JP2000319118A - Medicine for external use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a medicine for external use excellent in various performances required according to use in conventional medicine for external use. SOLUTION: This medicine for external use includes 30-90 mol.% of an alkoxylate of a higher secondary alcohol (X) expressed by the general formula [R1 and R2 are each an alkyl group and the sum of carbons in R1 and R2 is 7-29 (the numbers of carbons in R1<= that of R2), A is a lower alkylene, n is an average of 1-100. In the proviso that in the case of n>=2 the oxyalkylene groups expressed by AO may be one or two or more kinds and in the case of two or more kind of oxyalkylene groups n means that the compound has average n oxyalkylene groups as a whole] (R1 is methyl) and 70-10 mol.% of an alkoxylate of a higher secondary alcohol (Y) in which R1 is a >=2C alkyl group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an external preparation for skin containing an oil agent comprising an ether compound having a specific structure. More specifically, it relates to a skin external preparation containing a base oil having appropriate viscosity, low irritation and low odor, and a skin external preparation containing a nonionic surfactant excellent in solubilizing ability, emulsifying ability and dispersing ability. It is.

[0002]

2. Description of the Related Art
Various base oils and surfactants are used in skin external preparations. Of these, base oils are selected from various oil agents according to the purpose, based on the spread, oiliness, wettability, ease of washing, solubility of medicinal components, etc. when applied to the skin etc. Used. Surfactants are mainly used for emulsification or solubilization of water or aqueous components and oil components, dispersion of solid components, etc., and are used by selecting from various surfactants according to the purpose. I have. Therefore, a base oil and a surfactant that can be used for a wide range of purposes have been demanded. In addition, base oils and surfactants used in these skin external preparations are required to have low irritation and low odor.

[0003] Therefore, an object of the present invention is to spread, greasy, wettability, ease of washing off, and to dissolve the medicinal components when applied to the skin, etc., and to further reduce hypoallergenicity and odor. A skin external preparation containing a base oil having

Another object of the present invention is to provide a skin containing a surfactant having excellent emulsification or solubility of water or an aqueous component and an oil component, excellent dispersibility of a solid component, and low irritation and low odor. It provides an external preparation.

[0005]

Means for Solving the Problems The present inventors have found that (poly) alkylene glycol monoalkyl ethers having a specific structure are hypoallergenic and odorless, and are incorporated into skin external preparations as base oils or surfactants. Excellent effect (spreading, oiliness, wettability, ease of washing when applied to skin, etc., solubility of medicinal components, emulsification or solubility of water or aqueous and oily components, solid components Of the (poly) alkylene glycol monoalkyl ether of this specific structure and (poly)
The inventors have found that the viscosity and interfacial properties can be freely controlled by changing the kind of alkylene glycol and the number of moles added, so that it can be widely used for external preparations for skin, and have completed the present invention.

That is, an object of the present invention is to provide a compound represented by the general formula (1):

[0007]

Embedded image

[Wherein, R ¹ and R ² are alkyl groups, and the total number of carbon atoms of R ¹ and R ² is 7 to
29, and number of carbon atoms in R ² is greater than the number of carbon atoms of R ¹ (the number of carbon atoms of the carbon atoms ≦ R ² of R ^1), A represents a lower alkylene group, n represents 1 in average 100. However, when n is 2 or more, the kind of oxyalkylene group represented by AO may be one kind or two kinds or more, and when there are two or more kinds of oxyalkylene groups, various oxyalkylene groups are used. Indicates that there are an average of n groups in total. A higher secondary alcohol alkoxylate represented by the formula (I), wherein R ¹ is a methyl group: 30 to 90 mol%
A higher secondary alcohol alkoxylate (Y) in which R ¹ is an alkyl group having 2 or more carbon atoms.
0 mol%, which comprises a higher secondary alcohol alkoxylate comprising:

Another object of the present invention is to provide a long-chain olefin
A higher secondary alcohol alkoxylate obtained by adding a (poly) alkylene glycol to a heavy bond, and / or
Alternatively, it is achieved by a skin external preparation characterized by containing a higher secondary alcohol alkoxylate obtained by further adding an alkylene oxide.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The external preparation for skin according to the present invention has the general formula (1)

[0011]

