CN115558071B - Self-repairing polyurethane composite material and preparation method and application thereof - Google Patents
Self-repairing polyurethane composite material and preparation method and application thereof Download PDFInfo
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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
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
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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
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
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- C08K3/34—Silicon-containing compounds
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
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Abstract
The invention discloses a self-repairing polyurethane composite material, a preparation method and application thereof, wherein nano BaTiO is added into DA-type self-repairing polyurethane material 3 And SiC, and researches the comprehensive performance of the self-repairing polyurethane composite material. At the same time, in order to improve nano BaTiO 3 By using the dispersibility of tartaric acid to BaTiO 3 The performance influence of filler modification on the self-repairing polyurethane composite material is studied by modifying. The invention prepares polyurethane prepolymer by synthesizing prepolymer, and introduces furan-maleimide system as self-repairing reversible covalent bond. By adding filler BaTiO into self-repairing polyurethane material 3 And SiC to improve the dielectric and thermal properties of the material and to study the effect of the ratio of the two materials on each property.
Description
Technical Field
The invention belongs to the field of polyurethane materials, and particularly relates to a self-repairing polyurethane composite material, and a preparation method and application thereof.
Background
The repairing effect of the existing self-repairing material only shows mechanical property, and the self-repairing material studied at present only has the characteristic of self-repairing, and other properties besides mechanical property are quite modest, which is not beneficial to widening the application of self-repairing. At present, on the basis of not affecting the mechanical property and the self-repairing property of the polymer, the additional characteristics (such as dielectric property, heat conducting property and the like) are given to the material, and the material is a great challenge for researchers. In addition, the addition of fillers to polymers is generally not easy to shape.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a self-repairing polyurethane composite material and a preparation method and application thereof. The invention enhances the dielectric property and the heat conduction property of the material without affecting the self-repairing property of the material, thereby widening the application range of the polyurethane self-repairing material.
The aim of the invention is achieved by the following technical scheme:
a preparation method of a self-repairing polyurethane composite material comprises the following steps:
(1) Mixing polypropylene glycol and polyether polyol, heating to 100-120 ℃ in an oil bath under vacuum pumping, removing water, adding diphenylmethane-4, 4' -diisocyanate and a catalyst after the system temperature is reduced to room temperature, and heating to 60-80 ℃ for reacting for 1-2 h to obtain isocyanate-terminated polyurethane prepolymer (PU-NCO); the temperature is reduced to 30-40 ℃, furfuryl amine solution is added into a reaction system, after the addition is finished, the reaction is carried out for 1-2 hours, then the temperature is increased to 60-80 ℃ for 1-2 hours, and the polyurethane prepolymer (PU-FAm) with end furan ring end closure is obtained;
(2) Preparing tartaric acid aqueous solution, regulating pH of the tartaric acid aqueous solution to 8-9, adding nano BaTiO while stirring 3 Heating to 50-70 ℃ and then reacting for 1-2 h, and filtering the BaTiO in the reacted mixed solution 3 Separating out the powder, washing with weak alkaline solution after filtering, and washing with water; drying the rinsed powder to obtain modified BaTiO 3 ；
(3) The modified BaTiO 3 Mixing SiC and bismaleimide diphenylmethane (BMI), dissolving in N, N-dimethylformamide after mixing, dispersing uniformly by ultrasonic, adding the polyurethane prepolymer blocked by the furan ring in the step (1), dispersing uniformly by ultrasonic again, pouring into a mould, and heating at 60-80 ℃ for 12-24 hours to obtain the self-repairing polyurethane composite material.
Preferably, the mass ratio of the polypropylene glycol to the polyether polyol in the step (1) is 3-6: 1 to 2.
Preferably, the polypropylene glycol in step (1) is at least one of PPG2000, PPG400 and PPG 1000.
Preferably, the polyether polyol of step (1) is at least one of HSH-310 and HSH 330.
