JPH0226672B2 - - Google Patents

Description

[Detailed description of the invention]

(Field of Industrial Application) The present invention relates to a detergent composition that satisfies the essential requirements for a detergent, such as foaming properties and cleansing properties, and has extremely low irritation to the skin. (Prior art) Conventionally, with surfactants and surfactant compositions that have a strong protein denaturing power, severe roughness has been observed when used repeatedly, whereas surfactants and surfactant compositions that have a low protein denaturing power have been used for a long time. It is well known that the composition (for example, shampoo) hardly causes skin disorders such as rough hands even when used for a long period of time, and has extremely low irritation to the skin. On the other hand, higher fatty acid amide sulfonate represented by the general formula (A) below is used in cleansing agents such as facial cleansers and shampoos due to its excellent cleaning power, but it also has protein denaturing power and skin irritation. It has the disadvantage of being highly sensitive and prone to skin problems such as rough hands. Against this background and with the advancement of living standards, there is a strong demand for the development of low skin irritation surfactants and detergent compositions that are highly safe for the human body. is the current situation. (Problems to be Solved by the Invention) As a result of intensive research aimed at improving the drawbacks of the above-mentioned prior art, the present inventors have previously filed an application (Patent Application No.
No. 59-216532, Japanese Patent Application No. 60-213155), surfactant N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester salt represented by general formula (B) below. When an appropriate amount is mixed with the higher fatty acid amide sulfonate represented by the general formula (A) below, it satisfies the essential requirements as a detergent such as foaming properties and detergency, while having a low protein denaturing power. The present inventors have discovered that it is possible to obtain a detergent composition that hardly causes skin disorders such as rough hands and has extremely low skin irritation, and has completed the present invention. An object of the present invention is to provide a detergent composition that satisfies essential requirements for a detergent such as foaming properties and cleansing properties, and has extremely low irritation to the skin. (Means for solving the problem) The above purpose is as follows: General formula (A) (In the above formula, R ₁ is a caprylic, lauryl, myristyl, palmityl, stearyl, isostearyl, or oleyl group, and M ₁ is sodium, potassium, ammonium, or triethanolammonium.) Fatty acid amide sulfonate and general formula (B) (In the above formula, R ₂ is a caprylic group, a lauryl group,
myristyl, palmityl, stearyl or oleyl group, _M2 is sodium, potassium, ammonium or triethanolammonium. This is achieved by a mild detergent composition containing N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate salt represented by the following formula as an active ingredient. Examples of the higher fatty acid amide sulfonate represented by the general formula (A) in the present invention include sodium salts of caproylmethyltaurine, lauroylmethyltaurine, myristoylmethyltaurine, palmitoylmethyltaurine, stearoylmethyltaurine, and oleoylmethyltaurine. ,
Examples include potassium salts, ammonium salts, triethanolamine salts, and the like. Further, as the N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate salt represented by the general formula (B), for example, N-(2-lauryl-2-hydroxyethyl)- N-methylaminoethanol phosphate monosodium salt (hereinafter referred to as compound 1), N
-(2-lauryl-2-hydroxyethyl)-N
-Methylaminoethanol phosphate monopotassium salt (compound 2), N-(2-lauryl-2-
hydroxyethyl)-N-methylaminoethanol phosphate ester monoammonium salt (compound 3),
N-(2-lauryl-2-hydroxyethyl)-
N-methylaminoethanol phosphate ester 1 triethanolamine salt (compound 4), N-(2-
Capryl-2-hydroxyethyl)-N-methylaminoethanol phosphate monosodium salt (Compound 5), N-(2-capryl-2-hydroxyethyl)-N-methylaminoethanol phosphate monopotassium salt (Compound 5) 6), N-(2-
Capryl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester 1 ammonium salt (compound 7), N-(2-capryl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester 1 triethanolamine salt (Compound 8), N-(2-Myristyl-2-hydroxyethyl)-N-methylaminoethanol phosphate monosodium salt (Compound 9), N-(2-Myristyl-2-hydroxyethyl)-N-methyl Aminoethanol phosphate monopotassium salt (Compound 10), N-(2-myristyl-2-hydroxyethyl)-N-methylaminoethanol phosphate monoammonium salt (Compound 11), N-
(2-myristyl-2-hydroxyethyl)-N
-Methylaminoethanol phosphate ester 1 triethanolamine salt (compound 12), N-(2-palmityl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester 1 sodium salt (compound 13), N-(2 -palmityl-2-hydroxyethyl)-N-methylaminoethanol phosphate monopotassium salt (compound 14), N-(2
-palmityl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester 1 ammonium salt (compound 15), N-(2-palmityl-2
-Hydroxyethyl)-N-methylaminoethanol phosphate ester 1 triethanolamine salt (Compound 16), N-(2-stearyl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester 1 sodium salt (Compound 17) ), N-
(2-stearyl-2-hydroxyethyl)-N
-Methylaminoethanol phosphate monopotassium salt (compound 18), N-(2-stearyl-2
-Hydroxyethyl)-N-methylaminoethanol phosphate monoammonium salt (compound
19), (2-stearyl-2-hydroxyethyl)
-N-methylaminoethanol phosphate 1
Triethanolamine salt (compound 20), N-(2
-oleyl-2-hydroxyethyl)-N-methylaminoethanol phosphate monosodium salt (compound 21), N-(2-oleyl-2-hydroxyethyl)-N-methylaminoethanol phosphate monopotassium salt ( Compound 22), N-
(2-oleyl-2-hydroxyethyl)-N-
