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Preparation of low-shrinkage UPy-ionic liquid mixed type photocuring monomer

A light-curing monomer and ionic liquid technology, applied in the field of light-curing, can solve the problems of poor compatibility with light-curing monomers and initiators, hindering application, etc. easy precipitation effect

Inactive Publication Date: 2019-06-14
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the strong inter-molecular and intra-molecular hydrogen bonds of the UPy group, it has the characteristics of being insoluble and insoluble in most solvents, resulting in poor compatibility with photocurable monomers and initiators, which seriously hinders its application.

Method used

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  • Preparation of low-shrinkage UPy-ionic liquid mixed type photocuring monomer
  • Preparation of low-shrinkage UPy-ionic liquid mixed type photocuring monomer
  • Preparation of low-shrinkage UPy-ionic liquid mixed type photocuring monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A kind of preparation of low-shrinkage UPy ionic liquid mixed type photocurable monomer, the preparation method of this mixed monomer comprises the steps:

[0040] (1) Preparation method of UPy monomer

[0041] ①Heat 1.25g 6-methylisocytosine and 25g DMSO at 150°C for 0.8h, stir to form a clear solution;

[0042] ② Then in N 2 Under protective conditions, slowly add 1.31g of isocyanoethyl methacrylate dropwise, and stir at 20°C for 0.5h; then put the reaction bottle into an ice-water bath to terminate the reaction, and a lot of white solids will be produced;

[0043] ③Finally wash 3 times with acetone to remove the remaining reactants and solvent, and filter and dry to obtain powdered 2-(3-(6-methyl-4-oxo-1,4-dihydropyrimidine ) ureido) ethyl methacrylate. Its NMR spectrum is as figure 1 As shown, its hydrogen bond network diagram is shown in figure 2 shown.

[0044] (2) Preparation of double bond-containing ionic liquid

[0045] ① First, mix 4.10g 1-methylimida...

Embodiment 2

[0054] A kind of preparation of low-shrinkage UPy ionic liquid mixed type photocurable monomer, the preparation method of this mixed monomer comprises the steps:

[0055] (1) Preparation method of UPy monomer

[0056] ①Heat 1.25g 6-methylisocytosine and 31.25g DMSO at 135°C for 0.6h, stir to form a clear solution;

[0057] ② Then in N 2 Under protective conditions, 2.13 g of isocyanobutyl ethacrylate was slowly added dropwise, and the reaction was stirred at 30°C for 0.8 h; then the reaction bottle was placed in an ice-water bath to terminate the reaction, and a lot of white solids would be produced.

[0058] ③Finally wash with acetone 4 times to remove residual reactant and solvent, and filter and dry to obtain powdered (2-(3-(6-methyl-4-oxo-1,4-dihydro pyrimidine) ureido) butyl ethyl acrylate.

[0059] (2) Preparation of double bond-containing ionic liquid

[0060] ①First, mix 4.80g 1-ethylimidazole with 14.43g 6-bromo-n-hexanol, N 2 Under protective conditions, stir an...

Embodiment 3

[0069] A kind of preparation of low-shrinkage UPy ionic liquid mixed type photocurable monomer, the preparation method of this mixed monomer comprises the steps:

[0070] (1) Preparation method of UPy monomer

[0071] ①Heat 1.25g 6-methylisocytosine and 37.5g DMSO at 140°C for 0.45h, stir to form a clear solution;

[0072] ② Then in N 2 Under protective conditions, 2.01 g of isocyanobutyl methacrylate was slowly added dropwise, and the reaction was stirred at 35°C for 1 h; then the reaction bottle was put into an ice-water bath to terminate the reaction, and a lot of white solids would be produced.

[0073] ③Finally wash 5 times with acetone to remove residual reactant and solvent, and filter and dry to obtain powdered (2-(3-(6-methyl-4-oxo-1,4-dihydro pyrimidine) ureido) butyl methacrylate.

[0074] (2) Preparation of double bond-containing ionic liquid

[0075] ① First, mix 5.60g 1-propylimidazole with 20.39g 6-iodo-n-hexanol, N 2 Under protective conditions, stir and r...

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Abstract

The invention discloses preparation of a low-shrinkage UPy-ionic liquid mixed type photocuring monomer. The preparation comprises the following steps: (1) firstly performing an addition reaction on 6methyl-isocytosine and NCO (Isocyanate group) substituted acrylic acid to synthesize a UPy monomer containing acrylic acid double bonds; (2) secondly, performing a reaction on imidazole, chlorohydrinand acryloyl chloride to synthesize ionic liquid containing acrylic acid double bonds; and (3) uniformly mixing the UPy monomer and the ionic liquid, and using a mixture as a mixed monomer to be mixedwith resin to obtain a photocuring coating with relatively low shrinkage rate.

Description

technical field [0001] The invention relates to the field of photocuring, in particular to the preparation of a low-shrinkage UPy-ionic liquid mixed photocuring monomer. Background technique [0002] Due to its fast polymerization speed and mild polymerization conditions, UV curing technology has unique "5E" characteristics of high efficiency, wide adaptability, economy, energy saving, and environmental friendliness. It has been widely used in many fields such as coatings, inks, adhesives, and printing plates. application. However, no technology is perfect. During the photocuring process, the molecular distance between monomers or oligomers will quickly change from remote van der Waals force to near-state covalent bond force, resulting in a reduction in volume. Due to its fast polymerization speed, the molecular chain cannot be fully stretched, and the stress cannot be released, which will cause serious volume shrinkage and affect the use of the material. [0003] As a typ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47C07D233/60C08F220/36
Inventor 袁妍李聪董延茂
Owner SUZHOU UNIV OF SCI & TECH
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