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WO2017179627A1 - Composition de produit de nettoyage et procédé pour le produire - Google Patents

Composition de produit de nettoyage et procédé pour le produire Download PDF

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Publication number
WO2017179627A1
WO2017179627A1 PCT/JP2017/015010 JP2017015010W WO2017179627A1 WO 2017179627 A1 WO2017179627 A1 WO 2017179627A1 JP 2017015010 W JP2017015010 W JP 2017015010W WO 2017179627 A1 WO2017179627 A1 WO 2017179627A1
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WO
WIPO (PCT)
Prior art keywords
acid
component
mass
amino acid
organic layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2017/015010
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English (en)
Japanese (ja)
Inventor
清水　克也
関口　範夫
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asahi Kasei Finechem Co Ltd
Original Assignee
Asahi Kasei Finechem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Asahi Kasei Finechem Co Ltd filed Critical Asahi Kasei Finechem Co Ltd
Priority to CN201780022993.4A priority Critical patent/CN109072128B/zh
Priority to JP2018512051A priority patent/JP6653751B2/ja
Priority to KR1020187023028A priority patent/KR102051789B1/ko
Publication of WO2017179627A1 publication Critical patent/WO2017179627A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/22—Gas releasing
    • A61K2800/222—Effervescent

Definitions

  • the present invention relates to a cleaning composition and a method for producing the same.
  • Patent Document 1 discloses a technique for improving the odor and turbidity of acylamino acid surfactants.
  • Patent Document 2 discloses a technique for improving the foaming power and feeling of use of an acylamino acid surfactant.
  • an object of the present invention is to provide a cleaning composition having excellent initial foaming power and excellent foaming sustainability (hereinafter also referred to as “foaming sustainability”).
  • the present inventors have found that N-acyl acidic amino acids having a predetermined structure and / or salts thereof, and fatty acid t-butyl esters having a predetermined structure are contained.
  • the agent composition it was found that the foaming power was excellent in initial foaming ability and the foaming durability was excellent, and the present invention was completed.
  • a cleaning composition comprising the following component (A) and the following component (B).
  • R 1 represents an alkyl group having 7 to 23 carbon atoms.
  • M 1 and M 2 each independently represents a hydrogen atom, an alkali metal or an alkaline earth metal, an organic or inorganic ammonium, a basic amino acid, Or choline.
  • Component (B) fatty acid t-butyl ester represented by the following general formula (3) (Wherein R1 represents an alkyl group having 7 to 23 carbon atoms).
  • R1 represents an alkyl group having 7 to 23 carbon atoms.
  • the following component (C) is further included, The content of the component (C) as a free fatty acid is in the range of 0.1% by mass to 5% by mass with respect to the mass of the component (A), according to [1] or [2].
  • Cleaning composition is provided.
  • R 1 represents an alkyl group having 7 to 23 carbon atoms.
  • M 3 represents a hydrogen atom, an alkali metal or an alkaline earth metal, organic or inorganic ammonium, a basic amino acid, or choline.
  • the cleaning composition according to any one of [1] to [3], further comprising the following component (D) and / or the following component (E): (D): Aliphatic amidopropyl betaine and / or alkyl betaine (E): Nonionic surfactant [5]
  • the manufacturing method of a cleaning composition including the following processes.
  • the present embodiment a mode for carrying out the present invention (hereinafter simply referred to as “the present embodiment”) will be described in detail.
  • the following embodiments are examples for explaining the present invention, and are not intended to limit the present invention to the following contents.
  • the present invention can be appropriately modified within the scope of the gist.
  • the cleaning composition of the present embodiment comprises the following component (A) (hereinafter also simply referred to as “component (A)” or “(A)”) and the following component (B) (hereinafter simply referred to as “component (B)”. ) ", Also referred to as” (B) ”): Component (A): N-acyl acidic amino acid and / or salt thereof represented by the following general formula (1) and / or (2) In the formulas (1) and (2), R1 represents an alkyl group having 7 to 23 carbon atoms. M 1 and M 2 each independently represent a hydrogen atom, an alkali metal or an alkaline earth metal, organic or inorganic ammonium, a basic amino acid, or choline. M 1 and M 2 may be the same or different. Component (B): fatty acid t-butyl ester represented by the following general formula (3).
  • component (A) N-acyl acidic amino acid (salt)
  • the component (A) in the present embodiment refers to an N-acyl acidic amino acid represented by the following general formula (1) and / or (2) and / or a salt thereof (hereinafter also referred to as “N-acyl acidic amino acid (salt) ) ").
  • R1 represents an alkyl group having 7 to 23 carbon atoms.
  • M 1 and M 2 each independently represent a hydrogen atom, alkali metal or alkaline earth metal, organic or inorganic ammonium, basic amino acid, or choline, and M 1 and M 2 may be the same , May be different.
  • N-acyl acidic amino acid represented by the formula (1) and / or a salt thereof (hereinafter also referred to as “acyl aspartic acid (salt)”) is not particularly limited, but from the viewpoint of performance and availability, N-lauroyl aspartic acid (R1: carbon number 11), N-myristoyl aspartic acid (R1: carbon number 13), and N-palmitoyl aspartic acid (R1: carbon number 15) are preferred. More preferred are N-lauroyl aspartic acid and N-myristoyl yl aspartic acid.