Embedded image

[Wherein, R ¹ and R ² are alkyl groups, and the total number of carbon atoms of R ¹ and R ² is 7 to
29, and number of carbon atoms in R ² is greater than the number of carbon atoms of R ¹ (the number of carbon atoms of the carbon atoms ≦ R ² of R ^1), A represents a lower alkylene group, n represents 1 in average 100. However, when n is 2 or more, the kind of oxyalkylene group represented by AO may be one kind or two kinds or more, and when there are two or more kinds of oxyalkylene groups, various oxyalkylene groups are used. Indicates that there are an average of n groups in total. A higher secondary alcohol alkoxylate represented by the formula (I), wherein R ¹ is a methyl group: 30 to 90 mol%
A higher secondary alcohol alkoxylate (Y) in which R ¹ is an alkyl group having 2 or more carbon atoms.
0 mol% higher secondary alcohol alkoxylate (hereinafter, also simply referred to as higher secondary alcohol alkoxylate (I)).

In the above formula (1), the lower alkylene group represented by A is an alkylene group having 2 to 8 carbon atoms, preferably 2 to 4 carbon atoms. In the case of an alkylene group having 9 or more carbon atoms, the production cost is high and the hydrophobicity is too strong to be applied to a wide range of skin external preparations, which is not preferable. Therefore, examples of the oxyalkylene group represented by AO include oxyethylene group, oxypropylene group, oxybutylene group, oxypentylene group, oxyhexylene group, oxyheptylene group, oxyoctylene group, and oxyphenylethylene. And preferably an oxyethylene group, an oxypropylene group and an oxybutylene group. In addition, AO in the above general formula (1)
These oxyalkylene groups are, as defined in
It may be composed of only types, or may be composed of two or more types. When the oxyalkylene group is composed of two or more types, the two or more types of oxyalkylene groups may be randomly arranged, or each may be arranged in a block. For example, a configuration may be adopted in which a part of the long chain of the oxyethylene group is an oxypropylene group.

In the above formula (1), the alkyl groups represented by R ¹ and R ² are preferably straight-chain alkyl groups.
The total number of carbon atoms of the carbon atoms and R ² of ^1, 7-2
9, preferably 9 to 19, and the number of carbon atoms of R ² is R
^{It is not} less than ¹ carbon atoms (the number of carbon atoms of R ¹ ≦ the number of carbon atoms of R ² ). When the total number of carbon atoms of R ¹ and R ² is 6 or less, the alkyl group is too short and lacks hydrophobicity, resulting in insufficient performance as a base oil as a surfactant. On the other hand, when the total number of carbon atoms of R ^{1 and} the number of carbon atoms of R ² is 30 or more, the alkyl group is too long and the hydrophobicity is too strong, so that the base oil has the performance as a surfactant. It is not preferable because it is insufficient. That is, by controlling the total of the number of carbon atoms of R ^{1 and} the number of carbon atoms of R ² within the above range, it is possible to express desired properties, and an important requirement for enhancing the usefulness as an external preparation for skin. It can be said that.

In the general formula (1), n is an average of 1 to 1
00, preferably 1 to 70. When n exceeds 100, the performance as a surfactant is insufficient as a base oil, such as an excessive increase in viscosity and a decrease in interfacial properties, which is not preferable. The desired viscosity and interface characteristics can be freely controlled by changing the number of added moles n of the AO. Therefore, the range of n is adjusted so that the optimum viscosity and interface characteristics can be obtained according to the intended use of the external preparation for skin. Is more preferable to be determined. When n is 2 or more, AO
The type of the oxyalkylene group represented by
When the number of the oxyalkylene groups is two or more, the number of the various oxyalkylene groups is n on average.

Further, in the external preparation for skin of the present invention, in the higher secondary alcohol alkoxylate represented by the general formula (1), the higher secondary alcohol alkoxylate (X) 30 wherein R ¹ is a methyl group is used. To 90 mol%, preferably 40 to 80 mol%, and R ¹ has 2 carbon atoms.
The higher secondary alcohol alkoxylate (Y) which is the above alkyl group is 70 to 10 mol%, preferably 60 to
It is a requirement that a composition ratio of 20 mol% is included. This is because when the proportion of the higher secondary alcohol alkoxylate (X) exceeds 90 mol%,
The properties of skin external preparations, including poor spreading and poor usability as a base oil, poor emulsifying, solubilizing, and dispersing properties as surfactants, and lowering the overall properties of higher secondary alcohol alkoxylates It is not preferable because it decreases.
On the other hand, if the proportion of the higher secondary alcohol alkoxylate (X) is less than 30 mol%, undesirable impurities are mixed in the production method, and irritation and odor are generated. In addition to deteriorating the characteristics, the reaction time is long, the productivity is low, and the production cost is high, which is not economically advantageous. Since the higher secondary alcohol alkoxylate (I) of the present invention contains almost no alkyl alcohol to which no alkoxylate is added, the external preparation for skin of the present invention has low odor and low irritation. And has the advantage of

