Acrylate compound containing methyl sulfoxide structure, and preparation method and application thereof

A technology of acrylate and methyl sulfoxide, applied in the field of acrylate compound containing methyl sulfoxide structure and its preparation, can solve the problems of low volatility, affect the performance of cured film, difficult to disperse, etc., and achieve good solubility Effect

Active Publication Date: 2013-12-18
GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] With the continuous development of light-curing technology, more and more functional materials are combined into light-curing formulations. For example, antistatic light-curing coating systems use quaternary ammonium salts as moisturizing and antistatic agents, but quaternary ammonium salts are used in traditional light-curing It is basically dissolved in the formula, and it is difficult to disperse. It is necessary to use highly polar solvents to aid dissolution, such as DMSO, DMF, sulfolane, etc. contrary to the characteristics of
Moreover, the above-mentioned highly polar solvents do not participate in photo-crosslinking film formation, and most of them have low volatility, and may permeate and migrate if they remain in the photo-cured coating, which will affect the performance of the cured film.

Method used

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  • Acrylate compound containing methyl sulfoxide structure, and preparation method and application thereof
  • Acrylate compound containing methyl sulfoxide structure, and preparation method and application thereof
  • Acrylate compound containing methyl sulfoxide structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Take 81 g of 2-methylthioethyl acrylate and place it in a 500 ml round bottom flask, add 80 ml of hydrogen peroxide with a mass concentration of 30%, 2.1 g of copper chloride, and 2 g of cetyltrimethylammonium bromide , stirred at room temperature for 3 hours, added 14 g of sodium dithionite, added an appropriate amount of saline to separate layers, removed water, washed the product twice with water, dried over anhydrous sodium sulfate, and obtained the formula (I) of R=H Product 87.3 g. 1 H NMR (CDCl 3 , ppm): 2.47 (3H, s), 2.88 (2H, t), 4.40 (2H, t), 5.78 (1H, m), 6.11 (1H, m), 6.33 (1H, m). ESI-MS m / z: 162.04.

[0035] Calculated by MOPAC software, the GAMESS Interface theoretical dipole moment of the compound of formula (I) prepared in Example 1 is 6.12 Debye.

Embodiment 2

[0037] Take 81 g of 2-methylthioethyl acrylate and place it in a 500 ml round-bottomed flask, add 80 ml of mass concentration of 30% hydrogen peroxide, 2.1 g of copper sulfate, and 2 g of cetyltrimethylammonium bromide, Stir the reaction at room temperature for 3 hours, add 14 g of sodium dithionite, add an appropriate amount of saline to separate layers, remove water, wash the product twice with water, and dry it with anhydrous sodium sulfate to obtain the formula (I) 87 of R=H g.

Embodiment 3

[0039] Take 81 g of 2-methylthioethyl acrylate and place it in a 500 ml round bottom flask, add 80 ml of 30% hydrogen peroxide, 2.3 g of copper acetate, and 2 g of cetyltrimethylammonium bromide, Stir the reaction at room temperature for 3 hours, add 14 g of sodium dithionate, add an appropriate amount of saline to separate layers, remove water, wash the product twice with water, and dry it with anhydrous sodium sulfate to obtain the formula (I) 88.2 of R=H g.

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Abstract

The invention discloses an acrylate compound containing a methyl sulfoxide structure. The compound has a structural formula as represented by formula (I). A preparation method for the acrylate compound containing a methyl sulfoxide structure is characterized in that 2-methylthioethyl (methyl) acrylate is used as a raw material and subjected to oxidation under the action of such decomposition accelerators as hydrogen peroxide and cupric hydrogen peroxide so as to prepare the acrylate compound. The acrylate compound containing a methyl sulfoxide structure has both methyl sulfoxide groups and (methyl) acrylate groups, high molecular dipole moment and strong dissolvability and can participate in cationic polymerization or free radical polymerization to improve intersolubility of structures of all the components in a cured coating.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an acrylate compound containing a methyl sulfoxide structure and a preparation method and application thereof. Background technique [0002] Acrylate compounds are widely used in polymer material synthesis or light-curing formulation systems because of their high-efficiency polymerizability. Small-molecular-weight acrylates are often used as reactive diluent monomers for light-curing coatings, inks, and adhesives. At the same time, because acrylate monomers generally undergo rapid free radical polymerization, acrylate monomers are often used in free radical photocurable formulations. At present, commonly used acrylate monomers are generally prepared based on simple alcohols or ether alcohol raw materials. In addition to acrylate groups, the commonly used acrylate monomer structures usually do not have other special functional groups, making acrylate monomers The over...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/18C07C315/02C08F20/38C08F2/48C09D4/02
Inventor 庞来兴
Owner GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD
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