JP2011120985A - Perfume solubilizer - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a perfume solubilizer which is excellent in solubilizing ability to various perfumes and can maintain the solubilizing ability even after long-term storage at various temperatures. <P>SOLUTION: The perfume solubilizer includes (A) a nonionic surfactant expressed by formula (1), (B) an alkylene oxide adduct of higher alcohol or an alkylene oxide adduct of an oil and fat having a hydroxyl group, and (C) an anionic surfactant. In formula (1), n is a number of 1.0 to 3.0; n pieces of Rs are each independently methylene, ethylene or ethylidene; AO is 2-4C oxyalkylene; and m is a number of 1 to 60 on average. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention relates to a fragrance solubilizer. More specifically, the present invention relates to a solubilizer for stably solubilizing a fragrance in a fragrance or cosmetics in a fragrance or various cosmetics used in rooms, toilets, cars and the like.

  Conventionally, many fragrances and cosmetics have been proposed as solubilizers for preventing perfume separation. For example, an alkylene oxide adduct of a higher alcohol having a branched alkyl group or an alkenyl group (Patent Document 1), an ethylene oxide or propylene oxide adduct of a phenol (Patent Document 2), an alkylene oxide adduct of an aliphatic alcohol Also known are blends of ethylene oxide adducts of triglycerides (Patent Document 3), ethylene oxide adducts of alkylphenols and ethylene oxide adducts of hydrogenated castor oil (Patent Document 4), and the like. However, the solubilizers proposed so far exhibit a solubilizing ability with respect to a specific perfume, but if the type of perfume is changed, the solubilizing effect often cannot be achieved, The solubilizing ability cannot be exhibited. Moreover, even if it has been solubilized transparently immediately after blending with a fragrance, if it is stored for a long time at various temperatures (for example, 5 ° C. to 40 ° C.), depending on the type of the fragrance, it may become cloudy or frozen in winter and There was a problem that the haze did not disappear even if it was melted back.

JP-A-54-132491 JP-A-57-70197 Special table 2003-534431 gazette Japanese Patent Laid-Open No. 9-301844

  An object of the present invention is to provide a perfume solubilizing agent that is excellent in solubilization ability with respect to various fragrances and can maintain the solubilization ability even when stored at various temperatures for a long period of time.

式中、ｎは１．０〜３．０の数、ｎ個のＲはそれぞれ独立にメチレン基、エチレン基又はエチリデン基、ＡＯは炭素数２〜４のオキシアルキレン基、ｍは平均値であって１〜６０の数を表す。 The inventors of the present invention have reached the present invention as a result of intensive studies to solve the above problems. That is, the present invention relates to a nonionic surfactant (A) represented by the general formula (1), an alkylene oxide adduct of a higher alcohol or an alkylene oxide adduct (B) of a fat or oil having a hydroxyl group, and an anionic interface. It is a perfume solubilizing agent comprising the active agent (C).

In the formula, n is a number of 1.0 to 3.0, n Rs are each independently a methylene group, ethylene group or ethylidene group, AO is an oxyalkylene group having 2 to 4 carbon atoms, and m is an average value. Represents a number from 1 to 60.

  The fragrance solubilizing agent of the present invention is excellent in solubilizing ability with respect to various fragrances, and has the effect of being able to maintain the solubilizing ability even when stored at various temperatures for a long period of time and having excellent stability over time.

  As a nonionic surfactant (A) in this invention, the compound represented by General formula (1) is mentioned. In the general formula (1), n is an average value and is a number of 1.0 to 3.0, and preferably 1.5 to 2.0 from the viewpoint of aging stability. Each R is independently a methylene group, an ethylene group or an ethylidene group, and from the viewpoint of aging stability, all n R are ethylidene groups.

  AO in the general formula (1) is an oxyalkylene group having 2 to 4 carbon atoms, such as an oxyethylene group, a 1,2-oxypropylene group, a 1,3-oxypropylene group, a 1,2-oxybutylene group, 2 , 3-butylene group and 1,4-butylene group. Among these, oxyethylene group and 1,2-oxypropylene group are preferable from the viewpoint of aging stability. AO may be a single oxyalkylene group used alone or a combination of two or more oxyalkylene groups, and the addition form when two or more types are used in combination may be block or random. In the case where an oxyethylene group and a 1,2-oxypropylene group are used in combination, the weight ratio of the oxyethylene group to the 1,2-oxypropylene group is preferably 50:50 to 100: 0 from the viewpoint of stability over time. More preferably, it is 50: 50-70: 30. M in the general formula (1) is an average value and is a number of 1 to 60, preferably 20 to 55, more preferably 30 to 50, from the viewpoint of stability over time.