Preferably, the mass ratio of the diphenylmethane-4, 4' -diisocyanate to the polypropylene glycol in the step (1) is 1-2: 3 to 6.
Preferably, the catalyst in the step (1) is at least one of dibutyl tin dilaurate, dimethyl cyclohexylamine and dimethylaminoethyl ether.
Preferably, the catalyst in the step (1) accounts for 0.1-0.3% of the total mass of the polypropylene glycol and the polyether polyol.
Preferably, the furfuryl amine solution in the step (1) is an N-N dimethylformamide solution with the concentration of 20-40 wt%.
Preferably, the mass ratio of the furfuryl amine solution to the polypropylene glycol in the step (1) is 1-2: 2 to 4.
Preferably, the mass percentage of the tartaric acid aqueous solution in the step (2) is 4-8wt%.
Optionally, the nano BaTiO in the step (2) 3 The particle size of (2) is 50-100 nm.
Preferably, the nano BaTiO of step (2) 3 The mass ratio of the compound to tartaric acid is 2-5: 1 to 3.
Preferably, the weakly alkaline solution in the step (2) is at least one of ammonia water and hydrogen peroxide.
Preferably, the temperature of the drying in the step (2) is 60-80 ℃.
Preferably, the particle size of the SiC of step (3) is 500-700 nm.
Preferably, the modified BaTiO of step (3) 3 And the mass ratio of SiC is 2: 8-8:2.
Preferably, the mass ratio of the bismaleimide diphenylmethane in the step (3) to the polyether polyol in the step (1) is 1-3:1-3.
Preferably, the mass ratio of the addition amount of the N, N-dimethylformamide to the bismaleimide diphenylmethane in the step (3) is 1-6: 2 to 4.
Preferably, the furan ring-terminated polyurethane prepolymer of step (3) is reacted with BaTiO 3 The ratio of the total mass of the SiC to the SiC is 1:5-20%.
The self-repairing polyurethane composite material is prepared by the preparation method of the self-repairing polyurethane composite material.
The self-repairing polyurethane composite material is applied to buildings, traffic, medical treatment, novel intelligent flexible elements and tensile strain sensors.
Compared with the prior art, the invention has the beneficial effects that:
(1) The self-repairing polyurethane composite material prepared by the invention introduces a double benzene ring structure, so that not only can the rigidity of a molecular chain be increased, but also the polymer after the nano filler is added can be molded more easily. The reaction can be carried out under a mild condition, and the self-repairing polymer prepared by DA reaction only depends on self dynamic chemical bonds in the repairing process, so that multiple repairing can be realized; the synthesis route is flexible, the repair temperature of the material can be controlled by adjusting the types of diene and dienophile, and the application range is wide. The preparation process of the polymer can be realized by directly polymerizing small molecules with multiple functionalities or modifying some existing high molecular polymers;
(2) To improve nano BaTiO 3 By using the dispersibility of tartaric acid to BaTiO 3 Modifying, preparing polyurethane prepolymer by synthesizing prepolymer, and introducing furan-maleimide system as self-repairing reversible covalent bond. The addition of the functional nano filler greatly improves the dielectric property and the conductivity of the self-repairing polyurethane by adopting a soft and hard phase structure and improving the strength and the variety of dynamic acting force between molecular chains.
Drawings
FIG. 1 is a graph showing the dielectric constant properties of the products prepared in examples 1 to 5 and comparative example 1 before repair.
FIG. 2 is a graph showing the dielectric constant properties of the products prepared in examples 1 to 5 and comparative example 1 after repair.
FIG. 3 is a graph showing dielectric loss properties before repair of the products prepared in examples 1 to 5 and comparative example 1.
FIG. 4 is a graph showing dielectric loss properties after repair of the products prepared in examples 1 to 5 and comparative example 1.
