JP2005154370A - Alkoxylated amine and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an alkoxylated amine having large addition molar number of an alkylene oxide, having good color and smell and causing little deterioration of the color after the storage for a long period and provide a simple method for the production of the alkoxylated amine. <P>SOLUTION: The method for the production of an alkoxylated amine contains an addition reaction step to produce an alkylene oxide addition reaction product of an aliphatic amine by adding an alkylene oxide to an aliphatic amine in the presence of a metal oxide catalyst or an acid catalyst. The production process preferably further includes a step to add a lower alcohol or water to the addition reaction product and remove the added solvent by distillation under reduced pressure or in an inert gas stream. The invention further provides the alkoxylated amine produced by the alkoxylated amine production method. The difference of the hue of the product measured by Gardner method immediately after production from the hue measured after storing for 30 days at 45°C is preferably ≤1. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to an alkoxylated amine which is an alkylene oxide adduct of an aliphatic amine, particularly an alkoxylated amine having a large number of added alkylene oxides, good color tone and odor, and little deterioration in color tone when stored for a long period of time. And a simple manufacturing method thereof.

Alkali oxide alkylene oxide adducts are used as surfactants and their raw materials. Fields of application are surfactants, fiber dyeing aids, fiber softeners, bactericides, agricultural chemical spreaders, antistatic agents, etc. Wide range of household, industrial, agricultural and so on.
Alkoxylated amines, which are alkylene oxide adducts of aliphatic amines, generally add alkylene oxides to aliphatic amines in the presence of no catalyst or alkali catalysts such as alkali metal and alkaline earth metal hydroxides. However, the color tone and odor are poor. In particular, as the number of added moles of alkylene oxide increases, the coloration becomes more prominent, and the color tone further deteriorates when stored for a long period of time.

  In order to solve such a problem, as a method for preventing the coloring, a method of distilling and purifying a raw material amine (see Patent Document 1) and a method of using a specific catalyst in a process of producing the raw material amine (see Patent Document 2) are proposed. Has been.

  However, these methods are methods for obtaining an alkoxylated amine having a good color tone by carrying out a specific operation in the production process of the starting amine and improving the properties of the raw material amine. An apparatus and a new catalyst are required, and there is a problem that a complicated pretreatment must be performed by distillation at a high temperature or catalytic reaction.

  In addition, as other methods, a method of reacting at low temperature (see Patent Document 3), a method using an additive obtained by adding a base or an aqueous solution thereof as a raw material aliphatic amine (see Patent Document 4), aliphatic A method of aging at 180 to 280 ° C. for 1 to 20 hours after adding an alkylene oxide to an amine (see Patent Document 5), a method of performing an acid treatment when adding an alkylene oxide to an aliphatic amine (see Patent Document 6), A method in which an alkali metal borohydride is added and then distilled (see Patent Document 7) is known.

  However, all of these methods are complicated in operation, and the effect of improving the color tone is obtained only when the number of moles of alkylene oxide added is small, and the color tone improves as the number of moles added exceeds 2 moles. The effect is insufficient. In addition, the effect of odor deterioration and color tone deterioration when stored for a long period of time is insufficient, and when the reaction is carried out at a low temperature, a problem arises in terms of productivity due to the longer reaction time.

Japanese Patent Laid-Open No. 11-228509 JP 2000-319232 A Japanese Patent Publication No. 51-40052 Japanese Patent Laid-Open No. 11-158125 Japanese Patent Laid-Open No. 54-24807 US Pat. No. 2,422,503 US Pat. No. 3,207,790

  An object of the present invention is to solve the conventional problems and achieve the following objects. That is, the present invention provides an alkoxylated amine having a large number of moles of alkylene oxide added, good color tone and odor, and little deterioration of color tone when stored for a long period of time, and a simple method for producing the alkoxylated amine. For the purpose.

