JP2008149218A - Oil-in-water type emulsion - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an oil-in-water type emulsion with excellent emulsion stability and low viscosity, and an efficient production method thereof. <P>SOLUTION: The oil-in-water type emulsion is formed by emulsifying a hydrophobic compound (a) with a polymer compound b having a group represented by the following formula (1) in at least side chains, and contains water soluble sugars c in the water phase, with a water content of 40-90 mass%. The production method of the oil-in-water type emulsion comprises a process of mixing the oil-in-water type emulsion formed by emulsifying the hydrophobic compound (a) with the polymer compound b with water soluble sugars c. The hydrophobic compound formula is -(OX)<SB>n</SB>-E<SP>2</SP>-R (1), where X is a 1-6C bivalent saturated hydrocarbon group; n is a figure of 5-300; E<SP>2</SP>is an ether bond or an oxycarbonyl group; R is a 4-30C alkyl group which may be substituted with a hydroxyl group. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a low-viscosity oil-in-water emulsion and a method for producing the same.

It is an important technique in the fields of cosmetics, fragrances, and softeners for clothing to stably blend hydrophobic compounds such as oils as emulsions.
In particular, it is known that when a large amount of surfactant such as a detergent is present, stability is lost and emulsion breakage occurs. Therefore, by preparing a specific composition containing a polymer compound having a specific group in a part of the side chain and a hydrophobic compound and diluting with water, an oil-in-water emulsion of a hydrophobic compound having good stability Is known to be obtained (see, for example, Patent Document 1).
In this method, the viscosity of the resulting oil-in-water emulsion tends to be high, so water and water components such as water and water-soluble polyol are added and diluted to reduce the viscosity. Reduction technology was not known. For this reason, even when it is desired to suppress the concentration of water or water-soluble polyol, there is a problem that it is necessary to add a large amount of them for viscosity adjustment.

JP 2005-314244 A

  An object of the present invention is to provide an oil-in-water emulsion excellent in emulsion stability and having a low viscosity, and an efficient production method thereof.

The present inventors have found that when a water-soluble saccharide is added to an oil-in-water emulsion obtained by emulsifying a hydrophobic compound with a polymer compound having a specific group in a part of the side chain, the viscosity thereof is greatly reduced. It was.
That is, the present invention provides the following [1] and [2].
[1] An oil-in-water emulsion obtained by emulsifying a hydrophobic compound (a) with a polymer compound (b) having a group represented by the following formula (1) in at least a side chain, An oil-in-water emulsion containing a water-soluble saccharide (c) and having a water content of 40 to 90% by mass.
^{_{- (OX) n -E 2 -R}} (1)
(Wherein x is the same or different divalent saturated hydrocarbon group having 1 to 6 carbon atoms, n is a number of 5 to 300, E ² is an ether bond or an oxycarbonyl group, and R is a hydroxyl group. And an optionally substituted alkyl group having 4 to 30 carbon atoms.)
[2] An oil-in-water emulsion obtained by emulsifying (a) a hydrophobic compound with (b) a polymer compound having a group represented by the above formula (1) at least in the side chain; The manufacturing method of the oil-in-water emulsion which mixes with a property sugar.

  ADVANTAGE OF THE INVENTION According to this invention, it is excellent in emulsification stability and can provide the low-viscosity oil-in-water emulsion and its efficient manufacturing method.

The oil-in-water emulsion of the present invention is an oil-in-water emulsion obtained by emulsifying a hydrophobic compound (a) with a polymer compound (b) having a group represented by the formula (1) in at least a side chain. The water phase contains a water-soluble saccharide (c) and the water content is 40 to 90% by mass.
Next, each component used for the oil-in-water emulsion of this invention is demonstrated.

