JPH03170518A - New copolymer and cosmetic containing the same - Google Patents

Abstract

PURPOSE:To improve the safety, emollient effect, and moisture effect on the skin, water repellency, and feel in use by copolymerizing a specific dimethylpolysiloxane compd. with N-vinyl pyrrolidone. CONSTITUTION:A new copolymer, having a wt.-average mol.wt. of 3000-500000, is obtd, by copolymerizing 5-80mol% dimethylpolysiloxane compd. pref. of the formula (wherein R1 is H or CH3; R2 is a 1-10C divalent hydrocarbon group optionally interrupted by 0; (m) is 0-2; and (n) is an average degree of polymn. and 0-200) having a radical-polymerizable group at its one molecular terminal, 2-60mol% N-methylpyrrolidone, and if necessary a monomer copolymerizable with those two monomers at 50-180 deg.C in the presence of a radical polymn. initiator. The copolymer is compounded into a cosmetic as its base material in an amt. of 1-100wt.%.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention is directed to a copolymer having a pyrrolidone group and a specific dimethylpolysiloxane chain, and a copolymer containing the copolymer that has excellent affinity and safety for skin and hair. , relates to a cosmetic having good feeling and ease of use.

[Conventional technology]

Conventionally, cosmetics have been prepared by selecting a base depending on the required properties and combining it with other ingredients to take advantage of the characteristics of the base. For example, when a moisturizing effect is required, water, aqueous ingredients, moisturizing agents, etc. are blended to provide an emollient effect. When fruit is required, it is prepared using an oily base as the backbone. In addition, if both moisturizing and emollient effects are required, a combination of two bases may be blended, or an oily base may be blended with a hydrophilic group such as a hydroxyl group or an amide group introduced into the molecule. Attempts are being made. Additionally, for products expected to be water repellent, a base such as silicone oil is added.

[Problem to be solved by the invention]

However, when several bases are combined, the characteristics of each base may cancel each other out.

Further, at present, there is no cosmetic that satisfies all of the following: high safety for the skin, emollient effect, moisturizing effect, water repellency, and good feel when used.

Therefore, it has been desired to develop a base that has all of the above properties and a cosmetic containing the same.

[Failure to solve the problem]

Under these circumstances, the present inventors conducted intensive research and found that copolymers containing pyrrolidone groups and specific dimethylpolysiloxane groups are highly safe to the skin, and have emollient effects, moisturizing effects, and water repellency. The present invention was completed by discovering that the present invention is a base that has good properties and feels good when used, and that cosmetics containing it also have similarly excellent properties and feel when used.

That is, the present invention provides a copolymer obtained by copolymerizing a dimethylpolysiloxane compound (A) having a radically polymerizable group at one end of the molecular chain and N-vinylpyrrolidone (B), and a cosmetic containing the copolymer. It provides:

Preferred examples of the compound (A) used in the present invention include those represented by the following general formula (1).

(1) Rl: hydrogen atom or methyl group R2: carbon number 1 to 10, which may be interrupted by an oxygen atom
divalent hydrocarbon group m: 0, 1 or 2 n: number from 0 to 200 representing the average degree of polymerization The compound represented by the above general formula (1) is specifically, for example, the compound represented by the following general formula (2 ) can be obtained by subjecting a (meth)acrylate-substituted chlorosilane compound represented by formula (3) to a terminal hydroxyl-substituted dimethylpolysiloxane represented by general formula (3) to a dehydrochloric acid reaction according to a conventional method. It is not limited to this.

R, (wherein R1, Lx m and n have the same meanings as above) Among the compounds (A), specific examples of those preferably used include those shown below.

CH3 ■ CH3 C}I. =C(CL)CDOCH=S+ (C}I-)
1N-vinylpyrrolidone (B) is represented by the following chemical formula (4).

