JP2001011068A - Humectant composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a moisturizing agent composition compatible with the skin, good in sense of use, having high moisture-keeping properties and useful for a cosmetic, a medicine for external use or the like by including a specific 1,3- dioxolan-2-one derivative. SOLUTION: This moisturizing agent composition contains a 1,3-dioxolan-2-one derivative of formula I [R1 is H, a 1-22C (un)saturated linear, branched or cyclic hydrocarbon or the like; R2 to R6 are each H or a 1-22C hydrocarbon], (e.g. 4-hydroxymethyl-1,3-dioxolan-2-one). Preferably, the amount of the formulated compound of formula I is generally 1-60 wt.%, especially 1-40 wt.%. The compound of formula I is obtained by alkylating a corresponding 4- hydroxymethyl-1,3-dioxolan-2-one. The compound of formula I wherein all of R2 to R6 are H is obtained by reacting a compound of formula II with dimethyl carbonate or diethyl carbonate in the presence of a basic catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a humectant composition which has good familiarity with the skin, has a good feeling in use, and has a high moisturizing property.

[0002]

2. Description of the Related Art NMF (natural mois
turizing factor) is secreted,
Although the skin is prevented from drying out, an external preparation containing a moisturizing component is used to supplement the function of NMF. Conventionally used moisturizing components are roughly classified into oily substances and water-soluble substances. Among them, the oily moisturizing component is intended to prevent the evaporation of water by coating the surface of the skin with an oil film. For example, petroleum jelly, lanolin, paraffin, isopropyl palmitate, silicone oil, squalene and the like are used. The water-soluble moisturizing component has a hygroscopic property and absorbs water from the outside until the equilibrium is reached, so as to keep it moist. For example, propylene glycol, 1,3-butylene glycol, glycerin, polyethylene glycol, pyrrolidone carboxylate, Sodium lactate is used.

[0003]

Among the moisturizing ingredients conventionally used, oily moisturizing ingredients are excellent in moisturizing effect, but they are poorly adapted to the skin and have a sense of incongruity. Appeared and there was a problem with the sensory aspect. Water-soluble moisturizing components have an appropriate moisturizing effect, but have a problem that when they absorb moisture, they become more sticky and give the skin a sticky feeling, and their elongation during application is poor. The present invention has been made in order to solve the above-mentioned problems, and an object of the present invention is to provide a moisturizing composition which has good moisturizing properties, has good sticky and moist feeling, and has high moisturizing properties. Is to provide.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, when a certain 1,3-dioxolan-2-one derivative is applied to the skin, skin irritation occurs. The present invention has been found to provide a good feeling of use with less stickiness, good skin familiarity, and being sticky and moist, and has high moisturizing properties. Accordingly, the present invention provides a humectant composition containing a 1,3-dioxolan-2-one derivative represented by the following formula (1).

[0005]

Embedded image

Where R₁Is hydrogen; C₁~ C_{twenty two}Within
Saturated or unsaturated, straight, branched or cyclic hydrocarbon
An aromatic group, a heterocyclic ring or a substitution thereof in the hydrocarbon group
A group attached to the body; or a formula -R_a− (OR_a)_n-OR_bMa
Or the formula-(R_aO)_n-COR _b At R_aIs C_Two~ C
_FourAlkylene groups of the same or different
K, R_bIs C₁~ C_{twenty two}Within the range of saturated or unsaturated
A chain, branched chain, or cyclic hydrocarbon group, or the aforementioned hydrocarbon
A group in which an aromatic group, a heterocyclic ring or a substituent thereof is bonded to a
And n is any one of groups having an integer of 0 to 30,
R_Two~ R₆Are each independently hydrogen; or C₁~ C_{twenty two}of
Saturated or unsaturated linear, branched, or cyclic within range
Is a hydrocarbon group.

