JPH10330729A - Solubilizer and cosmetic containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a solubilizer being inexpensive, being excellent in safety and stability and having good usability by using a specified acrylic resin alkanolamine. SOLUTION: This solubilizer consists of at least one compound having structural units represented by the formula [wherein R<1> and R<2> , which are independent of each other, are 1-24C alkyls; R' is a neutralizing agent or OH; and (m), (n), (p), (q) and (r) are arbitrary integers] and having a molecular weight of 10,000-300,000. A product obtained by adding the acrylic resin represented by the formula to a solvent can be desirably used. It is desirable that the solvent is at least one member selected among water, ethanol and polyhydric alcohols such as glycerol and 1,3-butylene glycol among which water or ethanol is especially desirable. When the compound of the formula is incorporated in a composition to form a solubilized composition, it is desirably used in an amount of 0.001-30 wt.% (in terms of the solid matter) based on the solubilized composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a solubilizer, and more particularly, to a solubilizer containing an alkanolamine of an acrylic resin and a cosmetic containing the same. The solubilizing agent of the present invention is suitably used particularly as a solubilizing agent for solubilizing fragrances, drugs (such as oil-soluble drugs) and the like.

[0002]

2. Description of the Related Art Hitherto, many studies on solubilization have been made, and many solubilizers have been developed. Solubilizers having particularly excellent stability have been widely used in the industrial field.

[0003]

However, nonionic surfactants containing polyoxyethylene chains such as polyoxyethylene oleyl ether, polyoxyethylene sorbitan oleate, polyoxyethylene hydrogenated castor oil, lauryl sulfate, etc. Anionic surfactants such as sodium, sodium dodecylbenzenesulfonate and potassium myristate are used as solubilizers, and these surfactants cannot always be sufficiently satisfied in terms of safety.

[0004] Therefore, in recent years, methods using polymer compounds which are considered to be safer than conventional surfactants have begun to be studied, but when these polymer compounds are used, the solubilization process is complicated. There are some problems, such as a high manufacturing cost.

[0005]

Means for Solving the Problems The inventors of the present invention have made intensive studies to solve the above problems, and as a result, it has been found that a specific acrylic resin alkanolamine works as a solubilizing agent.
The present inventors have found that a solubilizer that is inexpensive, has excellent safety and stability, and has good usability can be easily obtained by using this, and the present invention has been completed.

That is, the present invention provides a compound represented by the following general formula (I):

[0007]

Embedded image

(Wherein R ¹ and R ² each independently represent an alkyl group having 1 to 24 carbon atoms; R ′ represents a neutralizing agent or —OH; m, n, p, q, r Is an arbitrary integer), and has a molecular weight of 10,000.
A solubilizer consisting of one or more compounds of up to 300,000.

[0009] The present invention also relates to a solubilizing composition containing the above-mentioned solubilizing agent. Suitable examples of the solubilizing composition include cosmetics and the like.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.

The solubilizer of the present invention has the following general formula (I)

[0012]

Embedded image Or one or more compounds having a structural unit represented by

In the general formula (I), R ¹ and R ² each independently represent an alkyl group having 1 to 24 carbon atoms, and the number of carbon atoms is preferably 4 to 18. Also,
m, n, p, q, and r are any integers provided that the molecular weight of the compound is 10,000 to 300,000;
Preferably, it is an integer such that it becomes 25,000 to 200,000. If the molecular weight of the compound is too low, a sufficient effect of solubilization cannot be obtained, while if the molecular weight is too high, it becomes insoluble in a solvent, which is not preferable.

The compound having the structural unit represented by the above general formula (I), that is, the alkanolamine of acrylic resin is, for example, a copolymer of methacrylic acid, acrylic acid, methacrylic acid ester and acrylic acid ester represented by R ′. Neutralizing agents such as 2-amino-2-methyl-1,3-
It can be obtained by neutralizing with propanediol, 2-amino-2-methylpropanol, triethanolamine, triisopropanolamine, sodium hydroxide, potassium hydroxide or the like. However, an unneutralized one (R '= OH) can also be used.

The mode of the above-mentioned copolymer is arbitrary, and
For example, it may include any embodiment such as a block copolymer, a random copolymer, and a graft copolymer.

In the present invention, those containing the acrylic resin alkanolamine in a solvent are preferably used. As the solvent, one or more selected from polyhydric alcohols such as water, ethanol, isopropanol, glycerin, 1,3-butylene glycol, propylene glycol, and dipropylene glycol are preferably used. Among them, water and ethanol are preferably used.

