant-containing powder 2 produced in Production Example 6, 4.3 g of ion exchange water, and 21.8 g of a 35% hydrochloric acid aqueous solution [manufactured by Kishida Chemical Co., Ltd.], and heat to 70°C. The mixture was heated and stirred for 60 minutes to obtain 126 g of surfactant aqueous solution 4.
• Surfactant aqueous solution 4 contains 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetic acid, 2-((2-(( 2-hydroxydodecyl)oxy)dodecyl)oxy)acetic acid, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)acetic acid and 2-((2-(( It was an aqueous solution containing a total of 30% by weight of 1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)acetic acid.
• Aqueous surfactant solution 5 contains triethanolammonium 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)acetate, 2-((2 -((2-hydroxydodecyl)oxy)dodecyl)oxy)triethanolammonium acetate, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)triethanolammonium acetate and 2-((2-((1-hydroxydodecyl-2-yl)oxy)dodecyl)oxy)triethanolammonium acetate at a total of 27.3% by weight.
• ⁇ Manufacture example 9> Add 33.3 g of surfactant aqueous solution 4 produced in Production Example 7 and 1.3 g of potassium hydroxide [manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.] to a 50 mL beaker, heat to 70° C., and stir for 60 minutes. 24.6g of surfactant aqueous solution 6 was obtained.
• Surfactant aqueous solution 6 is 2-((1-((2-hydroxydodecyl)oxy)dodecyl-2-yl)oxy)potassium acetate, 2-((2-((2-hydroxydodecyl)oxy)dodecyl)oxy ) Potassium acetate, 2-((1-((1-hydroxydodecyl-2-yl)oxy)dodecyl-2-yl)oxy)potassium acetate and 2-((2-((1-hydroxydodecyl-2-yl) It was an aqueous solution containing a total of 28.9% by weight of potassium )oxy)dodecyl)oxy)acetate.
• Examples 1 to 5 and Comparative Examples 1 to 3 Powders 1 and 2 containing surfactants obtained in Production Examples 1 and 6 and surfactant aqueous solutions 1 to 6 obtained in Production Examples 2 to 4 and 7 to 9 were mixed in the proportions shown in Table 1. , surfactant compositions 1 to 5 of the present invention and comparative surfactant compositions 1' to 3' were prepared.
• Examples 6 to 14 and Comparative Examples 4 to 5 Surfactant compositions 1 to 5 and comparative surfactant compositions 1' to 3' and any other components described below were mixed in the proportions shown in Tables 2 to 5, and Examples 6 to 14 were prepared.
• a cleaning agent of the present invention shampoo, pump former facial cleanser, and cream facial cleanser
• a comparative cleaning agent shampoo according to Comparative Examples 4 and 5 were prepared.
• the numbers in parentheses in Tables 2 to 5 are values converted to the proportion of the components (sometimes referred to as active ingredients) remaining after water is removed from each raw material.
• ⁇ GC measurement conditions Equipment: GC-1700 (manufactured by Shimadzu Corporation) Column: Zebron ZB-5 (length: 15 m, inner diameter: 0.25 mm, film thickness: 0.25 ⁇ m, manufactured by Shimadzu GLC Co., Ltd.) Vaporization chamber: 310°C Detector: FID (temperature: 320°C) Column temperature: 80°C ⁇ 300°C (heating rate 10°C/min) 300°C (hold for 10 minutes) Total flow rate: 115ml/min Column flow rate: 2.2ml/min Split ratio: 50 Pressure: 100kPa Sample injection volume: 1 ⁇ L
• ⁇ Amount of residual sebum after using pump former facial cleanser and cream facial cleanser> A total of 10 male and female panelists thoroughly wet their faces with 40°C hot water, then washed their faces with 5 g of the cleansing agent of Example 12 (facial cleanser for pump formers), and rinsed with 40°C hot water. After 1 hour, the forehead was wiped at five random locations with a kitchen towel (1 cm x 1 cm) soaked in ethanol. The wiped kitchen towel was immersed in a screw tube containing 1 mL of methanol (screw tube No. 6, manufactured by Maruem Co., Ltd.), shaken by hand for 5 minutes, and the components wiped off with the kitchen towel were extracted into methanol. A sample solution was prepared.
• the cleaning agents of Examples 6 to 14 have less residual sebum and less shine on the skin than the cleaning agents of Comparative Examples 4 and 5, and have a softer feel to the hair and moisturizing properties to the skin. Excellent.
• a cleansing agent using the surfactant composition of the present application is suitable for shampoos, facial cleansers, etc. because it has low residual sebum and shine on the skin, and has excellent softness of the hair and moisturizing properties of the skin. Furthermore, it may be used as a household cleaning agent (clothing detergent, dishwashing detergent, etc.) and an industrial cleaning agent (cleaning agent for metals, precision parts, etc.).

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