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Oxetane compound and preparation method thereof

A technology for oxetane compounds, which is applied in the field of oxetane compounds and their preparation, can solve the problems of low selectivity, high viscosity, and limited applications

Active Publication Date: 2019-03-01
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the types of oxetane compounds in these coating compositions are limited, the selectivity is small, there is still a problem of being sensitive to humidity, and the cured product has an odor
In addition, for solvent-free systems, the viscosity of these compositions is usually high, which limits the application in some fields such as low-viscosity inks

Method used

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  • Oxetane compound and preparation method thereof
  • Oxetane compound and preparation method thereof
  • Oxetane compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Preparation of Intermediate 1

[0058]

[0059] Add 58g (0.5mol) of raw material 1, 4g (0.1mol) of sodium hydroxide and 100g of toluene to a 250ml four-necked flask equipped with a stirring device, a thermometer, and a reflux condenser in sequence, stir and heat up to 80°C, and dropwise add 86g (0.5mol) of mol) raw material 2, after 1.5h dropwise addition, continue to stir the reaction, follow the gas phase until the content of raw material 1 no longer changes, stop heating, adjust the pH value to neutral with 5% hydrochloric acid solution, filter, add water to fully stir, let stand to separate The removal of the water layer was repeated twice, and the toluene was distilled off the organic layer under reduced pressure to obtain 136 g of a light yellow liquid.

[0060] The structure of intermediate 1 was determined by GC-MS and 1 H-NMR confirmed.

[0061] MS(m / e): 289(M+1);

[0062] 1 H-NMR (CDCl 3 , 500MHz): δ0.96(6H, m), δ1.25(4H, m), δ2.01(1H, d), δ3.29(4H, s)...

Embodiment 2

[0070] Preparation of product 2

[0071]

[0072] Add 144g (0.5mol) intermediate 1,44g (0.25mol) p-dichlorobenzyl, 20g (0.5mol) sodium hydroxide and 150ml toluene successively in the 500ml four-necked flask that stirrer, thermometer, reflux condenser are housed, Reflux reaction, follow the gas phase until the intermediate 1 completely disappears, after the reaction, add water to fully stir, let it stand, separate the water layer, repeat twice, distill the organic layer under reduced pressure, remove toluene, and finally obtain 165g of viscous liquid.

[0073] The structure of product 2 was determined by GC-MS and 1 H-NMR confirmed.

[0074] MS(m / e): 679(M+1);

[0075] 1 H-NMR (CDCl 3 , 500MHz): δ0.96(12H, m), δ1.25(8H, m), δ3.29-3.51(18H, m), δ4.63-4.65(20H, m), δ7.12(4H, d).

Embodiment 3

[0077] Preparation of Intermediate 2

[0078]

[0079] Add 58g (0.5mol) of raw material 3, 4g (0.1mol) of sodium hydroxide and 100g of toluene in sequence to a 500ml four-necked flask equipped with a stirring device, a thermometer, and a reflux condenser, stir and heat up to 80°C, and dropwise add 85g of (0.25mol) toluene solution of raw material 4, after 1.5h dropwise addition, continue stirring reaction, gas phase tracking until the content of raw material 3 no longer changes, stop heating, adjust pH value to neutral with 5% hydrochloric acid solution, filter, add water fully Stir, stand still to separate the water layer, repeat twice, distill the organic layer under reduced pressure to remove toluene, and obtain 136 g of light yellow liquid.

[0080] The structure of intermediate 2 was determined by GC-MS and 1 H-NMR confirmed.

[0081] MS(m / e): 573(M+1);

[0082] 1 H-NMR (CDCl 3 , 500MHz): δ0.96(6H, m), δ1.25(4H, m), δ1.67(6H, s), δ2.01(2H, s), δ3.29-δ3.52(8H, m),...

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Abstract

The invention discloses an oxetane compound applied to cationic photocuring systems. The oxetane compound is formed by a compound containing at least one hydroxyl group and at least one oxetane groupand halogenated hydrocarbon via nucleophilic substitution reaction, is not sensitive to humidity, and has the advantages of being high in reactivity, low in odor and viscosity, and strong in adhesion.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to an oxetane compound which can be used in the field of photocuring and a preparation method thereof. Background technique [0002] The cationic photocuring system is not affected by oxygen inhibition, and the curing volume shrinkage is small, and it has good adhesion when applied to plastic or metal substrates. Generally, the cationic photocuring system contains alicyclic epoxy compounds, which are in contact with light of appropriate wavelengths, and in the presence of appropriate photoinitiators, polymerize to form cured products with good heat resistance, adhesion and chemical resistance . However, there are limitations in the application of cycloaliphatic epoxy compounds, which are particularly sensitive to humidity, and the water vapor in the application environment will significantly reduce the curing speed. W. Watt summarized the UV curing of epoxy in Chemistr...

Claims

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Application Information

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IPC IPC(8): C07D305/06C08G65/26
CPCC07D305/06C08G65/2603C07D305/00C08G59/02C08G65/26
Inventor 钱晓春胡春青金晓蓓
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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