CN117624528A - Low-dielectric benzoxazine-cyanate copolymer resin and preparation method thereof - Google Patents
Low-dielectric benzoxazine-cyanate copolymer resin and preparation method thereof Download PDFInfo
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- CN117624528A CN117624528A CN202311644093.7A CN202311644093A CN117624528A CN 117624528 A CN117624528 A CN 117624528A CN 202311644093 A CN202311644093 A CN 202311644093A CN 117624528 A CN117624528 A CN 117624528A
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- benzoxazine
- cyanate
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- bisphenol
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- 229920006026 co-polymeric resin Polymers 0.000 title claims abstract description 18
- JNQPUDXZZPZDHB-UHFFFAOYSA-N 2H-1,2-benzoxazine cyanic acid Chemical compound OC#N.N1Oc2ccccc2C=C1 JNQPUDXZZPZDHB-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 229920005989 resin Polymers 0.000 claims abstract description 117
- 239000011347 resin Substances 0.000 claims abstract description 117
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims abstract description 53
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims abstract description 42
- 239000004643 cyanate ester Substances 0.000 claims abstract description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 9
- 229910001220 stainless steel Inorganic materials 0.000 claims description 9
- 239000010935 stainless steel Substances 0.000 claims description 9
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000001913 cyanates Chemical class 0.000 claims 1
- 229920001002 functional polymer Polymers 0.000 abstract description 2
- 239000002861 polymer material Substances 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920006271 aliphatic hydrocarbon resin Polymers 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/12—Chemically modified polycondensates
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention belongs to the field of functional polymer materials, and relates to a low-dielectric benzoxazine-cyanate copolymer resin and a preparation method thereof. The low dielectric benzoxazine-cyanate ester copolymer resin includes: 10-50 mass percent of cyanate resin and 50-90 mass percent of benzoxazine resin.
Description
Technical Field
The invention belongs to the field of functional polymer materials, and relates to a low-dielectric benzoxazine-cyanate copolymer resin and a preparation method thereof.
Background
With the rapid development of high-frequency technology in recent years, the integration level of devices is increasingly improved and the size of elements is reduced, so that the conventional dielectric material cannot solve the serious signal delay problem, and therefore, the requirement for the high-frequency low-dielectric material is increasingly high. This not only requires such materials to maintain low dielectric constant and dielectric loss at high frequencies, but also places higher demands on their low water absorption, processability, etc. application conditions.
The benzoxazine resin is a novel thermosetting resin, no small molecules are released in the curing process, the curing shrinkage rate is almost zero, and the benzoxazine resin has the characteristics of high modulus, high strength, good heat resistance and low water absorption. The benzoxazine resin has the characteristic of flexible molecular design, can be designed and prepared into a low dielectric material based on the characteristic, and has wide application prospect in the field of high-wave-transparent composite materials. To obtain a benzoxazine resin with a low dielectric constant and loss tangent, many approaches have been proposed, and copolymerization modification with other resins is a common method for reducing the dielectric constant of the benzoxazine resin.
CN107987471 a Zeng Ming and the like invent a high-frequency low-dielectric main chain benzoxazine composite resin which is obtained by crosslinking polymerization of 50-90 parts by weight of main chain type benzoxazine and 10-50 parts by weight of hydrocarbon resin, and the resin has the characteristics of low dielectric constant, low loss tangent and excellent flexibility under the condition of high-frequency electromagnetic waves. However, the introduction of aliphatic hydrocarbon resins inevitably results in a decrease in the mechanical strength of the resin matrix. CN110577624a plum loyal and the like synthesize two fluorine-containing aromatic and aliphatic benzoxazine monomers, and the two monomers are mixed with epoxy resin for curing, so that the benzoxazine resin with high performance is obtained, and the resin has good thermal stability, dielectric constant of 2.79-2.96 and loss tangent of 0.013-0.014. The epoxy resin is polar resin, has higher dielectric constant and loss tangent, and has no obvious dielectric property modification effect on the benzoxazine resin when being copolymerized with the benzoxazine resin.
