CN111925515A - Renewable thermosetting polyether elastomer for propellant and preparation method thereof - Google Patents
Renewable thermosetting polyether elastomer for propellant and preparation method thereof Download PDFInfo
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- 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
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- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
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- 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
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- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
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Abstract
The invention discloses a renewable thermosetting polyether elastomer for a propellant and a preparation method thereof, and aims to solve the problems that a traditional isocyanate curing system is sensitive to water vapor, easily forms bubbles and is difficult to regenerate. The molecular structural formula of the related renewable thermosetting polyether elastomer for the propellant is as follows:
wherein x is 0, 1, y is 0, 1, n is 10-100, and is an integer. The preparation method comprises the following steps: firstly, ether polymer and furoyl chloride are used as raw materials to prepare furyl-modified ether polymer, then the furyl-modified ether polymer is used as prepolymer, tris (2-maleimide ethyl) amine is used as cross-linking agent, and Diels-Alder reaction is carried out to prepare the product used for propellantAnd regenerating the thermosetting polyether elastomer. The renewable thermosetting polyether elastomer for the propellant has the advantages of simple and easy synthetic route, insensitivity to water vapor in the curing process, regeneration function and wide application value in the field of solid propellants.
Description
Technical Field
The invention relates to a renewable thermosetting polyether elastomer for a propellant, which is suitable for the field of solid propellants.
Background
Nitrate ester plasticized polyether (NEPE) propellant is a composite solid propellant developed in the 80 th century, has the advantages of high energy level, excellent comprehensive performance and the like, and is applied to new-generation strategic missiles such as MX, tridentate II, dwarfism and the like in the United states. The adhesive for the NEPE propellant mainly comprises polyethylene glycol (PEG), ethylene oxide-tetrahydrofuran copolyether (PET), Polyethylene Glycol Adipate (PGA), polycaprolactone (PCP), segmented hydroxyl polybutadiene (HTPB) and the like. The polyether adhesive has the advantages of good low-temperature mechanical property, low viscosity, good processing technology and good performance adjustability, and becomes the key point of research on the formulation of the NEPE propellant. Similar to other cross-linked polymer materials, due to the irreversibility of the cross-linking reaction, the polyether adhesive is difficult to process again once being formed, and particularly, after the material is damaged, the polyether adhesive is difficult to recycle, so that great loss and resource waste are caused. Therefore, the development of the polyether adhesive with a renewable function can enable the polyether adhesive to be thermally repaired and recycled, and has very important industrial application value.
Jianan Xu et al (Jianan Xu, Zhiying Li, Bao Wang, Fengya Liu, Yudong Liu and Fengqi Liu. Recyclable biobased materials based on Diels-Alder cycloadadition. journal of Applied Polymer Science 2019,136(18):47352 47361) use epoxy-terminated polyethylene glycol to react with furfuryl amine to prepare a renewable polyethylene glycol-based prepolymer having a furan group in the side chain, and then use tris (2-maleimidoethyl) amine as a crosslinking agent to prepare a three-dimensional crosslinked polyether-based elastomer, and research results show that the three-dimensional crosslinked polyether-based elastomer has a utilization function. However, the polyethylene glycol-based prepolymer containing furan groups prepared by the method has high molecular weight and high viscosity, is not suitable for a solid propellant formulation system, and needs to be further improved.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the renewable thermosetting polyether elastomer for the propellant, which has the advantages of simple synthesis process, insensitivity to moisture in the curing process and renewable function, and the preparation method thereof.
In order to solve the technical problems, the invention adopts the following technical means:
a renewable thermosetting polyether elastomer for a propellant has a molecular structural formula as follows:
wherein x is 0, 1, y is 0, 1, n is 10-100, and is an integer.
Preferably, 15 ≦ n ≦ 80.
More preferably, 20 ≦ n ≦ 60.
Most preferably, 30 ≦ n ≦ 50.
