JP2951730B2 - Novel betaine compound, method for producing the same, and surfactant containing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel betaine compound and a method for producing the same. More specifically, the present invention relates to a betaine compound which has a mild action on the skin and has excellent foaming and detergency, and is useful as a surfactant for washing hair or body and a method for producing the same.

[0002]

2. Description of the Related Art In recent years,
Surfactants used in detergents and the like are required to be excellent in various properties such as biodegradability, safety, and low irritation to eyes and skin in addition to surface activity. As surfactants satisfying these requirements, acylated amino acid surfactants and imidazoline surfactants have been widely used.

[0003] However, these surfactants are generally excellent in safety and the like, but are inferior in foaming power and detergency, which are particularly important as surfactant properties. It is rarely used in combination with an anionic surfactant such as alkyl ether sulfate and alkyl sulfate.

[0004] Since such anionic surfactants are highly irritating to the skin, they may damage the skin.

[0005] For this reason, there is a strong demand for an active agent which is excellent in foaming power and detergency and which is highly safe.

[0006]

Means for Solving the Problems In view of the above situation, the present inventors have excellent detergency and foaming power for hair and body washing,
As a result of intensive studies on a highly safe surfactant, the following general formula (1)

[0007]

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Wherein R ¹ is a linear or branched alkyl, alkenyl or hydroxyalkyl group having 8 to 22 carbon atoms, X is H or hydroxyl group, and R ² , R ³ and R ⁴ are carbon atoms. It has been found that the betaine compound represented by the formula (1) is an alkyl group of 1 to 4, and n is a number of 1 to 5. The present invention has been completed.

That is, the present invention provides a compound represented by the general formula (1)

[0010]

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(Wherein, R ¹ is a linear or branched alkyl, alkenyl or hydroxyalkyl group having 8 to 22 carbon atoms, X is H or a hydroxyl group, and R ² , R ³ and R ⁴ are carbon atoms. The present invention provides a novel betaine compound represented by the formula (1), wherein the alkyl group is 1 to 4, and n is a number of 1 to 5.), a process for producing the same, and a surfactant containing the same.

Hereinafter, the present invention will be described in detail.

There have been no reports on betaine compounds belonging to the above general formula (1), which have been reported in the prior art, patents and the like, and such betaine compounds are novel.

The betaine compound of the present invention can be produced by the following two production methods <1> and <2>.

[0015] Aliphatic represented by the production method <1> Amination R ¹ NH ₂ (R ¹ represents a linear or branched alkyl group having 8 to 22 carbon atoms, alkenyl group or hydroxyalkyl group.) The General formula for primary amine
(2)

[0016]

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Wherein Y is a halogen atom, X is H or a hydroxyl group, R ² , R ³ and R ⁴ are an alkyl group having 1 to ⁴ carbon atoms;
Z represents OH, a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. The compound represented by the general formula (3)

[0018]

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(Wherein R ¹ is a straight or branched chain having 8 carbon atoms)
To 22 alkyl groups, hydroxyalkyl groups, alkenyl groups, X is H or a hydroxyl group, and R ² , R ³ , and R ⁴ have 1 to 1 carbon atoms.
4, Z is OH, a halogen atom or a carbon number of 1 to
4 represents an alkyl sulfate group. Compound (3)
Is generated.

[0020] betainized then compound (3) and general formula (4) (Wherein, Y is a halogen atom, n is a number of 1 to 5, M is
H, lower alkyl group and alkali metal. The compound (1) can be easily produced by reacting the halogenated lower alkylene carboxylic acid represented by the formula (1) or an ester or metal salt thereof in an amount of 1 to 3 moles with respect to the compound (3). it can.

The above reaction examples are specifically described as follows.

[0022]

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(In the formula, R ¹ , X, and n have the same meanings as above.) The reaction between the primary amine and the compound (2) is usually carried out by adding the primary amine dropwise to an aqueous solution of the compound (2) and then adjusting the pH. Is preferably maintained at 8 to 12, and for this purpose, an alkali solution such as sodium hydroxide or potassium hydroxide is charged into the reaction solution as necessary. During the reaction, the pH of the reaction system is maintained in the above range in order to react the primary amine with the compound (2). For this purpose, it is preferable to be on the alkaline side of pH 8 or more, but it is not preferable if the pH exceeds 12, since hydrolysis of the compound (2) occurs. The reaction proceeds at room temperature, but the higher the temperature, the faster the reaction. However, when the temperature and pH are high, the hydrolysis of compound (2) is promoted,
The temperature is 0 ° C. or lower, preferably 90 ° C. or lower.