The higher secondary alcohol alkoxylate (I) contained in the external preparation for skin of the present invention can be synthesized, for example, by the following reaction.

That is, it can be produced by reacting a long-chain olefin having 8 to 30 carbon atoms with a (poly) alkylene glycol in the presence of an acid catalyst, and separating the product by distillation, extraction or other methods.

Here, the long-chain olefin used as a raw material for obtaining a higher secondary alcohol alkoxylate has a carbon number of 8 to 3 having an ethylenically unsaturated bond.
It is essential that the hydrocarbon is 0, and it is preferably an acyclic hydrocarbon having 10 to 20 carbon atoms and having an ethylenically unsaturated bond. Specific examples of the long-chain olefin include octene, decene, dodecene, tetradecene, hexadecene, octadecene, eicosene, dococene, tetracocene, hexacocene, octacocene, and triacene, such as 1-decene, 2-decene, 1-dodecene, and 2-decene. Dodecene, 3-dodecene, 4-dodecene, 5-
Dodecene, 1-tetradecene, 2-tetradecene, 1-hexadecene and the like. Of these, decene, dodecene, tetradecene, hexadecene, octadecene and eicosene are preferred from the viewpoint of performance as a base oil and a surfactant. These may be used alone or in the form of a mixture of two or more.

These long-chain olefins may have an unsaturated bond at the α-position, an inner position, or a mixture of the α-position and the inner-position. It can be used without any particular limitation. Of course, two or more of these long-chain olefins having different unsaturated bond positions can be used in combination.

Specific examples of the (poly) alkylene glycol used as a raw material to obtain the higher secondary alcohol alkoxylate (I) include monoethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, monopropylene glycol, Dipropylene glycol, tripropylene glycol, polypropylene glycol, 1,3-propanediol, 1,2-butanediol, 2,3-butanediol, 1,4-butanediol, 1,6-hexanediol, 1,4- Cyclohexanemethanediol and the like. Among them, monoethylene glycol, monopropylene glycol, 1,3-propanediol, from the viewpoint of reactivity, yield, and performance of the obtained higher secondary alcohol alkoxylate as a base oil or a surfactant,
1,2-butanediol, 2,3-butanediol,
It can be said that 1,4-butanediol is preferable. These may be used alone or in the form of a mixture of two or more.

Here, the molar ratio of the (poly) alkylene glycol to the long-chain olefin is not particularly limited, but is preferably 0.05-20, more preferably 0.1-10. If the molar ratio is less than 0.05, the yield of the higher secondary alcohol alkoxylate decreases, while if it exceeds 20, the volume of the reactor becomes large, which is not preferable because it is not economical. . As the reaction conditions for adding the (poly) alkylene glycol to the unsaturated bond of the long-chain olefin, the reaction temperature is usually 50 to 250 ° C, preferably 100 to 200 ° C.
° C, and the reaction pressure may be any of reduced pressure, normal pressure or increased pressure, but is preferably in the range of normal pressure to 20 kg / cm ² . When the reaction temperature is lower than 50 ° C., the reaction rate is too slow. On the other hand, when the reaction temperature is higher than 250 ° C., polymerization of a long-chain olefin, decomposition of (poly) alkylene glycol, polycondensation, etc. occur, resulting in a selectivity. Is unfavorable.

Specific examples of the acid catalyst used in the reaction between the long-chain olefin and the (poly) alkylene glycol include a strongly acidic ion exchange resin, a crystalline aluminosilicate such as BEA type zeolite, and dodecylbenzenesulfonic acid. From the viewpoint of reactivity, crystalline aluminosilicate is preferred, and among them, BEA zeolite is particularly desirable.

