Bio-based aromatic polyamides based on ferulic acid-derived diacid structures and preparation methods thereof

Abstract

The present invention discloses a bio-based aromatic polyamide based on a ferulic acid-derived diacid structure and a preparation method thereof. The bio-based aromatic polyamide is prepared by polycondensing a diacid 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid derived from ferulic acid with a diamine monomer. The bio-based aromatic polyamide provided by the present invention has the advantages of simple preparation, good solvent resistance, good heat resistance, excellent mechanical properties, etc.

Description

Technical Field

[0001] The present invention relates to an aromatic polyamide material, and in particular to a bio-based aromatic polyamide based on ferulic acid-derived diacid structure and a preparation method thereof, belonging to the technical field of polymer synthetic materials. Background Art

[0002] In recent years, in order to achieve the full utilization of carbon resources, the research on biomass plastics that can replace petroleum-derived plastics has received extensive attention. Biomass plastics refer to a type of plastics synthesized from renewable biomass resources. The large-scale use of biomass to produce plastics is conducive to the full utilization of biomass waste such as agricultural and forestry waste, and at the same time reduces the consumption of petroleum resources, which is conducive to the sustainable development of society. Data shows that the average annual production capacity growth rate of bio-based polymers is 8%, significantly higher than the overall growth rate of polymers (3%-4%), and this growth is expected to continue until 2025. Among these continuously growing bio-based polymers, the growth rate of bio-based polyamides is as high as 37%. Polyamides are a type of high-performance polymer material with polar amide groups (-CO-NH-) in the main chain of the molecule. According to whether the chemical structure of polyamide contains a rigid aromatic ring, polyamides can be divided into aliphatic polyamides, semi-aromatic polyamides, and fully aromatic polyamides. Semi-aromatic polyamides and fully aromatic polyamides are collectively called aromatic polyamides. Previous research on bio-based polyamides has mostly focused on aliphatic polyamides, and there is little research on aromatic bio-based polyamides. Aromatic polyamides have better chemical stability, heat resistance, and mechanical properties than aliphatic polyamides. Bio-based aromatic polyamides have great development prospects. Ferulic acid is a phenolic acid present in sugarcane bagasse, wheat bran, and beet pulp, and can also be obtained by the depolymerization of lignin. It has the characteristics of wide source, large output, and low price. However, there are few reports on the application of ferulic acid in the synthesis of polyamides.

[0003] Synthesis of novel polyamides starting from ferulic acid dimer derivative[J].Designed Monomers and Polymers, 2004, 7(6); 711-725. discloses a method for synthesizing polyamides from ferulic acid. First, the dimer of ferulic acid is prepared by a photochemical reaction, and then the dimer diacid is converted into an acyl chloride for polycondensation with diamine. This method is the first attempt to use ferulic acid in the field of polyamide synthesis, but its preparation process is complex and not conducive to large-scale production. Summary of the Invention

[0004] The main object of the present invention is to provide a bio-based aromatic polyamide based on ferulic acid-derived diacid structure and a preparation method thereof, so as to overcome the deficiencies of the prior art.

[0005] To achieve the aforementioned invention objectives, the technical solutions adopted by the present invention include:

[0006] An embodiment of the present invention provides a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid, which is prepared by polycondensation of ferulic acid-derived diacid and diamine monomers.

[0007] Among them, the ferulic acid-derived diacid is 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid, and its chemical structural formula is shown in Formula (I):

[0008]

[0009] An embodiment of the present invention also provides a preparation method of a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid, which includes: subjecting the ferulic acid-derived diacid and diamine monomers to a polycondensation reaction to obtain a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid.

[0010] An embodiment of the present invention also provides a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid prepared by the aforementioned preparation method.

[0011] Compared with the prior art, the beneficial effects of the present invention include:

[0012] The bio-based aromatic polyamide provided by the present invention is obtained by polycondensation of the diacid 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid derived from ferulic acid and diamine monomers. The obtained polyamide has the advantages of simple preparation, good solvent resistance, good heat resistance, excellent mechanical properties, etc., and also has antibacterial properties, and can be used in the biomedical industry or other fields with high requirements for antibacterial properties. BRIEF DESCRIPTION OF THE DRAWINGS

[0013] In order to more clearly illustrate the technical solutions in the embodiments of the present application or the prior art, the following will briefly introduce the drawings required for use in the description of the embodiments or the prior art. Obviously, the drawings in the following description are only some embodiments recorded in the present application. For those of ordinary skill in the art, without creative efforts, other drawings can also be obtained based on these drawings.