In the production method <1>, the molar ratio of the compound (2) to the primary amine is usually 1/1 to 3/1,
Preferably it is 1.1 / 1 to 1.5 / 1. Molar ratio is 1/1
If the ratio is lower than the above, the reaction rate decreases, and if it exceeds 3/1, a large amount of the compound (2) remains in the reaction mixture, which is not preferable.

The end point of the reaction between the primary amine and the compound (2) can be confirmed by analyzing the remaining amount of the primary amine in the reaction solution by using high performance liquid chromatography. Then, an aqueous solution of the compound represented by the general formula (4) prepared in advance is added dropwise to perform betaine formation. Then, the alkaline aqueous solution described above is pH
The mixture is charged so as to have a pH of 8 to 12, preferably 9 to 11, while maintaining the temperature at 50 to 100 ° C, preferably 70 to 90 ° C. When the temperature is 50 ° C. or lower, the rate of betaine formation is slow, and when the temperature is 100 ° C. or higher, hydrolysis of the compound represented by the general formula (4) is promoted.

In the method of the present invention, the molar ratio of the halogenated lower alkylene carboxylic acid or its ester or alkali metal salt (4) to the betaine precursor compound (3) is as follows:
Usually 1/1 to 1/3, preferably 1.1 / 1 to 1.5
/ 1.

Primary amine and compound in the method of the present invention
The reaction time with (2) depends on the applied temperature and pH, but generally requires 1 to 12 hours. The reaction time in the latter stage also varies depending on the applied temperature and pH, but generally requires 1 to 12 hours.

The reaction solution in the method of the present invention is an aqueous solution,
Alternatively, a mixed solution of water and a lower alcohol such as ethanol or isopropyl alcohol, or a diol such as 1,3-propanediol or propylene glycol may be used.

Production method <2> Amination The primary amine used in production method <1> and general formula (5)

[0030]

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(Wherein R ² , R ³ , and R ^{4 each} have 1 to 4 carbon atoms)
Z is OH, a halogen atom or C 1-4
Represents an alkyl sulfate group. ) To react with the glycidyltrialkylammonium salt represented by the general formula (3)

[0032]

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(Wherein, R ¹ is a linear or branched alkyl group having 8 to 22 carbon atoms, a hydroxyalkyl group or an alkenyl group, R ² , R ³ , and R ⁴ are alkyl groups having 1 to ⁴ carbon atoms; Z is O
H represents a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. ) Is obtained.

Next, betaine conversion is carried out under the same conditions as in production method <1> to obtain the desired betaine compound (1).

The present manufacturing method can be represented by a formula as follows.

[0036]

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(Wherein R ¹ and n have the same meanings as above.) In the reaction of the glycidyltrialkylammonium salt represented by the general formula (5) with a primary amine, the reaction is represented by the general formula (5) The molar ratio of the compound to the primary amine is 1/1 to 3/1
It is. If the molar ratio is below this range, the reaction rate will decrease, and if the molar ratio exceeds this range, a large amount of the compound represented by the general formula (5) will remain in the reaction mixture, which is not preferable. The reaction temperature is 50 to 120 ° C, preferably 60 to 100 ° C. When the reaction temperature is lower than this range, the reaction rate is low, and when the reaction temperature is higher than this range, coloring or the like occurs, which is not preferable.

In the reaction of the primary amine with the glycidyltrialkylammonium salt (5), an appropriate amount of an aqueous alkali solution is charged and the pH is adjusted to 8 to 12 in order to secure the reactivity and promote a certain reaction. Is preferably maintained. When the pH is below this range, the reaction proceeds slowly, and when it exceeds this range, by-products are formed and the yield decreases.

The conditions for betaine formation in the production method <2> are as described in the production method <1>.

The reactions of the present invention described above as the production methods <1> and <2> may all be carried out in air or in an inert gas atmosphere. It is preferable to carry out in a gas atmosphere.

The primary amine R ¹ NH ₂ used in the present invention
(R ¹ has the above meaning), for example, octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, behenylamine, isostearylamine,
And coconut aliphatic amines.

