CN113121772A - Pterostilbene benzoxazine-based resin and preparation method thereof - Google Patents
Pterostilbene benzoxazine-based resin and preparation method thereof Download PDFInfo
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- CN113121772A CN113121772A CN202110330558.6A CN202110330558A CN113121772A CN 113121772 A CN113121772 A CN 113121772A CN 202110330558 A CN202110330558 A CN 202110330558A CN 113121772 A CN113121772 A CN 113121772A
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- 229920005989 resin Polymers 0.000 title claims abstract description 65
- 239000011347 resin Substances 0.000 title claims abstract description 65
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 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 40
- 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 40
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000004132 cross linking Methods 0.000 claims abstract description 6
- 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
- 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
- -1 amine compound Chemical class 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 abstract description 9
- 238000005260 corrosion Methods 0.000 abstract description 9
- 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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 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
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical group CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 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
- 238000005303 weighing 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 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
- 239000005011 phenolic resin Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000004100 electronic packaging Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 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
- 239000002861 polymer material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000779 smoke Substances 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
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- 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
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- 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
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- 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 pterostilbene-based benzoxazine resin and a preparation method thereof, in particular to 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 the pterostilbene can further improve the crosslinking density of the benzoxazine through high-temperature reaction; the pterostilbene has the molecular structure characteristic, so that the coating has a hydrophobic effect and can well play a role in corrosion resistance; the synthesis steps are simple, and the yield is high; and the cured benzoxazine resin has excellent thermal and mechanical properties and corrosion resistance. The synthesis process is simple, has low requirements on equipment, and is suitable for large-scale production.
Description
Technical Field
The invention belongs to the technical field of thermosetting resin, and particularly relates to pterostilbene-based benzoxazine resin and a preparation method thereof.
Background
The benzoxazine resin is a novel ring-opening polymerization phenolic resin, can generate a structure similar to a phenolic resin through ring-opening polymerization, and has the advantages of wide raw material source, simple preparation, excellent performance, no volatile matter during curing, low porosity and shrinkage rate of products and the like. The product has excellent mechanical property, heat resistance, electric insulation property, dimensional stability, molding processability, flame retardance and low smoke, and has the most outstanding advantages of very flexible molecular designability and capability of designing the molecular structure by changing the amine source and the phenol source compounds. Benzoxazine resin and composite resin using the benzoxazine resin as a matrix are widely applied to some molding processing technologies; and the material can be used in the related fields of burning-resistant materials, corrosion-resistant materials, electronic packaging materials, parts in the mechanical manufacturing industry, aerospace materials, adhesives, circuit board substrates, vacuum pump rotary sheets, insulating materials and the like.
With the expansion of the application field, people pursue high-performance polybenzoxazine materials, and meanwhile, environmental influence also becomes a key consideration factor. The development of materials with both high performance and environmental friendliness has become the direction of researchers and researchers in the industry. The bio-based benzoxazine resin containing double bond active functional groups prepared by the patent number (CN107459512A) does not have good corrosion resistance and can be prepared for several days, so that the production cost is high. The patent No. (CN106674214A) uses a three-step method to synthesize the furyldiamide type benzoxazine resin, and the reaction process is complicated and is not suitable for large-scale production. Due to the rapid development of current high polymer materials, people have higher and higher requirements on high-performance resin matrixes. The performance of benzoxazine resin needs to be further improved to meet the wide application in various fields, such as improving the heat resistance, hydrophobicity and the like, so that the benzoxazine resin can be used in high-temperature and corrosive environments.
Disclosure of Invention
In view of some defects of the existing thermosetting resin materials, the invention takes the bio-based pterostilbene as a phenol source, thereby not only reducing the pollution to the environment from the raw materials, but also increasing the crosslinking degree of the cured resin by the carbon-carbon double bond contained in the pterostilbene and improving the mechanical property of the cured resin, and the benzoxazine resin prepared from the pterostilbene has good hydrophobic effect after curing because the molecular structure of the pterostilbene contains methoxyl, and can well play a role in corrosion resistance. In addition, the resin has simple synthesis process, high yield and low requirement on equipment, and is suitable for large-scale production.
The invention aims to provide novel benzoxazine taking bio-based pterostilbene as a phenol source and a preparation method thereof, wherein the bio-based pterostilbene benzoxazine resin is prepared, so that the curing temperature of the benzoxazine resin is greatly reduced, and the good thermal property, mechanical property and corrosion resistance of the resin are kept.