The acid catalyst is used in an amount of 1 to 50% by weight, preferably 2 to 30% by weight, based on the long-chain olefin. If the amount of the catalyst is less than 1% by weight, sufficient catalytic activity cannot be obtained and the addition reaction cannot be promoted. On the other hand, 5
If the amount exceeds 0% by weight, it is not preferable because effects equivalent to further addition cannot be obtained and uneconomical.

The higher secondary alcohol alkoxylate contained in the external preparation for skin of the present invention is, as described above, a product obtained by reacting a long-chain olefin having 8 to 30 carbon atoms with a (poly) alkylene glycol. Things (I-
In addition to a), the product (Ia) may be further added with an alkylene oxide such as ethylene oxide, propylene oxide, butylene oxide, or styrene oxide. This product (I-
The higher secondary alcohol alkoxylate (Ib) obtained by adding an alkylene oxide to a) can be obtained, for example, by adding an alkylene oxide to the above product (Ia) in the presence of an alkali catalyst.

The number of moles of the alkylene oxide added to the higher secondary alcohol alkoxylate (Ia) of the above product is not particularly limited, but is preferably 1 to 99, more preferably 1 to 69. . When the number of added moles of the alkylene oxide exceeds 99, the number of added moles n of AO in the above general formula (1) representing the higher secondary alcohol alkoxylate (Ib) is in the range defined above. Therefore, the desired viscosity, low irritation, and low odor cannot be obtained, and when added to cosmetics or parts for non-medical use, the solubilizing ability, emulsifying ability, and dispersing ability become insufficient.

Further, the above product (Ia) is further added with
Reaction conditions for adding the kylene oxide include reaction temperature
The degree is usually 50 to 250 ° C, preferably 100 to 200 ° C.
° C, and the reaction pressure may be normal pressure or pressure.
Iga, normal pressure ~ 20kg / cm ^TwoIs desirable. the above
When the reaction temperature is lower than 50 ° C., the reaction rate is slow.
On the other hand, when the temperature exceeds 250 ° C, decomposition and by-products occur.
It is not preferable, for example, that an increase in the composition occurs.

Examples of the alkali catalyst include hydroxides of elements belonging to alkali metals or alkaline earth metals, for example, sodium hydroxide, potassium hydroxide, lithium hydroxide, magnesium hydroxide, calcium hydroxide,
Barium hydroxide and the like can be mentioned. From the viewpoint of availability and reactivity, preferred are sodium hydroxide and potassium hydroxide. These may be powdered, granular, or added as an aqueous solution to perform dehydration. The amount of the alkali catalyst used is preferably from 0.01 to 2.0% by weight, and more preferably from 0.02 to 0.5% by weight, based on the starting alkoxylate.

As described above, the higher secondary alcohol alkoxylate contained in the external preparation for skin of the present invention can be obtained from the higher secondary alcohol alkoxylate (Ia) and / or (Ib) obtained by the above-mentioned production method. You can also catch it. Therefore, the skin external preparation of the present invention also comprises
Higher secondary alcohol alkoxylate (Ia) obtained by adding (poly) alkylene glycol to the double bond of long chain olefin and / or higher secondary alcohol obtained by further adding alkylene oxide It may be characterized by containing an alcohol alkoxylate (Ib). That is, the higher secondary alcohol alkoxylate obtained through such a production process is represented by the above general formula (1), wherein R ^{1 in the} formula is a methyl group, and a higher secondary alcohol alkoxylate (X). Since the constituent ratio with the higher secondary alcohol alkoxylate (Y) in which R ¹ is an alkyl group of 2 or more is the ratio specified above, the constituent ratio is adjusted after production. It is not necessary to perform the troublesome operation of. However, in the skin external preparation of the present invention defined by the above-mentioned method description, it is not always necessary to have the composition ratio as defined above. If they are satisfied, they are included in the technical scope of the present invention.

When the higher secondary alcohol alkoxylate contained in the external preparation for skin of the present invention is used as a water-insoluble base oil, the oxyalkylene group of the higher secondary alcohol alkoxylate (general formula ( A in 1)
O) The content of the oxyethylene group (EO) in the whole is 50% or less, preferably 30% or less, and the number of moles of the EO added is 10 mol or less, preferably 5 mol or less. By setting the content of EO or the number of moles of EO in the entire AO within the above range, the skin external preparation containing such a water-insoluble base oil has low irritation, low odor, moderate viscosity, and other properties. If the compatibility with the oil-soluble component is excellent and the solubility is within the above preferred range, the properties of the skin external preparation containing the water-insoluble base oil can be more remarkably obtained.

