CN113277952A - Preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine - Google Patents
Preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine Download PDFInfo
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- CN113277952A CN113277952A CN202110440520.4A CN202110440520A CN113277952A CN 113277952 A CN113277952 A CN 113277952A CN 202110440520 A CN202110440520 A CN 202110440520A CN 113277952 A CN113277952 A CN 113277952A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/50—Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
Abstract
The invention discloses a preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine, relating to the technical field of secondary amine preparation, and the preparation method comprises the following steps: adding Raney nickel into C12-14 alkyl polyethylene glycol ether with primary amino group, introducing hydrogen, heating under stirring, reacting, cooling, stopping introducing hydrogen, filtering, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine. The preparation method provided by the invention adopts deamination coupling reaction of primary amine to prepare secondary amine, the reaction can be carried out at normal pressure, the optimal process of the bis (C12-14 alkyl polyoxyethylene) secondary amine is optimized, the side reaction is few, the average content (S%) of the secondary amine in the prepared product is up to 95.5%, the reproducibility of the preparation method is good, the amplification experiment of the preparation method is used for carrying out true value inspection on the reproducibility experiment result, and the result shows that the difference between the two is within the normal error range, so that the requirement of industrial production can be met.
Description
Technical Field
The invention relates to the technical field of secondary amine preparation, and particularly relates to a preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine.
Background
Secondary amines are industrially common synthetic starting materials and intermediates, and there are various preparation methods. Among them, reductive amination is one of the important methods for preparing secondary amines from primary amines. The method generally employed is that a primary amine and an aldehyde first form an imine or an imine ion intermediate, which is then reduced in situ to a secondary amine. However, these reduction methods for producing secondary amines have a problem that over-alkylation inevitably occurs in a considerable number of reactions. In particular, when ammonia is reacted with aldehydes or ketones to produce primary amines, it is more difficult to control the occurrence of further alkylation of the product.
The existing preparation method of secondary amine can not prepare bis (C12-14 alkyl polyoxyethylene) secondary amine with high secondary amine content and stable product quality, so that the bis (C12-14 alkyl polyoxyethylene) secondary amine is lacked in the existing product series.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a preparation method of a bis (C12-14 alkyl polyoxyethylene) secondary amine.
The preparation method comprises the following steps: adding Raney nickel into C12-14 alkyl polyethylene glycol ether with primary amino group, introducing hydrogen, heating under stirring, reacting, cooling, stopping introducing hydrogen, filtering, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, hydrogen is introduced at a certain flow rate, and the hydrogen not only provides a hydrogen environment for the reaction, but also plays a role of bubbling and can take away water and ammonia gas in the reaction system.
Preferably, the amount of the added Raney nickel is 0-5% of the mass of the primary amino-terminated C12-14 alkyl polyethylene glycol ether.
Preferably, the stirring is performed at a stirring speed of 350 r/min.
Preferably, the number average molecular weight of the primary amino-terminated C12-14 alkyl polyglycol ether is 420.
Further preferably, the amination rate is 80 to 90% and the total amine value is 90 to 115 mgKOH/mg.
Preferably, the flow rate of the introduced hydrogen is 100-300 ml/min.
Preferably, the temperature rise is to 155-220 ℃.
Preferably, the flow rate of the introduced hydrogen is 100-300 ml/min.
Preferably, the reaction time is 3-7 h.
Another object of the present invention is to protect the secondary bis (C12-14) alkylpolyoxyethylene ether) amine obtained by the above-mentioned preparation method.
The invention has the beneficial effects that:
(1) the preparation method provided by the invention adopts deamination coupling reaction of primary amine to prepare secondary amine, the reaction can be carried out at normal pressure, the optimal process of the bis (C12-14 alkyl polyoxyethylene) secondary amine is optimized, the side reaction is few, the average content (S%) of the secondary amine in the prepared product is up to 95.5%, the reproducibility of the preparation method is good, the amplification experiment of the preparation method is used for carrying out true value inspection on the reproducibility experiment result, and the result shows that the difference between the two is within the normal error range, so that the requirement of industrial production can be met.