  As a result of intensive studies in view of the above problems, the present inventors have obtained the following knowledge. That is, when an alkylene oxide is added to an aliphatic amine, the color tone and odor of the resulting addition reaction product (alkoxylated amine) are improved by using either a metal oxide or an acid catalyst as a catalyst. It was found that even when stored for a period of time, deterioration of color tone is suppressed. Further, it has been found that by adding either a lower alcohol or water to the addition reaction product and distilling it off under reduced pressure or under an inert gas flow, a further excellent color tone deterioration improving effect can be obtained. The present invention has been completed.

The present invention is based on the above findings of the present inventors, and means for solving the above problems are as follows. That is,
<1> An alkoxyl comprising an addition reaction step of producing an alkylene oxide addition reaction product of an aliphatic amine by adding an alkylene oxide to an aliphatic amine in the presence of either a metal oxide catalyst or an acid catalyst. It is a manufacturing method of fluorinated amine. In the method for producing an alkoxylated amine according to <1>, in the addition reaction step, the alkylene oxide is added to the aliphatic amine to produce an alkylene oxide addition reaction product of an aliphatic amine. As described above, an alkoxylated amine having good color tone and odor is produced.
<2> The method according to <1>, further including a distillation step of adding any solvent of lower alcohol and water to the addition reaction product, and distilling off the solvent either under reduced pressure or under an inert gas flow. This is a method for producing an alkoxylated amine. In the method for producing an alkoxylated amine according to <2>, in the distillation step, any solvent of the lower alcohol and the water is added to the addition reaction product. The solvent is distilled off either under reduced pressure or under inert gas flow. As described above, an alkoxylated amine having a good color tone and odor and little deterioration in color tone when stored for a long period of time is produced.
<3> The method for producing an alkoxylated amine according to any one of <1> to <2>, wherein the metal oxide catalyst is an aluminum / magnesium composite metal oxide.
<4> The <3>, wherein the aluminum / magnesium composite metal oxide contains at least one metal selected from iron, nickel, chromium, manganese, titanium, boron, germanium, cerium, molybdenum, zinc, and zirconium. This is a method for producing an alkoxylated amine.
<5> The method for producing an alkoxylated amine according to any one of <1> to <2>, wherein the acid catalyst is at least one selected from a Lewis acid and a complex thereof, and a perhalogen acid and a salt thereof. It is.
<6> Any one of <1> to <5>, wherein the aliphatic amine is any one of an aliphatic primary amine and an aliphatic secondary amine having an aliphatic hydrocarbon group having 8 to 22 carbon atoms. This is a method for producing an alkoxylated amine.
<7> The method for producing an alkoxylated amine according to any one of <1> to <6>, wherein the added mole number of the alkylene oxide is 1 to 40 moles relative to the aliphatic amine.
<8> Hue value measured by the Gardner method immediately after the production, and a hue value measured after 30 days at 45 ° C., produced by the method for producing an alkoxylated amine according to any one of <1> to <7>. And an alkoxylated amine characterized by having a difference of 1 or less.

  According to the present invention, it is possible to solve conventional problems, efficiently obtain an alkoxylated amine having a large number of added alkylene oxides, good color tone and odor, and little deterioration in color tone when stored for a long period of time. Can do.

(Method for producing alkoxylated amine)
The method for producing an alkoxylated amine of the present invention includes an addition reaction step, preferably includes a distillation step, and further includes other steps as necessary.

<Addition reaction step>
The addition reaction step is a step of producing an alkylene oxide addition reaction product of an aliphatic amine by adding an alkylene oxide to an aliphatic amine in the presence of either a metal oxide catalyst or an acid catalyst.

-Catalyst-
In the method for producing the alkoxylated amine, either the metal oxide catalyst or the acid catalyst is used.

The metal oxide used as the metal oxide catalyst is not particularly limited as long as it has alkoxylation activity, and can be appropriately selected according to the purpose. Examples thereof include barium oxide and strontium oxide. Preferably mentioned.
As the metal oxide, a composite metal oxide can be used. For example, a magnesium / aluminum composite oxide is preferably used. Here, as for the atomic ratio of this magnesium and this aluminum, Al / (Mg + Al) is 0.1-0.7, for example, 0.3-0.6 are more preferable, 0.4-0. 5 is more preferable.