[Hydrophobic compound (a)]
There is no restriction | limiting in particular in the hydrophobic compound (a) used for this invention, For example, a higher alcohol, sterols, silicones, a fluorine-type oil agent, a fragrance | flavor, and other oily components can be mentioned preferably.
As the higher alcohols, linear or branched saturated or unsaturated aliphatic alcohols having 6 to 25 carbon atoms, araliphatic alcohols, and the like are used. Examples of such higher alcohols include lauryl alcohol. And myristyl alcohol, cetyl alcohol, isocetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, 2-octyldodecanol, benzyl alcohol, phenethyl alcohol, cinnamyl alcohol, and the like. Of these higher alcohols, cetyl alcohol and stearyl alcohol are preferred.
Examples of the sterols include cholesterol, cholesteryl isostearate, provitamin D ₃ , camsterol, stegmasteranol, and cholesteryl alkenyl succinate (Japanese Patent Laid-Open No. 5-294899). Among these, cholesterol, cholesteryl isostearate, and cholesteryl alkenyl succinate are particularly preferable.

As silicones, those usually blended in toiletry products can be used. For example, octamethylpolysiloxane, methylpolysiloxane, dimethylpolysiloxane, highly polymerized methylpolysiloxane, methylphenylpolysiloxane, methylpolycyclosiloxane such as octamethylcyclotetrasiloxane, trimethylsiloxysilicic acid, and alkyl modification Silicone, aralkyl modified silicone, polyether modified silicone, polyether alkyl modified silicone, amino modified silicone, fluorine modified silicone, alkyl glyceryl ether modified silicone, fatty acid ester modified silicone, fluoroalkyl modified silicone, epoxy modified silicone, carboxyl modified silicone, Methacryl modified silicone, alcohol modified silicone, mercapto modified silicone, vinyl modified silicone, JP Modified silicone modified organopolysiloxanes of JP 6-72851 and the like.
Further, as the fluorinated oil agent, perfluoropolyether, which is a perfluoro organic compound that is liquid at room temperature, or fluorine-modified silicone is preferable. For example, perfluorodecalin, perfluorooctane, perfluorononane, perfluoropentane, perfluoropolyether. Etc.

  As a fragrance | flavor, all of a natural fragrance | flavor, a synthetic | combination fragrance | flavor, and a compound fragrance | flavor can be used. Examples of natural and synthetic fragrances include cineole, camphor, pinene, limonene, terpineol, linalool, linalool acetate, nerol, neryl acetate, carvacrol, thymol, citronellol, citral, geraniol, santalol, borneol, carvone, methylionone, salicylic acid. Hexyl, Ionone, Hedion, Phenoxyethanol, Ambercore, Cedrylmethyl ether, Cynamic aldehyde, Benzyl acetate, Eugenol, Cedrene, Bornyl acetate, Menthol, Mentone, Methylchavicol, Cymen, Pregol, Anethole, Chillon, Labandurol, Sage oil, thyme oil, basil oil, peppermint oil, peppermint oil, rosemary oil, eucalyptus oil, macro ® rum oil sage, citronella oil, cedarwood oil, sweet orange oil, bergamot oil, lavender oil, cinnamic Mont oil, lemon oil, lime oil, cypress oil, and the like.

  Formulated fragrances include citrus type bases such as lemon, lime, orange, sweet orange, mandarin, and bergamot, petit gren, neroli, lemongrass, aggluten and other fresh type bases, apple, Fruity type base such as peach tone, strawberry tone, coconut tone, pineapple tone, raspberry tone, watermelon tone, rose tone, jasmine tone, mugue tone, lilac tone, carnation tone, hyacinth tone, tuberose tone, gardenia tone, mimosa tone , Narciss, Violet, Iran, Floral Bouquet, etc., Cinnamon Bark, Cinnamon Leaf, Clove, Pimentoberry, Nutmeg, Pepper, Cardamom, Coriander, Cumin, etc. Pissy type base, wood type such as cedarwood, vetiver, sandalwood, guaiac wood, woody bar, woody, etc. Leather type such as smoky, quinoline, vanilla, tonka, honey , Pure balsam-like sweet type base, other aldehydic type base, amber type base, animal type base, anise type base, aromatic herbal type base, agar type base, aqua type base, camphor cineall type base, green type Base, seed type base, herb type base, pine type base, patchouli type base, balsamic type base, mint type base, musk type base, moss type base, Vendor type base, linalool type base include resin type base, or the like.