[0007]

Embodiments of the present invention will be described below in detail. The humectant composition of the present invention contains a 1,3-dioxolan-2-one derivative represented by the above formula (1) (hereinafter, referred to as “the present derivative”). In this derivative, R ₁ is hydrogen; a saturated or unsaturated linear, branched or cyclic hydrocarbon group in the range of C _{1 to} C ₂₂ ; A group to which a heterocycle or a substituent thereof is bonded; or a compound represented by the formula -R _a- (O
R _a ) _n —OR _b or a formula — (R _a O) _n —COR _b, wherein R _a is a C _{2 to} C ₄ alkylene group which may be the same or different, and R _b is C _{1 to} C ₂₂ Is a saturated or unsaturated straight-chain, branched-chain, or cyclic hydrocarbon group, or a group in which an aromatic, heterocyclic, or a substituted product thereof is bonded to the hydrocarbon group, wherein n is an integer of 0 to 30 Or any of the groups.

Examples of R ₁ in the present derivative include:
For example, hydrogen, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, myristyl, pentadecyl, palmityl , Stearyl group, behenyl group, isobutyl group,
t-butyl group, 1-methylheptyl group, 2-ethylhexyl group, hexenyl group, heptenyl group, octynyl group,
Nonenyl group, decenyl group, undecenyl group, dodecenyl group, myristenyl group, pentadecenyl group, palmitenyl group, oleyl group, linole group, linolenyl group, arachidyl group, 2-ethylhexenyl group, phenyl group, 4-methylphenyl group, benzyl group , A p-methoxybenzyl group,
Decyloxyethylene group, pentyloxy (ethylene)
Examples include an _n- acetyl group and an acetyloxyethylene group. Particularly, as R ₁ , hydrogen, methyl, ethyl, propyl, isopropyl, butyl, octyl, 2-ethylhexyl, dodecyl, oleyl, decyloxyethylene, pentyloxy (ethylene) ₇ groups, A phenyl group, a benzyl group, an acetyl group, an acetyloxyethylene group and the like are preferable. Preferably, R _{2 to} R ₆ in the derivative are all hydrogen.

More specific examples of the derivative include, for example, 4-hydroxymethyl-1,3-dioxolan-2
-One, 4-methyloxymethyl-1,3-dioxolan-2-one, 4-ethyloxymethyl-1,3-dioxolan-2-one, 4-propyloxymethyl-1,
3-dioxolan-2-one, 4-isopropyloxymethyl-1,3-dioxolan-2-one, 4-butyloxymethyl-1,3-dioxolan-2-one, 4-
Octyloxymethyl-1,3-dioxolan-2-one, 4- (2'-ethylhexyl) oxymethyl-1,
3-dioxolan-2-one, 4-dodecyloxymethyl-1,3-dioxolan-2-one, 4-oleyloxymethyl-1,3-dioxolan-2-one, 4-decyloxyethyleneoxymethyl-1, 3-dioxolan-2-one, 4- pentyloxy (ethylene) _{7-oxy-1,3-dioxolan-2-one,} 4-phenyloxy-1,3-dioxolan-2-one,
4-benzyloxymethyl-1,3-dioxolan-2
-One, 4-acetyloxymethyl-1,3-dioxolan-2-one, 4-acetyloxyethyleneoxymethyl-1,3-dioxolan-2-one, and the like.

The compound of the formula (1) is, for example, alkylating the corresponding 4-hydroxymethyl-1,3-dioxolan-2-one,
_{When 2 to} R ₆ are all hydrogen, for example, a glycerin-1-ether derivative represented by the following formula (2)
It can be produced by reacting with dimethyl carbonate or diethyl carbonate in the presence of a basic catalyst.

[0011]

Embedded image

Wherein R ₁ is as defined above.

The above derivative has good properties as an oil agent, a humectant, a penetration aid, a solubilizing agent for an active ingredient, an emulsifier, etc., and is therefore used as an external preparation for the skin in a wide range of fields such as cosmetics and pharmaceuticals. Can be. In particular, when used as a moisturizer, it has little skin irritation, is familiar with the skin, has no stickiness, gives a refreshing or moist good feeling of use, and has a high moisturizing property.
Accordingly, the humectant composition of the present invention containing one or more of the present derivatives is, for example, a lotion, an emulsion, a skin cleanser, a toilet soap, a whitening cosmetic, a wrinkle improving cosmetic, a makeup cosmetic, a lipstick It can be advantageously used as cosmetics such as, or external medicines such as liquids, ointments and patches, and toothpastes. If necessary, the humectant composition of the present invention may contain other components as long as the moisturizing effect of the derivative is not impaired, and the dosage form may be any of a coating type, a patch type and the like.