When the above compound is compounded in a composition to form a solubilized composition, the compounding amount is preferably 0.001 to 30% by weight as a solid content in the solubilized composition, more preferably. Is 0.01 to 20% by weight, especially 0.5 to 10% by weight. If it is less than 0.001% by weight, a sufficient effect of solubilization cannot be obtained, while if it exceeds 30% by weight, gelation occurs, which is not preferable.

The acrylic resin alkanolamine used in the present invention has conventionally been used as a coating material for high-grade transparent paints, rubber, paper, cloth, and leather, and as a coating agent, a pasting agent, a fiber processing agent, an adhesive, and a setting agent. However, it has never been known that it can function as a solubilizing agent. The present inventors have found for the first time that these polymer compounds can function as solubilizers.

The solubilizing agent comprising the alkanolamine of the acrylic resin of the present invention is suitably used particularly as a solubilizing agent for solubilizing a fragrance, a drug (such as an oil-soluble drug) and the like.

[0020] The solubilized composition of the present invention may be used, in particular,
It is suitably used for solubilized cosmetics such as lotions, hair tonics, packs, and after shaving lotions.

When the solubilizing agent and the solubilizing composition of the present invention are used together with a fragrance component and the like, the solubiliser is superior in sustained release of the fragrance component as compared with the conventional solubilizing agent, and can maintain the fragrance for a long period of time. It also has the effect of making it possible. Therefore, by using the solubilizing agent and the solubilizing composition of the present invention, in addition to cosmetics such as perfume and cologne, indoor aromatic components (for example,
Linalool, geraniol, jasmine, citronellol) and the like can be used to improve the sustained release and sustainability of these components.

The solubilized composition and solubilized cosmetic of the present invention contain oils, surfactants, and the like which are usually added to the solubilized composition and solubilized cosmetic as long as the effects of the present invention are not impaired. , Humectants, ultraviolet absorbers, chelating agents, pH adjusters, anti-fading agents, preservatives, thickeners, dyes, pigments, fragrances,
Dyes, plasticizers, organic solvents and the like can be appropriately blended.

[0023]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto. In addition, the compounding amount is weight%.

I. Evaluation of solubilizer Samples 1 to 3 shown below were prepared.

(Sample 1) In the above general formula (I), alkanolamine (molecular weight 30,000) wherein R ¹ is a butyl group, R ² is a dodecyl group, and R ′ is 2-amino-2-methylpropanol )

(Sample 2) In the general formula (I), R ¹ is an ethyl group, R ² is an octadecyl group, a dodecyl group (octadecyl: dodecyl group = 1: 3), and R ′ is 2-amino-2.
Acrylic resin alkanolamine which is methylpropanol (molecular weight 100,000)

(Sample 3) In the general formula (I), R ¹ is an octadecyl group, R ² is a dodecyl group, and R ′ is 2-amino-
Acrylic resin alkanolamine which is 2-methylpropanol (molecular weight 40,000)

Using the above Samples 1 to 3 (solubilizing agents), the solubilizing ability, blemishes, defoaming properties and pH reduction were evaluated according to the following evaluation criteria. In addition, it evaluated using the surfactant conventionally used as a solubilizer as a comparative control product. Table 1 shows the results.

[Solubilizing Ability] A solubilizing agent (0.2 g), a preservative (0.1 g), and an oil-soluble drug (vitamin E acetate) are uniformly dissolved in ethanol (10 g). A composition was prepared. 7 of this system
The amount of the oil-soluble drug when the transmittance at 00 nm became 80% was evaluated in the following four steps. Evaluation ：: The same amount or more of the solubilizing agent amount ○: Half or more and less than the same amount of the solubilizing agent △: One-third or more and less than half the amount of the solubilizing agent ×: Less than one-third of the solubilizing agent amount

[Kasumi] After the solubilized composition used in the evaluation of the solubilizing ability was allowed to stand at 50 ° C for 4 weeks at room temperature, the state of kasumi formation was evaluated according to the following three grades. The term "foggy" refers to a state in which the system is slightly turbid and slightly fogged and defoamed. Evaluation ○: No blur Δ: Slight blur ×: Blurred

[Defoaming Property] 10 ml of a 1% aqueous solution of each sample was collected in a test tube and shaken vigorously for 30 seconds to evaluate the defoaming state in the following three steps. Evaluation ○: Excellent △: Good ×: Poor