(A) can be produced by combining the following known reactions.
(1) Friedel-Crafts reaction Phenol is charged into a reactor equipped with a stirrer and a temperature control function, and styrene, benzyl chloride and / or phenethyl chloride, etc. are added by Friedel-Crafts reaction in the presence of a catalyst, styrenation, A benzylated and / or phenethylated phenol (a) is obtained. The reaction temperature is usually 50 to 150 ° C., and the reaction time is usually 2 to 10 hours. Examples of the catalyst include aluminum chloride, zinc chloride and activated clay. The amount of catalyst used is usually 0.05-2% by weight based on the weight of the phenol. After completion of the Friedel-Craft reaction, the catalyst can be removed and purified by treatment with an adsorbent.
(2) Addition reaction of alkylene oxide (a) obtained in (1) is charged into a pressurized reaction vessel, and alkylene oxide having 2 to 4 carbon atoms is blown in the absence of a catalyst or in the presence of a catalyst. Alternatively, the reaction is performed in one step or multiple steps under pressure to obtain (A). The reaction temperature is usually 50 to 150 ° C., and the reaction time is usually 2 to 20 hours. Catalysts include alkali catalysts [eg alkali metals (lithium, sodium, potassium, cesium etc.)], acids [perhalogen acids (perchloric acid, perbromic acid, periodic acid etc.), sulfuric acid, phosphoric acid and Nitric acid etc. (preferably perchloric acid)] and salts thereof [preferably salts of divalent or trivalent metals (Mg, Ca, Sr, Ba, Zn, Co, Ni, Cu, Al, etc.)]. Can be mentioned. The usage-amount of a catalyst is 0.05-2 weight% normally based on the weight of (a). After completion of the addition reaction of alkylene oxide, the catalyst can be neutralized if necessary, and treated with an adsorbent to remove and purify the catalyst.

  Specific examples of the alkylene oxide adduct of higher alcohols or the alkylene oxide adduct (B) of fats and oils having a hydroxyl group in the present invention include the following.

  Examples of the alkylene oxide adduct of higher alcohols include alkylene oxide adducts of monohydric alcohols having an alkyl or alkenyl group having 8 to 24 carbon atoms, and preferably have 8 to 16 carbon atoms from the viewpoint of stability over time. And more preferably 10 to 14 carbon atoms. Examples of the alkylene oxide include alkylene oxides having 2 to 4 carbon atoms [ethylene oxide (hereinafter abbreviated as EO), 1,2-propylene oxide (hereinafter abbreviated as PO), 1,2-butylene oxide and the like]. Of these, EO is preferred. The alkylene oxide having 2 to 4 carbon atoms may be used alone or in combination of two or more, and the addition form when using two or more in combination may be block or random. When two or more kinds of alkylene oxide are used in combination, the combination of EO and PO is preferable from the viewpoint of stability over time, and the weight ratio of EO and PO is 50:50 to 90:10. The number of moles of alkylene oxide added per mole of higher alcohol is preferably 10 to 100 moles, more preferably 15 to 80 moles, and particularly preferably 20 to 60 moles from the viewpoint of stability over time.

  Examples of the method for producing an alkylene oxide adduct of a higher alcohol include a method in which an alkylene oxide having 2 to 4 carbon atoms is added to a higher alcohol in the same manner as the method (2) in the production method (A). .

  Examples of the alkylene oxide adduct of fats and oils having a hydroxyl group include glycerin and monovalent fatty acids (8 to 24 carbon atoms) (for example, caprylic acid, 2-ethylhexanoic acid, nonanoic acid, dodecanoic acid, tetradecanoic acid, stearic acid, oleic acid). , Benzoic acid, ethyl benzoic acid, cinnamic acid, t-butyl benzoic acid and the like) mono- or diester alkylene oxide adducts, hydroxy monovalent fatty acids having 8 to 24 carbon atoms (8 to 24 carbon atoms) (for example, 2- Hydroxycaprylic acid, 2-hydroxynonanoic acid, 12-hydroxylauric acid, 4-hydroxypalmitic acid, 12-hydroxystearic acid, ricinoleic acid, ricinoelaidic acid, 2-hydroxyarachidic acid, 2-hydroxybehenic acid, 2- Hydroxytetracosenoic acid and 9,14-dihydroxystearin Alkylene oxide adduct etc.) triglyceride (castor oil and hardened castor oil, etc.). Among these, an alkylene oxide adduct of hydroxy monovalent fatty acid (8 to 24 carbon atoms) triglyceride is preferable from the viewpoint of aging stability, and an alkylene oxide adduct of castor oil or hydrogenated castor oil is more preferable. is there. Examples of the alkylene oxide include alkylene oxides having 2 to 4 carbon atoms [EO, PO, 1,2-butylene oxide and the like], and among these, EO is preferable. The alkylene oxide having 2 to 4 carbon atoms may be used alone or in combination of two or more, and the addition form when using two or more in combination may be block or random. From the viewpoint of aging stability, the number of moles of alkylene oxide added per mole of fat and oil having a hydroxyl group is preferably 10 to 100 moles, more preferably 15 to 80 moles, and particularly preferably 20 to 60 moles. is there.

