CN105566626A - Preparation method of etherified capped polyether polyol - Google Patents
Preparation method of etherified capped polyether polyol Download PDFInfo
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- CN105566626A CN105566626A CN201510963079.2A CN201510963079A CN105566626A CN 105566626 A CN105566626 A CN 105566626A CN 201510963079 A CN201510963079 A CN 201510963079A CN 105566626 A CN105566626 A CN 105566626A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
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- General Chemical & Material Sciences (AREA)
- Polyethers (AREA)
Abstract
The invention belongs to the field of chemical industry, and particularly relates to a preparation method of etherified capped polyether polyol. The preparation method includes: adopting propenol as an initiator to prepare a propenol ether; enabling the propenol ether to react with a sodium methoxide solution to obtain a propenol sodium ether, and enabling the propenol sodium ether to react with allyl chloride to obtain diallyl-capped polyether. Each of two ends of a molecular structure of the etherified capped polyether polyol prepared by the method contains double bonds, so that active ingredients of copolymer are increased. The polyether containing the double bonds is used for reacting with certain macromolecular compounds like hydrogen-containing silicone oil to prepare various polyether modified compounds, and a main reaction is addition reaction between alkenyl on the polyether containing the double bonds and the macromolecular compounds and generates Si-C bonds. The obtained diallyl-capped polyether is high in double bond content, so that the active ingredients of the copolymer are increased; the polyether can be allowed to react with certain macromolecular compounds to prepare various polyether modified compounds, so that generated silicone-containing surfactant macromolecular compounds are less prone to hydrolysis and high in stability.
Description
Technical field
The invention belongs to chemical field, be specifically related to a kind of preparation method of Etherified End Group Capped Polyether polyvalent alcohol.
Background technology
Polyethers end-blocking refers to that the hydroxyl on polyethers carries out etherificate or esterification by various organic micromolecule compound, and the reactive hydrogen on hydroxyl is by the alkyl of various short chain, and aralkyl or ester group replace.After end-blocking, the essential property of polyethers is constant, only increases the performance that some is new.
Etherified End Group Capped Polyether has following structure R
1o (C
2h
4o) x (C
3h
6o) yR
2, R
1r
2for alkyl (comprising stable hydrocarbon and unsaturated hydrocarbons), there is the general character of general polyethers.End capped polyether can by selecting different initiators, and different block methods, different oxyethane, propylene oxide ratio and different capping groups, obtain the end capped polyether of various structure, character.
End-blocking for its terminal hydroxy group of polyethers containing double bond is then separately meaningful.The general polyethers containing double bond is all used to some macromolecular cpd as Silicon Containing Hydrogen wet goods reacts, make various polyether-modified compound, its main reaction is the addition reaction containing the thiazolinyl on double bond polyethers and macromolecular cpd, generate Si-C key, the compound not facile hydrolysis generated, good stability.And the alkenyl polyether of non-end-blocking is due to the existence of hydroxyl, inevitably generate Si-O-C key, and easily cause crosslinked in the copolymer, quality product is declined.Therefore be necessary hydroxy-end capped with the effective constituent improving multipolymer before reaction.
In order to by hydroxy-end capped with the effective constituent improving multipolymer, and improve the double bond content of end capped polyether, we need to develop a kind of end capped polyether containing double propenyl simultaneously.Be used for reacting with some macromolecular cpd, make various polyether-modified compound, make the silicon-containing surfactant macromole not facile hydrolysis of generation, good stability.
Summary of the invention
For the deficiencies in the prior art, the object of this invention is to provide a kind of preparation method of Etherified End Group Capped Polyether polyvalent alcohol, double bond content is high, itself and some macromolecular cpd can be reacted, make various polyether-modified compound, make the compound not facile hydrolysis of generation, good stability.
The preparation method of Etherified End Group Capped Polyether polyvalent alcohol of the present invention, adopts vinylcarbinol to be that initiator prepares propylene alcohol ether; Again this propylene alcohol ether and sodium methoxide solution are obtained by reacting propylene sodium alkoxide ether, then propylene sodium alkoxide ether and chlorallylene are obtained by reacting the polyethers of double propenyl end-blocking.
The polyethers double bond content of the double propenyl end-blocking that the present invention prepares is high, improves the effective constituent of multipolymer, itself and some macromolecular cpd can be reacted, make various polyether-modified compound, makes the compound not facile hydrolysis of generation, good stability.