The preparation method of the renewable thermosetting polyether elastomer for the propellant comprises the following steps:
(1) adding 1 part of ether polymer, 2-4 parts of furoyl chloride and 2-3 parts of triethylamine acid-binding agent into 40-80 parts of anhydrous tetrahydrofuran solvent to form a mixed solution, stirring and reacting at normal temperature for 12-36 hours under the protection of inert gas, and concentrating, washing and drying the reaction solution after the reaction time is up to obtain a product, namely the furan-terminated modified ether polymer;
(2) and (2) uniformly mixing 1 part of the synthesized furan-terminated modified ether polymer and 0.6-0.7 part of tris (2-maleimidoethyl) amine crosslinking agent in parts by mole, adding the mixture into a mold, placing the mold into an oven at 70-100 ℃, carrying out curing reaction for 8-36 h, and taking out a film in the mold after the reaction time is up to obtain the renewable thermosetting polyether elastomer for the propellant.
The ether polymer in the step (1) is polyethylene glycol, polytetrahydrofuran, ethylene oxide-tetrahydrofuran copolyether, and the molecular weight range is 500-11000 Da.
The invention has the advantages that:
the renewable thermosetting polyether elastomer for the propellant is prepared by taking the furan-terminated modified ether polymer as a prepolymer and the tris (2-maleimide ethyl) amine as a cross-linking agent through a Diels-Alder reaction, and the furan-terminated modified ether prepolymer as a raw material has the advantages of low molecular weight and low viscosity, and is suitable for a solid propellant formula system. Meanwhile, the renewable thermosetting polyether elastomer film for the propellant has good thermal reversible self-repairing performance.
Drawings
FIG. 1 is an electron micrograph of the self healing process of the renewable thermoset polyether elastomer used in the synthetic propellant of example 1.
Detailed Description
The present invention is further described below by way of examples, but the present invention is not limited thereto.
Testing an instrument:
the infrared spectrum is tested by an infrared spectrometer model Tensor 27 of Bruker company in Germany, and the test conditions are as follows: the scanning resolution is 4cm-1The number of scans was 20.
The electron microscope photograph is tested by using a hot stage polarizing microscope under the following test conditions: the hot stage temperature was 90 ℃.
The mold used in the production method of the present invention is a polytetrafluoroethylene-made mold having an inner groove, and is used for molding the sheet-like elastic body of the present invention without any particular requirement, and in the following examples, the size of the inner groove of the mold is 80 × 100 × 2mm or 80 × 100 × 10mm, but the present invention is not limited thereto.
The invention is further illustrated below with reference to examples and figures.
Example 1
This example provides a renewable thermoset polyether elastomer for propellants prepared as follows:
(1) sequentially adding polyethylene glycol (15g, 10mmol) with the molecular weight of 1500Da, 12mL of anhydrous tetrahydrofuran, furoyl chloride (2.88g, 22.02mmol) and acid-removing agent triethylamine (2.02g, 20mmol) into a 100mL three-mouth round-bottom bottle provided with a mechanical stirring device, a thermometer and a reflux device to form a mixed solution, and stirring and reacting the mixed solution at normal temperature for 30 hours under the protection of a nitrogen atmosphere; after the reaction time is up, concentrating and washing the reaction solution, and drying the reaction solution at 40 ℃ in vacuum to obtain furan-terminated modified polyethylene glycol;
(2) and (3) uniformly mixing 12g of the synthesized furan-terminated modified polyethylene glycol and a tris (2-maleimidoethyl) amine crosslinking agent (1.92g, 4.90mmol), adding the mixture into a polytetrafluoroethylene mold, placing the mold into an oven at 80 ℃, carrying out curing reaction for 24 hours, and demolding the mold after the reaction time is up to obtain a light yellow film.
And (3) structural identification:
infrared (KBr, cm)-1)：3303，2942，2860，1718，1602，1531，1444，1228，1101，998，882，818，762。
The above analytical data confirm that the material obtained according to this synthesis is indeed a renewable thermosetting polyether elastomer for propellants.
