JPH05155835A - New cationic compound, its production and surfactant composed of the compound - Google Patents

Abstract

PURPOSE:To provide a new cationic compound usable as a surfactant for body washing base as well as hair-shampooing base because of its excellent surface- activity, frothing tendency and detergency and low irritation to the skin. CONSTITUTION:The cationic compound of formula I (R<1> is straight or branched- chain 7-15C alkyl or alkenyl; R<2> to R<4> are 1-3C alkyl; G and E are H or 1-3C alkyl or hydroxyalkyl; E may be group of formula II; E is not alkyl or hydroxyalkyl when G is alkyl or hydroxyalkyl; Y is H or OH; A is OH, halogen or 1-4C alkylsulfate group; (m) is 2 or 3; (n) is integer of 0-5; Y is H when (n) is not 1), e.g. the compound of formula III. The compound can be produced e.g. by reacting a compound of formula IV or V (G<1> and G<2> are groups/described in G provided that at least one of the groups is H) with a cationizing agent of formula VI or VII (Z is halogen).

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel cationic compound and a method for producing the same. More specifically, the present invention relates to a cationic compound having a mild action on the skin and having excellent foaming power and excellent detergency, which is useful as a hair or body cleansing surfactant and a method for producing the same.

[0002]

2. Description of the Related Art In recent years,
Surfactants used for detergents and the like are required to have excellent properties such as biodegradability, safety, and low irritation to eyes and skin, in addition to the surfactant ability. As surfactants that meet these requirements, acylated amino acid type surfactants and imidazoline type surfactants have been widely used. However, while these surfactants are generally excellent in safety and the like, they are inferior in foaming power and detergency, which are particularly important as surfactant ability, and therefore, they cannot be used alone as a component of shampoo or the like. However, it is generally used in combination with an anionic surfactant such as alkyl ether sulfate or alkyl sulfate.

Since such anionic surfactants are highly irritating to the skin, they may damage the skin. On the other hand, with regard to cationic active agents, a base material that is generally highly irritating to the skin, has a foaming power and is excellent in safety has not yet been found, and there is no case where it is applied as a detergent.
Therefore, the emergence of a cationic activator having excellent foaming power and detergency and high safety is strongly desired. If such a cationic activator is present, it is expected that a new detergent or a completely new application will be created by making use of its cationic characteristic.

[0004]

In view of the above situation, the present inventors have excellent cleaning power and foaming power for cleaning hair and body,
As a result of intensive studies on compounds having high safety, they have found that the novel cation compound represented by the following general formula (1) meets the object of the present invention, and completed the present invention. That is, the present invention provides a cationic compound represented by the general formula (1) and a surfactant comprising the cationic compound.

[0005]

[Chemical 9]

[Wherein R ^{1 is a} straight or branched chain having 7 to 7 carbon atoms]
15 represents an alkyl group or an alkenyl group. ^{R 2, R 3, R 4} : the same or different alkyl group having 1 to 3 carbon atoms. G: H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. E: H, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or a formula

[0007]

[Chemical 10]

A group represented by However, when G is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group,
E is not an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. Y: shows H or a hydroxy group. A: OH, a halogen atom or an alkylsulfate group having 1 to 4 carbon atoms. m: Indicates the number of 2 or 3. n: 0 or an integer of 1 to 5 is shown. However, when n = 1, Y = H or a hydroxy group is shown, and n = 0, 2, 3,
In the case of 4 and 5, Y = H is shown. The present invention will be described in detail below. The general formula (1)
The reports on the cationic compounds represented by
Such a cationic compound of the present invention, which is not disclosed in patent publications, is novel. Examples of these cationic compounds are as follows.

[0009]

[Chemical 11]

The cation of the present invention represented by the above general formula (1)
Compounds are produced by the following two production methods <1> or <2>.
Can be built.Manufacturing method <1>  The cationic compound represented by the general formula (1) of the present invention
Is the general formula (2)

[0011]

[Chemical 12]

[In the formula, R ¹ , G and m have the above-mentioned meanings. ] The cyclic amine represented by the general formula (3)

[0013]

[Chemical 13]

[In the formula, R ¹ and m have the above-mentioned meanings. G ¹ ,
G ² represents H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, and at least one of G ¹ and G ² is
H. ] Amidoamine represented by the following (hereinafter referred to as a starting amine compound) and a compound represented by the general formula (4)

[0015]

[Chemical 14]

[In the formula, R ² , R ³ , R ⁴ , Y, A, and n have the above-mentioned meanings. Z represents a halogen atom. ] The cationizing agent represented by the formula [4] is obtained by reacting the cationizing agent (4) in an amount of 1 to 3 moles with respect to the starting amine compound. The present manufacturing method is specifically described as follows.