Cll. =CH The copolymer of the present invention can be obtained by copolymerizing the above compounds (A) and (B), using other radically polymerizable monomers as necessary. Here, the compound (A) in the total amount of radically polymerizable monomers
The ratio of (B) and (B) varies depending on the type of compound (A), but cannot be determined unconditionally, but generally the ratio of compound (A) is 5 to 80%.
Mol%, especially 1O to 60 mol% is preferable, and compound (B
) is preferably 2 to 60 mol%, particularly 5 to 40 mol%. If the amount of compound (A) is less than 5 mol %, water repellency and soft feel will be lacking, and if it is more than 80 mol %, satisfactory emollient effect and moisturizing effect will not be obtained. Furthermore, if the amount of compound (B) is less than 2 mol%, satisfactory emollient and moisturizing effects cannot be obtained, and furthermore, the affinity for the skin is lost.
On the other hand, if it exceeds 60 mol%, water repellency will be poor.

Other radically polymerizable monomers that may be used as necessary include styrene, substituted styrene, vinyl acetate, (meth)acrylic acid, (meth)acrylic ester, maleic anhydride, maleic ester, and fumaric ester. , vinyl chloride, vinylidene chloride, ethylene, brobylene, butadiene, acrylonitrile, fluorinated olefin and the like.

If a large amount of methyl methacrylate is added, the properties of the copolymer obtained will be similar to that of acrylic resin, with good film forming properties and film retention. When a large amount of acrylic ester is added to the copolymer, the resulting copolymer becomes an extractant with a soft feel.

Copolymerization of the above compounds (A), (B) and other radically polymerizable monomers is carried out in the presence of a conventional radical polymerization initiator such as penzoyl peroxide, lauroyl peroxide, azobisisobutyronitrile, Any of solution polymerization, emulsion polymerization, turbidity polymerization, and bulk polymerization can be applied.

Among these, the solution polymerization method is a preferred method because it is easy to adjust the molecular weight of the obtained copolymer to an optimum range. The solvents used here include benzene,
Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone and methyl isobutyl ketone;
Examples include one or a mixture of two or more esters such as ethyl acetate and isobutyl acetate.

In addition, this polymerization reaction has a reaction temperature of 50 to 180°C,
Particularly preferably, it is carried out within the range of 60 to 120°C, and it can be completed in about 5 to 10 hours under this temperature condition.

When the compound (1) is used as the compound (A), the copolymer of the present invention produced as described above has a structure having the following units (a) and (w) in the molecule.

(a) R (wherein R1, R,, m and n have the same meanings as above) (b) BCH. -CH? When using the copolymer of the present invention as a cosmetic base, G
Weight average molecular weight in terms of polystyrene determined by PC: approximately 3. 0
00-500,000, more preferably 5. 000
~200. It is preferable to use a value in the range of 000.

Cosmetics prepared by blending the copolymer of the present invention include basic cosmetics for the face and hands and feet such as creams and emulsions; hair cosmetics such as hair styling products and hair treatments; foundations, white powders, blushers, Make-up cosmetics such as eye shadows and lipsticks may be mentioned, but any material to which the copolymer of the present invention can be applied may be used.

The amount of the copolymer of the present invention in cosmetics is 1 to 100.
% by weight is preferred, and in addition to the copolymer, commonly used cosmetic ingredients can be blended depending on the product type or cosmetic purpose. Examples of such cosmetics include oil ingredients such as fats and oils, waxes, hydrocarbons, fatty acids, alcohols, esters, lanolin, and silicone oils, powder ingredients such as white pigments, colored pigments, and extender pigments, and metal soaps. , surfactant, polyhydric alcohol, polymer compound, water, antioxidant,
Examples include ultraviolet absorbers, preservatives, tar pigments, beauty products, and fragrances.

〔Example〕

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.

Example 1 Copolymer A In a glass reactor equipped with a thermometer and a reflux condenser, 160 g of a compound represented by the following chemical formula, N-vinylpyrrolidone 2.
2g, 600g of }luene, and 5g of azobisisobutyroni}IJ were charged, and the mixture was stirred while maintaining the internal temperature at 110 to 115°C, and a copolymerization reaction was carried out for 8 hours.

After cooling, an excess amount of methyl alcohol was added, and the polymer was precipitated and washed several times to obtain about 170 g of a colorless viscous liquid. This colorless viscous liquid was found to be carbon-42 by qualitative tests and infrared absorption spectra.
．． 78%, hydrogen 8.92%, nitrogen O, 60%,
By matching the calculated theoretical value, it was confirmed that the copolymer had dimethylpolysiloxane groups and pyrrolidone groups in its side chains.

