JPH0741417A - Composition for hair treatment - Google Patents

Abstract

PURPOSE:To obtain a hair-treatment composition giving low stimulation to the scalp without deteriorating the effect of ammonium salt by using a quaternary ammonium salt in combination with an organopolysiloxane derivative having a specific sugar residue. CONSTITUTION:This hair-treatment composition giving low stimulation to the scalp without deteriorating the effect of ammonium salt is produced by combining (A) an organopolysiloxane derivative having sugar residues and expressed by the formula I [R and R<a> are each 1-8C hydrocarbon group; at least one of R<1> to R<6> is organic group of the formula II (R<7> is 2-20C organic group; G is a sugar residue derived from monosaccharide, oligosaxccharide or polysaccharide) and the others are each 1-8C hydrocarbon group or OH; average of (m) and (n) is 0 or positive number and m+n is 1-1000] with (B) a quaternary ammonium salt. The compound of the formula I is e.g. the compound of the formula III (G is a glycosyl) and the quaternary ammonium salt is e.g. palmityl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, or the like.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair treatment composition, and more particularly to a reduction in skin irritation of a hair treatment composition containing a quaternary ammonium salt.

[0002]

2. Description of the Related Art Usually, hair is covered with sebum secreted from the scalp and animal and vegetable oils and fats derived from hair creams, hair oils, etc. Will be removed. For this reason, the hair after washing has lost its smoothness, has a dry and hard feel, and has difficulty in combing and tends to cause split hairs and split ends.

Further, as the use of perms, hair colors or bleaches has become more common due to the improvement of "fashion consciousness" as in recent years, hair damage is further advanced,
The above phenomenon is promoted. In order to reduce or eliminate such a phenomenon caused by hair damage, various hair treatment compositions have been developed as a treatment agent after washing hair. These hair treatment compositions usually contain a quaternary ammonium salt as a main component, and there are some poorly soluble quaternary ammonium salts and easily soluble quaternary ammonium salts.

[0004]

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention A hair treatment solution composition using a readily water-soluble quaternary ammonium salt has the advantage that it is easy to obtain a transparent one, while imparting smoothness to the hair. It has a dull, hard feel and is less effective in improving combing. On the other hand, a sparingly water-soluble hair treatment composition has been blended with a surfactant having a high HLB in order to make it transparent. However, due to the influence of this surfactant, the adsorption of poorly water-soluble quaternary ammonium salt on the hair is inhibited, and the quaternary ammonium salt is said to have excellent sensation of finish and crease and tangling of the hair after washing. There was a problem that the original effect would not be exhibited.

A solution containing only a quaternary ammonium salt may have skin irritation, and it is desired to reduce the irritation. The present invention has been made in view of the above problems of the prior art, and an object thereof is to provide a hair treatment composition having excellent usability and reduced skin irritation which a quaternary ammonium salt has.

[0006]

Means for Solving the Problems As a result of intensive investigations by the present inventors in order to achieve the above-mentioned object, by using an organopolysiloxane derivative having a specific sugar residue together with a quaternary ammonium salt, The inventors have found that a hair treatment composition having a low skin irritation can be obtained without impairing the hair treatment effect of the quaternary ammonium salt, and completed the present invention.

That is, the hair treatment composition according to claim 1 of the present invention has the following general formula 3

[Chemical 3] [Among the chemical formula 3, R and R ^a each show the same or different hydrocarbon group having 1 to 8 carbon atoms. R ^{1 to} R ⁶ are the same or different, and at least one is represented by the general formula 4

Embedded image -R ⁷ -O-G (in Formula 4, R ⁷ represents an organic group having 2 to 20 carbon atoms, G represents a sugar residue derived monosaccharide, oligosaccharide or polysaccharide.) Represents an organic group represented by
Represents a hydrocarbon group or a hydroxy group. The average value of m and n shows the same or different 0 or a positive number, and 1 ≦ m +
n ≦ 1000. ] One or more kinds of the organopolysiloxane derivative having a sugar residue represented by the above and one or more kinds of the quaternary ammonium salt are blended.

