CN114702667B - Low-dielectric cyanate resin based on intermolecular action and preparation method thereof - Google Patents

Low-dielectric cyanate resin based on intermolecular action and preparation method thereof Download PDF

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CN114702667B
CN114702667B CN202210398265.6A CN202210398265A CN114702667B CN 114702667 B CN114702667 B CN 114702667B CN 202210398265 A CN202210398265 A CN 202210398265A CN 114702667 B CN114702667 B CN 114702667B
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cyanate
fluorine
monomer
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CN114702667A (en
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楚合涛
陈瀚
邓龙江
张林博
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University of Electronic Science and Technology of China
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/0644—Poly(1,3,5)triazines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P20/10—Process efficiency

Abstract

The invention relates to the technical field of resin matrixes, in particular to a low dielectric cyanate resin based on intermolecular interaction and a preparation method thereof. The cyanate resin of the invention changes polymer molecular network by random copolymerization of a plurality of fluorine-containing monomers and cyanate monomers, and establishes a measure of hydrogen bond action between triazine ring nitrogen atoms and nitrogen atoms introduced in the molecular network, thereby realizing improvement of mechanical property, thermal property and dielectric property of the cyanate resin by the hydrogen bond action. Wherein the long aliphatic chain structure in the fluorine-containing epoxy monomer improves the mechanical property and the thermal stability of the resin; the fluorine-containing monomer has a C-F bond structure which is symmetrically distributed, so that the molecular polarizability is reduced, and the dielectric property is favorably regulated and controlled. The fluorine-containing amino monomer introduces amino nitrogen atoms, and the amino nitrogen atoms and nitrogen atoms in a triazine ring structure formed after cyanate ester is cured form intermolecular hydrogen bonding, so that molecular polarization is further restrained, and dielectric properties are improved.

Description

Low-dielectric cyanate resin based on intermolecular action and preparation method thereof
Technical Field
The invention relates to the technical field of resin matrixes, in particular to a low dielectric cyanate resin based on intermolecular interaction and a preparation method thereof.
Background
Cyanate ester resin is a kind of resin containing cyanate ester group (-OCN) in monomer molecule, and the cyanate ester group can form symmetrical triazine ring structure under the action of heat or catalyst. The highly symmetrical triazine ring structure enables the cyanate resin to have a low dielectric constant (< 3), good thermal stability and dimensional stability, and plays an important role in the fields of electronics, aviation and aerospace. Particularly, the resin has good and stable dielectric constant and dielectric loss in a wide frequency and temperature range, and is suitable for the resin matrix of the wave-transmitting layer on the surface of the structural wave-absorbing material.
The common cyanate ester resin has high curing temperature, long curing time, high crosslinking density and brittle cured product, so that the dielectric constant is difficult to further reduce when the toughened cyanate ester resin is applied to a structural material. Common dielectric property regulation and control means such as a method of adding hollow microspheres to introduce air gaps adopted in Chinese patent CN101429337A can reduce dielectric constant, but on the other hand, mechanical properties of a resin matrix are reduced due to defects, and mechanical property requirements of structural materials are difficult to meet. In the chinese patent CN112608596a, a foaming agent is introduced into a cyanate ester prepolymer to obtain a micro-foamed low dielectric cyanate ester resin, but the mechanical properties and thermal properties of the resin are seriously deteriorated, and the resin is also difficult to be applied to engineering as a structural material.
At present, most methods for reducing the dielectric constant of the cyanate ester resin are based on the ideas of adding hollow or microporous substances, introducing low-polarity groups into polymer molecular chains, increasing the free volume of the molecular chains and the like, and are difficult to further reduce the dielectric constant and lack of diversified regulation and control means of dielectric properties.
Disclosure of Invention
Aiming at the problems or the defects, the invention provides the low dielectric cyanate resin based on the intermolecular action and the preparation method thereof, aiming at solving the problems that the application of the cyanate resin is limited due to the reduction of the mechanical property when the dielectric constant is reduced and the dielectric property regulation mechanism is single in the prior cyanate resin. The formation of hydrogen bonds between polymer molecules is schematically shown in FIG. 1.
A low dielectric cyanate resin based on intermolecular action comprises the following components in parts by weight: comprises 100 parts of cyanate ester monomer, 1-50 parts of fluorine-containing epoxy monomer, 1-50 parts of fluorine-containing amino monomer and 0-5 parts of curing catalyst.