In the humectant composition of the present invention, the compounding amount of the present derivative can be appropriately selected depending on the application and is not particularly limited, but is generally 1% by weight to 60% by weight, particularly 1% by weight. It is preferably set to と す る 40% by weight.
If the amount is less than 1% by weight, a sufficient feeling of use cannot be obtained, and if it exceeds 60%, stickiness is rather caused.

[0015]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention. (Examples 1 to 8) Lotion samples of Examples 1 to 8 and Comparative Example 1 were prepared according to the compositions and mixing ratios shown in Table 1. As a control sample, a lotion containing no moisturizing component (the present derivative or glycerin) among the components shown in Table 1 was prepared.

[0016]

[Table 1]

As the fragrances shown in Table 1, those having the following compositions were used. (Components) (parts by weight) Aldehyde C8 0.2 Aldehyde C9 0.2 Aldehyde C10 0.2 Aldehyde C11 0.2 Aldehyde C12 0.2 Aldehyde C12 MNA 0.2 Anisaldehyde 2.0 Acetal R 0.2 Adoxal 2 Acetyl Cedrene 2.0 Allyl Amyl Glycolate 0.2 Allyl Cyclohexane Propionate 2.0 Alpha Damascon 0.2 Beta Damascon 0.2 Delta Damascon 0.2 Ambrette Lid 0.2 Ambroxane 0. 2 amylcinamic aldehyde 20.0 amylcinamic aldehyde dimethyl acetal 2.0 amyl valerianate 0.2 amyl salicylate 2.0 isoamyl acetate 2.0 isoamyl salicylate 2.0 auranthiol 2.0 Cetyl eugenol 20.0 bakdanol 2.0 benzyl acetate 20.0 benzyl alcohol 2.0 benzyl salicylate 2.0 bergamyl acetate 0.2 bornyl acetate 2.0 butyl butyrate 20.0 p-tert-butylcyclohexanol 2. 0 paratertiary butyl cyclohexyl acetate 0.2 ortho tertiary butyl cyclohexanol 2.0 benzaldehyde 0.2 benzyl formate 0.2 caryophyllene 0.2 casimerane 2.0 carvone 2.0 cedulambar 2.0 cedril acetate 2 Cedrol 2.0 Celestrid 0.2 Thin alcohol Alcohol 2.0 Thin aldehyde 0.2 Cis jasmon 0.2 Citral 0.2 Citral dimethylaceta 2.0 Citrasal 2.0 Citronellal 0.2 Citronellol 2.0 Citronellyl acetate 2.0 Citronellyl formate 0.2 Citronellyl nitrile cycla set 0.2 Cyclamenaldehyde 20.0 Cyclaprop 20.0 Caron 0 .2 Coumarin 2.0 Cinnamyl acetate 2.0 Gamma-decalactone 0.2 Delta-decalactone 0.2 Dimethylbenzylcarbinol 2.0 Dihydrojasmon 0.2 Dihydrolinalool 2.0 Dihydromyrcenol 2.0 Dimethol 2 2.0 Dimyrcetol 2.0 Diphenyl oxide 0.2 Ethyl vanillin 0.2 Eugenol 2.0 Fluitate 2.0 Fentyl alcohol 0.2 Phenylethyl acetate 4.0 Galaxolide 20.0 Gamma Ndecalactone 0.2 Geraniol 20.0 Geranyl acetate 2.0 Geranyl formate 2.0 Geranyl nitrile 0.2 Hedion 20.0 Helional 0.2 Heliotropin 2.0 Cis-3-hexenol 0.2 Cis-3-hexenyl Acetate 0.2 cis-3-hexenyl salicylate 0.2 hexylcinnamic