The structure of the present invention will be described in more detail below.
It Organopolysiloxane containing sugar residue shown in Chemical Formula 3 above
In the derivative, R and R^aAre the same or different carbon numbers
1-8 hydrocarbon groups, methyl group, ethyl group, butyl group
And a phenyl group or the like. Also, R⁷so
Examples of the organic group having 2 to 20 carbon atoms shown include-(C
H₂)₂-,-(CH₂)₃-,-CH₂CH (CH₃) CH
₂-,-(CH₂)_Four-,-(CH₂)_Five-,-(CH₂)₆
-,-(CH₂)₇-,-(CH₂)₈-,-(CH₂)₂−
CH (CH₂CH₂CH₃)-,-CH₂-CH (CH₂C
H₃)-,-(CH₂)₃-O- (CH₂)₂-,-(C
H₂)₃-O- (CH₂)₂-O- (CH₂)₂-,-(CH
₂) 3-O-CH₂CH (CH₃)-,-CH₂-CH (C
H₃) -COO (CH₂)₂-Can be exemplified
It

In the present invention, the glycosyl group derived from a monosaccharide, oligosaccharide or polysaccharide represented by G is
For example, glycosyl group, mannosyl group, galactosyl group,
Ribosyl group, arabinosyl group, xylosyl group, monosaccharide groups such as fructosyl group, maltosyl group, cellobiosyl group,
Oligosaccharide groups such as lactosyl group and maltotriosyl group,
Examples of the polysaccharide group include cellulose and starch, and preferable groups include a monosaccharide group and an oligosaccharide group. Also,
The average value of m and n represents the same or different 0 or a positive number, and 1 ≦ m + n ≦ 1000, preferably 1 ≦ m + n
≦ 500, more preferably 1 ≦ m + n ≦ 150.

The method for producing the compound of the general formula 3 is not particularly limited, but it is produced by a well-known hydrosilylation reaction of an organohydrogenpolysiloxane and a sugar derivative having a double bond at the terminal. You can
That is, the general formula 5

[Chemical 5] [In Chemical Formula 5, R and ^Ra represent the same or different hydrocarbon groups having 1 to 8 carbon atoms. R ¹ a to R ^6a is different each the same or at least one is a hydrogen atom, the number of remaining carbon 1
~ 8 hydrocarbon groups are shown. The average value of m and n shows the same or different 0 or a positive number, and 1 ≦ m + n ≦ 100.
An organohydrogenpolysiloxane represented by the formula

Embedded image R ⁸ —O—G [In the formula, R ⁸ has 2 to 2 carbon atoms having a double bond in the molecule.
0 represents an organic group, and G represents a glycosyl group derived from a monosaccharide, oligosaccharide or polysaccharide. ] It can manufacture by making it react with the sugar derivative represented by these in the presence of a platinum-type catalyst.

When unreacted hydrogen atoms bonded to Si remain after the completion of the reaction, it is preferable to add an olefin compound after the completion of the reaction so that the unreacted hydrogen atoms are reacted as much as possible. Particularly, in the sugar residue-containing organopolysiloxane derivative represented by the following chemical formula 7, the sugar residue represented by G ^b is a glucosyl group, the hydrocarbon group represented by R ¹¹ is a methyl group, and R ¹² is-( CH ₂ ) ₃ -group,
Further, those having m of 5 to 50 and n of 1 to 50 have general versatility and are suitable for obtaining the hair treatment composition according to the present invention.

[0012]

[Chemical 7] The amount of the sugar residue-containing organopolysiloxane blended in the hair treatment composition according to the present invention is not particularly limited, but is preferably 2% by weight or more, more preferably 5% by weight or more. If it is less than 2% by weight, the effect of reducing skin irritation may not be sufficiently exhibited. The upper limit of the compounding amount is also not particularly limited, but when the amount is extremely large, the ratio of other components constituting the hair treatment composition inevitably becomes low, so that it is preferably up to about 40% by weight. on the other hand,
The quaternary ammonium salt used in the present invention is represented by the following general formula 8.

