JP2018052821A - Hair cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a hair cosmetic which imparts quick-drying properties to the hair itself after washing and imparts flexibility to the hair after drying in order to reduce the damage of the hair caused by thermal damage due to too much usage of a dryer to the wet hair after washing, friction damage due to a long time brushing, friction damage due to wiping off of moisture by scraping the hair with a towel more than necessary and friction damage due to sleeping with the hair wet.SOLUTION: There is provided a hair cosmetic comprising a perfluoropolyether compound represented by the general formula (1). (m represents an integer of 0 to 5, n represents an average integer of 1 to 20, Rrepresents an alkylene group having 2 to 6 carbon atoms, Rrepresents an alkyl group having total hydrogen or carbon number of 1 to 8, an aralkyl group or an aryl group, Rrepresents an alkyl group having total hydrogen or carbon number of 1 to 8, an aralkyl group or an aryl group, X represents fluorine or a perfluoroalkyl group having 1 to 3 carbon atoms and Z represents NH, N-CHor oxygen.)SELECTED DRAWING: None

Description

  The present invention relates to a novel hair cosmetic that imparts quick drying and flexibility to hair.

  Friction due to excessive use of hair dryer or long brushing on wet hair after shampooing, rubbing by wiping water more than necessary with towel after shampooing, hair still wet or insufficiently dried Friction due to going to bed is a factor, which causes great damage to hair. In order to alleviate these factors, it is important that the wet hair after shampooing dries immediately. Further, by giving the hair flexibility after drying, suppleness is born and friction caused by brushing or the like is reduced.

  Several hair cosmetics for the purpose of imparting quick-drying properties to hair have been developed so far (Patent Documents 1 to 4), and among them, it has been reported that quick-drying properties can be imparted by blending a fluorine-based compound. . (Patent Document 5). However, these hair cosmetics do not have a sufficient quick-drying effect even when compared with ordinary hair cosmetics that do not have a quick-drying effect. Furthermore, it has not been studied that hair cosmetics containing a fluorine compound having chemical binding properties to hair give quick drying properties, and the hair cosmetics simultaneously impart flexibility to the hair. It has not been considered that it can be done.

JP 2007-153806 A JP 2003-286137 A JP 2011-073991 A JP 2007-297299 A JP 2000-344633 A

  The purpose of the present invention is that heat damage caused by excessive use of a drier on wet hair after shampooing, frictional damage due to prolonged brushing, frictional damage caused by rubbing water more than necessary with a towel after shampooing, hair getting wet Providing hair cosmetics such as shampoos, conditioners and treatments that give quick drying to the hair itself after washing, and also give flexibility to the hair after drying, in order to reduce hair damage due to frictional damage caused by sleeping. There is.

  As a result of intensive studies, the present inventor has found that the perfluoropolyether compound having an amino group represented by the general formula (1) gives high quick-drying properties and flexibility to the hair, thereby completing the present invention. It came to.

  By using the cosmetic for hair containing the perfluoropolyether compound having an amino group represented by the general formula (1) which is the product of the present invention, the hair drains after shampooing is extremely good and quick drying. It was found that the hair after drying was excellent in flexibility. This is because the perfluoropolyether compound having an amino group represented by the general formula (1) related to the product of the present invention has a positive charge, so it is strongly adsorbed on the negatively charged hair, and the perfluoropolyether in the compound is further absorbed. It is considered that the polyether group was able to impart quick drying to the hair by inhibiting the moisture adsorption of the hair. In addition, it is considered that the chemical structure of the perfluoropolyether compound could impart flexibility to the hair.

