CN113698587A - Preparation method of hard foam polyether polyol - Google Patents
Preparation method of hard foam polyether polyol Download PDFInfo
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- CN113698587A CN113698587A CN202111048197.2A CN202111048197A CN113698587A CN 113698587 A CN113698587 A CN 113698587A CN 202111048197 A CN202111048197 A CN 202111048197A CN 113698587 A CN113698587 A CN 113698587A
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
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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
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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
- C08G65/2615—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 the other compounds containing carboxylic acid, ester or anhydride 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
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen 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
- C08G65/2696—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 process or apparatus used
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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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
Abstract
The invention discloses a preparation method of hard foam polyether polyol, and belongs to the technical field of polyether polyol synthesis. The invention comprises the following steps: (1) modification of palm oil: adding palm oil and small molecular alcohol compounds into a reaction kettle, replacing with nitrogen, controlling the reaction temperature at 90-140 ℃, and modifying the palm oil under the catalysis of an amine catalyst; (2) reacting the composite high-functionality initiator and the modified palm oil with an epoxy compound at 75-95 ℃ under the catalysis of a composite amine catalyst; (3) dehydrating under vacuum condition; (4) adding the rest epoxy compound at the temperature of 110-; (5) and vacuumizing to remove unreacted monomers to obtain the product. Compared with the traditional synthesis process of the hard foam polyether polyol, the method disclosed by the invention has the advantages that the consumption of propylene oxide is reduced, the production cost is reduced, and the performance of the hard foam polyether polyol in foaming application can be improved.
Description
Technical Field
The invention relates to the technical field of synthesis of polyether polyol, and particularly relates to a preparation method of hard foam polyether polyol.
Background
Polyether polyol is a polymer, the main chain of the molecule of the polyether polyol has ether bonds (-C-O-C-), and two ends of the molecular chain have partial hydroxyl groups (-OH), the polyether polyol is one of main raw materials for preparing polyurethane foam, and polyether rigid foam synthesized by the polyether polyol has the characteristics of better mechanical property and good heat insulation effect. The raw materials for traditionally producing the hard foam polyether polyol such as glycerol, propylene glycol, dipropylene glycol, pentaerythritol, sorbitol and the like are mostly from petrochemical or coal chemical products and belong to non-renewable resources, so the price is relatively high and the cost is relatively high. With the increasing maturity of polyether polyol production technology, market competition becomes more and more intense, and the requirements of polyether production plants on improving production efficiency, reducing equipment investment and reducing production cost are more and more urgent.
Palm oil is used as natural renewable oil, has rich resources, low price and complete non-toxicity of decomposition products, is widely used for preparing hard bubble polyether polyol, and can effectively reduce the dosage of epoxy compounds, thereby reducing the production cost. The preparation method commonly used at present comprises the following steps: palm oil is directly added into the hard foam polyether polyol, the compatibility of the palm oil and sucrose is poor, and the method has a shrinkage foam phenomenon in the later foaming; the other method is to modify the palm oil, and add the palm oil and the hard foam polyether polyol for mixing reaction at the later stage of the reaction, so that the palm oil and the polyether are mixed unevenly, and the foam performance is reduced during later application.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of hard foam polyether polyol, the raw materials are convenient to purchase, the modified palm oil contains certain hydroxyl and is used as an initiator to react with an epoxy compound, the dosage of the epoxy compound is reduced, the production cost is reduced, the composite high-functionality initiator and the composite amine catalyst are adopted, the prepared product does not need post-treatment, the process is simple and environment-friendly, and the performance is improved in foaming application.
In order to realize the technical purpose, the invention adopts the following scheme: the preparation method of the hard foam polyether polyol comprises the following steps:
s1, palm oil modification: adding palm oil and small molecular alcohol compounds into a reaction kettle, replacing nitrogen, adding an amine catalyst, controlling the reaction temperature to be 90-140 ℃, controlling the reaction pressure to be 0.1-0.45Mpa, and reacting for 3 hours to modify the palm oil.
S2, adding the composite high-functionality initiator and the modified palm oil into a reaction kettle, replacing with nitrogen, reacting with a section of epoxy compound at 75-95 ℃ under the catalysis of a composite amine catalyst, controlling the reaction pressure at 0.1-0.45Mpa, and curing for 1-3 hours, wherein the added section of epoxy compound accounts for 10-25% of the total mass of the polyether.
