JP3475047B2 - Emulsifier composition and aqueous solution containing emulsifier - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an emulsifier composition and an emulsifier-containing aqueous solution, and more particularly to an emulsifier composition containing a diglycerin fatty acid ester,
The present invention relates to an emulsifier composition and an emulsifier-containing aqueous solution that do not cause precipitation even under acidic or neutral conditions and can stably disperse a diglycerin fatty acid ester.

[0002]

2. Description of the Related Art Diglycerin fatty acid ester has an HLB of 6 to 10 by changing the ratio of diglycerin to fatty acid and the type of fatty acid, and as an emulsifier that can be used for O / W emulsification and the like, especially for food applications. Widely expected to be applied to.

By the way, the diglycerin fatty acid ester has a low solubility in water, and even a pure monoester product causes turbidity in the solution when added at a low concentration of about 100 ppm and precipitates over time. Therefore, in order to uniformly disperse the product in the food and prevent product unevenness, it is necessary to sufficiently preliminarily stir the product during use to ensure the dispersion.

However, some foods may not be suitable for long-term stirring, and naturally there are restrictions on the types of foods that can be used and the concentration of emulsifiers used. Further, the dispersibility of diglycerin fatty acid ester is further lowered depending on conditions such as acidic pH and salt concentration. Therefore, when diglycerin is used in a beverage, a pH adjusting operation is indispensable.
That is, it has been considered difficult to use the diglycerin fatty acid ester in foods in acidic or neutral regions where uniform appearance and transparency are required.

[0005]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object thereof is to contain a diglycerin fatty acid ester, excellent dispersibility, and pH 3.5 to 7.
Another object of the present invention is to provide an emulsifier composition that can be used for the acidic to neutral range beverages. Another object of the present invention is to provide various aqueous solution products using the above emulsifier composition.

[0006]

Means for Solving the Problems As a result of intensive studies, the present inventor has mixed a specific polyglycerin fatty acid ester and / or a specific sucrose fatty acid ester with a specific ratio with respect to the diglycerin fatty acid ester. It was found that the emulsifier composition can be dispersed in an aqueous solution without causing precipitation.

The present invention has been completed based on the above findings. A first gist of the present invention is to contain the following A component and B component and / or C component, and Alternatively, the emulsifier composition is characterized in that the weight ratio of the component C is 0.1 to 100.

A. Diglycerin fatty acid ester whose constituent fatty acid is a saturated or unsaturated fatty acid having 10 to 24 carbon atoms B. Polyglycerin fatty acid ester C. consisting of a partial ester of a saturated fatty acid having 10 to 14 carbon atoms and polyglycerin having an average degree of polymerization of 4 or more. Sucrose fatty acid ester whose constituent fatty acid is a saturated fatty acid having 10 to 14 carbon atoms

A second aspect of the present invention resides in an emulsifier-containing aqueous solution containing the above emulsifier composition and containing the component A in an amount of 2% by weight or less.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
In the present invention, the following A component and B component and / or C component are used.

Component A has 10 to 24 carbon atoms as constituent fatty acids.
It is composed of diglycerin fatty acid ester which is a saturated or unsaturated fatty acid. Particularly, a diglycerin fatty acid ester having a monoester content of 50% by weight or more in all the esters is preferable.

Specific examples of the above constituent fatty acids include:
Examples thereof include capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, erucic acid and behenic acid. On the other hand, as diglycerin, a purified product recovered from a distillation residue of glycerin or the like is usually used.

The diglycerin fatty acid ester is obtained by an esterification reaction of the above fatty acids alone or a mixed fatty acid of two or more kinds with diglycerin, or an ester exchange reaction between the lower alcohol ester of the above fatty acids and diglycerin. . The reactions of esterification and transesterification are
Usually, it is carried out by using an alkali catalyst and heating at 150 to 260 ° C. Although it depends on the reaction conditions, the reaction product usually contains polyesters such as di and tri in addition to the monoester.

As a means for increasing the monoester content in the diglycerin fatty acid ester, various fractionation methods such as various chromatography using an organic solvent and a countercurrent distribution device can be used, but the molecular distillation method is used. Most efficient.

The monoester content of diglycerin fatty acid ester can be analyzed by using an organic solvent-based GPC column and RI as a detector. Eluent is TH
An example of the analysis conditions in the case of F (tetrahydrofuran) is as shown in Table 1 below.

[0016]

[Table 1] Device: LC-6A (Shimadzu) Column: TSKgel G2500HXL x 2 (7.8mm ID x 30cm) + TSK
Guard column (6.0mmID × 4.0cm) Temperature: 40 ℃ Eluent: THF 0.5ml / min Detector: RI Injection volume: 100μl

In the above analysis, the sample was prepared by dissolving it in THF so as to have a concentration of about 0.1% by weight, and the quantitative determination was performed by using the area fraction of each peak as the content (% by weight) of each ester.

