KR20110109020A - Hair conditioning composition - Google Patents

Abstract

여기서, R 및 R'은 직쇄형 또는 분지형의 C_3-24 알케닐기 및 C_1-24 알킬기로 구성된 군으로부터 선택된다.The present invention relates to a hair conditioning composition, and more particularly, by including one or more alkenylalkylsuccinic esters having the structure of Formula 1 or 2 below, to impart gloss and softness to hair, and to maintain excellent conditioning effect and long-term. It relates to a hair conditioning composition which is free from buildup even in use.
[Formula 1] [Formula 2]

Wherein R and R 'are selected from the group consisting of straight or branched C _3-24 alkenyl groups and C _1-24 alkyl groups.

Description

Hair Conditioning Composition

The present invention relates to a hair conditioning composition, and more particularly, by including alkenylalkyl succinic ester as a novel hair conditioning material, to give gloss and softness to the hair, and to maintain excellent condition and to have no build-up phenomenon even after long-term use. The present invention relates to a hair conditioning composition.

The hair of modern people is contaminated by the exposure to ultraviolet light, contact with the surrounding environment such as dust, and sebum secreted from the hair follicles, which causes a lot of damage due to frequent perm, hair dry, dyeing and combing. Damaged hair can be difficult to handle, such as when wet or dried, tangled and stiff, poorly combed, and poorly glossy. Thus, consumers' demands and preferences for conditioning products that improve the appearance and feel of hair and make them easier to handle are increasing day by day.

The conditioning effect of hair is provided primarily through the use of cationic surfactants and hair conditioning agents such as polymers, silicones, hydrocarbon oils, glycerin, polyethylene glycols and fatty alcohols. Korean Unexamined Patent Publication No. 10-0743829 mentions that cationic surfactants with glyceryl groups can be introduced to solve complexes with anionic surfactants and promote coacervate formation to provide excellent conditioning, but with chemical damage. This severe hair lacks the conditioning effect.

Non-volatile silicone oils commonly used as hair conditioning ingredients provide gloss and flexibility to hair and provide softness to hair after drying, while being limited in their utility due to lack of moisturizing properties and poor compatibility with other ingredients. There is a problem that accumulates in the hair when used repeatedly for a long time, reduces the softness and accelerates recontamination by dust and sebum (Personal Care, 2005.11., P. 41 ~ 43). In particular, the polymer polysiloxane has a problem that the build-up phenomenon of stiffness of the hair is intensified because the polymer polysiloxane is not easily desorbed upon repeated use.

In Japanese Patent Publications H6-17097 and H7-11287, it is mentioned that the conditioning effect can be enhanced through polyvalent metal ions, anionic surfactants, amino acid surfactants and anionic surfactants, but conditioning by a combination of simple surfactants. Increased effectiveness is lacking in hair with severe chemical damage.

Consumers with severely damaged hair due to permalinking and dyeing need a better conditioning effect and require a composition that has a good feeling of use that is cumulative even after repeated use, but conventional hair conditioning compositions do not meet these requirements. .

The present invention was devised to solve the above-mentioned problems, and an object of the present invention is to provide an alkenylalkyl succinic ester as a novel hair conditioning material to give gloss and softness to the hair, and to maintain excellent condition and long-term use. It is to provide a hair conditioning composition without build-up phenomenon.

In addition, another object of the present invention is to impart gloss and softness to the hair, excellent condition maintenance effect, no build-up phenomenon even after long-term use, shampoo, conditioner, treatment, hair cream, conditioner, hair styling gel, hair mousse, hair Wax, hair tonic, hair essence, massage cream or hair dye.

The present invention for achieving the above object, provides a hair conditioning composition comprising at least one alkenylalkyl succinic ester having the structure of formula (1) or (2):

   [Formula 1] [Formula 2]

Wherein R and R 'are selected from the group consisting of straight or branched C _3-24 alkenyl groups and C _1-24 alkyl groups.

Therefore, the hair conditioning composition of the present invention has the advantage of providing gloss, gloss and softness to hair, excellent conditioning sustainability, and no build-up phenomenon even after long-term use.

