CN108311056A - A kind of narrow ditribution Gemini surface active agent and preparation method thereof - Google Patents
A kind of narrow ditribution Gemini surface active agent and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of narrow ditribution Gemini surface active agents and preparation method thereof, which includes the following steps：It is first 1 according to molar ratio by acetylenic glycols and ethylene oxide:1~20 is uniformly mixed, and it is 50~120 DEG C to add nitrogen heterocycles catalyst temperature in system, and pressure carries out addition reaction under conditions of being 0.3~0.8MPa, you can generates narrow ditribution Gemini surface active agent.The narrow ditribution Gemini surface active agent of the present invention not only overcomes that traditional catalyst color and luster is deep, alkynyl retention rate is low, but also improves the distribution character of product, improves the narrow ditribution characteristic of product；Additionally provide a kind of preparation method of narrow ditribution Gemini surface active agent.
Description
Technical field
The present invention relates to the technical fields of surfactant, in particular to a kind of narrow ditribution Gemini surface active agent and its system
Preparation Method.
Background technology
Gemini surface active agent has dosage few, is easy to form variform in gas-liquid surface, while only needing to be added 1 ‰
The double effects that wetting and defoaming can be arrived solve traditional antifoaming agent and are partial to oiliness, water-soluble bad, molecular weight compared with
The shortcomings such as greatly, wetting power is poor.
Chinese invention patent Publication No. CN103601881A is disclosed in potassium hydroxide, sodium hydroxide, sodium fluoride
One or more mixtures is catalyst.This method can not ensure the stability of alkynyl, while used sodium fluoride
It is toxic, it is unfavorable for applying downstream.
Chinese invention patent Publication No. CN102304029A and Chinese invention patent publication No. are that CN103965461B is equal
It discloses and traditional trimethylamine is used to be synthesized for catalyst, such catalyst activity is relatively low and the products molecule for preparing
Wider distribution is measured, properties of product are worse than the synthesis mode of this patent report.
Invention content
Present invention aim to provide a kind of narrow ditribution Gemini surface active agent, the Gemini surface active agent is not only gram
It is low to have taken traditional catalyst color and luster depth, alkynyl retention rate, and has improved the distribution character of product, the narrow ditribution for improving product is special
Property；Additionally provide a kind of preparation method of narrow ditribution Gemini surface active agent.
To achieve the above object, the present invention provides a kind of narrow ditribution Gemini surface active agent, the narrow ditribution Shuangzi tables
The structural formula of face activating agent such as following formula (I)：
In formula (I), R1、R4For C2-C12Saturated alkane in range；R2、R3For C1-C4Saturated alkane in range；N and m
The sum of for the integer in 2~20.
Preferably, the structural formula such as following formula of the narrow ditribution Gemini surface active agent：
In formula, R1For (CH3)2CH2CH2, R2For (CH3)2CH2CH2, R3For (CH3)2CH2, R4For (CH3)2CH2CH2CH2CH2-。
The present invention also provides a kind of preparation methods of above-mentioned narrow ditribution Gemini surface active agent, include the following steps：First
Acetylenic glycols are uniformly mixed with ethylene oxide, nitrogen heterocycles catalyst is added and carries out addition reaction, you can it is double to generate narrow ditribution
Sub- surfactant.
Further, the molar ratio of acetylenic glycols and ethylene oxide is 1:1~20.
Further, the structural formula of the acetylenic glycols is lower formula (II)：
In formula (II), R1、R4For C2-C12Saturated alkane in range；R2、R3For C1-C4Saturated alkane in range.
Further, the nitrogen heterocycles catalyst is 1,8- diazabicylos, 11 carbon -7- alkene (DBU),-two idol of Isosorbide-5-Nitrae
Bicyclic [2.2.2] octane (DABCO) of nitrogen, 1,4- diazabicylos [2.2.2] octane (ABCO), 4-dimethylaminopyridine
(DMAP), one or more in triethylamine.
Preferably, the nitrogen heterocycles catalyst is 1,8- diazabicylos, 11 carbon -7- alkene (DBU),-two azo of Isosorbide-5-Nitrae
Bicyclic [2.2.2] octane (DABCO), triethylamine are according to mass ratio 3:1:2 mix.