  • acyl aspartate For example, Metal salts, such as sodium salt, potassium salt, lithium salt, magnesium salt, calcium salt; Ammonium salt, such as ammonium salt and alkylammonium salt; Monoethanolamine salt And amine salts such as diethanolamine salt, triethanolamine salt and aminomethylpropanol salt; basic amino acid salts such as lysine salt and arginine salt; From the viewpoint of performance and availability, sodium salts, potassium salts, and triethanolamine salts are preferable, and triethanolamine salts are more preferable.
  • Metal salts such as sodium salt, potassium salt, lithium salt, magnesium salt, calcium salt
  • Ammonium salt such as ammonium salt and alkylammonium salt
  • Monoethanolamine salt And amine salts such as diethanolamine salt, triethanolamine salt and aminomethylpropanol salt
  • basic amino acid salts such as lysine salt and arginine salt
  • sodium salts, potassium salts, and triethanolamine salts are preferable, and triethanolamine salts are more
  • N-acyl aspartic acid and N-acyl aspartate may be used in combination. Further, instead of blending the salt, N-acyl aspartic acid and a base can be blended to form a salt in the blending recipe.
  • the N-acyl acidic amino acid represented by the formula (2) and / or a salt thereof (hereinafter also referred to as “acyl glutamic acid (salt)”) is not particularly limited, but from the viewpoint of performance and availability, N -Lauroyl glutamic acid (R1: carbon number 11), N-myristoyl glutamic acid (R1: carbon number 13), N-palmitoyl glutamic acid (R1: carbon number 15), and N-coconut oil fatty acid acyl glutamic acid (R1: carbon number 8) To 18) are preferred. More preferred are N-lauroyl glutamic acid and N-coconut fatty acid acyl glutamic acid.
  • acyl glutamate Although it does not specifically limit as a salt of acyl glutamate,
  • metal salts such as sodium salt, potassium salt, lithium salt, magnesium salt, calcium salt
  • Ammonium salt such as ammonium salt and alkylammonium salt
  • Monoethanolamine salt examples thereof include amine salts such as diethanolamine salt, triethanolamine salt and aminomethylpropanol salt; basic amino acid salts such as lysine salt and arginine salt, and single substances or mixtures such as choline salt. From the viewpoint of performance and availability, sodium salts, potassium salts, and triethanolamine salts are preferable, and triethanolamine salts are more preferable.
  • the acyl glutamic acid (salt) represented by the formula (2) may be a combination of N-acyl glutamic acid and N-acyl glutamate. Further, instead of blending the salt, N-acylglutamic acid and a base can be blended to form a salt in the blending recipe.
  • Component (A) is not particularly limited, but acylaspartic acid sodium salt, acylaspartic acid potassium salt, acylaspartic acid triethanolamine salt, acylglutamic acid sodium salt, acylglutamic acid potassium salt, and acylglutamic acid triethanolamine salt preferable. More preferred are acylaspartic acid triethanolamine salt and acylglutamic acid triethanolamine salt, and still more preferred is acylaspartic acid triethanolamine salt.
  • N-acyl acidic amino acid and / or salt thereof which is component (A) of the present embodiment, can be produced by a known method described in WO00 / 40546 and the like, and is preferably produced by the method described later. .
  • a component (A) is not restrict
  • Component (B) Fatty acid t-butyl ester
  • the component (B) in this embodiment is a fatty acid t-butyl ester represented by the following general formula (3).
  • R1 represents an alkyl group having 7 to 23 carbon atoms.
  • the fatty acid t-butyl ester represented by the formula (3) is not particularly limited, but from the viewpoint of performance and availability, capric acid t-butyl ester, decanoic acid t-butyl ester, lauric acid t-butyl ester And myristic acid t-butyl ester is preferred. More preferred is lauric acid t-butyl ester.
  • the method for producing the fatty acid t-butyl ester of the formula (3) is not limited, and may be synthesized using a known method.
  • a method of reacting fatty acid chloride with t-butanol, or using a condensing agent such as 4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride A method of condensing with t-butanol can be mentioned, and a method using a condensing agent is preferable because of its high yield.
  • content in particular of a component (B) is not restrict
  • the content is 1000 ppm by mass or less, the foam quality as the cleaning composition is changed, and more elastic elasticity is given to the foam.
  • Content as a free fatty acid of the component (C) represented by Formula (4) is 0.1 mass% or more and 5 mass with respect to the mass of a component (A) from a viewpoint of maintaining the outstanding foamability.
  • the cleaning composition of the present embodiment comprises the following component (D) (hereinafter also simply referred to as “component (D)” and “(D)”) and / or the following component (E) (hereinafter simply referred to as “component”). (E) “, also referred to as” (E) ").
  • component (D) Aliphatic amidopropyl betaine and / or alkyl betaine
  • component (E) Nonionic surfactant.
  • Component (D): Betaines The component (D) of this embodiment is a fatty acid amidopropyl betaine and / or an alkyl betaine betaine.