[0017]

[Chemical 15]

[In the above series of formulas, R ¹ , R ² , R ³ , R ⁴ , G, G
¹ , G ² , E, Y, A, m, n and Z have the above-mentioned meanings. ] The reaction between the starting amine compound and the cationizing agent (4) is usually carried out by adding the cationizing agent (4) to the alcohol solution of the starting amine compound.
It is preferable to maintain the pH at 7 to 12 after dropping the aqueous solution of (1), and therefore, an alkaline solution such as sodium hydroxide or potassium hydroxide is charged into the reaction solution if necessary. During the reaction, the pH of the reaction system is maintained within the above range in order to react the starting amine compound with the cationizing agent (4). From the viewpoint of reaction rate, it is preferable that the pH is 7 or more, and if the pH exceeds 12, the cationizing agent (4) causes hydrolysis, which is not preferable. The reaction proceeds even at room temperature, but the higher the temperature, the faster the reaction. However, if the temperature and pH are high, the hydrolysis of the cationizing agent (4) is promoted, and therefore the temperature is 100 ° C or lower, preferably 90 ° C or lower. In the present production method, the molar ratio of the cationizing agent (4) to the starting amine compound is usually preferably 1/1 to 3/1 and more preferably 1.1 / 1 to 1.5 / 1. When the amount of cationizing agent (4) is less than this range, the reaction rate decreases, and when the amount of cationizing agent (4) is more than this range, cationizing agent (4)
Alternatively, a large amount of the hydrolyzate of the cationizing agent (4) remains in the reaction mixture, which is not preferable. The end point of the reaction between the starting amine compound and the cationizing agent (4) can be confirmed by analyzing the remaining amount of the starting amine compound during the reaction using high performance liquid chromatography. The reaction solution in the present production method may be either an aqueous solution or a mixed solution of an aqueous solution and a lower alcohol such as ethanol or isopropyl alcohol, or a diol such as 1,3-propanediol or propylene glycol.

In this production method, the starting amine compounds used are cyclic amine (2) and amidoamine.
(3) is obtained by the following method. "Synthesis of cyclic amine (2)" General formula (6)

[0020]

[Chemical 16]

[In the formula, R ¹ has the above-mentioned meaning, and T 2 represents H or an alkyl group having 1 to 3 carbon atoms. And a fatty acid or an ester thereof represented by] shows the general formula _{(7) H 2 N (CH} 2) m NH-G (7) wherein, G, m are as defined above. ] The diamine represented by the formula (1) is reacted with a fatty acid or its ester (6) using 1 to 3 moles of the diamine (7) to give a cyclic amine.
(2) is obtained. The reaction is specifically as follows.

[0022]

[Chemical 17]

[In the series of formulas, R ¹ , T, G and m have the above-mentioned meanings. The reaction between the fatty acid or its ester (6) and the diamine (7) is carried out by heating under reduced pressure, and dehydration or de-lower alcohol (TOH; T represents the above meaning) to give the cyclic amine (2). To synthesize.

[Synthesis of Amidoamine (3)] Cyclic amine
(2) is hydrolyzed under acidic or alkaline conditions, or a fatty acid or its ester (6) is reacted with a diamine (7), and the resulting cyclic amine (2) is further hydrolyzed without isolation. By doing so, amidoamine (3) can be obtained. The reaction is specifically as follows.

[0025]

[Chemical 18]

[In the series of formulas, R¹, G, G¹, G², T, m is the front
Indicates the meaning of the description. ]Manufacturing method <2>  In the cationic compound (1) of the present invention, n = 1 and Y
Is a hydroxy group and is represented by the general formula (1-1).
The cation compound is a raw material amine compound (cyclic amine (2)
And / or amidoamine (3)) and the general formula (5)

[0027]

[Chemical 19]

[In the formula, R ² , R ³ , R ⁴ and A have the above-mentioned meanings. ] The cationizing agent represented by
It is obtained by reacting (5) with 1 to 3 moles of the starting amine compound. The present manufacturing method is specifically described as follows.

