JPH07316024A - Hair cosmetic - Google Patents

Abstract

PURPOSE:To obtain a hair cosmetic capable imparting the hair with smoothness, flexibility, favorable dampishness and humectancy, free from oiliness or stickiness, and causing hair squeakiness when the hair is wet. CONSTITUTION:This hair cosmetic contains a cyclic silicone compound of formula I (R<1>-R<3> each is methyl or phenyl; R<4> is the monovalent residue of an aliphatic polycyclic compound; A is a divalent linking group; (m) is 0-15; (n) is 1-15; where, (m+n) is >=3). In this compound, the aliphatic polycyclic compound in R<4> is e.g. a steroid compound (e.g. cholesterol), a diterpene compound (e.g. tetrahydroabietic acid); while the divalent linking group in A is pref. a group of formula II ((a) is 2-20), its carboxyl side being bound to R<4>. This hair cosmetic also contains a cationic surfactant (pref. a quaternary ammonium salt) and a lubricant. It is preferable that this hair cosmetic contain 0.1-20wt.% of the cyclic silicone compound, 0.5-5wt.% of the quaternary ammonium salt, and 1.0-10wt.% of the lubricant.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a hair cosmetic composition.
More specifically, it imparts smoothness, flexibility, good moisturizing and moisturizing properties to the hair, does not have an oily feeling or a sticky feeling, and does not cause a squeaky feeling when the hair is wet, a hair rinse, a hair conditioner, and a hair treatment. Etc. relating to hair cosmetics.

[0002]

2. Description of the Related Art Conventionally, in order to impart flexibility, smoothness, antistatic property, etc. to hair, a cationic surfactant has been used,
Hair cosmetics in combination with oils such as higher alcohols, glycerides, liquid paraffin and esters are used. In this case, by using these oil agents,
The flexibility and smoothness of hair can be improved as compared with the case where a cationic surfactant is used alone. But,
There is a drawback that the residual feeling of the oil agent, that is, the greasy feeling cannot be avoided.

Further, it has been proposed to use cholesterol as an oil agent used in combination with a cationic surfactant in order to improve the smoothness and glossiness of hair (JP-A-57-50911). However, the moist feeling of the hair was insufficient and the stickiness was not sufficiently suppressed. In addition, there is a drawback that the conditioning effect cannot be sufficiently improved because the adhesion to hair is insufficient.

Further, as compared with oil agents such as higher alcohols, glycerides, liquid paraffin, and esters, smoothness,
It is also practiced to incorporate silicones represented by a polymer of dimethylsiloxane, which can impart superior properties in terms of lubricity, dry feel and gloss, to hair cosmetics. However, such a hair cosmetic composition has a drawback in that it has an oily feeling (oily greasy feeling) peculiar to silicone. Moreover, since silicones generally have insufficient compatibility with water and other oil agents,
There is a problem in that the stability of the hair cosmetic during preparation and storage is insufficient. Hair cosmetics containing silicones have a strong squeaky feeling when the hair is wet, and
Since the adhesion to the hair is not sufficient, the moisturizing effect when the hair is dried becomes insufficient, and there is a problem that the moist feeling is lacking.

Therefore, as an oil agent for hair cosmetics using a cationic surfactant, a higher alcohol and 1 to 100 are used.
In combination with 0 cs of hydrophobic silicones (for example, aliphatic alcohol-modified polysiloxane) (JP-A-56
-92808), the combined use of a branched fatty acid cholesterol ester and dimethylpolyoxane has been proposed (Japanese Patent Application No. 5-196114).

[0006]

However, in the hair cosmetic composition disclosed in JP-A-56-92808, the smoothness of the hair after drying is improved, but the stickiness and wetness of the hair are improved. There was a problem that the squeaky feeling of time was not sufficiently improved.

Further, regarding the hair cosmetic composition disclosed in Japanese Patent Application No. 5-196114, it is possible to further improve the moisturizing feeling and flexibility of the hair and further suppress the oily feeling and sticky feeling. It was wanted.

