JPH11209230A - Polyhydric alcohol fatty acid ester composition - Google Patents

Abstract

(57) [Summary] [Problem] When a polyhydric alcohol fatty acid ester is produced, the performance of the product tends to fluctuate, and when the performance varies, the product must be provided for an application suitable for the performance of each product. Solve the problem of complexity. SOLUTION: (A) 95 to 99.99% of polyhydric alcohol fatty acid ester of HLB2 to 18 (% by weight, the same applies hereinafter) and (B) a compound having one hydroxyl group and one carboxyl group or a metal salt thereof and carboxyl Ester from a compound having one group or a metal salt thereof.
A polyhydric alcohol fatty acid ester composition characterized by containing 01 to 5% is used.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention belongs to the technical field of producing and using polyhydric alcohol fatty acid ester compositions having HLB of 2 to 18.

[0002]

BACKGROUND OF THE INVENTION Hitherto, polyhydric alcohol fatty acid esters such as sucrose fatty acid esters have been produced and used as surfactants and the like.

[0003] The polyhydric alcohol fatty acid ester produced is designed to have a certain performance by setting the acid value, hydroxyl value and the like within a certain range, but raw materials such as sucrose are made of natural products. In such cases, the performance may vary depending on the raw material source. Further, the performance may vary depending on manufacturing conditions such as variation in heating temperature and pH during synthesis and purification.

When the performance of the produced polyhydric alcohol fatty acid ester varies, the polyhydric alcohol fatty acid ester obtained is used for the purpose corresponding to the performance of the obtained polyhydric alcohol fatty acid utilizing the fact that the required performance differs depending on the use. Therefore, it is necessary to evaluate the performance of each product, store it, and provide it to a use corresponding to each product, which is complicated.

[0005]

According to the present invention, the performance of the product tends to vary when the polyhydric alcohol fatty acid ester is produced as described above, and when the performance varies, the product is suitable for the performance of each product. This is intended to solve the problem of being cumbersome and complicated, and (A) 80 to 99.99% of polyhydric alcohol fatty acid ester of HLB2 to 18 (% by weight, hereinafter the same) and (B) Esters from a compound having one hydroxyl group and one carboxyl group or a metal salt thereof and a compound having one carboxyl group or a metal salt thereof 0.01 to 20
% Of the polyhydric alcohol fatty acid ester composition (Claim 1), wherein the polyhydric alcohol fatty acid ester is an ester of a sugar alcohol and a fatty acid or a lower alcohol ester thereof. (Claim 2), the composition according to claim 1, wherein the polyhydric alcohol fatty acid ester is an ester of sucrose and a fatty acid or a lower alcohol ester thereof, and one hydroxyl group and one carboxyl group. The composition according to claim 1, wherein the ester from the compound having the compound or a metal salt thereof and the compound having one carboxyl group or the metal salt thereof is an ester from lactic acid and a fatty acid.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The polyhydric alcohol fatty acid ester composition of the present invention comprises a polyhydric alcohol fatty acid ester of HLB2-18 (A) as a component (A), one hydroxyl group and carboxyl as a component (B). A composition comprising a compound having one group or a metal salt thereof and an ester (B) from a compound having one carboxyl group or a metal salt thereof.

The polyhydric alcohol fatty acid ester (A) is
An ester comprising a polyhydric alcohol having two or more, preferably three or more hydroxyl groups, and a fatty acid having 8 to 22 carbon atoms, preferably 12 to 18 carbon atoms, or a lower alcohol ester thereof, and is a main component of the composition of the present invention. Is a component used to exhibit properties such as solubilization, emulsification, dispersibility, detergency, and foaming properties.

Since a high molecular weight compound can be used as the polyhydric alcohol, there is no particular upper limit on the number of hydroxyl groups contained. However, when the ester is formed into an ester, it has a structure in which a hydrophilic hydroxyl group remains in the molecule. From the viewpoint of improving the solubility in water or the water retention in oils and fats, those having 2 to 10, more preferably 3 to 8 are preferably used.

