CN113121772B - Pterostilbene-based benzoxazine resin and preparation method thereof - Google Patents
Pterostilbene-based benzoxazine resin and preparation method thereof Download PDFInfo
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- CN113121772B CN113121772B CN202110330558.6A CN202110330558A CN113121772B CN 113121772 B CN113121772 B CN 113121772B CN 202110330558 A CN202110330558 A CN 202110330558A CN 113121772 B CN113121772 B CN 113121772B
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- pterostilbene
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- 229920005989 resin Polymers 0.000 title claims abstract description 64
- 239000011347 resin Substances 0.000 title claims abstract description 64
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims abstract description 57
- VLEUZFDZJKSGMX-ONEGZZNKSA-N pterostilbene Chemical compound COC1=CC(OC)=CC(\C=C\C=2C=CC(O)=CC=2)=C1 VLEUZFDZJKSGMX-ONEGZZNKSA-N 0.000 title claims abstract description 42
- VLEUZFDZJKSGMX-UHFFFAOYSA-N pterostilbene Natural products COC1=CC(OC)=CC(C=CC=2C=CC(O)=CC=2)=C1 VLEUZFDZJKSGMX-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 11
- 229920002866 paraformaldehyde Polymers 0.000 claims description 11
- -1 amine compounds Chemical class 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims 1
- 238000005260 corrosion Methods 0.000 abstract description 9
- 230000007797 corrosion Effects 0.000 abstract description 8
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004132 cross linking Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 3
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 3
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 description 6
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical group CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 5
- 229960001669 kinetin Drugs 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical group CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000011825 aerospace material Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000011800 void material Substances 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
- C08G14/06—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 and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09D161/04, C09D161/18 and C09D161/20
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
The invention belongs to the technical field of thermosetting resin, and relates to a pterostilbene-based bio-based benzoxazine resin and a preparation method thereof, in particular to a benzoxazine containing carbon-carbon double bonds and a preparation method thereof. The invention has the advantages that the bio-based pterostilbene is used as a phenol source, and has the characteristic of good environment; the carbon-carbon double bond provided by pterostilbene can further improve the crosslinking density of benzoxazine through high-temperature reaction; the pterostilbene has the molecular structure characteristics, so that the coating has a hydrophobic effect and can well play a role in resisting corrosion; the synthesis steps are simple, and the yield is high; and the cured benzoxazine resin has excellent thermal, mechanical and corrosion resistance. The synthesis process is simple, has lower requirements on equipment, and is suitable for large-scale production.
Description
Technical Field
The invention belongs to the technical field of thermosetting resins, and particularly relates to a pterostilbene-based benzoxazine resin and a preparation method thereof.
Background
The benzoxazine resin is a novel ring-opening polymerization phenolic resin, can generate a similar phenolic resin structure through ring-opening polymerization reaction, and has the advantages of wide raw material source, simple preparation, excellent performance, no volatile matter during curing, low product void ratio and shrinkage rate and the like. The product has excellent mechanical property, heat resistance, electrical insulation, dimensional stability, molding processability, flame retardance and low smoke property, and the most outstanding advantage is very flexible molecular designability, and the molecular structure can be designed by changing the amine source and the phenol source compound. Benzoxazine resin and composite resin with the benzoxazine resin as a matrix are widely applied to some molding processing technologies; and is used as a burn-resistant material, a corrosion-resistant material, an electronic packaging material, a part of a mechanical manufacturing industry, an aerospace material, an adhesive, a circuit board substrate, a vacuum pump rotary vane, an insulating material and other related fields.
With the expansion of application fields, environmental impact is also an important consideration while pursuing high-performance polybenzoxazine materials. The development of materials that are both high performance and environmentally friendly has become a direction for researchers and industry developers. The bio-based benzoxazine resin containing double bond active functional groups prepared by the patent number (CN 107459512A) has no good corrosion resistance and can be prepared for a plurality of days, so that the production cost is high. The patent number (CN 106674214A) uses a three-step method to synthesize the furyl diamine type benzoxazine resin, and the reaction process is complex and is not suitable for large-scale production. Due to the rapid development of the current high polymer materials, the requirements of people on high-performance resin matrixes are increasing. The benzoxazine resin has further improved performance, so that the benzoxazine resin can be widely applied in various fields, such as heat resistance, hydrophobicity and the like, and can be used in high-temperature and corrosive environments.
Disclosure of Invention
In view of the defects of the existing thermosetting resin materials, the invention takes the bio-based pterostilbene as a phenol source, so that the pollution to the environment is reduced from the raw material, the carbon-carbon double bond contained in the pterostilbene can increase the crosslinking degree of the cured resin, the mechanical property of the cured resin can be improved, and the molecular structure of the pterostilbene contains methoxy, so that the benzoxazine resin prepared from the pterostilbene has good hydrophobic effect after curing, and simultaneously has good anti-corrosion function. In addition, the resin has simple synthesis process, high yield and lower equipment requirement, and is suitable for large-scale production.