[0014] Figure 1 It is the nuclear magnetic resonance hydrogen spectrum diagram of the ferulic acid-derived diacid used in Example 1 of the present invention and the polyamide synthesized from it and terephthalic acid. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0015] In view of the deficiencies of the prior art, through long-term research and a large number of practices, the inventors of this case have proposed the technical solution of the present invention. The following will clearly and completely describe the technical solution of the present invention. Obviously, the described embodiments are part of the embodiments of the present invention, rather than all embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts belong to the scope of protection of the present invention.

[0016] The main design concept of the present invention lies in that the inventors of this case polycondensed the diacid 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid derived from ferulic acid with a diamine monomer to obtain a series of unsaturated aromatic polyamide materials based on the ferulic acid-derived diacid structure with excellent comprehensive properties.

[0017] One aspect of the embodiments of the present invention provides a bio-based aromatic polyamide based on the ferulic acid-derived diacid structure, which is prepared by polycondensing the ferulic acid-derived diacid with a diamine monomer.

[0018] Among them, the ferulic acid-derived diacid used in the present invention is 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid, and its chemical structural formula is shown in Formula (I):

[0019]

[0020] In some embodiments, the diamine monomer includes any one or a combination of two or more of aromatic diamines, alicyclic diamines, aliphatic diamines, etc., but is not limited thereto.

[0021] Further, the aromatic diamine (i.e., the aromatic ring structure diamine monomer) includes any one or a combination of two or more of p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, etc., but is not limited thereto.

[0022] Further, the alicyclic diamine (i.e., the alicyclic ring structure diamine monomer) includes any one or a combination of two of isophorone diamine, 1,4-cyclohexanediamine, etc., but is not limited thereto.

[0023] Further, the aliphatic diamine (i.e., the aliphatic chain structure diamine monomer) includes any one or a combination of two or more of 1,5-diaminopentane, 1,6-diaminohexane, 1,10-diaminodecane, etc., but is not limited thereto.

[0024] Further, the glass transition temperature range of the bio-based aromatic polyamide based on the ferulic acid-derived diacid structure is between 80 and 220 °C, the tensile strength is 20 to 80 MPa, and the elongation at break is 5% to 20%.

[0025] Another aspect of the embodiments of the present invention provides a method for preparing a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid, which includes: subjecting the ferulic acid-derived diacid and a diamine monomer to a polycondensation reaction to obtain a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid.

[0026] Among them, the ferulic acid-derived diacid and the diamine monomer used in the preparation process of the present invention are as described above, and will not be elaborated here.

[0027] In some embodiments, the preparation method specifically includes: in a protective atmosphere, subjecting a mixed reaction system containing ferulic acid-derived diacid, diamine monomer, solvent, optionally added co-solvent, and condensing agent to a polycondensation reaction at 100-130 °C for 4-6 h to obtain a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid. Among them, the condensing agent is a combination of pyridine and triphenyl phosphite, and the two are used as condensing reagents to activate the carboxyl group.

[0028] In some more specific embodiments, the preparation method may include: in a protective atmosphere, first mix the ferulic acid-derived diacid with the solvent, add the optionally added co-solvent, heat to 80 °C to dissolve fully, and then add the diamine monomer, pyridine, and triphenyl phosphite, and raise the temperature to 100-130 °C for a polycondensation reaction for 4-6 h.

[0029] Further, the molar ratio of the ferulic acid-derived diacid to the diamine monomer is 1:1.

[0030] Further, the solvent includes the polar solvent N-methylpyrrolidone (NMP), but is not limited thereto. For example, it can also be replaced with polar aprotic solvents such as dimethylacetamide (DMAc).

[0031] Further, the concentration of the ferulic acid-derived diacid or the diamine monomer in the mixed reaction system is 0.3-0.5 mol / L.