FIG. 5 is a graph showing the change in heat conductive properties before and after repair of the products prepared in examples 1 to 5 and comparative example 1.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
Example 1
A preparation method of a self-repairing polyurethane composite material comprises the following steps:
(1) Into a dry three-neck flask was added 30g of polypropylene glycol (PPG 2000), 10g of polyether polyol (HSH-310), which was then heated to 120℃with an oil bath under a pump vacuum, and dehydrated under vacuum for 2 hours. After water removal, the system was cooled to room temperature, then 15g of diphenylmethane-4, 4' -diisocyanate (MDI) and 0.1g of dibutyltin dilaurate were taken and added as a catalyst, and the reaction was carried out for 2 hours at a temperature of 80℃to obtain an isocyanate-terminated polyurethane prepolymer (PU-NCO). The temperature was lowered to 40℃and 5.83g of furfuryl amine was dissolved in 10mL of N-N Dimethylformamide (DMF), and the mixture was added dropwise to the above system at a rate of 1 to 3 seconds per drop by means of a constant pressure funnel, and after the completion of the addition, the reaction was carried out for 1 hour, and then the temperature was raised to 60℃for 2 hours, to give a polyurethane prepolymer (PU-FAm) terminated with a terminal furan ring.
(2) Weighing 3.2g of tartaric acid particles, dissolving in 50ml of deionized water, regulating the PH of tartaric acid to 8-9 by using a concentrated NaOH solution, placing the regulated solution into a three-neck flask, stirring at a speed of 40rpm/s, and controlling the stirring speed to be unchanged; weighing 5.0g of nano BaTiO 3 Adding the mixture into a three-neck flask, heating to 50 ℃ and then reacting for 2 hours, wherein the temperature and the stirring speed are controlled unchanged; filtering the mixed solution after reaction to obtain BaTiO 3 Separating out the powder, and after filtering, firstly rinsing with 5% hydrogen peroxide solution and then rinsing with water; drying the rinsed powder in oven at 60deg.CObtaining modified BaTiO 3 ；
(3) 0.2g of modified BaTiO 3 Mixing 0.8g of SiC and 10.75g of bismaleimide diphenylmethane (BMI), dissolving the mixture in 30mL of N, N-dimethylformamide, uniformly dispersing by ultrasonic, adding 10g of the furan ring end-capped polyurethane prepolymer in the step (1), uniformly dispersing by ultrasonic again, pouring into a mould, and heating at 60 ℃ for 12 hours to obtain the self-repairing polyurethane composite material.
Example 2
A preparation method of a self-repairing polyurethane composite material comprises the following steps:
(1) As in example 1;
(2) As in example 1;
(3) Modified BaTiO 3 0.4g of SiC and 0.6g of SiC were used in the same manner as in example 1.
Example 3
A preparation method of a self-repairing polyurethane composite material comprises the following steps:
(1) As in example 1;
(2) As in example 1;
(3) Modified BaTiO 3 0.5g of SiC and 0.5g of SiC were used in the same manner as in example 1.
Example 4
A preparation method of a self-repairing polyurethane composite material comprises the following steps:
(1) As in example 1;
(2) As in example 1;
(3) Modified BaTiO 3 0.6g of SiC and 0.4g of SiC were obtained in the same manner as in example 1.
Example 5
A preparation method of a self-repairing polyurethane composite material comprises the following steps:
(1) As in example 1;
(2) As in example 1;
(3) Modified BaTiO 3 0.8g of SiC and 0.2g of SiC were obtained in the same manner as in example 1.
Comparative example 1
A preparation method of polyurethane material comprises the following steps:
(1) Same as in example 1
(2) 10.75g of bismaleimide diphenylmethane (BMI) was dissolved in 30mL of N, N-dimethylformamide, heated at 65℃until the powder completely disappeared, then thoroughly mixed with 10g of the furan ring-terminated polyurethane prepolymer PU-FAm described in step (1), poured into a polytetrafluoroethylene mold after ultrasonic treatment, cured for 12 hours at 60℃in a constant temperature oven, and finally released from the mold to obtain a sample.
