JPH037799A - Low-irritant detergent composition containing amino acid-type surfactant having in one molecule two or more carboxyl groups - Google Patents

Abstract

PURPOSE:To provide the title composition having high surface-active ability even under weakly acidic conditions, containing specific amino acid-type surfactant(s) containing plural carboxyl groups. CONSTITUTION:The objective composition containing at least one amino acid- type surfactant having in one molecule two or more carboxyl groups derived from an alkenyl(or alkyl)succinic anhydride, selected from those of respective formulas I-IV (R is 8-30C alkenyl or alkyl; R' is H or methyl: M is H or Cl). The present composition is suitable as a shampoo, body shampoo, detergent for the hair and skin of infants, kitchen detergent for housewives with the hands liable to be chapped, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a detergent composition that is hypoallergenic and has excellent surfactant ability even under weak acidity.

[Conventional technology]

Conventionally, alkyl sulfates (AS), alkyl ether sulfates (AES), α-olefin sulfonates (AO5), etc. have been used as surfactant base materials for shampoos, body shampoos, lotions, etc., but recently, foaming and cleaning properties have been used. Not only is it attractive, but it also has a natural texture, a lightening effect, and is less irritating to the skin and hair.
There is an increasing demand for mild detergents that do not irritate the skin or damage the hair even when used repeatedly.

N-acylamino acid type surfactants have been attracting attention as such hypoallergenic surfactants.

For example, N-acyl sarcosinate, which is an acylated product of sarcosine (methylglycine), N-methyl β-alaninate, N-acylglutamate, which is an acylated product of glutamic acid, and the like have come to be used.

[Problem that the invention seeks to solve]

However, in order to obtain acylated products of sarcosine, β-alanine, or glutamic acid, it is insufficient to directly react acids with these amino acids, and it is sufficient to modify the acids into acid chlorides and then react with the above amino acids. In order to achieve the desired performance, a complex manufacturing process is required.

Furthermore, N-acylsarcosinate, N-acyl-Nmethyl-β-alaninate, and N-acylgutaminate are hypoallergenic, but under weak acidic conditions close to the pH of human skin, they may cause scuttling or lose their surfactant ability. It has the disadvantage that it decreases.

[Means for solving problems]

The present inventors have developed a surfactant that has a mild effect on the skin and hair without reducing its surface activity even under weak acidification as described above, does not impose any restrictions on its use, is easy to manufacture, and is economically superior. As a result of extensive research into agents, we have found that the reaction products of alkenyl or alkyl succinic anhydrides with glycine, alanine, or glutamic acid, and their salts, are stable even under weak acidity and have excellent surfactant properties. They discovered this and completed the present invention.

Already, the present invention is based on the following general formula () % formula % () (wherein R is an alkenyl group or an alkyl group having 8 to 30 carbon atoms, R'' is hydrogen or a methyl group, and M is hydrogen or a base, respectively. ) The present invention provides a hypoallergenic detergent containing at least one surfactant selected from the group consisting of surfactants (A), (B), and (C).

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

(A) (C) CHCOOH R CHCOOH CH.

I R-CHC-N-GOOH CH, C0OH CHCOOH CH.

and/or and/or CH, COOM CH, COOM (C) Methylalanine glutamic acid 7- CHCOOH Base 08000M (In the formula, R and H are the same as above) The surfactant represented by (A) is alkenyl or alkyl Obtained by the reaction of succinic anhydride and glycine,
The surfactant represented by (B) is obtained by the reaction of alkenyl or alkyl succinic anhydride with β-alanine, and the surfactant represented by (C) is obtained by the reaction of alkenyl or alkyl succinic anhydride with glutamic acid. It can be produced by reacting with

Alkenyl or alkyl succinic anhydride, which is a common raw material for (A), (B), and (C), can be obtained by a known method of reacting α-olefin and maleic anhydride with ene 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 can be an alkenyl group having 8 to 3 carbon atoms, with 12 to 16 carbon atoms being preferred.

Further, R' can be hydrogen or a methyl group, with a methyl group being particularly preferred. (A), (B), and (C) can all be easily obtained by reacting an acid anhydride with an amino group, and one embodiment of the production method is as follows.

