CN101824148A - Bismaleimide-triazine resin and preparation method thereof - Google Patents
Bismaleimide-triazine resin and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a bismaleimide-triazine resin containing octavinyl polyhedral oligomeric silsesquioxane and a preparation method thereof. By weight, 100 parts of bismaleimide is slowly added into O,O'-diallylbisphenol A under 120 DEG C to 140 DEG C, so that prepolymer I is obtained; 1894 parts of octavinyl polyhedral oligomeric silsesquioxane is slowly added into the prepolymer I with the temperature of 120 DEG C to 140 DEG C, so that prepolymer II is obtained; 215 to 280 parts of cyanate ester is weighed and slowly added into the prepolymer II, the temperature is increased to 140 DEG C to 160 DEG C, stirring is carried out for 1 to 2 hours while the temperature is kept, and thereby the bismaleimide-triazine resin containing the octavinyl polyhedral oligomeric silsesquioxane is obtained. The preparation technique is simple and easy to operate, and has wide applicability; and the produced resin can be used as base material for the preparation of high-performance copper-clad plates and the like in the field of electronic information, as well as the preparation of advanced resin-based composite material, adhesive, insulating paint and the like, so the resin has a wide application prospect.
Description
Technical field
The present invention relates to a kind of performance resins and preparation method thereof, be specifically related to a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes and preparation method thereof, belong to technical field of polymer materials.
Background technology
The resin system that Bismaleimide Triazine (BT) resin is made up of bismaleimides (BMI) and cyanate (CE), it has outstanding thermotolerance, dielectric properties, wet-hot aging performance, and good mechanical characteristics, resistance to chemical reagents, radioresistens, wear resistance and dimensional stability, be considered to one of resin kind for preparing the tool potentiality of high-frequency high-speed printed circuit board (pcb).The production of China BT resin also is in blank.Abroad the development of BT resin base pcb board is mainly carried out in beautiful, day two countries, aggregate level also is in initial period at present.Wherein Japan has developed BT resin base PCB, and small-scale production is arranged.But that is that all right is ripe for the BT product, and the subject matter of existence is that the relative permittivity and the thermal expansivity of BT resin is higher, remains further to be improved.The research and development of carrying out novel high-performance BT resin have important scientific research meaning and using value.
Cagelike silsesquioxane (POSS) is a kind of special silicoorganic compound, the inorganic kernel that its intramolecule is made up of Si-O-Si, the periphery is surrounded by organic group, inorganic kernel provides good thermotolerance for material, and peripheral organic group and polymeric matrix have good consistency, thereby can form the hybrid material of molecular level by blend or polymeric method, thereby change the molecular structure of organic polymer, increase the rigidity of molecular chain, improve the over-all properties of polymkeric substance.The POSS molecule contains equally distributed nano-pore structure, comprises air (specific inductivity is 1) in the nanoporous, and the POSS molecule also has lower polarity simultaneously, so the POSS molecule has lower specific inductivity (2.1-2.7) and dielectric loss.Research work about the POSS/ polymer materials has had more report, and result of study shows that generally the adding of POSS can effectively improve mechanics, the thermal property of polymkeric substance, and reduces the specific inductivity and the dielectric loss of polymkeric substance.
Before the present invention makes, POSS can be referring to document " Thermal and dielectric properties of bismaleimide-triazine resinscontaining octa (maleimidophenyl) silsesquioxane " (Journal of AppliedPolymer Science, 2008 to the research of BT resin modified aspect; 109:3114-3121.), it has reported a kind of method of utilizing eight (dimaleoyl imino phenyl) cage-type silsesquioxane (OMPS) modification BT resins, after in the BT resin, adding 1wt%OMPS, the thermomechanical property of material is improved, simultaneously, the specific inductivity of material has dropped to 3.7 by 4.2.But such preparation that contains the maleimide of POSS structure exists significantly not enough, shows that complex process, productive rate are lower.For example, in the process of maleimide amino acid dehydration, under the effect of acid, the Si-O-Si key ruptures easily, thereby makes the cage-type silsesquioxane with ordered structure be cracked into random structure, influences the performance of material.
