CN116199855B - Polyether-polyester mixed polyurethane and preparation method thereof - Google Patents
Polyether-polyester mixed polyurethane and preparation method thereof Download PDFInfo
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
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Abstract
The invention belongs to the technical field of high polymer materials, and particularly relates to polyether-polyester mixed polyurethane and a preparation method thereof; the preparation method of the polyether-polyester mixed polyurethane with high performance and adjustable structure comprises the following steps: s1, generating a hydroxyl-terminated polyether-polyester copolymer prepolymer through ring opening reaction of epoxide and cyclic ester; s2, after purifying the prepolymer, adding polyether polyol, polyester polyol, polyisocyanate, chain extender and catalyst into the prepolymer, uniformly mixing the mixture, and heating the mixture for reaction; s3, extruding and granulating after the reaction is finished, so that the polyether-polyester mixed polyurethane elastomer with an adjustable structure has excellent mechanical properties, water resistance and oil resistance.
Description
Technical Field
The invention relates to the field of high polymer materials, in particular to polyether-polyester mixed polyurethane and a preparation method thereof.
Background
The polyurethane elastomer has excellent comprehensive properties such as high strength, high toughness, wear resistance, oil resistance and the like, has good processability, and is widely applied to various fields of national life such as cables, sealing elements, transmission belts, impact-resistant elements and the like. Along with the development of scientific technology, the application field of polyurethane elastomer is continuously expanded, and the actual application scene puts higher requirements on the performance of polyurethane elastomer. Due to the special structure of polyurethane, the mechanical properties of the polyurethane can be adjusted by adjusting the types and the dosage of the used soft segment, hard segment and chain extender. Soft segment materials of polyurethane tend to play a decisive role in their properties, common soft segment materials being polyether polyols and polyester polyols. The polyether polyurethane has good moisture permeability, hydrophilicity and elongation at break, and has good water resistance and low temperature resistance, but poor tensile strength. The polyester polyurethane has excellent mechanical property, film forming property, heat resistance, oil resistance and the like due to high cohesive force among ester groups.
The traditional polyurethane material adopts polyether polyol (or polyester polyol) and polyisocyanate to react into a prepolymer, and then the prepolymer is subjected to chain extension by using micromolecular dihydric alcohol and diamine to prepare an elastomer material, wherein the polyether elastomer has better low-temperature resistance and water resistance, low strength and low price; the polyester elastomer has poor low temperature resistance and water resistance, better single high temperature resistance, high mechanical strength and high price; the two elastomers have respective advantages, and the polyester polyol and the polyether polyol are easy to separate due to a large density difference of the synthetic process, so that the two elastomers cannot be mixed for use.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides polyether-polyester mixed polyurethane and a preparation method thereof.
The aim of the invention is realized by the following technical scheme: a polyether-polyester mixed polyurethane has the following structural formula:
which is a kind of
Wherein the polymerization degree m is 10-30, and the polymerization degree n is 5-20.
A preparation method of polyether-polyester mixed polyurethane comprises the following steps:
s1, performing ring-opening reaction on epoxide and cyclic ester to generate hydroxyl-terminated polyether-polyester copolymer prepolymer;
s2, purifying the prepolymer prepared in the step S1; adding polyether polyol, polyester polyol, polyisocyanate, chain extender and catalyst into the purified prepolymer, uniformly mixing, and heating for reaction;
and S3, extruding and granulating after the reaction is finished to obtain polyether-polyester mixed polyurethane.
Further, in the step S1, the polyether-polyester copolymer prepolymer is obtained by removing moisture after ring-opening reaction of epoxide and cyclic ester under the catalysis of Lewis acid and Lewis base.
Further, the lewis acid of the ring-opening reaction of the epoxide and the cyclic ester is triethylaluminum, and the lewis base is phosphazene base P4.
The structural formula of the polyether-polyester copolymer prepolymer is as follows:
further, the polyisocyanate is toluene diisocyanate or isophorone diisocyanate.
