JPH0860182A - Detergent composition - Google Patents

Abstract

PURPOSE: To obtain a low-irritant, highly stable cleansing agent composition for use on the skin, etc., having high foamability and foam stability and foam extraction when rinsed away, comprising an N-acyl-N-carboxyethylglycine derivative and a saccharide-based surfactant. CONSTITUTION: This low-irritant cleansing agent composition for use on the skin, etc., comprises (A) an N-acyl-N-carboxyethylglycine derivative of formula I (R<1> is a 5-21C alkyl, alkenyl or hydroxyalkyl; M<1> and M<2> are each H, an alkali metal, alkaline earth metal, ammonium, 1-22C mono-, di-or trialkanolammonium, 1-22C alkyl-or alkenyl-substituted pyridinium, 2-500C and 2-250NH2 polyalkylenepolyamine or basic amino acid group) and (B) a saccharide-based surfactant of formula II (R<2> is a 8-18C alkyl, alkenyl or alkylphenyl; R<3> is a 2-4C alkylene; G is a 5-6C reducing sugar; (m) is 0-10; (n) is 1-10).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a detergent composition, and more particularly, it has a good foaming property during cleaning, has a good foaming property during rinsing, does not cause slimy skin, and is irritating to the skin. The present invention relates to a detergent composition which has a small amount and is excellent in storage stability.

[0002]

2. Description of the Related Art Cleaning compositions such as kitchen cleaners, hair cleaners and body cleaners generally contain an anionic surfactant as a main component and mainly contain higher fatty acid salts (soaps) and alkyl sulfates. , Sulfonate, etc. are used. However, for example, when soap is used for cleaning the skin, soap scum (higher fatty acid Ca salt) is generated during rinsing and adheres to the skin, so that the lubricity of the skin surface is significantly lowered, and there is a drawback that squeak and tightness occur. there were. Further, when an alkylsulfate or a sulfonate is used for hair washing, it has no squeaky feeling or tightness, but has drawbacks such as poor foam breakage and poor lubricity of hair.

Therefore, for the purpose of improving these drawbacks, attempts have been made to blend various auxiliaries such as oil components such as higher alcohols and co-activators. However, when such auxiliaries are added, cleaning is performed. Since the effect, the foaming power, the feeling of use, etc. are deteriorated, it is difficult to obtain a sufficiently satisfactory cleaning agent because it is easily restricted by prescription.

Further, detergent compositions containing an acylimino dibasic acid type anionic surfactant have been investigated (JP-A-2-84496, JP-A-5-117139, JP-A-6-80987). These cleaning agents
Although the foaming power, the feeling of use, etc. are improved, the acylimino dibasic acid type anionic surfactant used as a cleaning agent is a derivative from iminodiacetic acid, and storage stability is particularly poor at low temperatures. There was a problem.

[0005]

SUMMARY OF THE INVENTION Accordingly, the object of the present invention is to have good foaming, foam retention, good foaming during rinsing, no stickiness, low irritation, and low temperature storage stability. Another object is to provide an excellent cleaning composition.

[0006]

Under such circumstances, as a result of intensive studies, the present inventors have found that when a specific glycine derivative and a sugar-based surfactant are used in combination, good foaming and foam retention during washing are achieved. It was found that a detergent composition having a good defoaming property at the time of rinsing, which does not cause sliminess, has less irritation to the skin, and is excellent in low temperature storage stability, and completed the present invention. did.

That is, the present invention provides (A) general formula (1)

[0008]

[Chemical 3]

(In the formula, R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 5 to 21 carbon atoms, and M ¹ and M ² are the same or different and each represents a hydrogen atom or an alkali metal. , Alkaline earth metal, ammonium, mono-, di- or trialkanol ammonium having 1 to 22 carbon atoms, pyridinium substituted with alkyl or alkenyl group having 1 to 22 carbon atoms, 2 to 500 carbon atoms in total
And a glycine derivative represented by a polyalkylene polyamine having a total amino number of 2 to 250, or a basic amino acid), and (B) a general formula (2)

[0010]

[Chemical 4] R ^2- (OR ³ ) _m -G _n (2)

(In the formula, R ² represents a linear or branched alkyl group, alkenyl group or alkylphenyl group having 8 to 18 carbon atoms, R ³ represents an alkylene group having 2 to 4 carbon atoms, and G represents A residue derived from a reducing sugar having 5 to 6 carbon atoms,
(m is a number from 0 to 10 and n is a number from 1 to 10) The present invention provides a detergent composition containing a sugar-based surfactant.