When the number of hydroxyl groups contained in the polyhydric alcohol is less than 2, it is not a polyhydric alcohol. In addition, the resulting ester does not show surface activity in aqueous systems,
It becomes oily and insoluble in water. Further, the fatty acid has 8 carbon atoms.
If it is less than 1, the hydrophobic group is too short and the surface activity becomes poor, and those exceeding 22 are difficult to obtain industrially.

Specific examples of the polyhydric alcohol include polyhydric alcohols having two hydroxyl groups such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, and triethylene glycol; glycerin, trimethylolpropane, and triethanolamine. A polyhydric alcohol having three hydroxyl groups,
Polyhydric alcohols having four hydroxyl groups such as pentaerythritol, diglycerin, xylose and sorbitan; polyhydric alcohols having five hydroxyl groups such as xylitol, triglycerin, glucose and fructose; And polysaccharides having more than 6 hydroxyl groups, disaccharides such as sucrose, trehalose and lactose, and trisaccharides such as maltotriose.
These may be used alone or in combination of two or more. Among these, xylitol, sorbitol, trehalose, sucrose, polyglycerin, etc. having five or more hydroxyl groups called so-called sugar alcohols, and particularly sucrose, trehalose, can be used to manufacture products having a wide HLB. It is preferable because it can be done. It is particularly preferable because a product having high hydrophilicity and high HLB can be produced.

Specific examples of the fatty acid include saturated fatty acids such as capric acid, caprylic acid, lauric acid, silistic acid, palmitic acid, stearic acid and behenic acid, oleic acid, linoleic acid, linolenic acid and undecylenic acid. Examples thereof include unsaturated fatty acids and synthetic fatty acids such as isostearic acid. These may be used alone or in combination of two or more. Among them, saturated fatty acids having 8 to 22 carbon atoms are preferable because they have less hue and odor which affect the appearance of the product, and have high commercial value.

Examples of the lower alcohol ester of the fatty acid include esters of the fatty acid with a lower alcohol, for example, a fatty acid alcohol having 1 to 3 carbon atoms such as methyl alcohol.

The hydroxyl value (KOH mg / g) of the polyhydric alcohol fatty acid ester comprising the polyhydric alcohol and fatty acid or lower alcohol ester thereof is 1
It is preferably from 00 to 900 in terms of easy dissolution in water when used, and good performance when used, and more preferably from 200 to 800. Further, the acid value (KOHmg / g) is 10 or less, more preferably 5 or less. Those having an acid value of 5 or less have a high purity and are less likely to affect the performance when used, and are preferred from the viewpoint of quality.

The reason why the acid value increases when an ester is produced using a monovalent fatty acid is that the esterification reaction has not proceeded sufficiently or the amount of the fatty acid used is too large. In this case, since the purity of the product is reduced and the impurities are increased, there is a problem that it is difficult to obtain a desired performance. On the other hand, even if the esterification of the fatty acid proceeds sufficiently, the hydroxyl group can be left by using a polyhydric alcohol having two or more hydroxyl groups. In the case of a polyhydric alcohol having 5 or more hydroxyl groups, an ester having a large hydroxyl value can be formed. In this case, the hydroxyl value is 20
Those having a molecular weight of 0 to 800 have high solubility in water and are preferred from the viewpoint of transparency and emulsifying property, and those having a molecular weight of 200 to 700 are more preferable.

Specific examples of the polyhydric alcohol fatty acid ester (A) of HLB 2-18 include, for example, propylene glycol fatty acid ester, glycerin fatty acid ester,
Sorbitan fatty acid esters, xylitol fatty acid esters, sorbitol fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, trehalose fatty acid esters, and the like. These may be used alone or in combination of two or more. Among them, sugar alcohol fatty acid esters, especially sucrose fatty acid esters such as sucrose caprate, sucrose laurate, sucrose myristate, sucrose palmitate, sucrose stearate, and sucrose oleate Esters and the like are preferred because they have excellent biodegradability and high safety and can be used as emulsifiers in a wide range.