The cyanate monomer is liquid or solid at room temperature, and the molecular structure of the cyanate monomer is one or a mixture of more of bisphenol A cyanate, tetramethyl bisphenol F cyanate, bisphenol E cyanate, bisphenol M cyanate, dicyclopentadiene bisphenol cyanate, phenolic cyanate or 4,4' -bis (trifluoromethyl) methylene diphenyl cyanate.
The fluorine-containing epoxy monomer is one or a mixture of more of 3- (perfluoro-n-octyl) -1,2-propylene oxide, 3- (perfluoro-n-hexyl) propylene oxide, 1,4-bis (2 ',3' -epoxypropyl) perfluorobutane, 1,5-bis (2,3-epoxypropoxy) -2,2,3,3,4,4-hexafluoropentane, 3- (1H, 5H octafluoropentyloxy) -1,2-propylene oxide or 3- (2,2,3,3-tetrafluoropropoxy) -1,2-propylene oxide.
The fluorine-containing amino monomer is one or a mixture of more of 2,2-difluoroethylamine, trifluoroethylamine, pentafluoroethylamine, 1,1,2,2,3,3,3-heptafluoropropane-1-amine, 2,3,5,6-tetrafluoro-1,4-phenylenediamine, 2,4,6-trifluoroaniline, 3,5-difluoroaniline, 2,6-difluoroaniline or 4,4' -diaminooctafluorobiphenyl.
The curing catalyst is an organic tin catalyst and/or a transition metal organic compound catalyst. The organic tin catalyst is stannous octoate, di-n-butyl tin oxide, di-n-octyl tin oxide and/or dibutyltin dilaurate; the transition metal organic compound catalyst is ferric acetylacetonate, cobalt naphthenate and/or imidazole catalyst.
Furthermore, if the fluorine-containing amino monomer has an aromatic ring structure, the content of the aromatic ring structure directly affects the mechanical properties of the resin system, the aromatic ring structure restricts the rotation of the chain segment, so that the rigidity of the chain segment is increased, and the toughness is deteriorated due to an excessive aromatic ring structure. Therefore, the fluorine-containing amino monomer is selected as a material having an aromatic ring structure, and the content ratio thereof is adjusted to increase the rigidity of the low dielectric cyanate ester resin based on intermolecular action. Or the fluorine-containing amino monomer does not select a material with an aromatic ring structure so as to increase the toughness of the low dielectric cyanate resin based on intermolecular action.
Furthermore, the fluorine-containing amino monomer is prepared by selecting monomers with different amino group functionalities and adjusting the content ratio of the monomers to reduce the dielectric constant of the low dielectric cyanate resin based on intermolecular interaction.
A preparation method of a low dielectric cyanate resin based on intermolecular interaction comprises the following steps:
step 1, weighing 100 parts of cyanate ester monomer, 1-50 parts of fluorine-containing epoxy monomer, 1-50 parts of fluorine-containing amino monomer and 0-5 parts of curing catalyst according to parts by weight.
Step 2, dissolving and uniformly mixing the cyanate ester monomer, the fluorine-containing epoxy monomer and the fluorine-containing amino monomer weighed in the step 1 under the condition of water bath or oil bath at the temperature of 70-90 ℃ to obtain a clear and transparent mixture without insoluble substances; then, carrying out thermal-insulation prepolymerization reaction for 0-3 h at the temperature of 70-90 ℃ to obtain a mixture a.
And 3, adding the curing catalyst prepared in the step 1 into the mixture a obtained in the step 2, and uniformly mixing to obtain a mixture b. When the curing catalyst is 0 part, this step is not carried out, but the subsequent curing process is delayed.
And 4, curing the mixture b at 130-220 ℃ to obtain the low dielectric cyanate resin based on intermolecular action.
Further, the step 4 is carried out in a polytetrafluoroethylene mold preheated at 80-100 ℃ so as to ensure that the curing effect is better.
Further, the step 4 of curing includes vacuumizing at 80-100 ℃ to remove air bubbles in the mixture b, so that the curing effect is better.
Furthermore, the curing temperature in the step 4 is increased by at least 2 times at 130-220 ℃, and the curing temperature is respectively maintained for at least 1h for curing, so that the final cured product has better uniformity.
Compared with the prior art, the invention has the following advantages:
(1) The long aliphatic chain structure in the fluorine-containing epoxy monomer is introduced, so that the flexibility of a polymer molecular chain is increased, the crosslinking density in the polymer network is reduced, and the mechanical property and the thermal stability of the resin are improved or maintained from the aspect of the motion characteristic of the polymer molecular chain.