(2) The preparation method provided by the invention adopts a single reactant as a raw material, the raw material is easy to obtain, the feeding is convenient during production operation, the process flow is simple, the cost is reduced, the secondary amine content of the product is high, and the preparation method is suitable for large-scale production in the industrial field.
Drawings
In order to more clearly illustrate the detailed description of the invention or the technical solutions in the prior art, the drawings that are needed in the detailed description of the invention or the prior art will be briefly described below. Throughout the drawings, like elements or portions are generally identified by like reference numerals. In the drawings, elements or portions are not necessarily drawn to scale.
FIG. 1 shows the effect of different amine number raw materials on the S% content of secondary amine in the product;
FIG. 2 is a graph showing the effect of different amine number raw materials on the primary amine content P% and the tertiary amine content T% of the product;
FIG. 3 is a graph showing the interaction of various amine number feedstocks with reaction time;
FIG. 4 is a graph showing the effect of reaction temperature on the S% secondary amine content of the product;
FIG. 5 is a graph showing the effect of catalyst loading on the S% secondary amine content of the product;
FIG. 6 is a graph showing the effect of vent conditions on the S% secondary amine content of the product;
FIG. 7 is a graph showing the effect of reaction time on the S% secondary amine content of the product;
FIG. 8 is a mean test of the scale-up experiment and the reproducibility experiment.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to the accompanying drawings. The following examples are only for illustrating the technical solutions of the present invention more clearly, and therefore are only examples, and the protection scope of the present invention is not limited thereby.
It is to be noted that, unless otherwise specified, technical or scientific terms used herein shall have the ordinary meaning as understood by those skilled in the art to which the invention pertains.
Example 1
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps:
adding 200g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 500ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 5.0 percent of the total mass of the raw materials, introducing hydrogen, the hydrogen flow is 100ml/min, heating to 200 ℃ under stirring at a stirring speed of 350r/min, reacting for 5 hours, cooling to below 60 ℃, stopping introducing the hydrogen, performing suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein the number average molecular weight of the primary amino-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 90-115 mgKOH/mg.
The secondary amine bis (C12-14 alkylpolyoxyethylene) prepared in example 1 was tested for secondary amine content (S%), primary amine content (P%), tertiary amine content (T%) and amination ratio (A.R.) and the results are shown in FIG. 1, FIG. 2 and Table 1.
The calculation formula is as follows: (1) the ratio of the secondary amine value to the total amine value is defined as the secondary amine content (S%), and is used for measuring the percentage of the secondary amine in the total amine in the reaction product, and the calculation formula is shown as the formula (1.1)
In the formula: percent S- -Secondary amine,%;
AS- -secondary amine number, mg KOH/g;
a- -Total amine number, mg KOH/g.
(2) The calculation formula of primary amine content (P%) is as shown in formula (1.2)
In the formula: p — primary amine percentage,%;
AP- -primary amine number, mg KOH/g;
a- -Total amine number, mg KOH/g.
(3) The formula for calculating the content (T%) of tertiary amine is as shown in formula (1.3)
In the formula: t-tertiary amine percentage,%;
AT- -tertiary amine number, mg KOH/g;
a- -Total amine number, mg KOH/g.
(4) Theoretically, one molecule of secondary amine is generated by condensation of every two molecules of primary amine, and the amine value of the product is reduced due to the side reaction of primary amine hydrolysis, so that the detection index of the product except the content (S%) of the secondary amine also needs to increase the ratio of the actual amine value to the theoretical amine value, namely the amination rate (A.R.), and the calculation formula is expressed as a percentage (1.4).
In the formula: A.R- -amination rate,%;
a- -actual amine number of the product, mg KOH/g;
m- -number average molecular weight of the starting materials A/C12-14E 5.
TABLE 1
As can be seen from FIG. 1 and Table 1, when the higher amine value primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) is selected, the secondary amine content (S%) will increase rapidly, and at the same time, the tertiary amine content (T%) will decrease from FIG. 2. since the lower amine value of the raw material A/C12-14E5 will contain some amount of secondary and tertiary amines, and the tertiary amine in the product will be mainly from the raw material rather than by-products, the amine value of the raw material A/C12-14E5 will decrease the content of tertiary amine, and thus the secondary amine content (S%) will increase relatively.
