JPH08301829A - Neutralization of di-long-chain type tertiary amine and production of acid salt of di-long-chain type tertiary amine - Google Patents

Abstract

PURPOSE: To produce an acid salt of a di-long-chain type tertiary amine hardly deteriorating due to hydrolysis by gasifying water in an aqueous solution of an acid and uniformly neutralizing a di-long-chain type tertiary amine which is a softening base useful for a powdery softening and finishing agent for clothes in a molten state. CONSTITUTION: A di-long-chain type tertiary amine compound is converted into a molten state and water in an aqueous solution of an acid is gasified. In this state of the aqueous solution, both are mixed to carry out the neutralizing reaction in neutralizing the di-long-chain type tertiary amine compound with the aqueous solution of the acid. Water is then removed from the resultant neutralized substance to afford a powder of the acid salt of the long-chain tertiary amine.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for neutralizing a dilong chain type tertiary amine which is a softening agent base useful for a powder softening agent for clothing and a method for producing an amine acid salt thereof. More specifically, the present invention relates to a method for producing a powder of a di-long-chain type tertiary amine acid salt having a uniform degree of neutralization and excellent in suppressing hue and composition change in a series of production steps from the neutralization step to pulverization.

[0002]

2. Description of the Related Art Conventional methods for producing a compound such as a surfactant by a neutralization reaction are disclosed in, for example, JP-A-3-101828 and JP-A-61-216723. , A method for producing a high-concentration anionic surfactant by a high-concentration neutralization technique is disclosed, but all of them carry out the neutralization reaction in the presence of water or a solvent.

Further, Japanese Patent Laid-Open Nos. 5-310660 and 31 are also available.
No. 0663 discloses a method for obtaining a di-long chain type tertiary amine acid salt, for example, by melt-dispersing a di-long chain type tertiary amine compound in hot water having a melting point or higher, or in the presence of an emulsifier or the like. After being made into an O / W type emulsion, a neutralization reaction is carried out at a temperature below the boiling point of water while removing the heat of neutralization as necessary, and a di-long-chain type tertiary amine acid salt can be obtained. Is disclosed.

However, in these reaction systems, the viscosity increases remarkably as the degree of neutralization progresses, and therefore it takes time to obtain a uniform degree of neutralization, and therefore a di-long-chain type tertiary amine compound and There is a concern that the composition of the neutralized salt may change due to hydrolysis due to deterioration of the hue of the neutralized salt and neutralization in the presence of water, resulting in deterioration of flexibility and physical properties of the powder. Furthermore, in order to obtain a powdery di-long chain type tertiary amine acid salt from the obtained neutralized product, it is necessary to remove a large amount of water, and there was a concern in terms of quality deterioration and energy consumption. Further, in the above method, the concentration of the di-long chain type tertiary amine acid salt obtained was limited.

On the other hand, a method may be considered in which the di-long-chain type tertiary amine compound is melted in a stirring tank and then a solid acid or an aqueous acid solution is added to perform neutralization in a batch system. Due to the problem of viscosity, strong power and time are required to carry out a uniform neutralization reaction, and further, in an aqueous solution of an acid, hydrolysis by the entrained water proceeds. On the other hand, in the case of a solid acid, composition change due to hydrolysis does not occur, but since it is necessary to keep the operating temperature high in order to further lower the viscosity and perform sufficient mixing, there is a disadvantage that hue deterioration occurs during this period.

The salt obtained by such neutralization needs to be in a product form or powder form after neutralization, but in the above batch system, it takes a long time to transfer to the cooler in the next step. In addition, there is a problem that hue deterioration and composition change proceed during this time. Further, if the water of the acid aqueous solution is continuously supplied for a short time without being gasified to neutralize,
Since gasification of water occurs in the system (neutralization line), it has an effect of suppressing composition change due to hydrolysis, but is not sufficient, and there arises a problem that control of pressure and flow rate becomes difficult.

Further, when neutralizing by gas-liquid contact using a gas such as hydrogen chloride, it is useful because there is no composition change due to hydrolysis, but handling is difficult in view of safety and the cost is low. Is also a disadvantage.

The object of the present invention is to solve the above problems by gasifying water to carry out a uniform neutralization reaction.
An object of the present invention is to provide a method for producing a dilong-chain type tertiary amine acid salt having good powder properties without composition change and hue deterioration, and further, with a simple and compact equipment,
An object of the present invention is to provide a method for producing a powder soft base material with high productivity and energy efficiency.

