JP4700319B2 - Wax-like fatty acid ester and hair cosmetic composition containing the same - Google Patents

Description

  The present invention relates to a novel waxy fatty acid ester and a hair cosmetic composition containing the same, such as a hair rinse, a hair conditioner, and a hair treatment.

  Conventionally, hair cosmetic compositions such as hair rinses, hair conditioners, hair treatments and the like have been used to impart functions such as “smooth feeling” and “moist and coherent feeling” to hair. These are O / W emulsions emulsified using a composite gel composed of a cationic surfactant such as a quaternary ammonium salt and a higher alcohol. Examples of oil components other than these include silicone oils such as amino-modified silicone and methylpolysiloxane polymers, glycerides, liquid paraffin, ester oils, and various vegetable oils. When classified according to the oils to be blended, the silicone oils alone prescription system and the prescription system that uses two or more of silicone oils and oils other than silicone oils (glyceride, liquid paraffin, ester oil, various vegetable oils, etc.) in combination 2 It is a big picture. These oils are blended exclusively in order to express a “smooth feeling”, “moist and coherent feeling”, and the like. However, hair cosmetic compositions containing these oils have a strong squeaky feeling during rinsing and have a problem in use.

Therefore, there is a content in which higher alcohol and 1 to 1,000 mm ² / S hydrophobic silicones (for example, aliphatic alcohol-modified polysiloxane) are used in combination as an oil component of a hair cosmetic composition using a cationic surfactant. It is reported in Patent Document 1. However, the disclosed hair cosmetics have improved the smoothness of the hair after drying (“smooth feeling”), but have sufficiently improved the stickiness of the hair and the squeaky feeling during rinsing. There was no problem.

In addition, the silicone oils single prescription system is slightly less squeaky during rinsing than the prescription system using two or more oils in combination, but it lacks the “moist and cohesive feeling” after drying. There is a need to improve. In this respect, Patent Document 2 reports a silicone oil obtained by modifying a silicone with a sterol. Since this has good adhesion to the skin and also has an effect of reducing the stickiness to the skin, it can be sufficiently considered for use in a hair cosmetic composition. However, Patent Document 3 reports that this sterol-modified silicone oil has insufficient adhesion to hair and has insufficient function to retain moisture in hair ("moist feeling"). . In addition, glycerides, liquid paraffin, ester oils, and various vegetable oils give a moist feeling to the hair after drying compared to silicone oils. However, in order to express a strong squeaky feeling during rinsing, Oils have their merits and demerits, and the development of oils that satisfy all requirements has been desired.
JP 56-92808 JP-A-4-145097 JP 7-316024 A

  The present invention overcomes the problems of the prior art as described above. When used in a hair cosmetic composition such as a hair rinse, a hair conditioner, or a hair treatment, the squeaky feeling during rinsing, which has been a drawback of conventional oils. For the development of a waxy fatty acid ester that is an oil that has an excellent effect of imparting a moist and coherent feeling to the hair after drying, and to provide a hair cosmetic composition containing the same And

As a result of intensive studies to solve the above problems, the present inventors have found that a specific glycerin fatty acid ester can solve the above problems, and have completed the present invention. That is, according to the present invention, the molar ratio of hydroxystearic acid: oleic acid is 9.0: 1 with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of glycerin and / or a dehydration condensate thereof of 3 or less. A waxy fatty acid ester obtained by esterifying 0.5 to 2.0 mol of a mixed fatty acid composed of 0.0 to 4.0: 6.0, or the following components (1) to (2):
(1) Hydroxyesterified from 0.5 to 2.0 mol of hydroxystearic acid with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from the hydroxyl value of glycerin and / or its dehydration condensate of 3 or less. Stearic acid ester.
(2) Oleic acid obtained by esterifying 0.5 to 2.0 mol of oleic acid with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of glycerin and / or a dehydration condensate thereof of 3 or less. ester.
A waxy fatty acid ester having a weight ratio of (1) to (2) of 3.0: 7.0 to 7.0: 3.0, and a hair cosmetic composition containing these waxy fatty acid esters It is about things.

  When the waxy fatty acid ester of the present invention is used in a hair cosmetic composition such as a hair rinse, a hair conditioner, or a hair treatment, it does not exhibit a squeaky feeling during rinsing, which has been a drawback of conventional oils, and is applied to the hair after drying. It is possible to obtain a hair cosmetic composition excellent in the effect of imparting a “moist and coherent feeling”.

  The present invention is described in detail below.

  The glycerin used in the present invention and / or its dehydration condensate and the polyglycerin having an average degree of polymerization calculated from the hydroxyl value of 3 or less are glycerin commonly used in cosmetics, and the glycerin is used as a raw material for dehydration condensation. This refers to polyglycerol obtained by reaction, such as diglycerol and triglycerol. When a fatty acid ester synthesized using polyglycerin having an average degree of polymerization exceeding 3 is blended in a hair cosmetic, there is a problem that the hair after washing is stiff, such being undesirable.