[PH Reduction] The 1% aqueous solution of each sample was left at 50 ° C. for 2 months, and the pH reduction was evaluated in the following three steps. Evaluation ：: pH drop is less than 1 △: pH drop is 1 or more and less than 2 ×: pH drop is 2 or more

[0033]

[Table 1]

As is evident from the results in Table 1, it is understood that Samples 1 to 3 of the present invention are excellent in solubilizing ability and defoaming property, do not generate blemishes, and do not show a decrease in pH. . On the other hand, the conventional polyoxyethylene (30) hydrogenated castor oil has a high solubilizing ability, but is inferior to the product of the present invention in defoaming properties and pH reduction. In addition, polyoxyethylene (20) oleyl ether, polyoxyethylene (35) It can be seen that polyoxypropylene (20) glycol is inferior to samples 1 to 3 of the present invention in any of the evaluations of solubilizing ability, blemishes, defoaming properties, and pH reduction.

II. Examples (Example 1) Essence (preparation) (% by weight) Glycerin 5, 1,3-butylene glycol 5 Solubilizing agent for sample 1 (polymer solids) 1 Sequestering agent Proper amount Antifading agent Proper amount pH adjuster qs Perfume qs Preservative qs Purified water balance

Example 2 In Example 1, sample 2 was replaced by sample 2 in which the solubilizing agent (polymer solid content) 1% by weight was replaced by sample 2
A serum was prepared in the same manner as in Example 1, except that 1% by weight of the solubilizing agent (polymer solid content) was used.

(Example 3) In Example 1, sample 3 was replaced with 1% by weight of the solubilizer (polymer solid content) of sample 1.
A serum was prepared in the same manner as in Example 1, except that 1% by weight of the solubilizing agent (polymer solid content) was used.

Comparative Example 1 The procedure of Example 1 was repeated except that 1% by weight of polyoxyethylene (30) hydrogenated castor oil was used instead of 1% by weight of the solubilizing agent (polymer solid content) of Sample 1. A serum was prepared according to Example 1.

Comparative Example 2 The procedure of Example 1 was repeated, except that 1% by weight of polyoxyethylene (20) oleyl ether was used instead of 1% by weight of the solubilizing agent (solid polymer content) of Sample 1. A serum was prepared according to 1.

Comparative Example 3 In Example 1, 1% by weight of polyoxyethylene (35) polyoxypropylene (20) glycol was used instead of 1% by weight of the solubilizing agent (polymer solid content) of Sample 1. Except for the above, a serum was prepared according to Example 1.

[Stability] The above Examples 1 to 3 and Comparative Examples 1 to
The beauty serum prepared in 3 was allowed to stand at 50 ° C. and 5 ° C. for one month, and visually observed for overall evaluation. Evaluation ◎: The state was stable even after standing at 50 ° C. and 5 ° C. for one month. ○: The state was slightly stable after standing at 50 ° C. and 5 ° C. for one month. Δ: 50 ° C., and After leaving at 5 ° C. for 1 month, it became cloudy. ×: After leaving at 50 ° C. and 5 ° C. for 1 month, it became cloudy and oil floating was observed.

[Usability (freshness)] Professional panel 10
According to the name, the serums prepared in Examples 1 to 3 and Comparative Examples 1 to 3 were actually used, and a sensory test was performed for usability (freshness), and evaluated in the following four levels. Evaluation ◎: 8 or more out of 10 answered that the refreshing feeling was good ○: 6 to 7 out of 10 answered that the refreshing feeling was good Δ: 4 to 5 out of 10 answered that the refreshing feeling was good ×: 3 or less out of 10 answered that the refreshing feeling was good

[Usability (feeling familiar to skin)] The essence prepared in Examples 1 to 3 and Comparative Examples 1 to 3 was actually used by 10 professional panels, and the usability (fitting to skin) was used. Feeling)
Was subjected to a sensory test and evaluated in the following four stages. Evaluation ◎: 8 or more out of 10 responded that the feeling of familiarity with the skin was good ：: 6 to 7 out of 10 answered that the feeling of familiarity with the skin was good △: 4 to 5 out of 10 people ×: 3 or less out of 10 responded that skin familiarity was good.