And (3) performance testing:
referring to fig. 1, it is a photo of the self-repairing process of the renewable thermosetting polyether elastomer for propellant provided in this example, which is tested by hot stage polarization microscope and the testing temperature is 90 ℃. Firstly, a scalpel is used for manufacturing scratches on the surface of the renewable thermosetting polyether elastomer film for the propellant provided by the embodiment, and then the scratch-free thermosetting polyether elastomer film is placed on a heating table with a constant temperature of 90 ℃; the repair experiments were performed under nitrogen atmosphere and photographs were taken at different times as shown in figure 1. It can be seen that after the renewable thermosetting polyether elastomer film for the propellant is placed on a hot table with a constant temperature of 90 ℃ for 16min, the scratches on the surface of the film are obviously changed, and the scratches are basically healed, which shows that the renewable thermosetting polyether elastomer film for the propellant has good thermal reversible self-repairing performance.
Example 2
This example provides a renewable thermoset polyether elastomer for propellants prepared as follows:
(1) sequentially adding polytetrahydrofuran (30g, 10mmol) with the molecular weight of 3000Da, 40mL of anhydrous tetrahydrofuran, furoyl chloride (6.0g, 38.32mmol) and a deacidifying agent triethylamine (3.56g, 35.16mmol) into a 250mL three-mouth round-bottom bottle provided with a mechanical stirring device, a thermometer and a reflux device to form a mixed solution, and stirring the mixed solution at normal temperature for reaction for 30 hours under the protection of a nitrogen atmosphere; after the reaction time is up, concentrating and washing the reaction solution, and drying the reaction solution in vacuum at 40 ℃ to obtain the polytetrahydrofuran modified by the terminal furan;
(2) and (3) uniformly mixing 24g of the synthesized furan-terminated modified polytetrahydrofuran and a tris (2-maleimidoethyl) amine crosslinking agent (2.0g, 5.18mmol), adding the mixture into a polytetrafluoroethylene mold, placing the mold into an oven at 80 ℃, carrying out curing reaction for 28h, and demolding the mold after the reaction time is up to obtain a light yellow film.
Example 3
This example provides a renewable thermoset polyether elastomer for propellants prepared as follows:
(1) sequentially adding ethylene oxide-tetrahydrofuran copolyether (45g, 10mmol) with the molecular weight of 4500Da, 65mL anhydrous tetrahydrofuran, furoyl chloride (5.84g, 44.8mmol) and deacidifying agent triethylamine (3.88g, 38.32mmol) into a 250mL three-mouth round-bottom bottle provided with a mechanical stirring device, a thermometer and a reflux device to form a mixed solution, and stirring the mixed solution at normal temperature for reaction for 20 hours under the protection of a nitrogen atmosphere; after the reaction time is up, concentrating and washing the reaction solution, and drying the reaction solution in vacuum at 40 ℃ to obtain furan-terminated modified ethylene oxide-tetrahydrofuran copolyether;
(2) and (3) uniformly mixing 36g of the synthesized furan-terminated modified ethylene oxide-tetrahydrofuran copolyether and a tris (2-maleimidoethyl) amine crosslinking agent (2.1g, 5.44mmol), adding the mixture into a polytetrafluoroethylene mold, placing the mold into an oven at 85 ℃, carrying out curing reaction for 12 hours, and demolding the mold after the reaction time is up to obtain a light yellow film.
Example 4
This example provides a renewable thermoset polyether elastomer for propellants prepared as follows:
(1) sequentially adding polytetrahydrofuran (30g, 10mmol) with the molecular weight of 3000Da, 40mL of anhydrous tetrahydrofuran, furoyl chloride (6.0g, 38.32mmol) and a deacidifying agent triethylamine (3.56g, 35.16mmol) into a 250mL three-mouth round-bottom bottle provided with a mechanical stirring device, a thermometer and a reflux device to form a mixed solution, and stirring the mixed solution at normal temperature for reaction for 12 hours under the protection of a nitrogen atmosphere; after the reaction time is up, concentrating and washing the reaction solution, and drying the reaction solution in vacuum at 40 ℃ to obtain the polytetrahydrofuran modified by the terminal furan;
(2) and (3) uniformly mixing 24g of the synthesized furan-terminated modified polytetrahydrofuran and a tris (2-maleimidoethyl) amine crosslinking agent (2.0g, 5.18mmol), adding the mixture into a polytetrafluoroethylene mold, placing the mold into an oven at 70 ℃, carrying out curing reaction for 36 hours, and demolding the mold after the reaction time is up to obtain a light yellow film.