Further, the addition of the nitrogen heterocycles catalyst be acetylenic glycols and ethylene oxide gross mass 0.05%~
2%.
Still further, temperature is 50~120 DEG C in the system of the addition reaction, pressure is 0.3~0.8MPa.
Further, the product obtained after the addition reaction, then carry out maturation process；The burin-in process is specially
Maintenance system temperature is 50~120 DEG C, until reactor pressure no longer declines, maturation process is completed.
Compared with prior art, the invention has the advantages that：
First, the narrow ditribution Gemini surface active agent of the present invention not only overcomes traditional catalyst color and luster depth, alkynyl retains
Rate is low, and improves the distribution character of product, improves the narrow ditribution characteristic of product.Such as due to traditional inorganic base catalyst：Hydrogen
Potassium oxide and sodium hydroxide, which are easy to cause acetylenic diols substance decomposition, reduces alkynyl retention rate, and decomposition while can cause color to add
Deeply, while using traditional tertiary amine catalyst steric hindrance relatively low, catalytic activity is relatively low to generally require 100 DEG C or more
Hot conditions could catalyze and synthesize well, be unfavorable for the narrow ditribution of ethylene oxide under these conditions.
Second, the present invention narrow ditribution Gemini surface active agent in lower temperature range, by high activated catalyst come
The method for realizing narrow ditribution effect；Nitrogen heterocycles organic base has many excellent characteristics, stable structure, while alkalinity is better than
General tertiary amines organic base, catalytic effect is particularly evident in ethoxylation synthesis, just because of this characteristic is so that azepine
Ring class organic base can carry out ethoxylation synthetic reaction under lower temperature conditions, also lay good base for narrow ditribution
Plinth.
Third, the sample that the narrow ditribution Gemini surface active agent of the present invention solves conventional catalyst synthesis by narrow ditribution is low
The relatively low problem of warm easily solidification, cloud point.Traditional catalyst is susceptible to layering under cryogenic since molecular weight distribution is wider
Even solidify the phenomenon that, while the cloud point of synthesized substance and pour point also due to molecular weight width occur significant changes,
The low temperature resistant and high temperature resistance enhancing of product in use can be made by resolving the distribution problem of product, be conducive to product
The broadening of application field.
Description of the drawings
Fig. 1 is the NMR spectra of the narrow ditribution Gemini surface active agent of the embodiment of the present invention 1.
Specific implementation mode
Technical scheme of the present invention clearly, comprehensively describe with reference to specific implementation case.It should be appreciated that
Particular embodiments described herein is only used for explaining the present invention, is not intended to limit the present invention.What is be not specified in embodiment is specific
Condition person carries out according to conventional conditions or manufacturer's recommended conditions；Manufacturer is not specified in agents useful for same or instrument, can be with
The conventional products obtained by commercially available purchase.
Embodiment 1
The 11 carbon -7- alkene of acetylenic glycols and 5g1,8- diazabicylos of 1mol is added in the autoclave that the band of l L stirs
(DBU), airtight test is carried out to reaction kettle, it is right under the conditions of 50 DEG C after reaction kettle pressure phenomenon does not occur in 1 hour
It carries out nitrogen displacement and vacuum pumping, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times, row
It is depressed into 0~30KPa, ethylene oxide is then passed through into reaction kettle, controlling reaction temperature is 120 DEG C ± 3 DEG C and reaction pressure is
0.3MPa~0.5MPa, until the total amount for being passed through ethylene oxide stops being passed through ethylene oxide when being 10mol, after being carried out to product
It is 120 DEG C ± 3 DEG C to handle aging and maintain temperature of reaction kettle, until reactor pressure no longer declines, shows to complete slaking reaction.Drop
It to 60 DEG C, is neutralized with glacial acetic acid and takes off low boiling, you can obtain narrow ditribution Gemini surface active agent.
The structure of product is the narrow ditribution Gemini surface active agent containing alkynes through NMR spectra confirmation, wherein NMR schemes such as
Shown in Fig. 1.
