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Compound containing methyl sulfoxide structure, and preparation method and application thereof

A technology for methyl sulfoxide and compounds, which is applied in the field of compounds containing methyl sulfoxide structures and their preparation, can solve the problems of low volatility, permeation migration, difficult dispersion, etc., and achieves the effect of good solubility

Active Publication Date: 2012-10-24
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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  • Compound containing methyl sulfoxide structure, and preparation method and application thereof
  • Compound containing methyl sulfoxide structure, and preparation method and application thereof
  • Compound containing methyl sulfoxide structure, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Take 88 g of allyl methyl sulfide and place it in a 1000 ml round bottom flask, add 555 ml of 30% hydrogen peroxide, 6.2 g of formic acid peroxide, and 39 g of cetyltrimethylammonium bromide, and stir at room temperature After reacting for 4 hours, add 180 g of sodium hydrosulfate, add an appropriate amount of saline to separate layers, remove water, wash the product twice with water, and dry over anhydrous sodium sulfate to obtain 102.6 g of the compound of formula (II), 1 H NMR (CDCl 3 , ppm): 2.61 (3H, s), 2.52 ~ 2.79 (2H, d-d), 2.89 (2H, m), 2.93 (1H, m) ESI-MS m / z: 120.14.

[0040] Take 60 g of the compound of formula (II) and place it in a 250 ml three-necked flask, add 37 g of acrylic acid, 0.5 g of tetrabutylammonium bromide, and 0.6 g of p-methoxyphenol, raise the temperature to 75°C, stir and heat the reaction, and measure When the acid value drops below 6 mgKOH / g, the reaction is stopped to obtain the product methyl sulfoxide acrylate (I). 1 H NMR (CDCl 3 ...

Embodiment 2

[0043]Take 88 g of allyl methyl sulfide and place it in a 1000 ml round bottom flask, add 295 ml of 30% hydrogen peroxide, 34.5 g of acetic acid peroxide, and 17 g of cetyltrimethylammonium bromide, and stir at room temperature After reacting for 5 hours, add 180 g of sodium dithionite, add salt until the layers are separated, remove water, wash the product twice with water, and dry over anhydrous sodium sulfate to obtain 93.2 g of the compound of formula (II).

[0044] Take 60 g of the compound of formula (II) and place it in a 250 ml three-necked flask, add 37 g of acrylic acid, 0.5 g of tetrabutylammonium chloride, and 0.6 g of p-methoxyphenol, raise the temperature to 75°C, stir and heat the reaction, and measure When the acid value drops below 6 mgKOH / g, the reaction is stopped to obtain the product methyl sulfoxide acrylate (I).

Embodiment 3

[0046] Take 88 g of allyl methyl sulfide and place it in a 1000 ml round bottom flask, add 295 ml of 30% hydrogen peroxide, 25 g of formic acid peroxide, and 5.5 g of cetyltrimethylammonium bromide, and stir at room temperature After reacting for 5 hours, add 180 g of sodium dithionite, add salt until the layers are separated, remove water, wash the product twice with water, and dry over anhydrous sodium sulfate to obtain 112.0 g of the compound of formula (II).

[0047] Take 60 g of the compound of formula (II) and place it in a 250 ml three-necked flask, add 37 g of acrylic acid, 0.5 g of tetramethylammonium bromide, and 0.6 g of p-methoxyphenol, raise the temperature to 75°C, stir and heat the reaction, and measure When the acid value drops below 6 mgKOH / g, the reaction is stopped to obtain the product methyl sulfoxide acrylate (I).

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Abstract

The invention discloses a compound containing a methyl sulfoxide structure. The compound has a structural formula as represented by formula (I). A preparation method for the compound containing a methyl sulfoxide structure is characterized in that allyl methyl sulfide is used as a raw material, then hydrogen peroxide and percarboxylic acid are added at normal temperature so as to obtain an intermediate product with a thioether bond oxidized into sulfoxide and a double bond oxidized into an epoxy group, and then a quaternary ammonium salt catalyst is added to react with (methyl) acrylic acid so as to prepare the compound containing a methyl sulfoxide structure. The 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 specifically relates to a compound containing a methyl sulfoxide structure and a preparation method and application thereof. Background technique [0002] Epoxy compounds or acrylate compounds are widely used in polymer material synthesis or light-curing formulation systems because of their high-efficiency polymerizability. Small molecular weight epoxy compounds or acrylates are often used as reactive diluent monomers for light-curing coatings , inks, adhesives. Epoxy compounds can undergo cationic polymerization and are generally used in cationic light-curing systems; acrylate monomers generally undergo rapid free-radical polymerization, so acrylate monomers are often used in free-radical light-curing 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 acry...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/18C07C315/04C09D4/02C09D4/00C09D11/00C09J4/02C09J4/00
Inventor 庞来兴
Owner GUANGDONG BOSSIN NOVEL MATERIALS TECH CO LTD
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