JP2002193788A - Cleansing agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a cleansing agent having excellent stability, cleansing power and feeling in use and giving the skin comfortable feeling after cleaning. SOLUTION: The cleansing agent is formulated with an alkyl ether and/or alkenyl ether of raffinose for which 1-24C alkyl group or 3-24C alkenyl group is substituted at an average substitution number of 1-11.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a cleaning agent which is excellent in stability and feel during use, and also has excellent skin feel and cleanability after washing.

[0002]

2. Description of the Related Art Conventionally, there have been reported a large number of detergents using a sugar-based surfactant, for example, a detergent containing a sucrose ester, under the influence of skin safety and plant preferences in the market. . In addition, as a sugar-based surfactant, JP-B-47-7
No. 762 proposes a raffinose ester-based surfactant.

[0003]

However, these publications do not describe the alkyl ether and alkenyl ether forms of raffinose and their characteristics, and furthermore, the fatty acid ester form of raffinose which is the surfactant of the above publication is not disclosed. In the case of a water-based preparation, depending on the combination of the ingredients in the preparation, the performance may deteriorate over time, or the behavior may be sensitive to a change in pH, and it may be difficult to formulate the formulation. In addition, sugar-based surfactants have poor stability at high temperatures and have disadvantages such as discoloration and deterioration. In addition, there are skin and hair cleaners containing various surfactants other than sugar-based surfactants.
There were no satisfactory feelings such as ease of rinsing, feeling of tightness of the washed skin, and cleaning properties. That is, an object of the present invention is to provide a detergent excellent in stability, detergency, feel during use, and skin feel after cleaning.

[0004]

Means for Solving the Problems In view of these problems, the present inventors have made various studies and found that the number of carbon atoms is one.
The detergent containing the alkyl group of ２４24 or the alkenyl group of 3-24 carbon atoms and the alkyl ether of raffinose and / or the alkenyl ether of raffinose having an average number of substitution of 1-11 is stable and has good cleaning properties. sex,
The present invention was found to be excellent in the feel during use and the skin feel after washing, and completed the present invention.

That is, the first aspect of the present invention has a carbon number of 1 to 1.
An alkyl group having 24 or an alkenyl group having 3 to 24 carbon atoms, and an alkyl ether of raffinose and / or an alkenyl ether of raffinose having an average substitution number of 1 to 11 are blended. is there.

A second aspect of the present invention resides in the above-mentioned detergent, which further comprises a fatty acid soap having 10 to 22 carbon atoms and / or an N-acylamino acid salt.

A third aspect of the present invention is that the alkyl group of raffinose and / or the alkenyl ether of raffinose has an alkyl group having 10 to 18 carbon atoms, and the alkenyl group has 10 to 18 carbon atoms. The above-mentioned cleaning agent is characterized in that the average number of substitution is 1-2.

[0008]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Raffinose used in the present invention is a kind of trisaccharide and is O-α-D-galactopyranosyl- (1,6) -O-α-D-glucopyranosyl- (1,1).
2) It has a structure of -β-D-fructofuranoside. Raffinose can be obtained synthetically or naturally, as described in JP-A-10-84773. Natural products are preferred because natural products have excellent images and can be easily obtained with high purity. Natural products can be obtained from eucalyptus manna, sugar beet molasses, cotton seeds, legume seeds, lotus seeds, etc., but those derived from sugar beet molasses must be supplied stably. Is most preferred.

The alkyl ether or alkenyl ether of raffinose used in the detergent of the present invention includes:
A straight-chain or branched alkyl group having 1 to 24 carbon atoms or an alkenyl group having 3 to 24 carbon atoms (unsaturated bond) via oxygen atoms of all or some of the 11 hydroxyl groups of raffinose. Which has been etherified and substituted, and preferably has 6 carbon atoms.
~ 20, particularly preferably an alkyl group having 10 to 18 carbon atoms, or preferably an alkyl group having 6 to 20 carbon atoms, particularly preferably an alkenyl group having 10 to 18 carbon atoms. Those in the range of 1 to 2 are particularly preferable because they are excellent in improving stickiness and feeling of washing, and are excellent in detergent and rinsing properties as a surfactant in addition to an oil agent. Further, when the average number of substitution is 2 or more, it particularly shows properties as an emulsifier to an oil agent, depending on the alkyl chain length and the alkenyl chain length. Then, as the average substitution number increases, the characteristics of the solid oil come to be exhibited. In the present invention, when an alkyl ether or alkenyl ether of raffinose is used as an oil, it can be used as a liquid oil or a solid oil depending on the characteristics of the dosage form. The number of substituents is, for example, proton NMR
(Nuclear magnetic resonance spectrum).