Further, the polyether polyol is polyethylene glycol or polypropylene glycol; the polyester polyol is polycaprolactone; the chain extender is diamine chain extender or alcohol chain extender; the catalyst is dibutyl tin laurate.
Further, the polyether-polyester copolymer prepolymer comprises, by mass, 15-30 parts of polyether polyol, 15-30 parts of polyester polyol, 45-90 parts of polyisocyanate, 3-5 parts of chain extender and 0.05-0.1 part of catalyst.
Further, the reaction time of the prepolymer in S1 is 1-4 hours, and the reaction time is adjusted according to the molecular weight of the polyether polyol and the polyester polyol in S2. I.e. a reaction time of 2000 molecular weight for 1 hour, 4000 molecular weight for 2 hours, 6000 molecular weight for 3 hours and 8000 molecular weight for 4 hours.
In S2, the heating temperature is 60-85 ℃ and the heating time is 1-4 hours.
The chemical structural formula of the specific preparation process of the polyurethane is as follows:
the beneficial effects of the invention are as follows:
(1) The polyether-polyester prepolymer has the advantages of simple synthesis, mild reaction condition, controllable structure and simple treatment, and can be directly used for preparing polyurethane.
(2) When the polyurethane is prepared, a part of polyether-polyester prepolymer is added, so that polyether polyol and polyester polyol are uniformly mixed in the reaction, and the compatibility in the reaction process is improved.
(3) The reaction condition for preparing the prepolymer is mild, the synthesized polyurethane has stable structure and good mechanical property, and meanwhile, the hydrolysis resistance and the oil resistance can be improved.
(4) The preparation method has the advantages of simple process, convenient operation and environmental protection, and the obtained polyurethane has obviously improved performance.
Drawings
Fig. 1 is an infrared spectrum of each of examples and comparative examples.
FIG. 2 shows the molecular weight and distribution of polyether-polyester prepolymer at different reaction times.
FIG. 3 shows nuclear magnetic resonance spectra of polyether-polyester prepolymer with different reaction times.
Detailed Description
The following describes the technical scheme of the present invention in detail, but the scope of the present invention is not limited to the following description.
Example 1
A preparation method of polyether-polyester mixed polyurethane comprises the following steps:
s1, adding 1 part of Lewis acid triethylaluminum into 100 parts of epoxypropane under the nitrogen atmosphere of 50 ℃ for reaction for 1 hour to obtain a polyether segment, then cooling to room temperature, adding 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 for reaction for 1 hour to generate
Polyether-polyester copolymer prepolymer;
s2, after the prepolymer is subjected to high-temperature water removal and purification, uniformly mixing 15 parts of polyether-polyester copolymer prepolymer, 15 parts of polypropylene glycol 2000, 15 parts of polycaprolactone 2000, 48 parts of isophorone diisocyanate, 3 parts of chain extender 1, 4-ethylene glycol and 0.1 part of catalyst dibutyl tin laurate, and heating to react at 85 ℃;
s3, extruding and granulating after the reaction is finished, so as to obtain the polyether-polyester mixed polyurethane elastomer with high performance and adjustable structure, wherein the temperature range of each section of the extruder is 160-220 ℃.
Example 2
A preparation method of polyether-polyester mixed polyurethane comprises the following steps:
s1, adding 1 part of Lewis acid triethylaluminum into 100 parts of propylene oxide under the nitrogen atmosphere of 50 ℃ to react for 2 hours to obtain a polyether segment, then cooling to room temperature, adding 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 to react for 2 hours to generate a polyether-polyester copolymer prepolymer;
s2, after the prepolymer is subjected to high-temperature water removal and purification, uniformly mixing 15 parts of polyether-polyester copolymer prepolymer, 20 parts of polypropylene glycol 2000, 20 parts of polycaprolactone 2000, 58 parts of isophorone diisocyanate, 3 parts of chain extender 1, 4-ethylene glycol and 0.1 part of catalyst dibutyl tin laurate, and then heating to react at 85 ℃;
and (3) extruding and granulating after the reaction of S3 is finished, so as to obtain the polyether-polyester mixed polyurethane elastomer with high performance and adjustable structure, wherein the temperature range of each section of the extruder is 160-220 ℃.