Embodiment 2
The 11 carbon -7- of 1,8- diazabicylos of the acetylenic glycols and 5g of 1mol is added in the autoclave that the band of l L stirs
Alkene (DBU) carries out airtight test to reaction kettle, after reaction kettle pressure phenomenon does not occur in 1 hour under the conditions of 50 DEG C
Nitrogen displacement and vacuum pumping are carried out to it, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times,
Then row pressure is passed through ethylene oxide to 0~30KPa into reaction kettle, controlling reaction temperature is 90 DEG C ± 3 DEG C and reaction pressure
For 0.3MPa~0.5MPa, the total amount up to being passed through ethylene oxide stops being passed through ethylene oxide when being 10mol, after being carried out to product
It is 90 DEG C ± 3 DEG C to handle aging and maintain temperature of reaction kettle, until reactor pressure no longer declines, shows to complete slaking reaction.Drop
It to 60 DEG C, is neutralized with glacial acetic acid and takes off low boiling, you can obtain narrow ditribution Gemini surface active agent.
Embodiment 3
The 1,4- diazabicylos [2.2.2] of the acetylenic glycols and 2.5g of 1mol are added in the autoclave that the band of l L stirs
Octane (ABCO) and bicyclic [2.2.2] octane (DABCO) of bis- azo of 2.5g1,4- are used as catalyst, are carried out to reaction kettle airtight
Property inspection carries out nitrogen displacement to it under the conditions of 50 DEG C after reaction kettle pressure phenomenon does not occur in 1 hour and vacuumizes
Operation, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times, row pressure to 0~30KPa, then to anti-
It answers and is passed through ethylene oxide in kettle, controlling reaction temperature is 00 DEG C ± 3 DEG C and reaction pressure is 0.3MPa~0.5MPa, until being passed through
Stop being passed through ethylene oxide when the total amount of ethylene oxide is 10mol, carrying out post-processing aging maintenance temperature of reaction kettle to product is
90 DEG C ± 3 DEG C, until reactor pressure no longer declines, show to complete slaking reaction.60 DEG C are down to, neutralized with glacial acetic acid and is taken off are low
Boiling.
Embodiment 4
Bis- azos of 1,4- of 1mol is added in the autoclave that the band of l L stirs acetylenic glycols and 2.5g are bicyclic [2.2.2]
The 4-dimethylaminopyridine (DMAP) of octane (DABCO) and 2.5g are used as catalyst, and airtight test is carried out to reaction kettle, wait for anti-
Nitrogen displacement and vacuum pumping are carried out to it under the conditions of 50 DEG C after answering kettle not occur pressure phenomenon in 1 hour, it is ensured that take out
Vacuum time is more than 30min, and high pure nitrogen replaces number of operations 5 times, then row pressure to 0~30KPa is passed through ring into reaction kettle
Oxidative ethane, controlling reaction temperature is 90 DEG C ± 3 DEG C and reaction pressure is 0.3MPa~0.5MPa, until being passed through the total of ethylene oxide
Stop being passed through ethylene oxide when amount is 10mol, product is carried out post-processing aging to maintain temperature of reaction kettle being 90 DEG C ± 3 DEG C, directly
No longer decline to reactor pressure, shows to complete slaking reaction.60 DEG C are down to, is neutralized with glacial acetic acid and takes off low boiling, you can is obtained
Narrow ditribution Gemini surface active agent.
Embodiment 5
4-dimethylaminopyridine (DMAP) conduct of the acetylenic glycols and 5g of 1mol is added in the autoclave that the band of l L stirs
Catalyst carries out airtight test to reaction kettle, after reaction kettle pressure phenomenon does not occur in 1 hour under the conditions of 50 DEG C
Nitrogen displacement and vacuum pumping are carried out to it, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times,
Then row pressure is passed through ethylene oxide to 0~30KPa into reaction kettle, controlling reaction temperature is 90 DEG C ± 3 DEG C and reaction pressure
For 0.3MPa~0.5MPa, the total amount up to being passed through ethylene oxide stops being passed through ethylene oxide when being 10mol, after being carried out to product
It is 90 DEG C ± 3 DEG C to handle aging and maintain temperature of reaction kettle, until reactor pressure no longer declines, shows to complete slaking reaction.Drop
It to 60 DEG C, is neutralized with glacial acetic acid and takes off low boiling, you can obtain narrow ditribution Gemini surface active agent.