aldehyde 20.0 hexyl salicylate 2.0 phenylacetaldehyde dimethyl acetal 0.2 hydrotropic alcohol 0.2 hydroxycitronellal 2.0 indole 0.2 ionone 20.0 Isobornyl acetate 0.2 Isocyclocitral 0.2 IsoE super 2.0 Isoeugenol 0.2 Iononylacetate 0.2 Isobutylquinoline 0.2 Jasma Le 2.0 Jasmolactone 0.2 Jasmophylan 2.0 Koa Bon 2.0 2.0 Rigstral 0.2 Lilyal 20.0 Lime Oxide 0.2 Limonene 20.0 Linalool 20.0 Linalool Oxide 0.2 Linalool Acetate 2 0.0 Liral 20.0 Manzanate 0.2 Mayol 2.0 Mentyl acetate 2.0 Mensonate 2.0 Methyl anthranilate 2.0 Methyl eugenol 0.2 Menthol 0.2 Alpha methyl yonone 20.0 Beta methyl yo Non 2.0 gamma-methylyonone 20.0 methylisoeugenol 0.2 methyl lavender ketone 0.2 methyl salicylate 0.2 mugealdehyde 2.0 mugol 2.0 musk TM-II 2.0 musk 781 2.0 musk C14 2 0 Musk T 2.0 Musk ketone 0.2 Musktibetin 0.2 Musk moskene 0.2 Mirac aldehyde 2.0 Methylphenyl acetate 2.0 Nerol 2.0 Neryl acetate 2.0 Nopyr acetate 2.0 Nopyr alcohol 2 2.0 Neobergamate 2.0 Oak Moss No. 1 0.2 Oribbon 0.2 Oxyphenylone 0.2 Paralacyl methyl ether 0.2 Pentalid 2.0 Phenylethyl alcohol 20.0 Alphapinene 2.0 Lubafuran 0.2 Rosephenone 2.0 Rose oxide 2 Sandalore 2.0 Sandella 2.0 Santarex 2.0 Styril Real Acetate 2.0 Styril Real Propionate 2.0 Terpineol 20.0 Terpinyl Acetate 2.0 Tetrahydrolinalool 2.0 Tetrahydrolinalool Acetate 2.0 Tetrahydrogeraniol 2.0 Tetrahydrogeranyl acetate 2.0 Tonalid 20.0 Traseolide 2.0 Tripral 0.2 Thymol 0.2 Vanillin 0.2 Yarayara 0.2 Belldox 0.2 Ani Oil 0.2 Bay oil 0.2 Bodarose oil 2.0 Kananga oil 2.0 Cardamom oil 0.2 Cassia oil 0.2 Cedarwood oil 2.0 Orange oil 20.0 Mandarin oil 2.0 Tangerine oil 2.0 Basil Oil 0.2 Nutmeg oil 0.2 Citronella oil 0.2 Clove oil 0.2 Coriander oil 0.2 Elemiresinoid 2.0 Eucalyptus oil 0.2 Fennel oil 0.2 Galvanum oil 0.2 Geranium oil 2.0 Hiba Oil 2.0 Hinoki oil 2.0 Jasmine Absolute 0.2 Lavandin oil 2.0 Lavender oil 2.0 Lemon oil 2.0 Lemongrass oil 0.2 Lime oil 2.0 Neroli oil 0.2 Yuzu oil 0.2 Oak Moss Absolute 0.2 Tea Tree Oil 0.2 Patchouli Oil 2.0 Peppermint Oil 2.0 Perilla Oil 0.2 Petit Glen Oil 2.0 pine oil 0.2 rose oil 0.2 rosemary oil 0.2 camphor oil 0.2 fragrant oil 2.0 clary sage oil 0.2 sandalwood oil 0.2 spearmint oil 2.0 spike lavender oil 0.2 Star anise oil 0.2 Thyme oil 0.2 Tonka bean tincture 0.2 Turpentine oil 0.2 Vanilla bean tincture 0.2 Vetiver oil 2.0 Ylang-ylang oil 2.0 Grapefruit oil 2.0 Benzoin resinoid 0.2 Peru Balsam Resinoid 0.2 True Balsam Resinoid 0.2 Tuberose Absolute 0.2 Mustin tincture 0.2 Castorium tincture 0.2 Civet tincture 0.2 Ambergris tincture 0.2 Diethyl phthalate 100.0 Dipropylene glycol 100.0 Benzyl benzoate 100.0 isopropyl millimeter Tate 50.0 hercolyn 13.6 Total 1000.0

