JP3526456B2 - Esterification product and cosmetic containing the same - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention is an oily raw material which has excellent emollient properties because it has good breathability, does not impede skin respiration, and has a good effect of suppressing water evaporation and water retention. The present invention relates to an esterification product and a cosmetic containing the same.

[0002]

2. Description of the Related Art Oily raw materials are widely used as main raw materials for cosmetics. It is an important component of creams and emulsions, and is used for the purpose of suppressing evaporation of water from the skin and improving the feeling of use. Vegetable oil as the oily raw material,
There are natural oily components such as animal oils, these oils and fats, higher alcohols and higher fatty acids purified and separated from waxes, hydrocarbon oils obtained by fractional purification of petroleum crude oil, and synthetic ester oils. Among them, lanolin obtained by refining oils and fats attached to wool has excellent features not found in other oils and fats, and therefore its usefulness has long been recognized and has been widely used in the field of cosmetics. It was Its main features are that it has good breathability, does not interfere with skin breathing, suppresses evaporation of water from the skin, and is highly water-holding, so it is highly emollient. It is used in various fields such as skin care cosmetics, hair care cosmetics, and makeup cosmetics.

On the other hand, in the recent cosmetics industry, product designs centered on natural and natural products, especially those of plant origin, are popular,
Consumers prefer products that are prescriptively designed using only plant-derived materials. Behind these factors are the fact that animal welfare, which is popular in Europe and the United States, and the recent mad cow problem are major factors. In addition, there are legal restrictions on raw materials derived from beef tallow, and raw materials derived from animals including lanolin are shunned exclusively by the cosmetics industry.

For this reason, alternative raw materials for lanolin have been developed for a long time and are now on the market. For example, diisostearyl malate, (hydroxystearic acid / isostearic acid) dipentaerythyl and the like can be mentioned. These have high hydration ability, which is one of the functions of lanolin, and have a lanolin level, and have good emollient properties, but have poor air permeability as compared with lanolin, and there is a concern that they may interfere with skin respiration. Further, when blended in a cream or the like, there was a problem such that it had a sticky feeling and only a poorly usable product was obtained. In addition, JP-A-3-743
In JP-A-15, it is reported that an esterification product obtained by esterifying a part or all of the hydroxyl groups of glycerin and its condensate with a specific fatty acid is excellent in water retention. However, this product also has inferior air permeability as compared to lanolin, and has problems such as impeding skin respiration, and has not achieved the same performance as lanolin.

[0005]

Therefore, in view of the above circumstances, the present inventor has proposed an esterified product which is excellent in breathability, does not interfere with skin respiration, and has excellent emollient property and usability. The object was to obtain a cosmetic containing

[0006]

As a result, the present inventor has found that an esterification product obtained by esterifying a specific polyglycerin and a specific mixed fatty acid can solve the above-mentioned problems. Has been completed.

That is, the present invention provides an esterification product obtained by esterifying the hydroxyl group of polyglycerol having an average degree of polymerization of 2 to 15 calculated from the hydroxyl value with a mixed fatty acid composed of isostearic acid, erucic acid and ricinoleic acid. The present invention relates to cosmetics containing this.

The present invention will be described in detail below. The average degree of polymerization used in the esterification product of the present invention is from 2 to 15
The average degree of polymerization calculated from the hydroxyl value of the polyglycerin is 2 to 15, preferably 4 to 10.

Further, the constituent fatty acid of the esterification product in the present invention is a mixed fatty acid composed of isostearic acid, erucic acid and ricinoleic acid, and the composition of the mixed fatty acid is 30% by weight or less of isostearic acid, preferably 5 to 20 wt%, erucic acid 20 to 70 wt%, preferably 30 to 60 wt%, ricinoleic acid 20 to 7
0% by weight, preferably 30 to 60% by weight. If the composition is out of the above range, desired performance cannot be obtained in terms of air permeability and emollient property.