The method for obtaining the alkyl ether form and alkenyl ether form of raffinose in the detergent of the present invention will be described in detail in the following Examples.
(1) In a reaction solvent such as propylene glycol, in the presence of an alkali such as sodium methoxide, or a surfactant such as sodium stearate, an alkyl bromide or alkyl having 1 to 24 carbon atoms in an amount corresponding to the number of substitutions therein. Alkyl halides such as chlorides, or 3 to 2 carbon atoms
(4) a method of reacting an alkenyl halide such as alkenyl chloride or alkenyl bromide to produce an ether derivative, (2) using a sodium methoxide or sodium hydride in an aprotic solvent such as N, N-dimethylformamide The alkoxide is used to convert the hydroxyl group of raffinose to an alkoxide having an amount of 1 to 24 carbon atoms according to the number of substitutions.
Reaction of an alkyl halide such as an alkyl bromide or an alkyl chloride, or an alkenyl halide such as an alkenyl chloride or an alkenyl bromide having 3 to 24 carbon atoms to produce an ether derivative, and (3) a non-method such as dimethyl sulfoxide or N-methylpyrrolidinone. Using a protic solvent, preferably dimethylsulfoxide, which provides a high reaction yield, is used as the reaction solvent, and an alkyl halide having 1 to 24 carbon atoms and / or an alkenyl having 3 to 24 carbon atoms in an amount corresponding to the number of substitutions. Halide and raffinose together with an alkali such as sodium hydroxide, potassium hydroxide, calcium oxide, barium oxide, and sodium alkoxide such as sodium methoxide, preferably sodium hydroxide and hydroxyl which are alkalis capable of obtaining a high reaction yield A method of producing an ether derivative by adding potassium and sodium alkoxides and reacting the same can be mentioned. Particularly, the production method (3) has a high yield, can use general-purpose raw materials as raw materials to be used, and can reduce costs. preferable. In all methods, it is preferable to use an inert gas during the reaction. In this case, the state of alkyl etherification and alkenyl etherification can be analyzed by proton NMR after separating the obtained synthesized product by a column.

As for the conditions during the production, the reaction temperature is preferably 70 to 150 ° C. in the method (1), and the reaction time is, for example, 1 to 8 hours at 120 ° C., and the reaction temperature is 1 to 8 hours in the method (2). Preferably, the reaction temperature is preferably 20 to 100 ° C, and the reaction time is, for example, 45 ° C for 5 to 60 hours. In the method (3), the reaction temperature is preferably 60 to 150 ° C, and the reaction time is, for example, 100 ° C for 1 to 8 hours. It is. The raw material ratio is preferably from 0.5 to 8 equivalents of alkyl halide or alkenyl halide to 1 equivalent of raffinose. After the reaction is completed, the reaction solvent is removed under reduced pressure and heating conditions, and the residue is precipitated by adding (1) a solvent in which the ether derivative is not dissolved, such as ethyl acetate, (2)
It can be purified by a method of removing impurities using a column filled with silica gel or the like. If necessary, salts of reaction by-products can be removed with a desalting resin or the like.

The mixing ratio of the alkyl ether of raffinose and / or the alkenyl ether of raffinose to the detergent of the present invention is preferably 0.01 to 50% by mass relative to the total amount of the detergent. More preferably, the content is 0.1 to 40% by mass.