Disclosure of Invention
The invention aims to: the low dielectric benzoxazine-cyanate copolymer resin and the preparation method thereof are provided, cyanate is a high-performance resin matrix developed after epoxy resin and bismaleimide resin, has the characteristics of low dielectric property, high temperature resistance and high strength, and can be subjected to copolymerization reaction with benzoxazine resin to generate a low-polarity diphenyl ether structure, so that the low dielectric copolymer is obtained.
The technical scheme is as follows:
in a first aspect, there is provided a low dielectric benzoxazine-cyanate ester copolymer resin comprising: 10-50 mass percent of cyanate resin and 50-90 mass percent of benzoxazine resin. .
The benzoxazine resin is A-type benzoxazine resin or B-type benzoxazine resin, and the molecular formula structure is as follows:
the cyanate resin is bisphenol A type cyanate, bisphenol AF type cyanate or bisphenol M type cyanate resin;
the molecular structural formula of bisphenol A cyanate is:
the molecular structural formula of bisphenol AF type cyanate is:
the molecular structural formula of the bisphenol M type cyanate resin is as follows:
in a second aspect, a method for preparing a low dielectric benzoxazine-cyanate ester copolymer resin is provided, comprising:
the copolymer resin with excellent dielectric property and mechanical property is prepared by using bisphenol A type cyanate and bisphenol AF type cyanate to carry out copolymerization reaction with two main chain type benzoxazine resins.
The copolymer resin with excellent dielectric property and mechanical property is prepared by using bisphenol A type cyanate and bisphenol AF type cyanate to carry out copolymerization reaction with two main chain type benzoxazine resins, and the copolymer resin comprises the following components:
adding 10-50 mass percent of cyanate resin into a glass container, preparing 50-90 mass percent of benzoxazine resin, fully mixing the two resins by a blending technology, pouring the mixture into a stainless steel mold, and reacting and curing to obtain a resin cured product.
The reaction temperature is as follows: 120-200 ℃.
The reaction time is 8-20 h.
The blending technology comprises the following steps:
(1) melting cyanate at 80-100 ℃, then adding benzoxazine, and fully melting and stirring at 80-100 ℃;
(2) and (3) adding an acetone or butanone solvent into the cyanate ester at room temperature to dissolve the cyanate ester completely, adding the acetone or butanone solvent into the benzoxazine resin, mixing the two resin solutions after the acetone or butanone solvent is dissolved completely, distilling under reduced pressure, and removing the solvent to obtain the resin which is uniformly mixed.
The distillation under reduced pressure is carried out at 80-100 ℃.
The beneficial effects are that:
the invention adopts cyanate resin to carry out copolymerization modification on benzoxazine resin to prepare low dielectric, high-strength and high-temperature resistant copolymer resin, which can meet the performance requirements of radome skin materials, printed circuit boards and electronic potting materials on low-dielectric resin matrixes and can improve the transmission rate of electromagnetic waves.
Detailed Description
The present invention provides a low dielectric benzoxazine-cyanate ester copolymer resin, comprising: 10-50 mass percent of cyanate resin and 50-90 mass percent of benzoxazine resin. .
The benzoxazine resin is A-type benzoxazine resin or B-type benzoxazine resin, and the molecular formula structure is as follows:
the cyanate resin is bisphenol A type cyanate, bisphenol AF type cyanate or bisphenol M type cyanate resin;
the molecular structural formula of bisphenol A cyanate is:
the molecular structural formula of bisphenol AF type cyanate is:
the molecular structural formula of the bisphenol M type cyanate resin is as follows:
the invention also provides a preparation method of the low-dielectric benzoxazine-cyanate copolymer resin, which comprises the following specific steps: adding 10-50 mass percent of cyanate resin into a glass container, preparing 50-90 mass percent of benzoxazine resin, fully mixing the two resins by a blending technology, pouring the mixture into a stainless steel mold, and carrying out reaction curing at 120-200 ℃ for 8-20 hours to obtain a resin cured product.