  The magnesium / aluminum composite oxide may further contain a third metal. The third metal is not particularly limited and may be appropriately selected depending on the purpose. Examples thereof include Fe, Ni, Cr, Mn, Ti, B, Ga, Ce, Mo, and Zr. Among these, Fe, Cr, and Mn are preferable, and Mn is more preferably used. These metals may be used individually by 1 type, and may use 2 or more types together. The content ratio of the third metal is an atomic ratio with respect to all the metals in the composite metal oxide, and is preferably 0.01 to 0.5, more preferably 0.05 to 0.3, 0.1 -0.2 is still more preferable.

  There is no restriction | limiting in particular as a preparation method of the said composite metal oxide, According to the objective, it can select suitably, For example, well-known methods, such as an impregnation method and a coprecipitation method, can be used. Specifically, it can be prepared by using the methods described in JP-A-8-268919, JP-A-2000-061304, JP-A-2001-23210, and JP-A-2001-314765.

  Examples of the acid used as the acid catalyst include Lewis acid or a complex thereof, perhalogen acid or a salt thereof, sulfuric acid or a salt thereof, phosphoric acid or a salt thereof, nitric acid or a salt thereof, and the like. Lewis acids or complexes thereof, perhalogen acids or salts thereof are preferably used.

Examples of the Lewis acid or complex thereof include boron trifluoride, boron trifluoride complex (boron trifluoride ether complex, boron trifluoride acetic acid complex, boron trifluoride phenol complex, etc.), aluminum chloride, bromide. Aluminum, zinc chloride, tin tetrachloride, antimony pentachloride, titanium tetrachloride, silicon tetrachloride, ferric chloride, ferric bromide, cobaltous chloride, zirconium chloride, boron oxide, acidic activated alumina, etc. Of these, boron trifluoride complexes are particularly preferably used.
Here, the metal for forming the salt is not particularly limited and may be appropriately selected depending on the purpose. For example, a metal other than an alkali metal is preferable, and a divalent metal and a trivalent metal are preferable. More preferred. Specifically, Mg, Ca, Sr, Ba, Zn, Co, Ni, Cu, and Al are preferable, Mg, Ca, Sr, Ba, Zn, and Al are more preferable, and Mg, Zn, and Al are still more preferable.

  The perhalogen acid and its salt are not particularly limited and may be appropriately selected depending on the intended purpose. Examples of the halogen to be used include chlorine, bromine and iodine. Among these, chlorine Are preferably used.

  The amount of the catalyst used is appropriately determined depending on the molar ratio of the aliphatic amine to the alkylene oxide to be subjected to the reaction, and is, for example, 0.001 to 20 mass with respect to 100 mass parts of the aliphatic amine. Part is preferable, 0.05 to 10 parts by mass is more preferable, and 0.1 to 5 parts by mass is still more preferable.

-Aliphatic amine-
Suitable examples of the aliphatic amine used in the present invention include aliphatic primary amines and aliphatic secondary amines having an aliphatic hydrocarbon group having 8 to 22 carbon atoms. Here, the aliphatic hydrocarbon group may be saturated or unsaturated.
Examples of the aliphatic primary amine and the aliphatic secondary amine include octylamine, decylamine, laurylamine, tetradecylamine, cetylamine, stearylamine, behenylamine, oleylamine, didecylamine, dilaurylamine, and ditetradecylamine. , Dicetylamine, distearylamine, dibehenylamine, laurylstearylamine, and the like. These may be used individually by 1 type, and 2 or more types may be mixed and used for them. Further, for example, aliphatic amines derived from animal oils such as beef tallow and vegetable oils such as coconut oil and palm oil can be used.