The purpose of the invention is realized by the following technical scheme:
one of the purposes of the invention is to provide a pterostilbene benzoxazine-based resin, the molecular chemical structural formula of which is shown as follows:
wherein the content of the first and second substances,
is one of the following structures:
according to the pterostilbene-based benzoxazine resin prepared by the preparation method disclosed by the invention, 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 the inert atmosphere of 800 ℃; the cured resin material 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 benzoxazine resin with bio-based pterostilbene as a phenol source, wherein the benzoxazine is prepared by taking pterostilbene, an amine compound and paraformaldehyde as raw materials, and the chemical reaction equation is as follows:
the structural formula of the amine compound is R-NH2Is one of the following structures:
the method specifically comprises the following steps:
adding the pterostilbene, the amine compound and the paraformaldehyde into a flask, adding an organic solvent, reacting for 4-10 hours at 80-130 ℃, filtering reactants after the reaction is stopped, washing the filtrate with water, performing rotary evaporation, and drying to obtain a solid product, namely the pterostilbene-based benzoxazine resin.
The mol ratio of the pterostilbene to the amine compound to the paraformaldehyde is 1: 1: 2-1: 1: 3.
further, the optimal molar ratio of the pterostilbene to the amine compound to the paraformaldehyde is 1: 1: 2.2.
the organic solvent is one or a mixture of several of toluene, xylene 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 curing degree of the ring opening of the benzoxazine can be improved. The benzoxazine has excellent thermal property, mechanical property and corrosion resistance, the curing peak temperature is 200-260 ℃, the polybenzoxazine resin is obtained after the polybenzoxazine resin is further cured and crosslinked, and the carbon residue rate is 40-80% at the inert atmosphere of 800 ℃; the cured resin material has excellent hydrophobicity and corrosion resistance, wherein the water contact angle is 100-140 degrees. The invention has simple synthesis process, high yield and low requirement on equipment, and is suitable for large-scale production.
Drawings
FIG. 1 nuclear magnetic resonance hydrogen spectrum of benzoxazine resin obtained in example 1;
FIG. 2 is an infrared spectrum of the benzoxazine resin obtained in example 1;
FIG. 3 DSC spectrum of benzoxazine resin obtained in example 1;
FIG. 4 TGA spectrum of cured benzoxazine resin obtained in example 1.
FIG. 5 contact angle diagram of water on the benzoxazine resin coating obtained in example 1.
Detailed Description
The following provides a specific embodiment of the pterostilbene-based benzoxazine resin and the preparation method thereof. It is to be noted that: the following examples are intended only to illustrate the present invention in more detail, and do not narrow the scope of the present invention. Modifications and adaptations of the present invention may occur to those skilled in the art after reading the present invention and may be made without departing from the spirit and scope of the present invention as defined by the appended claims.
Example 1
2-furanmethanamine is used as an amine source. 1g (0.0039mol) of pterostilbene, 0.379g (0.0039mol) of 2-furanmethanamine, and 0.258g (0.0086mol) of paraformaldehyde were added to a flask, 50ml of a toluene solution was added, a condenser tube was connected, and stirring and reaction were carried out at 120 ℃ for 7 hours. After the reaction was stopped, the reaction product was filtered, and the filtrate was washed with water for 3 times, then rotary-evaporated, and dried in a vacuum oven at 50 ℃ for one day to obtain 1.29g of benzoxazine monomer with a yield of 79%. The chemical reaction equation is as follows:
in this example, the structure of the obtained oxazine product is:
the nuclear magnetic resonance hydrogen spectrogram, Fourier infrared transform spectrogram, DSC curve chart, thermogravimetry curve chart and coating and water contact angle chart of the product are shown in figure 1, figure 2, figure 3, figure 4 and figure 5.
FIG. 1 shows a NMR chart. 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-1And 1231cm-1The position is a characteristic absorption peak of the benzoxazine ring. FIG. 3 is a DSC graph showing that the peak temperature of the benzoxazine monomer curing exotherm is 242 ℃. FIG. 4 is a TGA graph of the cured resin material, and it can be seen that the temperature of the benzoxazine resin with 5% thermal weight loss is 381 ℃, and the carbon residue rate at 800 ℃ is 56%. Fig. 5 shows the water contact angle on the benzoxazine resin coating at 109 °.
Example 2
The amine source compound 2-furanmethanamine in example 1 was replaced with aniline. The other steps were the same as in example 1.
