CN115304764B - Epoxidized fluorine-containing polyarylether compound and preparation method thereof - Google Patents
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- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
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Abstract
The invention relates to an epoxidized fluorine-containing polyarylether compound and a preparation method thereof. According to the invention, decafluorobiphenyl and 2, 2-diallyl bisphenol A are used as raw materials, an allyl-containing ABA monomer is synthesized, then polymerized with bisphenol A to obtain high molecular weight allyl-containing fluorine-containing polyarylether, and finally m-chloroperoxybenzoic acid is used for oxidizing double bonds into epoxy groups to obtain the epoxidation fluorine-containing polyarylether compound. The invention has simple process and high epoxy group content, and the product can be used for preparing paint, composite material and the like.
Description
Technical Field
The invention belongs to the technical field of materials, and particularly relates to an epoxidized fluorine-containing polyarylether compound and a preparation method thereof.
Background
The polyarylether is a high molecular compound formed by connecting aromatic benzene rings and ether bonds, becomes one of research hot spot materials due to the excellent physical and chemical characteristics such as thermal stability, mechanical strength, chemical stability and the like, low cost, easy processing and other engineering advantages, and is widely applied to the fields of automobiles, aviation, biomedicine, new energy sources and the like. However, although the polyarylether has excellent performance, the current industrial requirements cannot be met with the development of the times, so that the development of novel high-performance polyarylether and related products thereof is required to meet the higher use requirements. Wang (Polymer Chemistry,2021,12 (26): 3753-3761) et al synthesized an epoxy-terminated fluorine-containing polyaryletherketone (EFPAEK) and modified bisphenol A dicyanate (BADCy) resins with epoxy groups that promote the curing process and thereby increase the compatibility of the resins. The interpenetrating polymer network formed between EFPAEK and the cured BADCy resin may improve its mechanical properties. In addition, the low-polarization-CF groups can attenuate the polarization effect of the applied electric field, thereby reducing the dielectric constant and dielectric loss tangent of the BADCy resin. However, the EFPAEK has low epoxy group content, and only distributes at two ends of the polymer, so that the modification effect is limited.
The invention aims to provide an epoxidized fluorine-containing polyarylether compound (EFPAE) and a preparation method thereof. The high epoxy group content, good chemical stability, high molecular weight, low dielectric constant, good hydrophobicity and the like of the invention can be used as raw materials of resin, paint, adhesive, ultralow dielectric material, superhydrophobic material and the like, and has great significance in the field of resin modification.
Disclosure of Invention
The invention aims to provide an epoxidized fluorine-containing polyarylether compound.
Another object of the present invention is to provide a process for preparing the above epoxidized fluorine-containing polyarylether compound.
An epoxidized fluorine-containing polyarylether compound has a chemical structural formula shown as follows:
wherein n=10 to 100.
The preparation method of the epoxidized fluorine-containing polyarylether compound comprises the following steps:
(1) Adding 2, 2-diallyl bisphenol A and decafluorobiphenyl into N-methyl pyrrolidone to prepare a solution with the mass concentration of 1-30%, introducing argon, magnetically stirring at room temperature until the solution is completely dissolved, adding calcium hydride, stirring for 5-10 min, adding cesium fluoride to react for 24-48 h, pouring the obtained solution into deionized water, precipitating and filtering, vacuum drying at 60-80 ℃, and purifying by using a chromatographic silica gel column by using petroleum ether as a mobile phase to obtain an ABA monomer containing allyl; the reaction formula is as follows:
(2) Adding an allyl-containing ABA type monomer and bisphenol A into N-methylpyrrolidone to prepare a solution with the mass concentration of 1-30%, introducing argon, magnetically stirring at room temperature until the solution is completely dissolved, adding calcium hydride, stirring for 5-10 min, adding cesium fluoride to react for 24-48 h, pouring the obtained solution into deionized water to precipitate and filter, drying in a vacuum oven at 60-80 ℃ for 12-24 h, pouring the solution into dichloromethane to completely dissolve, pouring the solution into methanol to precipitate and filter, and drying in the vacuum oven at 60-80 ℃ for 12-24 h to obtain fluorine-containing polyarylether containing allyl; the reaction formula is as follows:
(3) Dissolving fluorine-containing polyarylether containing allyl into anhydrous dichloromethane to prepare a solution with the mass concentration of 1-30%, reacting for 2-4 hours at the temperature of 0-10 ℃ by taking M-chloroperoxybenzoic acid (mCPBA) as an oxidant, then adding 0.1-1M NaOH aqueous solution, stirring for 1-5 minutes, extracting with 2-10% of saline water by mass fraction, slowly pouring a dichloromethane phase into methanol to precipitate, filtering, and drying for 12-24 hours at the temperature of 60-80 ℃ in a vacuum oven to obtain the epoxidation fluorine-containing polyarylether compound. The reaction process is as follows:
in order to better realize the invention, NMP and deionized water are calculated according to the volume ratio in the step (1), wherein the ratio is 1:2-10.