These include methylaminoethanol phosphate 1 ammonium salt (Compound 23) and N-(2-oleyl-2-hydroxyethyl)-N-methylaminoethanol phosphate 1 triethanolamine salt (Compound 24). Although the higher fatty acid amide sulfonate represented by the general formula (A) has sufficient surfactant properties such as foaming properties and detergent properties, it has a strong protein denaturing power and cannot reach the desired low level when used alone. No irritating cleaning agents are obtained. On the other hand, the N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate salt represented by the general formula (B) has very low protein denaturing power and weak irritation. In addition, it has good surfactant properties such as foaming properties and detergency. The present inventors have developed a higher fatty acid amide sulfonate represented by the general formula (A) and N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol represented by the general formula (B). It was discovered that when phosphoric acid ester salts are mixed at a certain ratio, phenomena such as increased viscosity and decreased critical micelle concentration occur compared to the case of each alone. -Alkyl-2-
It was presumed that a complex was formed with N-methylaminoethanol (hydroxyethyl)-N-methylaminoethanol phosphoric acid ester salt, but in this mixture at a certain ratio, surfactant properties such as foaming and detergent properties were lower than that of higher fatty acid amide sulfone. It is not inferior to the case of the acid salt alone, and at the same time, the protein denaturation power is significantly reduced to almost the same level as the case of the N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester salt alone. This is what I discovered. That is, by mixing to form a complex,
This clearly shows a synergistic effect, and we succeeded in obtaining a hypoallergenic detergent composition that maintains excellent surfactant ability and has low protein denaturation ability. The mixing ratio (weight ratio) of (A):(B) is preferably in the range of 3:1 to 1:20. If the mixing ratio is outside this range or if a large amount of other anionic surfactant is added to disrupt the balance of the system, a sufficient effect of lowering protein denaturation performance cannot be obtained. In addition, the content of (A) + (B) in the total amount of the cleaning composition is
10 to 50% by weight is preferred. The cleaning composition of the present invention may optionally contain components commonly added to cleaning agents, such as higher alcohols, lanolin derivatives, protein derivatives, and oily components such as fatty acid esters of polyethylene glycol.
Humectant ingredients such as propylene glycol, glycerin, and polyethylene glycol, nonionic surfactants such as fatty acid alkolamide, polyoxyethylene alkyl ether, and alkyl amine oxide, and water-soluble polymeric substances (anionic, nonionic, and cationic) ), sequestering agents, preservatives, bactericidal agents, PH regulators, ultraviolet absorbers, antioxidants, pigments, fragrances, etc. (Example) Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited thereto. Prior to the examples, the test methods and evaluation methods employed in each example will be explained. Foaming test method: Tested according to the Ross Miles test method (ASTMD 1173-53). In addition, the evaluation criteria were set as follows. 〇…Good lathering Foam volume 200ml or more △…Normal foaming Foam volume 150ml or more Less than 200ml×…Poor foaming Foam volume less than 150ml Cleaning test method Lanolin 7% on a 5cm x 5cm wool muslin cloth
0.4 ml of a 0.005% chloroform solution of Sudan and Sudan was evenly applied and dried, and the contaminated cloth was placed in a glass cylinder of approximately 100 ml containing 40 ml of a 3% detergent solution, and placed in a constant temperature bath at 40°C for 15 minutes. After shaking, the dirty washing cloth was thoroughly rinsed under running water, dried, and the reflectance was examined, and the cleaning rate was determined by the following formula. Cleaning rate=Reflectance after cleaning−Reflectance before cleaning/Reflectance of original fabric−Reflectance before cleaning In addition, evaluation criteria were set as follows. 〇: Good cleaning performance Cleaning efficiency 80% or more △: Average cleaning performance Washing efficiency 60% or more Less than 80% The ovalbumin denaturation rate when a sample was added to a PH7 buffer solution at a test concentration of 1% was measured using an absorption peak at 220 nm. Denaturation rate (%) = Ho−Hs/Ho×100 Ho: Height of the 220nm absorption peak of ovalbumin Hs: Height of the 220nm absorption peak when the sample is added to the ovalbumin buffer solution The evaluation criteria are as follows: It was set to ◎: Ovalbumin denaturation rate less than 30% 〇: Ovalbumin denaturation rate 30% or more but less than 60% △: Ovalbumin denaturation rate 60% or more but less than 80% ×: Ovalbumin denaturation rate 80% or more Rough hand test method For each sample, male and female Using a panel of 5 people each, 10 people in total, with one hand on either the left or right hand, sample concentration 5
%, and the other hand was immersed in water at the same temperature for 10 minutes in an aqueous solution at a temperature of 35°C, twice a day for two consecutive days, and the difference in rough skin between the left and right hands was visually determined. ◎... Extremely weak hand roughness 0 to 1 out of 10 people Rough hands were observed on the sample side 〇... Hand roughness was slightly weak 2 to 4 out of 10 people Rough hands were observed on the sample side △... Hand roughness was slightly strong 10 people 5 to 7 middle school participants Rough hands were observed on the sample side ×... Extremely rough hands 8 to 10 out of 10 Rough hands were observed on the sample side Examples 1 to 8, Comparative Examples 1 to 7 Examples 1 to 8 In Comparative Examples 1 to 7, shampoos having the compositions listed in Tables 1 and 2 were prepared, and their foaming properties, detergency, protein denaturation rate, and roughness on hands were investigated. and shown in Table 2.