-Alkylene oxide-
Examples of the alkylene oxide include ethylene oxide, propylene oxide, and butylene oxide. Among these, ethylene oxide and propylene oxide are preferable, and ethylene oxide is more preferable.
The added mole number of the alkylene oxide is preferably 1 to 40 moles, more preferably 1 to 30 moles, and more preferably 2 to 15 moles with respect to any one mole of the aliphatic primary amine and the aliphatic secondary amine. Further preferred.

  The addition method is not particularly limited as long as the alkylene oxide addition product of the aliphatic amine can be produced by adding the alkylene oxide to the aliphatic amine, and is appropriately selected according to the purpose. The reaction can be carried out under ordinary alkylene oxide addition conditions. As temperature conditions in this addition, 80 to 200 degreeC is preferable and 120 to 180 degreeC is more preferable.

  Through the above steps, the alkylene oxide is added to the aliphatic amine to produce an alkylene oxide adduct of the aliphatic amine.

<Distillation step>
The distillation step is a step of adding either a lower alcohol or water solvent to the addition reaction product, and distilling off the solvent either under reduced pressure or under inert gas flow.

  Examples of the lower alcohol include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, and butanol. Among these, methyl alcohol and ethyl alcohol are preferably used.

The distillation of either the lower alcohol or the water is preferably performed under reduced pressure or under an inert gas flow.
As temperature conditions at the time of performing the said distillation, 20-100 degreeC is preferable and 40-90 degreeC is more preferable. When the temperature is lower than 20 ° C., the distillation takes time, and when the temperature exceeds 100 ° C., the odor of the alkoxylated amine is deteriorated.
As a pressure condition when performing the said distillation under the said pressure reduction, 100 mmHg or less is preferable and 20 mmHg or less is more preferable. If the pressure is high, the distillation requires a long time.
The flow rate of the inert gas when performing the distillation under the inert gas flow is preferably 0.1 L / L · min, and more preferably 1 L / L · min or more. If the flow rate is small, the distillation requires a long time.

  1-100 mass% is preferable with respect to the said addition reaction material, and, as for the usage-amount of the said lower alcohol or the said water, 2-50 mass% is more preferable. Note that any of the remaining lower alcohol and water may be added all at once, or may be added in several portions.

  Through the above steps, either the lower alcohol or the water solvent is added to the addition reaction product, and the solvent is distilled off either under reduced pressure or under inert gas flow.

<Other processes>
There is no restriction | limiting in particular as said other process, Although it can select suitably according to the objective, For example, a catalyst separation process etc. are mentioned suitably.
The catalyst separation step is a step of separating the catalyst from the addition reaction product obtained in the addition reaction step.
The catalyst separation step is not particularly limited as long as the catalyst can be separated from the addition reaction product obtained in the addition reaction step, and examples thereof include filtration, distillation, centrifugation, sedimentation separation, and the like. It is done. The catalyst separation step may be performed before the solvent is added in the distillation step, after the solvent is added, or after the distillation step.
Through the above steps, the catalyst is separated from the aliphatic amine alkylene oxide addition reaction product.

  According to the method for producing an alkoxylated amine of the present invention, it is possible to easily produce an alkoxylated amine having a large number of moles of alkylene oxide added and having good color tone and odor, and in particular, by performing a distillation step, An alkoxylated amine with little deterioration in color tone even when stored for a period can be produced.

(Alkoxylated amine)
The alkoxylated amine of the present invention is produced by the method for producing an alkoxylated amine of the present invention.

In the alkoxylated amine of the present invention, the difference between the hue value measured by the Gardner method immediately after production and the hue value measured after 30 days at 45 ° C. is preferably 1 or less.
Here, the hue value (Gardner color number) is measured by the method described in JIS K5400 4.1.2 method. In the measurement by this method, the color of the sample prepared based on the prescribed method is displayed by the color number of the color glass equal to the Gardner color number standard solution. That is, a sample is taken in a Gardner color number tube (a colorless transparent glass tube having an inner diameter of 10 mm and a depth of 110 mm), set in a Gardner-Heliga colorimeter, a colorimetric plate is rotated, and the color of the sample is measured by transmitted light. And read the number that appears in the window when they match.