By the way, it has been proposed to blend a silicone-modified sterol with a skin-protective cosmetic (Japanese Patent Laid-Open No. 4-145097). The sterol-modified silicones have good adhesion to the skin and can reduce the sticky feeling on the skin.
Therefore, it is considered that such a sterol-modified silicone is blended in a hair cosmetic composition in the expectation that the feel of the hair will be improved. However, these sterol-modified silicones have relatively high crystallinity because their main chains are linear. Therefore, the adhesion to hair is insufficient, and the function of retaining water on the hair (occlusive property) is also insufficient. Therefore, there is a problem in that the moisturizing feeling and the moisturizing property which are sustained in the hair cannot be realized.

The present invention is intended to solve the problems of the prior art as described above, and imparts smoothness, flexibility, and good moisturizing and moisturizing properties to hair, and also gives an oily feeling and tackiness. It is an object of the present invention to provide a hair cosmetic composition which does not have a feeling and does not cause a squeaky feeling when the hair is wet and when the hair is dry.

[0010]

Means for Solving the Problems The present inventor considers that the siloxane main chain of the silicone compound is cyclic and that the silicone compound and the aliphatic polycyclic compound such as cholesterol are separately blended in the hair cosmetic composition. However, they have found that the above object can be achieved by modifying cyclic silicones with an aliphatic polycyclic compound and compounding them into a hair cosmetic composition as a single compound, and have completed the present invention.

That is, the present invention is based on the formula (1)

[0012]

[Chemical 3] (In the formula, R ¹ , R ² and R ³ are independently a methyl group or a phenyl group, R ⁴ is a monovalent residue of an aliphatic polycyclic compound, and A is a divalent linking group. Yes, and m is 0 to 1
Is an integer of 5, and n is an integer of 1 to 15. However, m
And the sum of n is 3 or more. And a cyclic silicone compound represented by the formula (1).

The present invention will be described in detail below.

As shown in the formula (1), the siloxane main chain of the silicone compound used in the hair cosmetic composition of the present invention is cyclic rather than linear. By making it cyclic, the crystallinity of the silicone compound can be reduced and the adhesion (affinity) to hair can be improved.

In the compound of formula (1), R ⁴ is a monovalent residue of the aliphatic polycyclic compound. As the aliphatic polycyclic compound, it is preferable to use a compound that is hypoallergenic to hair and skin and has high affinity, and examples of such compounds include steroid compounds and diterpene compounds. You can Among these, steroid compounds are more preferable because they are widely distributed in the animal kingdom including humans. In particular, among steroid compounds, a sterol compound having a hydroxyl group can be preferably used because the hydroxyl group functions as a binding site when modifying the silicone compound. As the sterol compound having such a hydroxyl group, cholesterol, dihydrocholesterol, ergosterol, lanosterol, phytosterol, estradiol and the like can be preferably exemplified. Among them, cholesterol is preferably used from the viewpoint of easy availability. You can In addition, as a diterpene compound, tetrahydro abithienoic acid can be illustrated.

In the compound of the formula (1), A is a divalent linking group which connects the polysiloxane main chain and R ⁴ and is composed of carbon atoms, hydrogen atoms and oxygen atoms. In this case, A and the polysiloxane main chain are preferably linked by a carbon-silicon single bond that is easily formed by hydrosilylating a carbon-carbon double bond, while A and R ⁴ are usually It is preferable to connect with an ester bond or an ether bond which is easily formed by the esterification reaction or the etherification reaction.

Examples of such a linking group A include the following formulas (2) to (8).

[0018]

[Chemical 4] (In the above formula, a, b and c are each independently an integer of 2 to 20, d is an integer of 3 to 20, and e is an integer of 1 to 20). be able to.
Among them, the formula (2) which can be derived from a terminal unsaturated carboxylic acid as described below is preferable.