[0009]

[Means for Solving the Problems] The present inventors have focused on the rate of neutralization reaction and the rate of composition change (hydrolysis), and have made a melted di-long-chain type tertiary amine compound and a solvent (water) in advance. The gasified acid aqueous solution is uniformly mixed for a short period of time to neutralize, then the solvent is removed and the mixture is cooled, so that the di-long-chain type tertiary amine acid salt can be obtained without increasing the pressure in the system. The present invention has been completed by conducting intensive research focusing on the fact that the above powder can be obtained.

That is, the gist of the present invention is (1) in neutralizing a dilong-chain type tertiary amine compound with an aqueous acid solution,
A method for neutralizing a di-long-chain type tertiary amine, characterized in that the amine compound is brought into a molten state, and in a state where water in the acid aqueous solution is gasified, both are subjected to a neutralization reaction, 2)
The neutralization method according to the above (1), wherein the mixing is continuously performed, and (3) the above (1) or (2) in which the neutralization reaction is performed in a state where the acid and water in the aqueous acid solution are gasified. (4) Neutralization method of di-long-chain type tertiary amine compound using an aqueous acid solution, wherein the amine compound is in a molten state and water in the aqueous acid solution is gasified. Then, the both are mixed to carry out a neutralization reaction, and water is removed from the obtained neutralized product to obtain a powder of a di-long-chain type tertiary amine acid salt. For producing primary amine acid salt, (5)
Water is removed from the neutralized product within a temperature range from the neutralization temperature to the melting point of the di-long chain type tertiary amine acid salt, and then cooled to obtain a powder of the di long chain type tertiary amine acid salt. (4) The production method according to (4), and (6) the production method according to (4) or (5), wherein the neutralization reaction is performed in a state where the acid and water in the aqueous acid solution are gasified. .

Hereinafter, the present invention will be described in detail. Examples of the di-long chain type tertiary amine compound used in the present invention include compounds represented by the following (A-1), (A-2) or (A-3).

[0012]

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(Wherein 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 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, and m is 2 or 3.)

In the production method of the present invention, these compounds may be used singly or as a mixture of two or more kinds.

The method for synthesizing the above compound is not particularly limited, and the compound can be synthesized according to the following method.

That is, the compound represented by (A-1) is represented by the following formula (AB-1) obtained by cyanoethylation and hydrogenation of dialkanolamines such as N-lower alkylalkanolamine and diethanolamine. It can be obtained by reacting the represented compound with a fatty acid having 12 to 22 carbon atoms.

[0017]

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

Further, 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, and an aliphatic amine. After a ring-opening amidation reaction with, a reaction with a fatty acid halide having 12 to 22 carbon atoms and washing the obtained compound with an alkaline solution such as sodium hydroxide can be obtained.

[0020]

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(In the formula, R ¹ has the same meaning as described above.)

Further, the compound represented by the formula (A-3) is, for example, a compound represented by the following formula (AB-3) obtained by a dehydration cyclization reaction of N-higher alkyl or alkenyldiethanolamine with a lower alkylamine. After reacting with
It 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.

[0023]

[Chemical 4]

(In the formula, R ⁴ has the same meaning as described above.)

As the aqueous acid solution used in the present invention, either an aqueous solution of an inorganic acid or an organic acid can be used.
Since most of the commercially available products are those in which the acid is dissolved in water, they can be used as they are. Examples of the aqueous solution of the inorganic acid include hydrochloric acid, sulfuric acid and phosphoric acid, and examples of the aqueous solution of the organic acid include organic acids such as acetic acid, glycolic acid, citric acid, succinic acid and lactic acid. Among these acids, hydrochloric acid or phosphoric acid is preferable from the viewpoints of cost of the acid and flexibility of the obtained powder of the di-long-chain type tertiary amine acid salt, physical properties of powder, hue and the like. These acid aqueous solutions can be used as a single acid or as a mixed acid of two or more kinds.

The amount of the acid used in the present invention is preferably 0.50 to 2.00 times, more preferably 0.75 to 1.50 times the neutralization equivalent amount. If it is less than 0.50 times, the softening performance is deteriorated, which is not preferable. Further, the concentration of the acid in the aqueous acid solution is preferably a high concentration from the viewpoint of production efficiency, treatment amount, etc., preferably 20% by weight or more, more preferably 30% by weight or more.