The esterification ratio of the mixed fatty acid to the polyglycerin of the esterification product in the present invention is 80 to 1
It is 00% by weight, preferably 90 to 100% by weight. 8
A cosmetic containing an esterification product having an esterification rate of less than 0% by weight has a strong sticky feeling and poor usability.

The method for producing the esterified product in the present invention can be carried out by the following method. A predetermined amount of mixed fatty acid (mixing composition: isostearic acid is 30% by weight) so that the esterification rate of the entire mixed fatty acid is 80 to 100% by weight with respect to the polyglycerol having an average degree of polymerization of 2 to 15 calculated from the hydroxyl value. Hereinafter, 20 to 70% by weight of erucic acid and 20 to 70% by weight of ricinoleic acid are charged. Next, after adding an alkali catalyst such as sodium hydroxide, an esterification reaction is performed according to a conventional method under normal pressure or reduced pressure.

[0012]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.

Example 1 The esterification product was synthesized as follows. Decaglycerin 100 g, isostearic acid 90 g, erucic acid 26
A mixed fatty acid consisting of 8 g and 142 g of ricinoleic acid was placed in a reaction vessel, 0.3 g of sodium hydroxide was added, and then the reaction was performed under a nitrogen stream at 250 ° C. for 4 hours to obtain an esterification rate of 95%. Esterification product 56
0 g was obtained.

Example 2 100 g of hexaglycerin and 49 g of isostearic acid,
A mixed fatty acid consisting of 176 g of erucic acid and 310 g of ricinoleic acid was placed in a reaction vessel and reacted under the same conditions as in Example 1 to give an esterification product 59 having an esterification rate of 98%.
2 g was obtained.

Comparative Example 1 The esterification product was synthesized as follows. Decaglycerin 100 g, isostearic acid 180 g, erucic acid 5
A mixed fatty acid consisting of 4 g and 236 g of ricinoleic acid was placed in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 530 g of an esterification product having an esterification rate of 96%.

Comparative Example 2 A mixed fatty acid consisting of 100 g of decaglycerin, 45 g of isostearic acid, 429 g of erucic acid and 47 g of ricinoleic acid was placed in a reaction vessel and reacted under the same conditions as in Example 1 to obtain an ester having an esterification rate of 98%. 581 g of chemical product
Got

Comparative Example 3 100 g of decaglycerin, 58 g of isostearic acid, 174 g of erucic acid, and 92 g of ricinoleic acid were placed in a reaction vessel and reacted under the same conditions as in Example 1 to obtain an ester having an esterification rate of 64%. 398 g of the chemical product
Got

Comparative Example 4 A reaction was conducted under the same conditions as in Example 1 except that 100 g of glycerin, 185 g of isostearic acid, 553 g of erucic acid, and 292 g of ricinoleic acid were placed in a reaction vessel and the reaction temperature was 210 ° C. , Esterification rate 9
1049 g of 7% esterification product are obtained.

Comparative Example 5 A mixed fatty acid consisting of 100 g of hexaglycerin and 587 g of erucic acid was placed in a reaction vessel and reacted under the same conditions as in Example 1 to obtain an esterified product 6 having an esterification rate of 97%.
36 g were obtained.

Comparative Example 6 100 g of decaglycerin and 135 g of isostearic acid,
A mixed fatty acid consisting of oleic acid (134 g) and myristic acid (144 g) was placed in a reaction vessel and the reaction was carried out under the same conditions as in Example 1 to obtain an esterification product 48 having an esterification rate of 94%.
5 g was obtained.

Air permeability test A bottle containing saturated lime water was capped with a cellophane film, and the esterification products obtained in Examples and Comparative Examples were applied to the cellophane film. It was exposed to carbon dioxide and the time until the saturated lime water became cloudy was measured. The measurement results are shown in Table 1. The esterified products of Examples 1-2 had good air permeability (equivalent to lanolin), but the esterified products of Comparative Examples 1-6 were insufficient in terms of air permeability (worse than lanolin). Met.