  • the fatty acid amidopropyl betaine is not particularly limited, and examples thereof include lauramidopropyl betaine, myristamidopropyl betaine, stearamidopropyl betaine, oleylamidopropyl betaine, and cocamidopropyl betaine. Among these, lauramidopropyl betaine and cocamidopropyl betaine are preferable, and lauramidopropyl betaine is more preferable.
  • the alkyl betaine is not particularly limited, and examples thereof include lauryl betaine, myristyl betaine, palmityl betaine, stearyl betaine, oleyl betaine, and coco betaine. Among these, coco betaine and lauryl betaine are preferable, and coco betaine is more preferable.
  • the mass ratio ((A) / (D) of the component (D) with respect to a component (A). ) Is preferably 0.1 or more and 3.0 or less, more preferably 0.2 or more and 2.0 or less.
  • Polyoxyethylene alkyl ethers such as behenyl ether and POE octyl (2-ethyl-hexyl) ether; polyoxyethylenes such as POE / POP (polyoxypropylene) butyl ether, POE / POE lauryl ether, POE / POP cetyl ether POE / POP glycol, etc.
  • Glyceryl fatty acid esters such as glyceryl monostearate, glyceryl monostearate, glyceryl monohydroxystearate, glyceryl distearate; diglyceryl monostearate, diglyceryl monooleate, diglyceryl dioleate, monoisostearate
  • fatty acid alkanolamides are preferable, and coconut oil fatty acid monoethanolamide, coconut oil fatty acid diethanolamide, lauroyl monoethanolamide, lauroyl diethanolamide, and lauroyl isopropanolamide are more preferable.
  • the mass ratio (E) with respect to the sum total of a component (A) and a component (D) is preferably 0.1 or more and 1.0 or less, more preferably 0.1 or more and 0.8 or less.
  • the pH of the cleaning composition of the present embodiment is not particularly limited, but is preferably 4.0 to 8.0. More preferably, it is 4.5 to 7.5, and still more preferably 5.0 to 7.0.
  • the cleaning composition of the present embodiment can further contain an anionic surfactant.
  • the anionic surfactant is not particularly limited. For example, sodium lauryl sulfate, potassium lauryl sulfate, sodium myristyl sulfate, potassium myristyl sulfate, sodium cetyl sulfate, sodium stearyl sulfate, sodium oleyl sulfate, triethanolamine lauryl sulfate, etc.
  • ⁇ -olefin sulfonic acid such as sodium dodecene sulfonate, sodium tetradecene sulfonate, potassium dodecene sulfonate, potassium detradecene sulfonate and the like; ⁇ -sulfolauric acid methyl ester, ⁇ -sulfomyristic acid ⁇ -sulfo fatty acid esters and salts thereof such as methyl ester, ⁇ -sulfolauric acid (EO) n methyl ester; coconut oil fatty acid acyl-N methyl taurine potassium, lauroyl-N methyl taurine sodium, lauroyl-N methyl taurine potassium, lauroyl -N-methyl taurine triethanolamine, myristoyl-N-methyl taurine sodium, myristoyl-N-methyl taurine triethanolamine, coconut oil fatty acid acyl-N-methyl taurine sodium, coconut oil fatty acid acyl-N-me
  • alkylphosphoric acid and its salts such as sodium lauryl phosphate, sodium myristyl phosphate, sodium palm fatty acid phosphate, potassium myristyl phosphate, triethanolamine lauryl phosphate, diethanolamine oleyl phosphate; sodium N-lauroyl glutamate, N -Sodium myristoyl glutamate, N-coconut oil fatty acid sodium acyl glutamate, potassium N-lauroyl glutamate, potassium N-myristoyl glutamate, potassium N-coconut fatty acid acyl glutamate, triethanolamine N-lauroyl glutamate, triethanolamine N-myristoyl glutamate , N-coconut oil fatty acid acyl glutamate triethanuramine, N-lauroylglycine sodium, N-myristoyl Sintriethanolamine, N-lauroyl- ⁇ -alanine potassium, N-lauroylthreonine triethanolamine, N-lauroyls
  • Acyl iminodiacetic acid and its salts sodium polyoxyethylene lauryl ether acetate, potassium polyoxyethylene myristyl ether acetate, polyoxyethylene palmityl ether acetate trieta Ether carboxylic acids and salts thereof such as uramine, sodium polyoxyethylene stearyl ether acetate, sodium polyglyceryl lauryl ether acetate; acylated peptides such as coconut oil fatty acid silk peptide; sodium polyoxyethylene lauric acid amide ether carboxylate, polyoxyethylene myristine Examples include amide ether carboxylic acids and salts thereof such as sodium acid amide ether carboxylate and polyoxyethylene coconut oil fatty acid amide ether carboxylic acid triethanolamine; acyl lactates; alkenyl succinic acids and salts thereof.
  • the cleaning composition of the present embodiment can further contain a cationic surfactant.