  As a method for producing an alkylene oxide adduct of a fat and oil having a hydroxyl group, an alkylene oxide having 2 to 4 carbon atoms is added to the fat and oil having a hydroxyl group in the same manner as the method (2) in the production method of (A). The method of reacting is mentioned.

  Examples of the anionic surfactant (C) in the present invention include the following. Sulfosuccinic acid ester salt having a hydrocarbon group having 8 to 24 carbon atoms [mono or dialkyl (lauryl, octyl, 2-ethylhexyl, myristyl, stearyl, etc.) sulfosuccinic acid ester di or monosodium, and (poly) oxyethylene (degree of polymerization = 1 to 100) mono- or dialkyl (such as lauryl octyl, 2-ethylhexyl, myristyl, and stearyl) sulfosuccinate di- or monosodium], ether sulfate having an alkyl group having 8 to 24 carbon atoms [(poly) oxyethylene (degree of polymerization) = 1 to 100) lauryl ether sulfate sodium salt and polyoxyethylene (degree of polymerization = 1 to 50) tetradecyl ether sulfate sodium salt, etc.], sulfonate having an alkyl group having 8 to 24 carbon atoms [dodecylsulfate Sodium acetate, etc.], ether carboxylic acids having 8 to 24 carbon atoms or salts thereof [(poly) oxyethylene (degree of polymerization = 1-100) lauryl ether sodium acetate, etc.], (poly) oxyethylene ( Degree of polymerization = 1-100) Coconut oil fatty acid sodium monoethanolamide sulfate, alkyl (carbon number 6-18) benzenesulfonate, phosphate ester salt having hydrocarbon group having carbon number 8-24 [sodium lauryl phosphate and (Poly) oxyethylene (degree of polymerization = 1-100) sodium lauryl ether phosphate, etc.], and C10-18 fatty acid salts [sodium laurate, triethanolamine laurate, etc.] and the like. Among these, a sulfosuccinic acid ester salt having a hydrocarbon group having 8 to 24 carbon atoms is preferable from the viewpoint of stability over time, and a dialkylsulfosuccinic acid having a hydrocarbon group having 6 to 10 carbon atoms is more preferable. Ester salt.

  The contents of (A), (B) and (C) in the present invention are as follows. The content of (A) is preferably from 5 to 50% by weight, more preferably from 5 to 30% by weight, based on the total weight of (A), (B) and (C), from the viewpoint of stability over time. %, Particularly preferably 10 to 20% by weight. The content of (B) is preferably 10 to 60% by weight, more preferably 20 to 55% by weight from the viewpoint of stability over time, based on the total weight of (A), (B) and (C). %, Particularly preferably 30 to 40% by weight. The content of (C) is preferably 5 to 70% by weight, more preferably 20 to 65% by weight from the viewpoint of stability over time, based on the total weight of (A), (B) and (C). %, Particularly preferably 40 to 60% by weight.

  The perfume solubilizer of the present invention may further contain a nonionic surfactant (D) and / or an amphoteric surfactant (E) other than (A) and (B) if necessary. Inclusion of these surfactants improves the stability over time.

  Examples of the nonionic surfactant (D) other than (A) and (B) include the following. Fatty acid (carbon number 8-18) EO (addition mole number 1-60) adduct, polypropylene glycol (number average molecular weight 200-4,000) EO (addition mole number 1-100) adduct, polyoxyethylene (addition mole) Fatty acid (carbon number 8-24) ester EO adduct (addition) of alkyl (carbon number 6-20) allyl ether, polyvalent (2-8 valence or more) alcohol (carbon number 2-30) Mole number 1-60) [Sorbitan monolaurate EO (addition mole number 1-30) adduct, sorbitan monooleate EO (addition mole number 1-30) adduct, etc.], alkyl (carbon number 8-24) amine EO (Addition mole number 1-100) -PO (addition mole number 0-20) adduct, fatty acid (carbon number 8-24) ester of polyhydric (2-8 valence or more) alcohol (carbon number 2-30) ( Sorbitan monolaurate and sorbitan monooleate, etc.), and the like fatty acid alkanolamides (lauric acid monoethanolamide and lauric diethanolamide and the like).