In the step (1), the molar ratio of the 2, 2-diallyl bisphenol A to the decafluorobiphenyl to the calcium hydride to the cesium fluoride is 1:8-10:0.1-0.5:3-5.
In the step (2), the molar ratio of the ABA-containing monomer to bisphenol a to calcium hydride to cesium fluoride=1:1:0.1-0.5:3-5.
In the step (2), the volume ratio of NMP to deionized water to dichloromethane to methanol=1:2-10:1-5:2-10.
In the step (3), the molar ratio of fluorine-containing polyarylether containing allyl to mCPBA=1:3-5.
In the step (3), absolute methylene dichloride and methanol=1:2-10 are calculated according to the volume ratio.
An epoxy resin cured product is obtained by curing and crosslinking the epoxy resin and the epoxidized fluorine-containing polyarylether compound.
The preparation method of the invention is a preferable scheme, and reasonable temperature, time and other reaction conditions which can be foreseen by the person skilled in the art are all within the scope of the invention and are not limited to the above reaction conditions.
Compared with the prior art, the invention has the following beneficial effects:
(1) The invention has the advantages of wide sources of raw materials, simple process, only one step of polymerization, high fluorine content of the obtained product and super-strong stability. (2) The structure of the invention contains a rigid benzene ring structure, has excellent thermal performance, and can be used in high-temperature resistant industrial environment; the epoxy resin also contains reactive epoxy groups, can participate in curing, and can be applied to the fields of resin modification, coating, composite materials and the like.
(3) The polyaryletherketone compound containing the epoxy groups can adjust the content of the epoxy groups by changing the proportion of raw materials, thereby controlling the crosslinking density, the mechanical properties and the like of a cured product; the epoxy resin condensate prepared by the invention has stronger stability, excellent mechanical property, dielectric property and the like.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of an allyl group-containing ABA type monomer of example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance fluorine spectrum of an allyl group-containing ABA type monomer of example 1 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the fluorine-containing polyarylether FPAE containing allyl groups of example 2 and the epoxidized fluorine-containing polyarylether compound EFPAE of example 3 of the present invention;
FIG. 4 is a nuclear magnetic resonance fluorine spectrum of the fluorine-containing polyarylether FPAE containing allyl groups of example 2 and the epoxidized fluorine-containing polyarylether compound EFPAE of example 3 of the present invention;
FIG. 5 is an infrared spectrum of an allyl-containing fluorine-containing polyarylether FPAE of example 2 and an epoxidized fluorine-containing polyarylether compound EFPAE of example 3 of the present invention;
FIG. 6 is a thermal weight loss curve of an allyl-containing fluorinated polyarylether FPAE of example 2 and an epoxidized fluorinated polyarylether compound EFPAE of example 3 of the present invention;
FIG. 7 is a differential scanning calorimetric curve of an allyl-containing fluorinated polyarylether FPAE of example 2 and an epoxidized fluorinated polyarylether compound EFPAE of example 3 of the present invention;
FIG. 8 is a scanning electron micrograph of an epoxy resin cured product prepared in example 4 of the present invention: (a) is an epoxy resin cured product containing no EFPAE, and (b) and (c) are epoxy resin cured products containing EFPAE.
Detailed Description
The invention is further illustrated below in connection with specific examples, but the invention is not limited to these examples only.