As the other oil component, either volatile or non-volatile can be used. For example, hydrocarbons such as solid or liquid paraffin, petrolatum, crystal oil, squalane; eucalyptus oil, peppermint oil, sunflower oil, beef tallow, olive oil, carnauba wax, glycerin monostearate, glyceryl distearate, isopropyl palmitate Butyl stearate, neopentyl glycol dicaprate, diethyl phthalate, myristyl lactate, diisopropyl adipate, cetyl myristate, 1-isostearoyl-3-myristoyl glycerol, myristate-2-octyldodecyl, di-2-ethylhexane Ester oils such as acid neopentyl glycol, glycerol triisostearate, di-paramethoxycinnamic acid-glyceryl mono-2-ethylhexanoate; stearic acid, palmitic acid, Higher fatty acids such as maleic acid; lignans, vitamin E, oil-soluble vitamin C, vitamin A derivatives, ceramides, ceramide-like structure materials, the functional oil substances such as oil-soluble ultraviolet absorbers, and the like.
The said hydrophobic compound (a) can be used individually or in combination of 2 or more types.

[Polymer Compound (b)]
In the present invention, the polymer compound (b) used for emulsifying the hydrophobic compound (a) has a group represented by the following formula (1) at least in the side chain.
^{_{- (OX) n -E 2 -R}} (1)
In formula (1), n X represents the same or different divalent saturated hydrocarbon group having 1 to 6 carbon atoms. X may be linear, branched or cyclic. Specific examples of X include a methylene group, an ethylene group, a propylene group, a trimethylene group, various butylene groups, various pentylene groups, various hexylene groups, various cyclopentylene groups, various cyclohexylene groups, and the like. Then, a C2-C4 alkylene group is preferable and an ethylene group is more preferable.
n shows the number of 5-300, 5-200 are preferable and 8-120 are more preferable.
E ² represents an ether bond or an oxycarbonyl group (—OCO— or —COO—). In the oxycarbonyl group, the atom bonded to R may be a carbon atom or an oxygen atom.
R represents an alkyl group having 4 to 30 carbon atoms which may be substituted with a hydroxyl group. R may be linear, branched or cyclic, but is preferably an alkyl group having 6 to 25 carbon atoms. Specific examples of R include various hexyl groups, octyl groups, decyl groups, dodecyl groups, tetradecyl groups, hexadecyl groups, octadecyl groups, icosyl groups, and cyclohexyl groups in which an alkyl group may be introduced on the ring, Examples include a cyclooctyl group and the like, and a group in which at least one hydrogen atom of these groups is substituted with a hydroxyl group.

  Preferred examples of the polymer compound (b) include a polysaccharide derivative (b-1) having a group represented by the formula (1) and / or a group represented by the formula (1) as a main chain constituent monomer. Mention may be made, for example, of water-soluble synthetic polymer compounds (b-2) having a weight average molecular weight of 10,000 to 2,000,000 having an average of 0.0001 to 0.1 per unit.

<Polysaccharide derivative (b-1)>
As the polysaccharide derivative, a polysaccharide derivative in which part or all of the hydrogen atoms of the hydroxy group of the polysaccharide or derivative thereof are substituted with the following group (A) (hereinafter referred to as polysaccharide derivative (b-1-a)) is preferable. .
(A) the general formula (2) a group represented by _{^{-E 1 - (OX) n1 -E}} 2 -R (2)
(In the formula, E ¹ represents a linear, branched or cyclic divalent saturated hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxy group or an oxo group, and n1 represents 8 to 300. X, E ² and R have the same meaning as described above, and n1 Xs may be the same or different.)
Examples of the polysaccharides or derivatives thereof include cellulose, guar gum, starch, pullulan, dextran, fructan, mannan, agar, carrageenan, chitin, chitosan, pectin, alginic acid, hyaluronic acid and other polysaccharides; these include methyl group, ethyl group , Derivatives substituted with a hydroxyethyl group, a hydroxypropyl group, and the like. These substituents can be substituted singly or in combinations of constituent monosaccharide residues.