The alkenylalkylsuccinic esters can be prepared by heating the anhydride form of alkenylsuccinic acid (ASA) with fatty alcohols. More specifically, the alkenylalkyl succinic ester can be obtained by heating the anhydride form of alkenyl succinic acid and fatty alcohol at 90 ° C to 110 ° C. The anhydride form of the alkenylsuccinic acid can be prepared according to the published synthetic process (USP-5021169) of maleic anhydride and olefins as a raw material that is generally used in a general coating agent for smoothly coating office paper.

The alkenylalkylsuccinic esters of the present invention can be prepared using not only the synthesis process described above but also other synthesis processes exhibiting substantially the same effect, and such other synthesis processes should also be construed as being included in the scope of the present invention.

The alkenylalkylsuccinic ester may be included in an amount of 0.01 to 5 parts by weight, preferably 0.01 to 1 part by weight, based on 100 parts by weight of the total composition. When included in less than 0.01 parts by weight it is difficult to achieve the object of the present invention to give an excellent conditioning effect, when exceeding 5 parts by weight may cause problems such as build up.

The hair conditioning composition comprising the alkenylalkylsuccinic ester of the present invention may be prepared in any form to impart gloss and softness to the hair. Specifically, the hair conditioning composition of the present invention is a shampoo, conditioner, treatment, hair dye, bleach, hair gel, hair conditioner, wool, hair tonic, hair cream, hair wax, hair spray, hair mousse, permanent wave composition, hair essence It is applicable to all hair cosmetic compositions for hair, such as massage creams. In addition, it can be applied to spray or spray type and can be used as a conditioner that does not need to be washed off with water separately.

The hair conditioning composition of the present invention as described above,

First, by including alkenylalkyl succinic ester which provides excellent conditioning effects such as gloss and softness to the hair, there is an advantage of improving the combing of the hair in wet and dry conditions and providing a smooth and soft texture for a long time.

Second, there is no build-up phenomenon in which the conditioning component accumulates on the hair, and thus the softness of the hair does not decrease even after long-term use.

Third, it can be included in a variety of hair cosmetics such as shampoo, conditioner, treatment as well as hair styling products, and can be used in hair essences, hair lotions, etc., which do not require cleaning after use.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings. Prior to this, terms or words used in the specification and claims should not be construed as having a conventional or dictionary meaning, and the inventors should properly explain the concept of terms in order to best explain their own invention. Based on the principle that can be defined, it should be interpreted as meaning and concept corresponding to the technical idea of the present invention.

Therefore, the configuration shown in the drawings and the embodiments described herein are only one of the most preferred embodiments of the present invention and do not represent all of the technical spirit of the present invention, various modifications that can be replaced at the time of the present application It should be understood that there may be equivalents and variations.

Example 1 Preparation of 2-dodecenyl dodecyl succinic ester

After adding 187 g of lauryl alcohol to the reactor, 266 g of 2-dodecenyldodecyl succinic anhydride was added. Stirring for 5-6 hours while maintaining the temperature of the reactor 80 ~ 100 ℃. After the reaction was completed, 451 g of clear yellow oily final product, 2-dodecenyldodecyl succinic ester was obtained. NMR analysis of this clear yellow oil confirmed that it was 2-dodecenyldodecyl succinic ester ( ¹ H-NMR (HSE-C1 ₂ (1: 0) -C1 ₂ ) 0.8 (6H, 2CH ₃ ), 1.2 (35H, (CH ₂ ) ₁₇ + CH), 1.6 (2H, CH ₂ ), 1.9 (2H, CH ₂ ), 2.5 (2H, CH ₂ ), 4.1 (2H, OCH ₂ ), 5.3 (1H, CH = C), 5.5 (1H, CH = C), 10.7 (1H, COOH).

<Examples 2 to 6> Preparation of a shampoo containing alkenylalkyl succinic ester

The shampoo containing the alkenylalkyl succinic ester was prepared by the following method, and the composition ratio of each example is shown in Table 1 below. The unit in Table 1 is parts by weight.

