JP5954935B2 - Moisturizer and external preparation for skin - Google Patents

Description

  The present invention relates to a moisturizer and an external preparation for skin containing a novel ester oil as an active ingredient. More specifically, a moisturizing agent containing as an active ingredient one or more ester oils selected from neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate, and It relates to an external preparation for skin.

  So far, in order to provide a moisturizing ingredient that prevents the skin from drying and moisturizes the skin, various active ingredients have been studied. For example, as a moisturizing agent excellent in moisturizing effect and safety, an extract of Julianidaceae plant (see Patent Document 1), an extract of Brassicaceae Pydium genus plant (see Patent Document 2), an extract of an Asteraceae genus Camelidae Patent Document 3), Maple plant extract (see Patent Document 4), Hyssop plant extract (see Patent Document 5), Novanoceae plant extract (see Patent Document 6), Amber plant extract (See Patent Document 7) and the like.

  Further, when the moisture content of the skin decreases, phenomena such as rusting and cracking occur. Therefore, it is important as a moisturizing agent to suppress moisture that evaporates from the inside of the skin. As a mechanism for suppressing skin moisture transpiration, a mechanism is disclosed in which an oil agent covers the skin from above (see Non-Patent Document 1). It has been reported that this effect is generally higher for non-polar oils and lower for higher polarities (see Non-Patent Document 2).

JP-A-11-209223 JP 2001-39854 A JP 2002-20262 A JP 2003-1113068 A JP 2004-262862 A JP 2006-69939 A JP 2007-77072 A Seiji Nishiyama et al., Journal of Japan Cosmetics Engineers, 16, 136 (1983) Hiroyuki Shikagi, Fragrance Journal Special Issue, No. 20 (2007)

Nonpolar oils such as liquid paraffin and petrolatum are considered to have an effect of suppressing moisture transpiration of the skin and moisturizing, and have been widely used as a central component of an ointment base material. However, these are in a state in which a non-polar foreign substance is applied on the skin, so that they are uncomfortable and uncomfortable.

On the other hand, polar oils that penetrate into the skin after application have little stickiness and good usability, but the effect of capping on the skin is low, and it is difficult to obtain a moisture transpiration control effect. Therefore, the development of a moisturizing agent having both excellent moisture transpiration control effect and good usability was expected.

  As a result of examining various components, the present inventors have found that moisturizing effect and stickiness are excellent in neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate. A new usability was found and further studies were made to complete the present invention.

  That is, the present invention is a moisturizing agent comprising as an active ingredient one or more ester oils selected from neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate. It relates to the agent.

  Another invention is characterized in that it contains one or more ester oils selected from neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate. The present invention relates to an external preparation for skin.

  According to the present invention, the active ingredient is one or more ester oils selected from neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate. Thus, it is possible to provide a humectant having an excellent effect.

  By blending these moisturizing agents into the external preparation for skin, various compositions that prevent the skin from drying and moisturize the skin can be provided.

  The neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate of the present invention can be used alone or in combination of two or more.

  The production method of neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate, which are ester oils of the present invention, is a conventionally known method for producing ester oils. It is equivalent. For example, it can be obtained by an esterification reaction of a higher fatty acid and a higher alcohol in the presence of a suitable catalyst such as an alkali catalyst.

The ester oil of the present invention has an excellent moisturizing effect and can be used as a moisturizing agent.
The moisturizing agent containing the ester oil of the present invention as an active ingredient can give an excellent moisturizing effect to the skin and hair.

  As long as the moisturizing agent of the present invention contains neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate as active ingredients, the form and the presence or absence of other ingredients, etc. There are no restrictions on the above. As for the form, any form such as liquid, paste, gel, solid, powder, etc. can be selected according to its use and the like, vehicle (excipient), solvent, Other general additives (antioxidants, colorants, dispersants, etc.) can optionally be included.

  Neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate have an excellent moisturizing effect and prevent skin dryness by blending it. It is possible to provide an external preparation for skin that provides moisture.

  Here, the external preparation for skin means all external compositions for external use on the skin or hair, such as cosmetics, quasi-drugs, and external medicines.

  The dosage form of the external preparation for skin is arbitrary, and can be provided, for example, as a solubilizing system such as lotion, a dispersion system such as calamine lotion, or an emulsifying system such as cream or emulsion. Further, it can be provided in various dosage forms such as an aerosol form, an ointment, and a poultice filled with a propellant.

  Specifically, various cosmetics such as milky lotion, cream, lotion, lotion, pack, beauty essence, cleaning agent, makeup cosmetics, quasi-drugs and topical medicines can be exemplified.