Next, in the compound of the formula (1), m is 0.
But it's okay. Further, if it exceeds 15, synthesis becomes difficult. Therefore, m is selected from an integer of 0 to 15. On the other hand, n is 0
If so, R ⁴ does not exist in the molecule, and if it exceeds 15, the crystallinity tends to be too high. Therefore,
n is selected from an integer of 1 to 15. In this case, if the sum of m and n is less than 3, it will be difficult to combine, so the sum of m and n should be 3 or more.

In the present invention, from the viewpoint of crystallinity,
The case where m is 0 is preferable. On the other hand, n is preferably 4 to 8 from the viewpoint of affinity for hair, and more preferably 4 or 5. Therefore, in the present invention, the case where m is 0 and n is 4 or 5 is particularly preferable.

The above-mentioned cyclic silicone compound used in the present invention can be produced by a known method. For example, when A is a linking group of formula (2) and R ⁴ is a cholesterol residue which is a kind of hydroxy group-containing steroid compound, first, as shown in the following reaction scheme, unsaturated carboxylic acid And cholesterol are linked by an esterification reaction. Then, the terminal unsaturated bond of the obtained ester compound (2a) can be obtained by hydrosilylation with a cyclic silicone compound having a hydrosilyl group by a conventional method.

[0022]

[Chemical 5] Similar to the case of the linking group of the formula (2), also in the case of the linking groups of the formulas (3) to (8), as shown in the following reaction scheme, the compound has a terminal unsaturated bond and cholesterol is an ester bond or Compounds (3a) to (8 linked by an ether bond)
a) is formed. Then, the terminal unsaturated bond of the obtained compound can be obtained by hydrosilylating a cyclic silicone compound having a hydrosilyl group by a conventional method.

[0023]

[Chemical 6]

[0024]

[Chemical 7]

[0025]

[Chemical 8]

[0026]

[Chemical 9]

[0027]

[Chemical 10]

[0028]

[Chemical 11] The hair cosmetic composition of the present invention does not have the effects of the present invention, ie, moisturizing feeling, moisturizing property, flexibility, oily feeling and tackiness,
Moreover, in order to achieve the effect of not causing squeaking when applied to wet hair, the cyclic silicone compound of the above formula (1) is preferably 0.1 to 50% by weight, more preferably 0.1 to 50% by weight. The content is 20% by weight.

The hair cosmetic composition of the present invention preferably contains a surfactant in addition to the cyclic silicone compound of the formula (1), and a known one conventionally used in hair cosmetic compositions is appropriately selected. Among them, it is preferable to use a quaternary ammonium salt. For example, it is described in JP-A-4-108719, page 3, upper right column, lower line 2 to page 4, upper left column, lower line 2. A quaternary ammonium salt or the like can be used.

The content of such a quaternary ammonium salt is usually 0.1 to 20% by weight, preferably 0.5 to 5% by weight in the hair cosmetic composition.

Further, it is preferable to add an oil agent generally used in hair cosmetics, for example, higher alcohols having a linear or branched alkyl group or alkenyl group, liquid paraffin, petrolatum, solid paraffin and the like. Hydrocarbons, lanolin derivatives, higher fatty acid esters,
Higher fatty acids, higher fatty acid amides, animal and vegetable fats and oils such as mink oil and olive oil can be used.

The content of these oil agents is usually 0.1 to 30% by weight, preferably 1.0 to 1 in the hair cosmetic composition.
It is 0% by weight.

The hair cosmetic composition of the present invention further comprises components that are usually added to cosmetics, such as other oil agents such as petrolatum, white pigments, extender pigments, color pigments, organic powders, pearl pigments and tar dyes. , Gelling agents, ultraviolet absorbers, antioxidants, preservatives, polyhydric alcohols, fragrances, beauty ingredients, water, etc. can be added. Further, a silicone derivative other than the cyclic silicone compound of the formula (1) can be added.