  • a cationic surfactant for example, lauryltrimethylammonium chloride, myristyltrimethylammonium chloride, palmityltrimethylammonium chloride, stearyltrimethylammonium chloride, oleyltrimethylammonium chloride, cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, Monoalkyl quaternary ammonium salts such as coconut oil alkyltrimethylammonium chloride, beef tallow alkyltrimethylammonium chloride, stearyltrimethylammonium bromide, coconut oil alkyltrimethylammonium bromide, cetyltrimethylammonium methylsulfuric acid; dioctyldimethylammonium chloride, dilauryl di Dialkyl quaternary ammonium salts such as tilammonium chloride and diste
  • the cleaning composition of the present embodiment may further contain a cationized polymer as long as the effect is not impaired.
  • the cationized polymer is not particularly limited.
  • O- [2-hydroxy-3- (trimethylammonio) propyl] hydroxyethyl cellulose chloride (manufactured by Lion Corporation, trade name, Leoguard LP, manufactured by Union Carbide Corporation) Trade name, polymer JR-400, manufactured by Toho Chemical Co., Ltd., trade name, Katchinal LC-100, LC-200, HC-100, HC-200, etc.), O- [2-hydroxy-3- (lauryldimethylammonio) chloride ) Propyl] hydroxyethylcellulose (trade name, polymer LM-200, etc., manufactured by Union Carbide), cationic cellulose such as hydroxyethylcellulose dimethyldiallylammonium chloride, O- [2-hydroxy-3- (trimethylammonio) chloride ) Propyl] Guam gum (
  • the cationized polymer is preferably a cationized vinyl-based or cationized acrylic polymer, a cationized polysaccharide, or a cationized guar gum, and more preferably a cationized vinyl-based or acrylic polymer.
  • the cleaning composition of the present embodiment further contains gemini compounds such as phosphorylcholines, bispyridinium quaternary ammonium salts, double-chain biscarboxylates, and dilauroylglutamate lysine Na as long as the effects are not impaired. May be.
  • gemini compounds such as phosphorylcholines, bispyridinium quaternary ammonium salts, double-chain biscarboxylates, and dilauroylglutamate lysine Na as long as the effects are not impaired. May be.
  • the cleaning composition of the present embodiment can appropriately contain various components that are usually used as cleaning agents or cosmetics depending on the purpose, as long as the effect is not impaired.
  • these components include powder components such as calcium carbonate, talc, mica, kaolin, titanium dioxide, and zinc dioxide; jojoba oil, macadamia nut oil, avocado oil, evening primrose oil, mink oil, rapeseed oil, sunflower oil, sunflower oil , Corn oil, cacao oil, coconut oil, rice bran oil, olive oil, almond oil, sesame oil, safflower oil, soybean oil, coconut oil, persic oil, castor oil, mink oil, cottonseed oil, owl, palm oil, palm kernel oil, egg yolk
  • Natural animal and vegetable oils and fats such as oil, lanolin and squalene; synthetic triglycerides; hydrocarbons such as squalane, liquid paraffin, petrolatum, ceresin, microcrystalline wax and isoparaffin; carnauba wax, paraffin wax, whale wax, beeswax, chiyandelilla wax, lanolin Waxes Higher alcohols such as cetanol, stearyl alcohol, lau
  • ascorbic acid and its derivatives such as arbutin, kojic acid, magnesium ascorbate phosphate, glutathione, licorice extract, clove extract, tea extract, astaxanthin, cow placenta extract, tocopherol and its derivatives, tranexamic acid and its salts, azulene Whitening ingredients such as ⁇ -hydroxybutyric acid; polyhydric alcohols such as maltitol, sorbitol, glycerin, propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycol, etc., organic compounds such as pyrrolidone carboxylate soda, lactate soda, and citrate soda Acids and salts thereof, hyaluronic acid and salts thereof such as sodium hyaluronate, hydrolysates of yeast and yeast extract, fermentation metabolites such as yeast culture solution and lactic acid bacteria culture solution, collagen, elastin, keratin, sericin White, collagen hydrolyzate, casein hydro
  • Polysaccharides such as saccharides, crystalline cellulose, amorphous cellulose, xylan, mannan, galactan, arabinan, arabinoxylan and their derivatives, glycosaminoglycans such as water-soluble chitin, chitosan, pectin, chondroitin sulfate and salts thereof, and the like Salt, glycine, serine, threonine, alanine, aspartic acid, tyrosine, valine, leucine, arginine, glutamine, prophosphoric acid, etc., sugar amino acid compounds such as aminocarbonyl reactant, plant extracts such as aloe, maronier, trimethi Moisturizers for nucleic acid-related substances such as luglycine, urea, uric acid, ammonia, lecithin, lanolin, squalane, squalene, glucosamine, creatinine, DNA, RNA; carboxymethylcellulose,
  • organic solvents such as ethanol, propylene glycol and 1,3-butylene glycol, antioxidants such as butylhydroxytoluene, tocopherol and phytic acid; citric acid, malic acid, tartaric acid, lactic acid, adipic acid, glutamic acid, asparagine Acids, organic acids such as maleic acid; vitamin A and derivatives thereof; vitamin Bs such as vitamin B6 hydrochloride, vitamin B6 tripalmitate, vitamin B6 dioctanoate, vitamin B2 and derivatives thereof; ascorbic acid, ascorbic acid sulfate, ascorbine Vitamin C such as acid phosphate ester, Vitamin E such as ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, vitamins such as vitamin D, vitamin H, pantothenic acid; nicotinamide, benzyl nicotinate, ⁇ -oryzano , Allantoin, glycyrrhizic acid (
  • astringents such as zinc oxide, zinc sulfate, allantoin hydroxyaluminum, aluminum chloride, zinc sulfocolate and tannic acid; refreshing agents such as menthol and camphor; antihistamines; tocopherols, BHA, BHT, gallic acid, NDGA, ubiquinone
  • Various drugs such as antioxidants such as Saccharomyces yeast, filamentous fungi, bacteria, cow placenta, human placenta, human umbilical cord, yeast, cow collagen, milk-derived protein, wheat, soybean, cow blood, pig blood, chicken crown, Chamomile, cucumber, rice, shea butter, birch, tea, tomato, garlic, clam, rose, loofah, hop, peach, apricot, lemon, kiwi, dodami, capsicum, clara, scallop, kohone, sage, sawtooth grass, mallow Senkyu, assembly, thyme, toki, tow ,
  • a powder component is effective because it increases the cleaning power by the physical friction effect and tends to adsorb dirt on the particle surface.