[0029]

[Chemical 20]

[In the series of formulas, R ¹ , R ² , R ³ , R ⁴ , G, G ¹ , G
² , E, A and m have the above meanings. ] In the reaction between the cationizing agent (5) and the starting amine compound, the molar ratio of the cation compound (5) and the starting amine compound is 1/1 to 3/1. When the molar ratio is below this range, If the reactivity decreases and the molar ratio exceeds this range, a large amount of the hydrolyzate of the cationizing agent (5) remains in the reaction mixture, which is not preferable. The reaction temperature is 30 to 12
The temperature is 0 ° C, preferably 50 to 90 ° C. When the reaction temperature is lower than this range, the reaction rate is slow, and when it exceeds this range, coloring or the like occurs, which is not preferable. In the reaction between the starting amine compound and the cationizing agent (5), in order to secure the reactivity and allow a certain reaction to proceed, it is preferable to charge an appropriate amount of an alkaline aqueous solution and maintain the pH at 7-12. .. If the pH is below this range, the reaction rate will be slow, and if it is above this range, a large amount of by-products will be produced and the yield will be reduced.

The method of synthesizing the starting amine compound in the present production method <2> is as described in the production method <1>. The reaction of the present invention may be carried out in air or in an inert gas atmosphere, but an inert gas atmosphere is preferred in terms of coloring and the like.

Examples of the fatty acid represented by the general formula (6) or the ester thereof used in the present invention include octyl acid, capric acid, lauric acid, myristic acid, palmitic acid, coconut fatty acid and the like or lower alcohol ester thereof. Examples of the diamine represented by the general formula (7) include ethylenediamine and N-methylethylenediamine N.
-Ethylethylenediamine, N-isopropylethylenediamine, aminoethylethanolamine, N- (2-
Hydroxypropyl) ethylenediamine, N- (3-hydroxypropyl) ethylenediamine, N-methyltrimethylenediamine, N-ethyltrimethylenediamine,
Examples thereof include N-propyltrimethylene diamine.

The above-mentioned cationic compound obtained by the present invention has a surface activity and is used as a surfactant.
In particular, a surfactant composed of a mixture of the following (a) and (b) cationic compounds, or a mixture of the following (a) and (b) cationic compounds further mixed with the following (c) cationic compounds: Activators are preferably used. (a) A cationic compound represented by the general formula (1), in which G is H and E is H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. (b) In the general formula (1), G is H or has 1 to 3 carbon atoms.
Is an alkyl group or a hydroxyalkyl group of
Is the expression

[0034]

[Chemical 21]

A cation compound which is a group represented by [wherein R ² , R ³ , R ⁴ , Y, A and n have the above-mentioned meanings]. (c) A cation compound represented by the general formula (1), wherein G 1 is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, and E 2 is H 2.

[0036]

EXAMPLES Next, the present invention will be explained in detail based on examples, but the scope of the present invention is not limited thereby.

Example 1 268 g (1 mol) of 1-hydroxyethyl-2-undecylimidazoline synthesized by a conventional method in a 2-liter four-necked flask equipped with a stirrer, a cooling tube, a dropping funnel, and a thermometer. 54 g of water and 1.2 g of sodium hydroxide were charged and the temperature was raised to 80 ° C with stirring, and stirring was continued at the same temperature for about 2 hours to open the imidazoline ring to N-lauroyl-
N '-(2-hydroxyethyl) ethylenediamine was obtained. Next, 200 g of ethanol was charged and the temperature was raised to 80 ° C. with stirring. To measure the pH of this reaction product, a pH electrode was inserted into the solution, and a 40% NaOH aqueous solution was added dropwise so that the pH became 10. Then 3-chloro-2-hydroxypropyl-N, N, N
-489 g (1.3 mol) of a 50% aqueous solution of trimethylammonium chloride (MW188) was added dropwise over 2 hours. During this time
To maintain pH 10, 40% NaOH sodium hydroxide was added dropwise as appropriate. 3-chloro-2-hydroxypropyl-N, N,
After the completion of the dropwise addition of N-trimethylammonium chloride, stirring was continued at this temperature while maintaining pH 10 and the remaining N-lauroyl-N '-(2-hydroxyethyl) ethylenediamine was analyzed by high performance liquid chromatography every hour. The amount was confirmed. 6 hours after the addition of 3-chloro-2-hydroxypropyl-N, N, N-trimethylammonium chloride was completed, the in-system concentration of N-lauroyl-N '-(2-hydroxyethyl) ethylenediamine was reduced to 1% or less. It was confirmed that the reaction had ended, and the reaction was terminated. The reaction solution was purified by electrodialysis, partially evaporated to dryness, dissolved in ethanol, and analyzed by high performance liquid chromatography. The following three components were obtained as main components.