Specific examples of polysaccharide derivatives include hydroxyethyl cellulose, hydroxyethyl ethyl cellulose, hydroxyethyl guar gum, hydroxyethyl starch, methyl cellulose, methyl guar gum, methyl starch, ethyl cellulose, ethyl guar gum, ethyl starch, hydroxypropyl cellulose, hydroxypropyl guar gum, hydroxy Examples include propyl starch, hydroxyethyl methylcellulose, hydroxyethyl methyl guar gum, hydroxyethyl methyl starch, hydroxypropyl methyl cellulose, hydroxypropyl methyl guar gum, hydroxypropyl methyl starch and the like.
Among these polysaccharides or derivatives thereof, cellulose, starch, hydroxyethyl cellulose, methyl cellulose, ethyl cellulose, and hydroxypropyl cellulose are preferable, and hydroxyethyl cellulose is particularly preferable.
The weight average molecular weight of these polysaccharides or derivatives thereof is preferably 10,000 to 10,000,000, more preferably 100,000 to 5,000,000, still more preferably 200,000 to 2,000,000.

In the group (A), E ¹ is preferably a linear or branched divalent saturated hydrocarbon group having 2 or 3 carbon atoms which may be substituted with a hydroxy group or an oxo group. Preferable examples thereof include ethylene, propylene, trimethylene, 2-hydroxytrimethylene, 1-hydroxymethylethylene, 1-oxoethylene, 1-oxotrimethylene, 1-methyl-2-oxoethylene and the like.
X is preferably a linear or branched divalent saturated hydrocarbon group having 2 or 3 carbon atoms, specifically ethylene, propylene and trimethylene.
The average number of added moles of (—OX—) represented by n1 is preferably 8 to 120, more preferably 10 to 60, from the viewpoint of thickening effect and emulsion stability. The n1 Xs may be the same or different. E ² is an ether bond or an oxycarbonyl group, and an ether bond is preferred. R is preferably a linear or branched alkyl group having 5 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, which may be substituted with a hydroxy group, and from the viewpoint of stability. An unsubstituted alkyl group, particularly an unsubstituted linear alkyl group is preferred. Specifically, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, isostearyl group and the like are preferable.

The degree of substitution with the group (A) in the polysaccharide derivative (b-1-a) is preferably 0.0001 to 1.0, more preferably 0.0005 to 0.5, and still more preferably per constituent monosaccharide residue. Is 0.001 to 0.1.
In addition to the group (A), the polysaccharide derivative (b-1) in the present invention may be further substituted with one or more groups selected from the following groups (B), (C) and (D). Moreover, the hydrogen atom of the hydroxy group of group (A)-(D) may be further substituted by group (A)-(D).
(B) a C1-C5 sulfoalkyl group which may be substituted with a hydroxy group or a salt thereof (C) a C2-C6 carboxyalkyl group which may be substituted with a hydroxy group or a salt thereof (D ) Group represented by general formula (3)

(In the formula, D ¹ represents a linear or branched divalent saturated hydrocarbon group having 1 to 6 carbon atoms which may be substituted with a hydroxy group, and R ¹ , R ² and R ³ are the same. Alternatively, it represents a linear or branched alkyl group having 1 to 3 carbon atoms which may be substituted with a hydroxy group, and Y ⁻ represents a hydroxy ion, a halogen ion or an organic acid ion.
Examples of the group (B) include a 2-sulfoethyl group, a 3-sulfopropyl group, a 3-sulfo-2-hydroxypropyl group, and a 2-sulfo-1- (hydroxymethyl) ethyl group. From the viewpoint of production, a 3-sulfo-2-hydroxypropyl group is preferable. All or a part of these groups (B) may be a salt with an alkali metal such as Na, K, Ca, Mg or an alkaline earth metal, an amine, an organic cation such as ammonium.
The degree of substitution with the group (B) is preferably 0 to 1.0, more preferably 0 to 0.8, and still more preferably 0 to 0.5 per constituent monosaccharide residue.

