JP5427033B2 - Detergent composition containing octenyl succinic acid trehalose ester salt composition - Google Patents

Description

  The present invention relates to a detergent composition containing an octenyl succinic acid trehalose ester salt composition, and more specifically, a detergent composition used for applications other than hair washing applications, which is obtained with conventional detergents for skin. The present invention relates to a detergent composition that is not foamed during washing, has a feeling of use, has good water retention after washing, and has a good finish, and is excellent in water retention and skin gloss.

  Conventionally, anionic surfactants and nonionic surfactants have been used in many detergents for the purpose of emulsification, solubilization, washing and the like. Anionic surfactants typified by alkyl sulfates, polyoxyethylene alkyl sulfates, alkyl sulfonates, fatty acid soaps, etc. exhibit good foaming properties, but have poor foam texture and poor sustainability. Because of its strong detergency (degreasing power), there is a drawback that it tends to cause dryness and rough skin after use. Further, the nonionic surfactant has a detergency that the detergency is relaxed and the skin is less likely to dry, but the foaming property is poor, and the skin feels slimy and tight during washing.

  In order to solve the above-described drawbacks, cosmetics and hair washing compositions containing an ester of alkenyl succinic acid and a sugar (excluding trehalose) or a salt thereof have been reported (Patent Documents 1 and 2). These detergent compositions are effective in improving the texture and durability of foam, improving sliminess and squeaking during washing, drying the skin after use, and preventing hair damage.

  However, these detergents contain esters or salts of alkenyl succinic acid and sugar (excluding trehalose) for the purpose of improving the texture and durability of foam and / or the slime and squeakiness during washing. In this case, the blending amount increases, the skin and hair become sticky after washing, and there is a problem in terms of finish. On the other hand, when an ester of alkenyl succinic acid and sugar (excluding trehalose) or a salt thereof is blended for the purpose of preventing the skin and hair after use, the blending amount may be relatively small. In addition, there was a problem in the feeling of use due to insufficient improvement of the texture and durability of the foam and / or the slime and squeak during cleaning. That is, with the conventional technology, it has been difficult to obtain a cleaning composition that achieves both good usability and finished feeling.

  On the other hand, when a composition containing a trehalose ester salt obtained by reacting alkenyl succinic anhydride and trehalose with an alkali catalyst is used as a hair washing detergent composition, it is possible to obtain good foam quality, foam loss, and touch. It is disclosed. (Patent Document 3)

  However, there is no disclosure of a detergent composition that achieves both a good feeling of use and a finished feeling in applications other than hair washing applications.

Japanese Patent No. 3352722 Japanese Patent No. 3794593 Japanese Patent Laid-Open No. 10-279449

  The subject of this invention is providing the cleaning composition (however, except hair-washing use) which was not able to be obtained with the conventional cleaning agent, and made the favorable usability and finish feeling compatible.

  As a result of intensive studies on the above-mentioned problems, the present inventors have formulated an octenyl succinic acid trehalose ester salt composition into a cleaning agent, so that the cleaning has excellent usability and finish in applications other than shampooing applications. It has been found that an agent composition can be obtained, and the present invention has been completed.

  As described above, the detergent composition containing the octenyl succinic acid trehalose ester salt composition according to the present invention has the effects of good foaming and feeling during use and good water retention and finish after washing. . Moreover, when the cleaning composition according to the present invention is used, there is little irritation to the skin and the effect of a highly safe composition is achieved.

First, the octenyl succinic acid trehalose ester salt composition used in the present invention will be described.
Formula (I):

［式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７およびＲ^８は、それぞれ独立して、−Ｈ、一般式（ａ）：

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently —H, general formula (a):

で表される基（式中、Ｍは、−ＨまたはＮａである。）または一般式（ｂ）：

(Wherein, M is —H or Na) or the general formula (b):

で表される基（式中、Ｍは、ＨまたはＮａである。）である。］で表されるオクテニルコハク酸トレハロースエステル塩組成物は、アルカリ触媒の存在下に、一般式（ＩＩ）：

(Wherein, M is H or Na). The octenyl succinic acid trehalose ester salt composition represented by the general formula (II) in the presence of an alkali catalyst:

で表されるトレハロースと一般式（ＩＩＩ）：

Trehalose represented by the general formula (III):

で表されるオクテニルコハク酸無水物を反応させて得ることができる。

It can obtain by making the octenyl succinic anhydride represented by these react.