[0032] Further, the content of the co-solvent in the mixed reaction system is 4 wt% - 8 wt%, and the co-solvent includes at least any one of anhydrous LiCl, anhydrous CaCl 2 etc. In other words, anhydrous LiCl or anhydrous CaCl with a solution mass fraction of 4% - 8 wt% can be added to the mixed reaction system. 2 .

[0033] Further, the volume ratio of pyridine to the solvent in the mixed reaction system is 25:100. In other words, pyridine with a solvent volume fraction of 25% can be added to the mixed reaction system.

[0034] Furthermore, the molar ratio of triphenyl phosphite to ferulic acid derived diacid or diamine monomer in the mixed reaction system is 2: 1. In other words, triphenyl phosphite can be added to the mixed reaction system at a molar ratio of 2 times that of ferulic acid derived diacid or diamine monomer.

[0035] Another aspect of the embodiments of the present invention further provides a bio-based aromatic polyamide based on a ferulic acid-derived diacid structure prepared by the aforementioned preparation method.

[0036] In summary, the unsaturated bio-based aromatic polyamide provided by the present invention has the advantages of simple preparation, good solvent resistance, good heat resistance, excellent mechanical properties, etc.

[0037] Another aspect of the embodiments of the present invention also provides the application of the aforementioned bio-based aromatic polyamide based on the ferulic acid-derived diacid structure. Since ferulic acid has low toxicity, anti-inflammatory, antiviral, antibacterial and other biological activities; the prepared polyamide has a certain effect in antibacterial properties and can be used in the biopharmaceutical industry or other fields with high requirements for antibacterial properties.

[0038] In order to facilitate the understanding of the present invention, the technical scheme of the present invention will be described in more detail and completely in conjunction with specific embodiments below, but the protection scope of the present invention is not limited to the following specific embodiments. Based on the embodiments in the present invention, all other embodiments obtained by ordinary technicians in the field without creative work belong to the protection scope of the present invention. The experimental methods in the following embodiments that do not specify specific conditions are usually carried out under conventional conditions or under conditions recommended by the manufacturer.

[0039] Example 1

[0040] The fully aromatic polyamide of this embodiment is specifically polymerized using ferulic acid-derived diacid (3-[4-(carboxymethoxy)-3-methoxyphenyl] acrylic acid) and p-phenylenediamine. The specific synthesis route is as follows: 2.52g of ferulic acid-derived diacid is added to a three-necked flask containing 20mL of polar solvent NMP under nitrogen protection, and anhydrous LiCl with a solution mass fraction of 4% is added as a cosolvent. The reaction device is heated to 80°C and stirred for half an hour to obtain a light yellow clear solution. Then 1.08g of p-phenylenediamine, 5mL of pyridine, and 5.6mL of triphenyl phosphite are added, and the temperature is raised to 130°C for reaction for 6 hours. After the reaction is completed, the polymer solution is poured into methanol for separation, and the polymer solid is washed with methanol 2 to 3 times, and then washed with deionized water 2 to 3 times. The polymer is dried in a 60°C oven to finally obtain 3.32g of biomass ferulic acid-based polyamide, and the corresponding structure is characterized by nuclear magnetic resonance hydrogen spectrum, which can be referred to Figure 1 As shown, the obtained polyamide has good thermodynamic properties, a glass transition temperature of 220°C, an elongation at break of 15%, and a tensile strength of 65.7 MPa.

[0041] Example 2

[0042] The wholly aromatic polyamide of this example is specifically synthesized by polymerizing ferulic acid-derived diacid (3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid) with p-phenylenediamine. The specific synthesis route is as follows: Under the protection of nitrogen, 2.52 g of ferulic acid-derived diacid is added to a three-necked flask containing 20 mL of polar solvent DMAc, and anhydrous LiCl with a solution mass fraction of 4% is added as a co-solvent. The reaction device is heated to 80 °C and stirred for half an hour to obtain a light yellow clear solution. Then, 1.08 g of p-phenylenediamine, 5 mL of pyridine, and 5.6 mL of triphenyl phosphite are added, and the temperature is raised to 130 °C and reacted for 6 hours. After the reaction is completed, the polymer solution is poured into methanol for separation, and the polymer solid is washed with methanol 2-3 times, and then washed with deionized water 2-3 times. The polymer is dried in an oven at 60 °C, and finally 3.18 g of biomass ferulic acid-based polyamide is obtained. The glass transition temperature of the obtained polyamide is 217 °C, the elongation at break is 8%, and the tensile strength is 54.9 MPa.

