CN114478976A - Palm oil-based thermoplastic polyurethane elastomer with suspended fatty acid chains and preparation method thereof - Google Patents
Palm oil-based thermoplastic polyurethane elastomer with suspended fatty acid chains and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of bio-based high polymer materials, and particularly relates to a palm oil-based thermoplastic polyurethane elastomer suspended by fatty acid chains and a preparation method thereof. The palm oil diethanolamide is synthesized by taking palm oil as a raw material, and the palm oil diethanolamide, hexamethylene diisocyanate and 1, 4-butanediol are further used for preparing the palm oil-based thermoplastic elastomer under the catalysis of organic tin. The palm oil-based elastomer prepared by the invention is not only environment-friendly in raw material sources, but also good in tensile property, recoverability and self-repairability.
Description
Technical Field
The invention belongs to the technical field of bio-based high polymer materials, and particularly relates to a palm oil-based thermoplastic polyurethane elastomer suspended by fatty acid chains and a preparation method thereof.
Background
Polyurethane elastomers are widely used in the industrial and medical fields, but the raw materials for synthesizing polyurethanes in the prior art are derived from non-renewable petroleum resources. Renewable resources are receiving increasing attention due to the current concept of sustainable development and the depletion of global fossil resources. Biomass resources including vegetable oils, carbohydrates, terpenes, and the like can be used in the synthesis of polymers. As a promising renewable resource, the vegetable oil has the advantages of abundant resources, no toxicity, environmental protection, abundant chemical derivatives and the like, and is widely applied to industry and academic research. Palm oil is the largest vegetable oil produced, consumed and traded worldwide. The palm oil has the characteristics of being renewable, rich in resources, low in cost, intensive in growth and the like, and has a good commercial utilization prospect. The basic structure of vegetable oil is triglyceride, and the number of unsaturated double bonds on fatty acid chains is variable, so the vegetable oil-based high polymer material prepared based on the vegetable oil-based high polymer material contains more flexible chains and crosslinking structures, and the mechanical strength and toughness of a plurality of polymers are poor, namely low elongation, low strength and modulus.
Polyurethane, a full name of polyurethane, is a high molecular compound, and is prepared by copolymerizing polyether/polyester polyol and diisocyanate. Because the polyurethane elastomer has 2 soft and hard chain segments, the polyurethane elastomer can endow the material with excellent performances such as high strength, good toughness, wear resistance, oil resistance and the like through the design of the chain segments. In the thermoplastic polyurethane elastomer, a hard segment is formed by diisocyanate and a chain extender together and mainly provides rigidity and strength for the material; the soft segment is generally composed of long-chain diol parts, which mainly increase the flexibility of the material. Among them, slight microphase separation of soft and hard segments has been confirmed to improve the properties of polyurethane elastomers. The long flexible fatty acid chain in the palm oil can serve as a soft segment of the polyurethane elastomer, and the chemical structure of triglyceride can be further synthesized into bio-based diol to react with diisocyanate, so that the palm oil-based thermoplastic polyurethane elastomer is obtained.
The invention takes palm oil-based diethanolamide as a raw material, and designs thermoplastic polyurethane which takes a fatty acid long chain of the palm oil diethanolamide as a side chain (a chain segment in the region is a soft segment) and a reaction segment of 1, 4-butanediol and HDI as a hard segment through the reaction with Hexamethylene Diisocyanate (HDI); meanwhile, the thermoplastic polyurethane elastomer with both strength and toughness is prepared by utilizing the control of the mutual winding of fatty acid side chains in molecules and the microphase separation of soft/hard sections. The preparation of the elastomer fully utilizes the bio-based palm oil, greatly develops an efficient utilization approach of palm oil resources, can reduce the use of petroleum-based products, and is beneficial to the development of low-carbon economy.
Disclosure of Invention
The invention aims to provide a thought for preparing a bio-based elastomer with excellent mechanical property by taking palm oil as a raw material, designs a palm oil-based thermoplastic polyurethane elastomer suspended by fatty acid chains, and solves the problems of poor mechanical property, difficult recovery, poor self-repairing property and the like of vegetable oil-based resin; the prepared palm oil-based elastomer is environment-friendly and has good tensile property, recoverability and self-repairability.