In the present invention, at least one of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 in} the general formula (I) is a group represented by the general formula (a). Or it is group represented by general formula (b).

  Trehalose (α, α-trehalose), also called mycose or mushroom sugar, is a non-reducing sugar composed of two glucose molecules. In nature, it exists widely in a free state across animals, plants and microorganisms. Recently, an enzyme that directly produces trehalose from starch has been discovered, and high-purity trehalose has been produced on an industrial scale at a low cost. In addition, trehalose has properties required for the above-mentioned cosmetic materials such as water retention and protein denaturation prevention, and those based on trehalose are considered to inherit these properties. In addition, trehalose is a non-reducing sugar, so it is considered to be very stable and little to change with time after the reaction.

  Among octenyl succinic acids that can be used in the present invention, among those classified as alkenyl succinic acids, it is considered that they are most suitable for cosmetic use in terms of their color, odor, reactivity, and foaming properties of the reactants. The amount of octenyl succinic anhydride added when producing the octenyl succinic acid trehalose ester salt composition is preferably 10 to 120% by mass relative to trehalose. When the addition amount is less than 10% by mass, the degree of esterification is too low, and the foaming power may be reduced or the foam may not be modified. Moreover, even if the addition amount exceeds 120% by mass, further improvement in performance cannot be expected, and it is considered that the performance is saturated.

  For the octenyl succinic acid trehalose ester salt composition of the present invention, trehalose is dissolved in an appropriate amount of water alone or in a mixed solvent of water and an organic solvent such as alcohol or acetone, octenyl succinic anhydride is added, and sodium hydroxide is added. Alkali metal hydroxides such as potassium hydroxide and lithium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and lithium carbonate, alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium methoxide , Ammonia, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, butylamine, isobutylamine, secondary butylamine, tertiary butylamine, amyla Mono-, di- or triethanolamine having an alcohol group such as mono-, di- or trialkylamine, triethanolamine, triisopropanolamine, diethanolamine, etc. having an alkyl group such as styrene, secondary amylamine, tertiary amylamine, hexylamine Etc. are added as a catalyst, and it reacts by stirring and mixing, maintaining pH 6 or more, Preferably it is 6-8. Since the pH of the reaction solution is lowered during the reaction, the above alkali catalyst is added as a solid or in the form of a solution in order to maintain the pH. The reaction temperature is not particularly limited, and may be appropriately adjusted to a temperature at which octenyl succinic acid is dissolved in the reaction solution.

  The octenyl succinic acid trehalose ester salt of the present invention is obtained by ring-opening reaction of octenyl succinic anhydride with the above alkali catalyst and ester-bonded to trehalose as a single ester, and the other carboxylic acid is an alkali metal salt with the alkali catalyst used. Or as a solution in the form of an amine salt.

  On the other hand, for the reaction of trehalose and octenyl succinic anhydride, the reaction efficiency is empirically about 40 to 60%, and octenyl succinate in which octenyl succinic anhydride is ring-opened by alkali is produced as a by-product. Depending on the amount of octenyl succinic anhydride to be added, trehalose (that is, octenyl succinic acid is not bound) remains.

  Moreover, the composition ratio is 35-50 mass% of the total of octenyl succinylated trehalose ester salt and trehalose, and the mass ratio of octenyl succinylated trehalose ester salt and trehalose is 3: 1-10: 1. It is preferable that octenyl succinate is 5 to 15% by mass and water is 35 to 60% by mass.

  In addition, the octenyl succinic acid trehalose ester salt composition of the present invention includes an antiseptic and fungicide, various surfactants, oily substances such as long-chain fatty acid esters and hydrocarbons, hydrolyzed proteins, lanolin, lipids, if necessary. , Vitamins, fragrances, pigments, various thickeners, and the like.