Wherein:
Vinylcarbinol is adopted to be that initiator is prepared propylene alcohol ether and is: vinylcarbinol reacts with propylene oxide (PO) and oxyethane (EO) under catalyst makes propylene alcohol ether.The molecular weight of propylene alcohol ether is preferably 500-600g/mol.
Vinylcarbinol molecular structure is simple and containing double bond, the present invention selects vinylcarbinol as the initiator raw material of end capped polyether, selects suitable catalyzer, reacts under suitable conditions with PO and EO, generates propylene alcohol ether.In the present invention, because consider the sterically hindered of the propylene alcohol ether aggregated into and viscosity problem, molecular weight can not be too large, preferably controls at 500 ~ 600g/mol.Then hydroxyl is used vinylcarbinol end-blocking, obtain the polymkeric substance containing double bond structure.Catalyzer used is one or more in propylene potassium alcoholate, propylene sodium alkoxide, Lithium Aluminium Hydride, boron trifluoride diethyl etherate, preferred propylene potassium alcoholate.
Prepare in the process of propylene alcohol ether: propylene oxide and oxyethane feeding temperature≤40 DEG C, polymeric reaction temperature controls at 90-95 DEG C, polyreaction 1 ~ 3 hour, then carries out the reaction of interior pressure, and temperature controls at 90-95 DEG C, reaction times 1.5-2.5 hour; Interior pressure reaction, for being pressurized to 0.38MPa, carries out Pressure Drop to 0.1MPa with reaction.
Being prepared as of propylene sodium alkoxide ether: propylene alcohol ether and sodium methoxide solution are reacted, temperature controls at 100 DEG C-120 DEG C, preferably 100 DEG C, vacuumizes the methyl alcohol in methanol removal sodium solution and reacts the methyl alcohol generated.The temperature vacuumized controls at 100 DEG C-110 DEG C, and pressure-controlling is at-0.08 ~-0.09MPa, and the time is 1 ~ 3h.Sodium methoxide solution is commercially available prod, to the not requirement of its concentration.
Being prepared as of the polyethers of double propenyl end-blocking: propylene sodium alkoxide ether and chlorallylene are reacted, is warming up to 80 ~ 90 DEG C, make still pressure remain on 0.35 ~ 0.40MPa, reaction 1 ~ 2h, after completion of the reaction, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof.
Use sorbent treatment again after propylene sodium alkoxide ether and chlorallylene being obtained by reacting the polyethers of double propenyl end-blocking, filter the polyethers obtaining double propenyl end-blocking; Sorbent material is one or more in Magnesium Silicate q-agent, pure aluminium silicate, neusilin or diatomite, preferred neusilin.
As the preferred technical scheme of one, the preparation method of Etherified End Group Capped Polyether polyvalent alcohol of the present invention, comprises the following steps:
1) in stainless steel cauldron, add catalyzer, after nitrogen replacement, suck vinylcarbinol with suction pipe, open and stir, temperature≤30 DEG C; Heat up and dewater half an hour, temperature 35-40 DEG C; At 35-40 DEG C, add propylene oxide and oxyethane with the feed rate of 800g/h, heat up and make polymeric reaction temperature at 90-95 DEG C; Then in, pressure reacts half an hour, temperature 90-95 DEG C; Be cooled to 50 DEG C, add sorbent material and carry out aftertreatment, obtain the propylene alcohol ether of molecular weight 500 ~ 600g/mol;
2) in rotary film evaporator, add propylene alcohol ether and sodium methoxide solution that step (1) obtains, temperature of reaction controls at 100 DEG C-120 DEG C, the methyl alcohol vacuumizing the methyl alcohol in methanol removal sodium solution and generate in reacting, vaporization temperature controls at 100 DEG C-110 DEG C, pressure is at-0.08 ~-0.09MPa, time is 1 ~ 3h, material is cooled to 50 DEG C with bottom discharge;
3) material in step (2) is transferred to stainless steel cauldron, chlorallylene is added in still, be warming up to 80 DEG C, still pressure is made to remain on 0.35 ~ 0.40MPa, reaction 1 ~ 2h, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof, be cooled to 50 DEG C of dischargings, obtain the polyethers crude product of double propenyl end-blocking, polyethers crude product sorbent material is carried out aftertreatment, the refining polyethers obtaining double propenyl end-blocking.