The mixing technology is as follows: (1) melting cyanate at 80-100 ℃, then adding benzoxazine, and fully melting and stirring at 80-100 ℃; (2) and (3) adding acetone or butanone solvent into cyanate ester at room temperature to dissolve completely, adding acetone or butanone solvent into benzoxazine resin, mixing the two resin solutions after complete dissolution, and distilling under reduced pressure at 80-100 ℃ to remove the solvent to obtain the uniformly mixed resin.
Example 1
Adding 50 mass fractions of bisphenol A type cyanate resin into a glass container, preparing 50 mass fractions of A type benzoxazine resin, melting cyanate ester at 90 ℃ by a melt blending method, then adding benzoxazine, fully melting and stirring at 100 ℃, uniformly mixing the two resins, pouring the two resins into a stainless steel mold, and carrying out curing reaction at 120 ℃ multiplied by 2h+150 ℃ multiplied by 2h+180 ℃ multiplied by 2h+220 ℃ multiplied by 2h to obtain a resin cured product.
The glass transition temperature of the obtained resin cured product was 210℃and the flexural strength was 135MPa, and the dielectric constant and loss tangent at 10GHz were 2.75 and 0.010, respectively.
Example 2
Adding 40 mass fractions of bisphenol AF type cyanate ester resin into a glass container, preparing 60 mass fractions of A type benzoxazine resin, adding an acetone solvent into the cyanate ester resin at room temperature, adding a butanone solvent into the benzoxazine resin, mixing the two resin solutions after complete dissolution, and distilling under reduced pressure at 100 ℃ to remove the solvent to obtain the uniformly mixed resin. Pouring the mixture into a stainless steel mold, and carrying out curing reaction at 150 ℃ for 2 hours, 180 ℃ for 4 hours and 220 ℃ for 2 hours to obtain a resin cured product.
The obtained resin cured product had a glass transition temperature of 220℃and a flexural strength of 110MPa, and a dielectric constant and a loss tangent at 10GHz of 2.65 and 0.006, respectively.
Example 3
Adding 10 mass fractions of bisphenol M type cyanate resin into a glass container, preparing 90 mass fractions of B type benzoxazine resin, melting cyanate ester at 90 ℃ by a melt blending method, then adding benzoxazine, fully melting and stirring at 100 ℃, uniformly mixing the two resins, pouring the two resins into a stainless steel mold, and carrying out curing reaction at 150 ℃ multiplied by 4h+180 ℃ multiplied by 4h+220 ℃ multiplied by 2h to obtain a resin cured product.
The glass transition temperature of the obtained resin cured product was 190℃and the flexural strength thereof was 90MPa, and the dielectric constant and loss tangent at 10GHz were 2.65 and 0.008, respectively.
Example 4
Adding 10 mass fractions of bisphenol A type cyanate ester resin into a glass container, preparing 90 mass fractions of B type benzoxazine resin, melting cyanate ester at 90 ℃ by a melt blending method, then adding benzoxazine, fully melting and stirring at 100 ℃, uniformly mixing the two resins, pouring the two resins into a stainless steel mold, and carrying out curing reaction at 150 ℃ multiplied by 4h+180 ℃ multiplied by 4h+220 ℃ multiplied by 4h to obtain a resin cured product.
The obtained resin cured product had a glass transition temperature of 225℃and a flexural strength of 110MPa, and a dielectric constant and a loss tangent at 10GHz of 2.75 and 0.008, respectively.
Example 5
Adding 30 mass fractions of bisphenol M type cyanate resin into a glass container, preparing 70 mass fractions of A type benzoxazine resin, adding an acetone solvent into the cyanate resin at room temperature, adding a butanone solvent into the benzoxazine resin, mixing the two resin solutions after complete dissolution, and distilling under reduced pressure at 80 ℃ to remove the solvent to obtain the uniformly mixed resin. Pouring the mixture into a stainless steel mold, and carrying out curing reaction at 150 ℃ for 2 hours, 180 ℃ for 4 hours and 200 ℃ for 8 hours to obtain a resin cured product.
The glass transition temperature of the obtained resin cured product was 210℃and flexural strength was 115MPa, and the dielectric constant and loss tangent at 10GHz were 2.63 and 0.006, respectively.
