CN116903873A - Self-repairing tung oil-based shape memory polymer and preparation method thereof - Google Patents
Self-repairing tung oil-based shape memory polymer and preparation method thereof Download PDFInfo
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- CN116903873A CN116903873A CN202310873334.9A CN202310873334A CN116903873A CN 116903873 A CN116903873 A CN 116903873A CN 202310873334 A CN202310873334 A CN 202310873334A CN 116903873 A CN116903873 A CN 116903873A
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- 239000002383 tung oil Substances 0.000 title claims abstract description 37
- 229920000431 shape-memory polymer Polymers 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000013067 intermediate product Substances 0.000 claims abstract description 57
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003822 epoxy resin Substances 0.000 claims abstract description 13
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 19
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 18
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 9
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 22
- 125000004185 ester group Chemical group 0.000 abstract description 4
- 230000007334 memory performance Effects 0.000 abstract description 3
- 238000005698 Diels-Alder reaction Methods 0.000 abstract description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000006386 memory function Effects 0.000 abstract 1
- 229920003192 poly(bis maleimide) Polymers 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 239000002861 polymer material Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 4
- 150000008064 anhydrides Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000012815 thermoplastic material Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000012781 shape memory material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical group 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920013724 bio-based polymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Abstract
The self-repairing tung oil-based shape memory polymer and a preparation method thereof are provided, wherein in the first step, a certain proportion of maleic anhydride reacts with tung oil to obtain an intermediate product A; secondly, reacting the prepared intermediate product A with furfuryl alcohol to obtain an intermediate product B; and thirdly, adding bismaleimide with a certain proportion, adding epoxy resin and an ionic catalyst with different proportions, and curing in an oven at 120 ℃ to obtain the self-repairing tung oil-based shape memory polymer. Diels-Alder dynamic bond and ester exchange dynamic bond in the self-repairing tung oil-based shape memory polymer prepared by the method can endow the prepared polymer with excellent self-repairing capability and shape memory performance, the polymer is prepared by adopting a biological base material, the process is simple and convenient, the mechanical performance is controllable, the self-repairing and shape memory functions can be realized under the heating condition, and the shape memory performance and the mechanical performance loss after repeated use are small.
Description
Technical Field
The invention belongs to the field of bio-based intelligent polymer materials, and particularly relates to a self-repairable tung oil-based shape memory polymer and a preparation method thereof.
Background
Shape memory materials refer to materials that are deformed and fixed to another shape and then restored to the original shape by physical or chemical stimulation such as heat, light, electricity, etc. Shape memory materials are widely used in various fields of industry and daily life, such as smart textiles, flexible electronics, 3D or 4D printing, smart medical devices, and the like. However, most of the raw materials for synthesizing the shape memory polymer are converted from petrochemical resources, and with the increasing increase of carbon emission and continuous consumption of petroleum resources, the use of biomass resources instead of non-sustainable resources is becoming the mainstream of the development of the era.
The conventional synthetic polymer materials can be classified into thermoplastic and thermosetting materials, and when the thermoplastic materials are heated to a certain temperature, intermolecular forces are destroyed to generate fluidity, so that the thermoplastic materials have repeated processability. While most common shape memory polymer materials are thermoset, thermoset materials are limited by cross-linked networks, traditional thermoset materials do not have reproducible processability and once cured, the material is neither melted nor dissolved. Thermoset materials generally have better stability than thermoplastic materials, but recycling of thermoset materials has been a major challenge in the polymer arts. Conventional landfills and incineration not only do not make efficient use of the remaining value of the material, but also place a burden on the environment. With the increasing awareness of human being on environmental protection, studies on recycling of thermosetting materials are paid attention to. The best method for solving the problem is to develop a novel thermosetting material, so that the material has the characteristics of easy processing, repair and degradation.
On the other hand, the bio-based material has the characteristics of green, environment-friendly, renewable raw materials and biodegradability which are not possessed by the traditional high polymer material, in particular tung oil, furfuryl alcohol, dimer acid epoxy and the like, and the raw materials are easy to obtain, renewable, low in toxicity and high in universality, so that the bio-based material becomes a hot spot for researching bio-based polymers. The invention prepares the intelligent functional polymer material by adopting the biological-based resource. Has certain theoretical guidance and application significance for promoting the progress of the application technology of the vegetable oil-based intelligent polymer.
