JPH10279918A - Solubilizing agent and cosmetic containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the solubilizing agent capable of an exhibiting excellent low cost, safety, stability and usability, capable of being simply produced and useful for solubilizing perfumes, medicines, etc., by using a (meth)acrylate ester copolymer having a specific betaine structure. SOLUTION: This solubilizing agent comprises (A) a compound having structural units of the formula [R<1> is a 1-24C alkyl; R<2> is H, methyl; (m) is 20-90 wt.%; (n) is 10-80 wt.%] (preferably having a mol.wt. of 10000-400000). The compound A is contained e.g. in a solvent such as water or a polyhydric alcohol. The compound A is obtained e.g. by copolymerizing N-methacryloyloxyethyl N,N-dimethylammonium-α-N-methylcarboxybetaine with an alkyl methacrylate ester.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a solubilizer, and more particularly, to a solubilizing agent for N- (meth) acryloyloxyethyl N, N-dimethylammonium-.alpha.-N-methylcarboxybetaine. The present invention relates to a solubilizing agent containing a polymer and a cosmetic containing the same. The solubilizing agent of the present invention is suitably used as a solubilizing agent for solubilizing fragrances, 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]

The present inventors have made intensive studies to solve the above problems, and as a result, have found that certain N- (meth) acryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaines have been developed. -The (meth) acrylic acid alkyl ester copolymer acts as a solubilizing agent, and by using this, a solubilizing agent that is inexpensive, has excellent safety and stability, and has good usability can be easily obtained. This led to the completion of the present invention.

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

[0007]

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(Wherein, R ¹ represents an alkyl group having 1 to 24 carbon atoms; R ² represents a hydrogen atom or a methyl group;
m represents 20 to 90% by weight; n represents 10 to 80% by weight).

[0009] The present invention also relates to a solubilizing composition containing the above compound. As the solubilizing composition, cosmetics and the like are preferably exemplified.

[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]

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One or more compounds having a structural unit represented by the formula:

In the general formula (I), R ¹ represents an alkyl group having 1 to 24 carbon atoms, and the number of carbon atoms is preferably 4 to 18. Also, m is 20 to 90% by weight.
And preferably 30 to 80% by weight. n is 10
-80% by weight, preferably 20-70% by weight.

The molecular weight of the above compound is 10,000.
It is preferably from about 400,000 to about 400,000, more preferably from 30,000 to 250,000. If the molecular weight 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.

A compound having a structural unit represented by the above general formula (I), that is, N- (meth) acryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine. (Meth) acrylic acid alkyl ester The copolymer is obtained, for example, by copolymerizing N-methacryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine with an alkyl methacrylate. The mode of the above-mentioned copolymer is arbitrary, and may include any mode such as a block copolymer, a random copolymer, and a graft copolymer.

In the present invention, the N- (meth) acryloyloxyethyl N, N-dimethylammonium-α-N-
Those containing a methylcarboxybetaine / alkyl (meth) acrylate copolymer 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, ethanol is most preferred.

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, particularly 0.05 to 10% by weight. If the content is less than 0.001% by weight, a sufficient effect of solubilization cannot be obtained.
If the content is more than weight%, gelation occurs, which is not preferable.

N- (meth) acryloyloxyethyl N, N-dimethylammonium-α-N- used in the present invention
Methylcarboxybetaine / (meth) acrylic acid alkyl ester copolymers have been conventionally used as setting agents, coating agents and the like, but it has never been known that they can function as solubilizers. For the first time, the inventors have found that these copolymers can function as solubilizers.

In the present invention, N- (meth) acryloyloxyethyl N, N-dimethylammonium-α-N-
A solubilizing agent comprising a methylcarboxybetaine / alkyl (meth) acrylate copolymer is suitably used as a solubilizing agent for solubilizing a fragrance, a drug and the like.

The solubilizing composition of the present invention is particularly useful
It is suitably used for solubilized cosmetics such as lotions, hair tonics, packs, and after shaving lotions.