The component (A) used in the present invention is a glycine derivative represented by the above general formula (1). Where R
Straight or branched chain alkyl group having a carbon number of 5 to 21 represented by ^1, the alkenyl group, a hydroxyalkyl group,
For example, n-pentyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group,
Examples thereof include n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-heptadecyl group, methylhexadecyl group, ethylpentyl group, heptadecenyl group and hydroxyundecyl group. Of these, an alkyl group having 5 to 21 carbon atoms, from the viewpoint of foamability,
An alkenyl group is preferable, and one having 9 to 15 carbon atoms is particularly preferable.

In the general formula (1), as M ¹ and M ² , for example, hydrogen atom, sodium, potassium, magnesium, calcium, ammonium, monoethanolammonium, diethanolammonium, triethanolammonium, ethylenediamine, propylenediamine, Arginine, histidine, lysine and the like can be mentioned.
Of these, sodium, potassium, triethanolammonium and arginine are preferable, and sodium and potassium are particularly preferable.

As the glycine derivative (1) as the component (A), N-lauroyl-N-carboxyethylglycine sodium salt, N-lauroyl-N-carboxyethylglycine potassium salt, N-lauroyl-N-carboxyethylglycine trichloride is used. Ethanol ammonium salt, N-myristyl-N-carboxyethylglycine sodium salt,
N-myristyl-N-carboxyethylglycine potassium salt, N-myristyl-N-carboxyethylglycine triethanolammonium salt, N-myristyl-N-
Carboxyethylglycine arginine salt is preferred.

Such a glycine derivative (1) can be produced, for example, according to the reaction formula shown below.

[0016]

[Chemical 5]

That is, glycine represented by the general formula (3) or a salt thereof is reacted with acrylonitrile to obtain a glycine derivative (4) (step A), which is hydrolyzed.
If necessary, salt exchange is performed to obtain a glycine derivative (7) (step B), and then this is reacted with an acid chloride (5),
By carrying out salt exchange if necessary (step E), (A)
The component glycine derivative (1) can be obtained. Further, the glycine derivative (4) obtained in the step A is reacted with an acid chloride (5), and if necessary, salt exchange is performed to obtain a glycine derivative (6) (step C), which is then hydrolyzed. By optionally performing salt exchange (step D), the glycine derivative (1) as the component (A) can be obtained.

Each step will be described below. (Step A) In this step, glycine or its salt (3) is reacted with acrylonitrile to obtain a glycine derivative (4). Glycine or a salt thereof as a raw material, and acrylonitrile may be produced by known methods, any commercially available one may be used, but if necessary, recrystallization, purification by distillation, etc. You may use.

Specific examples of glycine or its salt (3) include glycine, glycine sodium salt, glycine potassium salt, glycine lithium salt, glycine magnesium salt,
Glycine calcium salt, glycine ammonium salt, glycine ethylenediamine salt, glycine propylenediamine salt and the like can be mentioned, and glycine sodium salt, glycine potassium salt and glycine ammonium salt are particularly preferable.

In this step, glycine or its salt (3) and 0.5 to 10 equivalents of acrylonitrile in water are heated at a suitable temperature of 10 to 100 ° C., preferably 30 to 70 ° C. for 0.5 to 100 ° C. The glycine derivative (4) can be obtained by reacting for a time, preferably 1 to 3 hours, and further, if necessary, by exchanging a counter ion using an electrodialyzer or the like. When the reaction time is longer than 100 hours, side reactions such as hydrolysis of the cyano group occur concurrently, which is not preferable. During the reaction, if a treatment such as gradually adding acrylonitrile to an aqueous solution of glycine or a salt thereof (3) is performed, side reactions such as polymerization of acrylonitrile are significantly suppressed, and the yield is improved, which is preferable. The glycine derivative (4) obtained in this step can be used as it is in the next step, but if necessary, it is recrystallized using a solvent such as water, methanol or ethanol to obtain a highly purified product. You can also

(Step B) This step is a step of hydrolyzing the cyano group of the glycine derivative (4) obtained in step A, preferably in the presence of a basic substance, to obtain a glycine derivative (7). . Examples of the basic substance used here include alkali metal hydroxides and alkaline earth metal hydroxides, and specific examples include sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide,
Examples thereof include barium hydroxide.