  The alkoxylated amine of the present invention, if the difference between the Gardner color number immediately after the production of the alkoxylated amine and the Gardner color number measured after 30 days at 45 ° C. is 1 or less, even when stored for a long time, It is an alkoxylated amine with little deterioration in color tone.

  The alkoxylated amine not only has a good color tone immediately after production, but also suppresses the deterioration of the color tone when stored for a long period of time, so it can be used in any application field that uses a surfactant or the like using an alkoxylated amine. For example, it can be suitably used for various detergents using surfactants, fiber dyeing assistants, fiber softeners, bactericides, agricultural chemical spreaders, antistatic agents, etc. It is not limited.

  Examples of the present invention will be described below, but the present invention is not limited to these examples.

(Example 1)
-Production of alkoxylated amines-
-Preparation of catalyst-
_{2.5MgO · Al 2 O 3 · mH} 2 O consisting of aluminum hydroxide-magnesium having a chemical composition (manufactured by Kyowa Chemical, Kyowaad 300) 25 g for 3 hours calcined activated at 500 ° C. The, 17 g Al-Mg composite metal oxide of Product catalyst powder was obtained.

--Addition reaction process--
Laurylamine is used as an aliphatic amine, 300 g of the laurylamine and 1.2 g of the Al—Mg composite metal oxide catalyst powder (0.3 mass% to amine) are charged into an autoclave, and the autoclave is filled with nitrogen. After the replacement, the temperature was raised with stirring. Next, while maintaining the temperature at 160 ° C. and the pressure at 0.3 MPa, 357 g (equivalent to 5 mol addition) of ethylene oxide (EO) as an alkylene oxide was introduced into the autoclave to cause an addition reaction, Aged.

--- Catalyst separation process--
After the addition reaction and aging, the reaction solution was cooled to 80 ° C., and 3.8 g of activated clay and diatomaceous earth were added as filter aids, respectively, and the catalyst was filtered off to obtain an EO5 molar adduct of laurylamine.

(Example 2)
-Production of alkoxylated amines-
In Example 1, an alkoxylated amine was produced in the same manner as in Example 1 except that the catalyst was a composite metal oxide of Mg / Al / Mn.

-Preparation of catalyst-
A solution in which 68.03 g of magnesium nitrate hexahydrate, 47.69 g of aluminum nitrate nonahydrate and 24.33 g of manganese nitrate hexahydrate are dissolved in 450 g of deionized water, and 13.47 g of sodium carbonate are deionized water. The solution dissolved in 450 g was added dropwise to a catalyst preparation tank in which 1800 g of deionized water had been charged in advance over 1 hour while maintaining the pH at 9 and the temperature at 40 ° C. with 2N NaOH. After completion of dropping, the mixture was aged for 1 hour. Then, this was filtered, washed, washed with deionized water, and spray-dried to obtain 30 g of a composite metal hydroxide. The obtained composite metal hydroxide was fired at 800 ° C. for 3 hours in a nitrogen atmosphere to obtain a composite metal oxide of Mg / Al / Mn.

  Using the obtained Mg / Al / Mn composite metal oxide as a catalyst, an “addition reaction step” and a “catalyst separation step” were performed in the same manner as in Example 1 to obtain an EO5 molar adduct of laurylamine.

(Examples 3 to 6)
-Production of alkoxylated amines-
In Example 1, an alkoxylated amine was produced in the same manner as in Example 1 except that after the “catalyst separation step”, a “distillation step” was further performed.

  The “addition reaction step” and the “catalyst separation step” were performed in the same manner as in Example 1.

-Distillation step-
In Example 1, after the “catalyst separation step”, the additive solvent described in Table 1 was added, and the gas phase part of the obtained reaction solution was replaced with nitrogen gas. The solvent was distilled off by the solvent distillation method described in 1. to give an EO5 molar adduct of laurylamine.