On the other hand, when the higher secondary alcohol alkoxylate contained in the external preparation for skin of the present invention is used as a surfactant, for example, when an oily component such as a cream or an emulsion is emulsified in water (in water) Oil type (O / W type)
Emulsion), when water is emulsified in an oily component (water-in-oil (W / O type) emulsion), for example, when a fragrance or an oily component is solubilized in water like a lotion,
For example, when a pigment is dispersed in water or an oil component as in a foundation, the HLB (hydrophilic-lipophilic ratio) may be controlled and used according to the purpose (for example, the surfactant having an HLB of about 8 to 18). O /
A W / E emulsion is easily formed, and a W / O emulsion is easily formed when a surfactant having an HLB of about 3 to 6 is used. Here, in order to increase the HLB (increase the hydrophilicity ratio), the oxyethylene group (EO) occupying the entire oxyalkylene group (AO in the general formula (1)) of the higher secondary alcohol alkoxylate is required. What is necessary is just to make it a high addition mole. On the other hand, to reduce the HLB (reduce the proportion of hydrophilicity), it is necessary to add an oxyethylene group (EO) to the entire oxyalkylene group (AO in the general formula (1)) of the higher secondary alcohol alkoxylate. The number of moles may be reduced, and alkylene such as oxypropylene group (PO) or oxybutylene group (BO) occupies the entire oxyalkylene group (AO in general formula (1)) of the higher secondary alcohol alkoxylate. The oxide content may be increased. By using the higher secondary alcohol alkoxylate with its HLB (hydrophilic-lipophilicity ratio) controlled in this way, it is excellent for low external odor, low odor, emulsifying ability, dispersing ability and solubilizing ability for external use on skin. Agent can be obtained.

Examples of the skin external preparation of the present invention include cosmetic soap, cleansing cream, face wash, rinse, skin cream, skin milk, emollient cream, lotion, perfume, cologne, cosmetic oil, cosmetics for hair, pomade, Tic, hair cream, hair dye, condensate, powder, pack, shaving cream, shaving lotion, tanning oil, sunscreen oil, tanning lotion, sunscreen lotion, tanning cream, sunscreen cream, foundation, massage cream, lipstick Lip balm, blusher, eye makeup, mascara, eyebrow ink, beauty nail enamel, beauty nail enamel remover, hair dye, bath cosmetics, toothpaste, deodorant, hair restorer and hair restorer, cartilage, compress and medicated lip balm .

In addition to the above-mentioned higher secondary alcohol alkoxylate, if necessary, for example, an oil component other than the above-mentioned higher secondary alcohol alkoxylate, phospholipid, etc. , Alcohols, water-soluble polymers, humectants, thickeners, gelling agents, sugars,
Surfactants, emulsifiers, solubilizers / dispersants other than the above-mentioned higher secondary alcohol alkoxylates, ultraviolet absorbers, preservatives, antiscenting agents, antioxidants, whitening agents, fluorescent materials,
Organic pigments, inorganic pigments, organic powders, inorganic powders, pigments, fragrances, sequestering agents, pH regulators, binders, extenders, vitamins, amino acids, hormones, peptides, bioactive plant extracts, nutrients, fungicides, Keratin improvers, keratolytics, antibiotics, skin permeation enhancers, blood circulation enhancers, anti-inflammatory agents, cell activators, anti-inflammatory agents, analgesics, emollients, emollients, wound healing agents, metabolic accelerators, etc. Can be blended in appropriate amounts. These additives may be used alone or in combination of two or more.

If necessary, the external preparation for skin of the present invention may be used in combination with a conventionally known base oil in addition to the above-mentioned higher secondary alcohol alkoxylate. As such conventionally known base oils, various vegetable oils, animal oils, mineral oils and synthetic oils can be used. For example, oils and fats such as olive oil, jojoba oil, mink oil, and mocro oil; beeswax,
Waxes such as candelilla wax; mineral oils such as liquid paraffin, microcrystalline wax and petrolatum; fatty acids such as stearic acid and oleic acid; higher alcohols such as cetyl alcohol, 2-octyldodecanol and isostearyl alcohol; Esters such as isopropyl acid; isopropyl lanolin fatty acid;
Lanolin derivatives such as lanolin alcohol; starch fatty acid esters; silicone compounds such as methylphenylpolysiloxane and dimethylpolysiloxane; and fluorine-based oils such as perfluoropolyether. These base oils may be used alone or in a combination of two or more.