  Examples of the amphoteric surfactant (E) include carboxybetaine-type amphoteric surfactants [fatty acid amidopropyldimethylaminoacetic acid betaines having 10 to 18 carbon atoms (for example, coconut oil fatty acid amidopropyl betaine), alkyl (carbon atoms 10 to 18). Dimethylaminoacetic acid betaine (for example, lauryldimethylaminoacetic acid betaine), imidazolinium type carboxybetaine (for example, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine)], sulfobetaine type amphoteric surfactant [C10-C18 fatty acid amidopropyl hydroxyethyl sulfobetaine (for example, coconut oil fatty acid amidopropyl dimethylhydroxyethyl sulfobetaine), dimethylalkyl (C10-C18) dimethyl hydroxyethyl sulfobetaine ( Lauryl hydroxy sulfo betaine) eg to amino acid type amphoteric surfactants [e.g. β- laurylamino sodium propionate, etc.] and the like.

  Although the property of the fragrance | flavor solubilizer of this invention is not specifically limited, Liquid form, paste form, gel form, powder form, flake form, block form, etc. are mentioned. Among these, liquid is preferable from the viewpoint of easy handling.

The perfume solubilizing agent of the present invention can be produced by selecting the following method depending on the difference in properties.
(1) When the properties of the fragrance solubilizer are liquid, paste or gel, (A), (B) and (C) are further added to the mixing tank equipped with a stirrer and a temperature control function, if necessary (D ) Or (E) is charged to the charging order without any particular limitation, and stirred at 30 to 80 ° C. until uniform.
(2) When the property of the fragrance solubilizing agent is in a powder form In a mixing tank equipped with a stirrer and a temperature control function, (D) or (E) ) With no particular restrictions on the order of addition, and stirring at 30 to 80 ° C. until uniform, followed by a spray dryer (for example, a pressure spray nozzle type spray dryer, a two-fluid spray nozzle type spray dryer, and a rotary disk type spray dryer) Spray drying with a machine).
(3) When the properties of the fragrance solubilizer are powder, flake and block, (A), (B) and (C) are further added to a mixing tank equipped with a stirrer and a temperature control function as necessary ( D) or (E) is charged to the charging order without any particular restriction, and stirred until it is uniformly melted at 30 to 100 ° C., then the melt is taken out on a release paper and cooled to room temperature, and the resulting solidified product is pulverized. A method of pulverizing to an appropriate size (powder, flake or block) with a mill (eg, a mill mixer, ball mill, jet mill, colloid mill, homogenizer, etc.).

  The fragrance of the present invention comprises at least one selected from the group consisting of a hydrophilic organic solvent (F), other additives (G) and water, if necessary, comprising the fragrance solubilizer and fragrance of the present invention as essential components. Containing.

  As a fragrance | flavor in this invention, a natural fragrance | flavor or a synthetic | combination fragrance | flavor is mentioned, The compound fragrance | flavor which used 2 or more types together alone may be sufficient.

  Natural fragrances include animal fragrances (eg, fragrances) and vegetable fragrances (Abies oil, Ajokun oil, almond oil, angelica root oil, paging oil, pergamot oil, perch oil, bore bellows oil, kayabuchi oil, gananga oil, capsicum Oil, caraway oil, cardamom oil, cassia oil, celery oil, cinnamon oil, citronella oil, cognac oil, coriander oil, cupebu oil, cumin oil, camphor oil, jill oil, estgolan oil, eucalyptus oil, fennel oil, garlic oil , Ginger oil, grapefruit oil, hop oil, juniper perry oil, laurel leaf oil, lemon oil, lemongrass oil, ropage oil, mace oil, nutmeg oil, mandarin oil, tangerine oil, mustard oil, peppermint oil, camellia oil, orange Oil, sage oil, star anise oil, turpentine oil and wo Muuddo oil, etc.) and the like.