The products prepared in examples 1 to 5 and comparative example 1 were subjected to a test for repair properties. Cutting out corresponding samples by using a cutter according to the GBT528-2009 national standard, heating the samples at 120 ℃ for 20min after cutting the samples, then preserving the heat at 60 ℃ for 12 hours to obtain corresponding repair samples, carrying out 3 samples on each group, and carrying out tensile test on the two groups of samples by adopting an ICS-2000 universal tester under the condition of room temperature. The data adopts the average value of each group of data, the self-repairing efficiency is represented by the ratio of the tensile strength before and after spline repairing, and the self-repairing efficiency calculation formula is as follows: r (σ) =σpurified/σinitial (where σpurified, σinitial is the tensile strength after repair and the tensile strength before repair, respectively). The repair experiment shows that the repair conditions of the self-repair polyurethane are as follows: repairing is carried out at the temperature of 120 ℃ for 20min, and the repairing efficiency can reach 98 percent.
Dielectric property test: a conductive silver paste (purchased from Shanghai Xinluyi electronic materials Co., ltd.; specification: SS-5200) with a thickness of 0.1mm was uniformly coated on both sides of the sample, and the sample was subjected to dielectric testing by an LCR dielectric spectrum analyzer.
And (3) testing heat conduction performance: and testing the heat conductivity of the sample by adopting a DRL-3 type automatic heat conductivity tester, wherein the temperature of a hot electrode is 70 ℃, the temperature of a cold electrode is 30 ℃, the single test time is set to 300s, and each sample is tested for 5 times and the average value is taken to obtain the heat conductivity of the sample before restoration.
FIG. 1 is a graph showing the dielectric constant properties of the products prepared in examples 1 to 5 and comparative example 1 before repair. FIG. 2 is a graph showing the dielectric constant properties of the products prepared in examples 1 to 5 and comparative example 1 after repair.
FIG. 3 is a graph showing dielectric loss properties before repair of the products prepared in examples 1 to 5 and comparative example 1. FIG. 4 is a graph showing dielectric loss properties after repair of the products prepared in examples 1 to 5 and comparative example 1.
The dielectric property test shows that: the addition of BT and SiC improves the dielectric constant of the composite material, and in the three-phase composite material, the following BT: sic=2: 8, the dielectric property effect is best that the dielectric constant can reach 15 at most, which is improved by about 1 time compared with pure polyurethane, and the dielectric loss is slightly increased.
FIG. 5 is a graph showing the change in heat conductive properties before and after repair of the products prepared in examples 1 to 5 and comparative example 1. The heat conduction performance test shows that: the three-phase composite material also shows that the optimal proportion is BT: sic=2: 8, the heat conductivity coefficient of the material reaches 0.26 at most, and the material is improved by about 117 percent. Simultaneously, the dielectric property and the heat conducting property of the material can be repaired along with the repair of the material, the BT is subjected to surface modification by using tartaric acid, and the influence of filler modification on the performance of the composite material is explored. It was also found in the dielectric properties test that modified BT: sic=2: 8, the dielectric constant of the material can reach 16 at most, which is 100% higher than that of pure polyurethane, and the BT particles are modified to improve the dielectric property of the composite material to a certain extent; moreover, the modification of BT also improves the stability of the heat conductivity coefficient before and after material repair.
The above-described embodiments of the present invention do not limit the scope of the present invention. Any other corresponding changes and modifications made in accordance with the technical idea of the present invention shall be included in the scope of the claims of the present invention.