【table】

【table】

[Table] Example 9 A body shampoo having the following composition was prepared. Myristylmethyltaurine-K 8% (weight) Compound 1 6 Compound 5 6 Glycerin 2 Fragrance 0.3 Water Residual As a result of investigating the foaming properties, cleansing properties, protein denaturation rate, and roughness on hands of this body shampoo, the results were 〇, 〇, respectively.
It was ◎, ◎. Example 10 A shampoo having the following composition was prepared. Cocoyl methyl taurine-Na 4 Compound 4 8 Compound 8 8 Coconut fatty acid diethanolamide 5 Fragrance 0.3 Water Residual As a result of investigating the foaming properties, detergency, protein denaturation rate, and roughness of hands of this shampoo, the results were 〇, 〇, ◎, respectively. ◎
It was hot.

Claims (1)

[Claims] 1 General formula (A) (In the above formula, R ₁ is a caprylic, lauryl, myristyl, palmityl, stearyl, isostearyl, or oleyl group, and M ₁ is sodium, potassium, ammonium, or triethanolammonium.) Fatty acid amide sulfonate and general formula (B) (In the above formula, R ₂ is a caprylic group, a lauryl group,
myristyl, palmityl, stearyl or oleyl group, _M2 is sodium, potassium, ammonium or triethanolammonium. ) A hypoallergenic detergent composition containing N-(2-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester salt as an active ingredient. 2 Higher fatty acid amide sulfonate represented by the above general formula (A) and N-(2
-alkyl-2-hydroxyethyl)-N-methylaminoethanol phosphate ester salt, the weight ratio is in the range of 3:1 to 1:20, and (A) + (B)
The content of is 10 to 50% by weight in the total amount of the cleaning composition.
The hypoallergenic cleaning composition according to claim 1.