In order to achieve the purpose, the invention adopts the following technical scheme:
a palm oil-based thermoplastic polyurethane elastomer with a fatty acid chain suspended therein, the raw material comprising, in terms of mole ratio: 7-9 mol of palm oil diethanolamide, 10.5 mol of hexamethylene diisocyanate, 1-3 mol of 1, 4-butanediol and 0.08 mol of catalyst; the catalyst is dibutyltin dilaurate.
The palm oil diethanolamide is synthesized by taking palm oil and diethanolamide as raw materials and sodium methoxide as a catalyst; the specific synthetic process is as follows: a1000 mL three-necked flask equipped with mechanical stirring was placed in an oil bath and N was passed through2(ii) a Subsequently adding diethanolamine and sodium methoxide, stirring at 80 ℃ (150 r/min) for 10 min, adding palm oil, and heating to 120 ℃ to react for 4 h; and after the reactant is cooled, dissolving the reactant in ethyl acetate, repeatedly purifying the reactant for 3-5 times by using a saturated NaCl solution, and performing rotary evaporation for 3 hours to obtain the palm oil diethanolamide. What is needed isThe molar ratio of the diethanol amine to the palm oil is 6.5:1, and the molar ratio of the sodium methoxide to the palm oil is 1: 6.
The structural formula of the palm oil diethanolamide is as follows:
wherein R is1, R2, R3Is a saturated or unsaturated fatty acid.
A preparation method of a palm oil-based thermoplastic polyurethane elastomer suspended by fatty acid chains comprises the following specific steps: mixing palm oil diethanolamide, hexamethylene diisocyanate, catalyst andN,Nmixing dimethyl formamide in certain proportion and dissolving in three-neck flask in N2Protecting and stirring for 3 hours at 70 ℃; then dissolving a certain amount of chain extender 1, 4-butanediol in DMF, adding into the reaction system, and continuing stirring for 8 h; and finally, pouring the obtained solution into a polyfluortetraethylene container, placing the container at room temperature for drying for 24 hours, and curing at the temperature of 80 ℃ for 5 hours to obtain the elastomer.
The invention has the beneficial effects that:
(1) the palm oil-based elastomer prepared by the invention is an environment-friendly elastomer with high bio-based content and no toxic solvent; the elastomer has good tensile strength and elongation at break. Meanwhile, the palm oil which is low in price, large in yield, green and harmless is used as the raw material, and a novel method for preparing the thermoplastic elastomer from the palm oil is developed.
(2) The invention designs that vegetable oil fatty acid side chains are taken as soft segments, the side chains are mutually wound to form Van der Waals force, and the mechanical property of the elastomer is improved through the synergistic effect of hydrogen bonds and the Van der Waals force; meanwhile, 1, 4-butanediol is added to regulate and control the hard segment part on the main chain, so that the microphase separation dimension among the polyurethane elastomer molecules is regulated and controlled, and the mechanical property of the elastomer is further improved.
Drawings
FIG. 1 is a scheme of the synthesis reaction of palm oil diethanolamide;
FIG. 2 is a reaction scheme for the synthesis of palm oil-based elastomers;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum (1H NMR) of palm oil diethanolamide;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum (1H NMR) of a palm oil-based elastomer;
FIG. 5 is a tensile stress-strain curve of a palm oil-based elastomer;
FIG. 6 is a cyclic tensile stress-strain curve for POPU 1.5; cycle 1 represents the stress-strain curve for cycle 1; cycle 2 represents the stress-strain curve for 2 cycles; cycle 3 represents the stress-strain curve for 3 cycles; cycle 4 represents the stress-strain curve for 4 cycles; cycle 5 represents the stress-strain curve for 5 cycles. After the circulation 4 is finished, the sample strips recover for 10 hours at room temperature and then are circulated for 5;
FIG. 7 is a cyclic tensile stress-strain curve for POPU 2.5; cycle 1 represents the stress-strain curve for cycle 1; cycle 2 represents the stress-strain curve for 2 cycles; cycle 3 represents the stress-strain curve for 3 cycles; cycle 4 represents the stress-strain curve for 4 cycles; cycle 5 represents the stress-strain curve for 5 cycles. After the circulation 4 is finished, the sample strips recover for 10 hours at room temperature and then are circulated for 5;
FIG. 8 is a stress-strain curve of POPU1.5 after self-repairing at 100 ℃ for 24 h; wherein the control group represents the original stress-strain curve of the elastomer, and the self-repairing time of 24h represents the stress-strain curve of the elastomer after the elastomer is self-repaired for 24h at 100 ℃;
FIG. 9 is a stress-strain curve of POPU2.5 after self-repairing at 100 ℃ for 24 h; the control group represents the original stress-strain curve of the elastomer, and the self-repairing 24h represents the stress-strain curve of the elastomer after the elastomer is self-repaired for 24h at 100 ℃.