(Example 7)
-Production of alkoxylated amines-
In Example 2, an alkoxylated amine was produced in the same manner as in Example 2 except that after the “catalyst separation step”, a “distillation step” was further performed.

  In Example 2, after the “catalyst separation step”, the additive solvent described in Table 1 was added, and the gas phase part of the obtained reaction solution was replaced with nitrogen gas. The solvent was distilled off by the solvent distillation method described in 1. to give an EO5 molar adduct of laurylamine.

(Example 8)
-Production of alkoxylated amines-
In Example 3, except that boron trifluoride / diethyl ether complex was used as a catalyst, the “addition reaction step”, “catalyst separation step”, and “evaporation step” were performed in the same manner as in Example 3, An EO 5 molar adduct of laurylamine was obtained.

Example 9
-Production of alkoxylated amines-
In Example 6, except that boron tetrafluoride / diethyl ether complex was used as a catalyst, the “addition reaction step”, “catalyst separation step”, and “evaporation step” were performed in the same manner as in Example 6, An EO 5 molar adduct of laurylamine was obtained.

(Example 10)
-Production of alkoxylated amines-
In Example 3, except that magnesium perchlorate was used as a catalyst, the “addition reaction step”, “catalyst separation step”, and “evaporation step” were performed in the same manner as in Example 3, and EO5 of laurylamine was obtained. A molar adduct was obtained.

(Examples 11-14)
-Production of alkoxylated amines-
In Examples 3 to 6, 300 g of stearylamine was used as the aliphatic amine, the amount of ethylene oxide (EO) introduced was 491 g (equivalent to 10 mole addition), and the solvent addition operation in the “evaporation step” was “catalyst separation step. Except that it was performed before ”, an“ addition reaction step ”, a“ catalyst separation step ”and a“ distillation step ”were performed in the same manner as in Examples 3 to 6 to obtain an EO 10 mol adduct of stearylamine. .

(Comparative Example 1)
-Production of alkoxylated amines-
In Example 1, except that NaOH was used as a catalyst, an “addition reaction step” and a “catalyst separation step” were carried out in the same manner as in Example 1 to obtain an EO5 molar adduct of laurylamine.

(Comparative Example 2)
-Production of alkoxylated amines-
In Example 3, except that NaOH was used as a catalyst, an “addition reaction step”, a “catalyst separation step” and a “distillation step” were carried out in the same manner as in Example 3 to obtain an EO5 molar adduct of laurylamine. Got.

(Comparative Example 3)
-Production of alkoxylated amines-
In Example 6, except that NaOH was used as a catalyst, an “addition reaction step”, a “catalyst separation step”, and a “distillation step” were performed in the same manner as in Example 6 to obtain an EO5 molar adduct of laurylamine. Got.

(Comparative Example 4)
-Production of alkoxylated amines-
In Example 11, except that NaOH was used as a catalyst and the “evaporation step” was not performed, the “addition reaction step” and the “catalyst separation step” were performed in the same manner as in Example 11, and EO10 of stearylamine was obtained. A molar adduct was obtained.

(Comparative Example 5)
-Production of alkoxylated amines-
In Example 11, except that NaOH was used as a catalyst, an “addition reaction step”, a “catalyst separation step” and a “distillation step” were performed in the same manner as in Example 11, and an EO 10 mol adduct of stearylamine was obtained. Got.

(Comparative Example 6)
-Production of alkoxylated amines-
In Example 14, except that NaOH was used as a catalyst, an “addition reaction step”, a “catalyst separation step”, and a “distillation step” were performed in the same manner as in Example 14, and an EO 10 mol adduct of stearylamine was obtained. Got.

  About the obtained EO5 mol adduct of laurylamine of Examples 1-10 and Comparative Examples 1-3 and EO10 mol adduct of Examples 11-14 and Comparative Examples 4-6, the following method was used. Color tone evaluation and sensory evaluation of odor were performed. The results are shown in Table 1.