Example 5
This example provides a renewable thermoset polyether elastomer for propellants prepared as follows:
(1) sequentially adding ethylene oxide-tetrahydrofuran copolyether (45g, 10mmol) with the molecular weight of 4500Da, 65mL anhydrous tetrahydrofuran, furoyl chloride (5.84g, 44.8mmol) and deacidifying agent triethylamine (3.88g, 38.32mmol) into a 250mL three-mouth round-bottom bottle provided with a mechanical stirring device, a thermometer and a reflux device to form a mixed solution, and stirring the mixed solution at normal temperature for 36 hours under the protection of a nitrogen atmosphere; after the reaction time is up, concentrating and washing the reaction solution, and drying the reaction solution in vacuum at 40 ℃ to obtain furan-terminated modified ethylene oxide-tetrahydrofuran copolyether;
(2) and (3) uniformly mixing 36g of the synthesized furan-terminated modified ethylene oxide-tetrahydrofuran copolyether and a tris (2-maleimidoethyl) amine crosslinking agent (2.1g, 5.44mmol), adding the mixture into a polytetrafluoroethylene mold, placing the mold into an oven at 100 ℃, carrying out curing reaction for 8 hours, and demolding the mold after the reaction time is up to obtain a light yellow film.
Claims (8)
1. A renewable thermosetting polyether elastomer for a propellant is characterized in that the molecular structural formula is as follows:
wherein x is 0, 1, y is 0, 1, n is 10-100, and is an integer.
2. The renewable thermosetting polyether elastomer for propellants according to claim 1, wherein 15 ≦ n ≦ 80.
3. The renewable thermosetting polyether elastomer for propellants according to claim 1, wherein 20 ≦ n ≦ 60.
4. The renewable thermosetting polyether elastomer for propellants according to claim 1, wherein 30 ≦ n ≦ 50.
5. The method for preparing the renewable thermosetting polyether elastomer for propellant as claimed in any one of claims 1 to 4, characterized by comprising the following steps:
(1) adding an ether polymer, furoyl chloride and a triethylamine acid-binding agent into an anhydrous tetrahydrofuran solvent to form a mixed solution, then reacting under the protection of inert gas, and concentrating, washing and drying the reaction solution after the reaction is finished to obtain a product, namely a furan-terminated modified ether polymer;
(2) and uniformly mixing the synthesized furan-terminated modified ether polymer and a tris (2-maleimidoethyl) amine crosslinking agent at 70-100 ℃ for curing reaction, and obtaining the renewable thermosetting polyether elastomer for the propellant after the reaction is finished.
6. The process for preparing a renewable thermosetting polyether elastomer for propellants according to claim 5, characterized by comprising the steps of:
(1) adding 1 part of ether polymer, 2-4 parts of furoyl chloride and 2-3 parts of triethylamine acid-binding agent into 40-80 parts of anhydrous tetrahydrofuran solvent to form a mixed solution, stirring and reacting at normal temperature for 12-36 hours under the protection of inert gas, and concentrating, washing and drying the reaction solution after the reaction time is up to obtain a product, namely the furan-terminated modified ether polymer;
(2) and (2) uniformly mixing 1 part of the synthesized furan-terminated modified ether polymer and 0.6-0.7 part of tris (2-maleimidoethyl) amine crosslinking agent in parts by mole, adding the mixture into a mold, placing the mold into an oven at 70-100 ℃, carrying out curing reaction for 8-36 h, and taking out a film in the mold after the reaction time is up to obtain the renewable thermosetting polyether elastomer for the propellant.
7. The process for preparing a renewable thermosetting polyether elastomer for propellants according to claim 6, characterized in that: the ether polymer in the step (1) is polyethylene glycol, polytetrahydrofuran, ethylene oxide-tetrahydrofuran copolyether, and the molecular weight range is 500-11000 Da.
8. A renewable thermosetting polyether elastomer for propellant synthesized by the method of any one of claims 1 to 7 is applied as a solid propellant adhesive.
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2020
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