All components except paraoxybenzoic acid esters, fragrances and alkenylalkylsuccinic esters were heated to 60 ° C to dissolve uniformly, cooled to 40 ° C, and then paraoxybenzoic acid esters, fragrances and alkenylalkylsuccinic esters were added to the mixture. Added.

ingredient Example 2 Example 3 Example 4 Example 5 Example 6 Sodium Laureth-2sulfate 10 10 10 10 10 Pulping agent 10 10 10 10 10 2-dodecenyl dodecyl succinic ester 0.01 0.1 0.5 1.0 5.0 Dimethicone 1.0 1.0 1.0 1.0 1.0 Coca MIDA 0.5 0.5 0.5 0.5 0.5 Carboxy Vinyl Polymer 0.2 0.2 0.2 0.2 0.2 Jagua 0.2 0.2 0.2 0.2 0.2 Paraoxybenzoic acid ester 0.05 0.05 0.05 0.05 0.05 incense A reasonable amount A reasonable amount A reasonable amount A reasonable amount A reasonable amount Citric acid A reasonable amount A reasonable amount A reasonable amount A reasonable amount A reasonable amount Purified water Residual amount Residual amount Residual amount Residual amount Residual amount

Examples 7 to 9 Preparation of Rinse Containing Alkenylalkyl Succinate Ester

The rinse containing the alkenylalkyl succinic ester was prepared by the following method, and the composition ratio of each example is shown in Table 2 below. The unit in Table 2 is parts by weight.

All components except paraoxybenzoic acid ester, fragrance and gujeolcho extract were purified to warm to 75 ° C, and then emulsified uniformly, cooled to 50 ° C, and then paraoxybenzoic acid ester, aroma and alkenylalkyl succinic ester were added to the purified water. It was.

ingredient Example 7 Example 8 Example 9 Cetyl alcohol 2.0 2.0 3.0 Stearyl alcohol 3.0 3.0 3.0 Behentrimonium chloride 1.5 1.5 1.5 Cyclomethicone 2.0 2.0 2.0 2-dodecenyl dodecyl succinic ester 0.1 0.5 1.0 Ammody Methicone 1.0 1.0 1.0 Panthenol 0.05 0.05 0.05 incense A reasonable amount A reasonable amount A reasonable amount Citric acid A reasonable amount A reasonable amount A reasonable amount Purified water Residual amount Residual amount Residual amount

Examples 10 to 12 Preparation of Hair Waxes Containing Alkenylalkylsuccinic Esters

Hair waxes containing the alkenylalkylsuccinic esters were prepared by conventional methods known in the art, and the composition ratios of the examples are shown in Table 3 below. The unit in Table 3 is parts by weight.

ingredient Example 10 Example 11 Example 12 Microcrystalline Wax 25 25 25 Carnauba wax 10 10 10 C20-40 Palace 10 3 3 3 Petrolatum 16 16 16 2-dodecenyl dodecyl succinic ester 0.1 0.5 1.0 Hydrated Aluminum Silicate 15 15 15 Polyethylene 3 3 3 Glyceryl Stearate 2 2 2 Pigment 0.15 0.15 0.15 incense 0.4 0.4 0.4 Mineral oil Residual amount Residual amount Residual amount

Examples 13 to 15 Preparation of Hair Essences Containing Alkenylalkylsuccinic Esters

Hair essences containing the alkenylalkylsuccinic esters were prepared by conventional methods known in the art, and the composition ratios of the respective examples are shown in Table 4 below. The unit in Table 4 is parts by weight.

ingredient Example 13 Example 14 Example 15 Polysorbate 60 1.0 1.0 1.0 2-dodecenyl dodecyl succinic ester 0.1 0.5 1.0 Dimethicone 2.0 2.0 2.0 Difanthenol 0.3 0.3 0.3 Dicaprylylcarbonate 10 10 10 Polyquaternium-37 (50% dispersion) 2.0 2.0 2.0 DMH Hydantoin 0.15 0.15 0.15 incense A reasonable amount A reasonable amount A reasonable amount Purified water Residual amount Residual amount Residual amount