In the POSS of numerous different structures, eight ethenyl cage model sesquialter siloxanes (POSS-Vi) have great application value, are mainly used in the research field of dielectric film and Electronic Packaging.But, adopt the productive rate lower (18.2%) that has the synthetic POSS-Vi of method institute now, be unfavorable for large-scale application.
Summary of the invention
The object of the invention provides a kind of polymer microballoon with satisfactory stability and mechanical property and preparation method thereof.
The technical solution used in the present invention is: a kind of bismaleimides-cyanate resin, by weight, it comprises 100 parts of bismaleimidess, 43～86 parts of O, O '-diallyl bisphenol, 18～94 part of eight ethenyl cage model sesquialter siloxane (POSS-Vi) and 215～280 parts of cyanates.
The invention provides a kind of preparation method of bismaleimides-cyanate resin, comprise the steps:
(1) by weight, take by weighing 100 parts of bismaleimidess and 43-86 part O respectively, O '-diallyl bisphenol, under 120～140 ℃ temperature condition, 100 parts of bismaleimidess are slowly joined O, in O '-diallyl bisphenol, treat that bismaleimides dissolves the back fully and continues to stir 10～30 minutes, obtain performed polymer I;
(2) by weight, with 18～94 part of eight ethenyl cage model sesquialter siloxane, under stirring condition, join lentamente among the performed polymer I that is obtained by step 1, the temperature of this performed polymer is 120～140 ℃; After the interpolation of eight ethenyl cage model sesquialter siloxanes finishes, continue to stir 10～20 minutes, obtain performed polymer II;
(3) by weight, take by weighing 215～280 parts of cyanates, slowly join among the performed polymer II that obtains by step 2, treat to be warming up to 140～160 ℃ after cyanate dissolves fully, under heat-retaining condition, continue to stir 1～2 hour, obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Described bismaleimides is N, N '-4,4 '-diphenyl methane dimaleimide, 4,4 '-dimaleoyl imino phenyl ether, 4,4 '-dimaleoyl imino sulfobenzide, 2-methyl isophthalic acid, a kind of in the 5-dimaleoyl imino benzene or their arbitrary combination.
The general molecular formula of described cyanate is NCO-R-OCN, and wherein, R is an aromatic structure.
The preparation method of described eight ethenyl cage model sesquialter siloxanes comprises the steps:
(1) by weight, 49～63 parts of vinyl silanes are dissolved in 129～150 parts of organic alcohol, after fully stirring, add 20 parts of deionized waters; Described vinyl silanes is vinyltrimethoxy silane or vinyltriethoxysilane; Described organic alcohol is ethanol or methyl alcohol;
(2) the pH value of regulating above-mentioned solution with concentrated hydrochloric acid or acetate is 2.5～3.5, at N
2Protection was reacted 5～15 hours down, and underpressure distillation at normal temperatures removes solvent again, obtains crude product;
(3) with above-mentioned crude product recrystallization in acetone, obtain the needle-like white crystal, obtain structural formula after the oven dry and be
Eight ethenyl cage model sesquialter siloxanes.
Because the utilization of technique scheme, the present invention compared with prior art has following advantage:
1, the present invention adopts POSS-Vi and bismaleimides/O, the method of O '-diallyl bisphenol copolymerization, compare with the method (eigenmode) that the directly synthetic POSS that contains dimaleoyl imino of prior art prepares modification BT resin, its preparation modification BT resin has the advantage that technology is simple, be easy to scale operation.
2, the present invention is with bismaleimides/O, and O '-diallyl bisphenol is one of essentially consist, and prepared modification BT resin has more excellent manufacturability and more outstanding toughness.
3, compare with organic alcohol, POSS-Vi is easier to form crystallite in acetone, so the present invention adopts the solvent of acetone as recrystallization, and more POSS-Vi is separated out from solvent, thereby obtains the POSS-Vi of higher yields (＞27%).
4, a kind of simple, easy row of preparation technology that contains the bismaleimides-cyanate resin of eight ethenyl cage model sesquialter siloxanes disclosed by the invention, suitability is wide, prepared resin can not only be used to prepare the base mateiral of electronic information fields such as printed circuit board, but also can be used for the advanced composite material in fields such as aerospace, communications and transportation and sizing agent thereof etc.