The method for producing the polyhydric alcohol fatty acid ester (A) of HLB 2-18 is not particularly limited, and may be produced according to a conventional method. For example, an esterification reaction between a polyhydric alcohol and a fatty acid, a transesterification reaction between a polyhydric alcohol and beef tallow, cottonseed oil, palm oil, coconut oil and the like, a polyhydric alcohol and a fatty acid lower alcohol (for example, having 1 to 3 carbon atoms such as methyl alcohol) And a transesterification reaction with an (aliphatic alcohol) ester.

The ester (B), which is the component (B) from a compound having one hydroxyl group and one carboxyl group or its metal salt and a compound having one carboxyl group or its metal salt, is a polyhydric alcohol fatty acid ester. But,
Since it is a mixture of a monoester, a diester, a triester and the like, it tends to dissolve or aggregate in an associated micelle form in an aqueous solution, and thus is a component used to improve the solution properties of these.

Specific examples of the compound having one hydroxyl group and one carboxyl group include, for example, lactic acid,
And hydroxyhexanoic acid. These may be used as metal salts such as sodium salts. Of these, lactic acid is generally easily available and is preferred from the viewpoint of safety.

Specific examples of the compound having one carboxyl group include fatty acids, stearic acid, palmitic acid, oleic acid, and the like used in the production of the component (A).
Lauric acid and the like. These may be used as metal salts such as sodium salts.

The ester (B) of the compound having one hydroxyl group and one carboxyl group or the metal salt thereof and the compound having one carboxyl group or the metal salt thereof has an acid value of 10 to 160. The stability of the aqueous solution of the composition of the invention can be improved. Preferred acid values are from 40 to 100. The acid value of the ester (B) can be determined by dissolving the sample in neutral ethanol and determining the free carboxylic acid group by alkali titration with a phenolphthalene indicator.

Specific examples of the ester (B) include, for example, sodium stearoyl lactate, sodium salt of palmitoyl lactate, sodium salt of myristoyl lactate, and sodium salt of lauroyl lactate. These may be used alone or in combination of two or more. Among them, stearoyl lactate and palmitoyl lactate, which are esters of lactate and fatty acid, are preferable from the viewpoint of improving the acid resistance and emulsifying properties of the aqueous solution.

The proportion of the polyhydric alcohol fatty acid ester (A) contained in the composition of the present invention is 80 to 99.99%,
Preferably 95 to 99.99%, more preferably 97
９９99.8%, and the ratio of the ester (B) was 0.01%.
-20%, preferably 0.01-5%, more preferably 0.2-3%. The composition may contain, as other components, unreacted lactic acid, fatty acid and salts thereof in a total amount of 20% or less based on the ester (B). The proportion of the ester (B) is 0.01
%, The stability of the liquid when the composition is dissolved or dispersed in water, especially when the stability in the acidic region is not good, occurs, and the aqueous solution performance of the polyhydric alcohol fatty acid ester of HLB 2 to 18 is deteriorated. It cannot be improved. Further, the ester (B) is a quality improver and is effective in a small amount, and the effect is saturated at 5%.

The composition of the present invention as described above is suitably used for applications such as cosmetic emulsion creams, lotions, treatment creams and conditioning shampoos.

When the composition of the present invention is used for, for example, treatment of an O / W emulsion or cream application, it has a smooth and rich viscosity and leaves a smooth and non-greasy film on the skin. Is required, it has a composition such as sucrose stearic acid ester and stearoyl lactic acid ester Na salt, has a property of improving water solubility by weak acidity, and having uniform emulsion particles and stable emulsification. preferable.

[0025]

EXAMPLES Next, the composition of the present invention will be described based on examples, but the present invention is not limited to these examples.

The evaluation in the examples was performed by the following method.