The invention aims to provide a novel benzoxazine taking bio-based pterostilbene as a phenol source and a preparation method thereof by preparing the bio-based pterostilbene benzoxazine resin, greatly reducing the curing temperature of the benzoxazine resin and simultaneously keeping the resin to have good thermal performance, mechanical performance and corrosion resistance.
The invention aims at realizing the following technical scheme:
one of the purposes of the invention is to provide a pterostilbene-based benzoxazine resin, and the molecular chemical structural formula of the pterostilbene-based benzoxazine resin is shown as follows:
wherein,is one of the following structures:
the prepared benzooxazine resin based on pterostilbene has a curing peak temperature of 200-260 ℃, and the benzooxazine resin based on pterostilbene is further cured and crosslinked to obtain the benzooxazine resin, and the carbon residue rate is 40-80% at 800 ℃ in an inert atmosphere; the resin material after curing has excellent hydrophobicity and corrosion resistance, and the water contact angle is 100-140 degrees.
The second purpose of the invention is to provide a preparation method of the benzoxazine resin with the bio-based pterostilbene as a phenol source, which takes pterostilbene, amine compounds and paraformaldehyde as raw materials to prepare the benzoxazine, wherein the chemical reaction equation is as follows:
the structural formula of the amine compound is R-NH 2 Is one of the following structures:
the method specifically comprises the following steps:
adding pterostilbene, amine compounds and paraformaldehyde into a flask, adding an organic solvent, reacting for 4-10 hours at 80-130 ℃, filtering reactants after stopping the reaction, washing the filtrate with water, steaming in a rotary manner, and drying to obtain a solid product, namely the pterostilbene-based benzoxazine resin.
The molar ratio of pterostilbene, amine compounds and paraformaldehyde is 1:1: 2-1: 1:3.
further, the optimal molar ratio of pterostilbene, amine compounds and paraformaldehyde is 1:1:2.2.
the organic solvent is one or a mixture of more of toluene, dimethylbenzene and dioxane.
Compared with the prior art, the invention has the advantages that:
the bio-based pterostilbene is used as a phenol source to synthesize the benzoxazine resin containing double bonds, so that the degree of solidification of benzoxazine ring opening can be improved. The benzoxazine has excellent thermal performance, mechanical performance and corrosion resistance, the curing peak temperature is 200-260 ℃, the benzoxazine resin based on pterostilbene is further cured and crosslinked to obtain the benzoxazine resin, and the carbon residue rate is 40-80% at the inert atmosphere of 800 ℃; the resin material after curing has excellent hydrophobicity and corrosion resistance, wherein the water contact angle is 100-140 degrees. The invention has simple synthesis process, high yield and lower equipment requirement, and is suitable for large-scale production.
Drawings
FIG. 1 shows a nuclear magnetic resonance hydrogen spectrum of a benzoxazine resin obtained in example 1;
FIG. 2 is an infrared spectrum of a benzoxazine resin obtained in example 1;
FIG. 3 DSC profile of benzoxazine resin obtained in example 1;
FIG. 4 TGA spectrum of the cured benzoxazine resin material obtained in example 1.
Fig. 5 is a graph of the contact angle of water on a benzoxazine resin coating obtained in example 1.
Detailed Description
Specific embodiments of a pterostilbene-based benzoxazine resin and a preparation method thereof are provided below. It is necessary to point out that: the following examples are provided only to illustrate the present invention in more detail and are not intended to limit the scope of the invention. Modifications and adaptations of this invention, which do not depart from its spirit, are intended to be within the scope of the invention as claimed.
Example 1
2-furanmethanamine was used as an amine source. 1g (0.0039 mol) of pterostilbene, 0.379g (0.0039 mol) of 2-furanmethanamine, 0.258g (0.0086 mol) of paraformaldehyde are added to a flask, 50ml of toluene solution is added, a condenser is connected, and stirring and reaction are carried out at 120℃for 7 hours. After stopping the reaction, the reaction mixture was filtered, the filtrate was washed with water for 3 times and then rotary distilled, and dried in a vacuum oven at 50℃for one day to give 1.29g of benzoxazine monomer in 79% yield. The chemical reaction equation is as follows:
in this example, the structure of the oxazine product obtained was:
the nuclear magnetic resonance hydrogen spectrogram, fourier infrared transformation spectrogram, DSC graph, thermal weight loss graph and coating and water contact angle graph of the product are shown in figure 1, figure 2, figure 3, figure 4 and figure 5.
FIG. 1 shows a nuclear magnetic resonance hydrogen spectrum. The chemical shifts of about 4.93ppm and 4.03ppm are characteristic peaks of methylene on the oxazine ring. FIG. 2 is an infrared spectrum of 925cm -1 And 1231cm -1 Is the characteristic absorption peak of the benzoxazine ring. Fig. 3 is a DSC profile with a benzoxazine monomer cure exotherm peak temperature of 242 ℃. Fig. 4 is a TGA profile of the cured resin material, showing that the benzoxazine resin has a temperature of 381 ℃ at 5% thermal weight loss and a carbon residue of 56% at 800 ℃. Fig. 5 is a graph of water contact angle on a benzoxazine resin coating, with a contact angle of 109 °.