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) N-methacryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine / stearyl methacrylate copolymer

(Sample 2) N-methacryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine / stearyl methacrylate / butyl acrylate copolymer

(Sample 3) N-acryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine / butyl methacrylate copolymer Using the above Samples 1 to 3 (solubiliser), the following evaluation was carried out. The solubilizability, blemishes, defoaming properties, and pH reduction were evaluated based on 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] 0.2 g of a solubilizing agent, 0.1 g of a preservative, and an oil-soluble drug (vitamin E acetate) are uniformly dissolved in 10 g of ethanol, and the resulting solution is added to purified water to make the total amount 100 g and solubilized. 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 solubilizing ability was allowed to stand at 50 ° C for 4 weeks at room temperature, the state of kasumi formation was evaluated by the following three steps. 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 the defoaming state after vigorously shaking for 30 seconds was evaluated in the following three steps. Evaluation ○: Excellent △: Good ×: Poor

[PH Reduction] A 1% aqueous solution of each sample was allowed to stand 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

[0032]

[Table 1] Table 1 As is clear from the results in Table 1, Sample 1 which is the product of the present invention
Nos. 3 to 3 are excellent in solubilizing ability and defoaming property, show no occurrence of blemishes, and show no 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) Polypropylene (20) glycol has solubilizing ability, blemishes, defoaming properties, pH
In any of the evaluations of the decrease, Sample 1 which is the product of the present invention
It turns out that it is inferior to 3.

II. Examples (Example 1) Essence (preparation) (weight%) Glycerin 5, 1,3-butylene glycol 5 Solubilizer of sample 1 (polymer solid content) 1 Ethanol 10 Arbutin 0.1 Olive oil 0.05 Hydroxy Ethyl cellulose 0.15 Sequestering agent Suitable amount Anti-fading agent Suitable amount pH adjuster Suitable amount Perfume proper amount Preservative proper amount Purified water balance

(Example 2) In Example 1, sample 2 was replaced with 1% by weight of the solubilizing agent (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.

Example 3 A sample 3 was prepared in the same manner as in Example 1 except that the solubilizing agent (polymer solid content) of Sample 1 was 1% by weight.
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 in place 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

[0041]

[Usability (feeling familiar to skin)] The essences prepared in Examples 1 to 3 and Comparative Examples 1 to 3 were 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.

[0044]

[Table 2] Table 2 As is clear 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) (Weight%) Ethanol 55 Propylene Glycol 4 Solubilizer for Sample 3 (Polymer Solids) 10 Pyridoxine Hydrochloride 0.03 Hinokitiol 0.02 Pantothenyl Ether 2 Vitamin E acetate 0.15 pH adjuster qs colorant qs perfume qs Purified water balance evaluation The solubilized cosmetic (hair tonic) of Example 5
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.

[0047]

As described in detail above, according to the present invention, N
-(Meth) acryloyloxyethyl N, N-dimethylammonium-α-N-methylcarboxybetaine.
Using a (meth) acrylic acid alkyl ester copolymer solubilizer, it has excellent solubilizing ability and defoaming properties,
Solubilizing composition with excellent safety, stability and good usability,
A solubilized cosmetic is provided.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI C08L 33/04 C08L 33/04

Claims (6)

[Claims] 1. A compound represented by the following general formula (I) (Wherein, R ¹ represents an alkyl group having 1 to 24 carbon atoms; R ² represents a hydrogen atom or a methyl group;
90% by weight; n represents 10 to 80% by weight). 2. The solubilizer according to claim 1, wherein one or more compounds having the structural unit represented by the general formula (I) are contained in a solvent. 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 method according to claim 4, wherein the total amount of the solubilized composition contains 0.001 to 30% by weight of a compound having a structural unit represented by the general formula (I) as a solid content. Solubilized composition. 6. The solubilizing composition according to claim 4, which is a cosmetic.