[0043] Example 3

[0044] The wholly aromatic polyamide of this example is specifically synthesized by polymerizing ferulic acid-derived diacid (3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid) with p-phenylenediamine. The specific synthesis route is as follows: Under the protection of nitrogen, 2.52 g of ferulic acid-derived diacid is added to a three-necked flask containing 20 mL of polar solvent NMP, and anhydrous LiCl with a solution mass fraction of 4% is added as a co-solvent. The reaction device is heated to 80 °C and stirred for half an hour to obtain a light yellow clear solution. Then, 1.08 g of p-phenylenediamine, 5 mL of pyridine, and 5.6 mL of triphenyl phosphite are added, and the temperature is raised to 130 °C and reacted for 4 hours. After the reaction is completed, the polymer solution is poured into methanol for separation, and the polymer solid is washed with methanol 2-3 times, and then washed with deionized water 2-3 times. The polymer is dried in an oven at 60 °C, and finally 3.01 g of biomass ferulic acid-based polyamide is obtained. The glass transition temperature of the obtained polyamide is 217 °C, the elongation at break is 6%, and the tensile strength is 45.1 MPa.

[0045] Example 4

[0046] The wholly aromatic polyamide of this example is specifically prepared by polymerizing ferulic acid-derived diacid (3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid) with p-phenylenediamine. The specific synthesis route is as follows: Under the protection of nitrogen, 2.52 g of ferulic acid-derived diacid is added to a three-necked flask containing 20 mL of polar solvent NMP, and anhydrous LiCl with a solution mass fraction of 4% is added as a co-solvent. The reaction device is heated to 80 °C and stirred for half an hour to obtain a light yellow clear solution. Then, 1.08 g of p-phenylenediamine, 5 mL of pyridine, and 5.6 mL of triphenyl phosphite are added, and the temperature is raised to 100 °C and reacted for 6 hours. After the reaction is completed, the polymer solution is poured into methanol for separation, and the polymer solid is washed with methanol 2-3 times, and then washed with deionized water 2-3 times. The polymer is dried in an oven at 60 °C, and finally 3.11 g of biomass ferulic acid-based polyamide is obtained. The glass transition temperature of the obtained polyamide is 217 °C, the elongation at break is 10%, and the tensile strength is 52.4 MPa.

[0047] Example 5

[0048] The wholly aromatic polyamide of this example is specifically prepared by polymerizing ferulic acid-derived diacid (3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid) with p-phenylenediamine. The specific synthesis route is as follows: Under the protection of nitrogen, 2.52 g of ferulic acid-derived diacid is added to a three-necked flask containing 20 mL of polar solvent NMP, and anhydrous LiCl with a solution mass fraction of 4% is added as a co-solvent. The reaction device is heated to 80 °C and stirred for half an hour to obtain a light yellow clear solution. Then, 1.08 g of p-phenylenediamine, 5 mL of pyridine, and 5.6 mL of triphenyl phosphite are added, and the temperature is raised to 115 °C and reacted for 6 hours. After the reaction is completed, the polymer solution is poured into methanol for separation, and the polymer solid is washed with methanol 2-3 times, and then washed with deionized water 2-3 times. The polymer is dried in an oven at 60 °C, and finally 3.22 g of biomass ferulic acid-based polyamide is obtained. The glass transition temperature of the obtained polyamide is 218 °C, the elongation at break is 14%, and the tensile strength is 60.4 MPa.

[0049] Example 6

[0050] The component ratio and preparation method of the wholly aromatic polyamide in this example are basically the same as those in Example 1, except that: the diamine monomer in this example is 4,4'-diaminodiphenyl ether, and the added mass of the diamine monomer is 2.00 g. The glass transition temperature of the obtained polyamide material is 180 °C, the elongation at break is 15%, and the tensile strength is 42.9 MPa.