[0013]

[Chemical 8] (In the above chemical formula 8, R ₁ , R ₂ , R ₃ and R ₄ are an alkyl group, a hydroxyalkyl group, a polyoxyethylene group, or a benzyl group, and one or two of them are C 1
2 to 18 long-chain alkyl groups, and the rest are either alkyl groups having 1 to 3 carbon atoms, hydroxyalkyl groups, polyoxyethylene groups or benzyl groups. X represents a halogen atom or an alkylsulfate group having 1 or 2 carbon atoms in the alkyl group. )

Examples of the quaternary ammonium salt used in the present invention include alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, dialkylmethylbis (2-hydroxyethyl) ammonium chloride, dialkylmethyl (2-hydroxyethyl) ammonium chloride, Alkyldimethyl (2
-Hydroxyethyl) ammonium chloride, alkylpentaethoxylated ammonium chloride, dialkylpolyethoxylated ammonium chloride and the like. Among these, alkyl trimethyl ammonium chloride such as palmityl trimethyl ammonium chloride, tallow alkyl trimethyl ammonium chloride, and stearyl trimethyl ammonium chloride are particularly preferable. The quaternary ammonium salt of the present invention may be used alone or in combination of two or more.

The blending amount of the quaternary ammonium salt of the present invention is 0.2 to 10% by weight based on the total amount of the hair treatment composition.
If it is less than 0.2% by weight, the effect of repairing damage to hair may not be sufficiently exerted, and if it exceeds 10% by weight, tackiness may occur on the hair, which is not preferable. Further, the hair treatment composition of the present invention, in addition to the above essential components, a hydrophobic silicone,
Addition of an oily substance such as a branched higher alcohol, a liquid hydrocarbon and a liquid ester oil will further improve the effect. Examples of the hydrophobic silicone include methylpolysiloxane, methylphenylpolysiloxane, highly polymerized dimethylpolysiloxane, amino-modified silicone, fluorine-modified silicone, fatty acid-modified polysiloxane, and aliphatic alcohol-modified polysiloxane.

Examples of branched higher alcohols include 2-octyldodecanol, 2-decyltetradecanol, 2-octyldecanol, 2-hexyldecanol, and 2-heptylundecanol. Examples of liquid hydrocarbons include liquid paraffin and squalane. As liquid ester oil, isopropyl myristate,
Cetyl-2-ethylhexanoate, stearyl-2-
Ethyl hexanoate, malic acid diisostearyl alcohol ester, neocaptyl glycol dicaprate, ethylene glycol di-2-ethylhexanoate, 1
Examples include cholesteryl 2-hydroxystearate, neopentyl glycol dicaprate, and the like.

If desired, the hair treatment composition of the present invention may further contain humectants, fragrances, preservatives, etc. under qualitative and quantitative conditions that do not impair the object of the present invention. Further, the hair treatment composition according to the present invention can be used in various applications such as a hair rinse agent, a pre-hair rinse agent, a spray type or a dispenser type hair conditioner hair lotion, and the like.

[0018]

The present invention will be described in more detail based on the following examples. The present invention is not limited to the examples. Further, the compounding amount is shown by weight% unless otherwise specified. First, prior to the description of the examples, the evaluation methods are shown below. Transparency It was judged visually with the following criteria. ○… Transparent △… Slightly hazy ×… Opaque or precipitated

Smooth, glossy shampooed hair bundles (5 g, 20 cm) were treated with a sample of 0.
Directly apply 5g and stretch evenly by hand, then at 25 ℃, 65
The state of the hair bundle after being dried in an atmosphere of% RH and allowed to stand overnight was evaluated by 20 panelists. The evaluation standard is
It was evaluated by the following five grades in comparison with a sample consisting of 1.0% by weight of stearyltrimethylammonium chloride, 3% by weight of cetyl alcohol, 10% by weight of propylene glycol and water (the balance). ⊚ ... very good. ○… Slightly excellent. Δ: Equivalent ×: Slightly inferior xx ... inferior.

Skin Irritation Test It is known that skin irritation can be evaluated by the strength of protein denaturation (protein denaturation rate) of a surfactant or a surfactant composition (Japanese Patent Publication No. Sho 59-42038). The irritancy of the composition according to the invention was evaluated by the protein denaturation rate based on this evaluation method. (Protein denaturation rate) Using aqueous high performance liquid chromatography, ovalbumin pH7 buffer solvent, sample concentration 1%
The denaturation rate of ovalbumin in the case of adding a sample so as to be measured was measured using an absorption peak at 220 nm. Denaturation rate = (H ₀ −H _s ) / H ₀ × 100 where H ₀ = height of 220 nm absorption peak of ovalbumin H _s = 2 when sample is added to ovalbumin buffer solvent
Height of 20 nm absorption peak (Evaluation) The height was evaluated according to the following four grades. ⊚: Very low skin irritation-Ovalbumin denaturation rate of less than 30% ◯: Less skin irritation-Ovalbumin denaturation rate of 30%
Or more and less than 60% △ ... Moderate skin irritation-Ovalbumin denaturation rate 60%
Greater than or equal to less than 80% x ... Strongly irritating to skin-Ovalbumin denaturation rate of 80% or higher