Embodiment
Below in conjunction with embodiment the present invention is further described.
Embodiment one:
Take by weighing 100 parts of N respectively, N '-4,4 '-diphenyl methane dimaleimide (BDM) and 43 parts of O, O '-diallyl bisphenol slowly joins O with 100 parts of BDM, in O '-diallyl bisphenol under 120 ℃; After treating that BDM dissolves fully, continue to stir 10 minutes.Obtain the performed polymer of DBA/BDM.
49 parts of vinyltrimethoxy silanes are dissolved in 129 parts of methyl alcohol, after fully stirring, add 20 parts of deionized waters; Functional quality concentration is that 36.5% hydrochloric acid is regulated its pH value to 3, at N
2Protection was reacted 10 hours down.After underpressure distillation removed solvent under the normal temperature, recrystallization in acetone obtained the needle-like white crystal, and 60 ℃ of vacuum dryings get eight ethenyl cage model sesquialter siloxanes (POSS-Vi) white solid powder, and its structural formula is:
Take by weighing 18 parts of POSS-Vi, under stirring condition, add temperature slowly and be in 120 ℃ the performed polymer of DBA/BDM.After the POSS-Vi interpolation finishes, continue to stir 10 minutes, obtain the performed polymer of POSS-Vi/DBA/BDM.
Take by weighing 215 parts bisphenol A cyanate ester (BADCy), slowly add in the POSS-Vi/DBA/BDM performed polymer, after treating that cyanate dissolves fully, be warming up to 150 ℃ and continued insulated and stirred 1 hour, promptly obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Embodiment two:
Take by weighing 100 parts of N respectively, N '-4,4 '-diphenyl methane dimaleimide (BDM) and 86 parts of diallyl bisphenols slowly join 100 parts of BDM in the diallyl bisphenol under 140 ℃; After treating that BDM dissolves fully, continue to stir 30 minutes.Obtain the performed polymer of DBA/BDM.
55 parts of vinyltrimethoxy silanes are dissolved in 140 parts of methyl alcohol, after fully stirring, add 20 parts of deionized waters; Use acetate adjust pH to 3, at N
2Protection was reacted 10 hours down.After underpressure distillation removed solvent under the normal temperature, recrystallization in acetone obtained the needle-like white crystal, and 60 ℃ of vacuum dryings get eight ethenyl cage model sesquialter siloxane white solid powder.
Take by weighing 18 parts of POSS-Vi, under stirring condition, add temperature slowly and be in 140 ℃ the performed polymer of DBA/BDM.After the POSS-Vi interpolation finishes, continue to stir 15 minutes, obtain the performed polymer of POSS-Vi/DBA/BDM.
Take by weighing 280 parts bisphenol A cyanate ester (BADCy), slowly add in the POSS-Vi/DBA/BDM performed polymer, after treating that cyanate dissolves fully, be warming up to 150 ℃ and continued insulated and stirred 2 hours, promptly obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Embodiment three:
Take by weighing 100 parts of N respectively, N '-4,4 '-diphenyl methane dimaleimide (BDM) and 86 parts of diallyl bisphenols slowly join 100 parts of BDM in the diallyl bisphenol under 140 ℃; After treating that BDM dissolves fully, continue to stir 25 minutes.Obtain the performed polymer of DBA/BDM.
63 parts of vinyltriethoxysilanes are dissolved in 150 parts of ethanol, after fully stirring, add 20 parts of deionized waters; Use acetate adjust pH to 3, at N
2Protection was reacted 10 hours down.After underpressure distillation removed solvent under the normal temperature, recrystallization in acetone obtained the needle-like white crystal, and 60 ℃ of vacuum dryings get eight ethenyl cage model sesquialter siloxane white solid powder.
Take by weighing 18 parts of POSS-Vi, under stirring condition, add temperature slowly and be in 140 ℃ the performed polymer of DBA/BDM.After the POSS-Vi interpolation finishes, continue to stir 15 minutes, obtain the performed polymer of POSS-Vi/DBA/BDM.