Further, among the compounds represented by the general formula (1), those having n = 2 (compounds represented by the general formula (1 ′) or (1 ″)) are further described below. Manufacturing method <3>
May also be applied.

Production method <3> General formula (1 ')

[0044]

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(Wherein, R ¹ is a straight-chain or branched-chain carbon number of 8 to
22 alkyl groups, alkenyl groups or hydroxyalkyl groups, X is H or a hydroxyl group, R ² , R ³ and R ⁴ have 1 to 1 carbon atoms
4 represents an alkyl group. ) Or general formula (1 '')

[0046]

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(Wherein R ¹ , R ² , R ³ , and R ⁴ have the same meanings as described above). The betaine compound represented by the general formula (6) is obtained from a primary amine and acrylonitrile. (Wherein R ¹ represents a straight-chain or branched-chain alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) (cyanoethylation), and then the compound (6 ) Can be manufactured by four different routes.

Next, these specific manufacturing methods will be described below.

<Cyanoethylation> R ¹ NH ₂ (R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms.)
Acrylonitrile is reacted at a temperature of 30 to 80 ° C. in the presence of a polar solvent such as water or ethanol or isopropyl alcohol at a temperature of 30 to 80 ° C. with respect to an aliphatic primary amine represented by Equation (6) The compound shown by is produced. This compound (6)
The compound represented by the general formula (1 ′) can be produced by the following four routes.

<Route 1> Next, the compound (6) is reacted with the general formula (2)

[0051]

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(Wherein, R ² , R ³ , R ⁴ , X, Y and Z have the same meanings as above) in the presence of a dehydrohalogenating agent using 1 to 3 moles of the compound To the general formula (7)

[0053]

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(Wherein R ¹ , R ² , R ³ , R ⁴ , X and Z have the same meanings as described above), and then hydrolyzes in the presence of a basic compound. Thus, the betaine compound (1 ′) can be easily produced.

<Route 2> Compound (6) is represented by the general formula (9)

[0056]

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(In the formula, Y represents the above-mentioned meaning).
Reaction at a temperature of ~ 80 ° C, general formula (12)

[0058]

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(Wherein R ¹ and Y have the same meanings as above) to produce a compound represented by the general formula (11) with respect to the compound (12).

[0060]

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(In the formula, R ² , R ³ and R ⁴ have the same meanings as described above.)
Is reacted at a temperature of 80 ° C. to 130 ° C. using 1 to 5 moles of a trialkylamine (11) represented by the formula (1), and then hydrolyzed in the presence of a basic compound to easily form a betaine compound ( 1 '') can be manufactured.

<Route 3> The compound (6) is hydrolyzed in the presence of a basic compound to obtain a compound of the general formula (8) (Wherein R ¹ and M have the same meanings as above), and then a compound represented by the general formula (9)

[0063]

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(Wherein, Y represents the above-mentioned meaning).
Reaction at a temperature of 80 ° C.

[0065]

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(Wherein R ¹ , Y and M have the same meanings as above) to produce a compound represented by the formula (1), wherein the trialkylamine (11) is added 1 to 5 times with respect to the compound (10). 80 ° C using mol
By reacting at a temperature of up to 130 ° C., the betaine compound (1 ″) can be easily produced.

<Route 4> The compound (6) is hydrolyzed in the presence of a basic compound to give a compound of the general formula (8) (Wherein R ¹ and M have the same meanings as above), and then a compound represented by the general formula (2)

[0068]

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(Wherein, R ² , R ³ , R ⁴ , X, Y and Z have the same meanings as above) in the presence of a dehydrohalogenating agent using 1 to 3 moles of the compound The betaine compound (1 ′) can be easily produced by reacting

The above formula (1) obtained by the method of the present invention
The betaine compound has surface activity, and a surfactant containing such a compound as a main component has excellent foaming power, detergency, and low irritation. It can also serve as a cleaning base.

[0071]

Next, the present invention will be described in detail with reference to examples, but the scope of the present invention is not limited by these examples.