Each of the lotion samples was applied to the inner part of the forearm of 10 panelists, and the skin moisturizing performance and the feeling of use were evaluated by the following methods. (1) Skin moisturizing performance evaluation (skin keratin water content) For each of the samples of Examples 1, 2, 5, 6, and 8, the comparative example, and the control sample, the skin keratin water at the evaluation site of the panel was evaluated. The amount was measured using an impedance meter. The skin moisturizing performance was evaluated based on the following criteria. (Score) Significant effect: The measured value is 200% or more compared to the control sample
Effective: the measured value is 150% or more and 200% compared to the control sample
Less than somewhat effective: the measured value is 110% or more 15 compared to the control sample
Less than 0% Invalid: The measured value is less than 110% compared to the control sample
(Evaluation) ：: 80% or more of panelists evaluated highly effective, effective, and somewhat effective ○: 50% or more and less than 80% of panelists evaluated extremely effective, effective, and somewhat effective △: Excellent, effective 30% or more and less than 50% of panelists evaluated as slightly effective and ×: less than 30% evaluated as excellent, effective, and somewhat effective. Table 2 shows the evaluation results.

[0019]

[Table 2]

(2) Evaluation of Usability The usability when the panelists actually used the lotion samples having the compositions shown in Table 1 above was evaluated. The evaluation items were non-stickiness during use, non-stickiness after use, a refreshing feeling and a moist feeling, and were evaluated according to the following criteria. ◎: 8 or more out of 10 respondents are good ○: 6 to 7 out of 10 respondents are good △: 4 to 5 out of 10 respondents are good ×: 3 or less of 10 respondents are good Table 3 shows the evaluation results.

[0021]

[Table 3]

From the results in Tables 2 and 3, the lotion samples of Examples 1 to 8 containing the present derivative as a humectant were compared with the lotion samples of Comparative Example 1 containing glycerin as a humectant. Although the skin moisturizing performance is almost the same, it can be seen that the feeling of use is clearly superior to the lotion sample of the comparative example.

Example 9 Emollient Cream An emollient cream having the following composition was prepared. (All percentages are by weight.) Beeswax 2% Paraffin wax 3% Liquid paraffin 5% Stearic acid 3% 4-octyloxymethyl-1,3-dioxolan-2
-One 4% behenyl alcohol 3% polyoxyethylene (10EO) sorbitan monostearate 1% polyoxyethylene (40EO) sorbitan tetraolate 2% coconut oil fatty acid diethanolamide 0.5% methyl paraben 0.1% propyl paraben 0.1% Perfume (of the same composition as the perfume in Table 1) 0.5% purified water Remainder This emollient cream was evaluated for its moisturizing effect and feeling of use (non-stickiness and moist feeling after use). Was also ◎.

Example 10 Body Shampoo A body shampoo having the following composition was prepared. Glycerin ether sulfate 10% Na lauroyl glutamate 7% Coconut oil fatty acid diethanolamide 3% Ethylene glycol fatty acid ester 3% Ethanol 3% 4-isopropyloxymethyl-1,3-dioxolan-2-one 5% Dye and fragrance (of the same composition as the fragrance in Table 1) Appropriate amount Purified water Remainder This body shampoo was evaluated for its moisturizing effect and feeling of use (non-stickiness and moist feeling after use). The item was also ◎.

Example 11 Cleansing Gel A cleansing gel having the following composition was prepared. (All percentages are by weight.) Polyoxyethylene (20EO) octyldodecyl ether 15% Sorbitol 10% 4-hydroxymethyl-1,3-dioxolan-2-one 10% 4-decyloxyethyleneoxymethyl-1,3- Dioxolan-2-one 10% Tri-2-ethylhexanoic acid glyceride 15% Liquid paraffin 5% Purified water Remainder This cleansing gel was evaluated for its moisturizing effect and feeling of use (non-stickiness and moist feeling after use). , All evaluation items were ◎.

