CN110343239A - The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol - Google Patents
The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol Download PDFInfo
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- CN110343239A CN110343239A CN201910758043.9A CN201910758043A CN110343239A CN 110343239 A CN110343239 A CN 110343239A CN 201910758043 A CN201910758043 A CN 201910758043A CN 110343239 A CN110343239 A CN 110343239A
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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
- C08G65/26—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
- C08G65/2612—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 aromatic or arylaliphatic 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
- C08G65/26—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
- C08G65/2642—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 characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
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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
- C08G65/2642—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 characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2675—Phosphorus or compounds thereof
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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
- C08G65/2642—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 characterised by the catalyst used
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
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Abstract
The invention belongs to polyether polyol synthesis technical fields, are specifically related to a kind of synthetic method of low-unsaturation-degree aromatic polyether polyalcohol.First with small molecule polyol or polyamine and propylene oxide synthetic intermediate under the action of base metal catalysts containing active hydrogen, then intermediate reacts with propylene oxide and low-unsaturation-degree aromatic polyether polyalcohol is prepared again with bisphenol-A under the action of bimetallic catalyst and bronsted acid catalyst.The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol of the present invention, using bisphenol-A as initiator, distribution catalysis prepares the aromatic polyether polyalcohol of low-unsaturation-degree, the aromatic polyether polyalcohol of preparation is easy to get with raw material, simple process is easy to implement, it is few to generate the three wastes, economic value is high, the advantage of product environmental protection.
Description
Technical field
The invention belongs to polyether polyol synthesis technical fields, and it is more to be specifically related to a kind of low-unsaturation-degree aromatic polyether
The synthetic method of first alcohol.
Background technique
Polyether polyol is that main chain contains ehter bond (- R-O-R-), and end group or side group contain low greater than 2 hydroxyls (- OH)
Polymers.Using low molecular weight polyols, polyamine or compound containing active hydrogen as initiator, with oxyalkylene in catalyst action
Lower ring-opening polymerisation forms.The polyether polyol of different degrees of functionality can be made in the number of the active atomic according to contained by initiator.
There are many preparation method of polyether polyol, mainly include anionic polymerisation, cationic polymerization and coordination polymerization etc..Yin
Ionic polymerization is catalyst using inorganic strong alkali (such as KOH), and inorganic strong alkali has inexpensive, the easy removing in polyether polyol
Etc. advantages, prepare low molecular weight polyether polyol when be widely used in industrial production.However, inorganic strong alkali is easy
Make propylene oxide occur isomerization, generate end be unsaturated double-bond monohydroxy polyethers, make polyether polyol degree of functionality and
Relative molecular weight becomes smaller；And the process for needing to refine, it is also easy to produce dangerous waste largely containing inorganic salts, causes environmental pollution.
Cationic polymerization is catalyst using strong lewis acid (such as BF3 ether), carries out meeting when oxyalkylene polymerization
The by-product for forming dioxanes structure, has detrimental effect to the performance of the polyurethane product of preparation, needs to utilize cumbersome mistake
Journey removes impurity, does not use substantially in industrial production.
Although double metal cyanide catalyst its be used for propylene oxide homopolymerization and ethylene oxide/propylene oxide is random
Activity is very high when combined polymerization, and the polyether polyol low molecular weight compared with narrow ditribution can be made.But there is cannot directly adopt it is small
The polyalcohol of molecule is initiator, needs the shortcomings that originating indirectly using the polyether polyol of low molecular weight.
Aromatic polyether polyalcohol refers generally to the polyether polyol containing phenyl ring, the polyether polyol containing phenyl ring have it is heat-resisting,
The features such as fire-retardant.When preparing low-unsaturation-degree aromatic polyether polyalcohol using the above method, it is longer that there are catalyst induction periods,
Initiator metallic catalyst influences greatly catalyst performance, and the three wastes of generation are more, the cumbersome problem of technical process, it would therefore be highly desirable to
Explore a kind of synthetic method of novel low-unsaturation-degree aromatic polyether polyalcohol.
Summary of the invention
The technical problem to be solved by the present invention is overcoming the deficiencies of the prior art and provide a kind of low-unsaturation-degree aromatic series
The synthetic method of polyether polyol.For the synthetic method using bisphenol-A as initiator, substep catalysis prepares the aromatic series of low-unsaturation-degree
The aromatic polyether polyalcohol of polyether polyol, preparation is easy to get with raw material, and simple process is easy to implement, and the generation three wastes are few, warp
Ji value is high, the advantage of product environmental protection.
