JPH06128126A - Cosmetic composition - Google Patents

Abstract

PURPOSE:To provide a cosmetic composition having high affinity to skin and hair, giving low stimulation and having remarkably improved functions and usability compared with conventional cosmetics. CONSTITUTION:The cosmetic composition contains a cationic surfactant consisting of a reaction product of (A) an estolide, (B) a diamine having a primary or secondary amino group and a tertiary nitrogen atom and (C) a quaternarizing agent. A representative example of the estolide is an intermolecular condensation product of castor oil fatty acid or hydrogenated castor oil fatty acid.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a cosmetic composition containing a lipophilic cationic surfactant.

[0002]

2. Description of the Related Art Cationic surfactants have a good affinity for skin and hair and are therefore used as a main component of rinses in the field of cosmetics. However, recent cosmetics have been required to have various functions, and cationic surfactants used therein are also required to have complicated performance.

In particular, as the frequency of use of shampoo has increased and it has become widespread, low irritation has become more important than detergency. In addition, a rinse-integrated shampoo is required to have good compatibility with an anionic surfactant.

The properties required of cationic surfactants are as follows:
It can be summarized as follows. (a) Irritant Non-irritating or non-irritating. (b) Mixability (Compatibility) In order to give the shampoo a rinsing function, it is necessary to mix a cationic surfactant in the anionic surfactant composition. Good compatibility) is required. In addition, it is required that the compoundability (compatibility) with an oily substance such as ester, hydrocarbon and silicone is good. (c) Oiliness imparting It is required to be a cationic surfactant having lipophilicity for the treatment effect and other purposes. (d) Water Solubility Due to its use in shampoos and the like, it is required to have water solubility in spite of having the above properties.

In order to improve the cationic surfactant, various measures have been taken to introduce more long-chain alkyl groups than general cationic surfactants. One example thereof is distearyldimethylammonium chloride, and this compound has two C18 alkyl groups with respect to the quaternary nitrogen and has lipophilicity.

US Pat. No. 4,220,581 describes
Cationic surfactants such as γ-ricinolamidopropyldimethylbenzylammonium chloride and γ-12-hydroxystearamidopropyldimethylbenzylammonium chloride derived from castor oil fatty acid (ricinoleic acid) have been shown to be hypoallergenic. And it is said that it has excellent water solubility.

EP 0283994 A2 shows a new cationic surfactant which remains the triglyceride structure of castor oil.

In Japanese Patent Publication No. 57-25251 and its first application, GB 1373660, a hydroxycarboxylic acid intermolecular condensate such as poly (hydroxystearic acid) is added to 3-dimethylaminopropylamine or 3-dimethylaminopropylamine. It is described to react with octadecylaminopropylamine followed by a quaternizing agent such as dimethyl sulfate.

[0009]

Cationic surfactants having a large number of long-chain alkyl groups introduced therein, such as distearyldimethylammonium chloride, have a remarkably low water-solubility, and thus are generally in the form of a paste as a 75% product of hydrous alcohol. It is handled as a form, and there are restrictions on the form of use. Moreover, it is irritating.

Cationic surfactants such as ricinolamidopropyl dimethylbenzyl ammonium chloride disclosed in US Pat. No. 4,220,581 are
From the viewpoint of hydrophilic-lipophilic balance, it is hydrophilic but hardly lipophilic, and its compatibility with oily substances and anionic surfactants is insufficient.

The cationic surfactants disclosed in EP 0283994 A2 have problems that they are not sufficiently water-soluble and that they are not sufficiently compoundable with oily substances having small polarity such as hydrocarbons.

JP-B-57-25251 and GB
In 1373660, a cationic surfactant having an intermolecular condensate of oxyacid as a hydrophobic group is shown. Its use is as a pigment dispersant for printing inks and paints. There is no description.

Under such a background, the present invention aims to provide a cosmetic composition which has good affinity for skin and hair, is less irritating, and has extremely excellent function and usability as compared with conventional products. It is what

[0014]

The cosmetic composition of the present invention comprises an estolide (A), a diamine (B) having a primary or secondary amino group and a tertiary nitrogen, and a quaternizing agent.
It contains a cationic surfactant composed of the reaction product of (C).