In the method for neutralizing a di-long-chain type tertiary amine of the present invention, when the above raw materials are used for the neutralization reaction, the amine compound is brought into a molten state and the water in the aqueous acid solution is gasified. It is characterized in that the two are mixed in a liquefied state to carry out a neutralization reaction, and as the method, both a continuous method and a batch method can be applied. However, the continuous method is industrially advantageous in terms of production efficiency, throughput, and the like. According to such a neutralization method, water that is a solvent can be gasified in advance and can be instantly and uniformly neutralized with the molten amine compound, so that the viscosity increases with the progress of the degree of neutralization. It is possible to suitably obtain a neutralized product while preventing the composition from changing due to hydrolysis.

In order to bring the amine compound into a molten state, the temperature of the amine compound may be set to the melting point or higher before or during the neutralization reaction, and the temperature for the neutralization reaction or the like may be set appropriately.

Therefore, the temperature of the neutralization reaction is usually in the temperature range from the melting point of the di-long chain type tertiary amine compound to the boiling point of the di-long chain type tertiary amine compound, preferably 1 from the melting point.
The temperature range is 5 ° C. higher or 20 ° C. lower than the boiling point, more preferably 30 ° C. higher than the melting point or 40 ° C. lower than the boiling point. If the boiling point of the di-long chain type tertiary amine compound is exceeded, decomposition will occur. on the other hand,
At a temperature lower than the melting point, the dilong-chain type tertiary amine compound or a neutralized product thereof solidifies and uniform mixing and neutralization with an acid cannot be performed, and it becomes difficult to obtain a target neutralized product.

In the present invention, the water in the acid aqueous solution is in a gasified state, but any device can be used as the gasification device as long as the water content can be sufficiently gasified. For example, heat exchangers such as plate type, spiral type, multi-tubular cylindrical type (shell & tube), and evaporators of direct fire heating type, steam heating multi-tubular type and the like can be used.

When the water in the acid aqueous solution is gasified, an acid having a low boiling point such as hydrochloric acid is also gasified, and in this case, the entire acid aqueous solution is gasified. On the other hand, with an acid having a high boiling point such as sulfuric acid, only water is gasified, but in any case, the effect of the present invention can be obtained. In particular, in the former case, the neutralization reaction is efficiently carried out, and it is industrially advantageous in terms of production efficiency, throughput, and the like. The gasified water is supplied to the neutralization line together with the acid and mixed with the di-long chain type tertiary amine compound to carry out the neutralization reaction.

The reactor used for the neutralization reaction may be a tubular reactor (PFR) capable of uniform mixing, or a single tank or multi-stage continuous stirred tank reactor (CSTR). Examples of the PFR include a static type such as a static mixer manufactured by Noritake Company, a high shear type such as a milder manufactured by Ebara Seisakusho, and a loop reactor having a circulation pump. Also, one tank or multi-stage C
As the STR, a known reaction tank having a stirrer can be used. In the neutralization reaction of the di-long-chain type tertiary amine compound and the acid, it is necessary to carry out uniform and micro stirring and mixing because the viscosity of the reaction solution becomes high and gelation easily occurs. In the above-mentioned PFR, the reaction solution does not stay and flows in a plug flow, and has a uniform and microscopic stirring and mixing function, and the continuous neutralization reaction of the present invention can be suitably progressed. In the CSTR, the continuous neutralization reaction can proceed in a steady state at a constant reaction rate defined by the average residence time determined by the reaction liquid volume in the reaction tank and the reaction raw material supply flow rate. In this case, CSTR
However, when the reactor is enlarged, the uniform and microscopic stirring and mixing function may be insufficient depending on the structures of the stirrer and the reaction tank, but in the neutralization reaction of the present invention, the viscosity becomes high in the middle stage of the reaction. Also, since gelation is likely to occur in the middle stage, the continuous neutralization reaction of the present invention can be suitably progressed by advancing the neutralization reaction in a steady state with a low viscosity and a reaction rate that makes gelation difficult. .

The residence time of the neutralization reaction is preferably 60 minutes or less, more preferably 30 minutes or less, particularly preferably 10 minutes.
It is less than one minute, and if it is more than 60 minutes, there is a risk of hue deterioration, which is not preferable. On the other hand, in the case of the batch system, a time longer than the above reaction time is required, depending on the scale and the like.