Comparative Example 1 Preparation of Shampoo Without Alkenylalkyl Succinic Ester

Shampoo according to the composition ratio of Table 5 was prepared in the same manner as in Examples 2 to 6. The unit in Table 5 is parts by weight.

ingredient Comparative Example 1 Sodium Laureth-2sulfate 10 Pulping agent 10 2-dodecenyl dodecyl succinic ester - Dimethicone 1.0 Coca MIDA 0.5 Carboxy Vinyl Polymer 0.2 Jagua 0.2 Paraoxybenzoic acid ester 0.05 incense A reasonable amount Citric acid A reasonable amount Purified water Residual amount

Comparative Example 2 Preparation of Rinse Without Alkenylalkyl Succinate Ester

To rinse according to the composition ratio of Table 6 was prepared in the same manner as in Examples 7 to 9. The unit in Table 6 is parts by weight.

ingredient Comparative Example 2 Cetyl alcohol 2.0 Stearyl alcohol 3.0 Behentrimonium chloride 1.5 Cyclomethicone 2.0 2-dodecenyl dodecyl succinic ester - Ammody Methicone 1.0 Panthenol 0.05 incense A reasonable amount Citric acid A reasonable amount Purified water Residual amount

Comparative Example 3 Preparation of Hair Wax without Alkenylalkyl Succinate Ester

A non-aqueous hair styling wax according to the composition ratio of Table 7 was prepared in the same manner as in Examples 10 to 12. The unit in Table 7 is parts by weight.

ingredient Comparative Example 3 Microcrystalline Wax 25 Carnauba wax 10 C20-40 Palace 10 3 Petrolatum 16 2-dodecenyl dodecyl succinic ester - Hydrated Aluminum Silicate 15 Polyethylene 3 Glyceryl Stearate 2 Pigment 0.15 incense 0.4 Mineral oil Residual amount

Comparative Example 4 Preparation of Hair Essence Without Alkenylalkyl Succinate Ester

To the hair essence according to the composition ratio of Table 8 was prepared in the same manner as in Examples 13-15. The units in Table 8 below are parts by weight.

ingredient Comparative Example 4 Polysorbate 60 1.0 2-dodecenyl dodecyl succinic ester - Dimethicone 2.0 Difanthenol 0.3 Dicaprylylcarbonate 10 Polyquaternium-37 (50% dispersion) 2.0 DMH Hydantoin 0.15 incense A reasonable amount Purified water Residual amount

Experimental Example 1 Evaluation of Conditioning Effect of Shampoo

The conditioning effect of the shampoos prepared in Examples 2 to 6 and Comparative Example 1 was evaluated. 100 women aged 25 to 40 with hair damaged due to dyeing and perm were selected and compared for the evaluation items shown in Table 10 below for one month. The test was conducted with a high score of 5 points. The test results are shown in Table 9 below.

Evaluation Item Example 2 Example 3 Example 4 Example 5 Example 6 Comparative Example 1 Rich amount of bubbles in shampoo 4.5 4.5 4.3 4.3 4.1 3.5 Good feeling of bubbles when shampooing 4.0 4.8 4.5 4.2 4.2 3.9 Hair does not tangle during shampooing 4.1 4.2 4.4 4.5 4.5 3.5 Hair does not tangle during rinsing 4.2 4.7 4.6 4.8 4.7 2.5 Soft hair when rinsing 3.8 4.4 4.5 4.1 4.0 2.1 Soft hair after rinsing 4.5 4.4 4.5 4.5 4.3 2.0 Hair is soft after drying 3.9 4.3 4.0 4.0 4.0 3.3 Hair is not sticky when used repeatedly 4.3 4.3 4.3 4.2 3.8 4.0

According to the above Table 9, the shampoo of the present invention including the alkenylalkyl succinic ester was better than the shampoo of Comparative Example 1 containing no alkenylalkyl succinic ester, the feeling of bubbles during shampooing, hair was not tangled, rinse And even after drying, the hair is soft and it can be seen that the conditioning effect is excellent. In addition, it can be seen that the build-up phenomenon does not appear because the hair is not sticky even when used repeatedly.