The hair cosmetic composition of the present invention can be produced by mixing the cyclic silicone compound of the formula (1) and, if necessary, other components with a conventional method.

The hair cosmetic composition of the present invention can be used in the same manner as in ordinary hair rinse, hair treatment, hair conditioner and the like. For example, the hair may be washed with a detergent such as shampoo, applied to the hair, and rinsed with warm water.

[0036]

The hair cosmetic composition of the present invention contains a cyclic silicone compound which is modified with an aliphatic polycyclic compound such as a steroid compound and has good adhesion to hair. This compound is hypoallergenic, non-greasy and has excellent water occlusive properties. Therefore, it imparts moistness and flexibility to the hair, has no oily feeling or tackiness, and does not cause a squeaky feeling when applied to wet hair.

[0037]

EXAMPLES The present invention will be specifically described below based on examples.

Reference Example 1 (Synthesis Example of Cholesterol Butyrate Modified Cyclic Silicone Compound) In a 300 ml flask equipped with a Dean-Stark trap, 116 g (0.3 mol) of cholesterol and 3 g of cholesterol were added.
28 g (0.33 mol) butenoic acid, 0.52 g (0.003 mol) p-toluenesulfonic acid and 15 toluene.
0 ml was charged. The mixture was heated and the esterification reaction was carried out for 5 hours under reflux of toluene. After completion of the reaction, the reaction mixture was washed twice with a 5% aqueous NaHCO ₃ solution and then twice with water. Then, the solvent was distilled off from the reaction mixture under reduced pressure, and the obtained residue was recrystallized from ethanol to obtain 66 g of cholesteryl 3-butenoate. The 1H-NMR spectrum chart and IR chart of this ester are shown in FIGS. 1 and 2, respectively.

Then, 33 g (0.073 mol) of cholesteryl 3-butenoate obtained, 4 g (0.017 mol) of tetramethylcyclotetrasiloxane (D4 '), 50 ml of toluene and 1% toluene / platinum chloroplatinate / 0.38 g of the hexanol mixed solution (10: 1) was charged into a 200 ml flask. This mixture was stirred at 60 ° C. for 2 hours to carry out a hydrosilylation reaction. After the reaction, activated carbon 1
g and 50 ml of ethanol were added, the mixture was stirred at 60 ° C. for 2 hours, and activated carbon and chloroplatinic acid were filtered off from the reaction mixture by suction filtration. The solvent was distilled off from the obtained filtrate under reduced pressure to obtain the compound of formula (9)

[0040]

[Chemical 12] (In the formula, Ch represents a cholesterol residue as defined in the above reaction scheme.) 35 g of a cyclic silicone compound having a structure was obtained. 1H of this compound
-The NMR spectrum chart and the IR chart are shown in FIGS. 3 and 4, respectively.

Reference Example 2 (Synthesis Example of Cholesterol Undecanoate Modified Cyclic Silicone Compound) In the same manner as in Reference Example 1 except that 10-undecenoic acid was used in place of 3-butenoic acid, the compound of formula (10) was used.

[0042]

[Chemical 13] A cyclic silicone compound having the structure of was obtained. The 1H-NMR spectrum chart and IR chart of this compound are shown in FIGS. 5 and 6, respectively.

Examples 1 to 7 and Comparative Examples 1 to 3 Hair cosmetics were prepared by uniformly mixing the compounding ingredients (% by weight) shown in Tables 1 to 6.

[0044]

[Table 1]

[0045]

[Table 2]

[0046]

[Table 3]

[0047]

[Table 4]

[0048]

[Table 5]

[0049]

[Table 6] For each of the obtained hair cosmetics, a hair conditioning effect (moisturizing feeling, flexibility, smoothness, oily feeling, squeaking feeling in a wet state) according to the following method
Was tested and evaluated.