  By blending neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate into skin external preparations such as cosmetics, external medicines and quasi drugs, An external preparation for skin that prevents drying and provides moisture to the skin can be provided. Therefore, for example, it can be preferably used as a skin external preparation for moisturizing.

  In addition to the ester oil of the present invention, the external preparation for skin optionally contains any component that is usually blended in pharmaceuticals, quasi-drugs, skin cosmetics, hair cosmetics, and cleansing agents as required. , For example, water, oily ingredients, powders, pigments, emulsifiers, solubilizers, gelling agents, detergents, UV absorbers, anti-inflammatory agents, thickeners, pH adjusters, chelating agents, drugs (medicinal ingredients), A fragrance | flavor, resin, antibacterial and antifungal agent, antioxidant, alcohol, etc. can be mix | blended suitably.

  The amount of neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate can be adjusted depending on the type, purpose, etc. From the viewpoint of feeling of use, the content is preferably 0.01 to 90.0% by mass, more preferably 0.1 to 50% by mass, and still more preferably 1 to 15% by mass with respect to the total amount.

  The following are examples of production of neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate, test methods for evaluating the moisturizing effect, and formulation examples as external preparations for skin Although described in more detail, the technical scope of the present invention is not limited thereby.

[Production example of neopentyl linoleate]
Water produced by charging 480.5 g (1.5 mol) of linoleic acid and 132.2 g (1.5 mol) of 2,2-dimethyl-1-propanol into a reactor and heating to 210 to 220 ° C. in a nitrogen stream. The esterification reaction was carried out for 10 hours while distilling off to obtain 625 g of the desired ester compound. The obtained ester compound had an acid value of 2.3, a saponification value of 130, an iodine value of 123, a hydroxyl value of 0.5, and a hue (APHA) of 60.

[Production example of isobutyl isostearate]
426.7 g (1.5 mol) of isostearic acid and 111.2 g (1.5 mol) of 2-methyl-1-propanol were charged into a reactor, heated to 210 to 220 ° C. in a nitrogen stream, and the generated water was distilled. The esterification reaction was performed for 10 hours while leaving to obtain 525 g of the target ester compound. The obtained ester compound had an acid value of 0.1, a saponification value of 165, an iodine value of 0.7, a hydroxyl value of 0.3, and a hue (APHA) of 40.

[Production example of isobutyl hydroxystearate]
Water produced by charging 450.7 g (1.5 mol) of hydroxystearic acid and 132.2 g (1.5 mol) of 2-dimethyl-1-propanol into a reactor and heating to 210 to 220 ° C. in a nitrogen stream. The esterification reaction was carried out for 10 hours while distilling off to obtain 570 g of the desired ester compound. The obtained ester compound had an acid value of 0.3, a saponification value of 161, an iodine value of 1.1, a hydroxyl value of 86.1, and a hue (AHPA) of 80.

[Production example of neopentyl isostearate]
426.7 g (1.5 mol) of isostearic acid and 132.2 g (1.5 mol) of 2,2-dimethyl-1-propanol are charged into a reactor and heated to 210-220 ° C. in a nitrogen stream to produce. An esterification reaction was carried out for 10 hours while distilling off water to obtain 545 g of the desired ester compound. The obtained ester compound had an acid value of 0.06, a saponification value of 157, an iodine value of 0.8, a hydroxyl value of 0.1, and a hue (AHPA) of 20.

[Production example of neopentyl hydroxystearate]
Hydroxystearic acid 450.7 g (1.5 mol) and 2,2-dimethyl-1-propanol 132.2 g (1.5 mol) were charged into a reactor and heated to 210-220 ° C. in a nitrogen stream. The esterification reaction was carried out for 10 hours while distilling off the water to obtain 572 g of the desired ester compound. The obtained ester compound had an acid value of 0.6, a saponification value of 155, an iodine value of 2.3, a hydroxyl value of 81.8, and a huener (Gardner) of 5.

[Production example of isostearyl isobutanoate]
A reactor was charged with 132 g (1.5 mol) of isobutanoic acid and 405.7 g (1.5 mol) of isostearyl alcohol, heated to 210-220 ° C. in a nitrogen stream, and distilled for 10 hours while distilling off the generated water. An esterification reaction was performed to obtain 524 g of the target ester compound. The obtained ester compound had an acid value of 0.06, a saponification value of 165, an iodine value of 1.1, a hydroxyl value of 0.1, and a hue (AHPA) of 10.

  The ester oil was used to evaluate the moisturizing effect and stickiness.