The present invention will be described in detail below. The estolide is a dimer or higher intermolecular condensate of oxyfatty acids with each other or oxyfatty acids and other fatty acids, that is, oligofatty acid.

A cationic surfactant comprising a reaction product of estolide (A), a diamine (B) having either a primary or secondary amino group and a tertiary nitrogen, and a quaternizing agent (C) is
It is preferably produced by the following three steps of reaction.

The first-step reaction is a reaction for obtaining estolide (A), which is a hydroxy fatty acid (or a lower alkyl ester thereof as the case may be) alone or a fatty acid which does not substantially have an OH group (or a lower fatty acid thereof). Lower alkyl ester) is subjected to a condensation reaction with heating to form estolide. Although this estridation reaction can be carried out simultaneously with the amidation reaction described below,
It is advantageous to generate estolide (A) before the amidation reaction.

The degree of condensation of the estolide (A) is appropriately from dimer to heptamer, and in some cases it is preferable to use a multimer. It should be noted that a mixture of 1-mer is acceptable, but in this case as well, when the whole is averaged, 1.3-mer or more, particularly 1.5-mer or more, further 1.8-mer or more, particularly preferably 2.0-mer or more. Please note that When the proportion of estolide of dimer or more is too small, the desired effect as a cosmetic cannot be exhibited, such as a problem of irritation and lack of compatibility with oily substances.

Examples of the hydroxy fatty acid include castor oil fatty acid (main component is ricinoleic acid) and hydrogenated castor oil fatty acid (main component is 12-hydroxystearic acid). As the fatty acid having substantially no OH group, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, montanic acid, oleic acid,
Examples thereof include linoleic acid, linolenic acid, coconut oil fatty acid, palm oil fatty acid, olive oil fatty acid, tallow fatty acid, hydrogenated tallow fatty acid and the like.

The second step reaction is the reaction of the obtained estolide.
(A) is a reaction to obtain an amide-tertiary amine intermediate by reacting a diamine (B) having either a primary or secondary amino group and a tertiary nitrogen, the amidation reaction is usually It is performed by heating to a temperature of about 140 to 230 ° C. in an inert gas atmosphere.

The diamine (B) having either a primary or secondary amino group and a tertiary nitrogen in the molecule is N,
N-dimethylaminopropylamine, N, N-diethylaminopropylamine, N, N-diethylaminoethylamine, N, N-dimethylaminoethylamine, N, N
-Diethylaminobutylamine, N, N-dimethylaminoethoxypropylamine, N-aminoethylmorpholine, N-aminopropylmorpholine, N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethyl-4-pipecoline, N-amino Propyl-4-
Examples thereof include pipecoline, N-methylpiperazine, N-hydroxyethoxypiperazine, and 2-methylaminoethylpyridine, but are not limited thereto as long as they have a primary or secondary amino group and a tertiary nitrogen. . Polyamines other than triamines are not suitable for the purpose of the present invention because they cause side reactions, but they can be used in combination with the above diamines to some extent.

The reaction in the third step is a reaction in which the obtained amide-tertiary amine intermediate is reacted with the quaternizing agent (C) to obtain a cationic surfactant.

Examples of the quaternizing agent (C) include dimethyl sulfate, diethyl sulfate, benzyl chloride, methyl bromide, lauryl bromide and lauryl chloride.

The quaternization reaction is usually carried out by heating to a temperature of about 60 to 100 ° C. in the presence of a polar solvent.

By the above three-step reaction, the desired reaction product, that is, the desired cationic surfactant is obtained. In this cationic surfactant, estolide (A) is a castor oil fatty acid dimer, amine (B) is N, N-dimethylaminopropylamine, and quaternizing agent (C) is benzyl chloride. Then, it is represented by the following chemical formula 1.

[0026]

[Chemical 1]

Since this cationic surfactant has good compatibility with anionic surfactants and amphoteric surfactants used in cosmetics, it should be used in combination with such anionic surfactants and amphoteric surfactants. It is desirable to do this.
Examples of the anionic surfactant include alkyl sulfate, alkyl sulfate tetraethanolamine salt, amide ether sulfate, coconut oil fatty acid methyl taurine salt, N-
Examples include cocoyl-L-glutamic acid monotetraethanolamine salt, polyoxyethylene alkyl ether sulfate, alkyl sulfocarboxylate, α-olefin sulfonate, alkyl phosphate, polyoxyethylene alkyl ether phosphate and the like. . Examples of the amphoteric surfactant include betaine type (coconut oil fatty acid amide propyl betaine etc.) and various amphoteric surfactants for cosmetics such as imidazoline derivatives.

