JP2002001086A - Surfactant and detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a surfactant which has an acyltaurine skelton and is excellent in foaming characteristics, foam quality, and persistence of foam and also in the feeling of use during and after cleaning. SOLUTION: This surfactant is obtained by reacting an acyltaurine salt of formula (1) R1CONR2C2H4SO3M1 with a taurine salt of formula (2) R3NHC2H4 SO3M2 (in the formulas, R1CO is an 8-22C aliphatic acyl group; R2 and R3 are each H or a 1-3C alkyl group; and M1 and M2 are each an alkali or alkaline earth metal, ammonium, or an organic ammonium) in the presence of an inorganic acid. A detergent composition containing the surfactant is also provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a surfactant,
Specifically, the present invention relates to a surfactant having an acyltaurine skeleton excellent in foam quality and usability.

[0002]

2. Description of the Related Art Fatty acid soaps, alkyl sulfates, alkyl ether sulfates and the like are mainly used as surfactants for personal cleansing agents. However, these were not always satisfactory surfactants with regard to irritation to the skin. Since personal cleansing agents come into direct contact with the skin, it is desirable to use surfactants with low irritation. Acylalkyl taurate type anionic surfactants have been used as surfactants having low irritation. Furthermore, acylalkyl taurate type anionic surfactants are characterized by high foaming properties and moderate detergency, and various detergent compositions combining other surfactants have been proposed. . For example, a detergent composition in which an alkyl betaine-type amphoteric surfactant and an alkylolamide-type nonionic surfactant are combined (Japanese Patent Publication No. 59-420).
No. 38), a detergent composition comprising a combination of an amine oxide type nonionic surfactant and an alkylolamide type nonionic surfactant (Japanese Patent Publication No. 2-26673), an amidobetaine type amphoteric surfactant , A detergent composition in combination with an alkylolamide type nonionic surfactant (JP-B-2-26677), a combination with an amidoamino acid type amphoteric surfactant and an alkylolamide type nonionic surfactant A combined detergent composition (Japanese Patent Publication No. 4-79398) and a detergent composition combined with a polyoxyethylene hydrogenated castor oil type nonionic surfactant (Japanese Patent Publication No. 6-845)
No. 10), a detergent composition in which an amide amino acid type ampholytic surfactant and a betaine type ampholytic surfactant are combined (JP-A-5-31193), and a combination with an alkyl iminodicarboxylate type ampholytic surfactant And the like (JP-A-6-172785). Conventionally, an acylalkyl taurate type anionic surfactant has an alkali metal or an alkaline earth metal as a counter ion, and the counter ion mainly used is sodium. These acyl alkyl taurate type anionic surfactants have a high foaming property but a coarse foam quality and poor foam sustainability.For example, when used as a shampoo base material, there is a squeaky feeling, When used as a body cleanser, there are problems such as a slimy feeling. further,
There is a problem that the low-temperature stability of the composition is impaired.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to eliminate the above-mentioned problems and to provide excellent foaming properties, foam quality and foam sustainability.
An object of the present invention is to provide a surfactant having an acyltaurine skeleton which is excellent in use during washing and after washing.

[0004]

The present invention provides: (a) an acyltaurine salt represented by the following formula (1) and a taurine salt represented by the following formula (2) in the presence of an inorganic acid:
A surfactant obtained by the reaction, R ¹ CONR ² C ₂ H ₄ SO ₃ M ¹ (1) R ³ NHC ₂ H ₄ SO ₃ M ² (2) (where R ¹ CO has 8 to 22 carbon atoms) R ² and R ³ each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and M ¹ and M ^{2 each} represent an alkali metal, an alkaline earth metal, ammonium, or an organic group; (B shows ammonium.) (B) A cleaning composition containing the surfactant described in (a).

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The acyltaurine salt represented by the formula (1) is an aliphatic acyl group having R ¹ CO of 8 to 22 carbon atoms, for example, capryloyl group, caprinoyl group, lauroyl group, myristoyl group, Palmitoyl group, stearoyl group, oleoyl group, araquinoyl group, behenoyl group,
Examples thereof include coconut oil fatty acid residues, palm oil fatty acid residues, palm kernel oil fatty acid residues, and tallow fatty acid residues, which are mixtures thereof. Preferably lauroyl group, myristoyl group,
Palmitoyl group, stearoyl group, oleoyl group, coconut oil fatty acid residue, palm oil fatty acid residue, palm kernel oil fatty acid residue, tallow fatty acid residue and the like. M ¹ is an alkali metal,
Alkaline earth metals, ammonium and organic ammonium, such as sodium, potassium, 1/2 calcium, 1/2 magnesium, ammonium, triethanol ammonium, monoethanol ammonium, diethanol ammonium and the like. Preferred are sodium and potassium, and more preferred is sodium.