Component B is a polyglycerin fatty acid ester, which is a partial ester of a saturated fatty acid having 10 to 14 carbon atoms and polyglycerin having an average degree of polymerization of 4 or more. In particular, polyglycerin fatty acid ester having a fatty acid introduction ratio of 15 to 30 mol% with respect to the total hydroxyl groups of polyglycerin is preferable.

Average degree of polymerization of polyglycerol (degree of condensation)
Is not particularly limited as long as it is 4 or more, but a range of 6 to 12 is preferable from the viewpoint of sufficiently enhancing the hydrophilicity of the ester. When the average degree of polymerization is less than 4, the effect of dispersing the component A diglycerin fatty acid ester cannot be expected.

If the fatty acid introduction rate exceeds 30%, the hydrophobicity of the polyglycerin fatty acid ester becomes strong, and the dispersion effect on the diglycerin fatty acid ester tends to decrease. On the other hand, if it is less than 15%, it is difficult to produce the polyglycerin fatty acid ester itself, and since it contains a large amount of free polyglycerin, the concentration of the active agent component is low, and a high concentration is required to reduce the free polyglycerin. There is a disadvantage in manufacturing cost.

The fatty acid introduction rate of the polyglycerin fatty acid ester can be measured by the following method with respect to the pure ester content excluding the free polyglycerin.

First, a hydroxyl value, a saponification value, and an acid value of an emulsified emulsifier containing free polyglycerin are measured by a standard method (standard oil and fat analysis test method: established by Japan Oil Chemistry Association).

Next, for example, a reversed phase packing material column is used to retain the polyglycerin fatty acid ester and allow the free polyglycerin to pass therethrough, and the both are completely separated, followed by gel permeation mode and low polyglycerin. Separate from molecular impurities. By such a method, the exact absolute amount of free polyglycerin can be determined without pretreatment. Then, the portion derived from free polyglycerin is subtracted from the hydroxyl value measured above, and the saponification value and acid value are combined to calculate the fatty acid introduction rate of the total hydroxyl groups in the esterified polyglycerin molecule.

The reaction method of fatty acid and polyglycerin is
There is no particular limitation, and polyglycerin and the fatty acid raw material may be reacted at a predetermined molar ratio so that a predetermined fatty acid introduction rate is achieved. The reaction is usually carried out in the presence of an alkali catalyst at 130
It is performed at a high temperature of ℃ or more. The obtained polyglycerin fatty acid ester can be used as it is.

When the amount of polyglycerin fatty acid ester added to an aqueous product is limited, the total amount of emulsifiers added can be reduced by separating and purifying unreacted free polyglycerin. I can. Examples of the separation / purification method include liquid-liquid extraction with an organic solvent / salt aqueous solution or a nonpolar organic solvent / polar organic solvent, and chromatography using a hydrophilic or hydrophobic carrier.

Component C is composed of constituent fatty acids having 10 to 14 carbon atoms.
It consists of sucrose fatty acid ester, which is a saturated fatty acid of. Particularly, sucrose fatty acid ester having a monoester content of 70% or more is preferable. When the monoester content is less than 70%, the hydrophilicity of the sucrose fatty acid ester becomes insufficient, and the dispersion effect on the diglycerin ester tends to decrease. The content of monoester can be determined by the same method as for the diglycerin fatty acid ester.

Specific examples of the saturated fatty acids having 10 to 14 carbon atoms which are the constituent fatty acids of the component B polyglycerin fatty acid ester and the component C sucrose fatty acid ester include capric acid, lauric acid and myristic acid. ,
Lauric acid is particularly preferable. Two or more kinds of these constituent fatty acids may be used in combination.

The emulsifier composition of the present invention comprises the above components A and B and / or C, and
The weight ratio of component B and / or component C to component A must be 0.1-100. In such a composition range, the emulsifier composition of the present invention exhibits a good dispersed state when made into an aqueous solution. The preferred range of the above weight ratio is 1-10.

The emulsifier composition of the present invention is obtained by mixing the components in a predetermined ratio, and the mixing method may be powder mixing or melt mixing. The emulsifier composition may take the form of a powder, a paste dissolved in water, or an emulsion. It is also possible to separately prepare an aqueous dispersion solution of each component and add it to the aqueous product.

The emulsifier-containing aqueous solution of the present invention contains the above emulsifier composition, and the content of the component A must be 2% by weight or less. When the content (concentration) of the diglycerin ester of the component A exceeds 2% by weight, it becomes difficult to maintain a stable dispersed state depending on the liquid to which the emulsifier-containing aqueous solution of the present invention is applied.

The pH range of the emulsifier-containing aqueous solution is not particularly limited, but a pH range of 3.5 to 7 is preferable. If the pH exceeds 7, the effect of the emulsifier will not continue due to the hydrolysis of the ester bond of the emulsifier component over time, and
When is less than 3.5, sufficient dispersion tends to be difficult.

