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Method for preparing all-bio-based photocuring activated monomer and application of all-bio-based photocuring activated monomer

A technology of photoactive monomers and active monomers, which is applied in the field of preparation of all bio-based photocurable active monomers, can solve the problems of low renewable carbon content and lack of coating film performance, and achieve high reactivity, improved performance, The effect of alleviating dependence

Inactive Publication Date: 2015-10-28
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the limitation of the types and structural characteristics of the renewable resources used, the renewable carbon content of bio-based prepolymers and monomers is low and the coating performance is lacking.

Method used

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  • Method for preparing all-bio-based photocuring activated monomer and application of all-bio-based photocuring activated monomer
  • Method for preparing all-bio-based photocuring activated monomer and application of all-bio-based photocuring activated monomer
  • Method for preparing all-bio-based photocuring activated monomer and application of all-bio-based photocuring activated monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] 1) Put 8g of vanillin, 110mL of tetrahydrofuran and 50mL of water into a two-necked bottle, fill it with nitrogen to protect, add 9.6g of sodium carbonate; react at room temperature for 5 hours, then add 0.1mol / L dilute hydrochloric acid to neutralize to PH=3 , THF was removed by rotary evaporation; the aqueous phase was extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous sodium sulfate, filtered by suction and rotary evaporated to obtain vanillin-based diol.

[0019] 2) Put 2.0 g of vanillin-based diol, 4.3 g of triethylamine, and 10 g of ethyl acetate in a 100 mL flask, and add 8.6 g of undecylenyl chloride dropwise into the flask with a constant pressure dropping funnel under an ice bath. The reaction was first reacted in an ice bath for 2 hours, then warmed up to room temperature and reacted for 24 hours, filtered with suction, the liquid phase was washed with 1% aqueous sodium hydroxide solution and distilled water, dried w...

Embodiment 2

[0023] Take 2g of cardanol, 1g of triethylamine and 10g of ethyl acetate respectively in a 100mL flask, and add 2g of undecylenoyl chloride dropwise into the flask with a constant pressure dropping funnel under ice bath. The reaction was first reacted in an ice bath for 2 hours, then warmed up to room temperature and reacted for 24 hours, filtered with suction, and the liquid phase was washed with 1% aqueous sodium hydroxide solution and distilled water, dried with anhydrous magnesium sulfate, filtered with suction and rotary steamed to obtain cashew nuts Phenolic reactive monomers. (yield: 87%)

[0024] 1 H NMR (400MHz, CDCl 3 )δ7.30(s,1H),7.07(s,1H),6.92(s,2H),5.84(td,J=16.8,6.9Hz,2H),5.39(s,2H),5.00(s,4H ), 2.59(s,4H), 2.30(s,2H), 2.07(s,4H), 1.78(s,2H), 1.64(s,4H), 1.34(s,28H), 0.91(s,2H).

[0025] 13 C NMR (101MHz, CDCl 3 )δ171.13 (COO), 149.70 (C), 143.90 (C), 138.12 (CH 2 =CH),129.23(CH),128.92(CH),128.03(CH),124.76(CH),120.37(CH),117.68(CH 2 =CH),113.14(CH 2 =...

Embodiment 3

[0027] Take 1.0 g of gallic acid, 5.4 g of undecylenoyl chloride and 10 g of acetone in a 100 mL flask, and add 2.7 g of triethylamine dropwise into the flask with a constant pressure dropping funnel under ice-cooling. The reaction was first reacted in ice bath for 2h, then warmed up to room temperature and reacted for 24h, filtered with suction, and the acetone solvent was removed by rotary evaporation, and ethyl acetate was used as the solvent instead. Then wash with 1% aqueous sodium hydroxide solution and distilled water respectively, dry with anhydrous magnesium sulfate, filter with suction and rotary evaporate to obtain gallic acid-based active monomer. (yield: 78%)

[0028] 1 H NMR (400MHz, Acetone-D 6 )δ7.68(s,2H),5.68(s,3H),4.83(s,6H),3.44(s,3H),2.46(s,4H),2.14(s,2H),1.91(s,8H ),1.58(s,6H),1.22(s,32H),0.99(s,6H).

[0029] 13 C NMR (101MHz, Acetone-D 6 )δ170.28 (COO), 168.93 (COOH), 143.22 (C), 139.71 (CH 2 =CH), 138.93(C), 122.09(C), 118.11(CH), 113.84(CH 2 =C...

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Abstract

The invention discloses a method for preparing an all-bio-based photocuring activated monomer and an application of the all-bio-based photocuring activated monomer. The preparation method includes the steps that a bio-based hydroxyl compound containing stiffness rings or a modified bio-based hydroxyl compound containing stiffness rings, triethylamine and solvent are mixed, undecylenylacyl chloride is dripped slowly under the ice-bath condition, the temperature is rise to an indoor temperature to further react for 12-36 hours after reacting is conducted for 2-4 hours, suction filtration, liquid phase washing, drying, suction filtration and rotary evaporateion are carried out, and accordingly the all-bio-based photocuring activated monomer is obtained. According to the application of the all-bio-based photocuring activated monomer, 5-40 parts of all-bio-based photocuring activated monomer, 100 parts of all-vegetable-oil-based polyenoid photocuring prepolymer, 10-60 parts of multi-mercapto compound and 2-8 parts of UV-light 1173 photoinitiator, by weight, are evenly mixed, and then an all-bio-based ultraviolet curing coating is obtained. Double bonds contained in the all-bio-based photocuring activated monomer prepared through the method are located at the end positions, so that the reactivity is high. The content of renewable carbon atoms is 100%, and thus dependence on oil resources is relieved.

Description

technical field [0001] The invention relates to a bio-based polymer material, in particular to a preparation method and application of an all-bio-based photocurable active monomer. Background technique [0002] UV curing technology has the advantages of fast curing speed, high production efficiency, less pollution and energy saving, and is an environmentally friendly green technology. UV-curable coatings are mainly composed of photoactive oligomers, reactive monomers and photoinitiators. At this stage, the starting materials of UV-curable formulations are all petrochemical products. In the case of depletion of petroleum resources and rising prices, it is of great basic research and economic significance to develop new UV-curable coatings using renewable resources as raw materials. Biomass raw materials can be regenerated through photosynthesis, the growth cycle is short, cheap, and biomass-based polymers are biodegradable and environmentally friendly. [0003] The current ...

Claims

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Application Information

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IPC IPC(8): C07C69/533C07C67/14C07D493/04C09D163/10
CPCC07C67/14C07C2601/14C07D493/04C09D163/10C07C69/533
Inventor 付长清申亮程烈
Owner JIANGXI SCI & TECH NORMAL UNIV
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