CN114230784B - Preparation method and application of polyether polyol - Google Patents
Preparation method and application of polyether polyol Download PDFInfo
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- 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
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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Abstract
The invention discloses an H- (O-R-) n The polyether polyol with the structural general formula shown in the formula (1) is prepared by introducing dihydric alcohol, carrying out pressurization etherification reaction, depressurization dehydration, pressurization etherification reaction, catalyst removal treatment and refining under the action of phosphate catalysts with specific structures, has the characteristic of narrow molecular weight distribution, is used for polyurethane elastomers, adhesives, coatings and foaming materials, and is beneficial to reducing the operation cost and expanding the terminal application field.
Description
Technical Field
The invention belongs to the technical field of polyether polyol, and particularly relates to polyether polyol with a novel synthetic route, a preparation method and application thereof.
Background
Polyether polyol is a product with excellent comprehensive performance, is an important raw material for synthesizing polyurethane materials, and is widely applied to the fields of polyurethane foam, elastomer, adhesives, coatings and the like.
The polyether polyol is usually prepared by initiating ring-opening polymerization of monomers such as ethylene oxide, propylene oxide and the like by taking polyol as an initiator. The polyether polyol is limited in monomer types, has a single structure, and is difficult to completely meet the requirements on performance in partial high-end application occasions.
To break this limitation, many workers have focused on developing new monomers and new synthetic methods. In a plurality of synthetic routes, the process of dehydrating dihydric alcohol into ether is utilized, the raw materials are rich in variety and low in cost and are easy to obtain, and the method is particularly suitable for synthesizing polyether polyol with a special structure.
However, in the process of dehydration of dihydric alcohol, the reaction product often has a relatively wide molecular weight distribution, and when the corresponding polyether polyol is applied to the fields of elastomers, soft foam, hard foam and the like, the application requirement is relatively difficult to meet.
Therefore, the need to develop a process for synthesizing polyether polyols using diols with a narrow molecular weight distribution is urgent.
Disclosure of Invention
In view of the above problems in the prior art, it is an object of the present invention to provide a process for synthesizing polyether polyols using diols having a narrow molecular weight distribution.
In order to achieve the above object, the present invention adopts the following technical scheme:
a polyether polyol is prepared from a diol monomer with a structural formula of HO-R-OH, and has the following structure (formula I):
H-(O-R-) n -OH (formula I)
Wherein R is C 2 -C 10 A linear alkyl group of (a); the dihydric alcohol HO-R-OH is at least one selected from 1, 10-decanediol, 1, 9-nonanediol, 1, 8-octanediol, 1, 7-heptanediol, 1, 6-hexanediol, 1, 5-pentanediol, 1, 4-butanediol or 1, 3-propanediol; preferably, the dihydric alcohol is at least any one of 1, 5-pentanediol and 1, 4-butanediol.
In a specific embodiment, the polyether polyol of the structure of formula (I) has a molecular weight of 500-2000.
In another aspect of the present invention, there is provided a process for preparing the polyether polyol described above, comprising the steps of:
1) Vacuum etherification reaction: dehydrating the dihydric alcohol reactant A and the catalyst B at a certain reaction temperature under vacuum to carry out etherification reaction, and removing small molecular byproduct water;
2) Pressurized etherification reaction: adding a cocatalyst C into the product of the step 1), and further carrying out etherification reaction at high temperature and normal pressure;
3) Catalyst removal treatment: adding diatomite adsorption catalyst and cocatalyst into the product of the step 2), filtering at a certain temperature, and collecting filtrate to obtain a crude product polyether polyol;
4) Refining: and (3) removing water and other byproducts from the product of the step (3) at a certain temperature under high vacuum to obtain the polyether polyol with the structure shown in the formula (1).
In a specific embodiment, in said step 1), said reactant a is selected from at least any one of 1, 10-decanediol, 1, 9-nonanediol, 1, 8-octanediol, 1, 7-heptanediol, 1, 6-hexanediol, 1, 5-pentanediol, 1, 4-butanediol, or 1, 3-propanediol; preferably, the dihydric alcohol is at least any one of 1, 5-pentanediol and 1, 4-butanediol;
the catalyst B is selected from phosphate esters and has the following structure (formula II):
the catalyst B can be obtained by esterification or transesterification reaction of phosphoric acid or phosphoric acid ester and dihydric alcohols with structural formulas of HO-R1-OH, HO-R2-OH and HO-R3-OH. Wherein, the dihydric alcohol HO-R1-OH has a structure consistent with the reactant A, and the general formula is HO- (CH 2) n-OH; the general formulas of the dihydric alcohol HO-R2-OH and the HO-R3-OH are HO- (CH 2) n1-OH, HO- (CH 2) n2-OH and n1 is more than or equal to n and less than or equal to n2 respectively. It was found through extensive experimentation that when 0<n-n1.ltoreq.2 and 0< n 2-n.ltoreq.2, the product has a narrow molecular weight distribution, more preferably n1=n2-n=1.