Detailed Description
For further disclosure, but not limitation, the present invention is described in further detail below with reference to examples.
Raw materials: palm oil (melting point: 18 ℃ C.; acid value: 0.16mg KOH/g) was purchased from Shanghai Dingfen chemical science and technology Co., Ltd., China; hexamethylene diisocyanate, 1, 4-butanediol, diethanolamine, dibutyltin dilaurate were obtained from Shanghai Crystal pure (Aladdin) industries, Inc.; sodium chloride, ethyl acetate, and sodium methoxide were purchased from Shanghai national pharmaceutical group chemical Co., Ltd.
The synthesis process of the palm oil diethanolamide comprises the following steps:
a1000 mL three-necked flask equipped with mechanical stirring was placed in an oil bath and N was passed through2(ii) a Subsequently adding diethanolamine and sodium methoxide, stirring at 80 ℃ (150 r/min) for 10 min, adding palm oil, and heating to 120 ℃ to react for 4 h; and after the reactant is cooled, dissolving the reactant in ethyl acetate, repeatedly purifying the reactant for 3-5 times by using a saturated NaCl solution, and performing rotary evaporation for 3 hours to obtain the palm oil diethanolamide, wherein the molar ratio of the diethanolamide to the palm oil is 6.5:1, and the molar ratio of the sodium methoxide to the palm oil is 1: 6.
The preparation method of the palm oil-based thermoplastic polyurethane elastomer with the fatty acid chain suspended specifically comprises the following steps: mixing palm oil diethanolamide, hexamethylene diisocyanate, catalyst andN,Nmixing dimethyl formamide in certain proportion and dissolving in three-neck flask in N2Protecting and stirring for 3 hours at 70 ℃; then dissolving a certain amount of chain extender 1, 4-butanediol in DMF, adding into the reaction system, and continuously stirring for 8 h; finally, the resulting solution was poured into a polyfluortetraethylene plate (10X 10 cm)2) Then drying the mixture at room temperature for 24 hours, and curing the mixture at 80 ℃ for 5 hours to obtain the elastomer.
Example 1
Preparation of palm oil-based elastomer:
palm oil diethanolamide (2.38 g), hexamethylene diisocyanate (1.76 g), catalyst (0.1 g) andN,N-dimethylformamide (5 mL) mixed and dissolved in a three-necked flask under N2Protecting and stirring for 3 hours at 70 ℃; then dissolving 0.09 g of chain extender 1, 4-butanediol in 60 mL of DMF, adding into the reaction system, and continuing stirring for 8 h; and finally, pouring the obtained solution into a polyfluortetraethylene container, placing the container at room temperature for drying for 24 hours, and curing at the temperature of 80 ℃ for 5 hours to obtain the elastomer.
In the preparation process, the dosage ratio of hexamethylene diisocyanate, palm oil diethanolamide and 1, 4-butanediol is 10.5 mmol, 9 mmol and 1 mmol in terms of mol; the catalyst dibutyltin dilaurate was 0.08 mmol.
Example 2
Preparation of palm oil-based elastomer:
palm oil diethanolamide (2.25 g), hexamethylene diisocyanate (1.76 g), catalyst (0.1 g) andN,N-dimethylformamide (5 mL) mixed and dissolved in a three-necked flask under N2Protecting and stirring for 3 hours at 70 ℃; then 0.135 g of chain extender 1, 4-butanediol is dissolved in 60 mL of DMF and added into the reaction system, and the mixture is continuously stirred for 8 h; and finally, pouring the obtained solution into a polyfluortetraethylene container, placing the container at room temperature for drying for 24 hours, and curing at the temperature of 80 ℃ for 5 hours to obtain the elastomer.
In the preparation process, the dosage ratio of hexamethylene diisocyanate, palm oil diethanolamide and 1, 4-butanediol is 10.5 mmol, 8.5 mmol and 1.5 mmol in terms of mol; the catalyst dibutyltin dilaurate was 0.08 mmol.