Examples of the group (C) include a carboxymethyl group, a carboxyethyl group, a carboxypropyl group, a carboxybutyl group, and a carboxypentyl group. Among these, a carboxymethyl group is preferable from the viewpoints of stability and production. All or part of the group (C) may be a salt with an alkali metal such as Na, K, Ca, Mg or an alkaline earth metal, an amine, an organic cation such as ammonium.
The degree of substitution with the group (C) is preferably 0 to 1.0, more preferably 0 to 0.8, and particularly preferably 0 to 0.5 per constituent monosaccharide residue.

D ¹ in the group (D) is preferably a linear or branched divalent saturated hydrocarbon group which may be substituted with a hydroxy group having 2 or 3 carbon atoms. Specifically, ethylene, propylene, trimethylene, 2-hydroxytrimethylene, 1-hydroxymethylethylene and the like are preferable.
Examples of R ¹ , R ^2, and R ³ include a methyl group, an ethyl group, a propyl group, and a 2-hydroxyethyl group, and among them, a methyl group and an ethyl group are preferable.
Among Y ⁻ , halogen ions include chlorine ions, bromine ions, iodine ions, and organic acid ions include CH ₃ COO ⁻ , CH ₃ CH ₂ COO ⁻ , and CH ₃ (CH ₂ ) ₂ COO ^−. Can be mentioned. Y ^- The hydroxy ion, chloride ion and bromide ion are preferred.
The degree of substitution with the group (D) is preferably 0 to 0.5, particularly preferably 0 to 0.3 per constituent monosaccharide residue.

The substitution of the polysaccharide or its derivative with the groups (A) to (D), that is, polyoxyalkyleneation, sulfoalkylation, carboxyalkylation or cationization can be carried out by the method described in WO00 / 73351.
The polysaccharide derivative (b-1) used in the present invention is exemplified by the following general formula (4) when a cellulose or a derivative thereof is used as an example.

(In the formula, R ⁴ represents a hydrogen atom, a methyl group, an ethyl group, a hydroxyethyl group, a hydroxypropyl group, a group selected from the above group (A), group (B), group (C) and group (D)). , Q represents an alkylene group having 2 to 4 carbon atoms, a, b and c are the same or different and each represents a number of 0 to 10, QO group, R ⁴ group, a, b and c are repeating Within a unit or between repeating units, they may be the same or different, and the hydroxy groups of the groups (A) to (D) may be further substituted with other groups (A) to (D), provided that the molecule At least one of R ^{4 in} the group is a group (A).)

<Water-soluble synthetic polymer compound (b-2)>
The water-soluble synthetic polymer compound is a compound having a molecular weight of 10,000 to 2,000,000 having an average of 0.0001 to 0.1 group of the formula (1) per main chain constituting monomer unit.
As the group of formula (1), X is an ethylene group, n is a number of 5 to 200, and R is a linear, branched or cyclic alkyl group having 4 to 30 carbon atoms. Further, the average number of groups of the formula (1) is more preferably 0.001 to 0.05 on average per main chain constituting monomer unit, and the weight average molecular weight is more preferably 30,000 to 1,500,000.

The water-soluble synthetic polymer compound can be obtained by reacting a compound represented by the general formula (5) with a water-soluble synthetic polymer compound having a hydroxyl group such as polyvinyl alcohol and polyglycidol.
E ^3- (OX) _n -E ² -R (5)
(In the formula, E ³ represents an epoxidized alkyl group having 3 to 6 carbon atoms, a linear or branched halogenated alkyl group having 1 to 6 carbon atoms which may be substituted by a hydroxy group, a carboxy group, and carbon. number 2-6 carboxyalkyl group, or a derivative thereof, X, n, R and E ² are as defined above.)
It can also be obtained by copolymerizing a water-soluble monomer and a monomer having a hydrophobic group having 4 to 30 carbon atoms via a 5-200 oxyethylene (EO) linking chain.
As said water-soluble monomer, the compound represented by General formula (6) or the compound represented by General formula (7) is mentioned.

(In the formula, R ⁵ , R ⁶ and R ⁷ are the same or different and each represents a hydrogen atom or a methyl group, and x represents an average of 2 to 100.)