  The hydroxystearic acid and oleic acid used in the present invention are not particularly limited, and the odor and hue of the obtained waxy fatty acid ester are preferable because they are usually used in cosmetics. In addition, if the origin is plant-based, animal-derived raw materials are still more preferable as a shy cosmetic raw material.

  Next, a mixed fatty acid having a molar ratio of hydroxystearic acid: oleic acid of 9.0: 1.0 to 4.0: 6.0 with respect to 1.0 mol of glycerin and / or a dehydrated condensate thereof. 0.5 to 2.0 mol of the ester is esterified to synthesize a waxy fatty acid ester. When the molar ratio of hydroxystearic acid: oleic acid is outside the above range, for example, the ester obtained by increasing the amount of hydroxystearic acid (decreasing the amount of oleic acid) is used in a hair cosmetic composition, squeaky feeling during rinsing Will appear. On the contrary, when the amount of oleic acid increases (the amount of hydroxystearic acid decreases), the effect of imparting a “moist and coherent feeling” after drying decreases. Also, 0.5 to 2.0 moles of these mixed fatty acids are esterified, but if it is outside this range, for example, less than 0.5 moles, the function as an oil becomes difficult to develop and the tendency to be washed away during rinsing becomes stronger. It is not possible to demonstrate sufficient functions. On the other hand, an ester synthesized in excess of 2.0 moles is not preferable because a feeling of residual oil after drying, that is, oily stickiness, appears.

The waxy fatty acid ester of the present invention can be synthesized by a batch reaction using mixed fatty acids as described above, and the desired waxy ester can be synthesized by synthesizing each fatty acid ester and blending them. Either method of obtaining the fatty acid ester may be selected. When blending two types of fatty acid esters, the following components (1) to (2):
(1) 0.5 to 2.0 mol of hydroxystearic acid, preferably 1. with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of glycerin and / or its dehydration condensate of 3 or less. Hydroxy stearic acid ester obtained by esterifying 0 to 2.0 mol.
(2) 0.5 to 2.0 moles of oleic acid, preferably 0.5 to 1.0 mole of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of glycerin and / or a dehydration condensate thereof of 3 or less. Oleate esterified with ~ 1.5 mol.
And a weight ratio of (1) to (2) is 3.0: 7.0 to 7.0: 3.0 to obtain a waxy fatty acid ester. The feed ratio of the hydroxy stearate ester of (1) is preferably in the above range. When an ester obtained with a hydroxystearic acid of less than 0.5 is blended in a hair cosmetic composition, the effect of imparting a “moist and coherent feeling” after drying is reduced. On the other hand, when the amount exceeds 2.0 mol, a feeling of residual oil after drying, that is, an oily stickiness is developed, which is not preferable. The charge ratio of the oleic acid ester (2) is preferably in the above range. If the oleic acid is less than 0.5, a squeaky feeling during rinsing will appear. On the other hand, if it exceeds 2.0 moles, the feeling of slime during rinsing becomes too strong, and rinsing becomes difficult. In addition, the weight ratio of (1) hydroxystearic acid ester to (2) oleic acid ester is outside the above range, for example, an ester obtained by increasing the amount of hydroxystearic acid ester (decreasing the amount of oleic acid ester) When used in a composition, a squeaky feeling during rinsing is developed. Conversely, when the amount of oleic acid ester is increased (the amount of hydroxystearic acid ester is decreased), the effect of imparting a “moist and coherent feeling” after drying is reduced.

  The waxy fatty acid ester obtained by the above method is blended in a hair cosmetic composition such as a hair rinse, a hair conditioner, or a hair treatment. There is no particular limitation on the compounding, and it can be easily compounded into a prescription system comprising a generally established cationic surfactant and a higher alcohol. Although there is no restriction | limiting in a compounding quantity, The use of the same amount as the oil component normally mix | blended with these prescription systems, for example, about 1 to 10% is preferable.

  In the hair cosmetic composition of the present invention, components used in ordinary cosmetic compositions and the like within the range not impairing the effects of the invention, such as squalane, liquid paraffin, isopropyl myristate, cetyl octanoate, glyceryl trioctanoate , Dimethylpolysiloxane, petroleum jelly, hydrogenated palm oil, jojoba oil, olive oil, cetanol, stearyl alcohol, lauric acid, stearic acid and other oils, polyoxyethylene alkyl ether, polyglycerin fatty acid ester and other surfactants, propylene Mix appropriately with polyhydric alcohols such as glycol and glycerin, water-soluble polymers such as hydroxyethyl cellulose and carboxyvinyl polymer, various vitamins, amino acids, herbal medicines, anti-inflammatory agents, cell activators, pigments, preservatives, and fragrances. Can do.

  EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention concretely, the scope of the present invention is not limited by these Examples.

<Example 1>
The fatty acid ester was synthesized as follows.
A mixed fatty acid composed of 100 g of glycerin, 163 g of hydroxystearic acid and 153 g of oleic acid (molar ratio 5: 5, 1 mol of mixed fatty acid per 1 mol of glycerin) was put in a reaction vessel, 0.2 g of sodium hydroxide was added, The reaction was carried out under a nitrogen stream at 250 ° C. for 4 hours to obtain 376 g of a waxy fatty acid ester.

<Example 2>
A mixed fatty acid composed of 100 g of glycerin, 352 g of hydroxystearic acid and 221 g of oleic acid (molar ratio 6: 4, 1.8 mol of mixed fatty acid per 1 mol of glycerin) is put in a reaction vessel and reacted under the same conditions as in Example 1. This gave 606 g of a waxy fatty acid ester.

<Example 3>
A mixed fatty acid composed of 100 g of diglycerin, 253 g of hydroxystearic acid and 102 g of oleic acid (molar ratio 7: 3, mixed fatty acid 2 mol per 1 mol of diglycerin) is put in a reaction vessel and reacted under the same conditions as in Example 1. This gave 412 g of a waxy fatty acid ester.

<Example 4>
100 g of glycerin and 489 g of hydroxystearic acid (1.5 mol of fatty acid with respect to 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 532 g of hydroxystearic acid ester. Next, 100 g of glycerin and 307 g of oleic acid (1 mol of fatty acid per 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 387 g of oleic acid ester. The resulting glycerin hydroxystearate and glycerin oleate were mixed so that the weight ratio was 4: 6 to obtain a waxy fatty acid ester.

<Example 5>
100 g of glycerin and 652 g of hydroxystearic acid (2 mol of fatty acid per 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 677 g of hydroxystearic acid ester. Next, 100 g of glycerin and 460 g of oleic acid (1.5 mol of fatty acid with respect to 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 504 g of oleic acid ester. The resulting glycerin hydroxystearate and glycerin oleate were mixed so that the weight ratio was 5: 5 to obtain a waxy fatty acid ester.

<Example 6>
100 g of diglycerin and 361 g of hydroxystearic acid (2 mol of fatty acid with respect to 1 mol of diglycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 417 g of hydroxystearic acid ester. Next, 100 g of glycerin and 460 g of oleic acid (1.5 mol of fatty acid with respect to 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 504 g of oleic acid ester. The resulting hydroxy stearic acid diglycerin and oleic acid glycerin were mixed at a weight ratio of 3: 7 to obtain a waxy fatty acid ester.

<Comparative example 1>
A mixed fatty acid consisting of 100 g of glycerin, 65 g of hydroxystearic acid and 245 g of oleic acid (molar ratio 2: 8, 1 mol of mixed fatty acid per 1 mol of glycerin) is put in a reaction vessel and reacted under the same conditions as in Example 1. 371 g of fatty acid ester was obtained.

<Comparative example 2>
A mixed fatty acid composed of 100 g of glycerin, 245 g of hydroxystearic acid and 536 g of oleic acid (molar ratio 3: 7, 2.5 mol of mixed fatty acid with respect to 1 mol of glycerin) is put in a reaction vessel and reacted under the same conditions as in Example 1. And 790 g of fatty acid ester was obtained.

<Comparative Example 3>
A mixed fatty acid composed of 100 g of diglycerin, 271 g of hydroxystearic acid, and 255 g of oleic acid (molar ratio 5: 5, 3 mol of mixed fatty acid to 1 mol of diglycerin) is put in a reaction vessel and reacted under the same conditions as in Example 1. And 564 g of fatty acid ester was obtained.

<Comparative example 4>
100 g of glycerin and 978 g of hydroxystearic acid (3 mols of fatty acid per 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 968 g of hydroxystearic acid ester. Next, 100 g of glycerin and 307 g of oleic acid (1 mol of fatty acid with respect to 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 368 g of oleic acid ester. The resulting glycerin hydroxystearate and glycerin oleate were mixed so that the weight ratio was 1: 9 to obtain a fatty acid ester.

<Comparative Example 5>
100 g of glycerin and 652 g of hydroxystearic acid (2 mol of fatty acid per 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 677 g of hydroxystearic acid ester. Next, 100 g of glycerin and 613 g of oleic acid (2 mol of fatty acid with respect to 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 640 g of oleic acid ester. The resulting glycerin hydroxystearate and glycerin oleate were mixed so that the weight ratio was 2: 8 to obtain a fatty acid ester.