[Table 1]

Steam Evaporation Inhibition Test A bottle containing purified water was covered with a cellophane film, and the esterification products obtained in Examples and Comparative Examples were applied to the cellophane film. Then, it was left at 40 ° C. for 20 hours, and the amount of reduction of purified water was measured. The measurement results are shown in Table 2. The esterification products of Examples 1 and 2 were good in suppressing steam evaporation (equivalent to lanolin), but the esterification products of Comparative Examples 1 to 6 were insufficient in terms of suppressing steam evaporation (worse than lanolin). It was a result.

[Table 2]

Water retention test While stirring 1 g of the esterification products obtained in the Examples and Comparative Examples and 9 g of petrolatum, water was gradually added dropwise and allowed to hold until water was released. The amount of water that was retained was shown as a percentage. The measurement results are shown in Table 3. Example 1
The esterification products of ~ 2 had good water retention (equal to or higher than lanolin), but the esterification products of Comparative Examples 1-6 were insufficient in terms of water retention (worse than lanolin). Met.

[Table 3]

Preparation of Cosmetics The esterified products of the above Examples and Comparative Examples were blended,
Various cosmetics were prepared. Formulation Examples 1 to 6 were evaluated, and all had a low oily feeling such as stickiness, a smooth feeling of use, and a good emollient property (moisturizing feeling). On the other hand, compounding comparative examples 1 to 3
Was an insufficient evaluation result in terms of oiliness such as stickiness and emollient (moisturizing). (1) Blending Example 1 Emollient Cream Phase A (wt%) Esterification product of Example 1 3.00 Squalane 7.50 Decaglyceryl monomyristate 2.00 Stearic acid 3.50 Glycerin monostearate 2.00 Glyceryl tri-2ethylhexanoate 5.00 Phase B Glycerin 7.00 10% -potassium hydroxide aqueous solution 1.00 Purified water 69.00 Phase A was dissolved at 80 ° C, and this was heated to 80 ° C B. The phases were gradually added and emulsified. After the emulsification, it was cooled to 35 ° C. to obtain an emollient cream. (2) Formulation Example 2 Milky lotion Phase A (wt%) Esterification product of Example 1 0.50 Decaglyceryl monooleate 1.00 Phase B 1% -Carboxyvinyl polymer 5.00 10% -Hydroxylation Aqueous potassium solution 1.00 1,3-Butylene glycol 5.00 Glycerin 2.00 Purified water 85.50 Phase A was dissolved at 80 ° C, and phase B heated to 80 ° C was gradually added thereto. Emulsified. After the emulsification, it was cooled to 35 ° C. to obtain an emollient cream. (3) Formulation Example 3 Lipstick A phase (wt%) Esterification product of Example 1 15.00 Ceresin 28.50 Castor oil 27.00 Liquid paraffin 15.00 Carnauba wax 7.00 Candelilla wax 5.00 B Phase Titanium oxide 2.00 Red dye 0.50 Phase A is heated at 80 ° C. to uniformly dissolve it, then cooled and uniformly kneaded with a roll mill. Phase B was uniformly dissolved and added to this, and after defoaming, it was poured into a mold and rapidly cooled to obtain a lipstick. (4) Formulation Example 4 Shampoo (wt%) Esterification product of Example 2 2.00 Glycerin 5.00 POE (2) lauryl ether sulfate Sodium (27%) 20.00 POE (2) lauryl ether sulfate Tri Ethanolamine (32%) Polyoxypropylene (36) methyl chloride 35.00 Diethyl ammonium Palm kernel oil Fatty acid diethanolamide (1) 1.00 Sodium chloride 0.50 Citric acid monohydrate 0.20 Purified water 36.30 All components were heated at 80 ° C. to uniformly dissolve them, and cooled to 35 ° C. to obtain shampoo. (5) Formulation Example 5 Hair Conditioner Phase A (wt%) Esterification product of Example 2 3.00 Stearyltrimethylammonium