Examples 1 to 9 and Comparative Examples 1 and 2 Hair treatment compositions shown in Tables 1 and 2 below were prepared, and their transparency, usability and irritation were examined. As the quaternary ammonium salt, water-soluble stearyltrimethylammonium chloride, palmityldimethylammonium chloride, and slightly soluble but water-soluble dipalmityldimethylammonium chloride, 60
Behenyltrimethylammonium chloride, which dissolves when heated to about 0 ° C, is used, and there is a possibility that poor emulsification for water-based hair treatment that does not contain oily components will occur. A composition was prepared.

[0022]

[Table 1] ──────────────────────────────────── Comparative Examples Examples 1 2 1 2 3 4 5 ──────────────────────────────────── Sugar residue-containing organopolysiloxane compound 9 (G is glycosyl) ) 6.0 6.0 4.5 7.5 10 (G is glycosyl) 6.0 11 (G is mannosyl) 6.0 12 (G is glycosyl) 13 (G is glycosyl) 14 (G is glycosyl) ──────── ──────────────────────────── Quaternary ammonium salt stearyl trimethylammonium chloride 1.2 1.2 1.2 1.2 palmityl trimethylammonium chloride 1.2 dipalmityl Dimethyl ammonium chloride "Behenyl trimethyl ammonium chloride" ───────────────────────────────── Ethanol 10.0 Water balance ─────────── ────────────────────────── Transparency × ○ ○ ○ ○ ○ ○ Skin irritation × ◎ ○ ○ ○ ○ ○ Smoothness ◎ × ◎ ◎ ◎ ◎ ◎ ◎ gloss ○ × ○ ○ ○ ○ ○ ─────────────────────────────────────

[0023]

[Table 2] ────────────────────────── Example 6 7 8 9 ────────────── ──────────── Organopolysiloxane containing sugar residue 9 (G is glycosyl) 2.73 10 (G is glycosyl) 11 (G is mannosyl) 12 (G is glycosyl) 8.0 13 (G is glycosyl) 8.0 14 (G is glycosyl) 8.0 ────────────────────────── Quaternary ammonium salt Stearyl trimethyl ammonium chloride 2.0 2.0 Palmytyltrimethylammonium Chloride 0.27 Dipalmityldimethylammonium Chloride Behenyltrimethylammonium Chloride 2.0 ────────────────────────────────── Ethanol 10.0 Water The rest ─── ─────────────────────── Transparency ○ ○ ○ ○ Skin irritation ○ ○ ○ ○ Smoothness ◎ ◎ ◎ ◎ ◎ Shine ○ ○ ○ ○ ─── ───────────────────────

In the above table, chemical formulas 9 to 14 are as follows.

[Chemical 9]

[Chemical 10]

[Chemical 11]

[Chemical 12]

[Chemical 13]

[Chemical 14] As is clear from Tables 1 and 2, when only the quaternary ammonium salt was blended (Comparative Example 1), skin irritation was considerably high. Further, when only the sugar residue-containing organopolysiloxane was blended (Comparative Example 2), the skin irritation caused by the quaternary ammonium salt was extremely low, but of course it was obtained when the quaternary ammonium salt was blended. The resulting hair damage repair effect cannot be obtained.

On the other hand, as is clear from Examples 1 to 9, when the sugar residue-containing organopolysiloxane was made to coexist with the quaternary ammonium salt, the hair damage repairing effect based on the quaternary ammonium salt was obtained. Is fully demonstrated,
Further, it is understood that the skin irritation is also reduced to about 1/3 in the score. Further, in Comparative Examples 1 and 2, the transparency was low and there was a problem in the appearance, but when both were coexistent, the transparency was improved, and the saccharide residue-containing organopolysiloxane produced a quaternary ammonium salt. It can be seen that the solubility is improved.

Examples 10 to 16 Next, similar to Examples 1 to 9, hair-treating compositions were prepared using poorly water-soluble quaternary ammonium salts and containing an oily component, and their properties were examined. . The results are shown in Table 3 below.