[0038]

[Chemical formula 22]

[0039]IR analysis, mass spectrometry results  <IR analysis> 1650 cm^-1 (6.06μ) shows strong absorption characteristic of amide
It was <Mass spectrometry> (The conditions for mass spectrometry are as follows.
It ) Device: JEOL Ltd. SX-102 type mass spectrometric measurement condition; Introduction method Direct ionization method FAB (Fast Atom Bomberdment) analysis result; Fragment ion molecular weight 402, 226 Two major peaks were observed, 402 is (M⁺−Cl) ion
And is a cationic compound with the above structure.
I confirmed.

[0040]

[Chemical formula 23]

[0041]IR analysis, mass spectrometry results  <IR analysis> 1650 cm^-1 (6.06μ) shows strong absorption characteristic of amide
It was <Mass Spectrometry> Analysis result; Fragment ion molecular weight 458, 270

[0042]

[Chemical formula 24]

[0043]IR analysis, mass spectrometry results  <IR analysis> 1650 cm^-1 (6.06μ) shows strong absorption characteristic of amide
It was <Mass Spectrometry> Analysis result; fragment ion molecular weight 402, 270 Example 2 1-hydro synthesized by using myristic acid as raw material fatty acid
1-Hydroxyethyl-2-tridecylimidazoline
Used in place of xyethyl-2-undecylimidazoline
The procedure of Example 1 was repeated, except that
That the main component is a three-component structure
It confirmed by the method similar to Example 1.

[0044]

[Chemical 25]

Example 3 The same procedure as in Example 1 was repeated except that 1-hydroxyethyl-2-pentadecylimidazoline synthesized by using palmitic acid as a raw material fatty acid was used instead of 1-hydroxyethyl-2-undecylimidazoline. It was confirmed in the same manner as in Example 1 that the obtained compound was mainly composed of three components having the following structures.

[0046]

[Chemical formula 26]

Example 4 N- (3-lauroylaminopropyl) propylamine synthesized by using N-propyl-1,3-trimethylenediamine as a starting diamine, and 3-chloropropyl-N, N, as a cationizing agent. The same procedure as in Example 1 was carried out except that N-trimethylammonium chloride was used, and it was confirmed in the same manner as in Example 1 that the obtained compound mainly contained three components having the following structures.

[0048]

[Chemical 27]

[0049]IR analysis, mass spectrometry results  <IR analysis> 1650 cm^-1 At (6.06μ), strong absorption peculiar to amide was confirmed.
Was messed up. <Mass Spectrometry> The same conditions as in Example 1 were used. Analysis results; Fragment ion molecular weight 398, 240 Two major peaks were observed, and 398 was (M⁺−Cl) ion
And is a cationic compound with the above structure.
I confirmed.

[0050]

[Chemical 28]

Example 5 As the cationizing agent, 2,3-oxypropyl-N, N, N-trimethylammonium chloride is used instead of 3-chloro-2-hydroxypropyl-N, N, N-trimethylammonium chloride. Except for the above, the conditions were the same as in Example 1, and it was confirmed in the same manner as in Example 1 that the obtained compound was the same as the three components shown in Example 1.