  Synthetic fragrances include hydrocarbons (such as pinene, limonene, ocimene and guaien), alcohols (linalool, geraniol, citronellol, menthol, borneol, benzyl alcohol, anis alcohol, α-phenylethyl alcohol, β-phenylethyl alcohol, Rosinol, ambrinol, 1-octanol, 3-octanol, 9-decenol, 1-undecenol, dihydrocarbeveol, prenol, ethyl linalool, 3-heptanol, benzyl eugenol, 2-ethylhexanol, 3-hexenol, 2,4- Dimethyl-3-cyclohexene-1-methanol, P-isopropylcyclohexenemethanol, 1-nonanol, 2-nonanol, P-isopropylcyclohexanol, 2-methyl-3 Buten-2-ol, 2-hexenol, 1-nonen-3-ol, 3-methyl-1-pentanol and 3,4,5,6,6-pentamethyl-2-heptanol), phenols (anethole and eugenol) ), Aldehydes (n-butyraldehyde, isobutyraldehyde, hexyl aldehyde, heptyl aldehyde, n-nonyl aldehyde, nonadienal, citral, citronellal, benzaldehyde, cinnamic aldehyde, heliotropin, vanillin, 2-dodecenal, 2, 5, 6-trimethyl-4-heptanal, trimethylundecenal, 2-decenal, p-tolylaldehyde, acetaldehyde diethyl acetal, n-octanal, n-decanal, p-isopropylphenylacetaldehyde, o Tanganal dimethyl acetal, n-nonanal, undecanal, 10-undecenal, phenylpropionaldehyde, 3-hexenal, 2-undecenal and p-methylhydratropaldehyde, ketones (methyl amyl ketone, methyl nonyl ketone, diacetyl) , Acetylpropionyl, acetylbutyryl, carvone, menthone, camphor, acetophenone, p-methylacetophenone, ionone, dihydrocarvone and 2-undecanone, etc., lactone or oxides (amylbutyrolactone, ethyl methylphenylglycidate, γ-nonyl) Lactone, coumarin, cineol, jasmine lactone, methyl r-decalactone, 2,2,6-trimethyl-6-vinyltetrahydropyran and 5-isoproperol-2-methyl- -Vinyltetrahydrofuran, etc.), esters (methyl formate, isopropyl formate, linalyl formate, ethyl acetate, octyl acetate, menthyl acetate, benzyl acetate, cinnamyl acetate, butyl propionate, isoamyl acetate, isopropyl isobutyrate, iso Granyl valerate, allyl caproate, butyl heptylate, octyl caprylate, methyl heptine carboxylate, ethyl perahagonate, methyl octynecarboxylate, isoacyl caprate, methyl laurate, ethyl myristate, ethyl benzoate, benzyl benzoate , Methyl phenylacetate, butyl phenylacetate, methyl cinnamate, cinnamyl cinnamate, methyl salicylate, ethyl anisate, methyl anthranilate, ethyl pyruvate, ethyl α-butyl butyrate, decyl acetate, propyl formate, etc.).

  Examples of the hydrophilic organic solvent (F) include polyhydric alcohols having 2 to 5 carbon atoms (dihydric alcohols: ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, etc., trihydric alcohols: glycerin, etc., tetravalent alcohols: pentaerythritol. , Pentahydric alcohol: xylitol, etc.), monohydric alcohol having 2 to 6 carbon atoms (ethanol, isopropanol, butanol, 3-methyl-3-methoxybutanol, etc.), glycol ether having 3 to 20 carbon atoms (monoalkyl ether: Dialkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, ethylene glycol monobutyl ether and ethylene glycol monophenyl ether: Tylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol dimethyl ether, dipropylene glycol n-propyl methyl ether, etc.), nitrogen atom-containing hydrophilic solvents (N-methylpyrrolidone, N -Ethylpyrrolidone, 2-pyrrolidone, N-methylformamide and N, N-dimethylformamide), lactone hydrophilic solvents (propiolactone, butyrolactone, etc.), ketone hydrophilic solvents (methyl ethyl ketone, cyclohexanone, diacetone alcohol, etc.) ), Cyclic ether-based hydrophilic solvents (such as tetrahydrofuran and tetrahydropyran), esthetics It can be used the system a hydrophilic solvent (ethyl acetate, ethyl lactate, butyl lactate and ethyl acetoacetate) one or more selected from. Among these, a C2-C5 polyhydric alcohol, a C2-C6 monohydric alcohol, and a C3-C20 glycol ether are preferable. Moreover, the ratio in the case of using 2 or more types together is not specifically limited.

  Other additives (G) include alkali agents [triethanolamine, monoethanolamine, etc.], chelating agents [EDTA, NTA, etc.], antibacterial agents [isothiazoline (2-n-octyl-4-isothiazoline-3- ON, etc.), imidazoles (thiabendazole, etc.), carbanilide antibacterials (trichlorocarbanilide, etc.), triazines (debuconazole, etc.), natural (hinokitiol, etc.) and biguanides (polyhexamethylene biguanide, etc.)], coloring agents [Inorganic pigments (ultraviolet, bitumen, cobalt violet, etc.), organic pigments (red 201, red 405, blue 1, yellow 4, green 3, etc.) and natural pigments (chlorophyll, β-carotene, etc.) ] And defoamers (silicone defoamers, polyoxyalkylene defoamers and mineral oils) Foam agents, and the like) and the like.