Catalyst B is preferably used in an amount of 0.1 to 5% by mass of reactant A.
In a specific embodiment, in said step 1), the reaction temperature is 80-120 ℃, preferably 95-105 ℃; the reaction pressure is 0.1 to 10kPa; the reaction time is 20-50h.
In a specific embodiment, in said step 2), the cocatalyst C is selected from titanates, preferably isopropyl titanate and n-butyl titanate. The amount of cocatalyst C used is 15 to 100ppm, preferably 30 to 50ppm, of reactant A.
In a specific embodiment, in said step 2), the product obtained in said step 1) is heated to 140-170 ℃, preferably 150-160 ℃, under normal pressure, and further reacted with the addition of the cocatalyst C for 8-20 hours, preferably 12-16 hours.
In a specific embodiment, in the step 3), the product obtained in the step 2) is cooled to 80-120 ℃; adding diatomite with the mass of 1-5% of the reactant A into the product, mixing for 2-4 hours, filtering while the reactant A is hot under the condition of heat preservation, and collecting filtrate to obtain the crude product polyether polyol.
In a specific embodiment, in said step 4), the product obtained in said step 3) is heated to 160-180 ℃, preferably 170 ℃; the pressure is 1-10kPa; the refining time is 1-3h.
In a further aspect the invention relates to the use of the polyether polyols described above or prepared by the process described above in polyurethane elastomers, adhesives, coatings or foams.
Compared with the prior art, the technical scheme of the invention has the following beneficial effects:
1) The polyether polyol prepared by using the catalyst with a specific structure under a certain process has the characteristic of narrow molecular weight distribution, and the molecular weight distribution PDI is generally in the range of 1.05-1.2.
2) The polyether polyol obtained by the invention has low operation cost in the process of synthesizing polyurethane, has good compatibility with polyester polyol, polyether polyol, various organic solvents and assistants participating in polyurethane synthesis, and can be widely applied to the fields of polyurethane elastomers, adhesives, coatings, foaming materials and the like.
Detailed Description
So that the technical features and content of the present invention can be understood in detail, preferred embodiments of the present invention will be described in more detail below. While the preferred embodiments of the present invention have been described in the examples, it should be understood that the present invention may be embodied in various forms and should not be limited to the embodiments set forth herein.
The analysis and detection method comprises the following steps:
nuclear magnetic instrument model: bruk AVANCE III M nuclear magnetic resonance spectrometer;
the viscosity test method comprises the following steps: test with reference to standard GB/T22235-2008;
the alkenyl end ratio test method comprises the following steps: by 1H-NMR, calculating the peak area S1 representing the double bond at a chemical shift of 5.0ppm and the peak area S2 representing the terminal hydroxyl group at a chemical shift of 3.6ppm, the terminal alkenyl ratio=s1/(s1+s2) ×100%;
polyether polyol hydroxyl number: reference standard GB/T12008.3-2009 test.
Molecular weight distribution: obtained by direct measurement by GPC.
Example 1
1) Vacuum etherification reaction:
1380g of 1, 5-pentanediol and 14g of a catalyst having the following structure were reacted at 95℃under 2kPa for 28 hours while removing by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 150 ℃ under normal pressure, and 0.07g of isopropyl titanate is added for further reaction for 16 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 90 ℃; 38.6g of diatomaceous earth was added to the product and mixed for 3 hours, filtered while hot under heat preservation, and the filtrate was collected to obtain a crude polyether polyol.
4) Refining:
the product obtained in step 3) is heated to 170 ℃ and refined for 1h under 5 kPa.
1132.5g of the product polyether polyol was obtained in a yield of 99.4%. The hydroxyl value of the product was 56.8mgKOH/g and the viscosity at 25℃was 3685cP. The double bond content in the product was 0.1mol% and the proportion of cyclic small molecules was 0.22wt%. The molecular weight distribution PDI was 1.07.
Example 2
1) Vacuum etherification reaction:
1354g of 1, 4-butanediol and 2.7g of the catalyst having the following structure were reacted at 105℃under 6kPa for 37 hours while removing by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 160 ℃ under normal pressure, and 0.05g of isopropyl titanate is added for further reaction for 12 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 110 ℃; 15g of kieselguhr is added into the product, mixed for 4 hours, filtered while the product is hot under heat preservation, and the filtrate is collected to obtain the crude polyether polyol.
4) Refining:
the product obtained in step 3) was heated to 175℃and refined for 2h at 8 kPa.