chloride (63%) 0.70 Behenyltrimethylammonium chloride (80%) 0.60 Stearyl alcohol 2.50 Lipophilic glyceryl monostearate 0.50 Phase B Hydroxyethyl cellulose 0.50 Purified water 85.90 Phase A was dissolved at 80 ° C, and phase B heated to 80 ° C was gradually added to this. It was emulsified. After the emulsification, the hair conditioner was obtained by cooling to 35 ° C. (6) Formulation Example 6 Ointment base Phase A (% by weight) Esterification product of Example 1 5.00 Liquid paraffin 18.00 Vaseline 10.00 Cetyl alcohol 10.00 Decaglyceryl monoisostearate 3.00 B Phase Sodium lauryl sulphate 1.00 Purified water 53.00 Phase A was dissolved at 80 ° C, and phase B heated to 80 ° C was gradually added to this to emulsify. After the emulsification, it was cooled to 35 ° C. to obtain an emollient cream. (1) Blending Comparative Example 1 Emollient Cream Phase A (wt%) Esterification product of Comparative Example 1 3.00 Squalane 7.50 Decaglyceryl monomyristate 2.00 Stearic acid 3.50 Glycerin monostearate 2.00 Glyceryl tri-2ethylhexanoate 5.00 Phase B Glycerin 7.00 10% -potassium hydroxide aqueous solution 1.00 Purified water 69.00 Phase A was dissolved at 80 ° C, and this was heated to 80 ° C B. The phases were gradually added and emulsified. After the emulsification, it was cooled to 35 ° C. to obtain an emollient cream. (2) Blending Comparative Example 2 Milky lotion Phase A (wt%) Esterification product of Comparative Example 0.5 0.5 Decaglyceryl monooleate 1.00 Phase B 1% -Carboxyvinyl polymer 5.00 10% -Hydroxylation Aqueous potassium solution 1.00 1,3-Butylene glycol 5.00 Glycerin 2.00 Purified water 85.50 Phase A was dissolved at 80 ° C, and phase B heated to 80 ° C was gradually added thereto. Emulsified. After the emulsification, it was cooled to 35 ° C. to obtain an emollient cream. (3) Blending Comparative Example 3 Hair Conditioner Phase A (wt%) Esterification product of Comparative Example 3 3.00 Stearyl trimethyl ammonium chloride (63%) 0.70 Behenyl trimethyl ammonium chloride (80%) 0.60 Stearyl alcohol 2.50 Lipophilic glyceryl monostearate 0.50 Phase B Hydroxyethyl cellulose 0.50 Purified water 85.90 Phase A was dissolved at 80 ° C, and phase B heated to 80 ° C was gradually added to this. It was emulsified. After the emulsification, the hair conditioner was obtained by cooling to 35 ° C.

[0025]

The esterification product of the present invention is excellent in breathability, does not impede skin respiration, and has excellent emollient property and usability because it has a good effect of suppressing water evaporation and water retention. It is an oily raw material. In addition, the cosmetic containing the esterification product of the present invention has less oily feeling such as stickiness,
It has a smooth feel and has good emollient properties (moisturizing feeling).

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ identification code FI C07C 69/52 C07C 69/52 (56) References JP-A-8-217723 (JP, A) JP-A-8-217725 (JP , A) JP 2001-114731 (JP, A) JP 8-198811 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) A61K 7/00 A61K 7/027 A61K 7 / 06 A61K 7/075 A61K 7/48 C07C 69/52

Claims (2)

(57) [Claims] 1. An average degree of polymerization of 2 to 15 calculated from a hydroxyl value.
Of polyglycerin and the mixed fatty acid composed of isostearic acid, erucic acid, and ricinoleic acid are in the range of 80 to 100% by weight, and the composition of the mixed fatty acid is the following components (1) to (3). Composition of cosmetic esterification product. Component (1) Isostearic acid 30% by weight or less Component (2) Erucic acid 20 to 70% by weight Component (3) Ricinoleic acid 20 to 70% by weight 2. A cosmetic comprising the esterification product according to claim 1.