Among the cosmetics, hair cosmetics, especially shampoo having a rinsing function (rinse-integrated shampoo), are important, and hair rinses, hair treatments, hair nicks and the like may be used.

[0029]

The present invention provides that the above-mentioned cationic surfactants have a low stimulative property, good compatibility with anionic surfactants and amphoteric surfactants, good compatibility with oily substances, and water-soluble properties. It was achieved as a result of discovering that it has excellent properties and applying it to cosmetics.

The cosmetic composition of the present invention has a good affinity for skin and hair, is low in irritation, and is extremely preferable in function and usability as compared with conventional products.

[0031]

EXAMPLES The present invention will be further described with reference to examples. Hereinafter, "%" means% by weight.

<Synthesis of Cationic Surfactant> Synthesis Example 1 621.6 g (2.1 mol) of castor oil fatty acid was charged into a reaction vessel and the neutralization value was 90 while removing water out of the system at 170 to 200 ° C. under nitrogen stream. It was made to react until it became. This allows
Estoride (oligo fatty acid) corresponding to a castor oil fatty acid dimer was obtained.

The reaction was cooled to 80 ° C. and then 104.2 g (1.02 N, N-dimethylaminopropylamine).
Mol) was added and reacted for 9 hours while removing water outside the system at 150 to 160 ° C. under a nitrogen stream. After that, 120 ~
Dehydration and removal and removal of excess amine were performed at 140 ° C. under reduced pressure. The total amine value of this product was 85.0.

99.0 g (0.15 mol) of this reaction product was placed in a reaction vessel, and 43.0 g of isopropyl alcohol was placed therein.
Diethyl sulfate while controlling at 80 ℃
23.1 g (0.15 mol) was added dropwise over 0.5 hours, and then 80
The reaction was carried out at 0 ° C for 6 hours. Then, from this reaction product at 80 ° C
The isopropyl alcohol was distilled off under reduced pressure with to obtain the desired product.

Synthesis Example 2 651.2 g (2.2 mol) of castor oil fatty acid was reacted in the same manner as in Synthesis Example 1 until the neutralization number reached 62. As a result, estolide (oligo fatty acid) corresponding to the castor oil fatty acid trimer was obtained.

The reaction product was cooled to 80 ° C., and then 77.0 g (0.75 mol) of N, N-dimethylaminopropylamine was added and the reaction was carried out under the same conditions as in Synthesis Example 1. The total amine value of this product was 56.3.

707.0 g (0.71 mol) of this reaction product was placed in a reaction vessel, 300 g of isopropyl alcohol was placed therein, and lauryl bromide was controlled while controlling at 80 ° C.
177.0 g (0.71 mol) was added dropwise over 0.5 hour to react in the same manner as in Synthesis Example 1, and then isopropyl alcohol was distilled off under reduced pressure at 80 ° C. to obtain the desired product.

Synthesis Example 3 388.5 g (1.26 mol) of hydrogenated castor oil fatty acid having a neutralization value of 6
The reaction was carried out in the same manner as in Synthesis Example 1 until it reached 0. As a result, estolide (oligo fatty acid) corresponding to hydrogenated castor oil fatty acid trimer was obtained.

The reaction product was cooled to 80 ° C., 42.9 g (0.42 mol) of N, N-dimethylaminopropylamine was added, and the reaction was carried out under the same conditions as in Synthesis Example 1. The total amine value of this product was 78.0.

215.8 g (0.3 mol) of this reaction product was placed in a reaction vessel, and 92.5 g of isopropyl alcohol was placed therein,
Benzyl chloride 38.0 while controlling at 80 ℃
g (0.3 mol) was added dropwise over 0.5 hour to react in the same manner as in Synthesis Example 1, and then isopropyl alcohol was distilled off under reduced pressure at 80 ° C. to obtain the desired product.