However, the hair sticking item in repeated use is a side effect item that may appear when the conditioning effect to soften the hair is excellent. Therefore, in Comparative Example 1, since there is almost no conditioning component, it is natural to have less hair stickiness, but in the case of Example, it can be judged that there is no side effect of hair stickiness despite excellent hair conditioning.

Experimental Example 2 Evaluation of Conditioning Effect of Rinse

The usability and conditioning evaluation of the rinse prepared in Examples 7 to 9 and Comparative Example 2 was carried out. Evaluation method was performed by the same five-point evaluation method as Experimental Example 1 and the results are shown in Table 10 below.

Evaluation Item Example 7 Example 8 Example 9 Comparative Example 2 Soft hair when applied 4.1 4.6 4.6 3.5 Soft hair when rinsing 4.2 4.5 4.7 3.7 Soft hair after drying 4.1 4.3 4.2 3.5 Conditioning lasts. 4.2 4.2 4.2 3.5 Hair is not sticky when used repeatedly 4.5 4.5 4.5 3.2

According to Table 10, the rinse of the present invention containing an alkenylalkyl succinic ester was softer in use, better in wet and dry hair than the rinse of Comparative Example 2 containing no alkenylalkyl succinic ester. And scored high on all items. In addition, the hair was not sticky when used repeatedly, and the buildup phenomenon did not appear.

Experimental Example 3 Evaluation of Conditioning Effect of Hair Styling Wax

The conditioning effects of the hair styling waxes of Examples 10-12 and Comparative Example 3 were evaluated. Ten males, 25-35 years old, using the usual styling products in wax formulations were selected and dried after hair washing to use the wax products of the examples and comparative examples. Each product was evaluated according to the evaluation items of Table 11 below, and the results are shown in Table 11 below.

Evaluation Item Example 10 Example 11 Example 12 Comparative Example 3 Application to hair 3.6 3.8 3.8 3.1 Style setting 3.6 3.5 3.5 3.2 Ease of restyling 3.8 3.9 4.1 3.1 Softness of hair 3.9 4.2 4.2 3.2 Overall satisfaction 3.8 3.9 3.8 3.2

According to Table 11, the wax of the present invention containing the alkenylalkyl succinic ester was excellent in all items compared to the wax of Comparative Example 3 containing no alkenylalkyl succinic ester, in particular, the softness of the hair Easiness of restyling was appreciated. This improves the hair's flexibility, which makes it easier to restyling. Overall product satisfaction was also higher than the wax of the comparative example.

Experimental Example 4 Evaluation of Feeling and Conditioning Effect of Hair Essence

The feeling and conditioning effects of the hair essences prepared in Examples 13 to 15 and Comparative Example 4 were carried out in the same manner as in Experimental Example 1 and the results are shown in Table 12 below.

Evaluation Item Example 13 Example 14 Example 15 Comparative Example 4 Hair softness after application 4.5 4.5 4.7 3.3 Soft Passive 4.2 4.3 4.3 3.1 burnish 4.1 4.2 4.2 3.2 Hair is not sticky when repeated 4.2 4.2 4.3 4.1

According to Table 12, the hair essences of Examples 13 to 15 containing alkenylalkyl succinic esters have excellent hair softness and softness lasting effects, and in particular, the ability to impart gloss to hair includes alkenyl alkyl succinic esters. Better than essence not. In addition, the hair does not become sticky even after repeated use.

<Experiment 5> combing feeling evaluation

In order to evaluate the conditioning efficacy of the products of Examples and Comparative Examples, a combing evaluation experiment on wet hair and dry hair was conducted using an Instron (Universal Test Machine, Instron Model 4465 Test System).

The combing of wet hair was evaluated using virgin hair of Asian women purchased from De-Meo Brothers, USA, followed by a 10% Sodium Laureth Sulfate (SLS) solution. After washing, rinse with plenty of water and remove excess water with a finger sweep. The wet hair bundle was fastened to the load cell loop of the Instron, the comb was fixed using a jig, and the load value of the comb was measured by operating the Instron.