The detergent of the present invention preferably contains other surfactants in addition to the alkyl ether of raffinose and / or the alkenyl ether of raffinose. Examples of surfactants include, for example, anionic surfactants, cationic surfactants, nonionic surfactants,
Amphoteric surfactants are included. More specifically, fatty acid soap, α-acyl sulfonate, alkyl sulfonate,
Alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, alkyl ether sulfate,
Alkyl amide sulfates, alkyl phosphates, alkyl amide phosphates, alkylloylalkyl taurine salts, N-
Acyl amino acid salts, sulfosuccinates, anionic surfactants such as perfluoroalkyl phosphates, alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride,
Cationic surfactants such as distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, alkanolamide laurate, POE sorbitan fatty acid ester, POE glycerin fatty acid ester, POE fatty acid ester, polyether-modified silicone, etc. Nonionic surfactant, carboxybetaine type, amidobetaine type,
Examples include amphoteric surfactants such as sulfobetaine type, hydroxysulfobetaine type, amidosulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type and amidoamine type. In addition, natural surfactants such as saponins and sugar surfactants can be used. Among them, those having 10 to 22 carbon atoms, particularly preferably those having 12 carbon atoms
When fatty acid soaps and / or N-acyl amino acid salts are used in combination, the raffinose alkyl ether can give rise to foaming and a finished feeling which is a drawback of the fatty acid soaps, or a feeling of a slimy finish which is a drawback of the N-acyl amino acid salts. It is preferable to use the alkenyl ether derivative of the compound and / or raffinose in combination, because it can be improved and other combined effects can be obtained. Examples of the fatty acid soap include sodium salts, potassium salts, and amine salts such as triethanolamine of fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, and coconut oil fatty acids. The N-acyl amino acid salt is an N-acyl amino acid salt having an acyl group having 10 to 22 carbon atoms, for example, sodium N-lauroylglutamate, triethanolamine N-lauroylglutamate, sodium N-myristoylglutamate, N- N-acyl glutamates such as myristoylglutamate triethanolamine, sodium N-palmitoylglutamate, triethanolamine N-palmitoylglutamate, sodium N-stearoylglutamate, sodium N-oleoylglutamate, disodium N-palmitoylglutamate, N-lauroyl Sodium aspartate, N-lauroyl aspartate triethanolamine, N-myristoyl sodium aspartate, N-myristoyl as N-acyl aspartates such as triethanolamine laginate, N-acyl (coconut oil fatty acid) aspartate triethanolamine, sodium N-lauroylglycine, N-lauroylglycine triethanolamine, sodium N-myristoylglycine, N- N-acyl glycine salts such as myristoyl glycine triethanolamine, potassium N-acyl (coconut oil fatty acid) glycine, other N-acylmethyl taurine salts, N-acylmethylalanine salts, N
Acyl sarcosine salts and the like;
-Acylglutamic acid salts and N-acylglycine salts are preferred.

The above surfactant or fatty acid soap and / or
Alternatively, the amount of the N-acyl amino acid salt to be added to the detergent varies depending on the type of the detergent, but is generally 1.0%.
To 97% by mass, specifically 20
It is preferably from 50 to 50% by mass, 20 to 25% by mass for body use, and 10 to 20% by mass for makeup remover.

[0015] In the cleaning agent of the present invention, in addition to the above components, conventionally known powders, oils, adhesives, humectants, salts,
An ultraviolet protection component, a physiologically active component, an antiseptic preservative, a pH adjuster, a chelating agent, a fragrance, a coloring agent, a solvent and the like can be appropriately compounded.

Examples of the tackifier include, for example, an acrylic ester / methacrylic ester copolymer (plus size, manufactured by Yoyo Kagaku) and a vinyl acetate / crotonic acid copolymer (resin 28-1310, manufactured by NSC). , Vinyl acetate /
Crotonic acid / vinyl neodecanoate copolymer (28-2
930, manufactured by NSC), methyl vinyl ether maleic acid half ester (Gantrez ES, manufactured by ISP),
t-butyl acrylate / ethyl acrylate / methacrylic acid copolymer (Rubimer, manufactured by BASF), vinyl pyrrolidone / vinyl acetate / vinyl propionate copolymer (Ruviscol VAP, manufactured by BASF), vinyl acetate / crotonic acid Copolymer (Rubiset CA, BA
SF), vinyl acetate / crotonic acid / vinyl pyrrolidone copolymer (Rubiset CAP, manufactured by BASF), vinyl pyrrolidone / acrylate copolymer (Rubiflex, manufactured by BASF), acrylate / acrylamide copolymer (Ultrahold) , Manufactured by BASF)
Vinyl acetate / butyl maleate / isobornyl acrylate copolymer (Advantage, manufactured by ISP),
Carboxyvinyl polymer (Carbopol, BFG
OODRICH), anionic polymer compounds such as cross-linked polyacrylic acid (Pemulen, BF GOODRICH), acetic acid amphoteric dialkylaminoethyl methacrylate polymer (Yukaformer, manufactured by Mitsubishi Chemical Corporation), octyl acrylate Amphoteric polymer compounds such as acrylamide / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer (AMPHOMER, manufactured by NSC) and quaternized vinylpyrrolidone / dimethylaminoethyl methacrylate (GAFQUAT, IS
P), methyl vinyl imidazolium chloride / vinyl pyrrolidone copolymer (Rubicoat, manufactured by BASF), and other cationic polymer compounds such as polyvinyl pyrrolidone (Rubiscol K, manufactured by BASF), vinyl pyrrolidone / vinyl acetate A polymer (Rubiscol VA, manufactured by BASF), a vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (Copolymer 937, manufactured by ISP),
Vinyl caprolactam / vinyl pyrrolidone / dimethylaminoethyl methacrylate copolymer (Copolymer VC7
13, manufactured by ISP). In addition, cellulose or a derivative thereof, keratin and collagen or a derivative thereof, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharide, xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabino Naturally occurring polymer compounds such as galactan, karaya gum, tragacanth gum, alginic acid, albumin, casein, curdlan, gellan gum, and dextran can also be suitably used.

