WO2012029950A1 - 洗浄剤組成物 - Google Patents

洗浄剤組成物 Download PDF

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Publication number
WO2012029950A1
WO2012029950A1 PCT/JP2011/070043 JP2011070043W WO2012029950A1 WO 2012029950 A1 WO2012029950 A1 WO 2012029950A1 JP 2011070043 W JP2011070043 W JP 2011070043W WO 2012029950 A1 WO2012029950 A1 WO 2012029950A1
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mass
component
components
general formula
alkyl
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English (en)
French (fr)
Japanese (ja)
Inventor
宏樹 武内
正廣 宮木
奈緒子 山本
奈都子 東西田
ユルゲン ベナード
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Kao Corp
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Kao Corp
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Application filed by Kao Corp filed Critical Kao Corp
Priority to EP11821964.1A priority Critical patent/EP2612652B2/en
Priority to CN201180042592.8A priority patent/CN103079533B/zh
Publication of WO2012029950A1 publication Critical patent/WO2012029950A1/ja
Priority to US13/760,096 priority patent/US8703108B2/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • 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
    • C11D1/06—Ether- or thioether 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D17/0047—Detergents in the form of bars or tablets
    • C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar

Definitions

  • the present invention relates to a cleaning composition.
  • Alkyl ether carboxylic acid-based surfactants are known as low-stimulation surfactants for the skin, but they are poor in foaming properties, so we consider using them with other surfactants such as alkyl ether sulfates.
  • other surfactants such as alkyl ether sulfates.
  • a detergent composition with improved foaming ability of an ether carboxylic acid surfactant a detergent composition containing an ether carboxylic acid surfactant having a narrow molecular weight distribution (Patent Document 4, Patent Document 5) or A detergent composition (Patent Document 6) containing an ether carboxylic acid surfactant having an addition molar distribution of specific ethylene oxide has also been proposed.
  • Patent Document 4 Patent Document 5
  • Patent Document 6 A detergent composition containing an ether carboxylic acid surfactant having an addition molar distribution of specific ethylene oxide
  • JP 2007-112984 A Japanese National Patent Publication No. 11-508268 JP 2008-285479 A Japanese Patent Laid-Open No. 61-21199 JP 2001-207189 A Japanese Patent Laid-Open No. 2-175799
  • the present invention is the following general formula (1)
  • R 1 represents an alkyl group having 4 to 22 carbon atoms, n represents a number of 0 to 20, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or organic ammonium
  • An agent composition is provided.
  • the present invention provides a method for rinsing the skin after applying the cleaning composition to the skin part of the body for cleaning.
  • the cleaning composition of the present invention is excellent in foam performance such as foamability, foam amount, foam quality, etc., and has good rinsing properties. Furthermore, the skin cleanser composition has a high sebum detergency, and can reduce back pimples and mottled redness of the skin. Further, after washing, a smooth skin feel can be imparted even under high temperature and high humidity.
  • the present invention relates to a detergent composition having excellent foaming and rinsing properties and high sebum detergency.
  • the present inventors have found that when an alkyl ether carboxylate having a specific distribution is used, a detergent having excellent foam performance, good rinsing properties and feel, and high sebum detergency can be obtained.
  • R 1 is an alkyl group having 4 to 22 carbon atoms, preferably an alkyl group having 10 to 16 carbon atoms, and more preferably an alkyl group having 12 to 14 carbon atoms.
  • the alkyl chain of R 1 may be either a straight chain or a branched chain, but a straight chain alkyl group is preferable from the viewpoint of foamability.
  • R 1 contains two or more alkyl groups, and R 1 has an average carbon number of 10.8 to 12.5, preferably 12.1 to 12.4. If it is in this range, it is excellent in terms of foamability and foam quality, and stability at low temperature, which is preferable.
  • R 1 contains two or more alkyl groups, and the component having the largest alkyl chain length is preferably 55% by mass or more and less than 97% by mass, more preferably 60 to 95% by mass, Further, 70 to 95% by mass is preferable because the amount of foam and foam quality are excellent.
  • n represents a number from 0 to 20, and more preferably from 0 to 12.
  • n represents the number of moles of ethylene oxyoxide added, and the average number of moles added (average value of n) in the composition is preferably 1.5 to 3.5 from the viewpoint of good foaming. 0.7 to 3.4 is more preferable, and 2.8 to 3.1 is more preferable.
  • the components of n ⁇ 6 be 10% by mass or more in total, more preferably 10 to 25% by mass, more preferably 12 to 25% by mass, still more preferably 14 to 25% by mass, and more preferably.