Hair Conditioning Effect Test Method Japanese women 15 cm long hair (80 μm on average) 20
g was bundled, wound in a lot, and permed with a commercially available perming agent. After that, after washing with a commercial shampoo and rinsing with warm water, the hair rinse composition is applied to the whole and then 3
Rinse with running water for 0 seconds, wipe off water with a towel,
The degree of occurrence of a tingling sensation was evaluated by combing wet hair with a comb having a tooth spacing of 2 mm.

Next, the hair, which had been wiped off with a towel, was dried with a drier, and then evaluated for moistness, flexibility, smoothness and oiliness. The results are shown in Table 7.

Evaluation Standard Rank of "Moisture" State A Very moist B Moist C Somewhat moist D No moist

Evaluation Standard Rank of “Flexibility” State A Very soft B B Soft C Slightly hard D Hard

Evaluation Standard Rank of “Smoothness” State A Very smooth B B Smooth C Somewhat not smooth D Not smooth

Evaluation standard rank of “oilyness” State A When there is no oily feeling B When there is little oily feeling C When there is oily feeling D When there is very oily feeling

Evaluation Standard Rank of “Squeaky Feeling in Wet State” State A When there is no squeaky feeling B When there is a slight squeaky feeling C When there is a squeaky feeling D When there is a considerable squeaky feeling

[0057]

[Table 7] As is clear from Table 7, the hair cosmetic compositions of the examples impart moisturizing and softness to the hair, have no oily feeling or tackiness, and have a squeaky feeling when applied to wet hair. It did not occur and showed a favorable hair conditioning effect. In addition, it can impart a good silky feel to the hair and further prevent the hair from becoming dry. In addition, the scalp bulkiness could be suppressed. On the other hand, the hair cosmetics of Comparative Examples were inferior to the hair cosmetics of Examples in the evaluation items of the above-mentioned hair conditioning effect test.

[0058]

EFFECT OF THE INVENTION According to the hair cosmetic composition of the present invention, the hair is provided with a moisturizing feeling and a softness, and there is no oily feeling or sticky feeling, and a squeaky feeling is obtained even when applied to wet hair. Do not cause.

[Brief description of drawings]

FIG. 1 is a 1H-NMR spectrum chart of cholesteryl 3-butenoate.

FIG. 2 is an IR chart of cholesteryl 3-butenoate.

FIG. 3: 1 of cholesteryl butanoate-modified cyclic silicone
It is a H-NMR spectrum chart figure.

FIG. 4 I of cholesteryl butanoate modified cyclic silicone
It is an R chart figure.

FIG. 5 is a 1 H-NMR spectrum chart of cholesteryl undecanoate-modified cyclic silicone.

FIG. 6 is an IR chart of cholesteryl undecanoate-modified cyclic silicone.

Claims (8)

[Claims] 1. Formula (1): (In the formula, R ¹ , R ² and R ³ are independently a methyl group or a phenyl group, R ⁴ is a monovalent residue of an aliphatic polycyclic compound, and A is a divalent linking group. Yes, and m is 0 to 1
Is an integer of 5, and n is an integer of 1 to 15. However, m
And the sum of n is 3 or more. ) A hair cosmetic containing a cyclic silicone compound represented by 2. The hair cosmetic composition according to claim 1, wherein m is 0. 3. The hair cosmetic composition according to claim 1, wherein n is 4 to 8. 4. The hair cosmetic composition according to claim 1, wherein the aliphatic polycyclic compound represented by R ⁴ is a steroid compound. 5. The hair cosmetic composition according to claim 4, wherein the steroid compound is cholesterol. 6. The divalent linking group of A has the formula (2): (Wherein a is an integer of 2 to 20), and the carboxyl group side thereof is bonded to a monovalent residue of the aliphatic polycyclic compound. Cosmetics. 7. The hair cosmetic composition according to claim 1, further comprising a cationic surfactant and an oil agent. 8. The hair cosmetic composition according to claim 7, wherein the cationic surfactant is a quaternary ammonium salt.