Synthetic Example 4 651.2 g (2.2 mol) of castor oil fatty acid was reacted in the same manner as in Synthetic Example 1 until the neutralization value became 41.5. As a result, estolide (oligo fatty acid) corresponding to castor oil fatty acid pentamer was obtained.

The reaction product was cooled to 80 ° C., and then 52.0 g (0.51 mol) of N, N-dimethylaminopropylamine was added and reacted under the same conditions as in Synthesis Example 1. The total amine value of this product was 40.2.

685.0 g (0.49 mol) of this reaction product was placed in a reaction vessel, 300 g of isopropyl alcohol was placed therein, and benzyl chloride was added while controlling at 80 ° C.
62.0 g (0.49 mol) was added dropwise over 0.5 hour to Synthesis Example 1
The reaction was carried out in the same manner as above, and then isopropyl alcohol was distilled off at 80 ° C. under reduced pressure to obtain the desired product.

Synthetic Example 5 651.2 g (2.2 mol) of castor oil fatty acid was reacted in the same manner as in Synthetic Example 1 until the neutralization value became 41.5. As a result, estolide (oligo fatty acid) corresponding to castor oil fatty acid pentamer was obtained.

The reaction product was cooled to 80 ° C., and then 52.0 g (0.51 mol) of N, N-dimethylaminopropylamine was added and reacted under the same conditions as in Synthesis Example 1. The total amine value of this product was 40.5.

676.0 g (0.49 mol) of this reaction product was placed in a reaction vessel, 290 g of isopropyl alcohol was placed therein, and 75.0 g (0.49 mol) of diethyl sulfate was added dropwise over 0.5 hours while controlling at 80 ° C. The reaction was performed in the same manner as in 1, and then isopropyl alcohol was distilled off under reduced pressure at 80 ° C. to obtain the desired product.

Synthesis Example 6 670.1 g (2.17 mol) of hydrogenated castor oil fatty acid had a neutralization value of 3
The reaction was carried out in the same manner as in Synthesis Example 1 until it reached 7. As a result, estolide (oligo fatty acid) corresponding to the hydrogenated castor oil fatty acid pentamer was obtained.

The reaction product was cooled to 80 ° C., and then 45.0 g (0.44 mol) of N, N-dimethylaminopropylamine was added and reacted under the same conditions as in Synthesis Example 1. The total amine value of this product was 35.4.

221.9 g (0.14 mol) of this reaction product was placed in a reaction vessel, 95 g of isopropyl alcohol was placed therein, and benzyl chloride was added while controlling at 80 ° C.
17.7 g (0.14 mol) was added dropwise over 0.5 hour to Synthesis Example 1
The reaction was carried out in the same manner as above, and then isopropyl alcohol was distilled off at 80 ° C. under reduced pressure to obtain the desired product.

Synthesis Example 7 195.4 g (0.66 mol) of castor oil fatty acid and 93.2 of oleic acid
g (0.33 mol) was reacted in the same manner as in Synthesis Example 1 until the neutralization value reached 78. As a result, OH of castor oil fatty acid
An estolide (oligo fatty acid) mainly containing a dimer having a COOH group of oleic acid condensed to the group was obtained.

The reaction product was cooled to 80 ° C., and then 42.9 g (0.42 mol) of N, N-dimethylaminopropylamine was added and reacted under the same conditions as in Synthesis Example 1. The total amine value of this product was 69.9.

240.8 g (0.3 mol) of this reaction product was placed in a reaction vessel, 103 g of isopropyl alcohol was placed therein, and benzyl chloride was added while controlling at 80 ° C.
38.0 g (0.3 mol) was added dropwise over 0.5 hour to react in the same manner as in Synthesis Example 1, and then isopropyl alcohol was distilled off under reduced pressure at 80 ° C. to obtain the desired product.

Synthetic Example 8 621.6 g (2.1 mol) of castor oil fatty acid was reacted in the same manner as in Synthetic Example 1 until the neutralization number reached 90. As a result, estolide (oligo fatty acid) corresponding to the castor oil fatty acid dimer was obtained.

The reaction was cooled to 80 ° C. and then 131.6 g (1.01 N, N-diethylaminopropylamine).
Mol) was added and the reaction was carried out under the same conditions as in Synthesis Example 1. The total amine value of this product was 81.0.