In this step, the glycine derivative (4)
In an aqueous solution in the presence of 0.1 to 30 equivalents of a basic substance, if necessary, in a mixed solution of water and a polar solvent such as methanol, ethanol, isopropanol, acetone, 1,3-propanediol, and propylene glycol. At 50
To obtain a glycine derivative (7) by reacting at a suitable temperature of -100 to 100 ° C, preferably 70 to 100 ° C for 0.5 to 100 hours, and further, if necessary, by exchanging a counter ion using an electrodialyzer or the like. You can The glycine derivative (7) obtained in this step can be used as it is in the next step, but if necessary, it is recrystallized using a solvent such as water, methanol or ethanol to obtain a highly purified product. You can also

(Step C) In this step, the glycine derivative (4) obtained in step A is reacted with an acid chloride (5), preferably in the presence of an alkaline substance, to obtain a glycine derivative (6). is there. As the acid chloride (5) as a raw material, any of those produced by a known method and those commercially available may be used, but those obtained by purification such as distillation may be used if necessary. Acid chloride (5)
Specific examples of, hexanoic acid chloride, octanoic acid chloride, decanoic acid chloride, dodecanoic acid chloride, tetradecanoic acid chloride, hexadecanoic acid chloride, octadecanoic acid chloride, 2-ethylhexanoic acid chloride, isostearic acid chloride, oleic acid chloride, etc. Fatty acid chlorides having a single composition, such as fatty acid chlorides, coconut oil fatty acid chlorides, and beef tallow fatty acid chlorides, can be mentioned.

In this step, the glycine derivative (4)
And usually 0.8 to 5.0 equivalents, preferably 0.9 to 1.3
Equivalent amount of acid chloride (5) in an aqueous solution, if necessary, in a mixed solution of water and a polar solvent such as methanol, ethanol, isopropanol, acetone, 1,3-propanediol, propylene glycol, 0 to 100 ° C. The glycine derivative (6) can be obtained by reacting at a suitable temperature of preferably 10 to 50 ° C. for 0.5 to 100 hours, and further, if necessary, by exchanging a counter ion using an electrodialyzer or the like. If the amount of the acid chloride (5) used is less than the above range, a large amount of the glycine derivative (4) remains in the reaction product, and if it is more than the above range, the unreacted acid chloride (5) remains unreacted. A large amount of fatty acid is by-produced from 5), which is not preferable.

In this step, in order to secure the reactivity and allow a certain reaction to proceed, an alkaline substance is added to the reaction system to bring the pH in the system to the alkaline side, preferably pH 9.0 to 9.0.
It is desirable to keep it in the range of 11.0. When the pH of the reaction system is lower than this range, hydrochloric acid, which is a by-product of the reaction, forms a salt with the unreacted glycine derivative (4) and the reaction does not proceed sufficiently, while the pH is higher than this range. In this case, the decomposition of acid chloride (5) is promoted and a large amount of fatty acid is produced as a by-product. Specific examples of the alkaline substance used include inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide and sodium carbonate, and organic bases such as triethylamine, pyridine and 4- (dimethylamino) pyridine. But especially sodium hydroxide,
Potassium hydroxide is practical. The amount of these alkaline substances used is an amount that maintains the system pH within the above range.

The glycine derivative (6) obtained in this step can be used as it is in the next step. If necessary, it may be recrystallized using a solvent such as water, methanol or ethanol, or hydrochloric acid, sulfuric acid or the like. After treatment with strong acid
An acid type product of glycine derivative (6) is obtained, and recrystallized using a solvent such as acetone, hexane, petroleum ether, methanol, ethanol, butanol, and the glycine derivative ( By adopting 6), a highly purified product can be obtained.

