Thermosetting resin with low dielectric constant and low dielectric loss factor, and preparation method and application thereof
Thermosetting resins with low dielectric constants and dielectric loss factors are prepared by polymerization reactions of amino monomers, aldehyde monomers, and active methylene compounds. This solves the problem of high dielectric properties in traditional resins, meets the requirements of high-frequency signal transmission, and is suitable for fields such as 5G/6G communication.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- JIANGNAN UNIV
- Filing Date
- 2026-02-27
- Publication Date
- 2026-05-01
AI Technical Summary
Traditional thermosetting resins have high dielectric constants and dielectric loss factors in alternating electric fields, which affects the transmission rate and intensity of high-frequency signals and limits their application in the field of high-frequency communication.
Thermosetting resins with low dielectric constant and low dielectric loss factor are prepared by polymerization of amino monomers, aldehyde monomers and compounds containing active methylene groups. The reaction is carried out in a solvent, and the reaction temperature and time are controlled within a certain range.
The prepared thermosetting resin has low dielectric constant and dielectric loss in the high-frequency X-band, which meets the requirements of high-frequency signal transmission and is suitable for 5G/6G communication and other fields.
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Figure CN121949718A_ABST
Abstract
Description
Low dielectric constant, low dielectric loss factor thermosetting resins, preparation methods and applications Technical Field
[0001] This invention relates to the field of thermosetting resin materials technology, and more specifically, to a thermosetting resin with low dielectric constant and low dielectric loss factor, its preparation method, and its application in high-frequency communication and other fields. Background Technology
[0002] Thermosetting resins are a class of high-performance polymers, renowned for their excellent mechanical strength, thermal stability, chemical resistance, and dielectric properties. They are widely used in aerospace, high-performance coatings, automotive, and microelectronics industries. However, most traditional thermosetting resins, such as commercially available epoxy and phenolic resins, contain a large number of polar hydroxyl groups, which form a macroscopic dipole moment in an alternating electric field, resulting in high dielectric constants and dielectric loss factors. When used in communications, these resins can reduce signal strength, especially at high frequencies (300MHz). Therefore, there is a need to develop thermosetting resins with low dielectric constants and low dielectric loss factors to minimize their impact on signal transmission rates and strength.
[0003] Currently, there is increasing research on thermosetting resins with low dielectric constants and low dielectric loss factors. Shang Lei et al. prepared a silicon-containing epoxy resin using vanillin as a raw material (J. Ind. Eng. Chem. 2024, 137, 480–490), which exhibited a dielectric constant between 0.75 and 0.95 and a dielectric loss of approximately 0.012 in the 1Hz-1MHz range. Zhang Chaoqun et al. synthesized epoxy monomers using 5',5-diallyl-22'-biphenyl hydroquinone as a raw material, blended them with epoxy castor oil in a certain proportion, and crosslinked them with ester compounds to form an epoxy resin. This resin showed a dielectric constant of 3.19 and a dielectric loss of 0.12 in the 100MHz range (Ind. Crops Prod. 2024. 220, 119117). However, the dielectric loss of these epoxy resins remains relatively high, failing to meet the requirements of high-frequency signal transmission and limiting their widespread application. Therefore, we synthesized a series of thermosetting resins with low dielectric constants and dielectric losses using amino monomers, aldehyde monomers, and other raw materials. These resins exhibit a dielectric constant of 2.93 and a dielectric loss factor of 0.009 at 10 GHz. Their dielectric constant and dielectric loss factor meet the requirements for high-frequency signal transmission, providing a research approach for preparing thermosetting resins with low dielectric constants and dielectric loss factors suitable for applications such as 6G communications, and offering a new direction for designing such resins. Summary of the Invention
[0004] To address the problems existing in the prior art, this invention provides a thermosetting resin with low dielectric constant and low dielectric loss factor, a preparation method, and applications. The prepared thermosetting resin will solve the above-mentioned problems.
[0005] The technical solution of the present invention:
[0006] A thermosetting resin with low dielectric constant and low dielectric loss factor, wherein the thermosetting resin is formed by polymerization of amino monomers, aldehyde monomers, and a compound containing an active methylene group; wherein the general structural formula of the thermosetting resin is:
[0007]
[0008] Wherein, R group is one of nitrogen, phosphorus, and carbon; R1 group is one of methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, and biphenyl ether group; R2 group is one of hydrogen, methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, and biphenyl ether group; R3 group is one of methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, biphenyl ether group, and biphenyl silyl group; and R4 group is one of methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, biphenyl ether group, and biphenyl silyl group.
[0009] Furthermore, the aldehyde monomer has a difunctional aldehyde structure.