Propylene oxide is added and oxyethane adds propylene oxide and oxyethane with the feed rate of 800g/h in step (1).
The preferred 3L of stainless steel cauldron.
Rotary film evaporator used in step (2) is ZFA-0a type rotary film evaporator.
The reaction equation of step (1) is:
The reaction equation of step (2) is:
The reaction equation of step (3) is:
In sum, the present invention has the following advantages:
Double bond is all contained in Etherified End Group Capped Polyether polyol molecule structure two ends prepared by the present invention, improves the effective constituent of multipolymer.Polyethers containing double bond is used for and some macromolecular cpd reacts as Silicon Containing Hydrogen wet goods, makes various polyether-modified compound, and its main reaction is the addition reaction containing the thiazolinyl on double bond polyethers and macromolecular cpd, generates Si-C key.The end capped polyether of the double propenyl obtained, double bond content is high, improves the effective constituent of multipolymer, itself and some macromolecular cpd can be reacted, make various polyether-modified compound, makes the compound not facile hydrolysis of generation, good stability.
Embodiment
Below in conjunction with embodiment, the present invention will be further described.
Embodiment 1
(1) in 3L stainless steel cauldron, add propylene potassium alcoholate, after nitrogen replacement oxygen level is qualified, suck vinylcarbinol with suction pipe, open and stir, temperature 30 DEG C; Heat up and dewater half an hour, temperature 35 DEG C; Add PO and EO with comparatively jogging speed at 35 DEG C, heating up gradually makes polymeric reaction temperature at 90 DEG C; Then in, pressure reacts half an hour, temperature 90 DEG C; Be cooled to 50 DEG C, sampling detects; Qualified rear refining, add sorbent material and carry out aftertreatment, obtain the propylene alcohol ether of molecular weight 500g/mol.
(2) in ZFA-0a type rotary film evaporator, add calculated amount propylene alcohol ether and sodium methoxide solution, temperature of reaction controls at 100 ± 3 DEG C.Vacuumize the methyl alcohol generated in methyl alcohol in methanol removal sodium solution and alcohol permutoid reaction, separating methanol temperature controls at 105 ± 3 DEG C, and gauge pressure is at-0.085MPa, and the time is 1h.Material is cooled to 50 DEG C with bottom discharge.
(3) material in step 2 is transferred to 3L stainless steel cauldron.In still, add chlorallylene, be warming up to 80 DEG C, make still pressure remain on 0.38MPa, react about 2h, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof, be cooled to 50 DEG C of dischargings, obtain the polyethers crude product of double propenyl end-blocking.Polyethers crude product sorbent material neusilin is carried out aftertreatment and refines the polyethers A obtaining double propenyl end-blocking.
Embodiment 2
(1) in 3L stainless steel cauldron, add propylene sodium alkoxide, after nitrogen replacement oxygen level is qualified, suck vinylcarbinol with suction pipe, open and stir, temperature 28 DEG C; Heat up and dewater half an hour, temperature 38 DEG C; Add PO and EO with comparatively jogging speed at 38 DEG C, heating up gradually makes polymeric reaction temperature at 93 DEG C; Then in, pressure reacts half an hour, temperature 93 DEG C; Be cooled to 50 DEG C, sampling detects; Qualified rear refining, add sorbent material and carry out aftertreatment, obtain the propylene alcohol ether of molecular weight 550g/mol.
(2) in ZFA-0a type rotary film evaporator, add calculated amount propylene alcohol ether and sodium methoxide solution, temperature of reaction controls at 110 ± 3 DEG C.Vacuumize the methyl alcohol generated in methyl alcohol in methanol removal sodium solution and alcohol permutoid reaction, separating methanol temperature controls at 100 ± 3 DEG C, and gauge pressure is at-0.08MPa, and the time is 2h.Material is cooled to 50 DEG C with bottom discharge.
(3) material in step 2 is transferred to 3L stainless steel cauldron.In still, add chlorallylene, be warming up to 80 DEG C, make still pressure remain on 0.40MPa, react about 1h, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof, be cooled to 50 DEG C of dischargings, obtain the polyethers crude product of double propenyl end-blocking.Polyethers crude product sorbent material Magnesium Silicate q-agent is carried out aftertreatment and refines the polyethers B obtaining double propenyl end-blocking.