  • the content is 14 to 22% by mass, more preferably 14 to 18% by mass.
  • M represents a hydrogen atom; an alkali metal such as sodium or potassium; an alkaline earth metal such as calcium or magnesium; an ammonium; an ammonium derived from an alkanolamine such as monoethanolamine, diethanolamine or triethanolamine; Can be mentioned.
  • alkali metals are preferable from the viewpoints of foamability, low-temperature stability, and lack of coloration over time.
  • the present invention relates to a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof.
  • R 1 is a compound having 4 to 22 carbon atoms.
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium. By doing in this way, foamability can be accelerated and creamy foam quality can be obtained.
  • the present invention is a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof.
  • R 1 has 10 to 16 carbon atoms.
  • the component having a large alkyl chain length is 55% by mass or more and less than 97% by mass, n represents a number of 0 to 20, and the average value in the composition is 1.5 to 3.5.
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium.
  • the present invention relates to a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof.
  • R 1 is a compound having 4 to 22 carbon atoms.
  • An alkyl group R 1 contains two or more alkyl groups, the average carbon number of R 1 is 10.8 to 12.5, and the component having the largest alkyl chain length is 55
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium.
  • the present invention relates to a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof.
  • R 1 is a compound having 4 to 22 carbon atoms.
  • An alkyl group R 1 contains two or more alkyl groups, the average carbon number of R 1 is 10.8 to 12.5, and the component having the largest alkyl chain length is 55
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium.
  • the present invention is a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof.
  • R 1 has 10 to 16 carbon atoms.
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium.
  • the present invention is a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof, wherein in the general formula (1), R 1 has 12 to 14 carbon atoms.
  • R 1 is an alkyl group
  • R 1 contains two or more alkyl groups
  • R 1 has an average carbon number of 12.1 to 12.4
  • the component having the largest alkyl chain length is 70 N represents a number of 0 to 12
  • the average value in the composition is 2.8 to 3.1
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium.
  • the present invention is a cleaning composition containing an alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof, wherein in the general formula (1), R 1 has 12 to 14 carbon atoms.
  • R 1 is an alkyl group
  • R 1 contains two or more alkyl groups
  • R 1 has an average carbon number of 12.1 to 12.4
  • the component having the largest alkyl chain length is 70 N is a number from 0 to 12
  • the average value in the composition is 2.8 to 3.1
  • M is preferably a hydrogen atom, sodium, potassium, or ammonium.
  • the alkyl ether carboxylic acid represented by the general formula (1) or a salt thereof has the above-described composition, and is contained in an amount of 0.5 to 20% by mass, and further 1 to 15% by mass in the total composition. However, it is preferable from the viewpoints of excellent cleanability, sebum cleanability, and smooth skin feel.
  • the cleaning composition of the present invention can further contain water as a solvent.
  • the water can be contained in the total composition in an amount of preferably 3 to 99% by mass, more preferably 10 to 95% by mass.
  • R 1 represents an alkyl group having 4 to 22 carbon atoms, n represents a number of 0 to 20, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or organic ammonium
  • Detergent composition containing a salt is preferred.
  • R 1 represents an alkyl group having 4 to 22 carbon atoms, n represents a number of 0 to 20, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, ammonium or organic ammonium
  • the cleaning composition of the present invention further comprises components used in ordinary cleaning agents, for example, surfactants other than the general formula (1), moisturizing agents, oily components, bactericides, anti-inflammatory agents, antiseptics, chelates Agents, thickeners, pearling agents, fragrances, cooling agents, pigments, UV absorbers, antioxidants, plant extracts and the like.
  • surfactants other than the general formula (1) for example, surfactants other than the general formula (1), moisturizing agents, oily components, bactericides, anti-inflammatory agents, antiseptics, chelates Agents, thickeners, pearling agents, fragrances, cooling agents, pigments, UV absorbers, antioxidants, plant extracts and the like.
  • the cleaning composition of the present invention is produced by mixing the compounding components by an ordinary method.