In the present invention, it is preferable to add a physiologically active ingredient, and examples of the physiologically active ingredient include substances that give some physiological activity to the skin when applied to the skin or the like.
For example, anti-inflammatory agents, tightening agents, moisturizers, blood circulation enhancers,
Antiseptic, preservative, cooling sensation, warming sensation, vitamins, amino acids
Examples include a wound healing promoter, an enzyme component and the like. Among them, natural plant extract components, seaweed extract components, and crude drug components are particularly preferable, and it is preferable to mix one or more of these physiologically active components in a compounding amount that exhibits an effect. For example, Ashitaba extract, Avocado extract, Amacha extract, Altea extract, Arnica extract, Aloe extract, Apricot extract, Apricot kernel extract, Ginkgo extract, Turmeric extract, Oolong tea extract, Age extract, Echinashi leaf extract, Ogon extract, Oubaku extract, Barley extract Extracts, Hypericum perforatum extract, Red oleander extract, Dutch mustard extract, orange extract, seawater dried product, hydrolyzed elastin, hydrolyzed wheat powder, hydrolyzed silk, syllium extract, chamomile extract, carrot extract, valerium extract, calcaret extract, kiwi extract, Kina extract, Cucumber extract, Guanosine, Gardenia extract, Kumazasa extract, Clara extract, Cranberry extract, Walnut extract, Grapefruit extract, Clematis Kiss, chlorella extract, mulberry extract, gentian extract, black tea extract, yeast extract, burdock root extract, rice bran fermentation extract, rice germ oil,
Comfrey extract, Collagen, Biloba extract, Psychic extract, Psychoextract, Saitai extract, Salvia extract, Sabonso extract, Sasa extract, Hawthorn extract, Sansho extract, Shiitake extract, Jio extract, Shikon extract, Perilla extract, Shinanoki extract, Shimotsusou extract, Peonies extract, shobu root extract, birch extract, horsetail extract, sugar beet extract, Atlantic hawthorn extract, Atlantic elderberry extract, Achillea millefolium extract, Atlantic peppermint extract, Sage extract, Xenopus extract, Senkyu extract, Japanese soybean extract, Soybean extract, Japanese radish extract,
Thyme extract, chiyaya extract, chimpi extract, touki extract, calendula extract, tonin extract, spruce extract, dokudami extract, tomato extract, natto extract,
Carrot extract, Garlic extract, Novara extract, Hibiscus extract, Bacmondou extract, Lotus extract, Parsley extract, honey, Parietaria extract, Hioki sorghum extract, Bisabolol, Coltsfoot poppo extract, Fukinotou extract, Bucurio extract, Butcher bloom extract, Grape extract, Propolis, Loofah extract, safflower extract, peppermint extract, bodaiju extract, button extract, hop extract, pine extract, pine extract, peach sap extract, peach leaf extract, cornflower extract, eucalyptus extract, saxifrage extract, yuzu extract, yokuninin extract, mugwort extract, lavender extract , Lettuce extract, lemon extract, astragalus extract, rose extract, Roman chamomile extract, royal jelly extract, etc. Door can be.

In addition, biopolymers such as mucopolysaccharide, sodium hyaluronate, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, hydrolyzed eggshell membranes, glycine, valine, leucine, isoleucine, serine, threonine, phenylalanine, arginine , Lysine, aspartic acid, glutamic acid, cystine, cysteine, methionine, tryptophan and other amino acids, hormones such as estradiol, ethenyl estradiol, amino acids, sodium lactate, urea, sodium pyrrolidonecarboxylate, moisturizing ingredients such as betaine, whey, sphingolipids , Ceramide, cholesterol, cholesterol derivatives, oily components such as phospholipids,
anti-inflammatory agents such as ε-aminocaproic acid, glycyrrhizic acid, β-glycyrrhetinic acid, lysozyme chloride, guaiazulene, hydrocortisone, allantoin, tranexamic acid, azulene, vitamins A, B2, B6, C, D, E,
K, calcium pantothenate, biotin, nicotinamide, active ingredients such as allantoin, diisopropylamine dichloroacetate, 4-aminomethylcyclohexanecarboxylic acid, cell activators such as α-hydroxy acid, β-hydroxy acid, γ-oryzanol, etc. Blood circulation enhancer,
Wound healing agents such as retinol and retinol derivatives, cepharanthin, licorice extract, pepper tincture, hinokitiol, garlic iodide extract, pyridoxine hydrochloride,
Nicotinic acid, nicotinic acid derivative, calcium pantothenate, D-pantothenyl alcohol, acetyl pantothenyl ethyl ether, biotin, allantoin, isopropylmethylphenol, estradiol, ethinylestradiol, capronium chloride, benzalkonium chloride, diphenhydramine hydrochloride, tacanal, camphor , Salicylic acid, nonyl acid vanillyl amide, nonanoic acid vanillyl amide, pyroctone olamine, glyceryl pentadecanoate, l-menthol, camphor and the like, and the like, as physiologically active ingredients.