Take by weighing 280 parts bisphenol A cyanate ester (BADCy), slowly add in the POSS-Vi/DBA/BDM performed polymer, after treating that cyanate dissolves fully, be warming up to 150 ℃ and continued insulated and stirred 1.5 hours, promptly obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Embodiment four:
Take by weighing 45 parts of N respectively, N '-4,4 '-diphenyl methane dimaleimide, 55 part 4,4 '-dimaleoyl imino phenyl ether and 86 parts of diallyl bisphenols slowly join above-mentioned BMI mixture in the diallyl bisphenol under 140 ℃; After treating that BMI dissolves fully, continue to stir 20 minutes.Obtain the performed polymer of DBA/BMI.
63 parts of vinyltriethoxysilanes are dissolved in 150 parts of ethanol, after fully stirring, add 20 parts of deionized waters; Use acetate adjust pH to 3, at N
2Protection was reacted 10 hours down.After underpressure distillation removed solvent under the normal temperature, recrystallization in acetone obtained the needle-like white crystal, and 60 ℃ of vacuum dryings get eight ethenyl cage model sesquialter siloxane white solid powder.
Take by weighing 18 parts of POSS-Vi, under stirring condition, add temperature slowly and be in 140 ℃ the performed polymer of DBA/BMI.After the POSS-Vi interpolation finishes, continue to stir 10 minutes, obtain the performed polymer of POSS-Vi/DBA/BMI.
Take by weighing 280 parts bisphenol A cyanate ester (BADCy), slowly add in the POSS-Vi/DBA/BMI performed polymer, after treating that cyanate dissolves fully, be warming up to 150 ℃ and continued insulated and stirred 1 hour, promptly obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Embodiment five:
Take by weighing 100 part 4 respectively, 4 '-dimaleoyl imino sulfobenzide and 86 parts of diallyl bisphenols slowly join above-mentioned BMI in the diallyl bisphenol under 140 ℃; After treating that BMI dissolves fully, continue to stir 30 minutes.Obtain the performed polymer of DBA/BMI.
50 parts of vinyltriethoxysilanes are dissolved in 140 parts of ethanol, after fully stirring, add 20 parts of deionized waters; Use acetate adjust pH to 3, at N
2Protection was reacted 10 hours down.After underpressure distillation removed solvent under the normal temperature, recrystallization in acetone obtained the needle-like white crystal, and 60 ℃ of vacuum dryings get eight ethenyl cage model sesquialter siloxane white solid powder.
Take by weighing 93 parts of POSS-Vi, under stirring condition, add temperature slowly and be in 140 ℃ the performed polymer of DBA/BMI.After the POSS-Vi interpolation finishes, continue to stir 20 minutes, obtain the performed polymer of POSS-Vi/DBA/BMI.
Take by weighing 280 parts dicyclopentadiene bisphenol type cyanic acid vinegar (DCPDCE), slowly add in the POSS-Vi/DBA/BMI performed polymer, be warming up to 150 ℃ and continued insulated and stirred 2 hours, promptly obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Embodiment six:
Take by weighing 100 parts of 2-methyl isophthalic acids respectively, 5-dimaleoyl imino benzene and 86 parts of diallyl bisphenols slowly join above-mentioned BMI in the diallyl bisphenol under 140 ℃; After treating that BMI dissolves fully, continue to stir 25 minutes.Obtain the performed polymer of DBA/BMI.
63 parts of vinyltriethoxysilanes are dissolved in 150 parts of ethanol, after fully stirring, add 20 parts of deionized waters; Use acetate adjust pH to 3, at N
2Protection was reacted 10 hours down.After underpressure distillation removed solvent under the normal temperature, recrystallization in acetone obtained the needle-like white crystal, and 60 ℃ of vacuum dryings get eight ethenyl cage model sesquialter siloxane white solid powder.
Take by weighing 93 parts of POSS-Vi, under stirring condition, add temperature slowly and be in 140 ℃ the performed polymer of DBA/BMI.After the POSS-Vi interpolation finishes, continue to stir 20 minutes, obtain the performed polymer of POSS-Vi/DBA/BMI.