623.4 g (0.90 mol) of this reaction product was placed in a reaction vessel, 270 g of isopropyl alcohol was placed therein, and benzyl chloride was added while controlling at 80 ° C.
113.9 g (0.90 mol) was added dropwise over 0.5 hour to react in the same manner as in Synthesis Example 1, and then isopropyl alcohol was distilled off at 80 ° C. under reduced pressure to obtain the desired product.

Synthesis Example 9 621.6 g (2.1 mol) of castor oil fatty acid was reacted in the same manner as in Synthesis Example 1 until the neutralization number reached 90. As a result, estolide (oligo fatty acid) corresponding to the castor oil fatty acid dimer was obtained.

The reaction product was cooled to 80 ° C., 145.4 g (1.01 mol) of N-aminopropylmorpholine was added, and the reaction was carried out under the same conditions as in Synthesis Example 1. The total amine value of this product was 73.5.

687.0 g (0.90 mol) of this reaction product was placed in a reaction vessel, 270 g of isopropyl alcohol was placed therein, and 138.8 g (0.90 mol) of diethyl sulfate was added dropwise over 0.5 hours while controlling at 80 ° C. to prepare a synthesis example. The reaction was performed in the same manner as in 1, and then isopropyl alcohol was distilled off under reduced pressure at 80 ° C. to obtain the desired product.

<Summary of Synthetic Conditions> The types of the respective components of estolide (A), diamine (B) and quaternizing agent (C) in the cationic surfactants synthesized in Synthesis Examples 1 to 9 are summarized as follows. become.

Synthetic Example 1 (A) Castor oil fatty acid dimer (B) N, N-dimethylaminopropylamine (C) diethyl sulfate Synthetic Example 2 (A) Castor oil fatty acid trimer (B) N, N- Dimethylaminopropylamine (C) Lauryl bromide Synthesis example 3 (A) Hydrogenated castor oil fatty acid trimer (B) N, N-Dimethylaminopropylamine (C) Benzyl chloride Synthesis example 4 (A) Castor oil fatty acid 5 amount Form (B) N, N-Dimethylaminopropylamine (C) Benzyl chloride Synthesis Example 5 (A) Castor oil fatty acid pentamer (B) N, N-Dimethylaminopropylamine (C) Diethylsulfate Synthesis Example 6 (A ) Hydrogenated castor oil fatty acid pentamer (B) N, N-dimethylaminopropylamine (C) benzyl chloride Synthesis Example 7 (A) Castor oil fatty acid-oleic acid dimer (B) N, N-dimethylaminopropyl Amine (C) Synthesis example 8 (A) Castor oil fatty acid dimer (B) N, N-diethylaminopropylamine (C) Benzyl chloride Synthesis example 9 (A) Castor oil fatty acid dimer (B) N-aminopropylmorpholine (C) Diethyl sulfate

<Production of shampoo having rinse function /
Part 1> Polyoxyethylene lauryl ether sodium sulfate was selected as the most commonly used anionic surfactant, and a shampoo having the following formulation was prepared. The appearance, foaming property and low temperature stability of the obtained shampoo were evaluated, and sensory evaluation was also performed on combability, flexibility and moist feeling.

Formulation (1) Purified water 50.1% (2) 27% aqueous solution of sodium polyoxyethylene lauryl ether sulfate 45.0% (3) Methyl paraoxybenzoate 0.2% (4) Coconut oil diethanolamide 2.0% (5) Cationic interface Activator 1.0% (6) Perfume 0.2% (7) Sodium chloride 1.5% Total 100.0% (Note) The compounding% of the cationic surfactant was 100% in terms of purity and 1.0% was included.

Preparation method The above (1) to (4) are heated to 50 to 55 ° C. and dissolved to homogenize. Next, add (5) at the same temperature to this product and dissolve it uniformly. After that, (6) and (7) are added, and the mixture is stirred until it becomes uniform to obtain a shampoo.

