Eugenol methacrylate, preparation method thereof, eugenol-based epoxy vegetable oil acrylate UV curing system and application of eugenol-based epoxy vegetable oil acrylate UV curing system

A clove methacrylate, eugenol-based epoxy technology, applied in the application, sulfide preparation, ink and other directions, can solve the problems of high production conditions, limited use of epoxy acrylates, poor biodegradability, etc. Improve anti-corrosion performance and tensile strength, reduce the time of light curing, and improve the effect of tensile strength

Pending Publication Date: 2022-07-12
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its slow photocuring rate, soft cured film, and poor mechanical properties, it has greatly hindered its application in products such as UV-curable coatings, UV-curable inks, and UV-curable adhesives.
And so far, epoxy acrylates in photocurable coatings are mostly derived from petroleum products. Due to the increasing shortage of petroleum resources and the poor biodegradability of petroleum-based epoxy acrylates, the application of epoxy acrylates in light is further limited. Use in cured coatings
[0003] In addition, the traditional production method of epoxy acrylate requires high production conditions and complicated operation, such as: the patent application of CN111217988A discloses a kind of preparation method of epoxy acrylate, including the following steps: step 1): by mass parts , put epoxy resin, acrylic resin, polymerization inhibitor, catalyst and antioxidant in the reaction kettle in turn, heat up to 40-50°C, stir until dissolved; step 2): slowly heat up to 75°C, stop heating, and naturally heat up Incubate at 90°C for 0.5h; step 3): heat up to 95°C for 1.5h; step 4): naturally heat up to 115-118°C for 1.0h, take samples to measure AV≤40mgKOH / g; step 5): cool down to 50°C , put in acid anhydride, heat up to 108-110°C, keep warm until AV≤4mgKOH / g is measured by sampling, then cool down and discharge

Method used

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  • Eugenol methacrylate, preparation method thereof, eugenol-based epoxy vegetable oil acrylate UV curing system and application of eugenol-based epoxy vegetable oil acrylate UV curing system
  • Eugenol methacrylate, preparation method thereof, eugenol-based epoxy vegetable oil acrylate UV curing system and application of eugenol-based epoxy vegetable oil acrylate UV curing system
  • Eugenol methacrylate, preparation method thereof, eugenol-based epoxy vegetable oil acrylate UV curing system and application of eugenol-based epoxy vegetable oil acrylate UV curing system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation method of eugenol methacrylate of the present implementation, comprises the steps:

[0044] (1) Add 16.42g eugenol (purity 99%), 8.59g 2-mercaptoethanol and 0.73g photoinitiator 2-hydroxy-2-methyl-1-phenyl-1-propanone (eugenol) into a quartz test tube The molar ratio with 2-mercaptoethanol is 1:1.1, and the amount of photoinitiator is 3% of the sum of the mass of eugenol and 2-mercaptoethanol), react for 6h under the irradiation of 365nm ultraviolet light, wash the reaction product three times, Then, it was dried with anhydrous magnesium sulfate to obtain eugenol polyol. The reaction scheme of this step is as follows figure 1 shown.

[0045](2) 10g of eugenol polyol obtained in step (1), 0.25g of 4-dimethylaminopyridine were added to the flask with a thermometer, then 15.90g of methacrylic anhydride was slowly added with a dropping funnel under an ice-water bath (The molar ratio of eugenol polyol and methacrylic anhydride is 1:2.5, and the amount of 4...

Embodiment 2

[0049] The preparation method of the epoxidized soybean oil acrylate of the present embodiment comprises the following steps:

[0050] In a three-necked flask with a thermometer, add 20.00g epoxidized soybean oil (ESO), 4.56g acrylic acid (AA) (purity 99%), 0.25g triphenylphosphine and 0.06g hydroquinone (epoxidized soybean oil and The molar ratio of acrylic acid is 1:3, the amount of triphenylphosphine is 1 wt % of the sum of the mass of epoxidized soybean oil and acrylic acid, and the amount of hydroquinone is 1 wt % of the mass of acrylic acid), mechanically stirred at 80 ° C for 0.5 wt % h, then the temperature was raised to 120 °C and the reaction was continued for 2 h to obtain epoxidized soybean oil acrylate (AESO). The reaction scheme of this step is as follows Figure 4 shown.

[0051] The Fourier transform infrared spectrogram of the epoxidized soybean oil of the present embodiment and the epoxidized soybean oil acrylate is as follows Figure 5 shown. from Figu...

Embodiment 3

[0054] The epoxidized soybean oil acrylate UV curing system of this embodiment includes the epoxidized soybean oil acrylate prepared according to the preparation method of Example 2 and the photoinitiator 2-hydroxy-2-methyl-1-phenyl-1- acetone. When preparing the photocurable film, 10 g of epoxidized soybean oil acrylate was used as a prepolymer, and then 0.3 g of photoinitiator 2-hydroxy-2-methyl-1-phenyl-1-propanone was added.

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Abstract

The invention belongs to the technical field of UV curing materials, and particularly relates to eugenol methacrylate and a preparation method thereof as well as an eugenol-based epoxy vegetable oil acrylate UV curing system and application of the eugenol-based epoxy vegetable oil acrylate UV curing system. Eugenol and 2-mercaptoethanol are used as raw materials, eugenol polyol is prepared through a thiol-ene light click reaction, then eugenol polyol and methacrylic anhydride are subjected to an esterification reaction, and methacrylic acid eugenol is synthesized. Then, epoxy vegetable oil and acrylic acid are subjected to a ring-opening reaction to prepare epoxy vegetable oil acrylate, methacrylic acid eugenol is used as a reactive diluent and is blended with the epoxy vegetable oil acrylate to prepare a film, and the eugenol-based epoxy vegetable oil acrylate light-cured film is obtained. A large number of benzene ring structures and double bonds are introduced into epoxy vegetable oil acrylic acid, the tensile strength of a cured film can be effectively improved, the light curing time is shortened, the corrosion resistance of the film is improved, and the crosslinking density is high.

Description

technical field [0001] The invention belongs to the technical field of UV curing materials, and in particular relates to a eugenol methacrylate and a preparation method thereof, a eugenol-based epoxy vegetable oil acrylate UV curing system and applications thereof. Background technique [0002] Epoxy acrylate is obtained by esterification of epoxy resin and (meth)acrylate. It has the characteristics of low price, good flexibility, strong adhesion, little skin irritation, especially excellent wetting and dispersing properties for pigments. , is currently the most widely used, the largest amount of photocurable oligomers. However, due to its slow light curing rate, soft cured film and poor mechanical properties, its application in UV-curable coatings, UV-curable inks, and UV-curable adhesives has been greatly hindered. And so far, most of the epoxy acrylates in photocurable coatings are derived from petroleum products. Due to the increasing shortage of petroleum resources and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/16C07C319/18C07C319/20C08F289/00C08F222/24C09D4/02C09D4/06C09J4/02C09J4/06C09D11/101B33Y70/00
CPCC07C323/16C07C319/18C07C319/20C08F289/00C09D4/06C09J4/06C09D11/101B33Y70/00C08F222/1025Y02P20/584
Inventor 杨卓鸿胡玲方亨廖芯榆
Owner SOUTH CHINA AGRI UNIV
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