The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol of the present invention, first with small point containing active hydrogen
Sub- polyalcohol or polyamine and propylene oxide synthetic intermediate under the action of base metal catalysts, then intermediate again with bis-phenol
A reacts with propylene oxide and low-unsaturation-degree aromatic series is prepared under the action of bimetallic catalyst and bronsted acid catalyst
Polyether polyol.
As a preferred technical solution, the synthesis side of low-unsaturation-degree aromatic polyether polyalcohol of the present invention
Method, specifically includes the following steps:
(1) small molecule polyol or polyamine and base metal catalysts are put into autoclave, nitrogen displacement 3-5 times,
It is warming up to 90-110 DEG C, is reacted with propylene oxide, cures 2.5-3h, demonomerization 1-1.5h after reaction, cool down refining filtering
Obtain intermediate；
(2) intermediate, bisphenol-A, bimetallic catalyst and the bronsted acid catalyst investment high pressure step (1) being prepared
Reaction kettle, nitrogen displacement 3-5 times are warming up to 110-120 DEG C of dehydration 2-2.5h, measure moisture < 0.02%, put into propylene oxide
It is reacted, cures 2.5-3h, demonomerization 1-1.5h after reaction, cool down blowing, and low unsaturation is prepared in strainer filtering
Spend aromatic polyether polyalcohol.
Wherein:
Propylene oxide distribution is added, and the propylene oxide being added in step (1) accounts for the 53%-77% of propylene oxide gross mass；
Remaining propylene oxide is added in step (2).
The propylene oxide of step (2) is added in two steps, is firstly added the 3-8.5% for accounting for step (2) oxypropylene quality,
Induced reaction is carried out, remaining propylene oxide is then added and carries out polymerization reaction.
Reaction temperature is 120-150 DEG C in step (2).
Small molecule polyol described in step (1) or polyamine be propylene glycol, ethylene glycol, dipropylene glycol, diethylene glycol,
One of diethanol amine, glycerol, triethanolamine, trimethylolpropane, pentaerythrite, sorbierite or sucrose are a variety of.
Base metal catalysts are KOH or NaOH in step (1), and the quality of base metal catalysts accounts for the first step in step (1)
The 0.24-0.30% of total mass of raw material.
Bronsted acid catalyst described in step (2) is phosphoric acid.
The quality of bimetallic catalyst (DMC) and bronsted acid catalyst and total mass of raw material in second step is accounted in step (2)
30-33ppm.
The mass ratio of small molecule alcohol or polyamine and propylene oxide is 1:6-8.
The mass ratio of bisphenol-A and intermediate is 1:1-1:4.
The mesh number of the strainer used in step (2) is 400 mesh.
The hydroxyl value of intermediate is 275-285mgKOH/g.
The low-unsaturation-degree aromatic polyether polyalcohol hydroxyl value being prepared is 100-200mgKOH/g.
Bisphenol-A is also known as diphenol propane, is a kind of important Organic Chemicals, is widely used in production polycarbonate, ring
The high molecular materials such as oxygen resin, it can also be used to plasticizer, fire retardant, antioxidant and heat stabilizer.
Compared with the prior art, the present invention has the following beneficial effects:
The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol of the present invention, using bisphenol-A as initiator, substep
Catalysis prepares the aromatic polyether polyalcohol of low-unsaturation-degree, and the aromatic polyether polyalcohol of preparation is easy to get with raw material, technique
Simple easy to implement, the generation three wastes are few, and economic value is high, the advantage of product environmental protection.
Specific embodiment
The invention will be further described with reference to embodiments.
Embodiment 1
The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol of the present invention, first with small point containing active hydrogen
Sub- polyalcohol or polyamine and propylene oxide synthetic intermediate A under the action of base metal catalysts, then intermediate A again with it is double
Phenol A reacts with propylene oxide and low-unsaturation-degree fragrance is prepared under the action of bimetallic catalyst and bronsted acid catalyst
Adoption ethoxylated polyhydric alcohol.