  • oily component has an effect of solubilizing oily dirt due to the solvent effect of the oily component, and thus is suitable for improving detergency.
  • oily components it is particularly effective to further contain silicones in order to give a refreshing feel after use.
  • further containing a moisturizing agent can suppress rough skin due to excessive degreasing, and tends to contribute to an improvement in the feeling of use.
  • the combined use with a sequestering agent and an antioxidant is effective in suppressing changes in the product under long-term or harsh use conditions and continuing to provide a good feeling of use.
  • the cleaning composition of the present embodiment is not particularly limited, but is suitable for cosmetic applications such as hair shampoo, body soap, cleansing foam, cleansing oil, cleansing cream, cleansing lotion, cleansing milk, toothpaste and the like.
  • the cleaning composition of the present embodiment includes kitchen sinks, tableware, baths, tables, desks, furniture, stationery and other daily necessities, clothing, ornaments, watches, bags, shoes and other personal items, copying machines, Office supplies such as printers, rain gear such as umbrellas and gowns, bicycles, motorcycles, aircraft, ships and other spacecrafts, rockets, satellites and other space engineering equipment, MRI, ultrasonic equipment and other medical equipment, electronic boards, displays, It can be used for various applications such as electronic materials such as solar cells, lithium ion batteries, electrodes, televisions, telephones, mobile phones, smartphones, personal computers and the like.
  • the container of the cleaning composition of this embodiment is not particularly limited, for example, a general-purpose container such as a tube, a pump-type bottle, or a cream jar can be adopted.
  • the manufacturing method of the cleaning composition of this embodiment includes the following processes. (1) First step of obtaining a reaction solution by subjecting an acidic amino acid and a fatty acid chloride to a condensation reaction in a mixed solvent consisting essentially of water and t-butanol in the presence of an alkaline compound for 5.0 to 60 hours. Hereinafter also referred to as “acylation reaction step”.) (2) Second step of obtaining an organic layer containing an N-acyl acidic amino acid by adjusting the obtained reaction solution to pH 1 to 6 with an acid and separating the layer into an organic layer and an aqueous layer at a temperature of 35 to 80 ° C.
  • the obtained organic layer was mixed with water and / or t-butanol and separated into an aqueous layer and an organic layer containing an N-acyl acidic amino acid at a temperature of 35 to 80 ° C. to remove impurities.
  • Third step of obtaining an organic layer containing an N-acyl acidic amino acid (hereinafter also referred to as “water washing step”) (4) From the obtained organic layer, neutralize more than 1/20 of the carboxyl group amount of the N-acyl acidic amino acid, and add organic water at the time of distillation under the condition that the temperature of the organic layer is 90 ° C. or less.
  • the fourth step (hereinafter referred to as “solvent distillation step”) in which the organic solvent is distilled off while maintaining the solid content concentration in the layer at 5.0 to 50% by weight with respect to the total amount of the organic layer (100% by weight). Also called.)
  • the acylation reaction step of the present embodiment is a step in which an acidic amino acid and a fatty acid chloride are subjected to a condensation reaction in a mixed solvent of water and t-butanol in the presence of an alkaline compound.
  • the condensation reaction (acylation reaction) Produces a crude N-acyl acidic amino acid.
  • a reaction solution obtained by the condensation reaction is also referred to as an “acylation reaction solution”.
  • the time of the acylation reaction step means that an acid is added for the next acid precipitation step from the time when three of the acidic amino acid, fatty acid chloride, and alkaline compound start to coexist in the solvent. It means the time to the point of starting.
  • the time of the acylation reaction step is 5.0 hours or longer.
  • fatty acid t-butyl ester is substantially produced.
  • the time of the acylation reaction process is 60 hours or less, the once-generated fatty acid t-butyl ester is prevented from being decomposed, and the resulting detergent composition substantially eliminates the fatty acid t-butyl ester.
  • the time for the acylation reaction step is preferably 10 to 40 hours.