  • the resulting cleaning composition may be either liquid or solid, but when it is liquid, the viscosity when measured with a B-type viscometer (manufactured by Tokyo Keiki Co., Ltd.) at 25 ° C. is 200 to 80,000 mPa ⁇ s. It is preferable that it can be adjusted by appropriately selecting the blending components.
  • the pH is preferably 3 to 12, more preferably 5 to 10.5.
  • the measurement of pH is a value obtained by diluting each cleaning composition 20 times with ion-exchanged water at 25 ° C.
  • the cleaning composition of the present invention can be, for example, a facial cleanser, body soap, hand soap, hair cleaning agent, and the like. Among them, it is suitable as a skin cleanser composition such as a facial cleanser and body soap.
  • the method for cleaning the skin using the cleaning composition of the present invention is, for example, as follows. That is, the cleaning composition of the present invention is a method of applying an appropriate amount to the body, that is, the body skin such as the face, limbs, and torso, washing with foaming, and then rinsing using hot water such as a shower. In addition, an appropriate amount can be applied to cleaning aids such as towels, sponges, brushes, etc., and foamed for cleaning.
  • the alkyl composition, EO addition molar distribution, and ratio of each component of the alkyl ether carboxylic acid were measured by gas chromatography (GC).
  • GC gas chromatography
  • the measurement was performed according to the following analysis method 1 and / or analysis method 2. In any analysis method, an equivalent result can be obtained, but it is preferable to measure by analysis method 2 because it is not easily influenced by other components when analyzing the product.
  • Example pretreatment method To 50 mg of alkyl ether carboxylate, 1.5 mL of ion-exchanged water and 2 mL of diethyl ether were added, and 35% hydrochloric acid was added until the aqueous layer became pH 2 or lower. After stirring with shaking, the upper layer was separated and a diazomethane-ether solution was added until the yellow color did not disappear. Nitrogen gas was blown in to remove diazomethane, and then diluted with diethyl ether and subjected to GC analysis. The diazomethane-ether solution was prepared by the following procedure.
  • a 300 mL distillation flask equipped with a Teflon (registered trademark) cock dropping funnel and a downward condenser was charged with a solution of 24 g of potassium hydroxide in 52 g of water, and 162 mL of carbitol and 48 mL of ether were added.
  • the cooler was cooled with tap water.
  • Two receivers were connected in series and cooled with dry ice-methanol. The second receiver was charged with 30 mL of ether, and the tip of the gas inlet tube was immersed under the ether surface.
  • the flask was heated to 70 ° C.
  • Example pretreatment method 150 mg of alkyl ether carboxylate was dissolved in 50 mL of methanol. Moreover, about the cleaning composition, it extract
  • a strong anionic surfactant such as polyoxyethylene alkyl ether sulfate
  • the diazomethane-ether solution was prepared by the following procedure using a diazomethane generator (GM-50, manufactured by Miyamoto Riken Kogyo).
  • the first and second receptacles, and the second and third receptacles are connected with a silicone rubber stopper and a Teflon (registered trademark) tube.
  • a silicone rubber stopper and a Teflon (registered trademark) tube.
  • 0.8 g of N-methyl-N′-nitro-N-nitrosoguanidine was collected and 2.5 mL of ion exchange water was added.
  • a third receiver 10 mL of t-butyl methyl ether was collected.
  • the first, second and third receivers were ice-cooled.
  • a plastic syringe was attached to the second receiver, and 3 mL of a solution in which 20 g of sodium hydroxide was dissolved in 100 mL of ion-exchanged water was placed in this syringe.
  • This sodium hydroxide aqueous solution is slowly dropped to produce diazomethane gas, and nitrogen gas is gently blown from the first receiver side, dissolved in t-butyl methyl ether of the third receiver, and diazomethane-ether A solution was obtained.
  • the following reagents were used in the sample pretreatment.
  • Methanol manufactured by Kanto Chemical, for high performance liquid chromatography, 25183-1B
  • Formic acid manufactured by Wako Pure Chemical Industries, reagent special grade, 066-00461
  • Chloroform manufactured by Kanto Chemical, deer grade 1, 07278-01
  • N-methyl-N'-nitro-N-nitrosoguanidine manufactured by Kanto Chemical, deer grade 1, 25596-51
  • t-Butyl methyl ether manufactured by Kanto Chemical, deer special grade, 04418-00
  • Sodium hydroxide (Wako Pure Chemical Industries, special grade, 196-13761)
  • the alkyl ether carboxylate used in the cleaning composition of the present invention can be produced, for example, as follows. Unless otherwise indicated, “%” indicates mass%.
  • average carbon number is 12.1
  • the total amount of n ⁇ 6 components is It was 12.5% by mass.
  • the average number of carbons is 12.3
  • the average value of n is 3.1
  • n ⁇ 6 The total amount of the components was 18% by mass.
  • the average number of carbons is 12.3
  • N ⁇ 6 was 21.6% by mass.