Example 6 A 2-liter 4-necked flask equipped with a stirrer, a condenser, a dropping funnel and a thermometer was charged with 50 parts of 3-chloro-2-hydroxypropyl-N, N, N-trimethylammonium chloride.
% Aqueous solution 752 g (2 mol) and water 800 g were charged and the temperature was raised to 70 ° C. While maintaining this temperature, 1-hydroxyethyl-2-undecylimidazoline 2 synthesized by a conventional method was used.
68 g (1 mol) was added dropwise over about 2 hours. To measure the pH of this reaction product, insert a pH electrode into the solution and add a 40% NaOH aqueous solution dropwise to adjust the pH to about 10.
Aged for time. During this time, to maintain the pH,
40% NaOH was appropriately added dropwise, and the remaining amount of N-lauroyl-N- (2-hydroxyethyl) -ethylenediamine was confirmed by high performance liquid chromatography every hour. After confirming that the concentration of N-lauroyl-N- (2-hydroxyethyl) -ethylenediamine in the system was 1% or less, the reaction was completed. The reaction solution was purified by electrodialysis, partially evaporated to dryness, dissolved in ethanol, and analyzed by high performance liquid chromatography. The following three components were obtained as main components.

[0053]

[Chemical 29]

Example 7 A 2-liter 4-necked flask equipped with a stirrer, a condenser, a dropping funnel and a thermometer was charged with 50 parts of 3-chloro-2-hydroxypropyl-N, N, N-trimethylammonium chloride.
% Aqueous solution 376 g (1 mol) and water 800 g were charged and the temperature was raised to 70 ° C. While maintaining this temperature, 1-hydroxyethyl-2-undecylimidazoline 2 synthesized by a conventional method was used.
68 g (1 mol) was added dropwise over about 2 hours. To measure the pH of this reaction product, insert a pH electrode into the solution and add a 40% NaOH aqueous solution dropwise to adjust the pH to about 10.
Aged for time. During this time, to maintain the pH,
40% NaOH was appropriately added dropwise, and the remaining amount of N-lauroyl-N- (2-hydroxyethyl) -ethylenediamine was confirmed by high performance liquid chromatography every hour. After confirming that the concentration of N-lauroyl-N- (2-hydroxyethyl) -ethylenediamine in the system was 1% or less, the reaction was completed. The reaction solution was purified by electrodialysis, then partially evaporated to dryness, and the compound N-lauroyl-N- (2-hydroxyethyl) -N'- having the structure shown in (c) below was analyzed by IR analysis and mass spectrometry. A three-component mixture based on [3- (N ", N", N "-trimethylammonio) -2-hydroxypropyl] -ethylenediamine chloride was obtained.

[0055]

[Chemical 30]

Test Example The active agents obtained in Examples 1 to 7 and the following Control Compounds 1 and 2 which are known to be extremely mild to the skin and Control Compound 3 which is excellent in foaming power. The skin irritation, foaming power and detergency were evaluated by the methods described below. The results are shown in Table 1. <Control compound 1> Kawaken Co., Ltd. softazoline CH (N-cocoyl-N'-hydroxyethyl-N'-sodium carboxymethylethylenediamine) <Control compound 2> Kawaken Co., Ltd. alanone ALE (N-lauroyl- N-Methyl-β-alanine sodium) <Control compound 3> Emal TD (sodium laurin sulfate) manufactured by Kao Co., Ltd. <Evaluation method> Skin irritation test A 24-hour closed patch test for humans was performed. That is, 20
A human test subject was impregnated with 0.1 ml of an aqueous solution containing 0.2% of a surfactant as an active ingredient, and a bandage plaster for batch test.
It was applied for 24 hours, and irritation was determined 24 hours after removal of the application. The judgment result was defined as positive by showing a clear erythema, and indicated by its positive rate.・ Foaming power test 4 ° so that the final concentration of the active ingredient in the surfactant is 0.2%.
It was diluted with DH hard water and measured by the inversion stirring method. The measurement was performed at 40 ° C. with the addition of 0.3% lanolin, and the results are shown in terms of foam volume (ml).・ Detergency test 5 cm x 5 cm wool muslin cloth with 2% carbon black
Dirt with almost the same composition as scalp oil containing (paraffin 12%,
Wax ester 21%, triglyceride 26%, higher fatty acid 32%, cholesterol 5%, monoglyceride 2
%) Is uniformly applied and dried. This contaminated cloth was placed in a stainless steel cylinder of about 1000 ml containing 500 ml of detergent containing 0.6% of active agent, pH 7.0 and 4 ° DH, and shaken for 6 minutes in a constant temperature bath at 40 ° C. After being thoroughly rinsed in running water, it is dried and the reflectance is measured. The cleaning rate is calculated by the following formula.