  • the molar ratio of fatty acid chloride to acidic amino acid is preferably 1.05 or less, more preferably 1.0 or less, and further preferably 0.98 or less. It exists in the tendency which is easy to reduce the production amount of a free fatty acid because the molar ratio of the fatty acid halide with respect to an acidic amino acid is 1.05 or less.
  • the volume ratio of water to t-butanol is preferably in the range of 90/10 to 20/80, more preferably 85/15. It is in the range of 50/50.
  • the ratio is in the range of 90/10 to 20/80, the acidic amino acid, the fatty acid chloride, and the alkaline compound are easily compatible with each other, and the reaction rate can be increased.
  • the concentration of acidic amino acid in the acylation reaction step is not particularly limited, but the viscosity of the reaction solution increases over time during the reaction, so the concentration is adjusted to a concentration that allows stirring and mixing when the reaction is close to completion. It is preferable to do.
  • the reaction temperature in the acylation reaction step is not particularly limited, but is preferably in the range of ⁇ 10 to 70 ° C., more preferably in the range of ⁇ 10 to 20 ° C., from the viewpoint of promoting the main reaction and suppressing the side reaction.
  • the range is preferably -5.0 to 10 ° C.
  • the alkaline compound used in the acylation reaction step is not particularly limited, and examples thereof include inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and barium hydroxide.
  • the pH in the acylation reaction step is preferably maintained in the range of 9 to 13.5, more preferably in the range of 10 to 13 from the viewpoints of promoting the main reaction and suppressing the side reaction.
  • the acylation reaction liquid is separated into two layers, an organic layer and an aqueous layer, with an acid such as hydrochloric acid and sulfuric acid (preferably mineral acid) having a pH of 1 to 6, This is a step of obtaining an organic layer.
  • the produced N-acyl acidic amino acid is present in the form of an alkali salt.
  • the dissociation state of the carboxyl group changes, and the layer separation state, that is, the mass ratio between the organic layer and the aqueous layer and the removal of inorganic salts slightly change. More preferably, the pH is 1 to 2.5.
  • the temperature in the acid precipitation step is preferably 35 to 80 ° C. More preferably, it is 40 to 70 ° C.
  • the temperature is 35 ° C. or higher, the time required to reach the layer separation equilibrium can be shortened, and when the equilibrium is reached, the residual amount of the inorganic salt in the organic layer tends to be reduced. Since the boiling point at normal pressure of water / t-butanol azeotropic composition is around 80 ° C, boiling is prevented when it is 80 ° C or less, and no layer separation under pressure is required, thus simplifying the apparatus. This is advantageous from the viewpoint of conversion.
  • the time for the acid precipitation step means the standing time at a predetermined pH and temperature.
  • the standing time is not limited, but it is preferably 0.1 to 10 hours from the viewpoint of sufficiently separating the organic layer and the aqueous layer and suppressing the decomposition of the fatty acid t-butyl ester. More preferably, it is 0.2 to 5.0 hours.
  • the water washing step of the present embodiment is a step of reducing water-soluble impurities in the organic layer obtained in the acid precipitation step by transferring them into the water layer by a liquid-liquid extraction method. Specifically, water and / or t-butanol is added to the organic layer after the acid precipitation step to adjust the composition of N-acyl acidic amino acid / t-butanol / water, and water-liquid extraction in the organic layer is performed by liquid-liquid extraction. The inorganic salt produced in the acidic impurities, mainly in the acylation reaction step and the acid precipitation step, is transferred into the aqueous layer.
  • the washing temperature is preferably 35 to 80 ° C., more preferably 40 to 70 ° C.
  • the time required to reach the layer separation equilibrium is not lengthened, and even if the equilibrium is reached, the inorganic salt does not easily remain in the organic layer. It tends to be divided into layers regardless of the medium concentration.
  • the boiling point of the azeotropic composition of water / t-butanol is in the vicinity of 80 ° C, it is difficult for boiling to occur by setting the washing temperature to 80 ° C or lower, and it is necessary to use a layer separation under pressure or a special device. Tend to be small.
  • the distillation operation is carried out as an N-acyl acidic amino acid salt, but the salt is not particularly limited, and alkali metal salts such as sodium, potassium and lithium, calcium, Examples include alkaline earth metal salts such as magnesium, aluminum salts, zinc salts, ammonium salts, organic amine salts such as monoethanolamine, diethanolamine / triethanolamine and triisopropanolamine, and basic amino acid salts such as arginine and lysine. From the viewpoints of the performance and availability of the cleaning composition, alkali metal salts and triethanolamine salts are preferred.
  • an alkali or an aqueous solution thereof may be added.
  • the N-acyl acidic amino acid salt it is preferably added so that 1/20 or more of the carboxyl group content in the N-acyl acidic amino acid is an alkali salt.
  • the ratio of the alkali salt is 1/20 or more of the carboxyl group content, the effect of alkali addition is sufficiently obtained, and the fluidity of the mixed solution tends to be preferably improved.
  • the ratio of the alkali salt is more preferably added to be 1/10 or more of the carboxyl group content, and more preferably to be 1/3 or more.
  • the temperature in the solvent distillation step is preferably 90 ° C. or lower.