(Emulsifying property) In order to easily identify the separation state of water in the O / W type emulsion, a predetermined amount (20 g) of polyvalent is added to 400 g of distilled water to which an edible dye (Blue No. 1) is added. After heating and dissolving the alcohol fatty acid ester composition,
30 g / m of soybean white squeezed oil while stirring at 8,000 rpm by K homomixer M type (manufactured by Tokushu Kika Kogyo Co., Ltd.)
in. A predetermined amount (total 266 g) was added dropwise at the speed described above, and further stirred for 5 minutes to completely emulsify the white squeezed oil to prepare an O / W emulsion.

Incidentally, the type of the prepared emulsion is confirmed by a dilution method (an emulsion is uniformly diluted by adding the same liquid as the continuous phase to the emulsion. For example, when one drop of the emulsion is dropped in water, When it is diluted with water and spreads over the entire surface, it is of the O / W type, and when the droplets are standing on the water surface, it is of the W / O type.

On the other hand, the obtained emulsion was transferred to a 100 ml cylinder, left at room temperature for 1 to 7 days, and the volume of distilled water separated was measured. And the O / W emulsion stability of the composition was evaluated.

[0030]

(Equation 1)

The concentration (activator concentration) of the polyhydric alcohol fatty acid ester composition and the single product is expressed in terms of% by weight based on the total amount of water and white squeezed oil.

(Water-soluble) 1.5 g of the polyhydric alcohol fatty acid ester composition was uniformly dispersed in 80 ml of distilled water at room temperature, followed by stirring in hot water at 65 ° C. for 30 minutes, and further adding distilled water while continuing stirring. To 500 ml. This 0.3
After leaving the aqueous solution of the activator at 25 ° C. overnight, water is used as a blank and the turbidity at a wavelength of 720 μm is measured by light transmission (T%) using a spectrophotometer.

(Acid resistance) The pH of the solution prepared for the measurement of the water solubility was adjusted to an acid value of 0.1 using citric acid.
A 15% aqueous solution of the activator was prepared, and the light transmittance (T%) at a wavelength of 720 mμ was measured and evaluated.

Examples 1-9 and Comparative Examples 1-7 Polyhydric alcohol fatty acid ester compositions containing the polyhydric alcohol fatty acid esters (A) and esters (B) shown in Table 1 in the proportions shown in Table 1 were produced. did.

For comparison, six polyhydric alcohol fatty acid esters (A) and esters (B) shown in Table 1 were also prepared.

[0036]

[Table 1]

Using the compositions and single products shown in Table 1, O /
A W-type emulsion was produced, and the water separation rates after 1 day and 7 days were determined. In addition, water solubility and acid resistance were determined. The results are shown in Tables 2 and 3.

[0038]

[Table 2]

[0039]

[Table 3]

[0040]

According to the present invention, a polyhydric alcohol fatty acid ester (A) and a small amount of a compound having one hydroxyl group and one carboxyl group or a metal salt thereof and a compound having one carboxyl group or a metal salt thereof are formed. By using (B), coagulation and separation in acidity when used are improved, and aqueous properties are improved. As a result, even when the performance of the polyhydric alcohol fatty acid ester (A) varies, it can be used for a wide range of applications.

Claims (4)

[Claims] 1. A compound having (A) 80 to 99.99% by weight of a polyhydric alcohol fatty acid ester of HLB2 to 18 and (B) a compound having one hydroxyl group and one carboxyl group or a metal salt thereof and one carboxyl group A polyhydric alcohol fatty acid ester composition comprising 0.01 to 20% by weight of an ester from a compound or a metal salt thereof. 2. The composition according to claim 1, wherein the polyhydric alcohol fatty acid ester is an ester of a sugar alcohol and a fatty acid or a lower alcohol ester thereof. 3. The composition according to claim 1, wherein the polyhydric alcohol fatty acid ester is an ester of sucrose and a fatty acid or a lower alcohol ester thereof. 4. The ester of a compound having one hydroxyl group and one carboxyl group or a metal salt thereof and a compound having one carboxyl group or a metal salt thereof is an ester of lactic acid and a fatty acid. A composition as described.