(Wherein R ⁸ and R ⁹ are the same or different and represent a hydrogen atom or a methyl group, R ¹⁰ and R ¹¹ represent a methyl group or an ethyl group, y represents 0 or an integer of 2 to 5, and Z represents —N (R ¹² ) — group (R ¹² represents a hydrogen atom or a methyl group), an oxygen atom or a direct bond.
Specific examples thereof include methoxypolyethylene glycol monomethacrylate, methoxypolyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polyethylene glycol monoacrylate, N, N-dimethylaminoethyl acrylate, N, N-dimethylaminopropylacrylamide, N, N -Dimethylacrylamide and the like, and these compounds can be synthesized by known methods.

  Examples of the monomer having a hydrophobic group having 4 to 30 carbon atoms via 5 to 200 EO linking chains include compounds represented by the general formula (8).

Wherein R ¹³ and R ¹⁴ are the same or different and each represents a hydrogen atom or a methyl group, z represents a number of 5 to 200, R ¹⁵ has 4 to 30 carbon atoms which may be substituted with a hydroxy group, Preferably 8-30 linear, branched or cyclic alkyl groups are shown.)
Specific examples include lauroxy polyethylene glycol monoacrylate, stearoxy polyethylene glycol monomethacrylate and the like, and these compounds can be synthesized by known methods.

  In the oil-in-water emulsion of the present invention, the hydrophobic compound (a) is first emulsified with the polymer compound (b) to prepare an oil-in-water emulsion. There is no restriction | limiting in particular in an emulsification processing method, The conventionally well-known method using a homogenizer etc. is employable. Next, by adding the water-soluble saccharide (c) to this oil-in-water emulsion, an oil-in-water emulsion having excellent emulsion stability and low viscosity containing the water-soluble saccharide in the aqueous phase can be obtained. it can.

[Water-soluble saccharide (c)]
The water-soluble saccharide (c) is not particularly limited, and examples thereof include glucose, fructose, lactose, maltose, sucrose, dextrin, cyclodextrin, maltose, fructose, pullulan, and sugar alcohols such as sorbitol and mannitol. Among these, from the viewpoints of solubility and a viscosity reducing effect, it is particularly preferable to use dextrin which is a starch degradation product.
Dextrin is a group of intermediate products produced when starch is partially hydrolyzed by the action of acid, enzyme, heat, etc., and has various degrees of polymerization from high molecular weight compounds with many glucose linkages to oligosaccharides. Of the compound. Types include white dextrin, yellow dextrin, British gum and the like, and any of them can be used.
The water-soluble saccharide (c) can be used alone or in combination of two or more.

[Other ingredients]
In the oil-in-water emulsion of the present invention, a water-soluble polyol or the like can be blended within a range that does not impair the object of the present invention. The water-soluble polyol is a polyhydric alcohol having two or more hydroxyl groups in the molecule. Specific examples thereof include alkylene glycols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, Examples include polyalkylene glycols such as dipropylene glycol, sugar alcohols such as glucose, maltose, maltose, sucrose, fructose, xylitol, maltotriose, and threitol, glycerin, polyglycerin, erythritol, and amylolytic reducing alcohol.

In the oil-in-water emulsion of the present invention, the water content is 40 to 90% by mass, preferably 50 to 80% by mass. When the water content is within this range, an oil-in-water emulsion having good emulsion stability and a desired low viscosity can be obtained.
Moreover, about content of hydrophobic compound (a), a high molecular compound (b), and water-soluble saccharides (c), from a viewpoint of obtaining an oil-in-water emulsion with favorable emulsion stability, hydrophobic compound (a) Is preferably 1 to 50 mass%, the content of the polymer compound (b) is preferably 0.01 to 10 mass%, and the content of the hydrophobic compound (a) is 4 to 30 mass%, The content of the polymer compound (b) is more preferably 0.05 to 5% by mass.
On the other hand, the content of the water-soluble saccharide (c) is preferably 8 to 50% by mass and more preferably 15 to 40% by mass from the viewpoints of the viscosity reducing effect and the emulsion stability.
In the oil-in-water emulsion of the present invention, the average particle size of the emulsified particles is preferably 0.1 to 8 μm, more preferably 0.3 to 6 μm, and 0.5 to 5 μm. Is more preferable. The average particle size of the emulsified particles is a value obtained by measuring the particle size distribution by laser scattering, and specifically measured by the method described in the examples.