[Table 3] ──────────────────────────────────── Example 10 11 12 13 13 14 15 16 ─ ─────────────────────────────────── Sugar residue-containing organopolysiloxane compound 9 (G is glycosyl) 2.4 1.2 Chemical 10 (G is glycosyl) 2.4 1.2 Chemical 11 (G is mannosyl) 2.4 Chemical 12 (G is glycosyl) 2.4 Chemical 13 (G is glycosyl) 2.4 Chemical 14 (G is glycosyl) 2.4 ───────── ──────────────────────────── Quaternary ammonium salt stearyltrimethylammonium chloride 0.6 0.6 Palmytyltrimethylammonium chloride 0.6 0.6 0.6 Dipalmityl Dimethyl ammonium chloride 0.6 0.6 ─────────────── ──────────────────── Methylpolysiloxane 0.4 0.2 2-Octyl edecanol 0.4 0.2 Squalane 0.4 Isopropyl myristate 0.4 0.4 Methylphenylpolysiloxane 0.4 ────── ────────────────────────────── Ethanol 10.0 Water balance ────────────── ─────────────────────── Transparency ○ ○ ○ ○ ○ ○ ○ Skin irritation ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ Smoothness ◎ ◎ ◎ ◎ ◎ ◎ ◎ Tsuya ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ──────────────────────────────────── Clear from Table 3 above As described above, when the oily component is contained, the sugar residue-containing organopolysiloxane and the quaternary ammonium salt are added in the cases shown in Tables 1 and 2 above. Compared to the sufficient smoothness and gloss is obtained as a half, yet it is possible to reduce the skin irritation.

The specific formulation examples are shown below. In addition,
All the hair treatment compositions were excellent in transparency, smoothness and gloss, and almost no skin irritation was observed. Example 17 Hair Treatment Lotion Sugar-containing organopolysiloxane (G is a glycosyl group in Chemical formula 9) 2.0 Dipalmityldimethylammonium chloride 0.4 Ethanol 40.0 Propylene glycol 6.0 Dimethylpolysiloxane (6 cps) 0 .2 Dye Appropriate amount Perfume Appropriate amount Purified water Remainder <Process> Dissolve the sugar residue-containing organopolysiloxane and dipalmityldimethylammonium chloride in ethanol, and add and dissolve dimethylpolysiloxane and the perfume (phase A). ). On the other hand, propylene glycol and dye are dissolved in purified water (phase B). Phase B is added to Phase A with stirring to obtain a hair treatment lotion.

Example 18 Hair Treatment Lotion Sugar residue-containing organopolysiloxane (wherein G is a glycosyl group) 1.2 Stearyltrimethylammonium chloride 0.2 Ethanol 30.0 Dipropylene glycol 2.0 Cationic Polypeptide 0 .6 Squalane 0.1 Isopropyl myristate 0.1 Dye Appropriate amount Perfume Appropriate amount Purified water Remainder <Production Method> Organopolysiloxane sugar residue and stearyl trimethyl ammonium chloride are dissolved in ethanol, and then squalane and isopropyl myristate are added. , Add perfume and dissolve (Phase A). On the other hand, dipropylene glycol, a cationic polypeptide and a dye are dissolved in purified water (phase B). Phase B is added to Phase A with stirring,
Got a hair treatment lotion.

[0029]

As described above, in the hair treatment composition according to the present invention, since the sugar residue-containing organopolysiloxane is allowed to coexist with the quaternary ammonium salt, the hair damage repairing property is excellent. The skin irritation can be extremely low.

Claims (1)

[Claims] 1. The following general formula 1 [In the above chemical formula 1, R and R ^a each have the same or different carbon number 1
~ 8 hydrocarbon groups are shown. R ^{1 to} R ⁶ are the same or different, and at least one is represented by the general formula 2 —R ⁷ —O—G (wherein, R ⁷ represents an organic group having 2 to 20 carbon atoms, and G is Represents a sugar residue derived from a monosaccharide, an oligosaccharide or a polysaccharide), and the rest has 1 to 8 carbon atoms.
Represents a hydrocarbon group or a hydroxy group. The average value of m and n shows the same or different 0 or a positive number, and 1 ≦ m +
n ≦ 1000. ] One or two or more kinds of the organopolysiloxane derivative having a sugar residue represented by the following, and one or more kinds of the quaternary ammonium salt are blended, and a hair treatment composition.