（但し、ｍは０〜５の整数を表し、ｎは平均値で０〜２０の整数を表し、Ｒ^１は炭素数２〜６のアルキレン基を表し、Ｒ^２は水素原子または炭素数の合計が１〜８のアルキル基、アラルキル基、アリール基を表し、Ｒ^３は水素原子または炭素数の合計が１〜８のアルキル基、アラルキル基、アリール基を表し、Ｘはフッ素原子、または炭素数１〜３のパーフルオロアルキル基を表し、ＺはＮＨまたはＮ−ＣＨ_３または酸素原子を表す。）で示される、アミノ基を有するパーフルオロポリエーテル化合物を含有することを特徴とする毛髪に速乾性と柔軟性を付与することのできる毛髪用化粧料である。 Hereinafter, the compounds used in the present invention will be described in detail.
The present invention relates to a general formula (1);

(However, m represents an integer of 0 to 5, n represents an integer of 0 to 20 on average, R ¹ represents an alkylene group having 2 to 6 carbon atoms, and R ² represents a hydrogen atom or a total of carbon atoms. Represents an alkyl group, an aralkyl group or an aryl group having 1 to 8; R ³ represents a hydrogen atom or an alkyl group, an aralkyl group or an aryl group having a total of 1 to 8 carbon atoms; and X represents a fluorine atom or a carbon number. 1 to 3 perfluoroalkyl groups, Z represents NH or N—CH ₃ or an oxygen atom), and a perfluoropolyether compound having an amino group. It is a cosmetic for hair that can impart dryness and flexibility.

  If the X in the repeating structure of the perfluoropolyether compound having an amino group represented by the general formula (1) according to the present invention is a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, the hair can be quickly dried. And sufficiently exhibiting the effect of imparting flexibility, more preferably X is a trifluoromethyl group.

  The perfluoropolyether compound having an amino group represented by the general formula (1) according to the present invention can be synthesized with reference to, for example, US Pat. No. 3,547,995 and JP-A-2016-47812.

  The present invention provides a cosmetic for hair that can impart quick drying and flexibility to hair, which cannot be obtained conventionally, by containing a perfluoropolyether compound having an amino group represented by the general formula (1). It is to be done. The amount of the perfluoropolyether compound having an amino group represented by the general formula (1) in the hair cosmetic is not particularly limited, but it is 0.05 with respect to 100 parts by mass of the hair cosmetic. It is more preferable that the amount is not less than 80 parts by mass.

  The properties of the perfluoropolyether compound having an amino group represented by the general formula (1) according to the present invention are liquid to solid at room temperature depending on the type or molecular weight of X in the perfluoropolyether part. Further, since it has an amino group, the neutralized salt is dissolved or dispersed in water.

  The perfluoropolyether compound having an amino group represented by the general formula (1) according to the present invention exhibits sufficient quick-drying and flexibility effects even when used as it is without neutralization. It is more preferable to use a salt neutralized with a substance from the viewpoint of quick drying effect.

  The acidic substance used for neutralization is not particularly limited, and examples thereof include the following acidic substance. Moreover, you may use these acidic substances 1 type or in mixture of 2 or more types. Sulfuric acid, nitric acid, hydrochloric acid, phosphoric acid, silicic acid, carbonic acid, formic acid, acetic acid, propionic acid, benzoic acid, cinnamic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, adipic acid, tartaric acid, malic acid, citric acid, glutar Acid, sebacic acid, fumaric acid, maleic acid, mesylic acid, tosylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, behenic acid, sorbic acid, glutamic acid, aspartic acid, ascorbine Examples include acids and erythorbic acid. In particular, sulfuric acid, hydrochloric acid, and phosphoric acid are preferable in view of the water solubility of the salt to be formed.

  The hair cosmetic composition according to the present invention is not particularly limited. For example, hair cosmetics such as hair shampoos, hair conditioners, hair rinses, hair treatments, hair packs, etc. Charge.

  The hair cosmetic containing the perfluoropolyether compound having an amino group represented by the general formula (1) of the present invention is used for ordinary hair cosmetics as long as the effects of the present invention are not impaired. Various components such as a surfactant, an oily component, an active component, a moisturizing component, an antibacterial component, a viscosity modifier, and a fragrance can be blended.