  • Production Example 3 Following Production Example 1, EO was reacted with decyl alcohol as a raw material to obtain an alkyl ethoxylate having 3.55 moles of EO added. This was subjected to an oxidation reaction as in Example 1, and the resulting alkyl ether carboxylate was treated with hydrochloric acid to obtain an alkyl ether carboxylic acid.
  • M H
  • R 1 is a decyl group
  • n has an average value of 3.1
  • n 0 contains 16% by mass.
  • Production Example 4 Following Production Example 1, EO was reacted with lauryl alcohol as a raw material to obtain an alkyl ethoxylate having 3.55 moles of EO added. This was subjected to an oxidation reaction as in Example 1, and the resulting alkyl ether carboxylate was treated with hydrochloric acid to obtain an alkyl ether carboxylic acid.
  • M H
  • R 1 is a lauryl group
  • n has an average value of 3.1
  • n 0 contains 16% by mass.
  • Production Example 5 According to Production Example 1, EO was reacted with myristyl alcohol as a raw material to obtain an alkyl ethoxylate having 3.55 moles of EO added. This was subjected to an oxidation reaction as in Example 1, and the resulting alkyl ether carboxylate was treated with hydrochloric acid to obtain an alkyl ether carboxylic acid.
  • M H
  • R 1 is a myristyl group
  • n has an average value of 3.1
  • n 0 contains 16% by mass
  • the total amount of the components of n ⁇ 6 was 18% by mass.
  • Production Example 6 Following Production Example 1, EO was added to a raw material in which lauryl alcohol and cetyl alcohol were mixed at a mass ratio of 20/80 to obtain an alkyl ethoxylate having 3.55 moles of EO added. This was subjected to an oxidation reaction as in Example 1, and the resulting alkyl ether carboxylate was treated with hydrochloric acid to obtain an alkyl ether carboxylic acid.
  • M H
  • average value of n 3.1
  • n 0
  • the total amount of the components of n ⁇ 6 was 18% by mass.
  • Production Example 9 In the same manner as in Production Example 1, an EO adduct of alcohol (produced AE) was obtained. An oxidation reaction was performed in the same manner as in Production Example 1 except that the reaction temperature was 75 ° C. and the reaction time was 4 hours. As a result, the reaction rate was 98%. Furthermore, the alkyl ether carboxylate obtained was treated with hydrochloric acid to obtain an alkyl ether carboxylic acid. This is EC9.
  • M H
  • average carbon number 12.1
  • the average value of n 2.9
  • 11% by mass of n 0 components
  • the total amount of n ⁇ 6 components was 12% by mass.
  • M H
  • average carbon number 12.1
  • Production Example 11 A stainless steel autoclave equipped with stirring and temperature control was charged with 1196 g (6.42 mol) of lauryl alcohol [trade name: Calcoal 2098, manufactured by Kao] and 2.6 g (0.0478 mol) of potassium hydroxide, and dehydrated under reduced pressure. Went. Subsequently, 846 g (19.2 mol) of ethylene oxide (EO) was introduced at 155 ° C., and the reaction was carried out at a reaction temperature of 155 ° C. and a reaction pressure of 0.4 MPa for 2 hours. After completion of the reaction, the mixture was cooled and stirred at 80 ° C.
  • lauryl alcohol trade name: Calcoal 2098, manufactured by Kao
  • EO ethylene oxide
  • Examples 1 to 11 and Comparative Examples 1 to 9 Using the compounds having the composition shown in Table 1, skin cleansing agents were produced, and foaming properties, foam amount, foam quality and rinsing properties were evaluated. Further, the appearance (low temperature stability) of the skin cleanser at 5 ° C. was visually evaluated. The results are also shown in Table 1.
  • Sebum residual rate A circle with a diameter of 3.5 cm is marked on the inner side of the forearm as a test site.
  • 2% by mass of carbon black is dispersed in model comedo sebum shown in Table 2, and this is dissolved in a 50 ° C. hot water bath, and 20 ⁇ L of that is uniformly applied to the test site.
  • Comparative evaluation of Examples 19 and 20 and Comparative Example 16 (commercial product of soap formulation): A body cleanser having the composition shown in Table 4 was produced by the following method, and the back pimple alleviation effect by daily use was evaluated.
  • the soap prescription commercial product used as Comparative Example 16 is Dove Beauty Moisture Body Wash (manufactured by Unilever Japan), water, myristic acid, lauric acid, hydroxylated K, palmitic acid, sodium laureth sulfate, glycerin, distearin.
  • Example 19 adjusts prescription so that it may become the foam amount substantially the same at the time of use with the soap prescription commercial item of the comparative example 16 used for the comparison.
  • Examples 21-24 A skin cleanser having the composition shown in Table 5 was produced by a conventional method, and foam performance, rinsing properties and skin feel were evaluated. All had good foaming properties, foam amount, foam quality and rinsing properties, excellent sebum cleaning properties, and no stickiness of the skin after towel drying. Moreover, it was felt that a smooth feeling was strong even in skin feel under high temperature and high humidity conditions.