  As the cationized polymer used in the present invention, any conventionally known cationized polymer can be used, and in particular, cationized cellulose, cationized guar gum, cationized dextran, and cationized reduced starch syrup are used. Is preferred. Specifically, hydroxyethyl cellulose hydroxypropyl trimethyl ammonium ether (cationized cellulose), chloride-O- [2-hydroxy-3- (trimethylammonio) propyl guar gum (cation) Most preferably, cationized dextran), cationized dextran chloride hydroxypropyltrimethylammonium ether (cationized dextran) and the like are used.

  As the anionic surfactant that can be used in the present invention, any conventionally known anionic surfactant can be used, and in particular, alkyl fatty acid soaps, alkyl sulfates, polyoxyethylene alkyl ether sulfates, alkylbenzenes. It is preferable to use a sulfonate, an α-olefin sulfonate, a polyoxyethylene alkyl ether acetate, a sulfosuccinic acid alkyl disalt, a polyoxyethylene sulfosuccinic acid alkyl disalt, acylmethyl taurine, or the like. As the salt, an alkali metal salt, an alkaline earth metal salt or an alkanolamine salt is preferably used.

  As the amphoteric surfactant that can be used in the present invention, any conventionally known amphoteric surfactant can be used, and in particular, alkyldimethylaminoacetic acid betaine, alkyl fatty acid amidopropyl betaine, 2-alkyl-N. -Carboxymethyl-N'-hydroxyethyl imidazolinium betaine, alkyl fatty acid methyl alanine salt, alkyl hydroxy sulfobetaine, alkyl glycinate or alkyl carboxy glycinate is preferably used alone or in combination.

  As the nonionic surfactant that can be used in the present invention, any conventionally known nonionic surfactant can be used, and in particular, polyoxyethylene alkyl ether, polyoxyethylene hydrogenated castor oil, polyoxyethylene Ethylene alkyl phenyl ether, polyoxyethylene sorbitan fatty acid ester, sorbitan fatty acid ester, alkyl fatty acid diethanolamide or alkyldimethylamine oxide is preferably used alone or in combination.

  As the cationic surfactant that can be used in the present invention, any conventionally known cationic surfactant can be used, and in particular, di-long-chain alkyl quaternary ammonium salts, mono-long-chain alkyl quaternary salts. Ammonium salts, dilong-chain alkyl polyoxyethylene quaternary ammonium salts, mono-long-chain alkyl polyoxyethylene quaternary ammonium salts, and the like are preferably used alone or in combination.

  In addition to the above-mentioned essential components, the cleaning composition of the present invention can be appropriately mixed with components that are usually blended in cosmetics, quasi drugs, and the like as necessary. Examples of components that can be blended in addition to essential components include oils and fats such as squalane, liquid paraffin, petrolatum and other hydrocarbons, olive oil, macadamia nut oil, castor oil and other liquid oils, coconut oil, palm oil, and shea fat Solid fats, waxes such as beeswax, carnauba wax, lanolin, higher alcohols such as stearyl alcohol, behenyl alcohol, isostearyl alcohol, synthetic ester oils such as cetyl octoate, isopropyl palmitate, glyceryl tri-2-ethylhexanoate, dimethylpoly Examples thereof include silicone oils such as siloxane, decamethylcyclopentasiloxane, silicone resin, and amino-modified polysiloxane.

  Other components of the detergent composition include lower alcohols such as ethanol and isopropanol, polyhydric alcohols such as ethylene glycol, glycerin, sorbitol, 1,3-butylene glycol and 1,2-pentanediol, xanthan gum, hydroxyethyl cellulose, Water-soluble polymers such as carboxyvinyl polymer, pH adjusters such as citric acid-sodium citrate and lactic acid-sodium lactate, sequestering agents such as disodium edetate and sodium citrate, other powder components, UV absorbers , Antioxidants, organic amines, preservatives, bactericides, anti-inflammatory agents, astringents, whitening agents, vitamins, amino acids, blood circulation promoters, activators, refreshing agents, various extracts, fragrances, water and the like. However, the present invention is of course not limited to these examples.

  In addition, the dosage form of the cleaning composition in the present invention may be arbitrarily prepared, and has a dosage form tailored to various required physical properties such as a solution system, an emulsion system, a solubilization system, and a dispersion system. Can take. Specific examples thereof include face wash, bar soap, pack, body shampoo, hand soap, cleansing agent, shaving cream and the like.