S3, after the ripening is finished, dehydrating under the vacuum condition until the moisture is qualified.
S4, continuously adding a second-stage epoxy compound, wherein the mass of the second-stage epoxy compound accounts for 30-50% of the total mass of the polyether, controlling the reaction temperature to be 110-130 ℃, the reaction pressure to be 0.1-0.45Mpa, and curing for 2-3 hours.
And S5, removing unreacted monomers by negative pressure vacuum pumping to obtain the low-cost high-performance rigid foam polyether polyol product.
Compared with the prior art, the invention has the beneficial effects that:
(1) the palm oil as a raw material is convenient to purchase, the modified palm oil contains certain hydroxyl and is used as an initiator to react with an epoxy compound, the dosage of the epoxy compound can be reduced to 50-60% from 60-70%, and the dosage of the epoxy compound is reduced, so that the production cost is reduced.
(2) The invention adopts the composite high-functionality initiator, and increases the crosslinking degree of the foam, increases the strength and improves the dimensional stability of the foam in the foaming application by changing the molecular structure of the polyether.
(3) The hard foam polyether polyol prepared by the method only adopts the amine catalyst, does not need to be subjected to aftertreatment, shortens the polymerization reaction time, improves the production efficiency, has a simple and environment-friendly process, is beneficial to market popularization and application, and has good economic significance.
The preferred scheme of the invention is as follows:
the small molecular alcohol compound in S1 is one or more of glycerol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, trimethylolpropane and pentaerythritol.
The composite high-functionality initiator in S2 is one or more of sucrose, sorbitol, xylitol, mannitol, glucose or maltose.
The amine catalyst in S1 is one or two of dimethylamine, trimethylamine, diethylamine and triethylamine, and the compound amine catalyst in S2 is any two of dimethylamine, trimethylamine, diethylamine and triethylamine.
The first-stage epoxy compound and the second-stage epoxy compound are the same epoxy compound medicament, and the epoxy compound is one or two of ethylene oxide, propylene oxide or butylene oxide.
The mole ratio of the palm oil to the small molecular alcohol compound is 1-5: 1, and the amine catalyst accounts for 0.1-0.3% of the total mass of the polyether.
The molar ratio of the composite high-functionality initiator to the modified palm oil is 1-4: 1, and the composite amine catalyst accounts for 0.2-0.6% of the total mass of the polyether.
The first-stage epoxy compound in the S2 accounts for 10-25% of the total mass of the polyether; the second-stage epoxy compound in the S4 accounts for 30-50% of the total weight of the polyether, the curing time is 1-3 h, and the curing pressure is-0.4-0 Mpa.
S3, the temperature of vacuum dehydration is 100-120 ℃, the dehydration time is 1-2.5 h, and the water content after dehydration is 0.01-0.03 wt%.
S5 the reaction temperature for removing the unreacted monomer in vacuum is 120-140 ℃, and the removal time is 1-3 h.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to fully understand the objects, features and effects of the invention, but the present invention is not limited thereto.
Example 1
1300g of palm oil with 24 degrees and 184g of glycerol are added into a 5L polymerization reaction kettle, nitrogen is replaced for 5 times, the kettle is vacuumized until the vacuum degree is-0.096 Mpa, 3.71g of dimethylamine (40 percent) is pumped, the temperature is increased to 100 to 130 ℃, the reaction is carried out for 3 hours, the modified palm oil is prepared, and the hydroxyl value is 236 mgKOH/g through analytical detection. Adding 513g of cane sugar, 273 g of sorbitol and 809.3 g of modified palm oil into a polymerization reaction kettle, replacing 5 times with nitrogen, vacuumizing until the vacuum degree is-0.096 Mpa, adding 14.4 g of dimethylamine and 7.2 g of triethylamine, heating to 85 ℃, adding 648g of propylene oxide, controlling the reaction pressure to be 0.1-0.45Mpa during the period, and curing for 2 hours. After the curing is finished, heating to 100-120 ℃, and vacuumizing and dehydrating for 2 hours. Adding the rest 1358g of propylene oxide, controlling the reaction temperature to be 110-130 ℃, the reaction pressure to be 0.1-0.45Mpa, and curing for 2-3 h. And removing unreacted monomers in vacuum at the temperature of 120-140 ℃ for 1-3 h to obtain the low-cost high-performance rigid foam polyether polyol product.