(2) Because the introduced multiple fluorine-containing monomers have C-F bond structures which are symmetrically distributed, the symmetrically distributed high electronegativity F atoms can stabilize the surrounding electron cloud arrangement, reduce the molecular polarizability and facilitate the regulation and control of the dielectric property.
(3) After the introduced fluorine-containing amino monomer participates in the reaction, amino nitrogen atoms can be introduced into the polymer molecular chain, and the amino nitrogen atoms and nitrogen atoms in a triazine ring structure formed after the cyanate is cured form intermolecular hydrogen bonding action, so that molecular polarization can be further restrained, and the dielectric property can be improved.
Drawings
FIG. 1 is a schematic view showing the formation of intermolecular hydrogen bonding of the polymer of the resin material of the present invention.
Detailed Description
The present invention will be described more fully hereinafter with reference to the accompanying drawings, in which some, but not all embodiments of the invention are shown. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, belong to the scope of the present invention.
Example 1:
a preparation method of low dielectric cyanate ester resin based on intermolecular action comprises the following specific steps:
step 1, weighing 100 parts of bisphenol A cyanate ester monomer, 12.5 parts of 1,4-bis (2 ',3' -epoxypropyl) perfluorobutane, 13 parts of 4,4' -diaminooctafluorobiphenyl and 2 parts of dibutyltin dilaurate curing catalyst in parts by weight.
And 2, uniformly mixing the cyanate ester monomer, the fluorine-containing epoxy monomer and the fluorine-containing amino monomer weighed in the step 1, heating and stirring under an oil bath condition at the temperature of 80 ℃ until a mixture solution is clear and transparent and has no insoluble substances, and then, preserving heat for 1 hour at the temperature of 80 ℃ to obtain a mixture a.
And 3, adding 2 parts of the curing catalyst prepared in the step 1 into the mixture a obtained in the step 2, and uniformly stirring to obtain a mixture b.
And 4, pouring the mixture b obtained in the step 3 into a polytetrafluoroethylene mold preheated at 100 ℃, vacuumizing for 30min at 100 ℃ until no visible bubbles exist, and then starting curing according to the curing temperature program of curing at 130 ℃ for 2h, curing at 150 ℃ for 2h, curing at 180 ℃ for 2h and curing at 200 ℃ for 2 h.
Example 2:
a preparation method of low dielectric cyanate resin based on intermolecular action comprises the following specific steps:
step 1, weighing 100 parts of bisphenol A cyanate ester monomer, 22 parts of 1,4-bis (2 ',3' -epoxypropyl) perfluorobutane, 23 parts of 4,4' -diaminooctafluorobiphenyl and 2 parts of dibutyltin dilaurate curing catalyst according to parts by weight.
And 2, uniformly mixing the cyanate ester monomer, the fluorine-containing epoxy monomer and the fluorine-containing amino monomer weighed in the step 1, stirring the mixture under the condition of an oil bath at the temperature of 80 ℃ until the mixture is clear and transparent and has no insoluble substances, and then preserving heat for 2 hours at the temperature of 80 ℃ to obtain a mixture a.
And 3. Step 3. And (3) adding 2 parts of the curing catalyst prepared in the step 1 into the mixture a obtained in the step 2, and uniformly stirring to obtain a mixture b.
And 4, pouring the mixture b obtained in the step 3 into a polytetrafluoroethylene mould preheated at 100 ℃, vacuumizing for 30min at 100 ℃ until no air bubbles are visible, and then starting to cure according to a curing temperature program of curing at 130 ℃ for 2h, curing at 150 ℃ for 2h, curing at 180 ℃ for 2h and curing at 200 ℃ for 2 h.
Example 3:
a preparation method of low dielectric cyanate ester resin based on intermolecular action comprises the following specific steps:
step 1, weighing 100 parts of bisphenol A type cyanate ester monomer, 16 parts of 1,4-bis (2 ',3' -epoxypropyl) perfluorobutane, 17 parts of 4,4' -diaminooctafluorobiphenyl and 2 parts of dibutyltin dilaurate curing catalyst in parts by weight.
And 2, uniformly mixing the cyanate ester monomer, the fluorine-containing epoxy monomer and the fluorine-containing amino monomer weighed in the step 1, stirring the mixture under the condition of an oil bath at the temperature of 80 ℃ until the mixture is clear and transparent and has no insoluble substances, and then preserving heat for 3 hours at the temperature of 80 ℃ to obtain a mixture a.
And 3, adding 2 parts of the curing catalyst prepared in the step 1 into the mixture a obtained in the step 2, and uniformly stirring to obtain a mixture b.
And 4, performing step (5). Pouring the mixture b obtained in the step 3 into a polytetrafluoroethylene mold preheated at 100 ℃, vacuumizing for 30min at 100 ℃ until no visible bubbles exist, and then starting to cure according to a curing temperature program of curing at 130 ℃ for 2h, curing at 150 ℃ for 2h and curing at 180 ℃ for 4 h.
Comparative example:
step 1, weighing 100 parts of bisphenol A cyanate monomer and 2 parts of dibutyltin dilaurate curing catalyst by weight.
And 2, stirring the cyanate ester monomer weighed in the step 1 under the condition of an oil bath at the temperature of 80 ℃ until the cyanate ester monomer is clear and transparent, adding 2 parts of curing catalyst after no insoluble substances exist, and uniformly stirring to obtain a mixture a.
And 3, pouring the mixture a obtained in the step 2 into a polytetrafluoroethylene mould preheated at 100 ℃, vacuumizing for 30min at 100 ℃ until no visible bubbles exist, and then starting to cure according to a curing temperature program of curing at 130 ℃ for 2h, curing at 150 ℃ for 2h, curing at 180 ℃ for 2h and curing at 200 ℃ for 2 h.
The dielectric properties of the cured cyanate ester resins obtained in examples 1 to 3 and comparative example are shown in Table 1, the dielectric properties were measured by the coaxial method, the samples were circular, and the dielectric properties were measured at 7mm outside diameter, 3mm inside diameter, 2 to 3mm thickness, 10GHz measurement frequency, and the average value was obtained by repeating three measurements for each sample.
TABLE 1
Dielectric constant Dielectric loss
Example 1 2.40 0.0149
Example 2 2.54 0.0161
Example 3 2.45 0.0151
Comparative example 2.56 0.0304
Example 1 has the lowest dielectric constant and dielectric loss, example 2 has a dielectric constant comparable to that of the comparative example, but the dielectric loss is significantly lower than that of the comparative example, and example 3 has a dielectric constant and dielectric loss superior to those of the comparative example, but lower than that of example 1. The above parameters are characterized by: example 1 has the minimum dielectric constant and dielectric loss, and can meet the requirements of the resin matrix of the wave-transparent composite material.
The thermal stability of the cured cyanate ester resins obtained in examples 1 to 3 and comparative example is shown in Table 2, and the thermal properties were measured using a thermogravimetric analyzer under a nitrogen atmosphere at a temperature range of 30-850 ℃.
The mechanical property and the thermal property of the polymer material are directly related to the flexibility of a high molecular chain, and to a certain extent, the better the flexibility of the molecular chain in a mesoscale is, and the better toughness is shown macroscopically. Meanwhile, the better the molecular chain flexibility, the more likely the rotation of the chain segment occurs during heating, resulting in lower thermal stability.
TABLE 2
Figure BDA0003598447140000051
Heat resistance index temperature =0.49 × [ T × [ 5 +0.6×(T 30 -T 5 )]，T 5 、T 30 The heat resistance index temperature may reflect the degree of stability of the resin upon temperature change to some extent, corresponding to the thermal weight loss temperatures of 5wt% and 30wt%, respectively.
The comparative example had the largest initial thermal decomposition temperature, but the initial thermal decomposition temperatures of example 1 and example 3 were slightly lower than the comparative example, while the lowest example 3 was also close to 400 ℃, indicating that the modified resin still had higher thermal stability.
The heat resistance index temperature of the comparative example is similar to that of the examples 1 and 3, and the heat resistance index temperature of the example 2 is lower than that of the comparative example. Example 1 still possessed the better thermal stability properties.
It can be seen from the above embodiments that, in the low dielectric cyanate ester resin based on intermolecular interaction provided by the present invention, a polymer molecular network is changed by randomly copolymerizing a plurality of fluorine-containing monomers and cyanate ester monomers, a measure of hydrogen bonding interaction is established between the triazine ring nitrogen atom and the nitrogen atom introduced into the molecular network, and the improvement of the mechanical property, the thermal property and the dielectric property of the cyanate ester resin is realized through the hydrogen bonding interaction between the polymer molecules.

Claims (10)

1. A low dielectric cyanate ester resin based on intermolecular interaction, characterized in that: the curing agent consists of 100 parts by weight of cyanate ester monomer, 1-50 parts by weight of fluorine-containing epoxy monomer, 1-50 parts by weight of fluorine-containing amino monomer and 0-5 parts by weight of curing catalyst;
the molecular structure of the cyanate monomer at room temperature is one or a mixture of more of bisphenol A cyanate, tetramethyl bisphenol F cyanate, bisphenol E cyanate, bisphenol M cyanate, dicyclopentadiene bisphenol cyanate, phenolic cyanate or 4,4' -bis (trifluoromethyl) methylene diphenyl cyanate;
the fluorine-containing epoxy monomer is 1,4-bis (2 ',3' -epoxypropyl) perfluorobutane;
the fluorine-containing amino monomer is one or a mixture of more of 2,2-difluoroethylamine, trifluoroethylamine, pentafluoroethylamine, 1,1,2,2,3,3,3-heptafluoropropane-1-amine, 2,3,5,6-tetrafluoro-1,4-phenylenediamine, 2,4,6-trifluoroaniline, 3,5-difluoroaniline, 2,6-difluoroaniline or 4,4' -diaminooctafluorobiphenyl;
the curing catalyst is an organic tin catalyst and/or a transition metal organic compound catalyst.
2. A low dielectric cyanate ester resin based on intermolecular interactions as claimed in claim 1, wherein: the organic tin catalyst is stannous octoate, di-n-butyl tin oxide, di-n-octyl tin oxide and/or dibutyltin dilaurate.
3. The low dielectric cyanate ester resin based on intermolecular interaction according to claim 1, wherein: the transition metal organic compound catalyst is ferric acetylacetonate, cobalt naphthenate and/or imidazole catalyst.
4. A low dielectric cyanate ester resin based on intermolecular interactions as claimed in claim 1, wherein: the fluorine-containing amino monomer is prepared by selecting a material with an aromatic ring structure and adjusting the content ratio of the material to increase the rigidity of the low dielectric cyanate resin based on intermolecular action.
5. The low dielectric cyanate ester resin based on intermolecular interaction according to claim 1, wherein: the fluorine-containing amino monomer does not select a material with an aromatic ring structure, so that the toughness of the low dielectric cyanate resin based on intermolecular action is improved.
6. The low dielectric cyanate ester resin based on intermolecular interaction according to claim 1, wherein: the fluorine-containing amino monomer is prepared by selecting monomers with different amino group functionalities and adjusting the content ratio of the monomers to reduce the dielectric constant of the low dielectric cyanate resin based on intermolecular interaction.
7. The method for preparing a low dielectric cyanate ester resin based on intermolecular interaction according to claim 1, comprising the steps of:
step 1, weighing 100 parts of cyanate ester monomer, 1-50 parts of fluorine-containing epoxy monomer, 1-50 parts of fluorine-containing amino monomer and 0-5 parts of curing catalyst according to parts by weight;
step 2, dissolving and uniformly mixing the cyanate ester monomer, the fluorine-containing epoxy monomer and the fluorine-containing amino monomer weighed in the step 1 under the condition of water bath or oil bath at the temperature of 70-90 ℃ to obtain a clear and transparent mixture without insoluble substances; then, carrying out thermal-insulation prepolymerization reaction for 0-3 h at the temperature of 70-90 ℃ to obtain a mixture a;
step 3, adding the curing catalyst prepared in the step 1 into the mixture a obtained in the step 2, and uniformly mixing to obtain a mixture b;
and 4, curing the mixture b at 130-220 ℃ to obtain the low dielectric cyanate resin based on intermolecular action.
8. The method for preparing a low dielectric cyanate ester resin based on intermolecular interaction according to claim 7, wherein: the step 4 is carried out in a polytetrafluoroethylene mould preheated at the temperature of 80-100 ℃ so as to ensure that the curing effect is better.
9. The method for preparing a low dielectric cyanate ester resin based on intermolecular interaction according to claim 7, wherein: the step 4 of curing comprises the step of vacuumizing and exhausting at the temperature of 80-100 ℃ to remove air bubbles in the mixture b, so that the curing effect is better.
10. The method for preparing a low dielectric cyanate ester resin based on intermolecular interaction according to claim 7, wherein: the curing temperature of the step 4 is increased by at least 2 times at 130-220 ℃, and the curing temperature program is respectively kept for at least 1h for curing, so that the final cured product has better uniformity.
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