To evaluate the combing feeling of dried hair, the same hair was completely dried with a towel and a dryer, and then left in a constant temperature and humidity room for 2 hours, and then tested on the same method as the wet hair.

Each of the tested hair bundles was coated with 1 g of the compositions of Examples 4, 8 and 14, Comparative Examples 1, 2 and 4, rinsed for 30 seconds and subjected to combing evaluation by the method described above. 3 or more hair bundles were prepared for each composition, tested 3 times or more for each item, and the average value of the load value was calculated, and then the reduction rate of the average load value after the treatment for the average load value after the untreated treatment of the composition. The preponderance of combing was evaluated. The rate of change of the average load after untreated / treated compositions of the compositions of the above examples and the comparative examples was evaluated in percent (%), and the results are shown in Table 13.

Under the conditions of evaluation, the weight of the hair bundle was 10 g and the length was 20 cm, and the comb was made of a cylindrical matt stainless steel comb. The comb diameter was 1 mm and the spacing between the combs was 1 mm. . Instron's cross head speed was 500.00 mm / min, load cell was 10.0 kg / Limit Type, and displacement was 200.00 mm.

Evaluation Item Example 4 Example 8 Example 14 compare
Example 1 compare
Example 2 compare
Example 4 Average load reduction rate for wet hair -74 -81 -88 -38 -45 -47 Average load reduction rate of dried hair -71 -85 -87 -35 -39 -43

In Table 13, the larger the negative value, the better the combing feeling. The results indicate that the hair using the shampoos, rinses, and essences of Examples 4, 8, and 14 containing alkenylalkylsuccinic esters had better combing compared to the hairs of Comparative Examples 1, 2, and 4. Can be.

Experimental Example 7 Evaluation of Gloss

EXAMPLES AND COMPARATIVE EXAMPLES Hair gloss evaluation experiments were conducted using hair tress to evaluate the conditioning efficacy of the composition.

First, hairs were made from normal hair of Asian women purchased from De-Meo Brothers, USA, washed with 10% aqueous SLS solution, rinsed with sufficient water, and naturally dried. Evaluation conditions were that the weight of the hair bundle is 10 g, 20 cm in length, 3 g of the same shampoo is applied for 1 minute and then washed with running water for 30 seconds, and Examples 4, 8 and 11, Comparative Examples 1, 2 and 4 The composition was applied to 3 g of different hair bundles, left for 1 minute, washed with running water for 30 seconds, and dried naturally.

The hair bundles subjected to the above treatment were randomly arranged to 20 professional panelists with experience in organoleptic evaluation of hair products, and evaluated according to the following evaluation criteria, and the results are shown in Table 14.

* Evaluation standard

5 points: High gloss and outstanding

4 points; Glossy and excellent

3 points: normal

2 points: no gloss

1 point: no gloss

Evaluation Item Example 4 Example 8 Example 14 compare
Example 1 compare
Example 2 compare
Example 4 Glossiness in dry condition 3.8 4.1 4.5 3.1 3.3. 3.5

According to Table 14, the shampoo of Example 4, the rinse of Example 8 and the essence of Example 14 containing alkenylalkyl succinic ester showed excellent glossiness compared to the comparative example.

As described above, the hair conditioning composition comprising the alkenylalkyl succinic ester of the present invention is excellent in the effect of imparting gloss and softness to hair and sustaining conditioning, and thus can be used to impart conditioning effects to various hair cosmetic compositions. It does not show any buildup phenomenon even after long use.

Claims (3)

A hair conditioning composition comprising one or more alkenylalkylsuccinic esters having the structure of Formula 1 or 2:
[Formula 1] [Formula 2]

Wherein R and R 'are selected from the group consisting of straight or branched C _3-24 alkenyl groups and C _1-24 alkyl groups. The hair conditioning composition of claim 1, wherein the alkenylalkylsuccinic ester is included in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the total composition. 2. Hair conditioning according to claim 1, wherein the formulation of the composition is a shampoo, rinse, treatment, hair cream, conditioner, hair styling gel, hair mousse, hair wax, hair tonic, hair essence, massage cream or hair dye. Composition.