[Method for producing oil-in-water emulsion]
In the method for producing an oil-in-water emulsion of the present invention, the hydrophobic compound (a) is emulsified with a polymer compound (b) having a group represented by the formula (1) in at least a side chain. The oil-type emulsion and the water-soluble saccharide (c) are mixed.
As a method for producing an oil-in-water emulsion, a homogenizer is used,
(I) Hydrophobic compound (a) and polymer compound (b) are stirred and mixed, then water is added and stirred to obtain an oil-in-water emulsion, and then water-soluble saccharide (c) is added thereto To stir and
(Ii) Hydrophobic compound (a), polymer compound (b), and a part of water are stirred and mixed, and then the remaining water is added and stirred to obtain an oil-in-water emulsion. (C) a method of adding and stirring; and (iii) the hydrophobic compound (a), the polymer compound (b), and the total amount of water are stirred and mixed to obtain an oil-in-water emulsion, and then water-soluble. A method of adding the saccharide (c) and stirring can be employed.
Alternatively, a method in which the hydrophobic compound (a), the polymer compound (b), and the water-soluble saccharide (c) are stirred and mixed, then water is added and stirred to obtain an oil-in-water emulsion can be used.
Among these methods, the method (i) is preferable from the viewpoint of obtaining an oil-in-water emulsion having a reduced viscosity with good emulsion stability.
When the water-soluble saccharide (c) is added to the obtained oil-in-water emulsion, the water-soluble saccharide (c) may be added in the form of an aqueous solution by dissolving in a part of the water used, You may add without adding water. Thus, an oil-in-water emulsion with reduced viscosity, in which the content of the hydrophobic compound (a), the polymer compound (b), the water-soluble saccharide (c) and the water are in the above ranges, respectively. Can be manufactured.

In the oil-in-water emulsion of the present invention, various additives such as a surfactant, a dispersant, a solvent, a fragrance, a colorant, an inorganic salt, an antiseptic, as long as the effects of the present invention are not impaired. An antioxidant, a pH adjuster, etc. can be contained.
The oil-in-water emulsion of the present invention has good emulsification stability and low viscosity, and is suitably used, for example, in the detergent field, cosmetic field, skin care agent field, clothing treatment field, and perfume field. .

Various characteristics of the oil-in-water emulsions obtained in Examples and Comparative Examples were determined by the following methods.
(1) Emulsified state 1 g of the emulsified immediately after being obtained is diluted in 9 g of ion-exchanged water, put on a preparation, and put into an appropriate amount. Was observed.
(2) Average emulsified particle size The average particle size of the emulsified particles in the emulsified product is 0.5 g of the emulsified product in physiological saline using a laser scattering / particle size distribution measuring device “LA-910” manufactured by Horiba, Ltd. It diluted with 99.5g and measured at room temperature.
(3) Viscosity Using a B-type viscometer, No. 4 rotor and no. Using two rotors, measurement was performed under the conditions of 25 ° C., 60 rpm, and 1 minute.

Production Example 1 (Production of polysaccharide derivative)
A slurry liquid was prepared by mixing 80 g of hydroxyethyl cellulose having a weight average molecular weight of about 800,000 and a hydroxyethyl group substitution degree of 1.8 (HEC-QP15000H, manufactured by Union Carbide), 640 g of isopropyl alcohol and 2.0 g of p-toluenesulfonic acid. Prepared and stirred for 30 minutes at room temperature under nitrogen atmosphere. To this solution, 15 g of the compound represented by formula (9) was added and reacted at 80 ° C. for 8 hours for polyoxyalkyleneation.

After completion of the reaction, the reaction solution was neutralized with a 48 mass% aqueous sodium hydroxide solution, and the reaction product was filtered off. The reaction product was washed twice with 500 g of 80% by mass of isopropyl alcohol and twice with 500 g of isopropyl alcohol, and dried under reduced pressure at 70 ° C. overnight to obtain 73.4 g of polyoxyalkylenated hydroxyethyl cellulose (polysaccharide derivative). The degree of substitution of the group (A) in the polysaccharide derivative was 0.010.
The degree of substitution of the group (A) of the polysaccharide derivative is determined by the Zeisel method [D. G. Anderson, Anal. Chem. , 43, 894 (1971)]. This degree of substitution indicates the average number of substituents per constituent monosaccharide residue.