(Step D) This step is a step of hydrolyzing the cyano group of the glycine derivative (6) obtained in step C, preferably in the presence of a basic substance, to obtain a glycine derivative (1). . Examples of the basic substance used here include alkali metal hydroxides and alkaline earth metal hydroxides, and specific examples include sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide,
Examples thereof include barium hydroxide.

In this step, the glycine derivative (6)
In the presence of 0.1 to 30 equivalents of a basic substance in an aqueous solution,
If necessary, in a mixed solution of water and a polar solvent such as methanol, ethanol, isopropanol, acetone, 1,3-propanediol, and propylene glycol, 50-
The glycine derivative (1) can be obtained by reacting at an appropriate temperature of 100 ° C., preferably 70 to 100 ° C. for 0.5 to 100 hours, and further, if necessary, by exchanging a counter ion using an electrodialyzer or the like. it can.

The glycine derivative (1) obtained in this step can be used as it is in a detergent composition, but if necessary, it is recrystallized using a solvent such as water, methanol or ethanol, or hydrochloric acid or sulfuric acid. After treatment with a strong acid such as glycine derivative (1), obtain the acid type product of glycine derivative (1) and recrystallize it using a solvent such as acetone, hexane, petroleum ether, methanol, ethanol, butanol, etc. By using a glycine derivative (1) with a solvating agent, a highly purified product can be obtained.

(Step E) In this step, the glycine derivative (7) obtained in Step B is reacted with an acid chloride (5), preferably in the presence of an alkaline substance, to obtain a glycine derivative (1). is there. The same acid chloride (5) as the raw material may be the same as in step C.

In this step, the glycine derivative (7)
And usually 0.8 to 5.0 equivalents, preferably 0.9 to 1.3
Equivalent amount of acid chloride (5) in an aqueous solution, if necessary, in a mixed solution of water and a polar solvent such as methanol, ethanol, isopropanol, acetone, 1,3-propanediol, propylene glycol, 0 to 100 ° C. The glycine derivative (1) can be obtained by reacting at an appropriate temperature of preferably 10 to 50 ° C. for 0.5 to 100 hours, and further, if necessary, by exchanging a counter ion using an electrodialyzer or the like. If the amount of the acid chloride (5) used is less than the above range, a large amount of the glycine derivative (7) remains in the reaction product, and if it is more than the above range, unreacted acid chloride (5) A large amount of fatty acid is by-produced from 5), which is not preferable.

In this step, in order to secure the reactivity and allow a certain reaction to proceed, an alkaline substance is added to the reaction system to bring the pH in the system to the alkaline side, preferably pH 9.0 to 9.0.
It is desirable to keep it in the range of 11.0. When the pH of the reaction system is lower than this range, hydrochloric acid, which is a by-product of the reaction, forms a salt with the unreacted glycine derivative (7) and the reaction does not proceed sufficiently, while the pH is higher than this range. In this case, the decomposition of acid chloride (5) is promoted and a large amount of fatty acid is produced as a by-product. Specific examples of the alkaline substance used here include sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, inorganic bases such as sodium carbonate,
Triethylamine, pyridine, 4- (dimethylamino)
Examples thereof include organic bases such as pyridine, but sodium hydroxide and potassium hydroxide are particularly practical. The amount of these alkaline substances used is an amount that maintains the system pH within the above range.

The glycine derivative (1) obtained in this step can be used as it is in a detergent composition, but if necessary, the same post-treatment as in step D is carried out to obtain a highly purified product. You can also

The glycine derivative as the component (A) can be used alone or in combination of two or more kinds. The blending amount of the component (A) in the detergent composition of the present invention varies depending on the formulation of the detergent and the like, but is preferably 2 to 60% by weight (hereinafter simply referred to as%) in the total composition, Especially 5-5
A content of 0% is preferable because it gives good foaming and gives a refreshing feeling after washing.