1078.9g of the product polyether polyol was obtained in a yield of 99.6%. The hydroxyl value of the product was 117.5mgKOH/g and the viscosity at 25℃was 1098cP. The double bond content in the product was 0.1mol% and the proportion of cyclic small molecules was 0.24wt%. The molecular weight distribution PDI was 1.08.
Example 3
1) Vacuum etherification reaction:
1385g of 1, 9-nonanediol and 24.9g of a catalyst of the following structure were reacted at 85℃and 0.2kPa for 21 hours, with removal of by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 140 ℃ under normal pressure, and 0.05g of isopropyl titanate is added for further reaction for 20 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 80 ℃; 16.6g of diatomaceous earth was added to the product and mixed for 4 hours, filtered while hot under heat preservation, and the filtrate was collected to obtain a crude polyether polyol.
4) Refining:
the product obtained in step 3) is heated to 160 ℃ and refined for 1h under 1 kPa.
1217.0g of the product polyether polyol was obtained in a yield of 98.7%. The product has a hydroxyl value of 158.2mgKOH/g and a viscosity at 25℃of 725cP. The double bond content in the product was 0.2mol% and the proportion of cyclic small molecules was 0.23wt%. The molecular weight distribution PDI was 1.09.
Example 4
1) Vacuum etherification reaction:
1395.7g of 1, 6-hexanediol and 58.6g of a catalyst of the structure below were reacted at 115℃for 30h under 8kPa, with removal of by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 170 ℃ under normal pressure, and 0.13g of isopropyl titanate is added for further reaction for 8 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 120 ℃; 55.8g of diatomaceous earth was added to the product and mixed for 2 hours, filtered while hot under heat preservation, and the filtrate was collected to obtain a crude polyether polyol.
4) Refining:
the product obtained in step 3) is heated to 170 ℃ and refined for 3 hours under 10 kPa.
1156.2g of the product polyether polyol was obtained in a yield of 97.2%. The hydroxyl value of the product was 217.6mgKOH/g and the viscosity at 25℃was 356cP. The double bond content in the product was 0.7mol% and the proportion of cyclic small molecules was 0.45wt%. The molecular weight distribution PDI was 1.15.
Comparative example 1
1) Vacuum etherification reaction:
1380g of 1, 5-pentanediol and 14g of a catalyst having the following structure were reacted at 95℃under 2kPa for 28 hours while removing by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 150 ℃ under normal pressure, and 0.07g of isopropyl titanate is added for further reaction for 16 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 90 ℃; 38.6g of diatomaceous earth was added to the product and mixed for 3 hours, filtered while hot under heat preservation, and the filtrate was collected to obtain a crude polyether polyol.
4) Refining:
the product obtained in step 3) is heated to 170 ℃ and refined for 1h under 5 kPa.
1009.5g of the product polyether polyol was obtained in a yield of 88.6%. The hydroxyl value of the product was 76.8mgKOH/g and the viscosity at 25℃was 3458cP. The double bond content in the product was 1.8mol% and the proportion of cyclic small molecules was 2.13wt%. The molecular weight distribution PDI was 1.75.
Comparative example 2
1) Vacuum etherification reaction:
1354g of 1, 4-butanediol and 2.7g of the catalyst having the following structure were reacted at 105℃under 6kPa for 37 hours while removing by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 160 ℃ under normal pressure, and 0.05g of isopropyl titanate is added for further reaction for 12 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 110 ℃; adding 15 diatomite into the product, mixing for 4 hours, filtering while the mixture is hot under heat preservation, and collecting filtrate to obtain the crude polyether polyol.
4) Refining:
the product obtained in step 3) was heated to 175℃and refined for 2h at 8 kPa.
934.8g of the product polyether polyol was obtained in a yield of 86.3%. The hydroxyl value of the product was 141.3mgKOH/g and the viscosity at 25℃was 1002cP. The double bond content in the product was 2.2mol% and the proportion of cyclic small molecules was 2.52wt%. The molecular weight distribution PDI was 1.83.
Comparative example 3
1) Vacuum etherification reaction:
1395.7g of 1, 6-hexanediol, 58.6g of phosphoric acid were reacted as catalyst at 115℃under 8kPa for 30 hours, with the removal of by-product water.
2) Pressurized etherification reaction:
the product obtained in the step 1) is heated to 170 ℃ under normal pressure, and 0.13g of isopropyl titanate is added for further reaction for 8 hours.
3) Catalyst removal treatment:
cooling the product obtained in the step 2) to 120 ℃; 55.8g of diatomaceous earth was added to the product and mixed for 2 hours, filtered while hot under heat preservation, and the filtrate was collected to obtain a crude polyether polyol.
4) Refining:
the product obtained in step 3) is heated to 170 ℃ and refined for 3 hours under 10 kPa.