<Evaluation of moisturizing effect (moisture transpiration suppression effect) and stickiness of ester oil>
The test was performed in a room adjusted at a temperature of 20 ° C. to 22 ° C. and a humidity of 40 to 60%. A TEWA meter TM210 (manufactured by C & K) was used for the TEWL (transepidermal moisture transpiration) measurement test after the oil agent was applied.

Moisturizing effect (water loss suppressing effect) is washed human forearm in general detergent, trimmed initial conditions by 15 minutes standing, with respect to the forearm 3 × 3 cm ^2, a liquid oil uniformly 18μl It was evaluated by measuring the amount of water transpiration before coating, 30 minutes after coating, 60 minutes after coating, and 120 minutes after coating. The measurement result is an average value of moisture transpiration of the four panelists, and is a relative value when the pre-application is 1, relative values “◯: 0.76-0.8” “Δ: 0 after 120 minutes of application. .81 to 0.86 ”and“ x: 0.87 to 0.99 ”.

The sticky feeling was evaluated by three professional evaluation panels that applied liquid oil evenly to the forearm, with three choices: “No stickiness: 3 points”, “Slightly sticky: 2 points”, and “Stickiness: 1 point”. The measurement results were expressed as average points “◯: 2.6 to 3 points”, “Δ: 1.6 to 2.5 points”, and “x: 1 to 1.5 points”.

  Table 1 shows the evaluation results of the moisturizing effect (moisture transpiration suppression effect) and stickiness of each oil.

As is apparent from the results in Table 1, it was found that Examples 1 to 6, which are products of the present invention, are excellent ester oils that have a high moisture transpiration suppressing effect and also have a non-sticky feeling.

  On the other hand, the conventional ester oils of Comparative Examples 1 to 7 did not feel sticky but had a low moisture transpiration suppressing effect. Moreover, although Comparative Examples 8-10 which are nonpolar oils have the moisture transpiration suppression effect, they were sticky feeling.

That is, it was confirmed that the ester oil of the present invention is a satisfactory humectant having both a moisturizing effect (moisture transpiration suppressing effect) and a non-sticky feeling of use.

  Then, the formulation example of the skin external preparation which mix | blended the ester oil obtained by said each manufacturing method is shown.

[Example 7] Emulsion (1) Squalane 10.0 (mass%)
(2) Neopentyl linoleate 4.0
(3) Hydrogenated palm kernel oil 0.5
(4) Hydrogenated soybean phospholipid 0.1
(5) Polyoxyethylene monostearate
Sorbitan (20E.O.) 1.3
(6) Sorbitan monostearate 1.0
(7) 1,3-butylene glycol 4.0
(8) Methyl paraoxybenzoate 0.1
(9) Carboxyvinyl polymer 0.15
(10) Purified water 100 (11) Arginine (1% by weight aqueous solution) 20.0
Production method: The oil phase components (1) to (6) are heated and dissolved at 80 ° C. On the other hand, the aqueous phase components (7) to (10) are dissolved by heating at 80 ° C. The oil phase component is added to this while stirring and uniformly emulsified with a homogenizer. After the emulsification, cooling is started, (11) is added at 50 ° C., and the mixture is uniformly mixed to 35 ° C.

[Example 8] Cream (1) Squalane 10.0 (mass%)
(2) Stearic acid 2.0
(3) Isobutyl isostearate 10.0
(4) Hydrogenated soybean phospholipid 0.1
(5) Cetanol 3.6
(6) Lipophilic glyceryl monostearate 2.0
(7) 1,3-butylene glycol 5.0
(8) Methyl paraoxybenzoate 0.1
(9) Arginine (20 mass% aqueous solution) 15.0
(10) Remainder 100 (11) Carboxyvinyl polymer (1% by weight aqueous solution) 15.0
Production method: The oil phase components (1) to (6) are heated and dissolved at 80 ° C. On the other hand, the aqueous phase components (7) to (10) are dissolved by heating at 80 ° C. The oil phase component is added to this while stirring and uniformly emulsified with a homogenizer. After the emulsification is completed, (11) is added, cooling is started, and the mixture is uniformly mixed up to 35 ° C.