Disclosure of Invention
The technical problems to be solved are as follows: the invention provides a self-repairing tung oil-based shape memory polymer and a preparation method thereof, wherein the shape memory polymer which fuses dynamic Diels-Alder bonds and dynamic transesterification is prepared by taking tung oil as a raw material.
The technical scheme is as follows: the preparation method of the self-repairing tung oil-based shape memory polymer comprises the following steps: adding tung oil and maleic anhydride into a reaction vessel according to the mol ratio of (2.5-2.9), adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to a molar ratio of 1:3, adding hexadecyl trimethyl ammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: mixing an intermediate product B with 4,4 '-bismaleimide diphenylmethane, epoxy resin and zinc acetylacetonate accounting for 1.5% of the total mass of the system, wherein the molar ratio of the intermediate product B to the 4,4' -bismaleimide diphenylmethane is 2:3, the molar ratio of the intermediate product B to the epoxy resin is (1-2): 3, and curing for 2 hours under the heating condition of 120 ℃ to prepare the self-repairing tung oil-based shape memory polymer.
In the third step, the epoxy resin is E51 or dimer acid epoxy.
The molar ratio of the tung oil to the maleic anhydride added in the first step is 1:2.9.
The adding mole ratio of the intermediate product B to the epoxy resin in the third step is 1:3.
The self-repairing tung oil-based shape memory polymer prepared by the preparation method.
The application of the polymer in preparing self-repairing shape memory products.
The beneficial effects are that: (1) The invention introduces reversible dynamic covalent bond and dynamic ester bond, which can not only improve the shape memory capability of polymer material, but also make the material have certain self-repairing property. (2) The preparation process of the invention has simple route and controllable reaction, and the prepared product has stable property and certain utilization value. (3) The stiffness and flexibility characteristics can be adjusted by adjusting the ratio of 4,4' -bismaleimide diphenylmethane to epoxy resin that needs to be added during the third cure step.
Drawings
FIG. 1 initial fragmented material;
FIG. 2 is a diagram of a repair effect;
FIG. 3 is a serpentine initial state of the initial material cured to a bend in the mold;
FIG. 4 is an intermediate form cooled to room temperature;
FIG. 5 is a graph showing the recovery of the original shape within 10s after reheating at 65 ℃;
FIG. 6 is an infrared spectrum of tung oil, intermediate A and intermediate B of examples 1-7.
In the infrared spectrogram of tung oil, 1740cm -1 The distinct peak of (2) is the telescopic vibration absorption peak of c=o of the ester group. In the infrared spectrum of intermediate A, 1849cm -1 And 1775cm -1 The two distinct peaks at this point are characteristic peaks of anhydride groups and the low frequency peak is higher in intensity than the high frequency peak, indicating that intermediate A contains acidCyclic structure of anhydride groups. As can be seen from comparison of the infrared spectra of the intermediate A and the intermediate B, in the intermediate B, 1849cm of the anhydride group in the original intermediate A -1 And 1775cm -1 Two characteristic peaks disappear, 1708cm -1 The newly added peak is the absorption peak of C=O bond in carboxyl and ester group, which indicates a carboxyl and an ester group generated by acid anhydride ring opening. At the same time 2500-3000 cm in intermediate B -1 The formation of broad peaks also confirms the formation of carboxyl groups.
Detailed Description
No part is referred to herein as being identical to, or being implemented in, the prior art. The following are preferred embodiments of the present invention, but the present invention is not limited to the following only embodiments, and modifications of the embodiments are also considered as the scope of the present invention.
Example 1
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with 4,4' -bismaleimide diphenylmethane (molar amount is 150% of the molar amount of the intermediate product B) and an E51 epoxy resin (molar amount is 300% of the molar amount of the intermediate product B) and zinc acetylacetonate (mass is 1.5% of the total mass of the system), and cured for 2 hours under heating at 120 ℃ to prepare the self-repairing tung oil-based shape memory polymer.
Example 2
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with 4,4' -bismaleimide diphenylmethane (molar amount of which is 150% of the molar amount of the intermediate product B) and an E51 epoxy resin (molar amount of which is 225% of the molar amount of the intermediate product B, i.e., reduced to 75% based on the amount added in example 1) and zinc acetylacetonate (mass of which is 1.5% of the total mass of the system), and cured for 2 hours under heating at 120 ℃.
Example 3
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with 4,4' -bismaleimide diphenylmethane (in a molar amount of 150% of the molar amount of the intermediate product B) and dimer acid epoxy (in a molar amount of 150% of the molar amount of the intermediate product B), and cured for 2 hours under heating at 120 ℃ to prepare a self-repairing tung oil-based shape memory polymer.
