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Itaconic acid diester type photocuring monomer, composition, preparation method and application

A technology of itaconate diester and light-curing monomer, which is applied in the preparation of organic compounds, carboxylic acid ester preparation, chemical instruments and methods, etc., to achieve low volatility, good mutual solubility and copolymerization ability, and strong application prospects Effect

Active Publication Date: 2022-04-19
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The formation of diesters of itaconic acid containing double bonds and alkenes with dialkyl groups has not been reported

Method used

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  • Itaconic acid diester type photocuring monomer, composition, preparation method and application
  • Itaconic acid diester type photocuring monomer, composition, preparation method and application
  • Itaconic acid diester type photocuring monomer, composition, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: Utilize 3-bromo-2-methylpropene to prepare target product monomer (I)-1

[0043]

[0044] Add 26.0 grams (0.2mol) of itaconic acid, 55.2 grams (0.4mol) of potassium carbonate and 250 milliliters of DMF into a 500ml three-necked flask, then add 0.01mol of hydroquinone for polymerization inhibition, heat to 70°C, and stir for 30 minutes. 53.6 g (0.4 mol) of 3-bromo-2-methylpropene was added dropwise into the reaction system, stirring was continued for 12 hours, and the reaction was monitored by TLC to complete. Inorganic salts were filtered off and most of the organic solvents were distilled off. Dichloromethane, extracted with deionized water, dried, evaporated to dryness, and distilled under reduced pressure to obtain 40.7 g of the product. Yield 85.5%. GC monitored purity 99%.

[0045] 1 H NMR (CDCl 3 ,400MHz),δ6.38(s,1H,=CH 2 ),5.75(s,1H,=CH 2 ),4.97(d,1H,=CH 2 ),4.92(d,2H,=CH 2 ),4.58(s,2H,CH 2 ),4.51(s,2H,CH 2 ),3.41(s,2H,CH 2 ),1.76(s,3...

Embodiment 2

[0047] Embodiment 2: Utilize 2-methallyl alcohol to prepare target product monomer (I)-1

[0048]

[0049] Add 26.0 grams (0.2mol) of itaconic acid and 250 milliliters of toluene in a 500 milliliter three-necked flask, then add 0.01mol hydroquinone as a polymerization inhibitor, add a reflux condenser and a water separator, and add 34.6 grams dropwise under heating and reflux (0.48mol) 2-methallyl alcohol into the reaction system, continue to reflux for 12 hours, TLC monitors the end of the reaction. Washed three times with deionized water, dried over anhydrous sodium sulfate, rotary evaporated toluene and excess 2-methallyl alcohol, and vacuum distilled to obtain 42.7 g of the target product. Yield 89.7%. GC monitored purity 99%.

Embodiment 3

[0050] Embodiment 3: Utilize 3-methyl-3-buten-1-alcohol to prepare target product body (I)-2

[0051]

[0052] Add 26.0 grams (0.2mol) of itaconic acid and 250 milliliters of toluene in a 500 milliliter three-necked flask, then add 0.01mol hydroquinone as a polymerization inhibitor, add a reflux condenser and a water separator, and add 41.3 grams dropwise under heating and reflux (0.48mol) 3-methyl-3-buten-1-ol into the reaction system, and continued to reflux for 18 hours, and TLC monitored the end of the reaction. Washed three times with deionized water, dried over anhydrous sodium sulfate, rotary evaporated toluene and excess 3-methyl-3-buten-1-ol, and vacuum distilled to obtain 45.5 g of the target product. Yield 85.6%. GC monitored purity 99%.

[0053] HR-MS (C 15 h 22 o 4 ): m / e: 266.15; Experimental result: 267.16 (M+H + ).

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Abstract

The invention relates to an itaconic acid diester type photocuring monomer, a composition, a preparation method and application. The molecular structure of the itaconic acid diester type photocuring monomer is shown as a formula (I), R1 and R3 independently represent any group selected from hydrogen atoms, alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, aryl and aralkyl, R2 and R4 independently represent any group selected from alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, aryl and aralkyl, and R1 and R2 independently represent any group selected from alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms, aryl and aralkyl. And X and Y each independently represent an empty chain alkyl group having 1-12 carbon atoms. The monomer at least contains three or more unsaturated groups, is biomass-sourced, and is simple and convenient to synthesize. The composition is composed of various specific monomers in the general formula (I), multifunctional compounds except the compounds, a photoinitiator, an auxiliary agent and the like. The composition enables a photocuring reaction to fully occur even in an air atmosphere, and has excellent curing performance. Wide application prospects are realized in the fields of photocuring coatings and the like.

Description

technical field [0001] The invention belongs to the technical field of new material organic chemicals, in particular to a photocurable monomer with itaconate diester, the ester further contains unsaturated groups, its preparation method, composition and application, especially in Application in the field of UV-LED light curing materials. Background technique [0002] Photocuring technology is a process in which liquid photosensitive resins are polymerized into solids under light induction. It has the characteristics of high efficiency, rapidity, economy, energy saving, and environmental protection. It is widely used in adhesives, photocurable coatings and inks, photoresists, and 3D microstructures. , biomedicine and other fields. Photocurable monomer is the key factor controlling the performance of the entire cured product, and its activity and dilution directly affect the photocuring rate, degree of curing and end product performance. In particular, radical curing is usua...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/593C07C67/11C07C67/08C08F222/14C09D4/02
CPCC07C69/593C07C67/11C07C67/08C08F222/14C09D4/00
Inventor 金明廖文
Owner TONGJI UNIV
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