Example 3
100 parts of propylene oxide is added with 1 part of Lewis acid triethylaluminum under the nitrogen atmosphere of 50 ℃ to react for 1 hour to obtain polyether chain segments, then the polyether chain segments are cooled to room temperature, 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 are added to react for 1 hour to generate a polyether-polyester copolymer prepolymer, and the molecular weight and the nuclear magnetism of the polyether-polyester copolymer prepolymer are characterized after purification.
Example 4
100 parts of propylene oxide is added with 1 part of Lewis acid triethylaluminum under the nitrogen atmosphere of 50 ℃ to react for 2 hours to obtain polyether chain segments, then the polyether chain segments are cooled to room temperature, 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 are added to react for 2 hours to generate a polyether-polyester copolymer prepolymer, and the molecular weight and the nuclear magnetism of the polyether-polyester copolymer prepolymer are characterized after purification.
Example 5
100 parts of propylene oxide is added with 1 part of Lewis acid triethylaluminum under the nitrogen atmosphere of 50 ℃ to react for 3 hours to obtain a polyether segment, then the polyether segment is cooled to room temperature, 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 are added to react for 3 hours to generate a polyether-polyester copolymer prepolymer, and the molecular weight and the nuclear magnetism of the polyether segment are characterized after purification.
Example 6
100 parts of propylene oxide is added with 1 part of Lewis acid triethylaluminum under the nitrogen atmosphere of 50 ℃ to react for 4 hours to obtain a polyether segment, then the polyether segment is cooled to room temperature, 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 are added to react for 4 hours to generate a polyether-polyester copolymer prepolymer, and the molecular weight and the nuclear magnetism of the polyether segment are characterized after purification.
Example 7
100 parts of propylene oxide is added with 1 part of Lewis acid triethylaluminum under the nitrogen atmosphere of 50 ℃ to react for 1 hour to obtain a polyether segment, then the polyether segment is cooled to room temperature, 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 are added to react for 4 hours to generate a polyether-polyester copolymer prepolymer, and the molecular weight and the nuclear magnetism of the polyether segment are characterized after purification.
Example 8
100 parts of propylene oxide is added with 1 part of Lewis acid triethylaluminum under the nitrogen atmosphere of 50 ℃ to react for 4 hours to obtain a polyether segment, then the polyether segment is cooled to room temperature, 100 parts of caprolactone and 1 part of Lewis base phosphine cyanide base P4 are added to react for 1 hour to generate a polyether-polyester copolymer prepolymer, and the molecular weight and the nuclear magnetism of the prepolymer are characterized after purification.
Comparative example 1
A preparation method of polyether polyurethane elastomer comprises the following steps:
(1) Uniformly mixing 40 parts of polypropylene glycol 2000, 43 parts of isophorone diisocyanate, 3 parts of chain extender 1, 4-ethylene glycol and 0.1 part of catalyst dibutyl tin laurate, and then heating to react at 85 ℃;
(2) And after the reaction is finished, extruding and granulating the mixture to obtain the polyether polyurethane elastomer, wherein the temperature of each section of the extruder is Fan Wei-220 ℃.
Comparative example 2
A preparation method of a polyester polyurethane elastomer comprises the following steps:
(1) Uniformly mixing 40 parts of polycaprolactone 2000, 43 parts of isophorone diisocyanate, 3 parts of chain extender 1, 4-ethylene glycol and 0.1 part of catalyst dibutyl tin laurate, and then heating to react at 85 ℃;
(2) And after the reaction is finished, extruding and granulating the mixture to obtain the polyester polyurethane elastomer, wherein the temperature range of each section of the extruder is 160-220 ℃.