The acid used for adjusting the pH is not particularly limited, but inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, acetic acid, citric acid, succinic acid, malic acid, tartaric acid, fumaric acid, maleic acid, Examples thereof include organic acids such as lactic acid.

The emulsifier-containing aqueous solution of the present invention may contain an inorganic salt. The inorganic salt is not particularly limited, but examples thereof include neutral salts such as sodium chloride, potassium chloride, sodium sulfate, potassium sulfate. The salt concentration is
Although not particularly limited, it is preferably 0.1 M or less. If the salt concentration exceeds 0.1 M, it tends to be difficult to obtain a stable dispersed state.

Examples of applications to foods in which the emulsifier-containing aqueous solution of the present invention is preferably used include, for example, transparency such as grain-based beverages such as black coffee, straight black tea, lemon tea, oolong tea, green tea, and barley tea. Beverages including high-quality beverages, milk coffee, milk tea, cocoa, etc., or side dishes and canned foods subjected to retort sterilization treatment are included.

In each of the above-mentioned application examples, the method of adding the emulsifier composition is not particularly limited, but usually, the diglycerin fatty acid ester as the component A and the polyglycerin fatty acid ester as the component B and / or the sucrose fatty acid ester as the component C are used. A method is employed in which and are separately prepared as an aqueous dispersion solution and then added to an aqueous product at a predetermined ratio, or a premixed emulsifier composition is dissolved in water and added.

[0036]

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded. The samples shown in Table 2 were used in the following examples.

[0037]

[Table 2]

Examples 1 to 5 and Comparative Examples 1 to 2 The above diglycerin fatty acid ester, polyglycerin fatty acid ester and sucrose fatty acid ester were added to demineralized water, heated and dissolved at 80 ° C. for 20 minutes, and then allowed to cool. A 1% by weight homogeneous aqueous solution was prepared. These were mixed in the ratios shown in Table 3, and an aqueous solution of citric acid, a saline solution and demineralized water were added thereto so that a predetermined concentration was obtained to prepare 10 mL of an emulsifier-containing aqueous solution.
The obtained aqueous solutions were stored at 25 ° C. for 7 days, and then the liquid properties were visually compared. The results are shown in Table 3.

[0039]

[Table 3]

The significance of the visual evaluation symbols in Table 3 is shown in Table 4 below.
As shown in.

[Table 4] ◎: Transparent uniform state ○: Uniformly dispersed state without precipitation Δ: A state in which slight precipitation occurred ×: A large amount of precipitate

[0041]

INDUSTRIAL APPLICABILITY The emulsifier composition of the present invention can be used in an acidic or neutral solution in which diglycerin fatty acid ester is conventionally unusable. As a result, according to the present invention, it became possible to add the diglycerin fatty acid ester to a wide range of beverages that require transparency and dispersion stability.

According to the present invention, not only foods but also
The possibility of using diglycerin fatty acid ester in other fields can be expanded. That is, since the emulsifier composition of the present invention can maintain a stable dispersed state in an acidic region, it can be widely applied to industrial fields in addition to the purpose of emulsifying foods.

─────────────────────────────────────────────────── ─── Continuation of front page (58) Fields investigated (Int.Cl. ⁷ , DB name) A23L 1/035 A23L 2/00-2/62 B01F 17/44-17/56 JSTPlus (JOIS)

Claims (7)

(57) [Claims] 1. The following A component and B component and / or C
An emulsifier composition comprising a component and a weight ratio of the component B and / or the component C to the component A is 0.1 to 100. A. Diglycerin fatty acid ester whose constituent fatty acid is a saturated or unsaturated fatty acid having 10 to 24 carbon atoms B. Polyglycerin fatty acid ester C. consisting of a partial ester of a saturated fatty acid having 10 to 14 carbon atoms and polyglycerin having an average degree of polymerization of 4 or more. Sucrose fatty acid ester whose constituent fatty acid is a saturated fatty acid having 10 to 14 carbon atoms 2. The composition according to claim 1, wherein the monoester content of the diglycerin fatty acid ester as the component A is 50% by weight or more. 3. The composition according to claim 1, wherein the introduction rate of the fatty acid of the polyglycerin fatty acid ester as the component B is 15 to 30 mol% with respect to the total hydroxyl groups of the polyglycerin. 4. The composition according to claim 1, wherein the monoester content of the sucrose fatty acid ester as the C component is 70% by weight or more. 5. An emulsifier-containing aqueous solution containing the emulsifier composition according to claim 1, wherein the content of the component A is 2% by weight or less. 6. The aqueous solution according to claim 5, wherein the pH of the solution is 3.5 to 7. 7. The aqueous solution according to claim 5, which contains 0.1 M or less of a neutral inorganic salt.