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PCT/JP2011/070043 2010-09-03 2011-09-02 洗浄剤組成物 Ceased WO2012029950A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP11821964.1A EP2612652B2 (en) 2010-09-03 2011-09-02 Cleansing composition
CN201180042592.8A CN103079533B (zh) 2010-09-03 2011-09-02 清洁剂组合物
US13/760,096 US8703108B2 (en) 2010-09-03 2013-02-06 Cleansing composition

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JP2010-197494 2010-09-03
JP2010197494 2010-09-03

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EP (1) EP2612652B2 (https=)
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CN (1) CN103079533B (https=)
DE (1) DE202011110950U1 (https=)
MY (1) MY156831A (https=)
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Cited By (6)

* Cited by examiner, † Cited by third party
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WO2013031898A1 (ja) * 2011-09-02 2013-03-07 花王株式会社 皮膚洗浄剤組成物
WO2013031899A1 (ja) * 2011-09-02 2013-03-07 花王株式会社 皮膚洗浄剤組成物
WO2013085035A1 (ja) * 2011-12-08 2013-06-13 花王株式会社 皮膚洗浄剤組成物
JP2014091815A (ja) * 2012-11-06 2014-05-19 Kao Corp 洗浄剤組成物
JP2015113314A (ja) * 2013-12-13 2015-06-22 花王株式会社 皮膚洗浄剤組成物
EP2821054A4 (en) * 2012-03-02 2015-09-16 Kao Corp CLEANSING COMPOSITION FOR THE SKIN

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Publication number Priority date Publication date Assignee Title
JP5856756B2 (ja) 2011-05-02 2016-02-10 花王株式会社 皮膚洗浄剤組成物
BR112018006212B1 (pt) * 2015-10-01 2022-04-12 Unilever Ip Holdings B.V. Composição de detergente em pó formada por carbonato sem fosfato e método de tratamento doméstico de um tecido
JP2017149952A (ja) * 2017-02-28 2017-08-31 花王株式会社 洗浄剤組成物
EP3556344B1 (en) 2018-04-16 2025-04-16 Kao Corporation, S.A. Cosmetic compositions
EP4215518A1 (en) 2022-01-24 2023-07-26 KAO CHEMICALS GmbH Process for preparing amidated fatty acids and derivatives thereof

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