  • the temperature is 90 ° C. or lower, the decomposition reaction of the N-acyl acidic amino acid or its salt is suppressed, and the product quality tends to be kept good. It is more preferably 80 ° C. or lower, and further preferably 70 ° C. or lower.
  • the time in the solvent distillation step is the time from when the solvent starts to distill at a predetermined temperature until t-butanol in the product reaches a predetermined concentration or less and the solvent distillation operation is stopped.
  • the solvent evaporation time is not particularly limited, but is preferably 1.0 to 60 hours from the viewpoint of suppressing foaming of the cleaning composition and suppressing decomposition of fatty acid t-butyl ester. More preferably, it is 5.0 to 40 hours.
  • the solid content concentration in the liquid at the time of distillation is maintained at 5.0 to 50% by mass with respect to the total amount of the liquid (100% by mass). To do.
  • the solid content concentration is 50% by mass or less, viscosity increase and solidification of the liquid can be suppressed, and the occurrence of decomposition reaction of the N-acyl acidic amino acid or its salt due to overheating can be suppressed.
  • the solid content concentration is 5.0% by mass or more, the concentration of t-butanol can be prevented from being excessively reduced and the distillation efficiency can be prevented from being lowered, and further, when adjusting to the solid content concentration necessary for the final product. Concentration may be unnecessary, which is preferable.
  • the solid content concentration is more preferably 20 to 40% by mass, and further preferably 25 to 35% by mass.
  • t-butanol is preferably removed to such an extent that it does not affect the scent of the product.
  • the t-butanol content is preferably 0.1 mass ppm or more and 750 mass ppm or less, more preferably 0.1 mass ppm or more and 300 mass ppm or less with respect to the N-acyl acidic amino acid. More preferably, it is 0.1 mass ppm or more and 150 mass ppm or less.
  • the cleaning composition of the present embodiment preferably maintains a height of 60% or more from the height of the foam at the time of foaming after 5 minutes from the occurrence of foaming under a predetermined condition. More preferably, the height is maintained.
  • a detergent composition comprising at least the component (A) and the component (B), and the detergent composition and component comprising the component (A), the component (B), and the component (C).
  • Cleaning composition comprising component (B), component (C) and component (D), cleaning composition comprising component (A), component (B), component (C) and component (E) It is exhibited in any case of a cleaning composition comprising a product, component (A), component (B), component (C), component (D), and component (E).
  • the cleaning composition of the present embodiment further changes the foam quality as the cleaning composition due to this high foaming sustainability, imparts firm elasticity to the foam, and provides fine foam. It is in.
  • free fatty acid (%) peak area area of fatty acid / peak area area of acylamino acid salt ⁇ 100
  • Examples 1 to 6 and 12 To the N-lauroyl-L-aspartic acid aqueous solution obtained in Comparative Example 1 was mixed lauric acid t-butyl ester so as to have the composition shown in Table 1 to prepare a detergent composition.
  • Table 1 shows the foaming power and foaming sustainability of the obtained cleaning composition. Since Examples 1 to 6 contain fatty acid t-butyl ester, it was at least confirmed that the results of excellent foaming sustainability were obtained as compared with Comparative Example 1 not containing the ester.
  • Example 7 (Acylation step) To a mixed solution of 1444 g (7.72 mol) of monosodium L-glutamate, 3070 g of pure water and 1235 g of 25% aqueous sodium hydroxide solution (7.72 mol of sodium hydroxide), 1647 mL of 80 mass% t-butanol aqueous solution was added. While maintaining this solution at 3 ° C., 1760 g (7.56 mol) of cocoyl chloride was added dropwise with stirring while adjusting the pH to 12 with 25% sodium hydroxide. The time for the acylation step was 6.0 hours.
  • Triethanolamine is added to the organic layer so that 50% of the carboxyl groups of the N-cocoyl-L-glutamic acid in the separated organic layer are in the form of a salt, and the solid content is further 30% by mass. Pure water was added. Thereafter, using a spray-type evaporator, pure water was added so as to maintain the solid content at 30% by mass, and distilled under reduced pressure at 70 ° C. for 20 hours to obtain an N-cocoyl-L-glutamic acid triethanolamine aqueous solution. Obtained (yield 97%). Table 1 shows the composition of the aqueous solution (detergent composition).
  • Example 8 An aqueous solution containing 30% by mass of N-cocoyl-L-glutamic acid was obtained under the same conditions as in Example 7 except that the time for the acylation step was 30 hours (yield 98%).
  • Table 1 shows the composition of the aqueous solution (detergent composition).
  • Example 9 An aqueous solution containing 30% by mass of N-cocoyl-L-glutamic acid was obtained under the same conditions as in Example 7 except that the time for the acylation step was changed to 55 hours (yield 97%).
  • Table 1 shows the composition of the aqueous solution (detergent composition).
  • Example 10 (Acylation step) To a mixed solution of 860 g (5.55 mol) of monosodium L-aspartate, 2978 g of pure water, and 222 g (5.55 mol) of sodium hydroxide was added 1049 g of 80% by mass t-butanol aqueous solution, and this solution was maintained at 3 ° C. While adjusting the pH to 12 with 25% by mass sodium hydroxide, 1210 g (about 5.2 mol) of lauroyl chloride was added dropwise with stirring. The time for the acylation step was 32 hours.