The method for producing the di-long chain type tertiary amine acid salt of the present invention is to remove water from the neutralized product obtained by the above-mentioned neutralization method to obtain the di-long chain type tertiary amine acid salt. It is characterized by obtaining a powder. In the present invention, from the viewpoint of increasing the efficiency of water removal, water is removed (dried) from the neutralized product within a temperature range from the neutralization temperature to the melting point of the dilong-chain type tertiary amine acid salt, and then cooled. Is preferably performed.

Further, the dryer and the cooler used for such drying and cooling are not particularly limited, and generally known devices are used. Examples of the dryer include a stirring thin film evaporator (Shinko Pantech Co., Ltd.), a vacuum evaporator, a current dryer (Okawara Manufacturing Co., Ltd.), a spray dryer (Okawara Kakoki Co., Ltd.), a loop dryer ((shares) ) Nara Machinery Co., Ltd.) is used. A belt or drum type cooler and a spray cooling tower can be used as the cooler, and among them, a spray cooler (Okawara Kakohki Co., Ltd.) that is capable of cooling and powdering is preferable.

The operating conditions for drying may be either normal pressure or reduced pressure (using a vacuum pump, for example), but it is preferable to carry out drying under reduced pressure from the viewpoint of efficiency of water removal. The water content contained in the powder obtained by cooling is preferably 5% by weight or less, more preferably 2% by weight or less, from the viewpoint of composition stability.

Further, in the present invention, a solubilizing agent can be used to improve the solubility of the powdery long-chain type tertiary amine acid salt in water when used as a powder softening agent. The dissolution aid 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 24), polyoxyethylene. Examples include ethylene alkenyl ether (ethylene oxide: 5 to 50 mol, carbon number of alkenyl group: 12 to 24), polyoxyethylene alkenylamine (ethylene oxide: 5 to 50 mol, carbon number of alkenyl group: 12 to 24) and the like. To be 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, a polyhydric alcohol having 3 to 6 valences such as glycerin, trimethylolpropane, pentaerythritol, and sorbitol,
Ester compounds with long-chain fatty acids having 8 to 22 carbon atoms such as lauric acid, oleic acid, stearic acid, and hardened beef tallow fatty acid;
Alternatively, a compound obtained by adding 2 to 80 mol of propylene oxide can be used.

Further, sodium carbonate, potassium carbonate,
Inorganic salts and inorganic substances such as sodium chloride and urea, organic acids and organic salts such as glycolic acid, fumaric acid, sodium paratoluenesulfonate, polyvinyl alcohol, carboxymethyl cellulose, sodium snow alginate,
Examples thereof include organic polymers such as sodium polyacrylate, hydrous magnesium silicate / lithium, bentonite, clay minerals such as silica, and the like. Among these, the organic acids partially overlap with those used in the neutralization reaction, but the solubility of the product may be improved by using an excess of the organic acid in the neutralization reaction. However, it is preferable to appropriately select a solubilizing agent that does not affect the acid used for neutralization.

In the present invention, one or a mixture of two or more selected from the above is used as a dissolution aid. The amount of the solubilizing agent added is usually preferably 1 to 100 parts by weight, more preferably 5 to 30 parts by weight, based on 100 parts by weight of the dilong-chain type tertiary amine acid salt. Even if the added amount exceeds 100 parts by weight, there is no corresponding dissolution promoting effect, and conversely, the amount of the dissolution aid with respect to the di-long-chain type tertiary amine acid salt becomes too large, which is a designing factor for the softening agent. Is not preferable, and if it is less than 1 part by weight, a sufficient effect cannot be obtained. The above solubilizing agents can be added either before or after the neutralization reaction.

[0040]

EXAMPLES The present invention will be described in more detail with reference to Synthesis Examples, Examples and Comparative Examples, but the present invention is not limited to these Examples.

Synthesis Example 1 A method known from the adduct of N-methylethanolamine and acrylonitrile (J. Org. Chem., 26 , 3409, (1960)).
66 g of N- (2-hydroxyethyl) -N-methyl-1,3-propylenediamine and 284 g of hardened beef tallow fatty acid synthesized in Step 2 were placed in a 4-neck flask equipped with a thermometer, a stirrer, and a trap, and heated to 180 ° C. did. Heated at that temperature for about 30 minutes. The pressure was 200 Torr. Next, the pressure was reduced to 50 Torr and heating was continued for 8 hours. As a result, in the general formula (A-1), R ¹ is methyl, R ² and R ³ are hardened beef tallow fatty acid residues, and a reaction containing a di-long chain type tertiary amine compound in which m is 2 as a main component Thing 30
0 g was obtained.