[0010] Furthermore, the low dielectric constant and low dielectric loss factor thermosetting resin is prepared by reacting the following components (by weight): amino monomer, aldehyde monomer, and a compound containing an active methylene group in a solvent via a Schiff base and a Knovengel reaction:
[0011] The mixture comprises 1-50 parts amino monomer, 20-100 parts solvent, 1-50 parts aldehyde monomer, and 10-120 parts containing an active methylene compound. Preferably, it comprises 1-30 parts amino monomer, 20-50 parts solvent, 1-30 parts aldehyde monomer, and 10-60 parts containing an active methylene compound.
[0012] Further, the solvent is at least one selected from dimethyl sulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, ethanol, methanol, tetrahydrofuran, acetonitrile, dichloromethane, and propanol; preferably at least one selected from methanol, ethanol, tetrahydrofuran, and dichloromethane; the aldehyde monomer is at least one selected from terephthalaldehyde, glutaraldehyde, glyoxal, o-phthalaldehyde, 4,4'-siliminobisbenzaldehyde, and 4-[(4-formylphenyl)dimethylsilyl]benzaldehyde; the amino monomer is at least one selected from tris(2-aminoethyl)amine and tris(2-aminophenyl)amine. The compound containing at least one of the following: 3-(2-aminoethyl)phosphine, tris(2-aminophenyl)phosphine, 3-(2-aminoethyl)-1,5-pentanediamine, and 3,3-bis(2-aminoethyl)-1,5-pentanediamine, wherein the active methylene compound is one of ethyl acetoacetate, methyl acetoacetate, propyl acetoacetate, butyl propyl acetoacetate, acetoacetaldehyde, acetylacetone, hexafluoroacetylacetone, dibenzoylmethane, 1,3-di(cyclohexyl)propanedione, 1-phenylbutane-1,3-dione, and methyl 3-oxo-3-phenylpropionate.
[0013] A method for preparing a thermosetting resin with low dielectric constant and low dielectric loss factor includes:
[0014] Aldehyde monomers and compounds containing active methylene groups are dissolved in a solvent and reacted. Then, amino monomers are added and reacted. The mixture is stirred and poured into a mold to obtain a thermosetting resin with low dielectric constant and low dielectric loss factor.
[0015] Furthermore, the temperature of the first two reactions is 20℃-100℃, and the reaction time is 1-12h; the temperature of the third reaction is 50-180℃, and the reaction time is 1-12h.
[0016] An application of a thermosetting resin with low dielectric constant and low dielectric loss factor is disclosed, which is used in 5G / 6G communications, integrated circuits, copper clad laminates, mobile terminals, Internet base stations, servers, aerospace, and mobile phone base stations.
[0017] The beneficial effects of this invention are as follows: The method for preparing thermosetting resins with low dielectric constant and low dielectric loss factor can be implemented on traditional, simple synthesis equipment, resulting in low cost and ease of industrial production. By analyzing the relationship between dielectric constant and dielectric loss factor and frequency, it can be found that the thermosetting resin prepared by this invention exhibits low dielectric constant and dielectric loss in the high-frequency X-band (8.2 GHz - 12.4 GHz), meeting the requirements for high-frequency signal transmission. The thermosetting resin prepared by this invention has broad application prospects in fields such as 6G communication. Attached Figure Description
[0018] Figure 1 shows the relationship between the dielectric loss factor of the thermosetting resin and the frequency in Example 1.
[0019] Figure 2 shows the relationship between the dielectric constant of the thermosetting resin and the frequency in Example 1.
[0020] Figure 3 shows the infrared spectrum of the thermosetting resin in Example 1. Detailed Implementation
[0021] The present invention will be further described below with reference to the embodiments.
[0022] Test method description:
[0023] 1. The relationship between dielectric constant and dielectric loss and frequency is used to prove that thermosetting resin can meet the requirements for high-frequency signal transmission.
[0024] 2. The infrared spectrum of the thermosetting resin proves that the thermosetting resin has been successfully synthesized.
[0025] I. Unless otherwise specified, all reagents in the implementation plan are manufactured by Adamas Corporation.
[0026] Example 1
[0027] 10 parts of terephthalaldehyde, 30 parts of ethyl acetoacetate, and 100 parts of acetonitrile were reacted at 50°C for 6 hours. Then, 10 parts of tris(2-aminoethyl)amine were added, and the mixture was reacted at 50°C for 6 hours. The mixture was then stirred, poured into a mold, and reacted at 80°C for 3 hours to obtain thermosetting resin 1.
[0028]
[0029] The obtained samples were characterized using a dielectric constant meter, and the characterization results are shown in Figures 1 and 2.
[0030] Example 2
[0031] 10 parts of terephthalaldehyde, 30 parts of methyl acetoacetate, and 100 parts of methanol were reacted at 60°C for 6 hours. Then, 30 parts of tris(2-aminoethyl)phosphine were added, and the mixture was reacted at 60°C for 8 hours. The mixture was then stirred, poured into a mold, and reacted at 80°C for 5 hours to obtain thermosetting resin 2.
[0032]
[0033] Example 3
[0034] 10 parts of terephthalaldehyde, 30 parts of acetylacetone, and 100 parts of ethanol were reacted at 70°C for 6 hours. Then, 40 parts of tris(2-aminoethyl)amine were added, and the mixture was reacted at 50°C for 8 hours. The mixture was then stirred, poured into a mold, and reacted at 60°C for 4 hours to obtain thermosetting resin 3.
[0035]
[0036] Example 4
[0037] 10 parts of terephthalaldehyde, 30 parts of acetylacetaldehyde, and 100 parts of ethanol were reacted at 70°C for 6 hours. Then, 30 parts of tris(2-aminoethyl)phosphine were added, and the mixture was reacted at 70°C for 8 hours. The mixture was then stirred, poured into a mold, and reacted at 80°C for 6 hours to obtain thermosetting resin 4.
[0038]
[0039] Example 5
[0040] 10 parts of terephthalaldehyde, 30 parts of ethyl acetoacetate, and 100 parts of ethanol were reacted at 70°C for 6 hours. Then, 20 parts of tris(2-aminoethyl)phosphorus were added, and the mixture was reacted at 70°C for 8 hours. The mixture was then stirred, poured into a mold, and reacted at 80°C for 6 hours to obtain thermosetting resin 5.
[0041]
Claims
1. A thermosetting resin with low dielectric constant and low dielectric loss factor, characterized in that: The thermosetting resin is formed by polymerization of amino monomers, aldehyde monomers, and compounds containing active methylene groups; wherein, the general structural formula of the thermosetting resin is: Wherein, R group is one of nitrogen, phosphorus, and carbon; R1 group is one of methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, and biphenyl ether group; R2 group is one of hydrogen, methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, and biphenyl ether group; R3 group is one of methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, biphenyl ether group, and biphenyl silyl group; and R4 group is one of methylene, ethyl, propyl, butyl, phenyl, 4-fluorophenyl, biphenyl ether group, and biphenyl silyl group.
2. The thermosetting resin with low dielectric constant and low dielectric loss factor as described in claim 1, characterized in that: The aldehyde monomer has a difunctional aldehyde structure.
3. The thermosetting resin with low dielectric constant and low dielectric loss factor as described in claim 1, characterized in that, The low dielectric constant and low dielectric loss factor thermosetting resin is prepared by reacting the following components by weight in a solvent: amino monomer, aldehyde monomer, and active methylene compound, in a Schiff base and Knovengel reaction: 1-50 parts amino monomer, 20-100 parts solvent, 1-50 parts aldehyde monomer, and 10-120 parts active methylene compound.
4. The thermosetting resin with low dielectric constant and low dielectric loss factor as described in claim 3, characterized in that, The solvent is at least one of dimethyl sulfoxide, N,N-dimethylacetamide, N,N-dimethylformamide, ethanol, methanol, tetrahydrofuran, acetonitrile, dichloromethane, and propanol.
5. The thermosetting resin with low dielectric constant and low dielectric loss factor as described in claim 3, characterized in that, The aldehyde monomer is at least one of terephthalaldehyde, glutaraldehyde, glyoxal, o-phthalaldehyde, 4,4'-siliminobisbenzaldehyde, and 4-[(4-formylphenyl)dimethylsilyl]benzaldehyde.
6. The thermosetting resin with low dielectric constant and low dielectric loss factor as described in claim 3, characterized in that, The amino monomer is at least one of tris(2-aminoethyl)amine, tris(2-aminophenyl)amine, tris(2-aminophenyl)phosphine, tris(2-aminoethyl)phosphine, 3-(2-aminoethyl)-1,5-pentanediamine, and 3,3-bis(2-aminoethyl)-1,5-pentanediamine.
7. The thermosetting resin with low dielectric constant and low dielectric loss factor as described in claim 3, characterized in that, The active methylene compound is one of ethyl acetoacetate, methyl acetoacetate, propyl acetoacetate, butyl propyl acetoacetate, acetoacetaldehyde, acetylacetone, hexafluoroacetylacetone, dibenzoylmethane, 1,3-di(cyclohexyl)propanedione, 1-phenylbutane-1,3-dione, and methyl 3-oxo-3-phenylpropionate.
8. A method for preparing a thermosetting resin with low dielectric constant and low dielectric loss factor as described in any one of claims 1-7, characterized in that, include: Aldehyde monomers and compounds containing active methylene groups are dissolved in a solvent and reacted. Then, amino monomers are added and reacted. The mixture is stirred and poured into a mold to obtain a thermosetting resin with low dielectric constant and low dielectric loss factor.
9. The preparation method according to claim 5, characterized in that, The first two reactions are carried out at temperatures of 20℃-100℃ for 1-12 hours; the third reaction is carried out at temperatures of 50-180℃ for 1-12 hours.
10. The application of a thermosetting resin with low dielectric constant and low dielectric loss factor as described in any one of claims 1-7, characterized in that, It is used in 5G / 6G communications, integrated circuits, copper-clad laminates, mobile terminals, internet base stations, servers, aerospace, and mobile phone base stations.