[0051] Example 7

[0052] The semi-aromatic polyamide of this example is specifically prepared by polymerizing ferulic acid-derived diacid (3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid) with isophorone diamine. The specific synthesis route is as follows: Under the protection of nitrogen, 2.52 g of ferulic acid-derived diacid is added to a three-necked flask containing 20 mL of polar solvent NMP, and anhydrous CaCl 2 is added as a co-solvent. The reaction device is heated to 80 °C and stirred for half an hour to obtain a light yellow clear solution. Then, 1.70 g of isophorone diamine, 5 mL of pyridine, and 5.6 mL of triphenyl phosphite are added, and the temperature is raised to 130 °C for reaction for 6 hours. After the reaction is completed, the polymer solution is poured into acetone for separation, and the polymer solid is washed with acetone 2-3 times and then washed with deionized water 2-3 times. The polymer is dried in an oven at 60 °C, and finally 3.61 g of biomass ferulic acid-based polyamide is obtained. The glass transition temperature of the obtained polyamide material is 162 °C, the elongation at break is 8%, and the tensile strength is 48.3 MPa.

[0053] Example 8

[0054] This example is a semi-aromatic polyamide, specifically prepared by polymerizing ferulic acid-derived diacid with 1,4-cyclohexanediamine. The component ratio is basically the same as that in Example 6, except that the mass of 1,4-cyclohexanediamine added is 1.14 g. The glass transition temperature of the obtained polyamide material is 173 °C, the elongation at break is 6%, and the tensile strength is 55.6 MPa.

[0055] Example 9

[0056] This example is a semi-aromatic polyamide, specifically prepared by polymerizing ferulic acid-derived diacid with 1,5-diaminopentane. The component ratio is basically the same as that in Example 6, except that the mass of the diamine monomer added is 1.02 g. After the reaction is completed, the polymer solution is poured into 1,4-dioxane for separation and washed with 1,4-dioxane. The glass transition temperature of the obtained polyamide material is 110 °C, the elongation at break is 10%, and the tensile strength is 34.4 MPa.

[0057] Example 10

[0058] This example is a semi-aromatic polyamide, specifically prepared by polymerizing ferulic acid-derived diacid with 1,10-diaminodecane. The component ratio is basically the same as that in Example 6, except that the mass of the diamine monomer added is 1.72 g. After the reaction is completed, the polymer solution is poured into 1,4-dioxane for separation and washed with 1,4-dioxane. The glass transition temperature of the obtained polyamide material is 85 °C, the elongation at break is 19%, and the tensile strength is 23.8 MPa.

[0059] Referring to QB / T 2591-2003A "Test Methods for Antibacterial Properties and Antibacterial Effects of Antibacterial Plastics", Escherichia coli ATCC 25922 was used to detect the antibacterial properties of the ferulic acid polyamide synthesized in the above examples. The results showed that the antibacterial rates of all examples could reach over 98% within the test time range of 24 h and 48 h, indicating that this type of polyamide has strong antibacterial effects.

[0060] Comparative Example 1

[0061] Compared with Example 1, the difference in this comparative example is that terephthalic acid and p-phenylenediamine, which are petroleum-based raw materials, were used for polymerization. The glass transition temperature of the obtained polyamide material is 250 °C, the tensile strength is 90 MPa, and the elongation at break is 5%.

[0062] Comparative Example 2

[0063] Compared with Example 8, the difference in this comparative example is that the diacid used is terephthalic acid. The glass transition temperature of the obtained polyamide material is 100 °C, the tensile strength is 70 MPa, and the elongation at break is 5%.

[0064] In addition, the inventor of this case also made tests with other raw materials, process operations, and process conditions described in this specification by referring to the foregoing examples. For example, the diamine monomers in Examples 1-10 were replaced with m-phenylenediamine, 4,4-diaminodiphenylmethane, 4,4-diaminodiphenylsulfone, 1,6-diaminohexane, etc., and relatively ideal results were obtained.