The component (B) used in the present invention is the sugar-based surfactant represented by the general formula (2). Where R
^As the linear or branched alkyl group, alkenyl group or alkylphenyl group having 8 to 18 carbon atoms represented by ² ,
An alkyl group having 10 to 14 carbon atoms is preferable, and a decyl group, a dodecyl group, and a tetradecyl group are particularly preferable. Also, R
The alkylene group having 2 to 4 carbon atoms represented by ³ is preferably an ethylene group or a propylene group. G has 5 to 6 carbon atoms
Is a residue derived from the reducing sugar of, and its structure is determined by a monosaccharide or two or more sugars used as a raw material. Examples of the raw material of G include monosaccharides such as glucose, galactose, fructose, xylose, mannose, lyxose, arabinose and mixtures thereof.
Examples thereof include lactose, sucrose, nigerose, turanose, raffinose, gentianose, melezitose, and mixtures thereof. Of these, glucose, galactose and fructose are particularly preferable.

Further, m represents a number from 0 to 10, but especially 0
~ 2 is preferred. n is an average degree of sugar polymerization and represents a number of 1 to 10, but it is preferably selected in consideration of physical properties derived from R ² . For example, when R ² is a hydrophobic group having 8 to 11 carbon atoms, n = 1 to 1.4, and when R ² is a hydrophobic group having 12 to 14 carbon atoms, n = 1.5 to 4.0. preferable.
The average sugar polymerization degree n is determined by the proton-NMR method.

As the sugar-based surfactant as the component (B), an alkyl polyglucoside (R ² -G _n ) in which m = 0 and G is a residue derived from glucose is particularly preferable.

The sugar surfactant as the component (B) may be used alone or in combination of two or more kinds. The blending amount of the component (B) in the detergent composition of the present invention varies depending on the formulation of the detergent, etc., but is preferably 2 to 60% in the total composition, and particularly preferably 5 to 50%. It is preferable because it exhibits excellent foaming and further improves the low temperature storage stability.

In the detergent composition of the present invention, the mixing ratio of the component (A) and the component (B) is (A) / (B) by weight.
= 1/30 to 30/1 is preferable, and particularly 1/10 to 10
The ratio is preferably 1/1, more preferably 1/1 to 4/1.

In the detergent composition of the present invention, a surfactant other than the above, for example, an anionic surfactant such as N-acyl sarcosine salt, alkyl ether sulfate, polyoxyethylene alkyl ether sulfate, or the like; polyoxyethylene Nonionic surfactants such as alkyl ethers, sugar ester-based and sugar amide-based surfactants; amphoteric surfactants such as imidazoline-based and betaine-based surfactants can be optionally used in combination as long as the effects of the present invention are not impaired.

Further, as other additives, components usually used in detergents, for example, viscosity modifiers such as carboxyvinyl polymer, methyl cellulose, ethanol, polyoxyethylene glycol distearate; pearling agents, fragrances, dyes, and UV absorption. Agents, antioxidants, bactericides, anti-inflammatory agents, preservatives and the like can be optionally added within a range that does not impair the effects of the present invention.

The detergent composition of the present invention can be produced according to a conventional method, and its dosage form is not particularly limited, and may be any liquid form, paste form, cream form, solid form, powder form or the like. In particular, it is preferably in the form of liquid, paste or cream. In the case of a liquid, it is preferable to use water as the liquid medium, and the content of water is preferably 50 to 90% in the total composition. Further, the cleansing composition of the present invention is suitable as a cleansing agent for the body such as skin and hair, and is particularly preferably used for cleansing the skin.

In the detergent composition of the present invention, the pH of the aqueous solution when diluted 10 times by weight with water is preferably 4 to 9, particularly 5 to 7. In order to obtain a preferable pH, it may be adjusted by adding an acid or an alkali to the detergent composition, and an equimolar ion exchange may be performed with respect to the component (A).

[0044]

EFFECT OF THE INVENTION The detergent composition of the present invention has good lathering and lathering characteristics during washing, has good lathering during rinsing, does not cause slimy skin, and is less irritating to the skin, and has low temperature. It has excellent storage stability, especially on the body,
It is useful as a skin cleanser for the face.

[0045]

EXAMPLES Next, the present invention will be further described with reference to examples, but the present invention is not limited to these examples.