870.7g of the product polyether polyol was obtained in a yield of 73.2%. The product has a hydroxyl value of 275.6mgKOH/g and a viscosity at 25℃of 323cP. The double bond content in the product was 4.95mol% and the proportion of cyclic small molecules was 5.86wt%. The molecular weight distribution PDI was 2.35.
While the present invention has been described in detail through the foregoing description of the preferred embodiment, it should be understood that the foregoing description is not to be considered as limiting the invention. Those skilled in the art will appreciate that certain modifications and adaptations of the invention are possible and can be made under the teaching of the present specification. Such modifications and adaptations are intended to be within the scope of the present invention as defined in the appended claims.
Claims (11)
1. A process for preparing a polyether polyol comprising the steps of:
1) Vacuum etherification reaction: dehydrating the dihydric alcohol reactant A and the catalyst B at a certain reaction temperature under vacuum to carry out etherification reaction, and removing small molecular byproduct water; the reactant A is at least one of 1, 10-decanediol, 1, 9-nonanediol, 1, 8-octanediol, 1, 7-heptanediol, 1, 6-hexanediol, 1, 5-pentanediol, 1, 4-butanediol or 1, 3-propanediol; the catalyst B is selected from phosphate esters and has the following structure:
catalyst B is prepared from phosphoric acid or phosphate ester and has a structural formula of HO-R 1 -OH、HO-R 2 -OH and HO-R 3 Esterification or transesterification of dihydric alcohol of-OH; wherein the method comprises the steps ofDihydric alcohol HO-R 1 the-OH has a structure consistent with that of the reactant A and has a general formula of HO- (CH) 2 ) n-OH, dihydric alcohol HO-R 2 -OH and HO-R 3 The general formula of the-OH is HO- (CH) 2 )n1-OH、HO-(CH 2 ) n2-OH, and satisfies 0<n-n1≤2、0<n2-n≤2；
2) Pressurized etherification reaction: adding a cocatalyst C into the product of the step 1), and further carrying out etherification reaction at high temperature and normal pressure; the high temperature is 140-170 ℃;
3) Catalyst removal treatment: adding an adsorbent to adsorb a catalyst and a cocatalyst into the product of the step 2), filtering at a certain temperature, and collecting filtrate to obtain a crude product polyether polyol.
2. The method for producing polyether polyol according to claim 1, wherein n-n1=n2-n=1.
3. The process for preparing polyether polyols according to claim 1, wherein catalyst B is used in an amount of from 0.1 to 5% by mass of reactant A.
4. A process for the preparation of polyether polyols according to any one of claims 1 to 3, wherein in step 1) the reaction temperature is 80 to 120 ℃; the reaction pressure is 0.1 to 10kPa; the reaction time is 20-50h.
5. The method for preparing polyether polyol according to claim 1, wherein in the step 2), the cocatalyst C is selected from titanate esters.
6. The process for preparing polyether polyols according to claim 5, wherein the cocatalyst C is selected from isopropyl titanate and/or n-butyl titanate.
7. The process for preparing polyether polyols according to claim 5, wherein the cocatalyst C is used in an amount of from 15 to 100ppm of the reactant A.
8. The method for producing polyether polyol according to any one of claims 1 and 5 to 7, wherein the reaction time in step 2) is 8 to 20 hours.
9. The method for preparing polyether polyol according to claim 1, wherein in the step 3), the temperature is 80 to 120 ℃;
the adsorbent is diatomite, and the dosage is 1-5% of the mass of the reactant A.
10. The process for preparing a polyether polyol according to claim 1 or 9, further comprising step 4): and 3) removing water and other byproducts from the product of the step 3) at a certain temperature under high vacuum, and refining to obtain the polyether polyol.
11. The method for preparing polyether polyol according to claim 10, wherein in the step 4), the temperature is 160 to 180 ℃; the pressure is 1-10kPa; the time is 1-3h.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1774462A (en) * | 2002-11-22 | 2006-05-17 | 三菱化学株式会社 | Method for producing polyether polyol |
| CN109293912A (en) * | 2018-09-21 | 2019-02-01 | 万华化学集团股份有限公司 | A kind of polyethers and its preparation method and application of controllable silicone content |
| 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 |
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| US20060223979A1 (en) * | 2005-04-04 | 2006-10-05 | Thomas Ostrowski | Process for preparing polyether polyols |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1774462A (en) * | 2002-11-22 | 2006-05-17 | 三菱化学株式会社 | Method for producing polyether polyol |
| CN109293912A (en) * | 2018-09-21 | 2019-02-01 | 万华化学集团股份有限公司 | A kind of polyethers and its preparation method and application of controllable silicone content |
| 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 |
Non-Patent Citations (1)
| Title |
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| 聚醚多元醇的合成研究进展;于剑昆;赵巍;庄远;;化学推进剂与高分子材料;第15卷(第03期);第19-37页 * |
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