Embodiment 6
11 carbon of 1,8- diazabicylos-of the acetylenic glycols and 2.5g of 1mol is added in the autoclave that the band of l L stirs
Bicyclic [2.2.2] octane (DABCO) of bis- azos of 1,4- of 7- alkene (DBU) and 1.5g, 1g 1,4- diazabicylos [2.2.2]
Octane (ABCO) is used as catalyst, airtight test is carried out to reaction kettle, after reaction kettle pressure phenomenon does not occur in 1 hour
Nitrogen displacement and vacuum pumping are carried out to it under the conditions of 50 DEG C, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen is set
Change number of operations 5 times, then row pressure to 0~30KPa is passed through ethylene oxide into reaction kettle, controlling reaction temperature is 90 DEG C ± 3
DEG C and reaction pressure be 0.3MPa~0.5MPa, until be passed through ethylene oxide total amount be 10mol when stop be passed through epoxy second
Alkane carries out post-processing aging to maintain temperature of reaction kettle being 90 DEG C ± 3 DEG C, until reactor pressure no longer declines, show to product
Complete slaking reaction.60 DEG C are down to, is neutralized with glacial acetic acid and takes off low boiling, you can obtains narrow ditribution Gemini surface active agent.
Embodiment 7
The 11 carbon -7- of 1,8- diazabicylos of the acetylenic glycols and 3g of 1mol is added in the autoclave that the band of l L stirs
Alkene (DBU), bicyclic [2.2.2] octane (DABCO) of-two azo of Isosorbide-5-Nitrae of 1g, 2g triethylamines carry out reaction kettle as catalyst
Airtight test carries out nitrogen displacement and pumping under the conditions of 50 DEG C after reaction kettle pressure phenomenon does not occur in 1 hour to it
Vacuumizing, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times, row pressure to 0~30KPa, then
Ethylene oxide is passed through into reaction kettle, controlling reaction temperature is 120 DEG C ± 3 DEG C and reaction pressure is 0.3MPa~0.5MPa, directly
Stop being passed through ethylene oxide to being passed through when the total amount of ethylene oxide is 10mol, carrying out post-processing aging to product maintains reaction kettle
Temperature is 120 DEG C ± 3 DEG C, until reactor pressure no longer declines, shows to complete slaking reaction.60 DEG C are down to, in glacial acetic acid
With and de- low boiling, you can obtain narrow ditribution Gemini surface active agent.
Embodiment 8
The 1,4- diazabicylos [2.2.2] of acetylenic glycols and 5g that 1mol is added in the autoclave that the band of l L stirs are pungent
Alkane (ABCO) is catalyst, and airtight test is carried out to reaction kettle, 50 after reaction kettle pressure phenomenon does not occur in 1 hour
Nitrogen displacement and vacuum pumping are carried out to it under the conditions of DEG C, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number
Then operation 5 times, row pressure to 0~30KPa are passed through ethylene oxide into reaction kettle, controlling reaction temperature be 120 DEG C ± 3 DEG C and
Reaction pressure is 0.3MPa~0.5MPa, until the total amount for being passed through ethylene oxide stops being passed through ethylene oxide when being 10mol, to production
Object carries out post-processing aging and maintains temperature of reaction kettle to be 120 DEG C ± 3 DEG C, until reactor pressure no longer declines, shows to complete ripe
Change reaction.60 DEG C are down to, is neutralized with glacial acetic acid and takes off low boiling, you can obtains narrow ditribution Gemini surface active agent.
Embodiment 9
The 4- diformazan ammonia of the acetylenic glycols and 2.5g triethylamines and 2.5g of 1mol is added in the autoclave that the band of l L stirs
Yl pyridines (DMAP) are catalyst, airtight test are carried out to reaction kettle, after reaction kettle pressure phenomenon does not occur in 1 hour
Nitrogen displacement and vacuum pumping are carried out to it under the conditions of 50 DEG C, it is ensured that the pumpdown time is more than 30min, high pure nitrogen displacement
Then number of operations 5 times, row pressure to 0~30KPa are passed through ethylene oxide into reaction kettle, controlling reaction temperature is 90 DEG C ± 3 DEG C
It is 0.3MPa~0.5MPa with reaction pressure, until the total amount for being passed through ethylene oxide stops being passed through ethylene oxide when being 10mol, it is right
Product carries out post-processing aging and maintains temperature of reaction kettle to be 90 DEG C ± 3 DEG C, until reactor pressure no longer declines, shows to complete ripe
Change reaction.60 DEG C are down to, is neutralized with glacial acetic acid and takes off low boiling, you can obtains narrow ditribution Gemini surface active agent.