Example 2
Adding 1625g of 24-DEG palm oil and 167.5g of dipropylene glycol into a 5L polymerization reaction kettle, performing nitrogen replacement for 5 times, vacuumizing until the vacuum degree is-0.096 Mpa, pumping 4.7g of dimethylamine (40%), heating to 100-130 ℃, and reacting for 3 hours to obtain the modified palm oil, wherein the hydroxyl value is 98mgKOH/g through analytical detection. 615.6g of sucrose, 219.4 g of sorbitol and 924.3 g of modified palm oil are added into a polymerization reaction kettle, nitrogen is replaced for 5 times, the vacuum degree is vacuumized to-0.096 Mpa, 14.2 g of dimethylamine and 6.6 g of triethylamine are added, the temperature is raised to 85 ℃, 530g of propylene oxide is added, the reaction pressure is controlled to be 0.1-0.45Mpa during the period, and the mixture is cured for 2 hours. After the curing is finished, heating to 100-120 ℃, and vacuumizing and dehydrating for 2 hours. Adding the rest 1235g of propylene oxide, controlling the reaction temperature to be 110-130 ℃, controlling the pressure to be 0.1-0.45Mpa, and curing for 2-3 h. And removing unreacted monomers in vacuum at the temperature of 120-140 ℃ for 1-3 h to obtain the low-cost high-performance rigid foam polyether polyol product.
Comparative example 1
Adding 820.8 g of cane sugar, 55.2g of glycerol and 873.6g of 24-degree palm oil into a 5L polymerization reaction kettle, replacing 5 times with nitrogen, vacuumizing until the vacuum degree is-0.096 Mpa, pumping 31.5g of dimethylamine (40%), heating to 90 ℃, adding 800 g of propylene oxide, controlling the reaction pressure to be 0.1-0.45Mpa during the period, and curing for 2 hours. After the curing is finished, heating to 100-120 ℃, and vacuumizing and dehydrating for 2 hours. Adding the residual 950g of propylene oxide, controlling the reaction temperature to be 110-130 ℃, the pressure to be 0.1-0.45Mpa, and curing for 2-3 h. And removing unreacted monomers in vacuum at the temperature of 120-140 ℃ for 1-3 h to obtain the hard foam polyether polyol product.
Comparative example 2
Adding 1170 g of palm oil with the temperature of 24 degrees and 91.2g of propylene glycol into a 5L polymerization reaction kettle, replacing 5 times with nitrogen, vacuumizing until the vacuum degree is-0.096 Mpa, pumping 5.1g of dimethylamine, heating to 100-130 ℃, reacting for 3 hours to prepare modified palm oil, and analyzing and detecting the hydroxyl value to be 126 mgKOH/g; 855g of sucrose and 151.8g of glycerol are added into a polymerization reaction kettle, nitrogen is replaced for 5 times, the vacuum degree is vacuumized to be-0.096 Mpa, 22.3 g of dimethylamine (40 percent) is added, the temperature is raised to 90 ℃, 700 g of propylene oxide is added, the reaction pressure is controlled to be 0.1-0.45Mpa during the period, the mixture is cured for 2 hours, the temperature is raised to 115 ℃ after the curing is finished, the vacuum dehydration is performed, 876.5g of modified palm oil is added, the mixture is mixed and stirred for 1-2 hours, 925g of residual propylene oxide is added, the reaction temperature is controlled to be 110-130 ℃, the pressure is controlled to be 0.1-0.45Mpa, and the curing is performed for 2-3 hours. And removing unreacted monomers in vacuum at the temperature of 120-140 ℃ for 1-3 h to obtain the hard foam polyether polyol product.