When the A/C12-14E5 with higher amine value is selected, the content of the secondary amine (S%) is gradually reduced, and the content of the secondary amine (S%) is reduced, because the content of the primary amine is relatively increased when the amine value of the A/C12-14E5 is continuously increased, and the content of the unreacted primary amine is increased in the same reaction time. Therefore, the decrease in the secondary amine content (S%) of the bis (C12-14 alkylpolyoxyethylene) secondary amine (S/C12-14E5) is accompanied by an increase in the primary amine content (P%) and a decrease in the tertiary amine content (T%).
The interaction effect of raw materials with different amine values and reaction time is determined, a 2^2 factorization experiment is carried out, the experiment factors and the levels are shown in a table 2, and the result is shown in a table 3.
TABLE 2
As can be seen from FIG. 3, the included angles between the raw materials with different amine values and different reaction times in FIG. 3 illustrate the phenomenon that the amine value of the raw materials is increased and the content (S%) of the secondary amine of the product is reduced due to the obvious interaction between the two factors. Meanwhile, as can be seen from the curve at the upper right corner of fig. 3, when the raw material with a higher amine value is selected, the line type is relatively gentle, which indicates that the influence of the reaction time is relatively small under the condition. Therefore, the raw materials with high amine value can be selected to prepare S/C12-14E5 by prolonging the reaction time, so that the product index has certain stability.
Example 2
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps: adding 200g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 500ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 5.0 percent of the total mass of the raw materials, introducing hydrogen, the hydrogen flow is 100ml/min, heating to 155 and 220 ℃ under stirring at the stirring speed of 300r/min, reacting for 5 hours, cooling to below 100 ℃, stopping introducing the hydrogen, performing suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, the number average molecular weight of the primary amino group-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 94.6 mgKOH/mg.
The effect of reaction temperature on the secondary amine content of the reaction product was tested and the results are shown in FIG. 4.
As can be seen from fig. 4, the reaction temperature is increased, the reaction rate is increased, and when the reaction temperature is 160 ℃, the reaction rate is slower, and the content of secondary amine (S%) is only 68.0%; when the reaction temperature is increased from 180 ℃ to 200 ℃, the content of the secondary amine is increased from 83.8 percent to 86.2 percent; as the temperature continues to rise, the rate of reaction at which the secondary amine will condense further to form the tertiary amine increases, resulting in an increase in the tertiary amine content. Therefore, the reaction temperature is preferably 200 ℃.
Example 3
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps:
adding 200g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 500ml four-neck flask, adding a catalyst Raney nickel into the flask, wherein the dosage of the catalyst is 0-5.0% of the total mass of the raw materials, introducing hydrogen, the hydrogen flow is 200ml/min, heating to 200 ℃ under stirring at a stirring speed of 300r/min, reacting for 5 hours, cooling to below 100 ℃, stopping introducing the hydrogen, performing suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, the number average molecular weight of the primary amino group-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 94.6 mgKOH/mg.
The effect of the amount of catalyst used on the secondary amine content of the reaction product was tested and the results are shown in FIG. 5.
As can be seen from FIG. 5, almost no secondary amines were formed when no catalyst was added, with about 10% of the secondary amines being mainly derived from the starting materials A/C12-14E 5; the catalyst is not used in a small amount enough to catalyze the reaction; when the using amount of the catalyst is 2.5 percent of the total mass of the raw materials, the content of secondary amine (S%) reaches 94.3 percent at most; the content of secondary amine (S%) will slowly decrease with increasing catalyst dosage, so the catalyst dosage is preferably 2.5%.
Example 4
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps:
adding 200g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 500ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 2.5 percent of the total mass of the raw materials, introducing gas which is hydrogen or nitrogen, heating to 200 ℃ under stirring at a stirring speed of 300r/min, reacting for 5 hours, cooling to below 100 ℃, stopping introducing the hydrogen, performing suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, the number average molecular weight of the primary amino group-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 94.6 mgKOH/mg.
Wherein, the hydrogen flow is 0-200ml/min when the hydrogen is introduced, and the nitrogen flow is 100ml/min when the hydrogen is introduced.