The acid value of the resulting reaction product (JIS K007
0 reference), saponification value (JIS K0070 reference), hydroxyl value (JIS K0070 reference), total amine value (AST
MD2073-66 reference) and tertiary amine value (AST
MD 2073-66 reference) and the composition of the reaction product was investigated, and as a result, the di-long-chain type tertiary amine compound was 86% by weight,
The mono-long-chain type tertiary amine was 12% by weight, and the unreacted fatty acid was 2% by weight. The di-long chain type tertiary amine compound has a molecular weight of 645, a melting point of 58 to 65 ° C., and a boiling point of 270.
Was ~ 278 ° C.

Example 1 A di-long-chain type tertiary amine compound obtained in Synthesis Example 1 heated to 130 ° C. and a 35 wt% aqueous solution of hydrochloric acid were added to a plate heat exchanger (manufactured by Hisaka Seisakusho Co., Ltd.). 13 in model UX-01)
Gasification was performed at 0 ° C., and the mixture was supplied to an Ebara Milder (model MDN306) manufactured by EBARA CORPORATION to neutralize the neutralization equivalent amount. At this time, the neutralization temperature was kept at 130 ° C. and the neutralization time (residence time) was 2 minutes.

Next, in order to remove the gasified water contained in the neutralized product, it is supplied to a spray dryer (L type) manufactured by Okawara Kakohki Co., Ltd. under a pressure of 50 to 100 Torr and 130 ° C. The mixture was dried at 1, and further cooled for supply to a spray cooler (CL type) manufactured by Okawara Kakoki Co., Ltd. to obtain a powder of dilong-chain type tertiary amine hydrochloride. Next, the acid value, saponification value, and 3 of the obtained di-long-chain type tertiary amine hydrochloride are obtained.
The primary amine value and water content (%) were measured, and the neutralization reaction rate and the hydrolysis rate were determined as follows. In addition, hue and flexibility were also evaluated.

(1) Neutralization reaction rate (%) and hydrolysis rate (%) The neutralization reaction rate (%) was determined by using a dilong-chain type tertiary amine acid salt as a solvent, It was measured from the amine value by the following formula. The hydrolysis rate (%) was calculated from the acid value and saponification value of the di-long-chain type tertiary amine hydrochloride prepared by using a solvent.

[0046]

[Equation 1]

(2) Hue The hue was evaluated by the Gardner color sequence method.

(3) Flexibility The flexibility was evaluated by the following test method. A commercially available cotton towel was repeatedly washed 5 times with a commercially available detergent attack (manufactured by Kao Co., Ltd.), and 1 g of the powdered softening agent (0.9 g of softening agent, 0.1 solubilizing agent) per 1 kg of the cotton towel.
It was used in a proportion of g, and stirred at 3.5 ° DH hard water, 25 ° C. and a bath ratio of 1/30 for 5 minutes. The above treated cloth was air-dried at room temperature and then left in a constant temperature and humidity room at 25 ° C. and 65% RH for 1 day. Commercially available softening agents (Humming 1
/ 3; manufactured by Kao Co., Ltd.), a pair of softness comparisons were performed using a cotton towel treated so that the softening base had the same treatment concentration, and the softness was evaluated according to the following evaluation criteria. +2 Softer than the control +1 Softer than the control 0 Same as the control -1 Softer than the control -2 Softer than the control

Example 2 The di-long-chain type tertiary amine compound obtained in Synthesis Example 1 heated to 150 ° C. and a solvent of 70% by weight glycolic acid aqueous solution were mixed with a spiral heat exchanger of Croce Co., Ltd. (Model 1V
Type gas mixer at 150 ° C, and a steam mixer (model SME manufactured by Noritake Co.
-20-5) was supplied to a loop reactor incorporating the same. At this time, the neutralization temperature was kept at 150 ° C. and the neutralization time (residence time) was 10 minutes. Next, in order to sufficiently remove the gasified water contained in the neutralized product, 50 to 100 Tor
The mixture was supplied to a stirring thin film evaporator (manufactured by Shinko Pantech Co., Ltd.) under the pressure of r and dried at 130 ° C. Then
The powder was supplied to a spray cooler (CL type) manufactured by Okawara Kakohki Co., Ltd., and cooled to obtain a powder of di-long-chain type tertiary amine glycolate. Then, physical properties were measured in the same manner as in Example 1.