EXAMPLE 1 Synthesis of allyl ABA-containing monomers
Adding 0.1mol (30.842 g) of 2, 2-diallyl bisphenol A and 1mol (334.12 g) of decafluorobiphenyl into 1500mL of N-methylpyrrolidone (NMP), introducing argon, magnetically stirring at room temperature until the mixture is completely dissolved, adding 2g of calcium hydride, stirring for 5min, adding 0.3mol of cesium fluoride, reacting for 24h, slowly pouring the obtained solution into 3.0L of deionized water, separating out precipitate, filtering, vacuum drying at 80 ℃, and purifying by using a chromatographic silica gel column with petroleum ether as a mobile phase to obtain an allyl-containing solutionABA monomer with a yield of 95%. 1 H NMR 19 F NMR is shown in FIGS. 1 and 2.
EXAMPLE 2 Synthesis of allyl-containing fluorine-containing polyarylether (FPAE)
0.01mol (9.366 g) of an allyl-containing ABA type monomer and 0.01mol (2.283 g) of bisphenol A are added into 100mL of electronic grade N-methylpyrrolidone, argon is introduced, magnetic stirring is carried out at room temperature until the allyl-containing ABA type monomer and the bisphenol A are completely dissolved, 0.2g of calcium hydride is added, stirring is carried out for 5min, 0.03mol of cesium fluoride is added for reaction for 24h, the solution is slowly poured into 1L of deionized water for precipitation and filtration, the solution is poured into 100mL of dichloromethane for complete dissolution after being dried at 80 ℃ in a vacuum oven, then the solution is poured into 1L of methanol for precipitation and filtration, and drying is carried out for 24h at 80 ℃ in the vacuum oven, thus obtaining fluorine-containing polyarylether (FPAE) containing allyl, and the yield is 88%. Intrinsic viscosity: 1.8g dL -1 。 1 H NMR 19 The F NMR is shown in figures 3 and 4, 1 the peak at the 1.69ppm position in the H NMR spectrum was attributed to the proton peak on the methyl group, and 3.40,5.10,6.05ppm was attributed to the proton peak on the allyl group; 19 the two peaks at-138.15 and-152.98 ppm in the F NMR spectrum are assigned to the F atom on the-CF group. FT-IR spectrum as shown in FIG. 5, 1678cm -1 The peak at which is assigned to the stretching vibration peak of the allylic carbon-carbon double bond.
EXAMPLE 3 Synthesis of epoxidized fluorine-containing polyarylether Compound (EFPAE)
0.01mol (10.828 g) of fluorine-containing polyarylether containing allyl groups is dissolved in 100mL of anhydrous methylene dichloride, after the fluorine-containing polyarylether is completely dissolved, 0.03mol (3.451 g) of M-chloroperoxybenzoic acid (mCPBA) is added for reaction for 2h at 0 ℃, 0.1M NaOH solution is added, stirring is carried out for 1-5 min, then 5% by mass of saline water is used for extraction, a methylene dichloride phase is slowly poured into 1L of methanol to separate out a product, and the product is dried for 24h at 80 ℃ in a vacuum oven, so that the epoxidized fluorine-containing polyarylether compound (EFPAE) is obtained, and the yield is 91%. 1 H NMR 19 The F NMR is shown in figures 3 and 4, 1 peaks at 1.69ppm and 2.61,2.83,3.07 and 3.29ppm in the H NMR spectrum are ascribed to proton peaks on methyl and on epoxy of EFPAE, and peaks 6.67,6.99,7.06,7.23ppm and 7.23ppm are ascribed to EPFAE backbone benzeneProtons on the ring; 19 the two peaks at-138.15 and-152.98 ppm in the F NMR spectrum are assigned to the F atom on the-CF group. FT-IR spectrum as shown in FIG. 5, 3023cm -1 C-H stretching vibration peaks of benzene ring, 1419, 1537 and 1622cm -1 The peak belonging to the carbon-carbon stretching vibration peak on benzene ring skeleton is 1189cm -1 The peak ascribed to C-F bond is 916cm -1 The peak at which is attributed to the characteristic peak of epoxide groups. No 1678cm was found in the FT-IR spectrum of EFPAE compared to the FT-IR spectrum of FPAE -1 Characteristic peak of allylic carbon-carbon double bond at 916cm -1 The epoxy characteristic peak at the position appears, which indicates that the epoxidation is successful.