Example 1 Amination (Synthesis of Compound (3)) A 2-liter volume equipped with a stirrer, a condenser, a thermometer, and a dropping funnel.
A four-necked flask was charged with 185 g of dodecylamine (MW 185), 200 g of ion-exchanged water, and 100 g of ethanol. Thereafter, the mixture was heated to 75 ° C. while stirring. Next, while maintaining the above temperature, insert the pH electrode into the solution,
A 40% aqueous sodium hydroxide solution was added dropwise to adjust the pH to 10. Next, 489 g of a 50% aqueous solution of 3-chloro-2-hydroxypropyltrimethylammonium chloride (MW 188) was added to 2
Dropped in time. During this time, 40% sodium hydroxide was appropriately added dropwise to maintain the pH at 10. After dropping of 3-chloro-2-hydroxypropyltrimethylammonium chloride was completed, heating and stirring were continued while maintaining pH 10, and the remaining amount of dodecylamine was confirmed every hour by high performance liquid chromatography. Six hours after the completion of dropping of 3-chloro-2-hydroxypropyltrimethylammonium chloride, the concentration of dodecylamine in the system became 1%, and the process proceeded to the next step, betaine formation.

Betainin (Synthesis of Compound (1)) Then, after heating the above mixture to 80 ° C., a 40% aqueous solution of sodium monochloroacetate (MW 116.5) prepared in advance was prepared.
g was added dropwise over 2 hours. 40% to maintain pH10 during this time
An alkali aqueous solution was appropriately added dropwise. Maintain pH10, warm,
While continuing the stirring, the reaction was carried out by high performance liquid chromatography until the concentration of compound (3) in the system became 1%, and the reaction was terminated. After the reaction solution was purified using an electrodialysis apparatus, a part thereof was evaporated to dryness, and the compound of the formula (1) N-dodecyl-N- (3
-Trimethylammonio-2-hydroxypropyl) aminoacetate was confirmed to be obtained. Table 1 shows the results of test examples of the foaming power, detergency, and skin irritation of the obtained compounds.

Results of IR Analysis and Mass Spectrometry <IR Analysis> At 1590 cm ⁻¹ (6.25 μ), strong absorption characteristic of carboxylate ions was observed.

<Mass Spectrometry>Apparatus; SX-102, manufactured by JEOL Co., Ltd. Mass spectrometry type Measurement conditions; Introducing method Direct; Ionization method FAB (Fast Atom Bombardment) analysis result; Molecular weight of fragment ion 359 300 256 Main peak Three were observed, and 359 was the parent ion peak of (M + 1), confirming that the compound had the structure of the betaine compound of the present invention.

Example 2 The same procedures as in Example 1 were carried out except that tetradecylamine was used as the starting amine, and the results of a test of the foaming power, detergency and skin irritation of the obtained compound were compared with those of Example 1. With the first
It is shown in the table.

Example 3 The same procedure as in Example 1 was carried out except that 3-chloropropyltrimethylammonium chloride was used as a raw material. Table 1 shows the results of the test examples of the foaming power, detergency, and skin irritation of the obtained compounds together with the results of Example 1.

Results of IR analysis and mass spectrometry <IR analysis> At 1570 cm ⁻¹ (6.45 μ), strong absorption characteristic of carboxylate ions was observed. <Mass Spectrometry> The analysis was performed under the same conditions as in Example 1. A parent ion peak of 343 (M + 1) was observed, confirming that the compound was the betaine compound of the present invention.

Example 4 (Synthesis of betaine compound (1 ′); route 1) <Cyanoethylation> A reactor similar to that in Example 1 was charged with 185 g of dodecylamine (MW 185) and 10 g of ethanol. Thereafter, the mixture was heated to 50 ° C. with stirring.
Next, 53 g of acrylonitrile (MW 53) was added dropwise over 1 hour, the mixture was aged for 2 hours, and the concentration of dodecylamine in the system was measured by gas chromatography to find that it was 0.3%.
Therefore, it proceeded to the next step. <Quaternization> Next, after heating the above mixture to 80 ° C., 200 g of ethanol, 50 g of ion-exchanged water, and 3-chloro-2-hydroxypropyltrimethylammonium chloride were added.
489 g (MW 188) of a 50% aqueous solution was added dropwise over 2 hours. During this period, 40% sodium hydroxide was appropriately added dropwise to maintain pH9. While maintaining pH 9 and continuing to heat and stir, the reaction was continued by high performance liquid chromatography until the in-system concentration of N- (2-cyanoethyl) -N-dodecylamine became 1% or less. <Hydrolysis> Next, in order to carry out hydrolysis of the cyano group, the reaction temperature was lowered to 75 ° C., and then the pH was set to 11 by appropriately adding 40% sodium hydroxide, and the reaction was carried out for 6 hours. rear,
The reaction was completed. After the reaction solution was purified by electrodialysis, a part thereof was evaporated to dryness, and the compound of the formula (1 ′), N-dodecyl-N- (3-trimethylammonio-) was analyzed by IR analysis and mass spectrometry. It was confirmed that (2-hydroxypropyl) aminopropionate was obtained. Table 1 shows the results of test examples of the foaming power, detergency, and skin irritation of the obtained compounds.