Example 3 Using the same apparatus as in Example 1, the dilong-chain type third compound shown in Table 1 was used.
Neutralized with a primary amine compound and hydrochloric acid under the conditions shown in Table 1,
After dehydration (drying) and cooling, a powder of dilong-chain type tertiary amine hydrochloride was obtained. Then, physical properties were measured in the same manner as in Example 1. Incidentally, di-long-chain tertiary amine compound used in Example 3, the compound represented by the following formula (AB-21) monostearyl amine _{(CH 3 (CH 2) 17} NH 2) and ring-opening amide After the reaction, the lauric acid chloride (CH ₃ (CH
₂ ) It was obtained by reacting with ₁₀ COC1) and washing the obtained compound with an aqueous sodium hydroxide solution.

[0051]

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Comparative Example 1 The dilong-chain type tertiary amine compound obtained in Synthesis Example 1 heated to 130 ° C. and a 35 wt% hydrochloric acid aqueous solution (25 ° C.) were adjusted to a neutralization equivalent amount ( It was continuously supplied to and neutralized by a laboratory milder manufactured by Ebara Corporation. Neutralization temperature is 130
The neutralization time was kept at 2 ° C for 2 minutes. Next, in order to evaporate the water contained in the di-long-chain type tertiary amine hydrochloride, 50 to 50
It is supplied to a spray dryer (L type) manufactured by Okawara Kakoki Co., Ltd. under a pressure of 100 Torr, and for further cooling, a spray cooler (CL) manufactured by Okawara Kakoki Co., Ltd.
Type) to obtain a powder of dilong-chain type tertiary amine hydrochloride.

Comparative Example 2 The same procedure as in Comparative Example 1 was carried out with a neutralization time of 10 minutes to obtain a powder of dilong-chain type tertiary amine hydrochloride.

The above results are shown in Tables 1 and 2.

[0055]

[Table 1]

[0056]

[Table 2]

As shown by the results in Table 1, all of the examples according to the present invention have a low hydrolysis rate, and therefore have good flexibility when used as a softening agent base. On the other hand, in Comparative Examples 1 and 2 in which the acid was supplied in the form of an aqueous solution, the hydrolysis rate was high as shown in Table 2, and therefore the flexibility when used as a softener base was poor.

[0058]

INDUSTRIAL APPLICABILITY According to the method for neutralizing a di-long chain type tertiary amine and the method for producing a di-long chain type tertiary amine acid salt of the present invention, a uniform neutralization reaction can be carried out, composition change and It is possible to obtain a di-long-chain type tertiary amine acid salt having no deterioration in hue and having good powder properties. Furthermore, the manufacturing equipment can be made simple and compact, and the powder softening agent can be manufactured with high productivity and energy efficiency, and it has a wide range of applications in powder type softening agent products (powder type, tablet type, sheet type). Etc.) is possible.

Claims (6)

[Claims] 1. When neutralizing a di-long-chain type tertiary amine compound with an aqueous acid solution, the amine compound is brought into a molten state, and the water in the aqueous acid solution is gasified, and both are mixed. A method for neutralizing a di-long-chain type tertiary amine, which comprises performing a neutralization reaction by means of 2. The neutralization method according to claim 1, wherein the mixing is performed continuously. 3. The neutralization method according to claim 1, wherein the neutralization reaction is performed in a state where the acid and water in the aqueous acid solution are gasified. 4. When neutralizing a dilong-chain type tertiary amine compound with an aqueous acid solution, the amine compound is brought into a molten state and water in the aqueous acid solution is gasified, and both are mixed. And a neutralization reaction is performed to remove water from the obtained neutralized product to obtain a powder of a dilong-chain type tertiary amine acid salt. Production method. 5. Water is removed from the neutralized product within a temperature range from the neutralization temperature to the melting point of the di-long-chain type tertiary amine acid salt,
Then, the mixture is cooled to obtain a powder of a di-long-chain type tertiary amine acid salt, and the production method according to claim 4. 6. The production method according to claim 4, wherein the neutralization reaction is carried out in a state where the acid and water in the aqueous acid solution are gasified.