The effect of aeration on the secondary amine content of the reaction product was tested and the results are shown in FIG. 6.
As can be seen from fig. 6, when nitrogen is introduced into the reaction system, a certain amount of secondary amine is still generated, because during the reaction, the reactant itself has a dehydrogenation process to generate hydrogen, even under the condition of not introducing hydrogen, the reaction can still proceed, but due to the insufficient amount of hydrogen, the formation of a nitrogen-containing compound layer on the surface of the catalyst cannot be effectively prevented, thereby resulting in the reduction of the activity of the catalyst; when no gas is introduced in the reaction process, the content of secondary amine (S%) is sharply reduced, and the product has darker color because reactants are in contact with oxygen in the air and are oxidized, but the yellowing process is more obvious and acute due to the higher reaction temperature; after a certain amount of hydrogen is introduced into the reaction system, the content (S%) of secondary amine is obviously increased; as the hydrogen flow rate is further increased, the content of secondary amine (S%) is decreased to some extent, and the reaction rate of the dehydrogenation process may be inhibited due to the increase of the hydrogen flow rate, thereby being unfavorable for the generation of secondary amine. When the hydrogen flow rate is 200ml/min, the secondary amine content (S%) is maximized, so that the hydrogen flow rate is preferably 200 ml/min.
Example 5
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps:
adding 200g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 500ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 2.5 percent of the total mass of the raw materials, introducing hydrogen, the hydrogen flow is 200ml/min, heating to 200 ℃ with stirring at the stirring speed of 300r/min, reacting for 3-7h, cooling to below 100 ℃, stopping introducing the hydrogen, performing suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, the number average molecular weight of the primary amino group-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 94.6 mgKOH/mg.
The effect of reaction time on the secondary amine content of the reaction product was tested and the results are shown in FIG. 7.
As can be seen from FIG. 7, the secondary amine content (S%) also increased with the increase of the reaction time, and reached the maximum when the reaction time was 6 hours; the reaction time is preferably 6 hours, since only the secondary amine is further condensed to form a tertiary amine, resulting in a decrease in the content of the secondary amine (S%).
Test example 1
Reproducibility test
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps:
adding 200g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 500ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 2.5 percent of the total mass of the raw materials, introducing hydrogen, the hydrogen flow is 200ml/min, heating to 200 ℃ under stirring at the stirring speed of 300r/min, reacting for 6h, cooling to below 100 ℃, stopping introducing the hydrogen, performing suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, the number average molecular weight of the primary amino group-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 94.6 mgKOH/mg.
Three reproducibility experiments were performed according to the above method, and the content of secondary amine (S%) and the average content of secondary amine (S%) obtained by the reaction products of the three reactions were measured, and the results are shown in table 3.
TABLE 3
Test example 2
Amplification experiment
A preparation method of bis (C12-14 alkyl polyoxyethylene) secondary amine comprises the following steps:
adding 1000g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 2000ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 2.5 percent of the total mass of the raw materials, introducing hydrogen, regulating the hydrogen flow to be 400ml/min because of the limitation of a reaction device and the hydrogen flow cannot be amplified by 5 times according to the equal proportion of the raw material flow, heating to 200 ℃ under stirring at the stirring speed of 300r/min, reacting for 6 hours, cooling to below 100 ℃, stopping introducing the hydrogen, performing suction filtration, removing the catalyst, and obtaining the bis (C12-14 alkyl polyoxyethylene) secondary amine.
Wherein, the number average molecular weight of the primary amino group-terminated C12-14 alkyl polyglycol ether is 420, and the total amine value is 94.6 mgKOH/mg.
Two experiments are repeated according to the method to prepare the bis (C12-14 alkyl polyoxyethylene) secondary amine 1#, the bis (C12-14 alkyl polyoxyethylene) secondary amine 2 #.