The specific synthesis step of low-unsaturation-degree aromatic polyether polyalcohol is as follows:
(1) by 400g propylene glycol, 5.3gKOH is put at room temperature in 5L autoclave, and nitrogen is replaced 5 times, is heated up 90 DEG C
It reacts with 1700gPO, cures demonomerization 1 hour 3 hours after reaction, cooling refining filtering obtains intermediate A, intermediate A
OHV is 280.5mgKOH.
(2) by 400g intermediate A, 200g bisphenol-A, 0.06gDMC, 0.004g phosphoric acid put into 5L autoclave, nitrogen
Displacement 5 times, heats up 110 DEG C and is dehydrated 2 hours, measures moisture less than 0.02%, and investment 50gPO carries out induced reaction, induces successfully
It puts into 1430gPO again afterwards to react, 120 DEG C of reaction temperature, cure 2 hours after reaction, demonomerization 1 hour, cooling was put
Material, is obtained by filtration low-unsaturation-degree aromatic polyether polyalcohol with 400 mesh filter screens, it is polynary to measure low-unsaturation-degree aromatic polyether
The OHV of alcohol is 100.9mgKOH, and VIS is 968mpa.s (25 DEG C).
Embodiment 2
The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol of the present invention, first with small point containing active hydrogen
Sub- polyalcohol or polyamine and propylene oxide synthetic intermediate B under the action of base metal catalysts, then intermediate B again with it is double
Phenol A reacts with propylene oxide and low-unsaturation-degree fragrance is prepared under the action of bimetallic catalyst and bronsted acid catalyst
Adoption ethoxylated polyhydric alcohol.
The specific synthesis step of low-unsaturation-degree aromatic polyether polyalcohol is as follows:
(1) by 400g glycerol, 6.5gNaOH is put at room temperature in 5L autoclave, and nitrogen is replaced 4 times, is heated up 100 DEG C
It reacts with 2200gPO, cures demonomerization 1 hour 3 hours after reaction, cooling refining filtering obtains intermediate B, intermediate B
OHV is 280.1mgKOH.
(2) by 400g intermediate B, 400g bisphenol-A, 0.046gDMC, 0.004g phosphoric acid put into 5L autoclave, nitrogen
Gas is replaced 4 times, and heating up 120 DEG C to be dehydrated measures moisture for 2 hours less than 0.02%, and investment 50gPO carries out induced reaction, induces successfully
It puts into 700gPO again afterwards to react, 150 DEG C of reaction temperature, cure 2 hours after reaction, demonomerization 1 hour, cooling was put
Material, is obtained by filtration to obtain low-unsaturation-degree aromatic polyether polyalcohol with 400 mesh filter screens, measures low-unsaturation-degree aromatic polyether
The OHV of polyalcohol is 198.9mgKOH, and VIS is 653mpa.s (25 DEG C).
Embodiment 3
The synthetic method of low-unsaturation-degree aromatic polyether polyalcohol of the present invention, first with small point containing active hydrogen
Sub- polyalcohol or polyamine and propylene oxide synthetic intermediate C under the action of base metal catalysts, then intermediate C again with it is double
Phenol A reacts with propylene oxide and low-unsaturation-degree fragrance is prepared under the action of bimetallic catalyst and bronsted acid catalyst
Adoption ethoxylated polyhydric alcohol.
The specific synthesis step of low-unsaturation-degree aromatic polyether polyalcohol is as follows:
(1) by 400g pentaerythrite, 7gKOH is put at room temperature in 5L autoclave, and nitrogen is replaced 3 times, is heated up 110 DEG C
It reacts with 1915gPO, cures demonomerization 1 hour 3 hours after reaction, cooling refining filtering obtains intermediate C, intermediate C's
OHV is 284.8mgKOH.
(2) by 400g intermediate C, 100g bisphenol-A, 0.032gDMC, 0.004g phosphoric acid is put into 5L autoclave, nitrogen
Gas is replaced 3 times, and heating up 120 DEG C to be dehydrated measures moisture for 2 hours less than 0.02%, and investment 50gPO carries out induced reaction, induces successfully
It puts into 550gPO again afterwards to react, 140 DEG C of reaction temperature, cure 2 hours after reaction, demonomerization 1 hour, cooling was put
Material, is obtained by filtration low-unsaturation-degree aromatic polyether polyalcohol with 400 mesh filter screens, it is polynary to measure low-unsaturation-degree aromatic polyether
The OHV of alcohol is 149.1mgKOH, and VIS is 759mpa.s (25 DEG C).