Example 12 Emulsion An emulsion having the following composition was prepared. (All percentages are by weight.) Monostearic acid (20EO) 1% Tetraoleic acid (40EO) 0.5% Monostearic acid 1% Batyl monoisostearate 1% Glycerin triisooctanoate 5% Butylparaben 0.1% Methylparaben 0.1% xanthan gum (2% aqueous solution) 7% 4-butyloxymethyl-1,3-dioxolan-2-
On 5% fragrance (of the same composition as the fragrance in Table 1) Appropriate amount Purified water Remainder This emulsion was evaluated for its moisturizing effect and feeling of use (non-stickiness and moist feeling after use). ◎

Example 13 Patch A patch having the following composition was prepared. (All percentages are by weight.) Water extract of Acacia catechu 0.1% Trimethylglycine 0.2% Grabradine 0.1% Polyacrylic acid 4.0% Sodium polyacrylate 1.5% Carboxymethylcellulose 4.0% 4-octyloxymethyl-1,3-dioxolan-2
-On 15.0% Sorbitol 10.0% Dihydroxyaluminum aminoacetate 0.1% Kaolin 0.05% Montmorinite 4.0% Polysorbate 80 1.0% 1,3-Brylene glycol 3.0% Dimethylpolysiloxane ( 30 cst) 1.0% Purified Water Residue The patch was evaluated for its moisturizing effect and feeling of use (non-stickiness and moist feeling after use), and all the evaluation items were ◎.

(Example 14) Lipstick A lipstick having the following composition was prepared. (% Is weight%) Titanium dioxide 4.5% Red 201 0.5% Red 202 2.0% Red 233 0.05% Celesin 4.0% Candelilla wax 8.0% Carnauba wax 2. 0% Castor oil 30.0% Diglyceride isostearate 39.95% Polyoxyethylene (25) polyoxypropylene (2
0) -2-Tetradecyl ether 1.0% 4-methyloxymethyl-1,3-dioxolan-2-
ON 3.0% UV inhibitor appropriate amount Antioxidant appropriate amount Fragrance appropriate amount Purified water 5.0% This lipstick was evaluated for its moisturizing effect (moist feeling) and good elongation. .

[0029]

The humectant composition of the present invention has the formula (1)
Since it contains a 1,3-dioxolan-2-one derivative represented by the formula, the skin is less irritating, has good adaptability to the skin, gives a good or moist feeling without stickiness, and has a high moisturizing effect. .

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Masayuki Toda 1-3-7 Honjo, Sumida-ku, Tokyo Inside Lion Corporation (72) Inventor Kaoru Suzuki 1-3-7, Honjo, Sumida-ku, Tokyo Within Lion Corporation (72) Inventor Nobuyuki Yamamoto 1-3-7 Honjo, Sumida-ku, Tokyo F-term within Lion Corporation (reference) 4C083 AA082 AA112 AA122 AB242 AB442 AC012 AC022 AC072 AC102 AC122 AC132 AC182 AC242 AC302 AC392 AC422 AC432 AC442 AC482 AC582 AC642 AC662 AC782 AC792 AC841 AC842 AC932 AD092 AD152 AD272 AD352 CC04 CC05 CC13 CC23 DD12 DD23 DD31 DD41 EE06 EE12

Claims (1)

[Claims] 1. A 1,3-geo represented by the following formula (1):
It is characterized by containing a xolan-2-one derivative
Humectant composition. Embedded image(Where R₁Is hydrogen; C₁~ C_{twenty two}Or within the range of
Unsaturated linear, branched or cyclic hydrocarbon groups;
An aromatic, heterocyclic ring or a substituent thereof is bonded to a hydrocarbon group.
Or a group of formula -R_a− (OR_a)_n-OR_bOr the formula-
(R_aO)_n-COR _b At R_aIs C_Two~ C_FourAl
A alkylene group which may be the same or different;_bBut
C₁~ C_{twenty two}Straight or branched, saturated or unsaturated within the range
Chain, or cyclic hydrocarbon group, or
A group to which an aromatic or heterocyclic ring or a substituent thereof is bonded;
Is an integer of 0 to 30;_Two~ R
₆Are each independently hydrogen; or C₁~ C_{twenty two}Within
Saturated or unsaturated, straight, branched or cyclic hydrocarbon
Elementary group. )