Synthesis Example 1 (Synthesis of N-carboxyethyl-N-lauroylglycine) (1) Production of N-cyanoethylglycine sodium salt:
1 liter 4 equipped with stirrer, thermometer and dropping funnel
Glycine 150.77 g (2.0084)
mol) and 100 ml of water are charged, and NaOH is stirred with stirring.
An aqueous solution of 80.46 g (2.0115 mol) in 200 ml was added to give an aqueous solution of sodium salt of glycine. Then
106.7 g of acrylonitrile (2.0109
mol) was added dropwise over about 30 minutes. During this period, the temperature in the system was kept at 40 to 70 ° C. Then, the reaction was completed by stirring at 60 ° C. for 2 hours. After completion of the reaction, the temperature in the system was cooled to room temperature to obtain 568 g (yield 97.8%) of a 51.9% aqueous solution of N-cyanoethylglycine sodium salt. A part of this product was dehydrated and dried to obtain a colorless powder.

(2) Production of N-cyanoethyl-N-lauroylglycine: A 1-liter four-necked flask equipped with a stirrer, a thermometer and a dropping funnel was charged with N-cyanoethylglycine sodium salt obtained in (1) above. 51.9% of
Aqueous solution 222.4 g (0.7689 mol) and acetone 5
0 ml was charged and ice-cooled. Then, 183.9 g (0.8406 mol) of dodecanoic acid chloride was added dropwise to this solution over 1 hour. During this period, the pH of the system was maintained at 9 to 11 while the temperature was 10 to 25 while dropping a 40% NaOH aqueous solution.
It was kept at ℃. After the completion of dropping, the mixture was stirred at room temperature for 2 hours.
Then, the pH of the reaction product was adjusted to 1.2 with concentrated hydrochloric acid, and the water-insoluble matter was extracted with chloroform. The obtained organic layer was concentrated and dried sufficiently to obtain N-cyanoethyl-
228.99 g of colorless powder of N-dodecanoylglycine
(Yield 95.9%) was obtained. The acid value of this product is 189.2.
(Theoretical value 180.73).

(3) Production of N-carboxyethyl-N-lauroylglycine: A 1-liter four-necked flask equipped with a stirrer, a thermometer and a condenser was used, and the N-cyanoethyl-N obtained in (2) above was used. -Lauroylglycine 110.
18 g (0.3549 mol) and 200 ml of water were charged, and while stirring, KOH 58.6 g (0.888 mol) of 2
A 00 ml aqueous solution was added. The solution was stirred at 90 ° C. for 2 hours, cooled to room temperature, and adjusted to pH 1.5 with concentrated hydrochloric acid. Water-insoluble matter was extracted with chloroform, and the obtained organic layer was concentrated and sufficiently dried to give N-carboxyethyl-N-lauroylglycine colorless powder 113.
71 g (yield 97.3%) was obtained.

Synthesis Example 2 (Synthesis of N-carboxyethyl-N-lauroylglycine sodium salt) (1) Production of N-carboxyethylglycine sodium salt: 2 liter four-neck equipped with stirrer, thermometer and dropping funnel Glycine 80.00 g (1.065
7 mol) and NaOH 42.63 g (1.066 mol)
160 ml of an aqueous solution was charged and heated with stirring. Next, 59.38 g of acrylonitrile (1.1
19 mol) was added dropwise over about 30 minutes. During this time, the temperature in the system was kept at 40 to 60 ° C. After stirring at 60 ° C for 1 hour, 63.95 g (1.5988 mol) of NaOH was added.
Of 300 ml of the above solution is further charged, and the temperature is raised to 80 ° C.
Stir for hours. During this period, nitrogen gas was blown into the reaction solvent and the generated ammonia gas was continuously driven out of the system.
After completion of the reaction, the temperature in the system was cooled to room temperature to obtain N-carboxyethylglycine sodium salt. A part of this product was dehydrated and dried to obtain a colorless powder.