The external preparation for skin of the present invention may be used, if necessary, in combination with a conventionally known surfactant in addition to the above-mentioned higher secondary alcohol alkoxylate. Examples of these conventionally known surfactants include, for example, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyglycerin fatty acid ester, glycerin fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alkyl ether other than the present invention, polyoxyethylene Nonionic surfactants such as ethylene alkyl aryl ethers; Anionic surfactants such as higher fatty acid salts, ether carboxylates and higher alkyl sulfonates; Cationic interfaces such as alkyl quaternary ammonium salts, polyamines and alkylamine salts Activators and the like. One of these surfactants may be used alone, or two or more thereof may be used in combination.

[0036]

EXAMPLES Hereinafter, the skin external preparation of the present invention will be specifically described with reference to examples.

Synthesis Example 1 1680 g of 1-dodecene, monoethylene glycol 18
60 g and PQ BEA type zeolite (trade name CP
811E-22) (206 g) was charged into a 5000 ml glass reactor equipped with a stirrer and a reflux condenser, and reacted at 150 ° C. for 10 hours under a nitrogen atmosphere. After the reaction,
The reaction solution was cooled to room temperature, the upper layer of the dodecene layer separated from the phase was separated, and batch distillation was performed. After distilling off unreacted isomerized dodecene (1-dodecene in dodecene was 7 mol% as a result of NMR analysis), the degree of vacuum was 3 mm.
276 g of a fraction at 135 to 137 ° C. in Hg was recovered. This fraction was secondary dodecanol monoethoxylate, and according to NMR analysis, the proportion of ethoxylate in which R ¹ was a methyl group was 70 mol%. The secondary dodecanol monoethoxylate obtained in Synthesis Example 1 was almost odorless.

Synthesis Example 2 A reaction was carried out in the same manner as in Synthesis Example 1 except that 2240 g of 1-hexadecene was used instead of 1-dodecene. After completion of the reaction, the reaction solution was cooled to room temperature, the upper hexadecene layer separated from the phase was separated, and batch distillation was performed. Unreacted isomerized hexadecene (NM
R was analyzed, the 1-hexadecene in hexadecene was 6 mol%), and the degree of pressure reduction was 2 mmHg.
314 g of a fraction at 170 to 172 ° C. was recovered. This fraction was secondary hexadecanol monoethoxylate, and NMR analysis revealed that the proportion of ethoxylate in which R ¹ was a methyl group was 68 mol%. The secondary dodecanol monoethoxylate obtained in Synthesis Example 2 was almost odorless.

Synthesis Example 3 Secondary dodecanol monoethoxylate 5 of Synthesis Example 1
0.0 g and 0.10 g of potassium hydroxide were charged into a 500 ml stirred autoclave made of stainless steel, purged with nitrogen, heated to 110 ° C., and dehydrated at 50 mmHg for 1 hour. Then, the temperature was raised to 150 ° C.
1.7 g were introduced in 3 hours, and then 150 h for another hour.
It was kept at ° C. After the completion of the reaction, the system was cooled and the internal gas was purged to obtain secondary dodecanol polyethoxylate. The number of moles of ethylene oxide added to this polyethoxylate is 20 moles on average (the ethylene glycol added in Synthesis Example 1 is also included as an added mole of ethylene oxide). The secondary dodecanol polyethoxylate obtained in Synthesis Example 3 was almost odorless.

Synthesis Example 4 50.0 g of the secondary hexadecanol monoethoxylate of Synthesis Example 2 and 0.10 g of potassium hydroxide were charged into a 500 ml stirred autoclave made of stainless steel, purged with nitrogen, and then heated to 110 ° C. Then, it was dehydrated at 50 mmHg for 1 hour. Then, the temperature was raised to 150 ° C.
4.5 g are introduced in 3 hours, and then 150 h for another hour.
It was kept at ° C. After the completion of the reaction, the system was cooled and the internal gas was purged to obtain secondary hexadecanol polyethoxylate. The number of moles of ethylene oxide added to this polyethoxylate is 25 moles on average (the ethylene glycol added in Synthesis Example 2 is also included as an added mole of ethylene oxide). The secondary hexadecanol polyethoxylate obtained in Synthesis Example 4 was almost odorless.

