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Method for preparing cyclic polymer by using allyl monomer through [3 +2] cyclization reaction as well as prepared polymer and application thereof

A cyclic polymer and cyclization reaction technology, applied in the field of light-induced polymerization, can solve the problem of low conversion rate of double bonds, and achieve the effect of high double bond conversion rate, mild reaction conditions, and easy catheter injection

Inactive Publication Date: 2021-08-10
GUANGZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, Chinese patent CN111072823A discloses a polymeric microsphere of a disaccharide-based skeleton and a preparation method thereof. A kind of polymeric microsphere of a disaccharide-based skeleton is prepared by using an allyl disaccharide ether and a photoinitiator, but still cannot overcome the transformation of double bonds. The rate is low (not more than 30%), and only the problem of oligomers with a molecular weight of several hundred to several thousand can be generated

Method used

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  • Method for preparing cyclic polymer by using allyl monomer through [3 +2] cyclization reaction as well as prepared polymer and application thereof
  • Method for preparing cyclic polymer by using allyl monomer through [3 +2] cyclization reaction as well as prepared polymer and application thereof
  • Method for preparing cyclic polymer by using allyl monomer through [3 +2] cyclization reaction as well as prepared polymer and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A kind of method that utilizes allyl monomer to prepare cyclic polymer by [3+2] cyclization reaction, with 1173 of 1mol as photoinitiator, the H of 3.3mol 2 C=CH-CH 2 -O-CH 3 As a monomer, distill 1g H with distilled water 2 C=CH-CH 2 -O-CH 3 , 0.1g1173 photoinitiator is completely dissolved in a single-necked bottle equipped with mechanical stirring, and is reacted in the air at room temperature with ultraviolet light irradiation, and the reaction lasts for 15 minutes to obtain a cyclic polymer, which is named: poly 1-( 2-(allyloxy)ethoxy)-2-((2-(allyloxy)ethoxy)methyl)cyclopentane or poly 1-(2-(allyloxy)ethoxy) yl)-3-((2-(allyloxy)ethoxy)methyl)cyclopentane.

[0042] The reaction process is: 1173 photoinitiators generate benzoyl radicals under light, and benzoyl radicals extract H 2 C=CH-CH 2 -O-CH 3 C-H of the hydrocarbon group next to the double bond, and then generate H 2 C=CH-CH·-O-CH 3 free radical, which then reacts with H 2 C=CH-CH 2 -O-CH 3 Form a...

Embodiment 2

[0047] A kind of method that utilizes allyl monomer to prepare cyclic polymer by [3+2] cyclization reaction, with ITX as photoinitiator, H 2 C=CH-CH 2 -O-CH 3 As a monomer, distilled water will 3.3mol of H 2 C=CH-CH 2 -O-CH 3 , 1mol of ITX, completely dissolved in a single-necked bottle equipped with mechanical stirring, reacted in the air at room temperature with ultraviolet light irradiation, the reaction continued for 15min, and a cyclic polymer (PSAE polymeric microspheres) was obtained, and its name was : Poly 1-(2-(allyloxy)ethoxy)-2-((2-(allyloxy)ethoxy)methyl)cyclopentane or poly 1-(2-(allyl) oxy)ethoxy)-3-((2-(allyloxy)ethoxy)methyl)cyclopentane.

[0048] The process of the above reaction is: the photoinitiator ITX produces a triplet substance under light, and the triplet substance extracts H 2 C=CH-CH 2 -O-CH 3 Hydrogen on the methylene next to the double bond, then H 2 C=CH-CH·-O-CH 3 Allyl radical, the allyl radical and H 2 C=CH-CH 2 -O-CH 3 Form a fiv...

Embodiment 3

[0054] A kind of method that utilizes allyl monomer to prepare cyclic polymer by [3+2] cyclization reaction, with 1mol of BP as photoinitiator, 3.3mol of H 2 C=CH-CH 2 -O-CH 3 As a monomer, distill 1g H with distilled water 2 C=CH-CH 2 -O-CH 3, 0.1gBP, completely dissolved in a single-necked bottle equipped with mechanical stirring, reacted in the air at room temperature with ultraviolet light irradiation, the reaction continued for 15min, and a cyclic polymer was obtained, named: poly 1-(2-( Allyloxy)ethoxy)-2-((2-(allyloxy)ethoxy)methyl)cyclopentane or poly 1-(2-(allyloxy)ethoxy)- 3-((2-(allyloxy)ethoxy)methyl)cyclopentane.

[0055] The process of the above reaction is: the photoinitiator benzophenone produces a triplet substance under light, and the triplet substance extracts H 2 C=CH-CH 2 -O-CH 3 Hydrogen on the methylene next to the double bond, then H 2 C=CH-CH·-O-CH 3 Allyl radical, the allyl radical and H 2 C=CH-CH 2 -O-CH 3 Form a five-membered ring free ...

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Abstract

The invention discloses a method for preparing a polymer by utilizing an allyl monomer through [3 + 2] cyclization reaction, the polymer prepared by the method and application of the polymer. The allyl monomer and a photoinitiator are utilized to participate in the reaction in a free radical or excited state through the [3 + 2] cyclization reaction, and a five-membered ring free radical product is formed through the cyclization reaction, and a polymerization reaction is triggered to obtain a polymer; the reaction is carried out at normal temperature, the reaction conditions are mild, the double bond conversion rate is high, the double bond conversion rate of the diallyl monomer can reach 45% or above in 500 seconds, the high-molecular-weight polymer with the molecular weight of ten thousands can be obtained, and the obtained polymer is proved to be all five-membered rings containing carbon atoms, and has the advantages of high molecular weight, high molecular weight, high molecular weight and the like; the molecular chain of the polymer also contains an annular structure, and the ring does not contain heteroatoms, so the prepared polymer has the characteristics of no toxicity, easiness in obtaining and good biological property, and can be applied to transcatheter arterial embolism.

Description

technical field [0001] The invention relates to the technical field of light-induced polymerization, and more specifically, relates to a method for preparing a cyclic polymer by using an allyl monomer through a [3+2] cyclization reaction, as well as the prepared polymer and its application. Background technique [0002] In the cycloaddition reaction, the synthesis of five-membered or six-membered ring compounds is the most common. Among them, the 1,3-dipolar cycloaddition reaction proposed by Huisgen in 1960 occurs between 1,3-dipole and alkenes and alkynes. The [3+2] cycloaddition reaction between hydrocarbons or corresponding derivatives, or called Huisgen reaction, the product is a five-membered heterocyclic compound. Olefin compounds are called dipolarophiles in the reaction. German chemist Rolf Huisgen took the lead in applying this type of reaction to prepare five-membered heterocyclic compounds. This type of reaction is an important method for the synthesis of monocy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F116/20C08F2/48A61L24/00A61L24/06
CPCA61L24/001A61L24/06C08F2/48C08F116/20C08L29/10
Inventor 叶国东周彦芳
Owner GUANGZHOU MEDICAL UNIV
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