Embodiment 10
The acetylenic glycols and bicyclic [2.2.2] octane of bis- azos of 1,4- of 1mol are added in the autoclave that the band of l L stirs
(DABCO) and 4-dimethylaminopyridine (DMAP) is used as catalyst (bicyclic [2.2.2] octane (DABCO) of bis- azos of 1,4- and 4-
The mass ratio of dimethylamino naphthyridine is 1：1, total addition is the 2% of acetylenic glycols and ethylene oxide gross mass), to reaction kettle into
Row airtight test, under the conditions of 120 DEG C it is carried out after reaction kettle pressure phenomenon does not occur in 1 hour nitrogen displacement and
Vacuum pumping, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times, row pressure to 0~30KPa, so
Ethylene oxide is passed through in backward reaction kettle, controlling reaction temperature is 120 DEG C ± 3 DEG C and reaction pressure is 0.5MPa~0.8MPa,
Until the total amount for being passed through ethylene oxide stops being passed through ethylene oxide when being 1mol, carrying out post-processing aging to product maintains reaction kettle
Temperature is 120 DEG C ± 3 DEG C, until reactor pressure no longer declines, shows to complete slaking reaction.60 DEG C are down to, in glacial acetic acid
With and de- low boiling, you can obtain narrow ditribution Gemini surface active agent.
Embodiment 11
The acetylenic glycols and triethylamine and 4-dimethylaminopyridine (DMAP) of 1mol are added in the autoclave that the band of l L stirs
(triethylamine and the mass ratio of 4-dimethylaminopyridine are 1：1, total addition is the 2% of acetylenic glycols and ethylene oxide gross mass) make
For catalyst, airtight test is carried out to reaction kettle, after reaction kettle pressure phenomenon does not occur in 1 hour under the conditions of 50 DEG C
Nitrogen displacement and vacuum pumping are carried out to it, it is ensured that the pumpdown time is more than 30min, and high pure nitrogen replaces number of operations 5 times,
Then row pressure is passed through ethylene oxide, controlling reaction temperature is 50 DEG C ± 3 DEG C and reaction pressure is to 0~30KPa into reaction kettle
0.6MPa~0.8MPa, until the total amount for being passed through ethylene oxide stops being passed through ethylene oxide when being 20mol, after being carried out to product
It is 50 DEG C ± 3 DEG C to manage aging and maintain temperature of reaction kettle, until reactor pressure no longer declines, shows to complete slaking reaction.It is down to
It 40 DEG C, is neutralized with glacial acetic acid and takes off low boiling, you can obtain narrow ditribution Gemini surface active agent.
Embodiment 12
(addition is acetylenic glycols and epoxy to the acetylenic glycols of addition 1mol with triethylamine in the autoclave that the band of l L stirs
The 0.05% of ethane gross mass) it is used as catalyst, airtight test is carried out to reaction kettle, waits for that reaction kettle does not occur in 1 hour
Nitrogen displacement and vacuum pumping are carried out to it under the conditions of 50 DEG C after falling to press phenomenon, it is ensured that the pumpdown time is more than 30min, high
Pure nitrogen gas replaces number of operations 5 times, then row pressure to 0~30KPa is passed through ethylene oxide, controlling reaction temperature into reaction kettle
Be 120 DEG C ± 3 DEG C and reaction pressure be 0.3MPa~0.5MPa, until the total amount for being passed through ethylene oxide stops leading to when being 15mol
Enter ethylene oxide, product is carried out post-processing aging to maintain temperature of reaction kettle being 120 DEG C ± 3 DEG C, until reactor pressure is no longer
Decline, shows to complete slaking reaction.60 DEG C are down to, is neutralized with glacial acetic acid and takes off low boiling, you can obtains the work of narrow ditribution Shuangzi surface
Property agent.