Example 4
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with 4,4' -bismaleimide diphenylmethane (molar amount of which is 150% of the molar amount of the intermediate product B) and dimer acid epoxy (molar amount of which is 150% of the molar amount of the intermediate product B) and zinc acetylacetonate (mass of which is 1.5% of the total mass of the system), and cured for 2 hours under heating at 120℃to prepare a self-repairing tung oil-based shape memory polymer.
Example 5
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with 4,4' -bismaleimide diphenylmethane (molar amount of which is 150% of the molar amount of the intermediate product B) and dimer acid epoxy (molar amount of which is 112.5% of the molar amount of the intermediate product B), i.e., the addition amount was reduced to 75% based on example 4) and zinc acetylacetonate (mass of which is 1.5% of the total mass of the system), and cured for 2 hours under heating at 120 ℃.
Example 6
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with E51 epoxy resin (the molar amount is 300% of the molar amount of the intermediate product B) and zinc acetylacetonate (the mass is 1.5% of the total mass of the system), and cured for 2 hours at 120℃under heating to obtain a self-repairing tung oil-based shape memory polymer.
Example 7
The first step: adding tung oil and maleic anhydride into a reaction vessel according to the following molar ratio of 1:2.9, adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to the following molar ratio of 1:3, adding cetyltrimethylammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: the intermediate product B was mixed with dimer acid epoxy (molar amount is 150% of the molar amount of the intermediate product B) and zinc acetylacetonate (mass is 1.5% of the total mass of the system), and cured for 2 hours at 120℃under heating to obtain a self-repairing tung oil-based shape memory polymer.
The polymer materials prepared in the examples were prepared into test bars and tested for tensile mechanical properties, and the measurement results are shown in Table 1.
Table 1 comparison of the properties of the example groups
The polymeric material of example 5 was subjected to a self-healing property test: the initial fragmented material (as in figure 1) is hot pressed at 120 ℃ for 10min, and the complete restoration effect is achieved through the reconnection of dynamic bonds in the fragmented material (as in figure 2).
The polymeric material of example 5 was subjected to a shape memory performance test: the initial material is cured in the mold to a curved serpentine shape as an initial state, as shown in fig. 3, reshaped at 65 c, the curved serpentine shape is unfolded and cooled to room temperature to set to an intermediate shape, as shown in fig. 4, and heated again at 65 c to recover the initial shape within 10s, as shown in fig. 5.
Claims (6)
1. The preparation method of the self-repairing tung oil-based shape memory polymer is characterized by comprising the following steps: adding tung oil and maleic anhydride into a reaction vessel according to a molar ratio of (2.5-2.9), adding hydroquinone accounting for 0.5% of the total mass of the system, reacting for 3 hours at 180 ℃ to obtain an intermediate product A, and cooling to room temperature; secondly, adding the intermediate product A and furfuryl alcohol into a reaction vessel according to a molar ratio of 1:3, adding hexadecyl trimethyl ammonium chloride accounting for 0.5% of the total mass of the system, reacting for 4 hours at 85 ℃ to obtain an intermediate product B, and cooling to room temperature; and a third step of: mixing an intermediate product B with 4,4 '-bismaleimide diphenylmethane, epoxy resin and zinc acetylacetonate accounting for 1.5% of the total mass of the system, wherein the molar ratio of the intermediate product B to the 4,4' -bismaleimide diphenylmethane is 2:3, the molar ratio of the intermediate product B to the epoxy resin is (1-2): 3, and curing for 2 hours under the heating condition of 120 ℃ to prepare the self-repairing tung oil-based shape memory polymer.
2. The method of producing a self-repairing type tung oil-based shape memory polymer according to claim 1, wherein the epoxy resin in the third step is E51 or dimer acid epoxy.
3. The method for preparing a self-repairing type tung oil-based shape memory polymer according to claim 1, wherein the addition mole ratio of the tung oil to the maleic anhydride in the first step is 1:2.9.
4. The method for preparing a self-repairing tung oil-based shape memory polymer according to claim 1, wherein the addition molar ratio of the intermediate product B to the epoxy resin in the third step is 1:3.
5. A self-healing tung oil-based shape memory polymer prepared according to the method of any one of claims 1 to 4.
6. Use of the polymer of claim 5 for the preparation of a self-healing shape memory product.
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