The molecular weight of this product was approximately 9,700 as determined by GPC as a polystyrene equivalent weight average molecular weight.

Example 2 Copolymer B Using 190 g of a compound represented by the following chemical formula, 50 g of 2-ethylhexyl acrylate, 10 g of SN-vinylpyrrolidone, 750 g of toluene, and 5 g of azobisisobutyronitrile,
The same procedure as in Example 1 was carried out to obtain about 245 g of a colorless viscous liquid.

The molecular weight of this product was determined in the same manner as in Example 1, and was approximately 66.
It was 000.

Example 3 Copolymer C 57.5 g of a compound represented by the following chemical formula, t-butylacryl}
2.5 g, N-vinylpyrrolidone 1.5 g, }luene 100 g and azobisisobutyronitrile 0. 5g
An approximately viscous liquid was obtained using the same procedure as in Example 1.

Example 4 Copolymer D Chemical formula below 5 4 g colorless 71.8g of the compound represented by acrylate 6. 6g, methyl meth Vinylpyrrolidone 4, Og, Azobisisobutyronitri Operate in the same way as 1 to get about 71 Ta.

The molecular weight is there were.

Example 5 Hair treatment tome (Bokubun) (1) Copolymer B It was measured in the same manner as in Example 1, and it was about 61,000, using 7.2 g of 2-ethylhexylacrylate and 300 g of toluene and 0.5 g of 1N toluene. Colorless viscous liquid of Example g was obtained (parts by weight) 4.0 (5) 1.3-butylene glycol 2.0 (6
) Ethyl alcohol 50.0 (7
) Purified water 23. 97 (8
) Sodium chloride 0.03 (manufacturing method) A. After dissolving (8) in (7), add (5) and (6).

B. (1) to (4) are uniformly dissolved.

C. Mix A and B to create a two-layer hair treatment.

Comparative Example 1 A hair treatment was obtained in the same manner as in Hair Treatment Example 5, except that 4 parts by weight of dimethylpolysiloxane (average degree of polymerization 5000) was used instead of a certain amount (1).

Regarding the hair treatments of Example 5 and Comparative Example 1,
A usage test was conducted by a panel of 30 women, and evaluation was made according to the following criteria.

The results are shown in Table 1.

Evaluation score: Very good Good to Fairly poor Average score: 2.5 or more 2.0 or more, less than 2.5 1.5 or more, less than 2.0, less than 1.5 Table 1 3 points 2 points 1 point 20: ○: △ : × From the results shown in Table 1, it was demonstrated that the hair IJ-toment containing the copolymer of the present invention was superior in feel and usability compared to comparative products.

Example 6 Emulsion (part) (parts by weight) (1
) N-acylglutamic acid 0.1(2)1
．． 3-Butylene glycol 0.4 (3) Glycerin monofatty acid ester 0.5 (4) Setanol 0.5 (5) Geiro l,0 (6) Macadamian nut oil 6.0 (7) Liquid paraffin 3,0 ( 8) Copolymer D
4.0(9) Sodium hydroxide 0. 025α. 1) 1,3-
Butylene glycol 15.000 Seikai water
69. 475 (Production method) A. After dissolving (1) in (2) by heating, add (3) to (8) and bring the temperature to 75°C.

Bl9) to Ql) are uniformly dissolved at 75°C.

C. Add B to A and emulsify.

D2 Cool to make emulsion.

The emulsion obtained above had good emollient effect and moisturizing effect, and also had water repellency, and was excellent in feel and usability.

Example 7 The copolymers of Examples 1 to 4 were tested using a patch test method to confirm safety. As a result, no abnormalities such as erythema were observed, and it was confirmed that the copolymers were highly safe.

〔Effect of the invention〕

As detailed above, the copolymer of the present invention has a high affinity for the skin, has good emollient effect and moisturizing effect, and has water repellency and an excellent feel when used. By using it as a cosmetic base, extremely useful cosmetics that exhibit its properties can be obtained.

that's all

Claims (1)

[Scope of Claims] 1. A copolymer obtained by copolymerizing a dimethylpolysiloxane compound having a radically polymerizable group at one end of its molecular chain and N-vinylpyrrolidone. 2. A cosmetic containing the copolymer according to claim 1.