<Comparative Example 6>
100 g of diglycerin and 815 g of hydroxystearic acid (2.5 mol of fatty acid with respect to 1 mol of diglycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 823 g of hydroxystearic acid ester. Next, 100 g of glycerin and 613 g of oleic acid (2 mol of fatty acid with respect to 1 mol of glycerin) were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 640 g of oleic acid ester. The resulting hydroxy stearic acid diglycerin and oleic acid glycerin were mixed at a weight ratio of 4: 6 to obtain a fatty acid ester.

<Comparative Example 7>
A mixed fatty acid composed of 100 g of glycerin, 278 g of stearic acid, and 185 g of isostearic acid (molar ratio 6: 4, 1.5 mol of mixed fatty acid per 1 mol of glycerin) is put in a reaction vessel and reacted under the same conditions as in Example 1. 507 g of fatty acid ester was obtained.

Esters obtained in Examples and Comparative Examples were blended into the following rinse formulations and used by 20 healthy panelists, and “feeling of creaking during rinsing” and “feeling of moistness and cohesion after drying” were used. The sensory evaluation was carried out. Evaluation was carried out according to the following absolute evaluation criteria, with 5 grades, and the average value of the scores was judged using the 4 grade criteria. The results are shown in Table 1.
・ Absolute evaluation criteria ・ 4-step criteria (rating): (evaluation) (average score): (determination)
5 points: Very good 4.5 points or more: ◎
4 points: Good 4.0 points or more and less than 4.5 points: ○
3 points: Normal 3.0 points or more and less than 4.0 points: △
2 points: Slightly less than 3.0 points: ×
1 point: Poor ・ Rinse formulation Behenyltrimethylammonium chloride (80%): 1.5%
Stearyl alcohol: 4.5%
Esters obtained in Examples and Comparative Examples: 3.0%
High polymerization degree dimethylpolysiloxane: 0.5%
Glycerin: 10.0%
Purified water: 80.5%

  The hair rinses containing the waxy fatty acid esters obtained in Examples 1 to 6 were excellent in usability such as “no squeaky feeling during rinsing” and “moist feeling after drying”. On the other hand, the hair rinse which mix | blended the fatty acid ester obtained by Comparative Examples 1-7 was not satisfied in usability.

  Moreover, the waxy fatty acid ester of the present invention can be used not only for the above-mentioned in-bath products but also for out-bath products such as hair milk and hair wax. The prescription example is described below.

Example 7 Hair Milk Lotion Phase A (wt%)
Glycerin 5.00
Decaglyceryl monomyristate 3.00
Waxy fatty acid ester of Example 1 1.00
Phase B 1% -carboxyvinyl polymer 5.00
10% -potassium hydroxide aqueous solution 1.00
1,3-butylene glycol 5.00
Purified water 80.00
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the mixture was cooled to 35 ° C. to obtain a hair milk lotion.

Example 8 Hair wax A phase (% by weight)
Waxy fatty acid ester of Example 5 7.50
Vaseline 5.00
Decaglyceryl monooleate 2.00
Stearic acid 3.50
Glycerol monostearate 2.00
Glyceryl tri-2-ethylhexanoate 5.00
Phase B Glycerin 7.00
10% -potassium hydroxide aqueous solution 1.00
Purified water 67.00
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the hair wax was obtained by cooling to 35 ° C.
The hair cosmetic composition shown above was satisfactory in terms of use.

When the waxy fatty acid ester of the present invention is used in a hair cosmetic composition such as a hair rinse, a hair conditioner, a hair treatment, etc., the hair after drying does not exhibit a squeaky feeling during rinsing, which has been a drawback of conventional oils. It is possible to obtain a hair cosmetic composition excellent in the effect of imparting a “moist and coherent feeling” to the skin.

Claims (3)

The molar ratio of hydroxystearic acid: oleic acid is 9.0: 1.0 to 4.4 with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of glycerin and / or its dehydration condensate of 3 or less. 0: A waxy fatty acid ester obtained by esterifying 0.5 to 2.0 mol of a mixed fatty acid composed of 6.0. The following components (1) to (2):
(1) Hydroxyesterified from 0.5 to 2.0 mol of hydroxystearic acid with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from the hydroxyl value of glycerin and / or its dehydration condensate of 3 or less. Stearic acid ester.
(2) Oleic acid obtained by esterifying 0.5 to 2.0 mol of oleic acid with respect to 1.0 mol of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of glycerin and / or a dehydration condensate thereof of 3 or less. ester.
A waxy fatty acid ester having a weight ratio of (1) to (2) of 3.0: 7.0 to 7.0: 3.0. A hair cosmetic composition containing the waxy fatty acid ester according to claim 1 or 2.