(2) Production of N-carboxyethyl-N-lauroylglycine sodium salt: 150 ml of acetone was added to the aqueous solution of N-carboxyethylglycine sodium salt obtained in (1) above with continuous stirring. 228.29 g of dodecanoic acid chloride (1.043
5 mol) was added dropwise over 1.5 hours. During this period, 48%
The pH of the system was kept at 9 to 11 and the temperature was kept at 10 to 25 ° C. while dropping an aqueous solution of NaOH. After the completion of dropping, the mixture was stirred at room temperature for 2 hours. Then, the pH of the reaction product was adjusted to 7.0 with concentrated hydrochloric acid. The obtained aqueous solution was desalted using an electrodialyzer to reduce the salt concentration to 2% or less.
Then, water was removed using a rotary evaporator, and the residue was washed with acetone to obtain N-carboxyethyl-N-lauroylglycine sodium salt as a colorless powder.

Synthesis Example 3 (Synthesis of N-carboxyethyl-N-lauroylglycine potassium salt) 80.50 g of glycine was placed in a 2-liter four-necked flask equipped with a stirrer, a thermometer and a dropping funnel.
(1.0723 mol) and 60.20 g of KOH (1.0
73 mol) of 150 ml aqueous solution was charged and heated with stirring. Then, acrylonitrile 56.90 was added to this solution.
g (1.072 mol) was added dropwise over about 30 minutes, during which the temperature in the system was kept at 45 to 55 ° C. After stirring at 55 ° C for 1 hour, the mixture was cooled to room temperature. Next, 120 ml of water and 90 ml of acetone were added to the reaction solution, and 234.50 g (1.0719 mol) of dodecanoic acid chloride was added dropwise over 1 hour. During this period, the pH in the system was maintained at 9 to 11 while the temperature was 5 to 25 while dropping a 30% KOH aqueous solution.
It was kept at ℃. After the completion of dropping, the mixture was stirred at room temperature for 2 hours.
Then, a 30% KOH aqueous solution was added, and the total amount of KOH added for pH adjustment was 150.00 g (2.
673 mol), and the mixture was stirred at 80 ° C. for 2 hours. During this period, nitrogen gas was blown into the reaction solution and the generated ammonia gas was continuously driven out of the system. afterwards,
The reaction solution was cooled to room temperature, and the pH of the system was adjusted to 6.0 with concentrated hydrochloric acid. The resulting aqueous solution is desalted using an electrodialyzer to obtain N-carboxyethyl-N-
Lauroylglycine potassium salt was obtained as an aqueous solution.

Example 1 A detergent composition was produced by uniformly mixing the components having the compositions shown in Tables 1 and 2 and adjusting the pH with hydrochloric acid. In addition,
For the pH of each cleaning composition, prepare a 10-fold-fold diluted aqueous solution, and take 50 ml of this solution at a temperature of 25 ° C.
It was measured using a pH meter F-14 manufactured by HORIBA.
The obtained cleaning composition was evaluated for storage stability, foaming and feeling of use. The results are shown in Tables 1 and 2.

(Evaluation method) (i) Storage stability: A glass screw tube was filled with 50 ml of each detergent composition and sealed, and stored for 1 month in a thermostatic chamber at 5 ° C. After one month, the liquid state of the content was visually observed and evaluated according to the following criteria. ◯: It is a uniform transparent liquid. X: Crystals are precipitated or cloudy.

(Ii) Foaming: For each cleaning composition,
A 10-fold diluted aqueous solution was prepared, and 100 ml of this aqueous solution (liquid temperature 40 ° C.) was poured into a graduated cylinder. Next, a stirring blade was installed in the aqueous solution, the blade was rotated, and the volume (ml) of the foam generated 30 seconds after the start of stirring was measured as the foaming amount, and evaluated according to the following criteria. The rotation speed of the stirring blade was 1000 rpm and it was reversed every 5 seconds. ◎; foaming amount of 200 ml or more. ○: Foaming amount of 160 ml or more and less than 200 ml. Δ: Foaming amount of 120 ml or more and less than 160 ml. X: Foaming amount less than 120 ml.