In (A), for example, sarcosine is dispersed in a solvent such as diethylene glycol dimethyl ether, and 70 to 12
The reaction is carried out by heating to 0° C. and adding alkenylsuccinic anhydride.

It can be produced by removing the solvent after the reaction by drying under reduced pressure or the like.

All of the reactants are easily soluble in water, neutralized with a known base or an aqueous solution thereof, and led to their respective salts. The bases used include inorganic bases such as potassium hydroxide, sodium hydroxide, calciyl hydroxide, and ammonia; lower alkyl amines such as monoalkylamines, dialkylamines, and trialkylamines; and monoethanolamine, jetanolamine, and triethanolamine. Examples include alkanolamines such as ethanolamine, among which alkanolamines such as triethanolamine are preferred.

The cleaning composition of the present invention may contain only one type of surfactant represented by (A), (B), or (C), or
A combination of two or more types may be included.

[Effect]

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

Furthermore, since it is a dibasic acid or tribasic acid, it has one or two free carboxyl groups even when used as a monosalt such as monopotassium salt or monoethanolamine salt, and is excellent even under weak acidity. Demonstrates surface active ability.

〔effect〕

Furthermore, the surfactants (A), (B), and (C) of the present invention are hypoallergenic and have excellent surfactant properties even under mildly acidic conditions, and have mild effects on the skin and mucous membranes. It also has a protective effect on hair.

Therefore, it is suitably used for shampoos, body shampoos, hair and skin cleansers for infants, kitchen cleaners for housewives who tend to get rough hands, and the like.

[Test Example 1] Foaming Power The foaming power of a mono-triethanolamine salt aqueous solution of the surfactant of the present invention was evaluated. Both aqueous solutions have p
] (= 6, 5, adjusted to have a solid content of 40%.

The foaming power was evaluated using the Ross Miles method at a concentration of 0.25% (calculated as solid content).

The results are shown in Table-1.

Note 2 The structural formulas of *1 to *6 in the table are shown on page 14.

(Test Example 2) Shampoo (Formulation) Compound of Example 15 parts Lauryl imidazolinium betaine 3 Coconut fatty acid diethanolamide 4 Cationized cellulose
2.0 Water Remaining 00 (Evaluation) (i) Foaming power test Evaluated by Ross Miles method at a concentration of 0.25% (solid content) ○... Good (200 mQ or more) △...・Normal (150-200 mQ or more)
% of the contaminated cloth was used to measure the reflectance after cleaning with a Terg-OTometer, and the cleaning effect was calculated using the following formula.

O...Good Cleaning efficiency 80% or more △...Normal Cleaning efficiency 60-80% or more ×...Poor
Cleaning efficiency 60% or less (River) Skin irritation A manual immersion test was conducted by a panel of 10 people, and the condition of the skin was visually observed after the test.

(Conditions) Sample: Cleaning liquid composition 5% (35°C) Immersion = 20 minutes twice a day Conducted for 2 days (Evaluation) ○... Good Roughness 2 people or less △...
・Normal 3-6 people×・・・Poor
The results of the seven participants are shown in Table 2.

2-Shampoo and "Table Body Shampoo Composition Evaluation Results Compounds of Examples and Comparative Examples are the same as Table 1 for Foaming Power Evaluation [Test Example 3] Body Shampoo (Formulation) Compound of the Invention 20 parts lauryl ether full Phate sodium (E O3 mol) 1
1 Coconut fatty acid jetanolamide 4.5 Water
Remaining amount: 00 Similarly to Test Example 3, the body shampoo with the above formulation was evaluated for foaming power, cleansing power, and skin irritation.

The results are shown in Table-3.

Comparative example 4 coconut fatty acid cloth ken

Claims (1)

[Scope of Claims] Amino acid type containing two or more carboxyl groups in one molecule derived from alkenyl or alkyl succinic anhydrides represented by the following general formulas (A), (B), and (C) A hypoallergenic cleaning composition (A) characterized by containing at least one compound selected from the group of surfactants ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ and/or ▲ Mathematical formulas, chemical formulas, tables, etc. ▼ (B) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and/or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (C) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and/or ▲ Mathematical formulas, chemical formulas, There are tables, etc.▼ (In the formula, R represents an alkenyl group or alkyl group having 8 to 30 carbon atoms, R' represents hydrogen or a methyl group, and M represents hydrogen or a base, respectively.)