  The present invention will be described more specifically with reference to the following examples. However, the technical scope of the present invention is not limited by these examples. A compounding quantity is the mass%.

1. Production of perfluoropolyether compound having amino group (Production of perfluoropolyether compound having amino group 1)
Based on the method disclosed in JP-A-2016-47812, a perfluoropolyether compound having an objective amino group represented by the following general formula (2) having an average degree of polymerization n = 8 was obtained.

(Production of amino group-containing perfluoropolyether compound 2)
Based on the method disclosed in JP-A-2016-47812, a perfluoropolyether compound having the target amino group represented by the following general formula (3) was obtained. M, n, X, and Z of the obtained compound are as shown in the present invention products 2 to 14 in Table 1 below.

(Creation of a shampoo containing a perfluoropolyether compound having an amino group)
The shampoo shown in the following formulation 1 was prepared, and the quick-drying property and the flexibility given to the hair of the perfluoropolyether compound having an amino group represented by the general formulas (2) and (3) according to the present invention were evaluated.

(Formulation 1): Shampoo A phase Perfluoropolyether compound having an amino group represented by general formula (2) or general formula (3) 1.0 (mass%)
Lauryl sulfate triethanolamine 10.0
Lauryldimethylaminoacetic acid betaine 3.0
Palm oil fatty acid diethanolamide 3.0
Ethylene glycol distearate 2.0
Edetate disodium 0.2
Preservative appropriate amount Phase B 1,3-butylene glycol 3.0
Phosphoric acid 0.5
Purified water balance (Preparation method)
The A phase component was heated and dissolved at 80 ° C., and the B phase component was added to the A phase component and stirred to make it uniform. Stirring was continued and cooled to 35 ° C to 30 ° C to obtain a shampoo.

2. Evaluation Method Using the shampoo shown in Formula 1, the quick-drying property that hair cosmetics containing a perfluoropolyether compound having an amino group represented by the general formulas (2) and (3) of the present invention give to hair Flexibility was evaluated. As a comparative product, instead of the perfluoropolyether compound having an amino group represented by the general formulas (2) and (3) of the present invention in the above formula 1, the polymerization degree n is extremely large and the perfluoropolyether compound having an amino group is used. A shampoo containing a fluoropolyether compound, perfluorohexaethylene glycol and perfluorooctanol was prepared and evaluated in the same manner.

(Evaluation of quick drying of hair)
After washing a hair bundle of healthy human hair (manufactured by Beaulux) for 2 minutes with a 5% aqueous solution of shampoo shown in Formula 1, rinse 30 times for 3 seconds, and then wipe off with a dry towel The increase in hair weight due to residual moisture was observed.

(Evaluation of hair flexibility)
25 females aged 35 years or younger were subjected to shampooing using the shampoo shown in Formula 1, and the softness to hair immediately after each shampooing drying and after 6 hours was evaluated according to the following criteria.

(Flexibility criteria)
A: 18 or more subjects answered that they had added flexibility to their hair.
○: 14 to 17 test subjects answered that they had added flexibility to the hair.
Δ: Eight to thirteen test subjects answered that they had added flexibility to the hair.
X: Seven or less test subjects answered that the hair was soft.

3. Evaluation results Table 1 shows the evaluation results. In the shampoo of Formula 1 containing the perfluoropolyether compound having an amino group represented by the general formulas (2) and (3) of the present invention, the hair bundle is dried just by wiping with a towel after washing, and the weight by moisture It was confirmed that there was almost no change. In addition, even when the perfluoropolyether compound having no amino group and the perfluoropolyether compound having an amino group are extremely high in the polymerization degree n, if m, n, and X are too long, moisture will be contained in the hair. Remained and an increase in the weight of the hair bundle was observed. On the other hand, the shampoo containing the perfluoropolyether compound having an amino group, which is the product of the present invention, also gave good flexibility to the hair, but the comparative product was evaluated to be inferior in use feeling such as the hair being stiff. was.