Example 3
Preparation of palm oil-based elastomer:
palm oil diethanolamide (2.12 g), hexamethylene diisocyanate (1.76 g), catalyst (0.1 g) andN,N-dimethylformamide (5 mL) mixed and dissolved in a three-necked flask under N2Protecting and stirring for 3 hours at 70 ℃; then 0.18 g of chain extender 1, 4-butanediol is dissolved in 60 mL of DMF and added into the reaction system, and the mixture is continuously stirred for 8 h; and finally, pouring the obtained solution into a polyfluortetraethylene container, placing the container at room temperature for drying for 24 hours, and curing at the temperature of 80 ℃ for 5 hours to obtain the elastomer.
In the preparation process, the dosage ratio of hexamethylene diisocyanate, palm oil diethanolamide and 1, 4-butanediol is 10.5 mmol, 8 mmol and 2 mmol in terms of mol; the catalyst dibutyltin dilaurate was 0.08 mmol.
Example 4
Preparation of palm oil-based elastomer:
palm oil diethanolamide (1.98 g), hexamethylene diisocyanate (1.76 g), catalyst (0.1 g) andN,N-dimethylformamide (5 mL) mixed and dissolved in a three-necked flask under N2Protecting and stirring for 3 hours at 70 ℃; then dissolving 2.25g of chain extender 1, 4-butanediol in 60 mL of DMF, adding into the reaction system, and continuing stirring for 8 h; finally, the resulting solution is mixedPouring into a polyfluortetraethylene container, drying at room temperature for 24h, and curing at 80 ℃ for 5 h to obtain the elastomer.
In the preparation process, the usage ratio of hexamethylene diisocyanate, palm oil diethanolamide and 1, 4-butanediol is 10.5 mmol, 7.5 mmol and 2.5 mmol in terms of molar ratio; the catalyst dibutyltin dilaurate was 0.08 mmol.
Example 5
Preparation of palm oil-based elastomer:
palm oil diethanolamide (1.85 g), hexamethylene diisocyanate (1.76 g), catalyst (0.1 g) andN,N-dimethylformamide (5 mL) mixed and dissolved in a three-necked flask under N2Protecting and stirring for 3 hours at 70 ℃; then 0.27 g of chain extender 1, 4-butanediol is dissolved in 60 mL of DMF and added into the reaction system, and the mixture is continuously stirred for 8 h; and finally, pouring the obtained solution into a polyfluortetraethylene container, placing the container at room temperature for drying for 24 hours, and curing at the temperature of 80 ℃ for 5 hours to obtain the elastomer.
In the preparation process, the dosage ratio of hexamethylene diisocyanate, palm oil diethanolamide and 1, 4-butanediol is 10.5 mmol, 7 mmol and 3 mmol in terms of mol; the catalyst dibutyltin dilaurate was 0.08 mmol.
Nuclear magnetic resonance hydrogen spectra of palm oil diethanolamide and palm oil-based elastomer (1H NMR) test:
an AvanceIII400WB spectrometer (Bruker, BioSpin, Switzerland (testing the NMR spectra of palm oil diethanolamide and palm oil-based elastomers: (R))1H NMR) using deuterated chloroform (δ (1H) =7.27 ppm) as a solvent.
Tensile property test of elastomer:
the elastomer was made into a dumbbell-shaped specimen (specification: 75mm in length, 12.5mm in width at both ends, 4mm in width at the middle, 0.5mm in thickness) to test tensile properties; tensile properties were tested according to GB/T528-1998 standard. The tensile property test and the cyclic tensile property test are both completed on a microcomputer control electronic universal tester.
POPU1 represents an elastomer with a 1: 9 ratio of 1, 4-butanediol to palm oil-based diethanolamide; POPU1.5 represents an elastomer with a 1.5: 8.5 ratio of 1, 4-butanediol to palm oil based diethanolamide; POPU2 represents an elastomer with a ratio of 1, 4-butanediol to palm oil based diethanolamide of 2: 8; POPU2.5 represents an elastomer with a ratio of 1, 4-butanediol to palm oil-based diethanolamide of 2.5: 7.5; POPU1 represents an elastomer with a ratio of 1, 4-butanediol to palm oil diethanolamide of 3: 7.
As can be seen from fig. 1 and 3, palm oil-based diethanolamide can be synthesized from palm oil and diethanol amine.
As can be seen from fig. 2 and 4, the palm oil-based thermoplastic polyurethane with a pendant fatty acid chain can be synthesized from palm oil-based diethanolamide and hexamethylene diisocyanate, 1, 4-butanediol.