  EXAMPLES Hereinafter, although an Example demonstrates this invention in more detail, this invention is not limited only to these Examples.

<Production Example 1>
300 g of trehalose (Hayashibara Biochemical Laboratories Co., Ltd .: registered trademark “Treha”) is dissolved in 350 g of water, 180 g of octenyl succinic anhydride is added, and the pH is adjusted with a 20% aqueous solution of sodium hydroxide while stirring at 40 ° C. After adjusting to 7.5-8.0 and reacting for 8 hours, octenyl succinic acid trehalose ester salt composition 1 was obtained. In Composition 1, trehalose octenyl succinate sodium salt was 30.5% by mass, sodium octenyl succinate was 8.0% by mass, trehalose was 11.4% by mass, and water was 50.1% by mass.

<Production Example 2>
300 g of trehalose (Hayashibara Biochemical Laboratories Co., Ltd .: registered trademark “Treha”) is dissolved in 350 g of water, 240 g of octenyl succinic anhydride is added, and the pH is adjusted to 7.5 to 7.5 with triethanolamine while stirring at 40 ° C. The mixture was adjusted to 8.0 and reacted for 8 hours. After the reaction, the octenyl succinic acid trehalose ester salt composition 2 was obtained by adjusting with water so that the solid content was 50%. This composition 2 was 34.7% by mass of trehalose triethanolamine octenyl succinate, 11.7% by mass of triethanolamine octenyl succinate, 3.6% by mass of trehalose, and 50.0% by mass of water.

<Production Example 3>
300 g of trehalose (Hayashibara Biochemical Laboratories Co., Ltd .: registered trademark “Treha”) is dissolved in 350 g of water, 210 g of octenyl succinic anhydride is added, and the pH is adjusted with a 20% aqueous solution of potassium hydroxide while stirring at 40 ° C. After adjusting to 7.5-8.0 and reacting for 8 hours, octenyl succinic acid trehalose ester salt composition 3 was obtained. This composition 3 is composed of 34.1% by mass of trehalose potassium salt of octenyl succinate, 9.3% by mass of potassium octenyl succinate, 7.6% by mass of trehalose, and 49% by mass of water.

<Production Comparative Example 1>
300 g of trehalose (Hayashibara Biochemical Laboratories Co., Ltd .: registered trademark “Treha”) is dissolved in 350 g of water, 150 g of dodecenyl succinic anhydride is added, and the pH is adjusted with a 20% aqueous solution of sodium hydroxide while stirring at 40 ° C. After adjusting to 8.0-8.5 and reacting for 8 hours, it was adjusted with water so that the solid content was 50%, and dodecenyl succinic acid trehalose ester salt composition 4 was obtained. This composition 4 consists of sodium dodecenyl succinate trehalose, sodium dodecenyl succinate, trehalose, and water.

<Production Comparative Example 2>
300 g of trehalose (Hayashibara Biochemical Laboratories Co., Ltd .: registered trademark “Treha”) is dissolved in 350 g of water, 200 g of octadecenyl succinic anhydride is added, and the pH is adjusted with triethanolamine while stirring at 50 ° C. The mixture was adjusted to 8.0 to 8.5 and reacted for 8 hours. After the reaction, it was adjusted with water so that the solid content was 50%, and octadecenyl succinic acid trehalose ester salt composition 5 was obtained. This composition 5 consists of octadecenyl succinic acid trehalose triethanolamine salt, octadecenyl succinic acid triethanolamine, trehalose, and water.

<Change over time>
The octenyl succinic acid trehalose ester salt composition and the alkenyl succinic acid trehalose ester salt composition produced in Production Example and Production Comparative Example were packed in a glass bottle, stored at 50 ° C. for one month, and observed for change. The observation items were examined for color (difference in absorption between 420 nm and 700 nm of the composition) and odor (sensory test) immediately after production and after storage at 50 ° C. for one month. The results are shown in Table 1. In addition, about the sensory test, the strength of the odor was sensorially evaluated by five panelists, and was evaluated in four stages as follows.
+++: The oxidation odor of oil is very strong.
++: Strong oxidation odor of oil.
+: The oxidation odor of oil is slightly strong.
±: There is no oxidized odor of oil, but there is another odor (sweet scent of sugar)-: There is almost no odor.