As can be seen from FIG. 6, the epoxidized fluorine-containing polyarylether compound has a significant weight loss at 350 to 400℃indicating its thermal decomposition temperature (T d ) Higher thermal stability, better thermal stability, 53 percent carbon residue rate of the fluorine-containing polyarylether FPAE containing allyl after thermal decomposition is completed, 60 percent carbon residue rate of the epoxy fluorine-containing polyarylether compound EFPAE, and T d5％ The thermal stability after epoxy functionalization was demonstrated to be very excellent at 383 ℃. Measurement of glass transition temperatures T of FPAE and EFPAE by DSC g As shown in FIG. 7, DSC curve has obvious endothermic transition at 130-170℃and T of FPAE g T of EFPAE after epoxy functionalization at 141 DEG C g Above FPAE, 162 ℃.
EXAMPLE 4 preparation of epoxy resin cured product
(1) Preparation of epoxy resin cured product containing no EFPAE
Uniformly mixing 0.256g of 4,4' -diaminodiphenylmethane curing agent and 5g of bisphenol A diglycidyl ether epoxy resin, melting at 120 ℃, pouring into a preheated mold, and placing into a vacuum oven according to 80 ℃ for 2 hours; 120 ℃ for 3h;160 ℃ for 2 hours, then cooling to room temperature, taking out the sample bar to obtain an epoxy resin cured product which does not contain EFPAE, and measuring the impact strength of the epoxy resin cured product to be 20KJ/m 2 The tensile strength was 43.8MPa, and the tensile modulus was 2.78GPa.
(2) Preparation of epoxy resin cured product containing EFPAE
Preparation of example 3 0.5gUniformly mixing the epoxy fluorine-containing polyarylether compound EFPAE, 0.256g of 4,4' -diaminodiphenylmethane curing agent and 5g of bisphenol A diglycidyl ether epoxy resin, melting at 120 ℃, pouring into a preheated mold, and placing into a vacuum oven according to the temperature of 80 ℃ for 2 hours; 120 ℃ for 3h;160 ℃ for 2 hours, then cooling to room temperature, taking out the sample bar to obtain an epoxy resin condensate containing EFPAE, and measuring the impact strength of the epoxy resin condensate to be 26KJ/m 2 The tensile strength was 100.3MPa, and the tensile modulus was 4.02GPa.
As shown in fig. 8 a, the fracture morphology of the epoxy resin cured product containing no EFPAE exhibited typical brittle fracture characteristics, the surface was ordered and smooth, while the fracture morphology of the epoxy resin cured product containing EFPAE exhibited rough and disordered morphology characteristics, and typical ductile fracture morphologies (b and c in fig. 8) of crack scattering, microcracking, etc., were present, indicating that it was possible to successfully toughen the epoxy resin.
Example 5 preparation of a coating of an allyl-containing fluorine-containing polyarylether FPAE and an epoxidized fluorine-containing polyarylether Compound EFPAE
The tinplate (120 mm multiplied by 28 mm) is polished by 400# sand paper, the scraps are washed off by clean water, then the tinplate is placed in ethanol for ultrasonic treatment for 0.5h, the tinplate is washed by deionized water and ethanol again, and the tinplate is placed in a self-sealing bag for standby after the surface liquid is thoroughly dried in an oven at 80 ℃. 0.25g of FPAE and EFPAE were dissolved in 9g of N, N-dimethylacetamide (DMAc), respectively, to give a 3wt.% polymer solution, which was poured into a spray gun to spray-coat onto the pretreated tinplate, dried in an oven at 80℃for 2h, then heated to 120℃for further drying 2h, and again heated to 160℃for drying 2h to achieve complete curing. And using a spiral micrometer to test the thickness of the polished base material, and then testing the thickness of the base material after spraying the coating, wherein the thickness difference is the thickness of the coating. The hardness of the surface of the coating is tested by using a GB/T6739-2006 pencil hardness test method; the adhesion of the coating was tested using GB/T9286-1998 cross-hatch; flexibility was tested using QTX type paint film flexibility instrument shaft bars; testing gloss using an FPU gloss meter; the contact angle of the coated surface was measured using an atlas Theta contact angle tester of Biolin Scientific.