Examples of oils include avocado oil, linseed oil, almond oil, ibotaro wax, eno oil, olive oil, cacao butter, kapok wax, kaya oil, carnauba wax, liver oil, candelilla wax, tallow, beef tallow, beef bone Fat,
Hardened beef tallow, ginger oil, whale wax, hardened oil, wheat germ oil, sesame oil, rice germ oil, rice bran oil, sugarcane wax, sasanqua oil, safflower oil, shea butter, cinnamon oil, cinnamon oil, jojoba wax, shellac wax, turtle Oil, soybean oil, teaseed oil, camellia oil, evening primrose oil, corn oil, lard oil, rapeseed oil, Japanese kiri oil, bran wax, germ oil, horse fat, persic oil, palm oil, palm kernel oil, castor oil, hardened Castor oil, castor oil fatty acid methyl ester, sunflower oil, grape oil, bayberry wax, jojoba oil, macadamia nut oil, beeswax, mink oil, cottonseed oil, cotton wax, mokuro, mokuro kernel oil, montan wax,
Coconut oil, hydrogenated coconut oil, coconut oil fatty acid triglyceride,
Wool fat, peanut oil, lanolin, liquid lanolin, reduced lanolin, lanolin alcohol, hard lanolin, lanolin acetate, lanolin fatty acid isopropyl, hexyl laurate, egg yolk oil, etc .; hydrocarbon oils such as ozokerite, squalane, squalene, ceresin, paraffin, Paraffin wax, liquid paraffin, pristane, polyisobutylene, microcrystalline wax, petrolatum, etc .;
Higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, undecylenic acid,
Oleic acid, linoleic acid, linolenic acid, arachidonic acid,
Eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), isostearic acid, 12-hydroxystearic acid and the like; as higher alcohols, lauryl alcohol, myristyl alcohol, palmityl alcohol,
Stearyl alcohol, behenyl alcohol, hexadecyl alcohol, oleyl alcohol, isostearyl alcohol, hexyldecanol, octyldodecanol, cetostearyl alcohol, 2-decyltetradecinol, cholesterol, phytosterol, etc .; ester oils such as diisobutyl adipate, adipin 2-hexyldecyl acid, di-2-heptylundecyl adipate, N-alkyl glycol monoisostearate, isononyl isononanoate, isocetyl isostearate, trimethylolpropane triisostearate,
Ethylene glycol di-2-ethylhexanoate, cetyl 2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl octanoate, octyldodecyl gum ester, oleyl oleate Octyldodecyl oleate, decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, amyl acetate, ethyl acetate, butyl acetate, isocetyl stearate, butyl stearate,
Diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, myristyl lactate, isopropyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, cholesteryl 12-hydroxystearylate, Dipentaerythritol fatty acid ester, isopropyl myristate, octyldodecyl myristate,
2-hexyldecyl myristate, myristyl myristate, hexyldecyl dimethyloctanoate, ethyl laurate, hexyl laurate, diisostearyl malate and the like; glyceride oils include acetoglyceryl, glyceryl triisooctanoate, glyceryl triisostearate, Examples include glyceryl triisopalmitate, glyceryl monostearate, glyceryl di-2-heptylundecanoate, glyceryl trimyristate, and diglyceryl isostearate myristate.

The detergent of the present invention includes ethylene glycol, diethylene glycol, polyethylene glycol,
Propylene glycol, dipropylene glycol, polypropylene glycol, glycerin, diglycerin, polyglycerin, 3-methyl-1,3-butanediol,
1,3-butylene glycol, sorbitol, mannitol, glucose, sucrose, fructose, xylitol, lactose, raffinose, maltose, maltitol, trehalose, mixed isomerized sugar, sulfated trehalose, polyhydric alcohol such as pullulan, It is preferable to mix 2 to 40% by mass for imparting a moisturizing effect.