As is clear from FIG. 5, the tensile stresses of the elastomers POPU1, POPU1.5, POPU2, POPU2.5 and POPU3 were 1.16MPa, 2.75MPa, 3.8MPa, 8.31MPa and 9.52MPa, respectively. The elongation at break of the elastomers POPU1, POPU1.5, POPU2, POPU2.5 and POPU3 were 609%, 812%, 661%, 573% and 511%, respectively. The tensile strength of the elastomer increases with increasing 1, 4-butanediol, but the elongation at break of the elastomer tends to increase and then decrease, with the highest elongation at break of POPU 1.5.
As shown in FIG. 6, the stress-strain hysteresis loop of POPU1.5 decreases with increasing cycle number within 2-4 cycles; after 10h recovery, the cycle lag ring is slightly larger than that of the 2 nd cycle, and the 5 th cycle lag ring loses only 0.53MJ/m of energy3。
As can be seen from FIG. 7, the hysteresis loop of POPU2.5 decreases with increasing cycle number within 2-4 cycles, wherein the 2 nd cycle hysteresis loop has a loss energy of up to 18.2 MJ/m3(ii) a After 10h recovery, the hysteresis loop is larger than the 2 nd cycle, and the hysteresis loop of the 5 th cycle loses 5.4MJ/m energy3。
As shown in FIG. 8, after the POPU1.5 is self-repaired at 100 ℃ for 24 hours, the stress and the strain are respectively 2.36MPa and 811 percent, and the recovery efficiency of the stress and the strain is 85.3 percent and 99.8 percent.
As shown in FIG. 9, after the POPU2.5 is self-repaired at 100 ℃ for 24 hours, the stress and the strain are respectively 7.31MPa and 525%, and the recovery efficiency of the stress and the strain is 87.9% and 91.6%.
The above description is only a preferred embodiment of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Claims (6)
1. A palm oil-based thermoplastic polyurethane elastomer with a fatty acid chain pendant, characterized by: the raw materials comprise the following components in mol: 7-9 mol of palm oil diethanolamide, 10.5 mol of hexamethylene diisocyanate, 1-3 mol of 1, 4-butanediol and 0.08 mol of catalyst; the catalyst is dibutyltin dilaurate.
2. The fatty acid chain suspended palm oil-based thermoplastic polyurethane elastomer of claim 1, wherein: the palm oil diethanolamide is synthesized by taking palm oil and diethanolamide as raw materials and sodium methoxide as a catalyst.
3. The fatty acid chain suspended palm oil-based thermoplastic polyurethane elastomer of claim 2, wherein: the synthesis process of the palm oil diethanolamide comprises the following steps: mixing diethanolamine and sodium methoxide under the protection of nitrogen, then adding palm oil, heating to 120 ℃ to react for 4 hours, cooling, purifying and rotary steaming to obtain the palm oil diethanolamide.
4. The fatty acid chain suspended palm oil-based thermoplastic polyurethane elastomer of claim 3, wherein: the molar ratio of the diethanolamine to the palm oil is 6.5:1, and the molar ratio of the sodium methoxide to the palm oil is 1: 6.
5. The fatty acid chain suspended palm oil-based thermoplastic polyurethane elastomer of claim 3, wherein: the synthesis process of the palm oil diethanolamide specifically comprises the following steps: a1000 mL three-necked flask equipped with mechanical stirring was placed in an oil bath and N was passed through2(ii) a Adding diethanolamine and sodium methoxide, stirring at 80 deg.C for 10 min, adding palm oil, and heating to 120 deg.C to obtain oilReacting for 4 hours; and after the reactant is cooled, dissolving the reactant in ethyl acetate, repeatedly purifying the reactant for 3-5 times by using a saturated NaCl solution, and performing rotary evaporation for 3 hours to obtain the palm oil diethanolamide.
6. A method of preparing the fatty acid chain-suspended palm oil-based thermoplastic polyurethane elastomer of any one of claims 1 to 5, wherein: the method comprises the following specific steps: mixing palm oil diethanolamide, hexamethylene diisocyanate, catalyst andN,N-dimethylformamide in N2Protecting and stirring for 3 hours at 70 ℃; dissolving 1, 4-butanediol in DMF, adding the solution into a reaction system, and continuously stirring for 8 hours; and finally, pouring the obtained solution into a polyfluortetraethylene container, placing the container at room temperature for drying for 24 hours, and curing at the temperature of 80 ℃ for 5 hours to obtain the elastomer.
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