Example 2
The amine source compound 2-furanmethanamine in example 1 was replaced with aniline. The other steps are the same as those in example 1.
Wherein the specific chemical structural formula of the aniline is as follows:the amount of reactants was changed to: 1g (0.0039 mol) of pterostilbene, 0.364g (0.0039 mol) of aniline, 0.258g (0.0086 mol) of paraformaldehyde and 84% of yield were weighed.
The peak temperature of the latent curing benzoxazine resin monomer curing exotherm obtained in the embodiment is 244 ℃, the temperature of the benzoxazine resin after further curing crosslinking is 372 ℃ when the thermal weight loss is 5%, the carbon residue rate is 55% when the inert gas atmosphere is 800 ℃, and the contact angle between the resin coating and water is 115 degrees.
Example 3
The amine source compound 2-furanmethanamine in example 1 was replaced with 4-methylaniline. The other steps are the same as those in example 1.
Wherein the specific chemical structural formula of the 4-methylaniline is as follows:the amount of reactants was changed to: 1g (0.0039 mol) of pterostilbene, 0.418g (0.0039 mol) of 4-methylaniline and 0.258g (0.0086 mol) of paraformaldehyde are weighed. The yield thereof was found to be 85%.
The peak temperature of the latent curing benzoxazine resin monomer curing exotherm obtained in the embodiment is 250 ℃, the temperature of the benzoxazine resin after further curing crosslinking is 374 ℃ when the thermal weight loss is 5%, the carbon residue rate is 52% when the inert gas atmosphere is 800 ℃, and the contact angle between the resin coating and water is 119 °.
Example 4
The amine source compound 2-furanmethanamine in example 1 was replaced with octadecyl amine. The other steps are the same as those in example 1.
The specific chemical structural formula of the octadecyl fatty amine is as follows:the amount of reactants was changed to: 1g (0.0039 mol) of pterostilbene, 1.052g (0.0039 mol) of stearylamine and 0.258g (0.0086 mol) of paraformaldehyde are weighed. The yield thereof was found to be 83%.
The latent curing benzoxazine resin monomer obtained in this example has a curing exothermic peak temperature of 255 ℃, and after further curing and crosslinking, the temperature of the benzoxazine resin at 5% thermal weight loss is 312 ℃, the carbon residue rate at 800 ℃ in inert gas atmosphere is 46%, and the contact angle between the resin coating and water is 138 °.
Claims (7)
1. A pterostilbene-based benzoxazine resin, which is characterized in that: the molecular formula is as follows:
wherein,is one of the following structures:
2. the pterostilbene-based benzoxazine resin according to claim 1, wherein the curing peak temperature is 200-260 ℃, the pterostilbene-based benzoxazine resin is further cured and crosslinked to obtain the polybenzoxazine resin, and the carbon residue rate is 40-80% at 800 ℃ in an inert atmosphere; the water contact angle of the cured resin material is 100-140 degrees.
3. The preparation method of pterostilbene-based benzoxazine resin according to claim 1, which is characterized by comprising the following steps:
adding pterostilbene, amine compounds and paraformaldehyde into a flask, adding an organic solvent, reacting for 4-10 hours at 80-130 ℃, filtering reactants after stopping the reaction, washing the filtrate with water, steaming in a rotary manner, and drying to obtain a solid product, namely the pterostilbene-based benzoxazine resin.
4. The method for preparing pterostilbene-based benzoxazine resin according to claim 3, wherein the structural formula of the amine compound is R-NH 2 Is one of the following structures:
5. the method for preparing the pterostilbene-based benzoxazine resin according to claim 3, wherein the molar ratio of pterostilbene, amine compounds and paraformaldehyde is 1:1: 2-1: 1:3.
6. the preparation method of the pterostilbene-based benzoxazine resin according to claim 5, wherein the molar ratio of pterostilbene to amine compound to paraformaldehyde is 1:1:2.2.
7. the method for preparing pterostilbene-based benzoxazine resin according to claim 3, wherein the organic solvent is one or a mixture of several of toluene, xylene and dioxane.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103402963A (en) * | 2010-12-06 | 2013-11-20 | 赛泽恩有限公司 | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
| CN110240684A (en) * | 2019-05-29 | 2019-09-17 | 江苏大学 | A kind of latent curing type benzoxazine resin and preparation method thereof |
| CN110951018A (en) * | 2019-12-30 | 2020-04-03 | 江苏大学 | Apigenin-based bio-based benzoxazine resin and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103402963A (en) * | 2010-12-06 | 2013-11-20 | 赛泽恩有限公司 | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
| CN110240684A (en) * | 2019-05-29 | 2019-09-17 | 江苏大学 | A kind of latent curing type benzoxazine resin and preparation method thereof |
| CN110951018A (en) * | 2019-12-30 | 2020-04-03 | 江苏大学 | Apigenin-based bio-based benzoxazine resin and preparation method thereof |
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