Comparative example 3
A preparation method of a polyether-polyester mixed polyurethane elastomer comprises the following steps:
(1) Uniformly mixing 20 parts of polyethylene glycol 2000, 43 parts of isophorone diisocyanate and 0.1 part of catalyst dibutyl tin laurate, and then heating to react at 85 ℃;
(2) After the reaction of the step (1), adding 20 parts of polycaprolactone 2000 and 3 parts of chain extender 1, 4-glycol to continue the reaction;
(3) And after the reaction is finished, extruding and granulating the mixture to obtain the polyether-polyester mixed polyurethane elastomer, wherein the temperature range of each section of the extruder is 160-220 ℃.
The characterization of the infrared structure was performed on the polyurethanes obtained in examples 1,2 and comparative examples above, and the results are shown in fig. 1. As can be seen from the figure, at 3330cm -1 Is the stretching vibration peak of N-H in the urethane structure, and the position of the stretching vibration peak moves to a low wave number along with the increase of polyether content in the polyurethane chain segment. Polyurethane of 2921cm -1 And 2853cm -1 Where are respectively corresponding to CH 2 Symmetrical and asymmetrical absorption peaks, the symmetrical peak of the polyether urethane of comparative example 1 is significantly stronger than the asymmetrical peak, the symmetrical peak of the polyester urethane of comparative example 2 is significantly weaker than the asymmetrical peak, and the intensities of the two peaks are equivalent when polyether-polyester segments are simultaneously present in the urethane segments. It follows that polyurethane is successfully synthesized and that the polyether and polyester content in the segments has a certain influence on their structure.
The polyether-polyester prepolymer obtained in examples 3 to 8 was subjected to molecular weight characterization, and the results are shown in FIG. 2. As can be seen from the graph, the molecular weight of the polyether-polyester prepolymer in examples 3 to 6 increases with the increase of the reaction time. In examples 7 and 8, the total time of the front and rear reactions was equal, and the molecular weights of the obtained prepolymers were substantially the same. Thus, in the subsequent synthesis of the polyurethane, the reaction time of the first step may be adjusted according to the molecular weights of the polyether polyol and the polyester polyol in the reactants.
The polyether-polyester prepolymer obtained in examples 3 to 8 was subjected to nuclear magnetic resonance hydrogen spectrum characterization, and the results are shown in FIG. 3. From the graph, the peak areas of the methyl groups and the methylene groups in the nuclear magnetic resonance hydrogen spectrogram gradually increase along with the increase of the reaction time of the prepolymer in examples 3 to 6. In examples 7 and 8, the peak areas of the methyl groups having a long period of time for the ring-opening reaction of propylene oxide were relatively large, and the peak areas of the methylene groups having a long period of time for the ring-opening reaction of caprolactone were large, due to the difference in the periods of time for the ring-opening reaction of the two monomers. It can be stated that the stage of preparation of the prepolymer can be controlled by controlling the reaction time to obtain a prepolymer of a predetermined molecular weight and a different polyether-polyester block structure.
The polyurethane elastomers obtained in examples 1 and 2 and comparative example were subjected to tests for mechanical properties, water resistance, oil resistance and durability, the water resistance test method being to test changes in tensile strength and elongation at break after being left in water at 80℃for 168 hours, the oil resistance test method being to test tensile strength and elongation at break after being left in oil at 100℃for 168 hours, and the performance data being shown in Table 1:
as can be seen from the table, the mechanical properties of the polyether polyurethane are obviously weaker than those of the polyester polyurethane, and the mechanical properties between the two chain segments can be obtained by a certain synthesis means to enable the two chain segments to exist in the polyurethane main chain at the same time. Since polyether polyurethane has hydrolysis resistance and polyester polyurethane has oil resistance, the polyether polyester mixed polyurethane obtained has excellent characteristics of both. Examples 1 and 2 each have excellent water and oil repellency, whereas polyether-based polyurethane and polyester-based polyurethane alone have only one of them and are inferior in durability to polyether-polyester mixed polyurethane.