R ² is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Preferred are a hydrogen atom, a methyl group and an ethyl group. These can be obtained, for example, by the following method. Acyl methyl taurine sodium salt is obtained by acylating methyl taurine sodium with a fatty acid chloride in the presence of sodium hydroxide.

In the taurine salt represented by the formula (2), R ³ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Preferred are a hydrogen atom, a methyl group and an ethyl group. M ² represents an alkali metal, alkaline earth metal, ammonium or organic ammonium, such as sodium, potassium, カ ル シ ウ ム calcium, １ ／ magnesium, ammonium, triethanol ammonium, monoethanol ammonium, diethanol ammonium and the like. Preferred are sodium, potassium, 1/2 magnesium and triethanolamine. However, it is practical to use the sodium salt as the taurine salt in view of the fact that it is commercially available as the sodium salt of methyl taurine, and the economics of synthesizing the taurine salt are taken into consideration.

[0008] The surfactant of the present invention is obtained by reacting an acyltaurine salt represented by the formula (1) with a taurine salt represented by the formula (2) in the presence of an inorganic acid. Examples of the inorganic acid include hydrochloric acid, nitric acid, and sulfuric acid, and hydrochloric acid is preferable in consideration of a salt produced as a result of a salt exchange reaction.
The amount of the taurine salt used is 0.9 to the acyl taurine salt.
A molar equivalent ratio of 5 to 1.25 times is desirable, particularly preferably 1.0 to 1.2 times. When the molar equivalent ratio is smaller than 0.95, the foam quality is coarse, and the sustainability of the foam and the feeling upon use during washing and after washing deteriorate. Also, 1.2
If it exceeds 5 times, the stability over time of the surfactant aqueous solution will be deteriorated. The inorganic acid is 0.95 to the acyltaurine salt.
It is desirable to use a molar equivalent ratio of ~ 1.25 times,
Particularly preferably, the molar equivalent ratio is 1.0 to 1.2 times. If the molar equivalent ratio is less than 0.95, the foam quality is coarse, and the sustainability of the foam and the feeling of use after washing deteriorate. Also, 1.
If it exceeds 25 times, the stability of the aqueous surfactant solution with time will deteriorate.

The reaction may be carried out by reacting a taurine salt with an inorganic acid and then reacting with an acyl taurine salt, or after mixing the taurine salt and the acyl taurine salt and then reacting by adding an inorganic acid. After reacting the taurine salt with hydrochloric acid, the reaction may be carried out with the taurine salt. Although there is no particular need to heat the reaction, it is desirable to raise the temperature to 30 ° C to 80 ° C, particularly preferably 50 to 80 ° C. If the temperature is lower than 30 ° C., the reaction time becomes longer, and the production efficiency is deteriorated. Heating at a temperature higher than 80 ° C. wastes energy. The pH of the aqueous solution of the surfactant prepared by this method is 6 to 8. Further, a sodium salt is by-produced in this aqueous solution. If the presence of the sodium salt is not preferable, an acyltaurine salt aqueous solution having a small salt content is used in advance, or the obtained aqueous solution of the surfactant is reverse osmosis membrane. Sodium chloride can be reduced by treatment using electrodialysis or electrodialysis.

[0010] The surfactant of the present invention can be used by being contained in various cleaning compositions. In particular, it can be suitably used for shampoo compositions and body soap compositions. Usually, 1 to 40% by weight is used in the detergent composition.

[0011]

EXAMPLES The present invention will be described specifically with reference to examples.
A surfactant was synthesized by the following method. Production Example 1 308.7 g of a 50% by weight aqueous solution of taurine sodium salt (molecular weight: 147) was placed in a two-liter four-necked flask.
(1.05 mol) and 106.5 g of 36% by weight hydrochloric acid (1.
05 mol) and stirred at 50 ° C. for 10 minutes. Next, 1329.9 g (1 mol) of a 27% by weight aqueous solution of coconut oil fatty acid methyltaurine sodium salt (molecular weight 358.8) was added, and the mixture was stirred at 50 ° C. for 30 minutes to obtain an aqueous solution of surfactant 1. Production Example 2 386.4 g of a 50% by weight aqueous solution of methyltaurine sodium salt (molecular weight: 161) was placed in a two-liter four-necked flask.
(1.2 mol), and palm kernel oil fatty acid taurine sodium salt (molecular weight 353.4), 26% by weight aqueous solution 135
9.2 g (1 mol) and 121.7 g of 36% by weight hydrochloric acid
(1.2 mol) and stirred at 80 ° C. for 15 minutes to obtain an aqueous solution of surfactant 2.