The scale-up is continued on the basis of the process for preparing the secondary bis (C12-14 alkylpolyoxyethylene) amines, 1# and 2#, by the following steps:
adding 2000g of primary amino-terminated C12-14 alkyl polyglycol ether (A/C12-14E5) into a 5000ml four-neck flask, adding Raney nickel catalyst into the flask, wherein the dosage of the catalyst is 2.5 percent of the total mass of the raw materials, introducing hydrogen, the hydrogen flow is 400ml/min, heating to 200 ℃ under stirring at the stirring speed of 300r/min,
and (3) carrying out reaction for 7h, cooling to below 100 ℃, stopping introducing hydrogen, carrying out suction filtration, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine # 3.
The reaction time was 7h for the reason: the hydrogen flow is 400ml/min, the ammonia gas generated by the reaction is increased by amplifying the raw material flow, and the hydrogen flow is insufficient, so that the generated ammonia gas cannot be taken out of the reaction system, the forward proceeding of the reaction balance can be hindered, the reaction rate is slowed down, and the reaction time is correspondingly prolonged to 7 h.
The secondary amine content (S%) and amination ratio (A.R.) of the obtained bis (C12-14 alkylpolyoxyethylene) secondary amine No. 1-3 were measured, and the results are shown in Table 4.
TABLE 4
| Product numbering | Secondary amine content (S%) | Amination Rate (A.R.) |
| 1# | 92.4 | 98.3 |
| 2# | 92.7 | 98.6 |
| 3# | 92.3 | 97.5 |
Comparing the amplification experimental result (3#) with the reproducibility experimental result, performing mean value test, and passing the statistical process
The software was subjected to data processing and the experimental results are shown in fig. 8.
As can be seen from fig. 8, the P value of the mean test is 0.13, which is greater than the value of 0.1 commonly used in industrial production, indicating that the difference between the amplified experimental result and the reproducible experimental result is within the normal experimental error. Therefore, the preparation method provided by the invention can be used for amplification reaction operation, and has higher content of secondary amine (S%).
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; such modifications and substitutions do not depart from the spirit and scope of the present invention, and they should be construed as being included in the following claims and description.
Claims (10)
1. A method for preparing a bis (C12-14 alkyl polyoxyethylene) secondary amine, which is characterized by comprising the following steps: the preparation method comprises the following steps: adding Raney nickel into C12-14 alkyl polyethylene glycol ether with primary amino group, introducing hydrogen, heating under stirring, reacting, cooling, stopping introducing hydrogen, filtering, and removing the catalyst to obtain the bis (C12-14 alkyl polyoxyethylene) secondary amine.
2. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the added Raney nickel accounts for 0-5% of the mass of the primary amino-terminated C12-14 alkyl polyethylene glycol ether.
3. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the stirring is carried out at a stirring speed of 350 r/min.
4. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the number average molecular weight of the primary amino-terminated C12-14 alkyl polyglycol ether is 420.
5. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 4, wherein: the amination rate is 80-90%, and the total amine value is 90-115 mgKOH/mg.
6. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the flow rate of the introduced hydrogen is 100-300 ml/min.
7. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the temperature rise is to 155-220 ℃.
8. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the flow rate of the introduced hydrogen is 100-300 ml/min.
9. A process for producing a bis (C12-14 alkylpolyoxyethylene) secondary amine as claimed in claim 1, wherein: the reaction time is 3-7 h.
10. A secondary bis (C12-14 alkylpolyoxyethylene) amine produced by the process of any one of claims 1 to 9.
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| CN103613506A (en) * | 2013-11-26 | 2014-03-05 | 南京林业大学 | Preparation method of bis(fatty alcohol polyoxyalkene ether) secondary amine |
| CN105601887A (en) * | 2015-12-31 | 2016-05-25 | 上海美东生物材料股份有限公司 | Alicyclic amine curing agent and preparing method thereof |
| EP3064524A1 (en) * | 2014-12-04 | 2016-09-07 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103613506A (en) * | 2013-11-26 | 2014-03-05 | 南京林业大学 | Preparation method of bis(fatty alcohol polyoxyalkene ether) secondary amine |
| EP3064524A1 (en) * | 2014-12-04 | 2016-09-07 | Shin-Etsu Chemical Co., Ltd. | Method for producing polyalkylene glycol derivative having amino group at end |
| CN105601887A (en) * | 2015-12-31 | 2016-05-25 | 上海美东生物材料股份有限公司 | Alicyclic amine curing agent and preparing method thereof |
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