Examples of antibacterial and preservatives include alkyl paraoxybenzoate, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, and phenoxyethanol. Antibacterial agents include benzoic acid, salicylic acid, phenolic acid, and the like.
Sorbic acid, alkyl paraoxybenzoate, parachloromethcresol, hexachlorophen, benzalkonium chloride, chlorhexidine chloride, trichlorocarbanilide, triclosan, photosensitizer, phenoxyethanol and the like.

Examples of powders and coloring agents include those used in ordinary cosmetics, such as shapes (spherical, rod-like, needle-like, plate-like, irregular, scaly, spindle-like, etc.) Regardless of the particle size (fog, fine particles, pigment grade, etc.) and particle structure (porous, non-porous, etc.), any can be used. For example, inorganic powder, organic powder, surfactant Metal salt powders, colored pigments, pearl pigments, metal powder pigments, natural pigments, and the like can be mentioned. Specifically, as inorganic powders, pigment grade titanium oxide, zirconium oxide, pigment grade zinc oxide, cerium oxide, oxide Magnesium, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite, synthetic mica, phlogopite, phlogopite, biotite, lithia mica,
Silicic acid, Silicic anhydride, Aluminum silicate, Magnesium silicate, Magnesium aluminum silicate, Calcium silicate, Barium silicate, Strontium silicate, Metal tungstate, Hydroxyapatite, Vermiculite, Heidilite, Bentonite, Montmorillonite, Hector Light, zeolite, ceramic powder, dicalcium phosphate, alumina, aluminum hydroxide, boron nitride, boron nitride, silica, fine titanium oxide, fine zinc oxide, fine cerium oxide, etc .; as organic powders, polyamide powder, polyester powder, Polyethylene powder, polypropylene powder,
Polystyrene powder, polyurethane powder, benzoguanamine powder, polymethylbenzoguanamine powder, polytetrafluoroethylene powder, polymethyl methacrylate powder, cellulose, silk powder, silicone powder, silicone rubber powder, silicone elastomer spherical powder, styrene / acrylic acid copolymer , Divinylbenzene / styrene copolymer, vinyl resin, urea resin, phenolic resin, fluororesin, silicon resin, acrylic resin, melamine resin, epoxy resin,
Polycarbonate resin, microcrystalline fiber powder, starch powder,
Lauroyl lysine, etc .; surfactant metal salt powders (metal soaps) include zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate, cetyl phosphate Zinc sodium, etc .; colored pigments include inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate; inorganic brown pigments such as γ-iron oxide; inorganic yellow pigments such as yellow iron oxide and loess; and black iron oxide , Inorganic black pigments such as carbon black, inorganic purple pigments such as manganese violet and cobalt violet, inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide and cobalt titanate, inorganic blue pigments such as navy blue and ultramarine blue, tar Lakes of natural pigments, lakes of natural pigments, Pearl pigments include titanium oxide-coated mica, titanium oxide-coated mica, bismuth oxychloride, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, fish scale foil, titanium oxide-coated Colored mica and the like; as tar dyes, Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 202, Red No. 204, Red No. 205
No. Red 220, Red 226, Red 227, Red 228, Red 230, Red 401, Red 505
No. 4, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203
No., Yellow No. 204, Yellow No. 401, Blue No. 1, Blue No. 2
No., Blue No. 201, Blue No. 404, Green No. 3, Green No. 20
No. 1, Green No. 204, Green No. 205, Orange No. 201, Orange No. 203, Orange No. 204, Orange No. 206, Orange No. 207
No. etc .; natural pigments include carminic acid, raccaic acid,
A powder selected from calsamine, brasilin, crocin, and the like, and these powders can be used as composites of powders or general oils, silicone oils, fluorine compounds, as long as the effects of the present invention are not impaired.
Those treated with a surfactant or the like can also be used.
For example, fluorine compound treatment, silicone resin treatment, pendant treatment, silane coupling agent treatment, titanium coupling agent treatment, oil treatment, N-acylated lysine treatment, polyacrylic acid treatment, metal soap treatment, amino acid treatment, inorganic compound treatment The surface treatment may or may not be performed in advance by plasma treatment, mechanochemical treatment, or the like, and one or more surface treatments may be used in combination as needed. In the present invention, one or more of these powders can be used in combination. In particular, it is preferable to blend a polyamide powder, a polyester powder, a polyethylene powder, a polypropylene powder, a polystyrene powder, a polyurethane powder, a polymethyl methacrylate powder, and a cellulose powder, particularly a spherical powder, as a scrubbing agent in the detergent.