TABLE 1 coating film Properties of allyl-containing fluorine-containing polyarylether (FPAE) and epoxidized fluorine-containing polyarylether Compound (EFPAE)
Table 1 shows that the hardness of the fluorine-containing polyarylether FPAE containing allyl groups is 6H, the toughness is 0.5mm, while the hardness of the epoxidized fluorine-containing polyarylether compound EFPAE is 6H, the flexibility is 0.6mm, which shows that the hardness of the two compounds reaches the highest grade of national standard GB6739-86, but the toughness of the EFPAE is better than that of the FPAE; secondly, the glossiness and the contact angle of the coating added with the EFPAE are both larger than those of the coating added with the FPAE, which shows that the paint film performance of the coating containing the EFPAE is better than that of the coating containing the FPAE.
The foregoing description is only of the preferred embodiments of the invention, and all changes and modifications that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (9)
1. An epoxidized fluorine-containing polyarylether compound, which is characterized by having the following structural formula:
wherein n=10 to 100.
2. A process for preparing an epoxidized fluorinated polyarylether compound according to claim 1, comprising the steps of:
(1) Adding 2, 2-diallyl bisphenol A and decafluorobiphenyl into N-methylpyrrolidone, introducing argon, magnetically stirring at room temperature until the mixture is completely dissolved, adding calcium hydride, stirring for 5-10 min, adding cesium fluoride, reacting for 24-48 h, pouring the obtained solution into deionized water, precipitating and filtering, vacuum drying at 60-80 ℃, and purifying by using a chromatographic silica gel column by using petroleum ether as a mobile phase to obtain an ABA monomer containing allyl;
(2) Adding an allyl-containing ABA monomer and bisphenol A into N-methylpyrrolidone, introducing argon, magnetically stirring at room temperature until the allyl-containing ABA monomer and bisphenol A are completely dissolved, adding calcium hydride, stirring for 5-10 min, adding cesium fluoride, reacting for 24-48 h, pouring the obtained solution into deionized water to precipitate and filter, drying in a vacuum oven at 60-80 ℃ for 12-24 h, pouring the solution into methylene chloride for complete dissolution, pouring the solution into methanol to precipitate and filter, and drying in the vacuum oven at 60-80 ℃ for 12-24 h to obtain allyl-containing fluorine-containing polyarylether;
(3) Dissolving fluorine-containing polyarylether containing allyl into anhydrous dichloromethane to prepare a solution with the mass concentration of 1-30%, reacting for 2-4 hours at the temperature of 0-10 ℃ by taking M-chloroperoxybenzoic acid as an oxidant, then adding 0.1-1M NaOH aqueous solution, stirring for 1-5 minutes, extracting by using 2-10% of saline water by mass fraction, slowly pouring a dichloromethane phase into methanol to precipitate, filtering, and drying for 12-24 hours at the temperature of 60-80 ℃ in a vacuum oven to obtain the epoxidation fluorine-containing polyarylether compound.
3. The method for producing an epoxidized fluorinated polyarylether compound according to claim 2, wherein in the step (1), N-methylpyrrolidone/deionized water=1:2 to 10 by volume ratio.
4. The method for producing an epoxidized fluorine-containing polyarylether compound according to claim 2, wherein in the step (1), the molar ratio of 2, 2-diallyl bisphenol a to decafluorobiphenyl to calcium hydride to cesium fluoride=1:8 to 10:0.1 to 0.5:3 to 5 is calculated.
5. The method for producing an epoxidized fluorinated polyarylether compound according to claim 2, wherein the molar ratio of the allyl group-containing ABA-type monomer to bisphenol a to calcium hydride to cesium fluoride=1:1:0.1 to 0.5:3 to 5 in step (2).
6. The method for producing an epoxidized fluorine-containing polyarylether compound according to claim 2, wherein in the step (2), N-methylpyrrolidone, deionized water, methylene chloride, and methanol=1:2 to 10:1 to 5:2 to 10 are used in terms of volume ratio.
7. The method for producing an epoxidized fluorinated polyarylether compound according to claim 2, wherein the molar ratio of the fluorinated polyarylether containing allyl groups to m-chloroperoxybenzoic acid=1:3 to 5 in the step (3).
8. The method for producing an epoxidized fluorinated polyarylether compound according to claim 2, wherein in the step (3), anhydrous methylene chloride and methanol=1:2-10 are used in terms of volume ratio.
9. An epoxy resin cured product obtained by curing and crosslinking the epoxidized fluorine-containing polyarylether compound according to claim 1 and an epoxy resin.
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