Take by weighing 215 parts dicyclopentadiene bisphenol type cyanic acid vinegar (DCPDCE), slowly add in the POSS-Vi/DBA/BMI performed polymer, be warming up to 150 ℃ and continued insulated and stirred 2 hours, promptly obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
Claims (8)
1. bismaleimides-cyanate resin, it is characterized in that: by weight, it comprises 100 parts of bismaleimidess, 43～86 parts of O, O '-diallyl bisphenol, 18～94 part of eight ethenyl cage model sesquialter siloxane and 215～280 parts of cyanates.
2. a kind of bismaleimides-cyanate resin according to claim 1, it is characterized in that: described bismaleimides is N, N '-4,4 '-diphenyl methane dimaleimide, 4,4 '-dimaleoyl imino phenyl ether, 4,4 '-dimaleoyl imino sulfobenzide, 2-methyl isophthalic acid, a kind of in the 5-dimaleoyl imino benzene or their arbitrary combination.
3. a kind of bismaleimides-cyanate resin according to claim 1 is characterized in that: the general molecular formula of described cyanate is NCO-R-OCN, and wherein, R is an aromatic structure.
4. a kind of bismaleimides-cyanate resin according to claim 1 is characterized in that: the structural formula of described eight ethenyl cage model sesquialter siloxanes is
5. the preparation method of a bismaleimides-cyanate resin is characterized in that comprising the steps:
(1) by weight, take by weighing 100 parts of bismaleimidess and 43-86 part O respectively, O '-diallyl bisphenol, under 120～140 ℃ temperature condition, 100 parts of bismaleimidess are slowly joined O, in O '-diallyl bisphenol, treat that bismaleimides dissolves the back fully and continues to stir 10～30 minutes, obtain performed polymer I;
(2) by weight, with 18～94 part of eight ethenyl cage model sesquialter siloxane, under stirring condition, join lentamente among the performed polymer I that is obtained by step 1, the temperature of this performed polymer is 120～140 ℃; After the interpolation of eight ethenyl cage model sesquialter siloxanes finishes, continue to stir 10～20 minutes, obtain performed polymer II;
(3) by weight, take by weighing 215～280 parts of cyanates, slowly join among the performed polymer II that obtains by step 2, treat to be warming up to 140～160 ℃ after cyanate dissolves fully, under heat-retaining condition, continue to stir 1～2 hour, obtain a kind of bismaleimides-cyanate resin that contains eight ethenyl cage model sesquialter siloxanes.
6. the preparation method of a kind of bismaleimides-cyanate resin according to claim 5, it is characterized in that: described bismaleimides is N, N '-4,4 '-diphenyl methane dimaleimide, 4,4 '-dimaleoyl imino phenyl ether, 4,4 '-dimaleoyl imino sulfobenzide, 2-methyl isophthalic acid, a kind of in the 5-dimaleoyl imino benzene or their arbitrary combination.
7. the preparation method of a kind of bismaleimides-cyanate resin according to claim 5, it is characterized in that: the general molecular formula of described cyanate is NCO-R-OCN, wherein, R is an aromatic structure.
8. the preparation method of a kind of bismaleimides-cyanate resin according to claim 5, it is characterized in that: the preparation method of described eight ethenyl cage model sesquialter siloxanes comprises the steps:
(1) by weight, 49～63 parts of vinyl silanes are dissolved in 129～150 parts of organic alcohol, after fully stirring, add 20 parts of deionized waters; Described vinyl silanes is vinyltrimethoxy silane or vinyltriethoxysilane; Described organic alcohol is ethanol or methyl alcohol;
(2) the pH value of regulating above-mentioned solution with concentrated hydrochloric acid or acetate is 2.5～3.5, at N
2Protection was reacted 5～15 hours down, and underpressure distillation at normal temperatures removes solvent again, obtains crude product;
(3) with above-mentioned crude product recrystallization in acetone, obtain the needle-like white crystal, obtain structural formula after the oven dry and be
Eight ethenyl cage model sesquialter siloxanes.