  The contents of the fragrance solubilizer, fragrance, hydrophilic organic solvent (F), other additive (G) and water of the present invention in the fragrance of the present invention are as follows. The content of the fragrance solubilizer of the present invention is preferably 0.5 to 10% by weight, more preferably 1 to 5% by weight, based on the total weight of the fragrance. The content of the fragrance is preferably 0.5 to 5% by weight, more preferably 1 to 3% by weight, based on the total weight of the fragrance. The content of the hydrophilic organic solvent (F) is preferably 0 to 80% by weight, more preferably 0 to 60% by weight, and particularly preferably 10 to 50% by weight based on the total weight of the fragrance. is there. The content of the other additive (G) is preferably 0 to 10% by weight based on the total weight of the fragrance for the alkali agent and chelating agent, and for the antibacterial agent, colorant and antifoaming agent, Preferably it is 0 to 5% by weight based on the total weight of the fragrance. The content of water is preferably 0 to 99% by weight, more preferably 20 to 97% by weight, based on the total mass of the fragrance.

  The weight ratio of the fragrance / fragrance solubilizer in the fragrance of the present invention is preferably 5/1 to 1/5, more preferably 3/1 to 1/3.

  Although the shape of the fragrance | flavor of this invention includes liquid form, paste form, gel form, powder form, flakes, block form, etc., it is not particularly limited. From the viewpoint of ease of handling, preferred is liquid form and gel form.

  The fragrance | flavor of this invention can be manufactured by selecting the same method as the said fragrance | flavor solubilizer by the difference in a property.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to this. In the following, “parts” and “%” respectively represent “parts by weight” and “% by weight” unless otherwise specified.

<Production Example 1> [Synthesis of PO (17 mol) EO (34 mol) adduct (A-1) of styrene (1.75 mol) -modified phenol]
A glass reaction vessel equipped with a stirrer and a heating / cooling device was charged with 47 parts of phenol and 2 parts of activated clay, and heated to 125 ° C. Under stirring, 91 parts of styrene was added dropwise over 4 hours, followed by aging at 125 ° C. for 2 hours. Subsequently, the mixture was cooled to 80 ° C. with stirring and purified by filtration to obtain styrene (1.75 mol) -phenol (a-1). A metal pressure-resistant reaction vessel equipped with a stirrer, a heating / cooling device and a dropping cylinder was charged with 138 parts of (a-1) and 3 parts of potassium hydroxide, sealed with nitrogen, and heated to 130 ° C. Under stirring, 493 parts of PO was added dropwise over 6 hours, and then aged at 130 ° C. for 2 hours. Next, 748 parts of EO was added dropwise at 130 ° C. over 3 hours with stirring, and then aged at 130 ° C. for 2 hours to obtain a nonionic surfactant (A-1) having an aromatic ring [in the general formula (1) A compound in which R is an ethylidene group, n = 1.75, m = 51, and a group in which 60% of oxyethylene group and 40% of oxypropylene group are added based on the total weight of (AO) m).

<Production Example 2> [Synthesis of EO (60 mol) adduct (A-2) of styrene (3.0 mol)] phenol
Styrene (3.0 mol) phenol (a-2) was obtained in the same manner as in Production Example 1 except that 91 parts of styrene was changed to 156 parts. Next, 203 parts of (a-2) and 1 part of potassium hydroxide were charged into a metal pressure-resistant reaction vessel equipped with a stirrer, a heating / cooling device, and a dropping cylinder, sealed after nitrogen substitution, and heated to 130 ° C. Under stirring, 1320 parts of EO was added dropwise over 6 hours, and then aged at 130 ° C. for 2 hours to obtain a nonionic surfactant (A-2) having an aromatic ring [R in the general formula (1) is an ethylidene group , N = 3.0, m = 60, compound with 100% oxyethylene group based on the total weight of (AO) m].

<Production Example 3> [Synthesis of PO (20 mol) EO (26.4 mol) adduct (A-3) of styrene (1.0 mol)] phenol]
Styrene (1.0 mol) -modified phenol (a-3) was obtained in the same manner as in Production Example 1 except that 91 parts of styrene was changed to 52 parts. Subsequently, 99 parts of (a-3) and 1 part of potassium hydroxide were charged into a metal pressure-resistant reaction vessel equipped with a stirrer, a heating / cooling device, and a dropping cylinder, sealed after nitrogen substitution, and heated to 130 ° C. Under stirring, 580 parts of PO was added dropwise over 6 hours, and then aged at 130 ° C. for 2 hours. Subsequently, EO 580 parts was dripped at 130 degreeC over 3 hours, Then, it age | cure | ripened at 130 degreeC for 2 hours, and the nonionic surfactant (A-3) which has an aromatic ring was obtained [in General formula (1) Compound in which R is an ethylidene group, n = 1.0, m = 46.4, and a group in which 50% oxyethylene group and 50% oxypropylene group are added based on the total weight of (AO) m}.

