JP2787469B2 - Hypoallergenic cleaning composition containing an amino acid type surfactant containing two or more carboxyl groups in one molecule - Google Patents

Description

Description: FIELD OF THE INVENTION The present invention relates to a detergent composition which has low irritation and excellent surface activity even under weakly acidic conditions.

[Conventional technology]

Alkyl sulfate (AS), alkyl ether sulfate (AES), α-olefin sulfonate (AOS), and the like have been used as surface active agents for shampoos, body shampoos, and lotions. There is an increasing demand for mild cleansing agents that not only have a natural feel, but also have a undulating effect, have less irritation to the skin and hair, and do not roughen the skin even after continuous use. ing.

As such a mild surfactant, N-acylamino acid type surfactants have been receiving attention.

For example, N-acyl sarcosinate, N-methyl-β-alaninate, which is an acylated product of sarcosine (methyl glycine), N-acyl glutamate, which is an acylated product of glutamic acid, have been used.

[Problems to be solved by the invention]

However, in order to obtain an acylated product of sarcosine, β-alanine or glutamic acid, it is not enough to directly react an acid with these amino acids, and it is sufficient to modify the acid to an acid chloride and then react with the above amino acid. To obtain the required performance, a complicated manufacturing process is required.

Furthermore, N-acyl sarcosinate, N-acyl-N-methyl-β-alaninate and N-acyl glutamate are mildly irritating, but under mildly acidic conditions close to the pH of human skin, they cause white precipitation and surface activity. Is reduced.

[Means to solve the problem]

The present inventors have found that the action on the skin and hair is not restricted at all in mild use without lowering the surface activity even in the weak acidification as described above, and the interface is easy to produce and economically excellent. As a result of intensive research on activators,
Alkenyl or alkyl succinic anhydrides and glycines,
Alternatively, they have found that a reaction product with an alanine or glutamic acid and a salt thereof have stable and excellent surface activity even under a weak acidity, and have completed the present invention.

In the present invention, the following general formula (Wherein R represents an alkenyl or alkyl group having 8 to 30 carbon atoms, R ′ represents a hydrogen or methyl group, and M represents a hydrogen or a base, respectively). (A), (B), (B) The present invention provides a low-irritant detergent containing at least one surfactant selected from the group consisting of C).

The surfactants (A), (B) and (C) of the present invention are produced, for example, by the following reaction.

(Wherein R is the same as described above) The surfactant represented by (A) is obtained by reacting an alkenyl or alkyl succinic anhydride with a glycine, and the surfactant represented by (B) is: The surfactant represented by (C) obtained by reacting an alkenyl or alkyl succinic anhydride with β-alanine can be produced by reacting an alkenyl or alkyl succinic anhydride with glutamic acid. The alkenyl or alkyl succinic anhydride which is a raw material common to (A), (B) and (C) is α-
It can be obtained by a known method in which an olefin and maleic anhydride are ene-reacted in an inert gas. When dodecene is used as the α-olefin, dodecenylsuccinic anhydride is obtained, and when octadecene is used, octadecenylsuccinic anhydride is obtained. In these compounds, R may be an alkenyl group having 8 to 30 carbon atoms, and among them, 12 to 16 is preferable. Further, by using an alkyl succinic anhydride obtained by hydrogenating the above alkenyl succinic anhydride by a known method, hue, odor and the like can be improved.

R 'can be hydrogen or a methyl group, and among them, a methyl group is preferable. (A), (B) and (C) can be easily obtained by reacting an acid anhydride with an amino group. One embodiment of the production method is as follows.

In the method (A), alkenyl succinic anhydride and sarcosine can also be reacted by batch charging. However, a preferred method is to disperse sarcosine in a solvent, heat the dispersion to 70 to 120 ° C., and add alkenyl succinic acid to the dispersion. It is obtained by dropping an anhydride or conversely dissolving alkenyl succinic anhydride in a solvent, heating to 70 to 120 ° C. and dropping sarcosine to react.