IR analysis and mass spectrometry <IR analysis> At 1560 cm ⁻¹ (6.4 μ), strong absorption characteristic of carboxylate ions was observed. <Mass spectrometry> Apparatus: JEOL Ltd. SX-102 type mass spectrometry Measurement conditions; Introduction method Direct; Ionization method FAB (Fast Atom Bombardment) Analysis result; Molecular weight of fragment ion 373 314 270 Three major peaks were recognized As a result, 373 was the parent ion peak of (M + 1), and this structure was confirmed.

Example 5 (Synthesis of betaine compound (1 ″); route 2) <Cyanoethylation> The same procedure as in Example 4 was carried out, and the next step was carried out. <Tertiary> Next, after heating the above mixture to 50 ° C., 92.5 g of epichlorohydrin (MW 92.5) was added dropwise over 2 hours. After the dropwise addition of epichlorohydrin, heating and stirring were continued, and N was performed every two hours by gas chromatography.
The remaining amount of-(2-cyanoethyl) -N-dodecylamine was confirmed. Eight hours after the completion of the dropwise addition of epichlorohydrin, the concentration of N- (2-cyanoethyl) -N-dodecylamine in the system became 1% or less, and the process proceeded to the next step, quaternization. <Quaternization> Next, after cooling the reaction mixture, the total amount was 2 l.
30% trimethylamine aqueous solution (MW 59) in autoclave
It was charged together with 197 g and 100 g of ethanol.

Thereafter, the mixture was stirred at 100 ° C.
And aged for 6 hours before cooling. <Hydrolysis> Next, the whole amount of the quaternized product was stirred with a stirrer,
The mixture was transferred to a 2-liter 4-neck flask equipped with a thermometer and a dropping funnel, and then heated to 80 ° C. Thereafter, the pH was set to 11 by appropriately adding 40% sodium hydroxide dropwise, and the reaction was carried out for 6 hours, followed by terminating the reaction.

After the reaction solution was purified by electrodialysis, a part was evaporated to dryness, and the compound of the above formula (1 ′), N-dodecyl-N- (3-trimethyl) was analyzed by IR analysis and mass spectrometry. It was confirmed that (ammonio-2-hydroxypropyl) aminopropionate was obtained.

Results of IR Analysis and Mass Spectrometry <IR Analysis> At 1560 cm ⁻¹ (6.4 μ), strong absorption characteristic of carboxylate ions was observed. <Mass spectrometry> Apparatus: JEOL Ltd. SX-102 type mass spectrometry Measurement conditions; Introducing method directly; Ionization method FAB (Fast Atom Bombardment) analysis result; Molecular weight of fragment ion 373 314 270 Three major peaks were recognized 373 was the parent ion peak of (M + 1), confirming the structure.

Example 6 (Synthesis of betaine compound (1 ′); route 4) <Cyanoethylation> The same procedure as in Example 4 was carried out and the next step was carried out.

<Hydrolysis> Next, after heating the above mixture to 70 ° C., 250 g of ethanol was charged, and when the temperature was restored to 70 ° C.
100 g of 40% sodium hydroxide was added dropwise over 1 hour, and the mixture was reacted for 7 hours to effect hydrolysis.

<Betaning> After heating the above mixture to 80 ° C.,
489 g (MW 188) of a 50% aqueous solution of 3-chloro-2-hydroxypropyltrimethylammonium chloride was added dropwise over 2 hours. During this time, 40% sodium hydroxide was added dropwise as appropriate to maintain the pH between 10-11. While maintaining the pH of 10 to 11, and continuing the heating and stirring, the concentration of lauroyl-β-alanine in the system was 1 by high performance liquid chromatography.
%. After the reaction solution was purified using electrodialysis, a part was evaporated to dryness, and subjected to IR analysis,
It was confirmed by mass spectrometry that the compound of the general formula (1 ′), N-dodecyl-N- (3-trimethylammonio-2-hydroxypropyl) aminopropionate, was obtained.