Example 6
Adding 40 mass fractions of bisphenol AF type cyanate ester resin into a glass container, preparing 60 mass fractions of A type benzoxazine resin, adding an acetone solvent into the cyanate ester resin at room temperature, adding a butanone solvent into the benzoxazine resin, mixing the two resin solutions after complete dissolution, and distilling under reduced pressure at 90 ℃ to remove the solvent, thus obtaining the uniformly mixed resin. Pouring the mixture into a stainless steel mold, and carrying out curing reaction at 150 ℃ for 2 hours, 180 ℃ for 4 hours and 190 ℃ for 6 hours to obtain a resin cured product.
The obtained resin cured product had a glass transition temperature of 225℃and a flexural strength of 105MPa, and a dielectric constant and a loss tangent at 10GHz of 2.60 and 0.006, respectively.
Claims (9)
1. A low dielectric benzoxazine-cyanate ester copolymer resin, comprising: 10-50 mass percent of cyanate resin and 50-90 mass percent of benzoxazine resin.
2. The resin according to claim 1, wherein the benzoxazine resin is a type a benzoxazine resin or a type B benzoxazine resin, and has a molecular formula structure of:
a-type benzoxazine resin R= (CH) 2 ) 6 R 1 ＝CH 3
B-type benzoxazine resin, r= (CH) 2 ) 6 R 1 ＝CF 3
3. The resin according to claim 1, wherein the cyanate resin is bisphenol a type cyanate, bisphenol AF type cyanate or bisphenol M type cyanate resin;
the molecular structural formula of bisphenol A cyanate is:
the molecular structural formula of bisphenol AF type cyanate is:
the molecular structural formula of the bisphenol M type cyanate resin is as follows:
4. a method for preparing a low dielectric benzoxazine-cyanate ester copolymer resin, comprising the steps of:
the low dielectric benzoxazine-cyanate copolymer resin of any one of claims 1-3, which has excellent dielectric properties and mechanical properties, is prepared by copolymerization of bisphenol a type and bisphenol AF type cyanate with two main chain type benzoxazine resins.
5. The method according to claim 4, wherein the copolymer resin having excellent dielectric properties and mechanical properties is prepared by copolymerizing bisphenol a type and bisphenol AF type cyanate esters with two main chain type benzoxazine resins, comprising:
adding 10-50 mass percent of cyanate resin into a glass container, preparing 50-90 mass percent of benzoxazine resin, fully mixing the two resins by a blending technology, pouring the mixture into a stainless steel mold, and reacting and curing to obtain a resin cured product.
6. The method of claim 5, wherein the reaction temperature is: 120-200 ℃.
7. The method according to claim 5, wherein the reaction time is 8 to 20 hours.
8. The method of claim 5, wherein the blending technique comprises:
(1) melting cyanate at 80-100 ℃, then adding benzoxazine, and fully melting and stirring at 80-100 ℃;
(2) and (3) adding an acetone or butanone solvent into the cyanate ester at room temperature to dissolve the cyanate ester completely, adding the acetone or butanone solvent into the benzoxazine resin, mixing the two resin solutions after the acetone or butanone solvent is dissolved completely, distilling under reduced pressure, and removing the solvent to obtain the resin which is uniformly mixed.
9. The process according to claim 8, wherein the distillation under reduced pressure is carried out at 80 to 100 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311644093.7A CN117624528A (en) | 2023-12-04 | 2023-12-04 | Low-dielectric benzoxazine-cyanate copolymer resin and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311644093.7A CN117624528A (en) | 2023-12-04 | 2023-12-04 | Low-dielectric benzoxazine-cyanate copolymer resin and preparation method thereof |
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| Publication Number | Publication Date |
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| CN117624528A true CN117624528A (en) | 2024-03-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202311644093.7A Pending CN117624528A (en) | 2023-12-04 | 2023-12-04 | Low-dielectric benzoxazine-cyanate copolymer resin and preparation method thereof |
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| Country | Link |
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| CN (1) | CN117624528A (en) |
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2023
- 2023-12-04 CN CN202311644093.7A patent/CN117624528A/en active Pending
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