1. Production of perfluoropolyether compound having amino group (Production of perfluoropolyether compound having amino group 3)
Based on the method disclosed in Japanese Patent Application Laid-Open No. 2016-47812, a perfluoropolyether compound having a target amino group represented by the following general formula (4) was obtained. Z, R ¹ , R ² and R ³ of the obtained compound are as shown in Table 2 below.

2. Evaluation Method A shampoo shown in Formula 1 was prepared, and the quick-drying property and flexibility given to the hair of the perfluoropolyether compound having an amino group represented by the general formula (4) were evaluated. As a comparative product, a shampoo containing a perfluoropolyether compound not according to the present invention was prepared instead of the perfluoropolyether compound having an amino group, and the same evaluation was performed.

(Evaluation of quick drying of hair)
The evaluation was carried out in the same manner as the evaluation method described in Example 1.

(Evaluation of hair flexibility)
The evaluation was carried out in the same manner as the evaluation method described in Example 1.

(Flexibility criteria)
This was carried out in the same manner as the judgment criteria described in Example 1.

3. Evaluation results Table 2 shows the evaluation results. Even when a perfluoropolyether compound having an amino group of either an amide or an ester was used for the hair cosmetic, quick drying of the hair bundle was confirmed. When R ¹ , R ² , and R ³ are long-chain alkyl groups, a significant reduction in hair quick-drying was observed.

(Creation of a shampoo having a perfluoropolyether compound having an amino group)
The shampoo shown in Formula 2 was prepared, and the quick-drying property and flexibility given to the hair of the perfluoropolyether compound having an amino group represented by the general formula (2) were evaluated. Various acidic substances used here are as shown in Table 3 below.

(Formulation 2): Shampoo A phase having an amino group represented by the general formula (2)
Perfluoropolyether compound 2.0 (mass%)
Lauryl sulfate triethanolamine 7.0
N-lauryl sarcosine sodium 5.0
Palm oil fatty acid diethanolamide 3.0
Ethylene glycol distearate 2.0
Edetate disodium 0.2
Preservative appropriate amount Phase B 1,3-butylene glycol 3.0
Various acidic substances (or purified water) 0.5
Purified water balance

(Preparation method)
The A phase component was heated and dissolved at 80 ° C., and the B phase component was added to the A phase component and stirred to make it uniform. Stirring was continued and cooled to 35 ° C to 30 ° C to obtain a shampoo.

2. Evaluation Method The shampoo shown in Formula 2 was prepared, and the quick-drying property and softness given to the hair of the perfluoropolyether compound having an amino group represented by the general formula (2) were evaluated. As a comparative product, a shampoo containing a perfluoropolyether compound not according to the present invention was prepared instead of the perfluoropolyether compound having an amino group represented by the general formula (2), and the same evaluation was performed.

(Evaluation of quick drying of hair)
The evaluation was carried out in the same manner as the evaluation method described in Example 1.

(Evaluation of hair flexibility)
The evaluation was carried out in the same manner as the evaluation method described in Example 1.

(Flexibility criteria)
This was carried out in the same manner as the judgment criteria described in Example 1.

3. Evaluation Results Regardless of the type of acidic substance used in the shampoo shown in Formula 2, good quick-drying and flexibility were imparted to the hair. In addition, in the product 36 of the present invention using purified water instead of an acidic substance, quick drying and flexibility could be given to the hair.

  Below, the application example of the cosmetics for hair containing the perfluoro polyether compound which has an amino group represented by General formula (2) concerning this invention is shown. A compounding quantity is the mass%. Examples 4 to 6 were able to impart quick drying and flexibility to the hair.