Acetylenic glycols chemical structural formula in 1~embodiment of embodiment 12：
The chemical constitution of table 1- acetylenic glycols is constituted
Effect example：
Degree of unsaturation, coloration, cloud point and the pour point of the product prepared by 1~embodiment of embodiment 12 are measured, as a result such as table
2。
Table 2
The above description is merely a specific embodiment, it is noted that any technical person familiar with the field exists
Disclosed herein technical scope in, the change or replacement that can be readily occurred in, should all cover protection scope of the present invention it
It is interior.
Claims (10)
1. a kind of narrow ditribution Gemini surface active agent, which is characterized in that the structural formula of the narrow ditribution Gemini surface active agent is such as
Lower formula (I)：
In formula (I), R1、R4For C2-C12Saturated alkane in range；R2、R3For C1-C4Saturated alkane in range；The sum of n and m
For the integer in 2~20.
2. narrow ditribution Gemini surface active agent according to claim 1, which is characterized in that live on narrow ditribution Shuangzi surface
The structural formula such as following formula of property agent：
In formula, R1For (CH3)2CH2CH2, R2For (CH3)2CH2CH2, R3For (CH3)2CH2, R4For (CH3)2CH2CH2CH2CH2-。
3. a kind of preparation method of narrow ditribution Gemini surface active agent described in claim 1, which is characterized in that including walking as follows
Suddenly：Acetylenic glycols are uniformly mixed with ethylene oxide first, nitrogen heterocycles catalyst is added and carries out addition reaction, you can generate narrow point
Cloth Gemini surface active agent.
4. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that acetylenic glycols and ring
The molar ratio of oxidative ethane is 1:1~20.
5. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that the acetylenic glycols
Structural formula be lower formula (II)：
In formula (II), R1、R4For C2-C12Saturated alkane in range；R2、R3For C1-C4Saturated alkane in range.
6. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that the azacyclo-
Class catalyst be 11 carbon -7- alkene (DBU) of 1,8- diazabicylos, bicyclic [2.2.2] octane (DABCO) of bis- azos of 1,4-, 1,
It is one or more in 4- diazabicylos [2.2.2] octane (ABCO), 4-dimethylaminopyridine (DMAP), triethylamine.
7. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that the azacyclo-
Class catalyst is 11 carbon -7- alkene (DBU) of 1,8- diazabicylos, bicyclic [2.2.2] octane (DABCO) of bis- azos of 1,4-, three
Ethamine is according to mass ratio 3:1:2 mix.
8. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that the azacyclo-
The addition of class catalyst is the 0.05%~2% of acetylenic glycols and ethylene oxide gross mass.
9. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that the addition is anti-
Temperature is 50~120 DEG C in the system answered, and pressure is 0.3~0.8MPa.
10. the preparation method of narrow ditribution Gemini surface active agent according to claim 3, which is characterized in that the addition
The product obtained after reaction, then carry out maturation process；The burin-in process is specially that maintenance system temperature is 50~120 DEG C, directly
No longer decline to reactor pressure, maturation process is completed.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041356A (en) * | 2019-03-27 | 2019-07-23 | 浙江润禾有机硅新材料有限公司 | A kind of twin structural polyether siloxanes and preparation method |
| WO2024002135A1 (en) * | 2022-07-01 | 2024-01-04 | 佳化化学科技发展（上海）有限公司 | Alkynyl alcohol ether and method for preparing same and use thereof |
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| US3268593A (en) * | 1961-06-26 | 1966-08-23 | Cumberland Chemical Corp | Ethylene oxide adducts of tertiary acetylenic alcohols |
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| 王淳浩: "一种用含有桥头氮化合物催化的乙氧基化新方法", 《日用化学品科学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041356A (en) * | 2019-03-27 | 2019-07-23 | 浙江润禾有机硅新材料有限公司 | A kind of twin structural polyether siloxanes and preparation method |
| WO2024002135A1 (en) * | 2022-07-01 | 2024-01-04 | 佳化化学科技发展（上海）有限公司 | Alkynyl alcohol ether and method for preparing same and use thereof |
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