As a solvent used in this reaction, an lipophilic solvent such as an aliphatic or aromatic solvent has a poor affinity for the reaction product, so that esters, ketones, glycol ethers, cyclic ethers, glycol diethers and the like are used. Hydrophilic solvents are preferred, and alkylene glycol dialkyl ethers having no polar group are particularly preferred. After the reaction, it can be produced by removing the solvent by drying under reduced pressure or the like.

Each of the reactants is easily soluble in water, is neutralized by a known base, or an aqueous solution thereof, and is led to each salt.
Examples of the base used include inorganic bases such as potassium hydroxide, sodium hydroxide, calciur hydroxide, and ammonia; lower alkylamines such as monoalkylamine, dialkylamine, and trialkylamine; and monoethanolamine, diethanolamine, and triethanolamine. Among them, alkanolamines such as triethanolamine are preferable.

The cleaning composition of the present invention may contain only one of the surfactants represented by (A), (B) and (C),
Also, two or more kinds may be included in combination.

[Action]

Since the surfactant of the present invention has an amino acid skeleton, it has little action on mucous membranes and skin, has mild action on hair, and has a hair protection effect.

Furthermore, since it is a dibasic acid or a tribasic acid, one or two or more free carboxyl groups can be added as a monopotassium salt or a monoethanolamine salt.
It has excellent surface activity even under weak acidity.

〔effect〕

The surfactants (A), (B) and (C) of the present invention and the salts thereof have low irritation and excellent surfactant activity even under weakly acidic conditions, and have a mild effect on skin and mucous membranes. It also has a protective effect on hair.

Therefore, it is suitably used for applications such as shampoos, body shampoos, hair and skin cleaners for infants, and kitchen cleaners for housewives whose hands are easily roughened.

[Test Example 1] Foaming Power The foaming power of a mono / triethanolamine aqueous solution of the surfactant of the present invention was evaluated. All aqueous solutions are pH
= 6.5, and the solid content was adjusted to 40%.

The evaluation of the foaming power was carried out at a concentration of 0.25% (in terms of solid content) using the Ross Miles method.

 The results are shown in Table 1.

(Test Example 2) Shampoo (Formulation) Compound of Example 15 parts Lauryl imidazolinium betaine 3 coconut fatty acid diethanolamide 4 cationized cellulose 2.0 water balance 100 (Evaluation) (i) Foaming test 0.25% concentration (solid type) ): Good (200 ml or more) △: normal (150 to 200 ml or more) ×: poor (ii) Detergency test A reaction rate of 30 to 30 prepared according to the provisional standards of the Oil and Fats Chemistry Association. 40%
Was measured with a Terg-O-Tometer, and the cleaning effect was calculated by the following equation.

Good cleaning efficiency 80% or more △ Normal cleaning efficiency 60-80% or more × poor cleaning efficiency 60% or less (iii) Skin irritation Perform a hand immersion test with 10 panelists and after the test The skin condition was visually observed.

(Conditions) Specimen: 5% cleaning solution composition (35 ° C) Immersion: Twice a day for 20 minutes for 2 days (Evaluation)…: Good soldering rough 2 or less △: Normal 〃 3 to 6 ×: Poor Table 7 shows the results.

The compounds of Examples and Comparative Examples are the same as those in Table 1 in the evaluation of foaming power [Test Example 3] Body shampoo (formulation) Compound of the present invention 20 parts Lauryl ether sulfate sodium (EO 3 mol) 11 Coconut fatty acid diethanolamide 4.5 Water balance Amount 100 In the same manner as in Test Example 2, the body shampoo of the above formulation was evaluated for foaming power and detergency skin irritation. The results are shown in Table-3.

Claims (1)

(57) [Claims] 1. An amino acid type interface containing two or more carboxyl groups in one molecule derived from an alkenyl or alkyl succinic anhydride represented by the following general formulas (A), (B) and (C): At least one compound selected from the group of activities
Hypoallergenic cleaning composition comprising at least one species (Wherein R represents an alkenyl or alkyl group having 8 to 30 carbon atoms, R ′ represents a hydrogen or methyl group, and M represents a hydrogen or a base, respectively)