Measurement or Evaluation Method The viscosity was measured under the conditions of No. 3-12 rpm and 30 seconds. Low temperature stability is evaluated at 4 ° C. (○: transparent, ×: cloudy or precipitate) Effervescence is 0.1% of each shampoo prepared by the above formulation.
10 ml of the aqueous solution was placed in a 50 ml Nessler tube, shaken vigorously 20 times for 10 seconds, and the height of bubbles immediately after standing was measured. With respect to combing, flexibility, and moist feeling, sensory evaluation was performed according to the following criteria. ◎: Good, ○: Fair, □: Normal, △: Fair,
×: Bad

Results As cationic surfactants, Synthesis Example 1 (Example 1), Synthesis Example 2 (Example 2), Synthesis Example 3 (Example 3), and
Those obtained in Synthesis Example 4 (Example 4), Synthesis Example 6 (Example 5), Synthesis Example 7 (Example 6), Synthesis Example 8 (Example 7), and Synthesis Example 9 (Example 8) were used. Table 1 shows the results of the tests.

As the cationic surfactant, cetyltrimethylammonium chloride 50% product (Comparative Example 1) and stearyltrimethylammonium chloride 6 were used.
3% product (Comparative Example 2), behenyltrimethylammonium chloride 82% product (Comparative Example 3), stearylbenzyldimethylammonium chloride 86% product (Comparative Example 4), ricinolamidopropyltrimethylammonium chloride 56% product (Comparative Example 5) Table 2 when using
Shown in. Table 2 also shows blanks containing no cationic surfactant.

[0067]

[Table 1] Example 1 2 3 4 5 6 7 8 Evaluation of physical properties Appearance Transparent Transparent Transparent Transparent Transparent Transparent Transparent Transparent Transparent Viscosity (cps) 520 460 250 60 50 120 450 410 Low temperature stability ○ ○ ○ ○ ○ ○ ○ ○ ○ Foaming property (mm) 25 25 25 25 25 25 25 25 Sensory evaluation Comb through ○ ◎ ◎ ◎ ◎ ◎ ◎ ○ ○ Flexibility ○ ◎ ◎ ◎ ◎ ◎ ◎ ◎ ○ Moisture ◎ ◎ ◎ ○ ◎ ○ ◎ ◎ ◎

[0068]

[Table 2] Comparative example Blank 1 2 3 4 5 Physical property evaluation Appearance Transparent Clear Transparent Clear cloudy Clear cloud Viscosity (cps) 1150 7000 2200--1650 Low temperature stability ○ × ×--○ Foamability (mm) 25 25 25 25 25 25 Sensory evaluation Comb through △----□ Flexibility △ ---- □ Moisture △----□

From the above results, it was necessary to use a betaine-type surfactant in order to prepare a shampoo having a rinsing function with a usual cationic surfactant, but the cationic surfactant obtained in the synthesis example was used. By using, it can be blended in an anionic surfactant-based shampoo that could not normally be blended, and it is also excellent in sensory evaluation such as combability, flexibility and moist feeling. Was confirmed.

<Production of shampoo having rinse function /
Part 2> Amidopropyl betaine was selected as a general betaine-based rinse-integrated shampoo, and a shampoo having the following formulation was prepared. The appearance, foaming property and low temperature stability of the obtained shampoo were evaluated, and sensory evaluation was also performed on combability, flexibility and moist feeling. Preparation method,
The measurement or evaluation method is the same as above.

Formulation (1) Purified water 44.45% (2) 26% aqueous solution of coconut oil fatty acid amide propyl betaine 50.0% (3) Methyl paraoxybenzoate 0.2% (4) Coconut oil diethanolamide 4.0% (5) Cationic surface activity Agent 1.0% (6) Perfume 0.2% (7) Citric acid 0.15% Total 100.0% (Note) The compounding% of the cationic surfactant was 100% in terms of purity and 1.0% was included.

Results As cationic surfactants, Synthesis Example 1 (Example 9), Synthesis Example 3 (Example 10), and Synthesis Example 4 (Example 1), respectively.
1), Synthesis Example 6 (Example 12), Synthesis Example 9 (Example 1)
Table 3 shows the results when the product obtained in 3) was used.

As the cationic surfactant, cetyltrimethylammonium chloride 50% product (Comparative Example 6) and stearyltrimethylammonium chloride 6 were used.
3% product (Comparative Example 7), stearylbenzyldimethylammonium chloride 86% product (Comparative Example 8), ricinolamidopropyltrimethylammonium chloride 56
Table 4 shows the case where the% product (Comparative Example 9) was used. Table 4 also shows blanks containing no cationic surfactant.