Comparative Example 1 As a surfactant, Softazoline CH (N-
Cocoyl-N'-hydroxyethyl-N'-sodium carboxymethylethylenediamine). Comparative Example 2 Alanone ALE (sodium N-lauroyl-N-methyl-β-alanine) manufactured by Kawaken Co., Ltd. was used as a surfactant. Comparative Example 3 Kao Corporation's Emar TD (triethanolamine lauryl sulfate) was used as a surfactant. In addition, as the compounds of Comparative Examples 1 and 2, those having conventionally very mild skin irritation were selected as controls.

(Test Examples) Test Method for Skin Irritation As a test method for skin irritation, a 24-hour closed sticking test was performed on humans. That is, a band test adhesive bandage impregnated with 0.1 ml of a 0.2% aqueous solution containing a surfactant as an effective component was applied to 20 subjects for 24 hours, and the irritation was evaluated 24 hours after the removal of the adhesive. As a result of determination, those showing clear erythema were defined as positive, and the positive rate was shown.・ Foaming power 4 ° so that the final concentration is 0.2% as a surfactant effective component
The sample was diluted with DH hard water and measured by an inverted stirring method. The measurement was carried out at 40 ° C. with the addition of 0.3% lanolin, and the results were shown in terms of foam volume (ml). -Detergency test 5% x 5cm wool muslin cloth with 2% carbon black
Soil of almost the same composition as scalp fat containing (paraffin 12%, wax ester 21%, triglyceride 26%, higher fatty acids
32%, cholesterol 5%, monoglyceride 2%) is applied uniformly and dried. Activator active ingredient
0.6%, pH 7.0, about 100 containing 500ml of detergent solution at 4 ° DH
The sample is placed in a 0 ml stainless steel cylinder, shaken in a constant temperature bath at 40 ° C. for 6 minutes, the contaminated cloth is thoroughly rinsed in running water, and after drying, the reflectance is measured. The cleaning rate is determined by the following equation.

[0090]

(Equation 1)

[0091]

[Table 1]

Claims (8)