(Iii) Feeling of use: Panels of 10 men and women were asked to wash their bodies for 1 week using each detergent composition, and sensory evaluation was conducted on the following items.
For evaluation, the average value was calculated based on the following criteria, and the average value was 4.
5 or more is very good (⊚), 3.5 to 4.4 is good (∘), 2.5 to 3.4 is normal (△),
The case of 2.4 or less was judged to be defective (x). (1) Foaming; 5; Good foaming. 4; Good foaming. 3; Normal. 2; Somewhat bad foaming. 1; Poor foaming. (2) Sustainable foam; 5; Sustainable foam. 4; Slightly good foam retention. 3; Normal. 2; Poor foam retention. 1; Poor foam retention. (3) Defoaming during rinsing; 5; Good defoaming. 4; The foam is slightly broken. 3; Normal. 2; Somewhat poor foaming. 1; Out of foam is bad. (4) Refreshing feeling when towel-drying; 5; Refreshing. 4; A little refreshing. 3; Normal. 2; A little slimy. 1; slimy.

[0056]

[Table 1]

[0057]

[Table 2]

As is clear from the results of Tables 1 and 2,
The cleaning composition of the present invention was excellent in storage stability, foaming and feeling of use. It also has excellent cleaning power,
The irritation to the skin was also extremely low.

Example 2 (Whole body cleaning agent)

[Table 3] (Component) (%) (1) N-lauroyl-N-carboxyethylglycine sodium 20 (2) Alkyl saccharide (in the general formula (2), R ² = C ₁₀ H ₂₁ , m = 0, G = Glucose, n = 11) 5 (3) Methylcellulose 0.1 (4) Perfume 0.5 (5) Ethanol 3 (6) Sodium hydroxide 2 (7) Purified water balance

(Manufacturing method) Components (1) and (6) were added to heated purified water and dissolved, and after cooling, components (2) to (5) were added.
Was added to obtain a transparent liquid detergent composition. The pH of a 10-fold diluted aqueous solution of the obtained detergent composition was 6.0. When the skin and the hair were washed with the obtained liquid detergent composition, the foaming and rinsing properties were good and a refreshing feeling was obtained, and the usability was excellent. In addition, it was less irritating to the skin and had good storage stability.

Example 3 (face wash)

[Table 4] (Component) (%) (1) N-lauroyl-N-carboxyethylglycine 20 (2) Arginine 12 (3) Alkyl saccharide (in the general formula (2), R ² = C ₁₀ H ₂₁ , m) = 0, G = glucose, n = 11) 10 (4) Lauryl dimethylamine oxide 3 (5) Perfume 0.5 (6) Sodium hydroxide suitable amount (7) Purified water balance

(Production Method) The component (2) was added to the heated purified water, and then the component (1) was added to neutralize and dissolve. After cooling this, the components (3) to (5) were added to obtain a transparent liquid detergent composition. The pH of a 10-fold diluted aqueous solution of the obtained detergent composition was 6.5. When the face was washed with the obtained liquid detergent composition, foaming and rinsing properties were good,
A refreshing feeling was obtained, and there was no feeling of dryness after drying, and the feeling of use was excellent. In addition, it was less irritating to the skin and had good storage stability.

Claims (1)

[Claims] 1. (A) General formula (1): (In the formula, R ¹ represents a linear or branched alkyl group, an alkenyl group or a hydroxyalkyl group having 5 to 21 carbon atoms, M ¹ and M ² are the same or different and each represents a hydrogen atom, an alkali metal or an alkaline earth group. Metal, ammonium, mono-, di-, or trialkanol ammonium having 1 to 22 carbon atoms, pyridinium substituted with alkyl or alkenyl group having 1 to 22 carbon atoms, polyalkylene having 2 to 500 carbon atoms and 2 to 250 total amino acids A glycine derivative represented by a polyamine or a basic amino acid), and (B) a general formula (2): R ^2- (OR ³ ) _m -G _n (2) (wherein R ² is a carbon A linear or branched alkyl group, alkenyl group or alkylphenyl group of the number 8 to 18,
R ³ represents an alkylene group having 2 to 4 carbon atoms, G is a residue derived from a reducing sugar having 5 to 6 carbon atoms, m represents a number of 0 to 10, and n represents a number of 1 to 10). A detergent composition containing a sugar-based surfactant represented by: