JPH05310661A - Production of di-long-chain type tertiary amine acid salt - Google Patents

Abstract

PURPOSE:To readily produce an aqueous dispersion off-chain type tertiary amine acid salt, having a uniform degree of neutralization and excellent in preservation stability with saved energy without causing a rapid rise in liquid viscosity in neutralizing. CONSTITUTION:The method for producing a di-long-chain type tertiary amine acid salt is characterized by mixing a reactional solution of a di-long-chain type tertiary amine compound having one group R-COO (R is 11-21C alkyl or alkenyl) derived from a 12-22C fatty acid, one group CONH and one 11-22C alkyl or alkenyl group in the molecule, e.g. a compound of formula I to III (R<1> is 1-4C alkyl or hydroxyalkyl; R<2> and R<3> are R; R<4> is 12-22C alkyl or alkenyl) with an acid in a field of a high shearing force in and/or after the neutralizing reaction thereof in subjecting the di-long-chain type tertiary amine compound and the acid to the neutralizing reaction in the presence of an emulsifying agent or a solvent and producing an aqueous dispersion of the objective di-long-chain type tertiary amine acid salt.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a process for producing a dilong-chain type tertiary amine acid salt which is a softening agent base useful as a softening agent for clothing. More specifically, when the base is produced, by mixing in a high shearing force field, the dispersion is made into fine particles, has a uniform degree of neutralization, and has excellent stability over a long period of time. The present invention relates to a method for producing an aqueous dispersion of an amine salt.

[0002]

2. Description of the Related Art Softening agents for clothing contain a softener base as a main component, but in order to improve the ease of use and efficiently impart performance,
It is known that it is necessary to make the softener base a stable aqueous dispersion. Therefore, conventionally, a stable aqueous dispersion has been obtained by dispersing it in warm water having a melting point of the softener base or higher in the presence of an emulsifier. For example, di (cured tallow alkyl) dimethylammonium chloride, which is a quaternary ammonium salt that is widely used as the main base of household softening agents currently on the market, is made into an aqueous dispersion by the method described above. .. Since this compound is a quaternary ammonium salt, it does not undergo a chemical change when it is made into an aqueous dispersion, so there is no sudden increase in liquid viscosity, and there are no major problems in terms of production and equipment. I couldn't find it.

The present inventors have previously proposed a dilong-chain type tertiary amine acid salt as a softening agent capable of imparting sufficient flexibility and antistatic properties to various fibers and imparting excellent elasticity. The present invention has been found (Japanese Patent Application No. 2-221742), and an attempt was made to obtain an aqueous dispersion in the same manner as described above. However, when an aqueous dispersion is to be obtained using a di-long-chain type tertiary amine acid salt obtained by previously neutralizing the di-long-chain type tertiary amine compound with an acid, the obtained di-long-chain type tertiary amine compound is used. It has been found that the aqueous dispersion of the tertiary amine acid salt is inferior in stability during storage, and the method used for the above-mentioned quaternary ammonium salt cannot be directly applied.

Further, as a means for obtaining a stable aqueous dispersion of a di-long chain type tertiary amine acid salt, a non-aqueous component, a di-long chain type tertiary amine compound is completely melted in the presence of an emulsifier. It is conceivable that neutralization is carried out in a so-called O / W emulsion state in which it is dispersed in a continuous aqueous phase. However, in this system, as the degree of neutralization progresses, the viscosity remarkably increases and becomes a gel, so it takes a long time to obtain a uniform degree of neutralization, and stronger stirring force is required. Such,
There is a drawback that the manufacturing equipment is large and heavy. In addition, although the emulsifier-free aqueous dispersion does not show a significant increase in viscosity, it has problems that the particle size distribution of the dispersion becomes nonuniform and that oily and aqueous components are easily separated during storage. .. In order to solve these problems, an object of the present invention is to provide a dilong-chain type tertiary-class compound having a uniform degree of neutralization and excellent long-term storage stability without causing a rapid increase in liquid viscosity during neutralization. An object of the present invention is to provide a method for easily producing an aqueous dispersion of an amine salt in an energy-saving manner.

[0005]

[Means for Solving the Problems] The present inventors have made the dispersion fine particles by mixing the dispersion in the presence of an emulsifier or a solvent in a state of low viscosity in a high shearing force field to obtain a uniform dispersion. It has been found that an aqueous dispersion of a di-long-chain type tertiary amine salt having a high degree of neutralization and excellent long-term storage stability can be obtained, and at the same time, the liquid viscosity can be suppressed to a low level, which leads to energy saving in terms of dynamics. The present invention has been completed by conducting intensive research paying attention to such things. That is, the gist of the present invention is to provide one R-COO- group (R represents an alkyl group or alkenyl group having 11 to 21 carbon atoms) derived from a fatty acid having 12 to 22 carbon atoms in the molecule, -CONH- Base 1
And a dilong-chain type tertiary amine compound having one alkyl group or an alkenyl group having 11 to 22 carbon atoms and an acid are neutralized in the presence of an emulsifier or a solvent to form a di-long chain type tertiary amine. In producing an aqueous dispersion of an amine acid salt, the reaction solution is mixed in a high shearing force field during and / or after the neutralization reaction, to produce a di-long-chain type tertiary amine acid salt. Regarding the method.

The production method of the present invention comprises the above-mentioned di-long chain type third
A primary amine compound and an acid are neutralized to produce an aqueous dispersion of a di-long-chain tertiary amine salt. Here, as the di-long chain type tertiary amine compound, for example, a compound represented by the following (A-1), (A-2) or (A-3) can be used.

[0007]

[Chemical 2]

(Wherein R ¹ is an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, R ² and R ³ are the same or different and are alkyl groups or alkenyl groups having 11 to 21 carbon atoms, R ⁴ Represents an alkyl group or an alkenyl group having 12 to 22 carbon atoms, m is 2 or 3.) In the production method of the present invention, these compounds are single,
Alternatively, two or more kinds can be mixed and used.

The method for synthesizing the above compound is not particularly limited, and the compound can be synthesized according to the following method (Japanese Patent Application No. 2-221742). That is,
The compound represented by (A-1) is, for example, a compound represented by the following formula (AB-1) obtained by cyanoethylation and hydrogenation of dialkanolamines such as N-lower alkylalkanolamines and diethanolamine. Carbon number 12
It can be obtained by reacting with ~ 22 fatty acids.

[0010]

[Chemical 3] (In the formula, R ¹ and m have the same meanings as described above.)

The compound represented by the formula (A-2) is, for example, a compound represented by the following formula (AB-2) obtained by an intramolecular dehydration cyclization reaction of N-lower alkyldiethanolamine with an aliphatic amine. Can be obtained by reacting with a fatty acid halide having 12 to 22 carbon atoms and washing the obtained compound with an alkaline solution such as sodium hydroxide.

[0012]

[Chemical 4] (In the formula, R ¹ has the same meaning as described above.)

Further, the compound represented by (A-3) is, for example, a compound of the following formula (AB-) obtained by an intramolecular dehydration cyclization reaction of N-higher alkyl or alkenyl diethanolamine.
After reacting the compound represented by 3) with a lower alkylamine, it is reacted with a fatty acid halide having 12 to 22 carbon atoms,
It can be obtained by washing the obtained compound with an alkaline solution such as sodium hydroxide.

[0014]

[Chemical 5] (In the formula, R ⁴ has the same meaning as described above.)

As the acid used in the present invention, either an inorganic acid or an organic acid can be used. Examples of the inorganic acid include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and the like, and examples of the organic acid include acetic acid, Lactic acid, glycolic acid, citric acid,
Examples thereof include organic acids having 1 to 6 carbon atoms such as maleic acid. These acids can be used only as an acid component or as an aqueous solution. Further, it can be used as a single acid or as a mixed acid of two or more kinds. Of these, hydrochloric acid or sulfuric acid is preferable from the viewpoints of the cost of the acid, the stability of the obtained di-long-chain type tertiary amine acid salt, and the odor. In the present invention, the di-long chain type tertiary amine compound may not be completely neutralized, and the amount of the acid used is preferably 0.8 to 1.5 times the neutralization equivalent amount, It is preferably 1.0 to 1.3 times. 0.
When it is less than 8 times, the di-long chain type tertiary amine compound is hydrolyzed and the stability of the aqueous dispersion is lowered, which is not preferable. When it exceeds 1.5 times, the pH of the aqueous dispersion becomes extremely low, the stability thereof is lowered, and it is not preferable as a softening agent for clothing.

In the production method of the present invention, an emulsifier or a solvent is used at the time of neutralization in order to obtain a stable aqueous dispersion of a di-long-chain type tertiary amine acid salt. Here, the emulsifier is not particularly limited as long as it is a nonionic surfactant, and examples thereof include polyoxyethylene alkyl ether (ethylene oxide: 5 to 50 mol, carbon number of alkyl group: 12 to 12).
24), polyoxyethylene alkenyl ether (ethylene oxide: 5 to 50 mol, carbon number of alkenyl group: 12
To 24), polyoxyethylene alkylamine (ethylene oxide: 5 to 50 mol, carbon number of alkyl group: 12 to 2)
4), polyoxyethylene alkenylamine (ethylene oxide: 5 to 50 mol, carbon number of alkenyl group: 12 to 2)
4) etc. are mentioned. Further, a substance using propylene oxide instead of ethylene oxide of these compounds and a substance using a mixture of ethylene oxide and propylene oxide can be similarly suitably used. Further, polyhydric alcohols having 3 to 6 valences such as glycerin, trimethylolpropane, pentaerythritol and sorbitol, and lauric acid, oleic acid, stearic acid, hardened tallow fatty acid and the like having 8 to 8 carbon atoms.
It is possible to use an ester compound of 22 with a long chain fatty acid, or a compound obtained by adding 2 to 80 mol of ethylene oxide and / or propylene oxide to the hydroxyl group of the ester compound. Examples of the solvent include alcohols such as ethanol, isopropanol, propylene glycol and ethylene glycol. These may be used alone or in combination of two or more. The amount of the emulsifier or solvent added is usually 2 to 30 parts by weight, preferably 5 to 25 parts by weight, based on 100 parts by weight of the di-long chain type tertiary amine compound. When the amount is less than 2 parts by weight, the emulsification and dispersion effects or the stability of the di-long-chain type tertiary amine acid salt decrease, which is not preferable. On the other hand, even if added in an amount of more than 30 parts by weight, the effect is not improved, and on the contrary, the aqueous solution of the dispersion thickens, which causes a problem in liquidity during use, which is not preferable. The method of adding the emulsifier or the solvent is not particularly limited, and specific examples include the method described below. Further, either an emulsifier or a solvent may be used in the present invention, but both may be used in combination. The dispersion medium used in the present invention is usually water such as ion-exchanged water.

In the production method of the present invention, the above raw materials are used for the neutralization reaction, but the present invention is characterized in that the reaction liquid is mixed in the high shear force field during and / or after the neutralization reaction. And In the present invention, the high shear force field refers to a state in which a high shear force is applied so that the water-based dispersion is made into fine particles. Specifically, under the shearing force of the stirrer, the following equation φ = π · n (π is the circular constant, n is the rotation speed of the stirrer (1 /
Sec)), the shear rate (φ) is calculated to be 30 to 3000 (1 /
Second) is preferred. If it is less than 30 (1 / sec), the shearing force is small and the particle diameter of the aqueous dispersion of the di-long-chain type tertiary amine acid salt is large, resulting in poor storage stability.
If it exceeds 3000 (1 / sec), the equipment becomes heavy and the cost becomes high, which is not preferable. Such a high shear force field can be generated by a commercially available high-speed rotary mixer, for example, a mixing tank type Tokushu Kika Kogyo Co., Ltd. Ajihomo mixer or a line mixer type ( An Ebara Milder manufactured by Ebara Seisakusho Co., Ltd., a homomic line mill manufactured by Tokushu Kika Kogyo Co., Ltd., or a pipeline homomixer can be used.

The neutralization reaction between the di-long-chain type tertiary amine compound and the acid in the present invention follows a general amine / acid neutralization reaction, and the neutralization procedure is also a method of adding an acid. Alternatively, a method in which a solution containing an acid prepared in advance and a solution containing a dilong-chain type tertiary amine compound are simultaneously mixed may be used, and there is no particular limitation. Therefore, when mixing is performed in the high shearing force field during the neutralization reaction, the neutralization reaction can be specifically performed by the following various methods. The above emulsifier or solvent and the di-long chain type tertiary amine compound are dispersed in water, and an acid is added to the dispersion to mix them in a high shear field. A dispersion prepared by dispersing the above-mentioned emulsifier or solvent and a dilong-chain type tertiary amine compound in water and an acid are simultaneously charged into a container and mixed in a high shearing force field. The di-long chain type tertiary amine compound is added to an aqueous solution in which water is mixed with the above acid and an emulsifier or a solvent, and mixed in a high shear force field. Both an aqueous solution in which water is mixed with the above acid and an emulsifier or a solvent and a dilong-chain type tertiary amine compound are simultaneously charged into a container and mixed in a high shear force field. An aqueous solution prepared by mixing the above emulsifier or solvent with water, and the three components of the di-long chain type tertiary amine compound and the acid are simultaneously charged into a container and mixed in a high shear force field. Further, in the production method of the present invention, the reaction liquid may be mixed in a high shear force field after the neutralization reaction is performed as described above or after the neutralization reaction is performed without applying a high shear force field. .. Among these methods, a method of mixing in a high shearing force field during the neutralization reaction, or during the neutralization reaction and after the neutralization reaction is more preferable. In addition, before the neutralization reaction, the di-long chain type third group is added in the presence of an emulsifier or a solvent.
The aqueous dispersion of the primary amine compound may be mixed in advance in a high shear force field, and then further mixed in a high shear force field as described above.

By mixing an aqueous dispersion such as a reaction liquid in a high shearing force field as described above, the dispersion is made into fine particles, has a uniform degree of neutralization, and has a long-term storage stability and excellent long-term storage stability. An aqueous dispersion of a type tertiary amine acid salt can be easily and energy-savingly produced.

The neutralization reaction system may be either a batch system using a stirring tank, a continuous system such as a continuous stirring tank or a pipe line mixing, or a combination of the batch system and the continuous system. In addition, the mixing when a high shear force field is not applied can be performed with a stirrer, a static mixer, or the like used for ordinary mixing.

In the present invention, in order to prevent a rapid increase in viscosity and precipitation of the di-long-chain type tertiary amine compound and / or its salt, the neutralization reaction may be carried out while controlling the temperature within a specific temperature range. At that time, the temperature of the neutralization reaction is usually the melting point of the di-long-chain type tertiary amine compound or a temperature range of 25 ° C. lower than the melting point, preferably the temperature of 3 ° C. lower than the melting point or 15 ° C. lower than the melting point. Is. If the melting point is exceeded, a rapid increase in viscosity will occur and gelation will not be possible, and it will not be possible to obtain a uniform water-based dispersion, and the degree of neutralization will also be uneven, and a heavy stirrer and excessive power will be required. It is not preferable in terms of surface. On the other hand, when the temperature is lower than the melting point by 25 ° C., the di-long-chain type tertiary amine compound and / or the neutralized di-long-chain type tertiary amine acid salt is precipitated to obtain a stable aqueous dispersion. At the same time, the neutralization degree between the surface and the inside of the dispersion particles themselves becomes different, and it becomes difficult to obtain a uniform neutralization degree between the dispersion particles.

In the production method of the present invention, in order to prevent the occurrence of gelation and the like, the concentration of the obtained di-long-chain type tertiary amine acid salt in the aqueous dispersion is usually 5 to 30% by weight, preferably The amount of the raw material used may be adjusted so as to be 10 to 25% by weight. If the concentration is less than 5% by weight, the viscosity will not increase sharply during neutralization, but the productivity will decrease because it is a dilute solution. On the other hand, if it exceeds 30% by weight, gelation occurs during neutralization, and uniform neutralization is difficult, and it becomes difficult to obtain a more stable aqueous dispersion. Specifically, the amount of the di-long-chain type tertiary amine compound is mainly 5 parts by weight with respect to 100 parts by weight of water, although it may be slightly different depending on the amount of the emulsifier, solvent or acid used.
The concentration can be adjusted by adjusting the amount to 70 parts by weight.

[0023]

EXAMPLES The present invention will be described below with reference to Examples and the like.
The invention is in no way limited by these examples.

Synthesis Example 1 A method known from the adduct of N-methylethanolamine and acrylonitrile [J. Org. Chem. , 26 , 3
409, (1960)], N- (2-hydroxyethyl) -N-methyl-1,3-propylenediamine 66 g and hardened tallow fatty acid 284 g were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube. After charging, the temperature was raised to 180 ° C. It is heated at that temperature for about 10 hours while distilling off the produced water, and in the general formula (A-1), R ¹ is methyl, R ² and R ³ are hardened tallow fatty acid residues, and m is 2. Reaction product 3 containing di-long chain type tertiary amine compound as a main component
00g was obtained. The acid value, saponification value, hydroxyl group value, total amine value, and tertiary amine value of the obtained reaction product were measured, and the composition of the reaction product was examined. As a result, the di-long-chain type tertiary amine compound was found to be 8
6% by weight, mono-long-chain type tertiary amine was 10% by weight, and unreacted fatty acid was 4% by weight. The di-long chain type tertiary amine compound had a molecular weight of 644 and a melting point of 58 to 64 ° C.

Example 1 313 g of ion-exchanged water was added to a 500 ml tall beaker having an inner diameter of 73 mm and a stirring blade having a blade diameter of 35 mm, and the temperature was raised to 70 ° C. in a water bath capable of controlling temperature. Ethylene oxide:
19 mol addition) 12.0 g of lauryl ether and Synthesis Example 1
80.0 g of the di-long chain type tertiary amine compound obtained in (4) was added. After mixing and emulsifying at 70 ° C. with a stirring blade rotating at 500 rpm for 5 minutes, the stirrer was replaced with a homomixer M type manufactured by Tokushu Kika Kogyo Co., Ltd. and a high shearing force field (rotating speed 5000 rp).
13.0 g of a 35 wt% hydrochloric acid aqueous solution having a neutralization equivalent amount while cooling the liquid temperature while maintaining the temperature at 50 ° C.
The mixture was added over a period of 2 minutes for neutralization, and then stirring was continued for 2 minutes to obtain an aqueous dispersion containing 20% by weight of dilong-chain type tertiary amine acid salt. The maximum viscosity at the time of neutralization, the average particle size of the obtained aqueous dispersion of the di-long-chain type tertiary amine acid salt, and the degree of neutralization were measured, and the storage stability was tested. These physical properties were measured and quality was evaluated by the following methods.

(1) Maximum viscosity during neutralization (unit: CP) The load current value of the motor used for mixing and stirring is automatically measured, and the B-type viscometer measured value prepared using a standard solution prepared in advance and The maximum viscosity at the time of neutralization was determined from the calibration curve of the load current value of the motor for mixing and stirring. (2) Average particle size of dispersion (unit: nm) The average particle size of the dispersion was obtained by diluting an aqueous dispersion of a dilong-chain type tertiary amine acid salt with ion-exchanged water to a concentration of about 1% by weight. Was measured with a Coulter submicron particle analyzer (Coulter model N4). (3) Neutralization degree (unit:%) It was calculated from the amine value of the aqueous dispersion of the di-long-chain type tertiary amine acid salt by the following formula. Degree of neutralization (%) = (amine value before neutralization−amine value after neutralization) / amine value before neutralization × 100 (4) Storage stability Di-long chain type tertiary in a 100 cc sealed glass bottle. Add 50 g of aqueous dispersion of amine acid salt and store at 50 ° C. for 30 days,
Further, the appearance was evaluated for a product which was stored 10 times at −20 ° C. and room temperature repeatedly (24 hours / time). ○: No change in appearance. X: Changes in appearance and properties such as liquid phase separation, white turbidity and thickening are observed.

Examples 2 to 5 Dilong-chain type tertiary amine compounds shown in Table 1, acid, emulsifier,
Example 1 was repeated using a solvent at the neutralization temperature shown in Table 1.
An aqueous dispersion of a di-long chain type tertiary amine acid salt was obtained under the same operating conditions as above. Then, its physical properties and quality were evaluated in the same manner as in Example 1. Then, its physical properties and quality were evaluated in the same manner as in Example 1. The di-long chain type tertiary amine compound used in Example 2 was a compound represented by the following formula (AB-21).

[Chemical 6] Monostearylamine (CH ₃ (CH ₂ ) ₁₇ NH ₂ )
Is subjected to a ring-opening amidation reaction with lauric acid chloride (CH ₃ (CH ₂ ) ₁₀ COCl), and the obtained compound is washed with an aqueous sodium hydroxide solution. The di-long chain type tertiary amine compound used in Example 3 is a compound represented by the following formula (AB-3
1)

[Chemical 7] Is subjected to a ring-opening amidation reaction with monomethylamine (CH ₃ NH ₂ ) and then stearic acid chloride (CH ₃ (C
H ₂ ) ₁₆ COCl) and the obtained compound was washed with an aqueous solution of sodium hydroxide. The di-long chain type tertiary amine compound used in Examples 4 and 5 was the one obtained in Synthesis Example 1.

[0028]

[Table 1]

Example 6 313 g of ion-exchanged water was added to a 500 ml tall beaker having an inner diameter of 73 mm, and the temperature was controlled in a water bath 7.
After heating to 0 ° C., polyoxyethylene (ethylene oxide: 19 mol addition) lauryl ether 1 was used as an emulsifier.
2.0 g and 80.0 g of the di-long chain type tertiary amine compound obtained in Synthesis Example 1 were added. Tokushu Kika Kogyo Co., Ltd. at 70 ℃
After mixing and emulsifying for 5 minutes in a high shearing force field of rotation speed of 5000 rpm using a homomixer manufactured by M. Co., the mixture is cooled to 50 ° C., and then while maintaining the liquid temperature at 50 ° C., a neutralization equivalent amount of 35 wt% 13.0 g of a hydrochloric acid aqueous solution was added for 1 minute for neutralization, and then stirring was continued for 2 minutes to obtain an aqueous dispersion containing 20% by weight of di-long-chain type tertiary amine acid salt. Then, its physical properties and quality were evaluated in the same manner as in Example 1.

Example 7 157 kg of ion-exchanged water was charged into a 300-liter stirring tank having an inner diameter of 600 mm with a jacket, hot water of 80 ° C. was poured into the jacket to heat the inside of the stirring tank to 70 ° C., and polyoxyethylene (ethylene oxide: 19 mol addition)
6 kg of lauryl ether and 40 kg of the dilong-chain type tertiary amine compound obtained in Synthesis Example 1 were added. Blade diameter 200 mm
The aqueous dispersion of the di-long chain type tertiary amine compound kept at 70 ° C. with stirring at a rotation speed of 200 rpm using a 3-blade propeller blade of 0.1 m ² at a constant flow rate of 100 kg / Hr by a metering pump. Ebara Milder (MDN30) from Ebara Manufacturing Co., Ltd. while passing through a spiral heat exchanger.
3V: 6000 rpm) and a 35 wt% hydrochloric acid aqueous solution prepared in another container was used at a neutralization equivalent ratio of 16.2.
The Ebara Milder was quantitatively supplied in kg / Hr at the same time. At this time, a neutralization reaction was continuously carried out while maintaining the temperature of the neutralized product at the outlet of Ebara Milder at 50 ° C. to obtain an aqueous dispersion containing 20% by weight of dilong-chain type tertiary amine acid salt. Then, liquid properties and quality evaluation were performed in the same manner as in Example 1.

Comparative Example 1 313 g of ion-exchanged water was added to a 500 ml tall beaker having an inner diameter of 73 mm with a stirring blade having a blade diameter of 35 mm, and the temperature was raised to 70 ° C. in a water bath capable of controlling temperature, and then polyoxyethylene ( Ethylene oxide:
19 mol addition) 12.0 g of lauryl ether and Synthesis Example 1
80.0 g of the di-long chain type tertiary amine compound obtained in (4) was added. After mixing and emulsifying at 70 ° C. for 5 minutes at a rotation speed of a stirring blade of 500 rpm, 13.0 g of 35 wt% hydrochloric acid aqueous solution, which is a neutralization equivalent amount, was added for 1 minute while keeping the liquid temperature at 70 ° C. to neutralize. Then, stirring was continued for 2 minutes to obtain an aqueous dispersion containing 20% by weight of di-long-chain type tertiary amine acid salt. Then, its physical properties and quality were evaluated in the same manner as in Example 1.

The physical properties and quality evaluation results obtained in the above Examples 1 to 7 and Comparative Example 1 are shown in Table 1 above together with the operating conditions.

As shown in the results in Table 1, in the production methods of the Examples in which the mixture was mixed in a high shearing force field, the maximum viscosity at the time of neutralization was small, the degree of neutralization of the obtained aqueous dispersion was high, and the storage was high. It was excellent in stability. On the other hand, in the production method of Comparative Example 1 in which mixing was not performed in a high shear force field, a uniform degree of neutralization was not obtained, and storage stability was poor.

[0034]

EFFECTS OF THE INVENTION According to the method for producing a di-long-chain type tertiary amine acid salt of the present invention, a uniform degree of neutralization and a long-term storage stability are achieved without causing a rapid increase in liquid viscosity during neutralization. A water-based dispersion of a di-long-chain type tertiary amine salt having excellent properties can be easily produced with energy saving.

Claims (6)

[Claims] 1. An R-COO- group (R represents an alkyl group or an alkenyl group having 11 to 21 carbon atoms) derived from a fatty acid having 12 to 22 carbon atoms in the molecule, -CONH
A di-long chain by neutralizing a di-long chain type tertiary amine compound having one group and one alkyl group or alkenyl group having 11 to 22 carbon atoms and an acid in the presence of an emulsifier or a solvent. Long-chain type tertiary amine characterized by mixing the reaction solution in a high shearing field during and / or after the neutralization reaction in the production of an aqueous dispersion of a type tertiary amine acid salt Method for producing acid salt. 2. A di-long chain type tertiary amine compound is at least one selected from the group consisting of compounds represented by the following general formulas (A-1), (A-2) and (A-3). The manufacturing method according to claim 1, wherein [Chemical 1] (In the formula, R ¹ is an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, R ² and R ³ are the same or different and are an alkyl group or an alkenyl group having 11 to 21 carbon atoms, and R ⁴ is a carbon number. It represents an alkyl group or an alkenyl group of 12 to 22. m is 2 or 3.) 3. A di-long chain type third emulsifier or solvent is added.
The production method according to claim 1, wherein the amount is 2 to 30 parts by weight with respect to 100 parts by weight of the primary amine compound. 4. An aqueous dispersion of a dilong chain type tertiary amine compound is mixed in a high shearing force field in the presence of an emulsifier or a solvent before the neutralization reaction. A method for producing the di-long-chain type tertiary amine acid salt described. 5. The production method according to claim 1, wherein the neutralization temperature is a melting point of the dilong-chain type tertiary amine compound or a temperature range lower than the melting point by 25 ° C. 6. The concentration of the produced di-long-chain type tertiary amine acid salt in the aqueous dispersion is 5 to 30% by weight.
5. The manufacturing method according to any one of 5.