Production Example 3 296.9 g of a 50% by weight aqueous solution of taurine sodium salt (molecular weight: 147) was placed in a two-liter four-necked flask.
(1.01 mol) and 102.4 g of 36% by weight hydrochloric acid (1.
01 mol) and stirred at 50 ° C. for 10 minutes. Then
Lauroylmethyltaurine sodium salt (molecular weight 35
9) 1329.6 g (1 mol) of a 27% by weight aqueous solution was added and stirred at 70 ° C. for 20 minutes to obtain an aqueous solution of surfactant 3. Production Example 4 354.2 g of a 50% by weight aqueous solution of methyltaurine sodium salt (molecular weight: 161) was placed in a two-liter four-necked flask.
(1.1 mol), and 27% aqueous solution 127% of coconut oil fatty acid methyltaurine sodium salt (molecular weight: 344.8)
7.0 g (1 mol) and 111.5 g of 36% by weight hydrochloric acid
(1.1 mol) and stirred at 60 ° C. for 25 minutes to obtain an aqueous solution of surfactant 4.

Production Example 5 370.3 g of a 50% by weight aqueous solution of methyltaurine sodium salt (molecular weight: 161) was placed in a two-liter four-necked flask.
(1.15 mol) and 116.6 g of 36% by weight hydrochloric acid (1.
15 mol) and stirred at 50 ° C. for 20 minutes. Then
Lauroyl taurine sodium salt (molecular weight: 345) 27
1277.8 g (1 mol) of a water solution at 70% by weight was added.
The mixture was stirred for 20 minutes to obtain an aqueous solution of surfactant 5. Production Example 6 308.7 g of a 50% by weight aqueous solution of taurine sodium salt (molecular weight: 147) was placed in a two-liter four-necked flask.
(1.05 mol), 106.5 g of water was added, and 50 ° C, 1
Stirred for 0 minutes. Next, a 27% by weight aqueous solution of a coconut oil fatty acid methyltaurine sodium salt (molecular weight 358.8) 1
329.9 g (1 mol) was added, and the mixture was stirred at 50 ° C. for 30 minutes to obtain an aqueous solution of surfactant 6.

Production Example 7 308.7 g of a 50% by weight aqueous solution of taurine sodium salt (molecular weight: 147) was placed in a two-liter four-necked flask.
(1.05 mol) in water 48.5 g, sodium chloride 5
8.0 g was added, and the mixture was stirred at 50 ° C. for 10 minutes. Then
Coconut oil fatty acid methyltaurine sodium salt (molecular weight 35
8.8) 1329.9 g (1 mol) of a 27% by weight aqueous solution was added and stirred at 50 ° C. for 30 minutes to obtain an aqueous solution of surfactant 7.

Examples 1 to 5 and Comparative Examples 1 to 3 Surfactants were evaluated by the following evaluation methods. Table 1 shows the evaluation results. Evaluation method (a) Amount of sodium chloride The amount of sodium chloride was measured by alcohol-insoluble matter. About 3 g of the aqueous surfactant solution was placed in a 300 ml Erlenmeyer flask and precisely weighed. Next, 100 ml of isopropyl alcohol is added, and the mixture is boiled for 1 hour while being shaken occasionally on a water bath with a reflux cooling device. At the time of warming, this was filtered using a glass filter (1G3) having a predetermined weight, and the residue was washed with 100 ml of warm isopropyl alcohol.
After drying at 05 ° C for 2 hours, the weight of the glass filter was measured. The alcohol insoluble content was determined by the following equation. Alcohol insoluble content = {(weight of glass filter after measurement−weight of glass filter before measurement) / weight of sample} ×
100 (a) Residual dryness About 2 g of a sample was placed in a weighing bottle of known weight and precisely weighed.
Next, it was left still in a blow dryer set at 105 ° C. for 2 hours. After allowing to cool in a desiccator containing silica gel for 30 minutes, it was weighed. The remaining dry amount was determined by the following equation. Residual dry amount (%) = {(weight of weighing bottle after drying) − (weight of weighing bottle) / sample weight} × 100

(C) pH The pH of the aqueous surfactant solution was measured using a pH meter M-8 manufactured by Horiba, Ltd. The measurement was performed at 25 ° C. (D) Foaming force Surfactant with artificial hard water (prepared with calcium chloride and ion-exchanged water so as to be 100 ppm in terms of calcium carbonate) in a cup of a miller (model number: FM-100) manufactured by Iwatani Corporation. A test solution (50 g) diluted to a concentration of 1% by weight (the concentration of the surfactant was defined as a dry residue-sodium chloride) was weighed, and artificial waste (50% by weight of olive oil, 20% by weight of oleic acid) was added thereto. %, Lanolin 10
0.3 g of liquid paraffin, 10% by weight of liquid paraffin, and 10% by weight of squalene).
Let stand for hours. One hour later, the cup was attached to a miller, and the mixture was stirred at 3000 rpm for 5 seconds, and the height of the foam one minute after the stirring was stopped was measured. The height of the foam from the lowest position of the cup was measured and evaluated according to the following criteria. 〇: Bubble power is good (bubble height is 9 cm or more). ×: Insufficient bubble power (bubble height less than 9 cm). (E) Sustainability of foam In (D) above, the height of the foam 5 minutes after stopping stirring was measured, and evaluated by the numerical value obtained from the following equation. Persistence (%) = {(height of foam after 5 minutes) / (height of foam after 1 minute)} {}: high (90% or more) ×: low (less than 90%)