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Cited By (10)
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| CN101974225A (en) * | 2010-09-21 | 2011-02-16 | 苏州大学 | Microporous silicon/bismaleimide-triazine resin composite material and preparation method thereof |
| CN103756314A (en) * | 2013-12-17 | 2014-04-30 | 中航复合材料有限责任公司 | Preparation method of bismaleimide resin used for composite material liquid molding |
| CN106967475A (en) * | 2017-04-20 | 2017-07-21 | 安徽春辉仪表线缆集团有限公司 | A kind of ER fluid of nano titanium oxide grafted ethene based polysiloxane and preparation method thereof |
| CN107978383A (en) * | 2016-10-21 | 2018-05-01 | E.I.内穆尔杜邦公司 | Conducting paste composition and with its manufactured semiconductor device |
| CN109988302A (en) * | 2017-12-29 | 2019-07-09 | 洛阳尖端技术研究院 | Modified cyanic acid ester and preparation method thereof |
| CN110128821A (en) * | 2019-05-14 | 2019-08-16 | 南京信息职业技术学院 | A kind of high thermal conductivity low-k bismaleimide-triazine resin and preparation method thereof |
| CN112080066A (en) * | 2020-08-20 | 2020-12-15 | 宁波市佳溪电气有限公司 | Plastic body with heat insulation and moisture prevention functions and preparation method and application thereof |
| CN113789055A (en) * | 2020-12-28 | 2021-12-14 | 重庆工商大学 | MOFs modified BT nano composite material containing transition metal and active hydrogen and preparation method thereof |
| WO2022266951A1 (en) * | 2021-06-24 | 2022-12-29 | 穗晔实业股份有限公司 | Thermosetting resin composition and prepreg |
| US11639439B2 (en) | 2021-06-24 | 2023-05-02 | Prior Company Limited | Thermosetting resin composition and prepreg |
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| CN101974225A (en) * | 2010-09-21 | 2011-02-16 | 苏州大学 | Microporous silicon/bismaleimide-triazine resin composite material and preparation method thereof |
| CN101974225B (en) * | 2010-09-21 | 2013-03-27 | 苏州大学 | Microporous silicon/bismaleimide-triazine resin composite material and preparation method thereof |
| CN103756314A (en) * | 2013-12-17 | 2014-04-30 | 中航复合材料有限责任公司 | Preparation method of bismaleimide resin used for composite material liquid molding |
| CN103756314B (en) * | 2013-12-17 | 2016-04-20 | 中航复合材料有限责任公司 | For the preparation method of the bimaleimide resin of matrix material liquid condition shaping |
| CN107978383A (en) * | 2016-10-21 | 2018-05-01 | E.I.内穆尔杜邦公司 | Conducting paste composition and with its manufactured semiconductor device |
| CN106967475A (en) * | 2017-04-20 | 2017-07-21 | 安徽春辉仪表线缆集团有限公司 | A kind of ER fluid of nano titanium oxide grafted ethene based polysiloxane and preparation method thereof |
| CN109988302A (en) * | 2017-12-29 | 2019-07-09 | 洛阳尖端技术研究院 | Modified cyanic acid ester and preparation method thereof |
| CN110128821A (en) * | 2019-05-14 | 2019-08-16 | 南京信息职业技术学院 | A kind of high thermal conductivity low-k bismaleimide-triazine resin and preparation method thereof |
| CN110128821B (en) * | 2019-05-14 | 2022-08-02 | 南京信息职业技术学院 | Bismaleimide-triazine resin with high thermal conductivity and low dielectric constant and preparation method thereof |
| CN112080066A (en) * | 2020-08-20 | 2020-12-15 | 宁波市佳溪电气有限公司 | Plastic body with heat insulation and moisture prevention functions and preparation method and application thereof |
| CN112080066B (en) * | 2020-08-20 | 2022-09-02 | 宁波市佳溪电气有限公司 | Plastic body with heat insulation and moisture prevention functions and preparation method and application thereof |
| CN113789055A (en) * | 2020-12-28 | 2021-12-14 | 重庆工商大学 | MOFs modified BT nano composite material containing transition metal and active hydrogen and preparation method thereof |
| WO2022266951A1 (en) * | 2021-06-24 | 2022-12-29 | 穗晔实业股份有限公司 | Thermosetting resin composition and prepreg |
| US11639439B2 (en) | 2021-06-24 | 2023-05-02 | Prior Company Limited | Thermosetting resin composition and prepreg |
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