[0074]

[Table 3] Example 9 10 11 12 13 Evaluation of physical properties Appearance Transparent Transparent Transparent Transparent Transparent Transparent Viscosity (cps) 480 420 380 360 420 Low temperature stability ○ ○ ○ ○ ○ Foaming (mm) 18 18 18 18 18 Sensory evaluation Combing ○ ◎ ◎ ◎ ○ Flexibility ○ ◎ ◎ ◎ ○ Moisture ◎ ◎ ◎ ○ ◎

[0075]

[Table 4] Comparative example Blank 6 7 8 9 Physical property evaluation Appearance Transparent Transparent Transparent White cloud Transparent Viscosity (cps) 500 580 760-550 Low temperature stability ○ ○ ○-○ Foaming (mm) 18 18 18-18 Sensory evaluation Combing △ □ ○ -□ Flexibility △ ○ □-○ Moisture □ ○ ○-□

From the above results, even when the cationic surfactant obtained in the synthesis example is mixed in the betaine-based shampoo base, compared with the commonly used cetyltrimethylammonium chloride and stearyltrimethylammonium chloride, It was confirmed that the sensory evaluations such as combing, flexibility and moist feeling were further excellent.
It was also confirmed that the sensory evaluations such as combing and moisturizing were good even when compared with ricinoleamidopropyltrimethylammonium chloride.

<Manufacture of Hair Rinse> A hair rinse having the following formulation was prepared, and the obtained rinse was subjected to a sensory evaluation for flexibility, slippery feel and moist feel.

Formulation (1) Purified water 89.8% (2) Propylene glycol 5.0% (3) Methyl paraoxybenzoate 0.2% (4) Cationic surfactant 2.0% (5) Cetanol 3.0% Total 100.0% (Note) Cationic interface The compounding percentage of the activator was calculated to be 100% and 2.0% was included.

Preparation Method (1) to (3) are heated to 75 ° C., the mixture of (4) and (5) at the same temperature is added and emulsified. After emulsification, cool to 40 ° C.

Evaluation method : 5 g of the hair rinse thus obtained was uniformly applied to a hair bundle, left for 5 minutes, washed with running water, towel-dried, and then dried in a dryer for 10 minutes to obtain flexibility, slipperiness, and The moist feeling was sensory evaluated according to the following criteria. ◎: Good, ○: Fair, □: Normal, △: Fair,
×: Bad

Results As cationic surfactants, Synthesis Example 2 (Example 14), Synthesis Example 3 (Example 15), and Synthesis Example 4 (Example 1), respectively.
6), Synthesis Example 6 (Example 17), Synthesis Example 8 (Example 1)
Table 5 shows the results when the product obtained in 8) was used. Further, as the cationic surfactant, stearyl trimethyl ammonium chloride 63% product (Comparative Example 10), cetyl trimethyl ammonium chloride 50% product (Comparative Example 11), and ricinolamidopropyl trimethyl ammonium ammonium chloride 56% product (Comparative Example 12) were used. The results when used are also shown in Table 5.

[0082]

[Table 5] Example ratio Comparative example 14 15 16 17 18 10 11 12 Sensory evaluation Flexibility ○ ◎ ◎ ◎ ◎ ◎ 〜 ○ ○ ○ ○ Sliding ◎ ◎ ◎ ◎ ◎ ◎ ○ □ □ Moisture ◎ ○ ◎ ◎ ○ ○ ○ ~ □ □

From the above results, when the cationic surfactant obtained in the synthesis example is blended, the flexibility, slipperiness and moist feeling are compared with the case where the cationic surfactant which is generally used conventionally is blended. It turns out that sensory evaluation such as is excellent.

<Manufacture of Hair Treatment> A hair treatment having the following formulation was prepared, and the obtained hair treatment was subjected to a sensory evaluation of flexibility, slipperiness, and moistness.

Formulation (1) Purified water 78.3% (2) Glycerin 5.0% (3) Methyl paraoxybenzoate 0.2% (4) Cationic surfactant 2.0% (5) Cetanol 7.5% (6) Squalane 3.0% (7) White petrolatum 1.0% (8) Self-emulsifying glycerin monostearate 3.0% 100.0 % in total (Note) Cationic surfactant content was calculated to be 100% and 2.0% was included.