[0017]

[Table 1]

As shown in Table 1, the surfactants 1 to 5 of the present invention form sodium chloride and have excellent foam sustainability. In addition, the aqueous surfactant solution 6 containing no inorganic acid does not produce sodium chloride and has poor foam continuity. Further, the surfactant aqueous solution 7 in which sodium chloride is added and the composition of the composition is combined with the surfactant 1 is inferior in persistence of foam.

Examples 6 to 10 and Comparative Examples 4 to 6 The shampoo compositions shown in Table 2 were prepared, and
Foamability, foam quality and finger passage during rinsing were evaluated. Table 2 shows the evaluation results. (E) Foaming properties Ten males and females were panelists, and 5 g of the hair shampoo composition was used to evaluate the foaming properties when the hair and scalp were washed. From the total score of 20 people, 2 points were given when the foaming was felt good, 1 point when the foaming was slightly insufficient, and 0 when the foaming was felt bad.
It was rated on a scale. ：: good bubbling (30 points or more in total) △: somewhat bad bubbling (20 points or more and less than 30 points) ×: bad bubbling (less than 20 points in total) (f) Foam quality 10 for men and women Using the name as a panel, 5 g of the hair shampoo composition was used to evaluate the foam quality when the hair and scalp were washed. From the total score of 20 people, 2 points were given when the foam quality was good, 1 point when the foam quality was slightly insufficient, and 0 when the foam quality was bad. It was rated on a scale. ：: good foam quality (30 points or more in total) △: slightly poor foam quality (20 points or more and less than 30 points) ×: poor foam quality (less than 20 points in total)

(G) Finger passage at the time of rinsing Ten men and women were panelists. Using 5 g of the hair shampoo composition, the hair and scalp were washed, and the finger passage at the time of rinsing was evaluated. 2 if you do not feel squeaky
The score is 1 point when the creaking feeling is strong, and 0 when the creaking feeling is strong. From the total score of 20 people,
The following three levels were evaluated. ：: Good finger passing (total point 30 points or more) △: Slight finger passing (total point 20 points or more and less than 30 points) ×: Finger passing poor (total points less than 20 points)

[0021]

[Table 2]

From the results shown in Table 2, it can be seen that the surfactants of the present invention shown in Examples 6 to 10 are excellent in foaming property when used as a shampoo, foam quality, and as a finger when rinsing. . It can be seen that the conventional acylalkyl taurate-type anionic surfactant shown in Comparative Example 6 does not provide satisfactory foam quality and finger passing during rinsing. In Comparative Example 4 using the surfactant aqueous solution 6 to which no inorganic acid was added, the result was that both the foam quality and the finger passage during rinsing were not satisfactory. Further, in Comparative Example 5 using the surfactant aqueous solution 7 to which sodium chloride was added without adding the inorganic acid, the result was that both the foam quality and the finger passage during rinsing were not satisfactory.

[0023]

EFFECTS OF THE INVENTION The surfactant of the present invention has an acyltaurine skeleton, is hypoallergenic, has excellent foaming properties, has excellent foam quality and foam persistence, and has a good feeling during washing and after washing. Therefore, it can be suitably used as a cleaning base material for various detergent-combining substances such as a shampoo composition and a body soap composition.

Continued on the front page F term (reference) 4C083 AB052 AC302 AC642 AC791 AC792 AD282 CC23 CC38 DD23 EE03 EE09 EE21 4D077 AB10 AC07 BA13 CA02 DC02Y DC44Y DC48Y DC60Y DC80Y 4H003 AB23 AB46 AC13 BA12 DA02 EB08 EB42 ED21 FA17 FA

Claims (2)

[Claims] 1. A surfactant obtained by reacting an acyltaurine salt represented by the following formula (1) with a taurine salt represented by the following formula (2) in the presence of an inorganic acid. ^{_{R 1 CONR 2 C 2 H 4}} SO 3 M 1 (1) R 3 NHC 2 H 4 SO 3 M 2 (2) ( wherein, R ¹ CO is an aliphatic acyl group having 8 to 22 carbon atoms, R ² And R ³ each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and M ¹ and M ² represent an alkali metal, an alkaline earth metal, ammonium or organic ammonium.) 2. A detergent composition comprising the surfactant according to claim 1.