Example 1 (Production of emollient cream) An emollient cream having the composition shown in Table 1 below was produced. After heating a mixture of purified water and propylene glycol and the remaining mixture of the components shown in Table 1 below to 70 ° C., they were mixed and uniformly emulsified by a homomixer. The emulsion was cooled to obtain an emollient cream. The feeling of use as an emollient cream was good.

[0042]

[Table 1]

In order to examine the irritancy of the emollient cream of this example, a patch test (according to the Schwarzpek method) was carried out for five panelists. There were no positives after 48 hours.

Example 2 (Production of W / O Massage Cream) A massage cream having the composition shown in Table 2 below was produced. The mixture of purified water and soap powder and the remaining mixture of the components shown in Table 2 below were each heated and dissolved at 70 ° C., and then both were mixed and uniformly emulsified by a homomixer. The emulsion was cooled to obtain a massage cream. The feeling of use as a massage cream was good.

[0045]

[Table 2]

Example 3 (Production of Soft Lotion) A soft lotion having the composition shown in Table 3 below was prepared. The components shown in Table 3 below were sufficiently mixed at room temperature to obtain a softening lotion. The feeling of use as a softening lotion was good.

[0047]

[Table 3]

Example 4 (Production of foundation cream) A foundation cream having the composition shown in Table 4 below was produced. The powdered pigment was sufficiently dispersed in purified water, and the mixture of the remaining components shown in Table 4 below was heated and dissolved at 70 ° C., and then both were uniformly emulsified and dispersed by a homomixer. The emulsion was cooled to obtain a foundation cream. The feeling of use as a foundation cream was good.

[0049]

[Table 4]

Example 5 (Manufacture of lipstick) A lipstick having the composition shown in Table 5 below was manufactured. The components shown in Table 5 below were sufficiently mixed by heating at 70 ° C., put into a mold, and rapidly cooled to obtain a lipstick. The feeling of use as a lipstick was good.

[0051]

[Table 5]

[0052]

The external preparation for skin according to the present invention has excellent solubilizing ability, emulsifying ability, and dispersing ability as a base oil and a surfactant component. Wettability,
It is easy to wash off, has excellent solubility of medicinal components, and contains a high-grade secondary alcohol alkoxylate with a specific structure that has appropriate viscosity, low irritation and low odor. Available to

 ──────────────────────────────────────────────────の Continuing from the front page (72) Hideaki Tsuneki, Inventor 5-8 Nishiburi-cho, Suita-shi, Osaka Nippon Shokubai Co., Ltd. F-term (reference) 4C083 AA082 AA122 AB242 AC012 AC022 AC072 AC102 AC122 AC171 AC172 AC242 AC352 AC442 AD041 AD042 AD512 CC04 CC05 CC12 CC13 DD32 EE06 EE07 4J002 CH02W CH02X FD310 GB00

Claims (2)

[Claims] 1. A compound of the general formula (1) [Wherein, R ¹ and R ² are alkyl groups, the total number of carbon atoms of R ¹ and R ² is 7 to 29, and R 1
² carbon atoms is greater than the number of carbon atoms of R ¹ (the number of carbon atoms of the carbon atoms ≦ R ² R ^1), A represents a lower alkylene group, n represents 1 to 100 on average. However, when n is 2 or more, the kind of oxyalkylene group represented by AO may be one kind or two kinds or more, and when there are two or more kinds of oxyalkylene groups, various oxyalkylene groups are used. Indicates that there are an average of n groups in total. A higher secondary alcohol alkoxylate represented by the formula: wherein R ¹ is a methyl group, 30 to 90 mol% of a higher secondary alcohol alkoxylate (X), and R ¹ is an alkyl having 2 or more carbon atoms. High-quality second base
Grade alcohol alkoxylate (Y) 70 to 10 mol
% Of a higher secondary alcohol alkoxylate. 2. The method according to claim 1, wherein the double bond of the long-chain olefin is (poly)
An external skin preparation comprising a higher secondary alcohol alkoxylate obtained by adding an alkylene glycol and / or a higher secondary alcohol alkoxylate obtained by further adding an alkylene oxide.