<Production Example 4> [Synthesis of decyl alcohol PO (5 mol) EO (14 mol) adduct (B-1)]
A metal pressure-resistant reaction vessel equipped with a stirrer, a heating / cooling device and a dropping cylinder was charged with 158 parts of decyl alcohol and 2 parts of potassium hydroxide, sealed with nitrogen, and heated to 130 ° C. Under stirring, 290 parts of PO was added dropwise over 6 hours, and then aged at 130 ° C. for 2 hours. Next, 616 parts of EO was added dropwise with stirring at 130 ° C. over 3 hours, and then aged at 130 ° C. for 2 hours to obtain a PO (5 mol) EO (14 mol) adduct (B-1) of decyl alcohol.

<Production Example 5> [Synthesis of stearyl alcohol PO (2 mol) EO (24 mol) adduct (B-2)]
A metal pressure-resistant reaction vessel equipped with a stirrer, a heating / cooling device and a dropping cylinder was charged with 270 parts of stearyl alcohol and 2 parts of potassium hydroxide, sealed with nitrogen, and heated to 130 ° C. Under stirring, 116 parts of PO was dropped over 6 hours, and then aged at 130 ° C. for 2 hours. Next, 1056 parts of EO was added dropwise with stirring at 130 ° C. over 3 hours, followed by aging at 130 ° C. for 2 hours to obtain PO (2 mol) EO (24 mol) adduct (B-2) of stearyl alcohol.

<Production Example 6> [Synthesis of PO (10 mol) EO (13.2 mol) adduct (B-3) of dodecyl alcohol]
A metal pressure-resistant reaction vessel equipped with a stirrer, a heating / cooling device and a dropping cylinder was charged with 186 parts of dodecyl alcohol and 2 parts of potassium hydroxide, sealed with nitrogen, and heated to 130 ° C. Under stirring, 580 parts of PO was added dropwise over 6 hours, and then aged at 130 ° C. for 2 hours. Next, 580 parts of EO was added dropwise with stirring at 130 ° C. over 3 hours, and then aged at 130 ° C. for 2 hours to obtain a PO (10 mol) EO (13.2 mol) adduct (B1-3) of dodecyl alcohol. .

<Production Example 7> [Synthesis of castor oil (EO) 40 mol adduct (B-4)]
A reaction vessel similar to Production Example 4 was charged with 523 parts of castor oil (hydroxyl value: 161) and 0.3 part of potassium hydroxide, sealed with nitrogen, and heated to 160 ° C. Under stirring, 880 parts of EO was added dropwise over 4 hours, and then aged at 160 ° C. for 3 hours to obtain a castor oil (EO) 40 mol adduct (B-4).

<Production Example 8> [Synthesis of castor oil (EO) 100 mol adduct (B-5)]
A castor oil (EO) 100 mol adduct (B-5) was obtained in the same manner as in Production Example 6 except that the number of EO parts was changed from 880 parts to 2200 parts.

<Production Example 9> [Synthesis of castor oil (EO) 10 mol adduct (B-6)]
A castor oil (EO) 10-mole adduct (B-6) was obtained in the same manner as in Production Example 6 except that 880 parts of EO were changed to 220 parts.

<Examples 1-18 and Comparative Examples 1-3>
The raw materials for the fragrance solubilizers in the number of parts listed in Table 1 were charged into a mixing tank equipped with a stirrer and a temperature control function, and stirred at 20 to 30 ° C. for 1 hour to give fragrance solubilizers (Examples 1 to 18). And Comparative Examples 1 to 3) were prepared.

The compositions of (C-1), (C-2), (D-1) and (E-1) in Table 1 are as follows.
(C-1): Dioctyl sulfosuccinate sodium salt “Sanmorin OT-70” [manufactured by Sanyo Chemical Industries, Ltd.]
(C-2): Lauryl alcohol sulfate triethanolamine salt “Sandet LTD” [manufactured by Sanyo Chemical Industries, Ltd.]
(D-1): Sorbitan monooleate (EO) 20 mol adduct “Ionet T-80V” [manufactured by Sanyo Chemical Industries, Ltd.]
(E-1): Palm oil fatty acid amidopropyl betaine “Lebon 2000” [manufactured by Sanyo Chemical Industries, Ltd.]