[0023] The cleaning agent of the present invention includes facial, hair and
Examples include systemic and topical cleaning agents, and they can also be used for cleaning contact lenses and the like. Examples of cleansing agents include facial cleansers, makeup removers, lip cleansing, cleansing agents, body shampoos, shampoos,
Examples include, but are not limited to, soaps and the like, but are particularly suitable as skin cleansing agents. Examples of the form of the cleaning agent include liquid, gel, cream, foam, and sheet. Further, the appearance may be transparent or opaque due to cloudiness.

[0024]

The present invention will be specifically described below with reference to examples and comparative examples. The sensory evaluation methods for the cleaning agents obtained in Examples and Comparative Examples are shown below.

[Evaluation of Sensory Characteristics] Ten expert panelists were prepared for each evaluation item (however, panelists may be duplicated depending on the item), and evaluation was performed according to the evaluation criteria shown in Table 1, and the total of all panelists was calculated. The evaluation results were given based on points. Therefore, the higher the score, the higher the usefulness for the evaluation item is shown (full score: 50 points). In addition, as evaluation items, four items of good defoaming, good rinsing, fast washing, and high detergency were evaluated.

[Table 1] Reference points --------------------------------------- -The effect is felt high 5 The effect is felt 4 The effect is felt slightly 3 The effect is felt only slightly 2 The effect is not felt 1

[Evaluation of stability] With respect to the preparations obtained in Examples and Comparative Examples, room temperature and high temperature (45 ° C) and low temperature (5 ° C)
For 2 months, and changes in appearance (color, separation, precipitation, etc.) from those immediately after production were visually observed. The state of the change is shown for each of the cases where the change has occurred.

Synthesis Example 1 (Synthesis example of monododecyl ether of raffinose) 200 mg of sodium hydride and 10 ml of dimethyl sulfoxide were added to a dried 200 ml eggplant-shaped flask, and then raffinose (anhydrous anhydride) dissolved in 12 ml of dimethyl sulfoxide ) 2.5 g was added. 2.5 hours later, 2.5 g of raffinose (anhydrous) dissolved in 12 ml of dimethyl sulfoxide was added to the reaction solution, and then 1-
1.2 ml of bromododecane was gradually added dropwise, and the mixture was stirred at 45 ° C., and the reaction was terminated after 46.5 hours. The reaction solution was extracted by adding n-hexane and methanol, and methanol and dimethyl sulfoxide were removed while heating the methanol phase under reduced pressure to 120 ° C. Isopropanol and methanol were added to the residue, followed by stirring at room temperature for 2 hours, followed by filtration. The filtrate was concentrated and purified by a silica gel flash column to obtain 3.36 g of cream crystals. The crystals were dissolved in heavy water and subjected to proton NMR measurement to confirm that the crystals were a radonose monododecyl ether. FIG. 1 shows an infrared absorption spectrum of the crystal.

Synthesis Example 2 (Synthesis Example of Dodecyl Ether Form of Raffinose) In a 200-ml eggplant flask, 5.044 g of raffinose (anhydrous) and 50 ml of dimethyl sulfoxide were added, and the mixture was stirred at 80 ° C. while reducing the pressure with an aspirator.
After 1 hour, the pressure was released and the inside of the reaction vessel was replaced with an inert gas. Then, 1.74 g of potassium hydroxide and 4.71 ml of 1-chlorododecane were added, and the mixture was stirred at 100 ° C. for 3 hours. After completion of the reaction, the reaction solution was largely removed at 120 ° C. under reduced pressure with a vacuum pump, and a small amount of methanol was added to the residue, followed by addition of ethyl acetate to precipitate. The precipitate was separated by filtration, thoroughly dried, and then desalted. The filtrate was lyophilized to give white crystals (including raffinose) containing 4.55 g of dodecyl raffinose. In addition, the number of substitution of the dodecyl group of the obtained dodecyl ether of raffinose is 1 to
In 2, the average substitution number was about 1.5.

Using the alkyl ether of raffinose obtained in the above example, the following detergent was prepared.

Example 1 Cream soap A cream soap was obtained according to the formulation and the production method shown in Table 2. The dodecylated raffinose used was the one produced in Synthesis Example 1. The unit of the compounding amount is mass%.