Embodiment 3
(1) in 3L stainless steel cauldron, add Lithium Aluminium Hydride, after nitrogen replacement oxygen level is qualified, suck vinylcarbinol with suction pipe, open and stir, temperature 25 DEG C; Heat up and dewater half an hour, temperature 40 DEG C; Add PO and EO with comparatively jogging speed at 40 DEG C, heating up gradually makes polymeric reaction temperature at 95 DEG C; Then in, pressure reacts half an hour, temperature 95 DEG C; Be cooled to 50 DEG C, sampling detects; Qualified rear refining, add sorbent material and carry out aftertreatment, obtain the propylene alcohol ether of molecular weight 600g/mol.
(2) in ZFA-0a type rotary film evaporator, add calculated amount propylene alcohol ether and sodium methoxide solution, temperature of reaction controls at 120 ± 3 DEG C.Vacuumize the methyl alcohol generated in methyl alcohol in methanol removal sodium solution and alcohol permutoid reaction, separating methanol temperature controls at 110 ± 3 DEG C, and gauge pressure is at-0.09MPa, and the time is 1.5h.Material is cooled to 50 DEG C with bottom discharge.
(3) material in step 2 is transferred to 3L stainless steel cauldron.In still, add chlorallylene, be warming up to 80 DEG C, make still pressure remain on 0.35MPa, react about 1.5h, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof, be cooled to 50 DEG C of dischargings, obtain the polyethers crude product of double propenyl end-blocking.Polyethers crude product sorbent material pure aluminium silicate is carried out aftertreatment and refines the polyethers C obtaining double propenyl end-blocking.
Comparative example 1
In 3L stainless steel cauldron, add propylene potassium alcoholate, after nitrogen replacement oxygen level is qualified, suck vinylcarbinol with suction pipe, open and stir, temperature 30 DEG C; Heat up, dehydration, half an hour time, temperature 35 DEG C; PO and EO charging, temperature 90 DEG C; Then in, pressure reacts half an hour, temperature 90 DEG C; Be cooled to 90 DEG C, sampling detects; Qualified rear refining, polyethers crude product sorbent material diatomite is carried out aftertreatment is refining obtains propylene alcohol ether D.
Polyethers A, B, C of double propenyl end-blocking prepared by embodiment 1-3 and comparative example 1 and the performance index list of propylene alcohol ether D are in table 1.
Polyethers A, B, C of table 1 double propenyl end-blocking and the performance index of propylene alcohol ether D
Because hydroxyl is by propenyl end-blocking, ideally not hydroxyl in product, therefore also do not have hydroxyl value in quality index.But there is the incomplete situation of end-blocking in experimentation, find out from the analytical results of performance index, in index, also measured a small amount of hydroxyl value.In addition, double propenyl product improves a lot relative to propylene alcohol ether unsaturated value.The Etherified End Group Capped Polyether polyvalent alcohol of the propylene alcohol ether containing double propenyl prepared by the present invention, because double bond end-blocking is all contained at its two ends, double propenyl product improves a lot relative to propylene alcohol ether unsaturated value, the Application Areas of easily extensible polyether glycol, give the added value that product is higher, by the larger economic benefit of generation and social benefit.
Claims (9)
1. a preparation method for Etherified End Group Capped Polyether polyvalent alcohol, is characterized in that: adopt vinylcarbinol to be that initiator prepares propylene alcohol ether; Again this propylene alcohol ether and sodium methoxide solution are obtained by reacting propylene sodium alkoxide ether, then propylene sodium alkoxide ether and chlorallylene are obtained by reacting the polyethers of double propenyl end-blocking.
2. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 1, is characterized in that: adopt vinylcarbinol to be that initiator is prepared propylene alcohol ether and is: vinylcarbinol makes propylene alcohol ether with propylene oxide and reacting ethylene oxide under catalyst.
3. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 2, is characterized in that: the molecular weight of propylene alcohol ether is 500-600g/mol.
4. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 2, is characterized in that: catalyzer is one or more in propylene potassium alcoholate, propylene sodium alkoxide, Lithium Aluminium Hydride, boron trifluoride diethyl etherate.
5. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 2, it is characterized in that: propylene oxide and oxyethane feeding temperature≤40 DEG C, polymeric reaction temperature controls at 90-95 DEG C, polyreaction 1 ~ 3 hour, carry out the reaction of interior pressure again, temperature controls at 90-95 DEG C, reaction times 1.5-2.5 hour.
6. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 1, it is characterized in that: being prepared as of propylene sodium alkoxide ether: propylene alcohol ether and sodium methoxide solution are reacted, temperature controls at 100 DEG C-120 DEG C, vacuumizes the methyl alcohol in methanol removal sodium solution and reacts the methyl alcohol generated; The temperature vacuumized controls at 100 DEG C-110 DEG C, and pressure-controlling is at-0.08 ~-0.09MPa, and the time is 1 ~ 3h.
7. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 1, it is characterized in that: being prepared as of the polyethers of double propenyl end-blocking: propylene sodium alkoxide ether and chlorallylene are reacted, be warming up to 80 ~ 90 DEG C, still pressure is made to remain on 0.35 ~ 0.40MPa, reaction 1 ~ 2h, after completion of the reaction, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof.
8. the preparation method of Etherified End Group Capped Polyether polyvalent alcohol according to claim 1, is characterized in that: use sorbent treatment again after propylene sodium alkoxide ether and chlorallylene being obtained by reacting the polyethers of double propenyl end-blocking, filters the polyethers obtaining double propenyl end-blocking; Sorbent material is one or more in Magnesium Silicate q-agent, pure aluminium silicate, neusilin or diatomite.
9., according to the preparation method of the arbitrary described Etherified End Group Capped Polyether polyvalent alcohol of claim 1-8, it is characterized in that: comprise the following steps:
1) in stainless steel cauldron, add catalyzer, after nitrogen replacement, suck vinylcarbinol with suction pipe, open and stir, temperature≤30 DEG C; Heat up and dewater half an hour, temperature 35-40 DEG C; At 35-40 DEG C, add propylene oxide and oxyethane with the feed rate of 800g/h, heat up and make polymeric reaction temperature at 90-95 DEG C; Then in, pressure reacts half an hour, temperature 90-95 DEG C; Be cooled to 50 DEG C, add sorbent material and carry out aftertreatment, obtain the propylene alcohol ether of molecular weight 500 ~ 600g/mol;
2) in rotary film evaporator, add propylene alcohol ether and sodium methoxide solution that step (1) obtains, temperature of reaction controls at 100 DEG C-120 DEG C, the methyl alcohol vacuumizing the methyl alcohol in methanol removal sodium solution and generate in reacting, vaporization temperature controls at 100 DEG C-110 DEG C, pressure is at-0.08 ~-0.09MPa, time is 1 ~ 3h, material is cooled to 50 DEG C with bottom discharge;
3) material in step (2) is transferred to stainless steel cauldron, chlorallylene is added in still, be warming up to 80 DEG C, still pressure is made to remain on 0.35 ~ 0.40MPa, reaction 1 ~ 2h, the chlorallylene that removed under reduced pressure is excessive and volatile constituent thereof, be cooled to 50 DEG C of dischargings, obtain the polyethers crude product of double propenyl end-blocking, polyethers crude product sorbent material is carried out aftertreatment, the refining polyethers obtaining double propenyl end-blocking.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279663A (en) * | 2016-07-30 | 2017-01-04 | 淄博德信联邦化学工业有限公司 | The preparation method of viscosifier polyether polyol |
| CN112794959A (en) * | 2021-01-29 | 2021-05-14 | 武汉理工大学 | Polymer for stabilizing pumped concrete and preparation method thereof |
| CN113024694A (en) * | 2021-03-30 | 2021-06-25 | 浙江皇马科技股份有限公司 | Method for removing boron trifluoride or complexes thereof from organic matters |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504241A (en) * | 2011-11-02 | 2012-06-20 | 浙江皇马科技股份有限公司 | Method for synthetizing diallyl polyether |
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- 2015-12-18 CN CN201510963079.2A patent/CN105566626A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102504241A (en) * | 2011-11-02 | 2012-06-20 | 浙江皇马科技股份有限公司 | Method for synthetizing diallyl polyether |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279663A (en) * | 2016-07-30 | 2017-01-04 | 淄博德信联邦化学工业有限公司 | The preparation method of viscosifier polyether polyol |
| CN112794959A (en) * | 2021-01-29 | 2021-05-14 | 武汉理工大学 | Polymer for stabilizing pumped concrete and preparation method thereof |
| CN113024694A (en) * | 2021-03-30 | 2021-06-25 | 浙江皇马科技股份有限公司 | Method for removing boron trifluoride or complexes thereof from organic matters |
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Application publication date: 20160511 |