Claims (10)
1. a kind of synthetic method of low-unsaturation-degree aromatic polyether polyalcohol, it is characterised in that: first containing the small of active hydrogen
Molecular polylol or polyamine and propylene oxide synthetic intermediate under the action of base metal catalysts, then intermediate again with it is double
Phenol A reacts with propylene oxide and low-unsaturation-degree fragrance is prepared under the action of bimetallic catalyst and bronsted acid catalyst
Adoption ethoxylated polyhydric alcohol.
2. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 1, it is characterised in that: specific
The following steps are included:
(1) small molecule polyol or polyamine and base metal catalysts are put into autoclave, nitrogen displacement 3-5 times, heating
It to 90-110 DEG C, is reacted with propylene oxide, cures 2.5-3h, demonomerization 1-1.5h after reaction, cooling refining filtering obtains
Intermediate；
(2) intermediate, bisphenol-A, bimetallic catalyst and the bronsted acid catalyst investment reaction under high pressure step (1) being prepared
Kettle, nitrogen displacement 3-5 times are warming up to 110-120 DEG C of dehydration 2-2.5h, measure moisture < 0.02%, and investment propylene oxide carries out
Reaction cures 2.5-3h, demonomerization 1-1.5h after reaction, and cool down blowing, and low-unsaturation-degree virtue is prepared in strainer filtering
Fragrant adoption ethoxylated polyhydric alcohol.
3. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 2, it is characterised in that: epoxy
Propane distribution is added, and the propylene oxide being added in step (1) accounts for the 53%-77% of propylene oxide gross mass；It is added in step (2)
Remaining propylene oxide.
4. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 3, it is characterised in that: step
(2) propylene oxide is added in two steps, is firstly added the 3-8.5% for accounting for step (2) oxypropylene quality, induce anti-
It answers, then adds remaining propylene oxide and carry out polymerization reaction.
5. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 2, it is characterised in that: step
(2) reaction temperature is 120-150 DEG C in.
6. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 1, it is characterised in that: step
(1) small molecule polyol or polyamine described in be propylene glycol, ethylene glycol, dipropylene glycol, diethylene glycol, diethanol amine, sweet
One of oil, triethanolamine, trimethylolpropane, pentaerythrite, sorbierite or sucrose are a variety of.
7. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 1, it is characterised in that: step
(1) base metal catalysts are KOH or NaOH in, and the quality of base metal catalysts accounts for first step total mass of raw material in step (1)
0.24-0.30%；The quality of bimetallic catalyst and bronsted acid catalyst and total mass of raw material in second step is accounted in step (2)
30-33ppm。
8. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 1, it is characterised in that: small point
The mass ratio of sub- alcohols or polyamine and propylene oxide is 1:6-8；The mass ratio of bisphenol-A and intermediate is 1:1-1:4.
9. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 2, it is characterised in that: step
(2) mesh number of the strainer used in is 400 mesh.
10. the synthetic method of low-unsaturation-degree aromatic polyether polyalcohol according to claim 1, it is characterised in that: in
The hydroxyl value of mesosome is 275-285mgKOH/g；The low-unsaturation-degree aromatic polyether polyalcohol hydroxyl value being prepared is 100-
200mgKOH/g。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818889A (en) * | 2019-11-15 | 2020-02-21 | 山东蓝星东大有限公司 | Synthesis method of micromolecular polyether polyol with narrow molecular weight distribution |
| CN111019587A (en) * | 2019-12-17 | 2020-04-17 | 格丽泰新材料科技（苏州）有限公司 | Two-component polyurethane adhesive for bonding power battery and preparation method thereof |
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2019
- 2019-08-16 CN CN201910758043.9A patent/CN110343239A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818889A (en) * | 2019-11-15 | 2020-02-21 | 山东蓝星东大有限公司 | Synthesis method of micromolecular polyether polyol with narrow molecular weight distribution |
| CN111019587A (en) * | 2019-12-17 | 2020-04-17 | 格丽泰新材料科技（苏州）有限公司 | Two-component polyurethane adhesive for bonding power battery and preparation method thereof |
| CN111019587B (en) * | 2019-12-17 | 2022-04-12 | 格丽泰新材料科技（苏州）有限公司 | Two-component polyurethane adhesive for bonding power battery and preparation method thereof |
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Application publication date: 20191018 |