Synthesis method of allyl oxetane compound for ultraviolet light curing

A technology of allyl oxetane and hydroxymethyl oxetane, which is applied in the field of organic chemistry and new materials, can solve the problem of poor mechanical and thermal properties, unsatisfactory curing speed, and large volume shrinkage and other problems, to achieve the effect of simple and easy feeding process, high utilization rate of reactor, and simple feeding process

Inactive Publication Date: 2015-09-09
NANCHANG UNIV
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Problems solved by technology

[0003] Liu Anchang of Wuhan Engineering University and others have done some research on the synthesis of the precursor 3-ethyl-3-hydroxymethyloxetane, and Liu Haitao and Mo Jianhua of Huazhong University of Science and Technology have done some research on its ring-opening polymerization. At present, there is no report on the synthesis of allyl oxetane compounds in China
In addition, there are not many domestic and foreign reports on the application of oxetane compounds, especially (UV) ultraviolet light curing.
[0004] The domestic existing reactive diluents for UV-curable resins are added to the formula. After curing, there are large volume shrinkage, poor dilution effect, high water absorption, poor transparency of the adhesive layer, insufficient gloss, and slow curing speed. Ideal, poor mechanical properties and thermal properties

Method used

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  • Synthesis method of allyl oxetane compound for ultraviolet light curing
  • Synthesis method of allyl oxetane compound for ultraviolet light curing
  • Synthesis method of allyl oxetane compound for ultraviolet light curing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 23.2 g (0.2 mol) 3-ethyl-3-hydroxymethyl oxetane, 48.4 g (0.4 mol) allyl Bromine, 50 g (50%) potassium hydroxide aqueous solution, adjust the magnetic rotary stirrer to make it stir vigorously, then add 1.0 g tetrabutylammonium bromide, keep the reaction at about 0 °C, react for 28 hours, and the reaction ends. 32.5 g of the organic phase was separated, and the content of the product 3-ethyl-3-allylmethoxyxetane in the organic phase was analyzed by gas chromatography to be 83%. The reaction yield reached 86.5%.

[0038] Raw material 3-ethyl-3-hydroxymethyl oxetane in embodiment 1 and synthetic product 1 H-NMR and FT-IR spectrum see figure 1 , figure 2 , image 3 .

Embodiment 2

[0040] Add 23.2 g (0.2 mol) 3-ethyl-3-hydroxymethyl oxetane, 36.3 g (0.3 mol) allyl Bromine, 50 g (40%) sodium hydroxide aqueous solution, adjust the magnetic stirrer to make it stir vigorously, then add 1.0 g tetraphenylphosphonium chloride, keep the reaction at about 0 ° C, react for 28 hours, and the reaction is over. 31.4 g of the organic phase was separated, and the content of the product 3-ethyl-3-allylmethoxyxetane in the organic phase was analyzed by gas chromatography to be 75%. The reaction yield reached 75.5%.

Embodiment 3

[0042] Add 20.4 g (0.2 mol) 3-methyl-3-hydroxymethyl oxetane, 48.4 g (0.4 mol) allyl Bromine, 50 g (50%) potassium hydroxide aqueous solution, adjust the magnetic stirrer to make it stir vigorously, then add 1.0 g tetrabutylammonium bromide, keep the reaction at about 0 ° C, react for 29 hours, and the reaction ends. 31.6 g of the organic phase was separated, and the content of the product 3-methyl-3-allylmethoxyxetane in the organic phase was analyzed by gas chromatography to be 80%. The reaction yield reached 89%.

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Abstract

The invention relates to a synthesis method of an allyl oxetane compound for ultraviolet light curing. The synthesis method comprises: in the presence of an aqueous solution or suspension of an alkali, under continuous vigorous stirring, adding a 3-hydroxymethyl oxetane compound and 3-halo-propylene, adding an appropriate amount of a phase transfer catalyst, carrying out a phase transfer catalysis reaction for 24-30 h at a reaction temperature of -5-5 DEG C, and then carrying out dehydrohalogenation esterification so as to obtain the product. According to the present invention, the allyl oxetane compound having extremely low viscosity and capable of concurrently being used for free radical and cation curing can be prepared, and the synthesis method has characteristics of simple and easy-performing related reactions, no requirement of heating, less by-products, environmental protection, high yield, high equipment utilization rate, and easy large-scale industrial production of the allyl oxetane compound.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and novel materials. Background technique [0002] Oxetane compounds are very important organic compound monomers. After ring-opening polymerization of such monomers, they can form functional prepolymers whose main chain is polyether links. This prepolymer can be widely used in medicine, Coatings, lubricants, adhesives, rapid prototyping of 3D stereolithography and many other fields are currently being researched on their synthesis and application at home and abroad. [0003] Liu Anchang of Wuhan Engineering University and others have done some research on the synthesis of the precursor 3-ethyl-3-hydroxymethyloxetane, and Liu Haitao and Mo Jianhua of Huazhong University of Science and Technology have done some research on its ring-opening polymerization. At present, there is no report on the synthesis of allyl oxetane compounds in China. In addition, there are not many domestic and for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/06C08G59/16C08G59/14
CPCC07D305/06C08G59/145C08G59/1461
Inventor 黄笔武谢王付
Owner NANCHANG UNIV
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