[Example 9] Cosmetic liquid (1) The balance (mass%) of purified water 100
(2) Glycerin 10.0
(3) Sucrose fatty acid ester 1.3
(4) Carboxyvinyl polymer (1% by weight aqueous solution) 17.5
(5) Sodium alginate (1% by weight aqueous solution) 15.0
(6) Polyglyceryl monolaurate 1.0
(7) Macadamia nut oil fatty acid phytosteryl 3.0
(8) N-lauroyl-L-glutamic acid di (phytosteryl-2-octyldodecyl) 2.0
(9) Isobutyl hydroxystearate 5.0
(10) Squalane (derived from olive) 1.0
(11) Behenyl alcohol 0.75
(12) Beeswax 1.0
(13) Jojoba oil 1.0
(14) 1,3-butylene glycol 10.0
(15) L-arginine (10% by mass aqueous solution) 2.0
Production method: The aqueous phase components (1) to (6) are mixed and dissolved by heating at 75 ° C. On the other hand, the oil phase components (7) to (14) are mixed and dissolved by heating at 75 ° C. Next, the oil phase component is added to the aqueous phase component and preliminary emulsification is performed, followed by uniform emulsification with a homomixer. Cooling is started after the emulsification is completed, (15) is added at 50 ° C, and the mixture is cooled to 35 ° C and mixed uniformly.

[Example 10] Make-up base cream (1) Squalane 10.2 (mass%)
(2) Cetanol 2.0
(3) Neopentyl isostearate 2.5
(4) Lipophilic glyceryl monostearate 1.0
(5) Propylene glycol 11.0
(6) Sucrose fatty acid ester 1.3
(7) The balance (100) of purified water 100 (titanium oxide) 1.0
(9) Bengala 0.1
(10) Yellow iron oxide 0.4
(11) Fragrance 0.1
Production method: The oil phase components (1) to (4) are mixed and dissolved by heating at 75 ° C. On the other hand, the aqueous phase components (5) to (7) are mixed and dissolved by heating at 75 ° C., and the pigments (8) to (10) are added thereto and dispersed uniformly with a homomixer. The oil phase component is added to the water phase component and emulsified with a homomixer. Cooling is started after completion of emulsification, and the component (11) is added at 40 ° C. and mixed uniformly.

[Example 11] Emulsion foundation (1) Neopentyl hydroxystearate 8.0 (mass%)
(2) Neopentyl linoleate 7.0
(3) Squalane 5.0
(4) Octyldodecyl myristate 5.0
(5) Cetanol 1.0
(6) Polyoxyethylene (20E.O.)
Sorbitan monostearate 1.3
(7) Sorbitan monostearate 0.7
(8) 1,3-butylene glycol 8.0
(9) Xanthan gum 0.1
(10) Methyl paraoxybenzoate 0.1
(11) Remaining water 100 (12) Titanium oxide 9.0
(13) Talc 7.4
(14) Bengala 0.5
(15) Yellow iron oxide 1.1
(16) Black iron oxide 0.1
(17) Fragrance 0.1
Production method: The oil phase components (1) to (7) are mixed and dissolved by heating at 75 ° C. On the other hand, the water phase components (8) to (11) are mixed and dissolved by heating at 75 ° C., and the pigments (12) to (16) are added thereto and uniformly dispersed with a homomixer. Add oil phase ingredients and emulsify. Cooling is started after the emulsification is completed, and the component (17) is sequentially added at 40 ° C. and mixed uniformly.

[Example 12] Water-in-oil emollient cream (1) Liquid paraffin 34.0 (mass%)
(2) Microcrystalline wax 2.0
(3) Isostearyl isobutanoate 5.0
(4) Neopentyl isostearate 2.5
(5) Diglycerin oleate 5.0
(6) Sodium chloride 1.3
(7) Potassium chloride 0.1
(8) Propylene glycol 3.0
(9) 1,3-butylene glycol 5.0
(10) Methyl paraoxybenzoate 0.1
(11) The balance of 100 purified water (12) Fragrance 0.1
Production method: The oil phase components (1) to (5) are mixed and dissolved by heating at 70 ° C. On the other hand, (6) and (7) are dissolved in a part of (11) to 50 ° C., and (8) to (11) are added to the aqueous phase component dissolved by heating at 70 ° C. The oil phase component is added to the aqueous phase component with stirring and emulsified with a homomixer. Cooling is started after completion of emulsification, and (12) is added at 40 ° C. and mixed uniformly.

  Examples 7 to 12 were excellent skin external preparations having a moisturizing effect (moisture transpiration suppression effect) and a non-sticky feeling.

Claims (2)

A humectant comprising one or more ester oils selected from neopentyl linoleate, isobutyl isostearate, isobutyl hydroxystearate, neopentyl isostearate, neopentyl hydroxystearate and isostearyl isobutanoate as an active ingredient. Linoleic acid neopentyl Le, hydroxystearic acid isobutyl, neopentyl isostearic acid, one or more ester oils skin external agent characterized in that it contains selected from neopentyl-hydroxystearic acid and isobutane isostearyl