[0057]

[Equation 1]

[0058]

[Table 1]

[0059]

The cationic compound obtained by the method of the present invention has surface activity, and the surfactant containing such a compound as a main component is excellent in foaming power, detergency, and hypoallergenic, and therefore has hair. It can be used not only as a washing base but also as a body washing base.

─────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] September 17, 1991

[Procedure Amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0018

[Correction method] Change

[Correction content]

[In the above series of formulas, R ¹ , R ² , R ³ , R ⁴ , G, G
¹ , G ² , E, Y, A, m, n and Z have the above-mentioned meanings. ] The reaction between the starting amine compound and the cationizing agent (4) is usually carried out by adding the cationizing agent (4) to the alcohol solution of the starting amine compound.
It is preferable to maintain the pH at 7 to 12 after dropping the aqueous solution of (1), and therefore, an alkaline solution such as sodium hydroxide or potassium hydroxide is charged into the reaction solution if necessary. During the reaction, the pH of the reaction system is maintained within the above range in order to react the starting amine compound with the cationizing agent (4). From the viewpoint of reaction rate, it is preferable that the pH is 7 or more, and if the pH exceeds 12, the cationizing agent (4) causes hydrolysis, which is not preferable. The reaction proceeds even at room temperature, but the higher the temperature, the faster the reaction. However, if the temperature and pH are high, the hydrolysis of the cationizing agent (4) is promoted, and therefore the temperature is 100 ° C or lower, preferably 90 ° C or lower. In the present production method, the molar ratio of the cationizing agent (4) to the starting amine compound is usually preferably 1/1 to 3/1 and more preferably 1.1 / 1 to 2.1 / 1. When the amount of cationizing agent (4) is less than this range, the reaction rate decreases, and when the amount of cationizing agent (4) is more than this range, cationizing agent (4)
Alternatively, a large amount of the hydrolyzate of the cationizing agent (4) remains in the reaction mixture, which is not preferable. The end point of the reaction between the starting amine compound and the cationizing agent (4) can be confirmed by analyzing the remaining amount of the starting amine compound during the reaction using high performance liquid chromatography. The reaction solution in the present production method may be either an aqueous solution or a mixed solution of an aqueous solution and a lower alcohol such as ethanol or isopropyl alcohol, or a diol such as 1,3-propanediol or propylene glycol.

[Procedure Amendment 2]

[Document name to be amended] Statement

[Name of item to be corrected] 0030

[Correction method] Change

[Correction content]

[In the series of formulas, R ¹ , R ² , R ³ , R ⁴ , G, G ¹ , G
² , E, A and m have the above meanings. In the reaction between the cationizing agent (5) and the starting amine compound, the molar ratio of the cation compound (5) to the starting amine compound is 1/1 to 3/1 . When the molar ratio is below this range, the reactivity is lowered, and when the molar ratio exceeds this range, a large amount of the hydrolyzate of the cationizing agent (5) remains in the reaction mixture, which is not preferable. The reaction temperature is 30 to 12
The temperature is 0 ° C, preferably 50 to 90 ° C. When the reaction temperature is lower than this range, the reaction rate is slow, and when it exceeds this range, coloring or the like occurs, which is not preferable. In the reaction between the starting amine compound and the cationizing agent (5), in order to secure the reactivity and allow a certain reaction to proceed, it is preferable to charge an appropriate amount of an alkaline aqueous solution and maintain the pH at 7-12. .. If the pH is below this range, the reaction rate will be slow, and if it is above this range, a large amount of by-products will be produced and the yield will be reduced.