Examples 1 and 2
Special machine industry, Ajihomo mixer, MODEL F. The hydrophobic compound (a) and the polymer compound (b) were stirred and mixed for 30 minutes under the conditions of a temperature of 40 ° C. and a rotation speed of 100 rpm at a ratio shown in Table 1 using 2/5. Next, while continuing stirring at the same speed, ion-exchanged water was added dropwise under conditions of 10 g / min, and stirred for 30 minutes or more after completion of the addition to obtain an oil-in-water emulsion. To this oil-in-water emulsion, the water-soluble saccharide (c) was added and further stirred at the same speed for 30 minutes or more to obtain an oil-in-water emulsion with reduced viscosity. Various properties of this oil-in-water emulsion were evaluated. The results are shown in Table 1.
Comparative Examples 1 and 2
In Example 1 and 2, the same operation as Example 1 and 2 was performed except not using water-soluble saccharide | sugar (c), and the oil-in-water emulsion was obtained. The results are shown in Table 1.

  From Table 1, it can be seen that the oil-in-water emulsions of Examples 1 and 2 have a markedly lower viscosity than the oil-in-water emulsions of Comparative Examples 1 and 2. Moreover, the oil-in-water emulsions of Examples 1 and 2 were also excellent in emulsion stability.

  The oil-in-water emulsion of the present invention is an oil-in-water emulsion having good emulsion stability and low viscosity. For this reason, it can be used suitably in fields such as cleaning agents, cosmetics, skin care agents, clothing treatment agents, and fragrances.

Claims (7)

An oil-in-water emulsion obtained by emulsifying a hydrophobic compound (a) with a polymer compound (b) having a group represented by the following formula (1) in at least a side chain, wherein a water-soluble saccharide is added to an aqueous phase. An oil-in-water emulsion containing (c) and having a water content of 40 to 90% by mass.
^{_{- (OX) n -E 2 -R}} (1)
(Wherein x is the same or different divalent saturated hydrocarbon group having 1 to 6 carbon atoms, n is a number of 5 to 300, E ² is an ether bond or an oxycarbonyl group, and R is a hydroxyl group. And an optionally substituted alkyl group having 4 to 30 carbon atoms.)   The oil-in-water emulsion of Claim 1 containing 1-50 mass% of hydrophobic compounds (a) and a high molecular compound (b) 0.01-10 mass%.   The oil-in-water emulsion of Claim 1 or 2 containing 8-50 mass% of water-soluble saccharides (c).   The water according to any one of claims 1 to 3, wherein the hydrophobic compound (a) is at least one selected from higher alcohols, sterols, silicones, fluorine-based oils, fragrances and other oil components. Oil-type emulsion.   The polymer compound (b) is a group of the polysaccharide derivative (b-1) having a group represented by the formula (1) and / or the group represented by the formula (1), on average, 0 per main chain constituting monomer unit. The oil-in-water emulsion according to any one of claims 1 to 4, which is a water-soluble synthetic polymer compound (b-2) having a weight average molecular weight of 10,000 to 2,000,000 having 0.0001 to 0.1.   The oil-in-water emulsion according to any one of claims 1 to 5, wherein the water-soluble saccharide (c) is a starch degradation product. An oil-in-water emulsion obtained by emulsifying a hydrophobic compound (a) with a polymer compound (b) having a group represented by the following formula (1) in at least a side chain; a water-soluble saccharide (c); A method for producing an oil-in-water emulsion.
^{_{- (OX) n -E 2 -R}} (1)
(Wherein x is the same or different divalent saturated hydrocarbon group having 1 to 6 carbon atoms, n is a number of 5 to 300, E ² is an ether bond or an oxycarbonyl group, and R is a hydroxyl group. And an optionally substituted alkyl group having 4 to 30 carbon atoms.)