[0065] Although the present invention has been described with reference to the illustrative embodiments, those skilled in the art will understand that various other changes, omissions, and / or additions can be made without departing from the spirit and scope of the present invention, and the elements of the embodiments can be replaced with substantial equivalents. In addition, many modifications can be made without departing from the scope of the present invention to adapt a particular situation or material to the teachings of the present invention. Therefore, it is not intended to limit the present invention to the specific embodiments disclosed for carrying out the present invention, but it is intended that the present invention will include all embodiments falling within the scope of the appended claims.

Claims

1. A bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid, characterized in that, the bio-based aromatic polyamide is prepared by polycondensation of ferulic acid-derived diacid and diamine monomers; the ferulic acid-derived diacid is 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid, and its chemical structural formula is shown in Formula (Ⅰ):

2. The bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid according to claim 1, characterized in that: the diamine monomers include any one or a combination of two or more of aromatic diamines, alicyclic diamines, and aliphatic diamines.

3. The bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid according to claim 2, characterized in that: the aromatic diamines include any one or a combination of two or more of p-phenylenediamine, m-phenylenediamine, 4,4-diaminodiphenyl ether, 4,4-diaminodiphenylmethane, and 4,4-diaminodiphenyl sulfone.

4. The bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid according to claim 2, characterized in that: the alicyclic diamines include any one or a combination of two of isophorone diamine and 1,4-cyclohexanediamine.

5. The bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid according to claim 2, characterized in that: the aliphatic diamines include any one or a combination of two or more of 1,5-diaminopentane, 1,6-diaminohexane, and 1,10-diaminodecane.

6. The bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid according to claim 2, characterized in that: the glass transition temperature of the bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid is 80-220 °C, the tensile strength is 20-80 MPa, and the elongation at break is 5%-20%.

7. A preparation method of a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid, characterized in that, it includes: subjecting ferulic acid-derived diacid and diamine monomers to a polycondensation reaction to obtain a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid; the ferulic acid-derived diacid is 3-[4-(carboxymethoxy)-3-methoxyphenyl]acrylic acid, and its chemical structural formula is shown in Formula (Ⅰ):

8. The preparation method according to claim 7, characterized in that, specifically includes: in a protective atmosphere, subjecting a mixed reaction system containing ferulic acid-derived diacid, diamine monomers, a solvent, a selectively added co-solvent, and a condensing agent to a polycondensation reaction at 100-130 °C for 4-6 h to obtain a bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid, and the condensing agent includes pyridine and triphenyl phosphite.

9. The preparation method according to claim 8, characterized in that: the diamine monomers include any one or a combination of two or more of aromatic diamines, alicyclic diamines, and aliphatic diamines.

10. The preparation method according to claim 9, characterized in that: The aromatic diamine includes any one or a combination of two or more of p-phenylenediamine, m-phenylenediamine, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, and 4,4'-diaminodiphenyl sulfone.

11. The preparation method according to claim 9, characterized in that: The alicyclic diamine includes any one or a combination of two of isophorone diamine and 1,4-cyclohexanediamine.

12. The preparation method according to claim 9, characterized in that: The aliphatic diamine includes any one or a combination of two or more of 1,5-diaminopentane, 1,6-diaminohexane, and 1,10-diaminodecane.

13. The preparation method according to claim 8, characterized in that: The molar ratio of the ferulic acid-derived diacid to the diamine monomer is 1:

1.

14. The preparation method according to claim 8, characterized in that: The solvent includes any one of N-methylpyrrolidone and dimethylacetamide.

15. The preparation method according to claim 8, characterized in that: The concentration of the ferulic acid-derived diacid or the diamine monomer in the mixed reaction system is 0.3 - 0.5 mol / L.

16. The preparation method according to claim 8, characterized in that: The content of the co-solvent in the mixed reaction system is 4 wt% to 8 wt%, and the co-solvent includes anhydrous LiCl and / or anhydrous CaCl 2 .

17. The preparation method according to claim 8, characterized in that: The volume ratio of pyridine to the solvent in the mixed reaction system is 25:

100.

18. The preparation method according to claim 8, characterized in that: The molar ratio of triphenyl phosphite to the ferulic acid-derived diacid or the diamine monomer in the mixed reaction system is 0.6 - 1.0 mol / L.

19. A bio-based aromatic polyamide based on the structure of ferulic acid-derived diacid prepared by the preparation method according to any one of claims 7 - 18.

Images