[Procedure 3]

[Document name to be amended] Statement

[Name of item to be corrected] 0037

[Correction method] Change

[Correction content]

Example 1 268 g (1 mol) of 1-hydroxyethyl-2-undecylimidazoline synthesized by a conventional method in a 2-liter four-necked flask equipped with a stirrer, a cooling tube, a dropping funnel, and a thermometer. 54 g of water and 1.2 g of sodium hydroxide were charged and the temperature was raised to 80 ° C with stirring, and stirring was continued at the same temperature for about 2 hours to open the imidazoline ring to N-lauroyl-
N '-(2-hydroxyethyl) ethylenediamine was obtained. Next, 200 g of ethanol was charged and the temperature was raised to 80 ° C. with stirring. To measure the pH of this reaction product, a pH electrode was inserted into the solution, and a 40% NaOH aqueous solution was added dropwise so that the pH became 10. Then 3-chloro-2-hydroxypropyl-N, N, N
-489 g (1.3 mol) of a 50% aqueous solution of trimethylammonium chloride (MW188) was added dropwise over 2 hours. During this time
To maintain pH 10, 40% NaOH sodium hydroxide was added dropwise as appropriate. 3-chloro-2-hydroxypropyl-N, N,
After the completion of the dropwise addition of N-trimethylammonium chloride, stirring was continued at this temperature while maintaining pH 10 and the remaining N-lauroyl-N '-(2-hydroxyethyl) ethylenediamine was analyzed by high performance liquid chromatography every hour. The amount was confirmed. 6 hours after the addition of 3-chloro-2-hydroxypropyl-N, N, N-trimethylammonium chloride was completed, the concentration of N-lauroyl-N '-(2-hydroxyethyl) ethylenediamine in the system was 0.1 %.
After confirming the following, the reaction was terminated. The reaction solution was purified by electrodialysis, partially evaporated to dryness, dissolved in ethanol, and analyzed by high performance liquid chromatography. The following three components were obtained as main components.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI technical display location C11D 1/62

Claims (6)

[Claims] 1. A cationic compound represented by the general formula (1). [Chemical 1] [In the formula, R ^{1 represents a} linear or branched alkyl group or alkenyl group having 7 to 15 carbon atoms. ^{R 2, R 3, R 4} : the same or different alkyl group having 1 to 3 carbon atoms. G: H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. E: H, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, or a compound represented by the formula: Represents a group represented by. However, when G is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, E is 1 carbon atom
It is not an alkyl group or a hydroxyalkyl group of ~ 3. Y: shows H or a hydroxy group. A: OH, a halogen atom or an alkylsulfate group having 1 to 4 carbon atoms. m: Indicates the number of 2 or 3. n: 0 or an integer of 1 to 5 is shown. However, when n = 1, Y = H or a hydroxy group is shown, and n = 0, 2, 3,
In the case of 4 and 5, Y = H is shown. ] 2. The general formula (2): [In the formula, R ¹ , G and m have the above-mentioned meanings. ] And / or the general formula (3) [In the formula, R ¹ and m have the above-mentioned meanings. G ¹ and G ² represent H ² or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, and at least one of G ¹ and G ² is H ² . ]
And an amidoamine represented by the general formula (4): [In the formula, R ² , R ³ , R ⁴ , Y, A, and n have the above-mentioned meanings.
Z represents a halogen atom. ] The method for producing a cation compound represented by the above general formula (1), which comprises reacting with a cationizing agent represented by the formula [1]. 3. A cyclic amine represented by the general formula (2) and / or an amidoamine represented by the general formula (3), and a general formula (5): [In the formula, R ² , R ³ , R ⁴ , and A have the above-mentioned meanings. ] Reacting with a cationizing agent represented by,
A method for producing a cationic compound represented by the general formula (1-1), wherein n = 1 in the general formula (1) and Y = hydroxy group. [Chemical 7] [In the formula, R ¹ , R ² , R ³ , R ⁴ , G, E, A, and m are as defined above. ] 4. A surfactant comprising a cationic compound represented by the general formula (1) according to claim 1. 5. A surfactant comprising a mixture of the following cationic compounds (a) and (b). (a) A cationic compound represented by the general formula (1), in which G is H and E is H or an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group. (b) In the general formula (1), G is H or has 1 to 3 carbon atoms.
Is an alkyl group or a hydroxyalkyl group of
Is the formula A cation compound which is a group represented by the formula: [wherein R ² , R ³ , R ⁴ , Y, A, and n are as defined above]. 6. The mixture according to claim 5, further comprising:
A surfactant obtained by mixing the cationic compound (c). (c) A cation compound represented by the general formula (1), wherein G 1 is an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group, and E 2 is H 2.