The foregoing is merely a preferred embodiment of the invention, and it is to be understood that the invention is not limited to the form disclosed herein but is not to be construed as excluding other embodiments, but is capable of numerous other combinations, modifications and environments and is capable of modifications within the scope of the inventive concept, either as taught or as a matter of routine skill or knowledge in the relevant art. And that modifications and variations which do not depart from the spirit and scope of the invention are intended to be within the scope of the appended claims.
Claims (7)
1. The preparation method of the polyether-polyester mixed polyurethane elastomer is characterized by comprising the following steps of:
s1, generating hydroxyl-terminated polyether-polyester copolymer prepolymer by ring-opening reaction of propylene oxide and caprolactone;
s2, purifying the prepolymer prepared in the step S1; adding polypropylene glycol, polycaprolactone, isophorone diisocyanate, a chain extender and a catalyst into the purified prepolymer, uniformly mixing, and heating for reaction;
and S3, extruding and granulating after the reaction is finished to obtain the polyether-polyester mixed polyurethane elastomer.
2. The method for preparing a polyether-polyester mixed polyurethane elastomer according to claim 1, wherein in the step S1, the polyether-polyester copolymer prepolymer is obtained by removing moisture after ring-opening reaction of propylene oxide and caprolactone under the catalysis of Lewis acid and Lewis base.
3. The method for preparing a polyether-polyester mixed polyurethane elastomer according to claim 1, wherein the Lewis acid for the ring opening reaction of propylene oxide and caprolactone is triethylaluminum, and the Lewis base is phosphazene ligand P4-t-Bu.
4. The method for preparing a polyether-polyester mixed polyurethane elastomer according to claim 1, wherein the reaction time of the ring-opening reaction of propylene oxide and caprolactone is 1 hour, and the molecular weight of polypropylene glycol and polycaprolactone in the subsequent polyurethane synthesis step is 2000; the reaction time of the ring-opening reaction of propylene oxide and caprolactone is 2 hours, and the molecular weight of polypropylene glycol and polycaprolactone in the subsequent polyurethane synthesis step is 4000; the reaction time of the ring-opening reaction of propylene oxide and caprolactone is 3 hours, and the molecular weight of polypropylene glycol and polycaprolactone in the subsequent polyurethane synthesis step is 6000; the reaction time of the ring-opening reaction of propylene oxide and caprolactone was 4 hours, and the molecular weight of polypropylene glycol and polycaprolactone in the subsequent polyurethane synthesis step was 8000.
5. The preparation method of the polyether-polyester mixed polyurethane elastomer is characterized by comprising, by mass, 15-30 parts of polyether-polyester copolymer prepolymer, 15-30 parts of polypropylene glycol, 15-30 parts of polycaprolactone, 45-90 parts of isophorone diisocyanate, 3-5 parts of chain extender and 0.05-0.1 part of catalyst.
6. The method for preparing the polyether-polyester mixed polyurethane elastomer according to claim 1, wherein the reaction time of the prepolymer in S1 is 1-4 hours.
7. The method for preparing the polyether-polyester mixed polyurethane elastomer according to claim 1, wherein in the step S2, the heating temperature is 60-85 ℃ and the time is 1-4 hours.
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| CN113845873B (en) * | 2021-09-29 | 2022-09-09 | 韦尔通(厦门)科技股份有限公司 | Bio-polyether ester reaction type polyurethane hot melt adhesive and preparation method thereof |
| CN114106280B (en) * | 2021-12-14 | 2023-05-16 | 上海华峰新材料研发科技有限公司 | Aliphatic polyurethane resin and preparation method and application thereof |
| CN115232285B (en) * | 2022-08-17 | 2023-12-29 | 江苏华大新材料有限公司 | Solvent-free polyurethane resin for synthetic leather and preparation method thereof |
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