Preparation method (1) to (3) above were heated to 80 ° C., and (4) to (8) dissolved at the same temperature were added to this and emulsified. After emulsification, 45 ℃
Cool down and get a hair treatment.

Evaluation method The method described in the section of hair rinse was adopted.

Results As cationic surfactants, Synthesis Example 2 (Example 19), Synthesis Example 4 (Example 20), and Synthesis Example 6 (Example 2), respectively.
Table 6 shows the results when the product obtained in 1) was used. As the cationic surfactant, stearyl trimethyl ammonium chloride 63% product (Comparative Example 13), behenyl trimethyl ammonium chloride 82% product (Comparative Example 14), and stearyl benzyl dimethyl ammonium chloride 86% product (Comparative Example 15) were used. The results are also shown in Table 6.

[0089]

[Table 6]  Example Comparative example 19 20 21 13 14 15 Sensory evaluation Flexibility ○ ◎ ◎ ○ ○ ◎ Sliding feeling ◎ ◎ ◎ ○ □ ○ ～ □Moisture ◎ ◎ ◎ □ ○ □

From the above results, when the cationic surfactant obtained in the synthesis example is blended, the flexibility, slipperiness and moist feeling, etc. are compared with the case where the cationic surfactant which is generally used conventionally is blended. It can be seen that the sensory evaluation of is excellent.

<Manufacture of Heartonic> The following formulation was prepared, and sensory evaluation was performed on the flexibility and moist feeling of the obtained hairnic.

Prescription (1) Ethanol 55.0% (2) Photosensitizer No. 301 0.002% (3) L-menthol 0.1% (4) Resorcinol 0.1% (5) Perfume 0.05% (6) Polyoxyethylene (30) Polyoxy Propylene (6) Decyl tetradecyl ether 0.2% (7) Dipropylene glycol 3.0% (8) Purified water 40.848% (9) Assembly extract 0.2% (10) Cationic surfactant 0.5% Total 100.0% (Note) Cationic surfactant The compounding percentage of the agent was 100% in terms of purity, and was 0.5%.

Preparation Method (2) is dissolved in (1) above. Next, the mixture of (3) to (6) is added to make it uniform. Then add (7). (8) is added while stirring the mixture of (1) to (7). Once uniform,
Add (9) and (10) and stir until uniform.

Evaluation method The method described in the section on hair rinse was adopted.

Results As cationic surfactants, Synthesis Example 1 (Example 22), Synthesis Example 3 (Example 23), and Synthesis Example 5 (Example 2), respectively.
Table 7 shows the results when the product obtained in 4) was used. Further, blanks containing no cationic surfactant are also shown in Table 7.

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[Table 7] Practical Example 22 23 24 Blank sensory evaluation Flexibility ○ ○ ○ □ Moisture ○ ○ ◎ □

From the above results, even in hair arts, when the cationic surfactant obtained in the synthesis example is blended, the flexibility and You can see that it gives a moist feeling.

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EFFECTS OF THE INVENTION The cosmetic composition of the present invention, especially the shampoo having a rinsing function, has a good affinity for skin and hair, is low in irritation, and has extremely preferable functions and usability as compared with conventional products.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Yoshiyuki Ito 13-26 Suehiro-cho, Yokkaichi-shi, Mie Ito Oil Co., Ltd. (72) Inventor Seiji Kawaura 1-17-1 Doshomachi, Chuo-ku, Osaka-shi, Osaka Iwase Cosfa Co., Ltd. (72) Inventor Norio Matsuda 1-7-11 Doshomachi, Chuo-ku, Osaka City, Osaka Prefecture Iwase Cosfa Co., Ltd.

Claims (3)

[Claims] 1. A cationic surfactant comprising a reaction product of estolide (A), a diamine (B) having a primary or secondary amino group and a tertiary nitrogen, and a quaternizing agent (C). Cosmetic composition. 2. The cosmetic composition according to claim 1, wherein the estolide (A) is an intermolecular condensate of hydroxy fatty acid or a mixture of hydroxy fatty acid and a fatty acid having substantially no OH group. . 3. A cosmetic composition containing the cationic surfactant according to claim 1 and an anionic surfactant and / or an amphoteric surfactant.