<Color tone evaluation>
The color tone of the obtained EO 5 mol adduct of laurylamine and EO 10 mol adduct of stearylamine was measured by the following Gardner method. In addition, the temperature was maintained at 45 ° C., and the color tone of laurylamine EO 5 mol adduct and stearylamine EO 10 mol adduct after 30 days were also measured.

-Gardner method-
The hue value (Gardner color number) was measured by the Gardner method according to the method described in JIS K5400 4.1.2. In the measurement by this method, the color of the sample (EO 5 mol adduct of laurylamine or EO 10 mol adduct of stearylamine) prepared based on the prescribed method is indicated by the color number of the color glass equal to the Gardner color number standard solution. . Therefore, a sample is collected in a Gardner color number tube (a colorless and transparent glass tube having an inner diameter of 10 mm and a depth of 110 mm), set in a Gardner-Heliga colorimeter, a colorimetric plate is rotated, and the color of the sample is measured by transmitted light. The color that appeared in the window when they matched was read.

<Odor evaluation>
The obtained EO 5 mol adduct of laurylamine and EO 10 mol adduct of stearylamine were subjected to sensory evaluation based on the following criteria.
〔Evaluation criteria〕
◎: Very little odor ○: Little odor △: There is odor ×: Strong odor

なお、表１中、ＥｔＯＨは、エチルアルコールである。

In Table 1, EtOH is ethyl alcohol.

From the results shown in Table 1, the laurylamine EO 5 mol adduct produced in Examples 1 to 10 and the stearylamine EO 10 mol adduct produced in Examples 11 to 14 both have good color tone and odor. confirmed.
Moreover, it was recognized that the deterioration of the color tone when these were preserved for a long time was suppressed.
Furthermore, as shown in Examples 3 to 14, it was confirmed that the odor was further improved when the solvent was distilled off.

The alkoxylated amine produced by the method for producing an alkoxylated amine of the present invention has a good color tone and odor, and particularly, the deterioration of the color tone when stored for a long period of time is improved. It can be suitably used for various detergents using agents, fiber dyeing assistants, fiber softeners, bactericides, agricultural chemical spreaders, antistatic agents, and the like.

Claims (8)

  An alkoxylated amine comprising an addition reaction step of producing an alkylene oxide addition reaction product of an aliphatic amine by adding an alkylene oxide to an aliphatic amine in the presence of either a metal oxide catalyst or an acid catalyst. Production method.   The alkoxylated amine according to claim 1, further comprising a distillation step of adding any solvent of lower alcohol and water to the addition reaction product, and distilling off the solvent either under reduced pressure or under an inert gas flow. Manufacturing method.   The method for producing an alkoxylated amine according to claim 1, wherein the metal oxide catalyst is an aluminum / magnesium composite metal oxide.   The alkoxylated amine according to claim 3, wherein the aluminum-magnesium composite metal oxide contains at least one metal selected from iron, nickel, chromium, manganese, titanium, boron, germanium, cerium, molybdenum, zinc and zirconium. Manufacturing method.   The method for producing an alkoxylated amine according to any one of claims 1 to 2, wherein the acid catalyst is at least one selected from a Lewis acid and a complex thereof, and a perhalogen acid and a salt thereof.   The production of an alkoxylated amine according to any one of claims 1 to 5, wherein the aliphatic amine is any one of an aliphatic primary amine and an aliphatic secondary amine having an aliphatic hydrocarbon group having 8 to 22 carbon atoms. Method.   The method for producing an alkoxylated amine according to any one of claims 1 to 6, wherein the added mole number of the alkylene oxide is 1 to 40 moles relative to the aliphatic amine. The difference between the hue value measured by the Gardner method immediately after the production and the hue value measured after 30 days at 45 ° C is 1 or less. An alkoxylated amine, characterized in that