(57) [Claims] [Claim 1] General formula (1) (Wherein, R ¹ is a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms, X is
H or a hydroxyl group; R ² , R ³ , and R ^{4 each} represent an alkyl group having 1 to ⁴ carbon atoms; A betaine compound represented by). 2. An aliphatic primary amine R ¹ NH ₂ (R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) and a general formula (2) Embedded image (Wherein, Y is a halogen atom, X is H or a hydroxyl group, R ² , R ³ and R ⁴ are an alkyl group having 1 to ⁴ carbon atoms, Z is OH, a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. Is reacted with a compound represented by the general formula (3). (Wherein R ¹ is a linear or branched alkyl group having 8 to 22 carbon atoms, a hydroxyalkyl group or an alkenyl group,
Represents H or a hydroxyl group, R ² , R ³ and R ⁴ represent an alkyl group having 1 to ⁴ carbon atoms, and Z represents OH, a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. ) To produce compound (3), and then compound (3) and general formula (4) (Wherein, Y is a halogen atom, n is a number of 1 to 5, M is
H represents a lower alkyl group or an alkali metal. 2. The process for producing a betaine compound according to claim 1, wherein the halogenated lower alkylene carboxylic acid represented by the formula (1) or a lower alkyl ester or an alkali metal salt thereof is reacted. 3. An aliphatic primary amine R ¹ NH ₂ (R ¹ represents a linear or branched alkyl, alkenyl or hydroxyalkyl group having 8 to 22 carbon atoms) and a general formula (5). Embedded image (Wherein, R ² , R ³ and R ⁴ are an alkyl group having 1 to ⁴ carbon atoms, and Z is O
H represents a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. ) To react with a glycidyltrialkylammonium salt represented by the general formula (3): Wherein X is a hydroxyl group, R ¹ is a linear or branched alkyl group having 8 to 22 carbon atoms, a hydroxyalkyl group or an alkenyl group, and R ² , R ³ and R ⁴ are alkyl groups having 1 to ⁴ carbon atoms. Group,
Z represents OH, a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. ) To produce compound (3), and then compound (3) and general formula (4) (Wherein, Y is a halogen atom, n is a number of 1 to 5, M is
H represents a lower alkyl group or an alkali metal. 2. The process for producing a betaine compound according to claim 1, wherein the halogenated lower alkylene carboxylic acid represented by the formula (1) or a lower alkyl ester or an alkali metal salt thereof is reacted. 4. An aliphatic primary amine R ¹ NH ₂ (R ¹ is a linear or branched alkyl, alkenyl or hydroxyalkyl group having 8 to 22 carbon atoms) and acrylonitrile. And the general formula (6) (Wherein, R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) to produce a compound (6), and then a compound (6) And general formula (2) (Wherein, Y is a halogen atom, X is H or a hydroxyl group, R ² , R ³ and R ⁴ are an alkyl group having 1 to ⁴ carbon atoms, Z is OH,
It represents a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. ) Is reacted to give a compound of the general formula (7) (In the formula, X represents H or a hydroxyl group, R ² , R ³ , and R ⁴ represent an alkyl group having 1 to ⁴ carbon atoms, and Z represents OH, a halogen atom, or an alkyl sulfate group having 1 to 4 carbon atoms.) A compound represented by the general formula (1 ') is obtained by obtaining a compound represented by the general formula (7) and hydrolyzing the compound represented by the general formula (7). (Wherein, R ¹ is a straight-chain or branched-chain alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms, X is H or a hydroxyl group, R ² , R ³ , and R ⁴ are C 1 to C 4 The method for producing a betaine compound represented by the formula: 5. An aliphatic primary amine R ¹ NH ₂ (R ¹ is a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) and acrylonitrile. And general formula (6) (Wherein R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) to produce a compound (6). General formula (8) after hydrolysis (R ¹ is a straight-chain or branched-chain alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms, and M is an alkali metal.) The compound represented by the general formula (2) Embedded image (Wherein, Y is a halogen atom, X is H or a hydroxyl group, R ² , R ³ and R ⁴ are an alkyl group having 1 to ⁴ carbon atoms, Z is OH, a halogen atom or an alkyl sulfate group having 1 to 4 carbon atoms. Wherein a compound represented by the general formula (1 ′) is reacted: (Wherein, R ¹ is a straight-chain or branched-chain alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms, X is H or a hydroxyl group, R ² , R ³ , and R ⁴ are C 1 to C 4 The method for producing a betaine compound represented by the formula: 6. An aliphatic primary amine R ¹ NH ₂ (R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) and acrylonitrile. And the general formula (6) (Wherein, R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) to produce a compound (6), and then a compound (6) To the general formula (8) (R ¹ is a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms, and M is an alkali metal.) After the compound represented by the general formula (9) Embedded image (Wherein Y is a halogen atom) by reacting with a compound represented by the general formula (10): Wherein R ¹ is a linear or branched alkyl, alkenyl, or hydroxyalkyl group having 8 to 22 carbon atoms, Y is a halogen atom, and M is an alkali metal. After the general formula (11) (Wherein R ² , R ³ , and R ⁴ represent an alkyl group having 1 to ⁴ carbon atoms), and reacted with a trialkylamine represented by the following general formula (1 ″): ] (In the formula, R ¹ is a linear or branched alkyl group having 8 to 22 carbon atoms, alkenyl group or hydroxyalkyl group, R ² , R ³ , R ⁴
Represents an alkyl group having 1 to 4 carbon atoms. )). 7. An aliphatic primary amine R ¹ NH ₂ (R ¹ is a linear or branched alkyl, alkenyl or hydroxyalkyl group having 8 to 22 carbon atoms) reacted with acrylonitrile. And the general formula (6) (Wherein, R ¹ represents a linear or branched alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms) to produce a compound (6) represented by the formula: General formula (9) (Wherein Y is a halogen atom) to react with a compound represented by the general formula (12): (Wherein R ¹ represents a straight-chain or branched-chain alkyl group, alkenyl group or hydroxyalkyl group having 8 to 22 carbon atoms), and after forming a compound represented by the general formula (11): ] (Wherein, R ² , R ³ , and R ⁴ each represent an alkyl group having 1 to ⁴ carbon atoms). '') (In the formula, R ¹ is a linear or branched alkyl group having 8 to 22 carbon atoms, alkenyl group or hydroxyalkyl group, R ² , R ³ , R ⁴
Represents an alkyl group having 1 to 4 carbon atoms. )). 8. A surfactant containing the betaine compound according to claim 1.