Claims (10)
1. The preparation method of the self-repairing polyurethane composite material is characterized by comprising the following steps of:
(1) Mixing polypropylene glycol and polyether polyol, heating to 100-120 ℃ in an oil bath under vacuum pumping, removing water, adding diphenylmethane-4, 4' -diisocyanate and a catalyst after the system temperature is reduced to room temperature, and heating to 60-80 ℃ for reacting for 1-2 hours to obtain isocyanate-terminated polyurethane prepolymer; the temperature is reduced to 30-40 ℃, furfuryl amine solution is added into a reaction system, after the addition is finished, the reaction is carried out for 1-2 hours, the temperature is increased to 60-80 ℃ for 1-2 hours, and the polyurethane prepolymer with the end blocked by furan rings is obtained;
the polyether polyol in the step (1) is at least one of HSH-310 and HSH 330;
(2) Preparing an aqueous tartaric acid solution, regulating the pH of the aqueous tartaric acid solution to 8-9, and adding nano BaTiO while stirring 3 Heating to 50-70 ℃ and then reacting for 1-2 h, and filtering to obtain BaTiO in the reacted mixed solution 3 Separating out the powder, washing with weak alkaline solution after filtering, and washing with water; drying the rinsed powder to obtain modified BaTiO 3 ；
(3) The modified BaTiO 3 Mixing SiC and bismaleimide diphenylmethane (BMI), dissolving the mixture in N, N-dimethylformamide, dispersing the mixture uniformly by ultrasonic, adding the polyurethane prepolymer blocked by the furan ring in the step (1), dispersing the mixture uniformly by ultrasonic again, pouring the mixture into a mold, and heating the mixture at 60-80 ℃ for 12-24 hours to obtain the self-repairing polyurethane composite material.
2. The preparation method of the self-repairing polyurethane composite material according to claim 1, wherein the mass ratio of the polypropylene glycol to the polyether polyol in the step (1) is 3-6: 1-2;
the mass ratio of the furfuryl amine solution to the polypropylene glycol in the step (1) is 1-2: 2-4;
step (2) the nano BaTiO 3 The mass ratio of the compound to the tartaric acid is 2-5: 1-3.
3. The method for producing a self-repairing polyurethane composite material according to claim 2, wherein the modified BaTiO of step (3) is 3 And the mass ratio of SiC is 2: 8-8:2;
the mass ratio of the bismaleimide diphenylmethane to the polyether polyol in the step (1) is 1-3:1-3.
4. The preparation method of the self-repairing polyurethane composite material according to claim 1, wherein the mass ratio of the addition amount of the N, N-dimethylformamide to the bismaleimide diphenylmethane in the step (3) is 1-6: 2-4;
the mass ratio of the diphenylmethane-4, 4' -diisocyanate to the polypropylene glycol in the step (1) is 1-2: 3-6.
5. The method for preparing the self-repairing polyurethane composite material according to any one of claims 1 to 4, wherein the mass of the catalyst added in the step (1) is 0.1% -0.3% of the total mass;
step (3) the furan ring-terminated polyurethane prepolymer and BaTiO 3 The ratio of the total mass of SiC to SiC is 1:5% -20%.
6. The method of producing a self-healing polyurethane composite according to claim 5, wherein the polypropylene glycol of step (1) is at least one of PPG2000, PPG400 and PPG 1000;
the catalyst in the step (1) is at least one of dibutyl tin dilaurate, dimethyl cyclohexylamine and dimethylaminoethyl ether.
7. The method for preparing a self-repairing polyurethane composite material according to any one of claims 1 to 4, wherein the furfuryl amine solution in the step (1) is an N-N dimethylformamide solution with the concentration of 20 to 40 wt%;
the mass percentage of the tartaric acid aqueous solution in the step (2) is 4-8wt%;
step (2) the nano BaTiO 3 The particle size of (2) is 50-100 nm.
8. The method for preparing a self-repairing polyurethane composite material according to claim 7, wherein the weakly alkaline solution in the step (2) is at least one of ammonia water and hydrogen peroxide;
the drying temperature in the step (2) is 60-80 ℃;
and (3) the particle size of the SiC is 500-700 nm.
9. The self-repairing polyurethane composite material prepared by the preparation method of the self-repairing polyurethane composite material according to any one of claims 1-8.
10. Use of the self-healing polyurethane composite of claim 9 in construction, traffic, smart flexible elements and tensile strain sensors.
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