[Table 2] Ingredients Compounding amount --------------------------------------- -------- (1) Lauric acid 1.0 (2) Myristic acid 4.0 (3) Stearic acid 0.5 (4) Potassium hydroxide 4.0 (5) Dodecylated raffinose 5.0 (6) Glycerin 5.0 (7) Sodium cocoyl methyl taurine 5.0 (8) Citric acid 0.5 (9) Polyethylene glycol 4000 3.0 (10) Peach leaf extract 0.5 (11) Remainder

[Production method] (a): Components (1) to (3) are uniformly dissolved at about 80 ° C. (B): A part of the component (4) and a part of the component (11) are uniformly dissolved at about 80 ° C. (C): Components (5) to (10) and the remainder of component (11) are uniformly dissolved at about 80 ° C. (B) was added to (a) for neutralization, and then (c) was added for about 3
After cooling to 0 ° C, the container was filled to obtain a cream soap.

Example 2 Cream soap (weakly acidic) Cream soap (weakly acidic) according to the formulation and production method in Table 3.
I got As the dodecylated raffinose, the one produced in Synthesis Example 2 was used.

[Table 3] Ingredient Compounding amount --------------------------------------- -------------------- (1) Sodium lauroyl glutamate 23.0 (2) Stearic acid 1.0 (3) Myristic acid 0.5 (4) Dodecylation Raffinose 3.0 (5) Ethylene glycol distearate 1.0 (6) Glycerin 15.0 (7) 1,3-butylene glycol 2.0 (8) Polyethylene glycol 20000 10.0 (9) Trimethylglycine 0 (10) Aloe extract 0.3 (11) Purified water balance

[Production Method] (a): Components (1) to (7) and a part of the component (11) are mixed and dissolved at about 80 ° C. After dissolution, the components (8) to (1)
0) and the remainder of (11) were added, and the mixture was cooled with stirring to about 30 ° C to obtain a cream soap having a pH of 6.0.

Comparative Example 1 A product was obtained in the same manner as in Example 1 except that purified water was used in place of dodecylated raffinose.

Comparative Example 2 A product was obtained in the same manner as in Example 1 except that raffinose was used in place of dodecylated raffinose.

Comparative Example 3 Example 2 was repeated except that raffinose laurate was used in place of dodecylated raffinose of Example 2.
A product was obtained in the same manner as described above.

Tables 4 and 5 show the evaluation results of the examples and comparative examples.

[Table 4] Sensory evaluation Good bubbling, fast rinsing, fast washing, and high detergency -------------------------- ------------------------------------------ Example 1 47 45 45 44 Example 2 43 45 48 42 Comparative Example 1 20 42 48 32 Comparative Example 2 30 38 20 34 Comparative Example 3 40 22 38 43

[0042]

From the results shown in Tables 4 and 5, it can be seen that the examples of the present invention are more excellent in sensory characteristics and stability over time than the comparative examples. In particular, it was found that the present invention was excellent in the feel at the time of use such as foaming and the feeling of washing, and the examples of the present invention did not have slimy washing.

[0044]

As described above, according to the present invention, the number of carbon atoms is 1
By mixing an alkyl group of ２４24 or an alkenyl group of 3-24 carbon atoms with an alkyl ether of raffinose and / or an alkenyl ether of raffinose having an average number of substitution of 1-11, stability and washing are achieved. sex,
It is clear that a cleansing agent is obtained which is excellent in ease of rinsing, feel during use, and skin feel after washing.

[Brief description of the drawings]

FIG. 1 shows an infrared absorption spectrum of a monododecyl ether of raffinose obtained in Synthesis Example 1.

Continued on the front page F term (reference) 4C083 AA112 AB032 AC122 AC241 AC242 AC302 AC392 AC661 AC662 AC792 AD042 AD211 AD212 AD391 AD392 CC23 DD31 EE06 EE07 4H003 AB03 AB09 AB23 AC05 BA12 BA15 BA19 DA02 EA21 EB05 EB08 EB36 FA21 FA21 FA23

Claims (3)

[Claims] 1. An alkyl group having 1 to 24 carbon atoms or an alkenyl group having 3 to 24 carbon atoms, wherein an alkyl ether of raffinose and / or an alkenyl ether of raffinose having an average substitution number of 1 to 11 are used. A cleaning agent characterized by containing. 2. A fatty acid soap having 10 to 22 carbon atoms and / or
The detergent according to claim 1, further comprising an N-acyl amino acid salt. 3. An alkyl ether of raffinose and / or
Or, the alkyl group of the alkenyl ether of raffinose is in the range of 10 to 18 carbon atoms, the alkenyl group is in the range of 10 to 18 carbon atoms, and the average number of substitution is 1 to 2
The cleaning agent according to claim 1 or 2, wherein