Transparent shampoo (prescription)
A phase having an amino group represented by the general formula (2)
Perfluoropolyether compound 2.0 (mass%)
N-coconut oil fatty acid methyl taurine sodium 3.0
Polyoxyethylene (3) alkyl (12-15)
Sodium ether sulfate 10.0
Lauryldimethylaminoacetic acid betaine 3.0
Palm oil fatty acid diethanolamide 4.0
Preservative appropriate amount Phase B Citric acid 0.5
Propylene glycol 2.0
O- [2-hydroxy-3-chloride]
(Trimethylammonio) propyl] guar gum 0.5
Purified water balance (Preparation method)
The A-phase component and the B-phase component were dissolved by heating to 80 ° C., and the B-phase component was added to the A-phase component and stirred to make it uniform. Stirring was continued and it cooled to 35 to 30 degreeC, and the transparent shampoo was obtained.

Hair rinse (prescription)
Phase A Oleic acid dimethylaminopropylamide 1.0 (mass%)
Cetyl alcohol 2.0
Vaseline 2.0
Dimethylpolysiloxane 5.0
Liquid paraffin 1.0
Polyglyceryl stearate 2.0
Preservative Appropriate amount Perfume Small amount Phase B 1,3-butylene glycol 5.0
Cationized hydroxyethyl cellulose 0.5
Citric acid 1.0
Purified water remainder C phase having amino group represented by general formula (2)
Perfluoropolyether compound 2.0
Phosphoric acid 0.2
Purified water 10.0
(Preparation method)
A phase component and B phase component are heated to 80 ° C to dissolve, and after adding A phase component to B phase component and stirring to homogeneity, gradually add uniformly dissolved C phase component and continue stirring. The hair rinse was obtained by cooling to 30 ° C.

Hair treatment (prescription)
Phase A Stearic acid dimethylaminopropylamide 1.0 (mass%)
Behenyl alcohol 8.0
Cyclic silicone 8.0
Isostearyl alcohol 2.0
Dimethylpolysiloxane 1.0
Liquid paraffin 1.0
Polyglyceryl stearate 2.0
Preservative Appropriate amount Perfume Small amount Phase B 1,3-butylene glycol 5.0
Hydroxyethyl cellulose 0.5
Glutamic acid 0.8
Purified water remainder C phase having amino group represented by general formula (2)
Perfluoropolyether compound 2.0
Phosphoric acid 0.2
Purified water 10.0
(Preparation method)
The A phase component and the B phase component are dissolved by heating to 80 ° C., and the A phase component is added to the B phase component and stirred to homogeneity. Then, the uniformly dissolved C phase component is gradually added and the stirring is continued. The hair treatment was obtained by cooling to ℃.

  The cosmetic for hair containing the perfluoropolyether compound having an amino group represented by the general formula (1) of the present invention has an extremely high ability to impart quick-drying hair, which has not been conventionally available, In order to give flexibility, the industrial contribution is significant.

Claims (3)

A cosmetic for hair, comprising a perfluoropolyether compound having an amino group represented by the following general formula (1).

(Where, m represents an integer of 0 to 5, n represents an integer of 1 to 20 in average, ^{R 1} represents an alkylene group having 2 to 6 carbon atoms, ^{R 2} is the sum of hydrogen atoms or carbon atoms Represents an alkyl group, an aralkyl group or an aryl group having 1 to 8; R ³ represents a hydrogen atom or an alkyl group, an aralkyl group or an aryl group having a total of 1 to 8 carbon atoms; and X represents a fluorine atom or a carbon number. 1 to 3 perfluoroalkyl groups, and Z represents NH or N—CH ₃ or an oxygen atom.) The hair cosmetic according to claim 1, wherein X of the perfluoropolyether compound having an amino group represented by the general formula (1) is a trifluoromethyl group. The hair cosmetic according to any one of claims 1 to 2, wherein the perfluoropolyether compound having an amino group represented by the general formula (1) is used after being neutralized with an acidic substance.