  A fragrance is prepared by the following method using the fragrance solubilizers of Examples 1 to 18 and Comparative Examples 1 to 3, and the appearance immediately after the preparation of the fragrance and the daily stability of the fragrance are evaluated by the following method. did. The results are shown in Tables 1 and 2.

<Production of fragrance>
In a 200 ml beaker, put 1.5 g of the following fragrance, 1.5 g of 3-methyl-3-methoxybutanol and 2.0 g of fragrance solubilizer, and gradually add 95.0 g of water while stirring with a magnetic stirrer at room temperature. A liquid fragrance was prepared.
Fragrance A: Lavender (Guyen)
Fragrance B: Citrus (orange oil)
Fragrance C: Floral (Oshimen)

<Appearance evaluation immediately after preparation of fragrance>
About the fragrance | flavor produced with the said method, the external appearance of the fragrance | air_condition immediately after preparation was observed visually, and the stability over time was evaluated on the following criteria.
◎: Transparent uniform liquid ○: Slightly hazy △: Dark haze X: Cloudy or separated into two layers

<Evaluation of daily stability of fragrance>
Appearance of the fragrance after leaving the fragrance prepared by the above method in a thermostatic bath at 5 ° C., 25 ° C., and 40 ° C. for 1 month, and a cycle test (from 25 ° C. to −10 ° C. over 6 hours) After cooling to −10 ° C. for 30 hours, heated from −10 ° C. to 25 ° C. over 6 hours and then held at 25 ° C. for 30 hours.This cycle is repeated 10 times.) It was observed visually and the stability over time was evaluated according to the same criteria as the appearance evaluation immediately after the preparation of the fragrance.

  As is clear from the results in Table 1, the fragrance solubilizing agent of the present invention is superior in solubilizing ability to various fragrances as compared with the fragrance solubilizing agent of the comparative example, and various temperatures (5, 25). , 40 ° C.) and −10 ° C. and 25 ° C., and after standing for 1 month, it is a transparent uniform liquid or slightly hazy, and has excellent stability over a wide range of temperatures.

  The perfume solubilizer of the present invention can also be used as a solubilizer for oily ingredients other than perfume, such as cosmetic raw materials (various vegetable oils and animal fats, etc.) and pharmaceutical raw materials. Moreover, the fragrance | flavor using the fragrance | flavor solubilizer of this invention is suitable as a fragrance | flavor especially for rooms, toilets, and cars.

Claims (8)

A nonionic surfactant (A) represented by the general formula (1), an alkylene oxide adduct of a higher alcohol or an alkylene oxide adduct (B) of a fat or oil having a hydroxyl group, and an anionic surfactant (C) A perfume solubilizing agent.

[Wherein n is a number of 1.0 to 3.0, n Rs are each independently a methylene group, ethylene group or ethylidene group, A1O is an oxyalkylene group having 2 to 4 carbon atoms, and m is an average value. And represents a number from 1 to 60. ] (AO) _m in the general formula (1) is composed of an oxyethylene group alone or an oxyethylene group and a 1,2-oxypropylene group, and the weight ratio of the oxyethylene group to the 1,2-oxypropylene group is 50: The fragrance | flavor solubilizer of Claim 1 which is 50-100: 0.   The alkylene oxide adduct of the higher alcohol is an ethylene oxide and propylene oxide adduct of a monohydric alcohol having 8 to 24 carbon atoms, and the weight ratio of ethylene oxide to propylene oxide is 50:50 to 90:10. 3. A fragrance solubilizer according to 1 or 2.   The fragrance | flavor solubilizer in any one of Claims 1-3 whose alkylene oxide adduct of the fats and oils which have the said hydroxyl group is an ethylene oxide 10-100 mol addition product of castor oil or hydrogenated castor oil.   The fragrance solubilizer according to any one of claims 1 to 4, wherein the anionic surfactant (C) is a sulfosuccinic acid ester salt having a hydrocarbon group having 8 to 24 carbon atoms.   Based on the total weight of (A), (B) and (C), (A) is contained in an amount of 5 to 50 wt%, (B) is contained in an amount of 10 to 60 wt%, and (C) is contained in an amount of 5 to 70 wt% The fragrance | flavor solubilizer in any one of Claims 1-5 formed.   Furthermore, the fragrance | flavor solubilization in any one of Claims 1-6 formed by containing nonionic surfactant (D) other than said (A) and (B), and / or an amphoteric surfactant (E). Agent.   The fragrance | flavor formed by containing the fragrance | flavor solubilizer and fragrance | flavor in any one of Claims 1-7.