  • Example 11 An aqueous solution of N-lauroyl-L-aspartic acid sodium salt was obtained under the same conditions as in Example 10 except that the time of the acid precipitation step was 15 hours and the time of the solvent distillation step was 80 hours (yield) 95%).
  • Table 1 shows the composition of the aqueous solution (detergent composition).
  • Example 12 An aqueous solution of sodium N-lauroyl-L-aspartate is obtained under the same conditions as in Example 10 except that the time of the acid precipitation step of the acylation step is 15 hours and the time of the solvent distillation step is 80 hours. (Yield 95%).
  • Table 1 shows the composition of the aqueous solution (detergent composition).
  • Example 13 An aqueous solution was obtained by adding the free fatty acid of lauric acid to 5% by mass to the composition obtained in Example 12.
  • Table 1 shows the composition of the aqueous solution (detergent composition).
  • Examples 10 to 13 are in accordance with the production method of the present embodiment, a composition containing fatty acid t-butyl ester or fatty acid is obtained, and foaming durability, foam fineness, foam elasticity, and detergency Both were good.
  • Comparative Examples 2 to 3 did not follow the production method of the present embodiment, a composition containing fatty acid t-butyl ester was not obtained, there were many free fatty acids, foaming durability, foam fineness, foam Both the elasticity and the detergency were inferior to those of Examples 10 to 13.
  • Examples 14 to 21, Comparative Examples 4 to 5 A cleaning composition having the composition shown in Table 2 was prepared, and foaming durability and viscosity were evaluated. Since the cleaning compositions in Examples 14 to 21 contain fatty acid t-butyl ester, they tend to have excellent foaming durability and high viscosity. On the other hand, since the cleaning compositions in Comparative Examples 4 to 5 did not contain fatty acid t-butyl ester, the foaming persistence and the viscosity tended to be lower than those of Examples 14 to 21.
  • the cleaning composition and the method for producing the same not only the initial foaming power but also “long foaming”, “the foamy elasticity”, “the fineness of the foam texture And the like can be provided.

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Abstract

La présente invention concerne une composition de produit de nettoyage qui contient un acide aminé N-acyle acide ayant une structure spécifique et/ou un sel de celui-ci (constituant (A)) et un ester t-butylique d'acide gras ayant une structure spécifique (constituant (B)).
PCT/JP2017/015010 2016-04-14 2017-04-12 Composition de produit de nettoyage et procédé pour le produire Ceased WO2017179627A1 (fr)

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KR1020187023028A KR102051789B1 (ko) 2016-04-14 2017-04-12 세정제 조성물 및 그 제조 방법

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CN113825828B (zh) * 2019-06-14 2023-10-13 陶氏环球技术有限责任公司 液体衣物洗涤剂配制物
TW202523719A (zh) * 2020-03-19 2025-06-16 美商富士軟片電子材料美國股份有限公司 清潔組成物及其使用方法
US20230414481A1 (en) * 2020-11-02 2023-12-28 Asahi Kasei Finechem Co., Ltd. Composition and Method for Producing Same and Cosmetic Agent
CN113526517B (zh) * 2021-08-11 2023-01-10 内蒙古宁城天宇膨润土科技有限公司 用于葡萄酒和果汁澄清的膨润土、制备方法及其用途
CN114192040A (zh) * 2021-12-22 2022-03-18 徐州克林斯曼安防科技有限公司 一种适用于锂离子电池灭火剂的生产方法
KR102829585B1 (ko) * 2022-12-09 2025-07-07 (주)아모레퍼시픽 기포 조밀도 및 기포 탄력성 향상용 첨가제 조성물 및 피부 세정용 조성물

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WO2000040546A1 (fr) * 1998-12-28 2000-07-13 Asahi Kasei Kabushiki Kaisha Processus de production d'acide amine acide n-(chaine acyle longue)
WO2005032509A1 (fr) * 2003-10-02 2005-04-14 Asahi Kasei Chemicals Corporation Composition de detergent
JP2005325187A (ja) * 2004-05-13 2005-11-24 Asahi Kasei Chemicals Corp 洗浄剤組成物
JP2014169461A (ja) * 2014-06-26 2014-09-18 Asahi Kasei Chemicals Corp 洗浄剤組成物

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WO2000040546A1 (fr) * 1998-12-28 2000-07-13 Asahi Kasei Kabushiki Kaisha Processus de production d'acide amine acide n-(chaine acyle longue)
WO2005032509A1 (fr) * 2003-10-02 2005-04-14 Asahi Kasei Chemicals Corporation Composition de detergent
JP2005325187A (ja) * 2004-05-13 2005-11-24 Asahi Kasei Chemicals Corp 洗浄剤組成物
JP2014169461A (ja) * 2014-06-26 2014-09-18 Asahi Kasei Chemicals Corp 洗浄剤組成物

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US12318466B2 (en) * 2018-09-18 2025-06-03 Ajinomoto Co., Inc. Hair cleanser

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