  From the results in Table 1, the octenyl succinic acid trehalose ester salt composition is more stable over time than other alkenyl trehalose ester salt compositions, and there are few changes in color and odor important for cosmetic quality evaluation. It is suitable as.

<Face-wash form>
A face-washing foam was prepared according to the formulation examples shown in Tables 2 and 3, and 5 panelists with strong skin roughness were used in the same manner as normal use of the samples, and judged by sensory evaluation. The evaluation items were evaluated based on the feeling of use, skin gloss, and water retention. The evaluation criteria were obtained by scoring the feeling of use, skin gloss, and water retention with 5 to 1 points in descending order of effect, and the average score of 5 people was obtained.

In addition, as a comprehensive evaluation, evaluation was performed in four stages as follows.
A: All 3 items are 4 points or more B: 2 of 3 items are 4 points or more C: 1 of 3 items is 4 points or more, or all 3 items are 2 points or more
Less than 4 points X: All 3 items are less than 2 points

  From the results shown in Table 2, the facial cleansing foam to which the octenyl succinic acid trehalose ester salt composition 1 was added was all excellent in feeling of use, skin gloss and water retention. On the other hand, from the results of Table 3, the raw trehalose and dodecenyl succinic acid trehalose ester salt composition 4 were added, or the octenyl succinic acid trehalose ester salt composition 1 was not added, the feeling of use, the gloss of the skin, Not all of the water retention was satisfactory.

<Body shampoo>
Body shampoos were prepared according to the formulation examples shown in Table 4 and Table 5, and 5 panelists with strong skin roughness were used in the same manner as normal use of the samples, and judged by sensory evaluation. Evaluation items and evaluation criteria were the same as for the face-washing foam.

  From the results in Table 4, the body shampoo to which the octenyl succinic acid trehalose ester salt composition 2 is added is excellent in terms of use feeling, skin gloss and water retention. On the other hand, from the results of Table 5, the feeling of use for raw trehalose and octadecenyl succinic acid trehalose ester salt composition 5 or for which octenyl succinic acid trehalose ester salt composition 2 was not added, Not all skin gloss and water retention were satisfactory.

<Cleansing wash>
Cleansing wash was prepared according to the formulation examples shown in Table 6 and Table 7, and 5 panelists were used in the same way as normal use of the sample, and judged by sensory evaluation. Evaluation items and evaluation criteria were performed in accordance with the face-wash form.

  From the results shown in Table 6, the cleansing wash to which the octenyl succinic acid trehalose ester salt composition 3 was added is excellent in terms of use, skin gloss and water retention. On the other hand, from the results in Table 7, the raw trehalose and dodecenyl succinic acid trehalose ester salt composition 4 were added, or the octenyl succinic acid trehalose ester salt composition 3 was not added. Not all of the water retention was satisfactory.

Claims (3)

A cleaning composition containing an octenyl succinic acid trehalose ester salt composition for use other than a hair washing application ,
The octenyl succinic acid trehalose ester salt composition comprises octenyl succinic acid trehalose ester salt, octenyl succinate, trehalose and water, wherein the total of octenyl succinic acid trehalose ester salt and trehalose is 35 to 50% by mass, and octenyl succinate The weight ratio of acid trehalose ester salt to trehalose is 3: 1 to 10: 1, octenyl succinate is 5 to 15% by weight, and water is 35 to 60% by weight.
Cleaning composition .   Further, the composition further comprises a cationized polymer; and one or more surfactants selected from the group consisting of an anionic surfactant, an amphoteric surfactant, a nonionic surfactant, and a cationic surfactant. Item 2. A cleaning composition according to Item 1.   The octenyl succinic acid trehalose ester salt composition is trehalose and octenyl succinic anhydride at pH 7.5 to 8.0 in the presence of an alkaline substance selected from the group consisting of sodium hydroxide, potassium hydroxide and triethanolamine. The cleaning composition according to claim 1, which is obtained by reacting