Wherein the specific chemical structural formula of the aniline is as follows:
the amounts of reactants were changed to: weighing 1g (0.0039mol) of pterostilbene, 0.364g (0.0039mol) of aniline and 0.258g (0.0086mol) of paraformaldehyde, wherein the yield is 84%.
The exothermic peak temperature of the latent curing type benzoxazine resin monomer obtained in the embodiment is 244 ℃, after further curing and crosslinking, the polybenzoxazine resin has a temperature of 372 ℃ when the thermal weight loss is 5%, a carbon residue rate of 55% when the resin is in an inert gas atmosphere of 800 ℃, and a contact angle between the resin coating and water of 115 °.
Example 3
The amine source compound 2-furanmethanamine in example 1 was replaced with 4-methylaniline. The other steps were the same as in example 1.
Wherein the specific chemical structural formula of the 4-methylaniline is as follows:
the amounts of reactants were changed to: weighing 1g (0.0039mol) of pterostilbene, 0.418g (0.0039mol) of 4-methylaniline and 0.258g (0.0086mol) of paraformaldehyde. The yield thereof was found to be 85%.
The latent curing type benzoxazine resin monomer obtained in the embodiment has a curing exothermic peak temperature of 250 ℃, and after further curing and crosslinking, the polybenzoxazine resin has a temperature of 374% when the thermal weight loss is 5%, a carbon residue rate of 52% when the temperature is 800 ℃ in an inert gas atmosphere, and a contact angle between a resin coating and water of 119 °.
Example 4
The amine source compound 2-furanmethanamine in example 1 was replaced with octadecylamine. The other steps were the same as in example 1.
The specific chemical structural formula of the octadecyl amine is as follows:
the amounts of reactants were changed to: weighing 1g (0.0039mol) of pterostilbene, 1.052g (0.0039mol) of octadecylamine and 0.258g (0.0086mol) of paraformaldehyde. The yield thereof was found to be 83%.
The latent curing type benzoxazine resin monomer obtained in the embodiment has a curing exothermic peak temperature of 255 ℃, and after further curing and crosslinking, the polybenzoxazine resin has a temperature of 312 ℃ when the thermal weight loss is 5%, a carbon residue rate of 46% when the resin is in an inert gas atmosphere of 800 ℃, and a contact angle between a resin coating and water of 138 °.
Claims (7)
1. A pterostilbene benzoxazine resin is characterized in that: the molecular formula is as follows:
wherein the content of the first and second substances,
is one of the following structures:
2. the pterostilbene benzoxazine-based resin according to claim 1, wherein the curing peak temperature is 200-260 ℃, the further curing and crosslinking of the pterostilbene benzoxazine-based resin results in a polybenzoxazine resin, and the char yield is 40-80% at 800 ℃ in an inert atmosphere; the water contact angle of the cured resin material is 100-140 degrees.
3. The method for preparing pterostilbene benzoxazine-based resin according to claim 1, specifically comprising the following steps:
adding the pterostilbene, the amine compound and the paraformaldehyde into a flask, adding an organic solvent, reacting for 4-10 hours at 80-130 ℃, filtering reactants after the reaction is stopped, washing the filtrate with water, performing rotary evaporation, and drying to obtain a solid product, namely the pterostilbene-based benzoxazine resin.
4. The method for preparing pterostilbene benzoxazine-based resin according to claim 3, wherein the amine compound has a structural formula of R-NH2Is one of the following structures:
5. the method for preparing pterostilbene benzoxazine-based resin according to claim 3, wherein the molar ratio of the pterostilbene to the amine compound to the paraformaldehyde is 1: 1: 2-1: 1: 3.
6. the method for preparing pterostilbene benzoxazine-based resin according to claim 5, wherein the molar ratio of the pterostilbene to the amine compound to the paraformaldehyde is 1: 1: 2.2.
7. the method for preparing pterostilbene benzoxazine-based resin according to claim 3, wherein the organic solvent is one or a mixture of toluene, xylene and dioxane.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114907536A (en) * | 2022-05-06 | 2022-08-16 | 镇江利德尔复合材料有限公司 | Multifunctional benzoxazine resin and preparation method thereof |
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|---|---|---|---|---|
| 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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Patent Citations (3)
| 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114907536A (en) * | 2022-05-06 | 2022-08-16 | 镇江利德尔复合材料有限公司 | Multifunctional benzoxazine resin and preparation method thereof |
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