[Usability (Moist feeling)] Professional panel 10
According to the names, the serums prepared in Examples 1 to 3 and Comparative Examples 1 to 3 were actually used, and a sensory test was conducted for usability (moistness), and evaluated on the following four levels. Evaluation ◎: 8 or more of 10 persons answered that the feeling of moisture was good ○: 6 to 7 persons of 10 answered that the feeling of moisture was good △: 4 to 5 of 10 persons answered that the feeling of moisture was good ×: 3 or less of 10 persons answered that the feeling of moisture was good.

[0045]

[Table 2]

As is evident from the results in Table 2, in Examples 1, 2, and 3 using the product of the present invention, a solubilized cosmetic having good usability and good stability can be obtained.

Example 4 Lotion (Preparation) (Weight%) 1,3-butylene glycol 4 glycerin 5 sorbitol 3 hyaluronic acid 0.1 octyl methoxycinnamate 0.05 vitamin E acetate 0.02 sample 2 Solubilizing agent (solid polymer content) 0.5 Ethanol 12 pH adjuster Appropriate amount Perfume Appropriate amount Preservative Appropriate amount Sequestering agent Appropriate amount Purified water balance Evaluation Solubilized cosmetic (lotion) of Example 4 After standing at 50 ° C., 50 ° C., and 5 ° C. for one month, the condition was stable, and the usability (freshness, familiarity with the skin, and moisture) was also good.

(Example 5) Hair tonic (preparation) (% by weight) Ethanol 55 Propylene glycol 4 Solubilizing agent for sample 3 (R '=-OH) 10 (Polymer solid content) Pyridoxine hydrochloride 0.03 Hinokitiol 0.02 Pantothenyl ether 0.2 Vitamin E acetate 0.15 pH adjuster Appropriate amount Coloring agent Appropriate amount Flavor Appropriate amount Purified water balance Evaluation The solubilized cosmetic (hair tonic) of Example 5 was 50 ° C.
The condition was stable even after standing at 5 ° C. for one month, and the usability (freshness, familiarity with the skin, and moisture) was also good.

III. Evaluation on Persistence and Sustained Release of Perfume 0.1 g of solubilizer, 0.01 g of perfume, and 0.1 g of preservative were uniformly dissolved in 1 g of ethanol, and this was added to purified water to make the total amount 100 g. Was prepared. A fixed amount of this composition (solution) was dropped on filter paper, and the intensity of the scent immediately after the addition and after 40 minutes was measured using a scent intensity measuring device (B & H Ala).
base EKW-8603) to evaluate the sustainability and sustained release of the fragrance. As the solubilizing agent, sample 3 of the product of the present invention, hydroxypropyl-β-cyclodextrin, which is conventionally known to have a sustained release effect, and polyoxyethylene (30) hydrogenated castor oil of a conventional product were used. FIG. 1 shows the measurement results.

As is apparent from the results shown in FIG. 1, Sample 3 which is the product of the present invention has a longer perfume sustainability and sustained release compared to hydroxypropyl-β-cyclodextrin and polyoxyethylene (30) hydrogenated castor oil. Was found to be excellent.

[0051]

As described in detail above, by using the solubilizing agent comprising the alkanolamine of the acrylic resin of the present invention, excellent solubilizing ability and defoaming property, excellent safety and stability, and excellent usability are obtained. The present invention provides a solubilized composition and a solubilized cosmetic which are excellent and excellent in sustained release and sustainability of a flavor component, a drug component and the like.

[Brief description of the drawings]

FIG. 1 is a graph showing the results of evaluation of the sustainability and sustained release of a fragrance component using the product of the present invention and a conventional product.

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Claims (6)

[Claims] 1. A compound represented by the following general formula (I) (Wherein, R ¹ and R ² each independently represent 1 to 2 carbon atoms)
R ′ represents a neutralizing agent or —OH; m, n, p, q, and r are arbitrary integers), and has a molecular weight of 10,000. ~ 300,0
A solubilizing agent comprising one or more compounds of the formula: 2. A solvent comprising one or more compounds having a structural unit represented by the above general formula (I) and having a molecular weight of 10,000 to 300,000. Solubilizer. 3. The solubilizer according to claim 2, wherein the solvent is at least one selected from water and polyhydric alcohols. 4. A solubilizing composition comprising the solubilizing agent according to claim 1. 5. The solubilizing composition according to claim 4, wherein the total amount of the solubilizing composition contains 0.001 to 30% by weight as a solid content of a solubilizing agent. 6. A cosmetic comprising the solubilizing composition according to claim 4 or 5.