TABLE 1 comparison of polyether polyol indexes and Properties prepared in examples and comparative examples
| Example 1 | Example 2 | Comparative example 1 | Comparative example 2 | |
| Appearance of the product | Yellow transparent liquid | Yellow transparent liquid | Yellow translucent liquid with small amount of sugar particles | Dark yellow transparent liquid |
| Hydroxyl value (mgKOH/g) | 412 | 391 | 375 | 434 |
| Viscosity (25 ℃, mpa.s) | 8523 | 9410 | 11021 | 12308 |
| Water content (%) | 0.025 | 0.028 | 0.026 | 0.027 |
| Chroma (G.D.) | 6 | 7 | 8 | 10 |
| Compressive Strength (Kpa) | 650 | 635 | 552 | 571 |
| Dimensional stability | Is normal | Is normal | Shrinkage of | Shrinkage of |
As can be seen from the data in Table 1, the low-cost high-performance rigid foam polyether polyol prepared by the method has moderate viscosity, good appearance and uniform product phase. Because the product has uniform phase state and high functionality, the compressive strength and the toughness of the foamed product are improved, the bonding strength of the foamed product is improved, and the stability of the polyether foamed product is improved.
Finally, it is noted that: the above-mentioned list is only the preferred embodiment of the present invention, and naturally those skilled in the art can make modifications and variations to the present invention, which should be considered as the protection scope of the present invention provided they are within the scope of the claims of the present invention and their equivalents.
Claims (10)
1. A preparation method of hard foam polyether polyol is characterized by comprising the following steps:
s1, palm oil modification: adding palm oil and small molecular alcohol compounds into a reaction kettle, replacing nitrogen, and adding an amine catalyst to modify the palm oil;
s2, adding the composite high-functionality initiator and the modified palm oil into a reaction kettle, replacing with nitrogen, and carrying out primary curing reaction with a section of epoxy compound under the catalysis of a composite amine catalyst;
s3, after the curing is finished, dehydrating under a vacuum condition until the moisture is qualified;
s4, continuously adding a second-stage epoxy compound to perform a secondary curing reaction;
and S5, vacuumizing to remove unreacted monomers, and obtaining the hard foam polyether polyol product.
2. The method for preparing hard foam polyether polyol according to claim 1, wherein the small molecular alcohol compound in S1 is one or more of glycerol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, trimethylolpropane and pentaerythritol.
3. The method for preparing hard bubble polyether polyol according to claim 1, wherein the composite high functionality initiator in S2 is one or more of sucrose, sorbitol, xylitol, mannitol, glucose or maltose.
4. The method for preparing the hard foam polyether polyol according to claim 1, wherein the amine catalyst in S1 is one or two of dimethylamine, trimethylamine, diethylamine and triethylamine, and the composite amine catalyst in S2 is any two of dimethylamine, trimethylamine, diethylamine and triethylamine.
5. The method for preparing a rigid foam polyether polyol according to claim 1, wherein the primary epoxy compound and the secondary epoxy compound are the same epoxy compound agent, and the epoxy compound is one or two of ethylene oxide, propylene oxide or butylene oxide.
6. The preparation method of the hard foam polyether polyol according to claim 1, wherein the molar ratio of the palm oil to the small molecular alcohol compound is 1-5: 1, and the amine catalyst accounts for 0.1-0.3% of the total mass of the polyether.
7. The preparation method of the hard foam polyether polyol according to claim 1, wherein the molar ratio of the composite high-functionality initiator to the modified palm oil is 1-4: 1, and the composite amine catalyst accounts for 0.2-0.6% of the total mass of the polyether.
8. The method for preparing the hard foam polyether polyol according to claim 1, wherein the primary epoxy compound in S2 accounts for 10-25% of the total mass of the polyether; the second-stage epoxy compound in the S4 accounts for 30-50% of the total mass of the polyether, the curing time is 1-3 h, and the curing pressure is-0.4-0 Mpa.
9. The preparation method of the hard foam polyether polyol according to claim 1, wherein the temperature of S3 vacuum dehydration is 100-120 ℃, the dehydration time is 1-2.5 h, and the mass percentage of water after dehydration is 0.01-0.03%.
10. The preparation method of the hard foam polyether polyol as claimed in claim 1, wherein the reaction temperature for removing unreacted monomers in the S5 in vacuum is 120-140 ℃, and the removal time is 1-3 h.
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| 李兆星;李富亮;孙晓爱;: "硬泡用蔗糖型聚醚多元醇的合成研究", 聚氨酯工业, no. 01, pages 40 - 42 * |
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