Methods for preparing branched poly (2-hydroxyethyl methacrylate) at room temperature by inverse emulsion polymerization

Patent metadata

Field	Value
Publication number	US-11814451-B2
Application number	US-202217935573-A
Country	US
Kind code	B2
Filing date	Sep 26, 2022
Priority date	Apr 3, 2020
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

Abstract

The present disclosure may generally relate to the field of polymer synthesis and provide a method for preparing branched poly(2-hydroxyethyl methacrylate) at room temperature by inverse emulsion polymerization. The method may include: using benzoyl peroxide as an oxidant, and 2-methyl-N-[3-(methyl-phenyl-amino)-propyl]-acrylamide as a reductant monomer to form a redox initiation system, water, and toluene as media, a nonionic surfactant as an emulsifier, 2-hydroxyethyl methacrylate as a monomer, reacting at room temperature and normal pressure to obtain branched poly(2-hydroxyethyl methacrylate). In the present disclosure, the polymerization system may be simple and stable, and the synthesis and purification of the reductant monomer may be simple, greatly reducing the polymerization cost. The reaction may not need temperature control and pressure control, with low energy consumption, easy operation, and less impact on the environment. The obtained branched poly(2-hydroxyethyl methacrylate) may have a high molecular weight. The molecular weight and a branching degree may be adjusted in a wide range. The method may be of great significance to the theoretical research and large-scale application of branched poly(2-hydroxyethyl methacrylate).

First claim

What is claimed is:

1. A method for preparing branched poly (2-hydroxyethyl methacrylate) at room temperature by inverse emulsion polymerization, the method comprising:
using benzoyl peroxide (BPO) as an oxidant and 2-methyl-N-[3-(methyl-phenyl-amino)-propyl]-acrylamide (MPAEMA) as a reductant monomer to form a redox initiation system, water and toluene as media, emulsifiers, 2-hydroxyethyl methacrylate as a polymer monomer, and obtaining branched poly (2-hydroxyethyl methacrylate) by a reaction at the room temperature through radical inverse emulsion polymerization, wherein
a ratio of amount of substance of the oxidant monomer and amount of substance of the reductant monomer is 1:1;
the polymer monomer is added to water to dissolve to form an aqueous solution with a concentration of 25%;
a reaction temperature of the polymerization is 25° C.;
a reaction time of the polymerization is 8 hours;
a ratio of amount of substance of the reductant monomer and amount of substance of the polymer monomer is 1:80-1:160; and
a mass ratio of water phase and toluene is 1:1.

2. The method of claim 1 , wherein the reductant monomer 2-methyl-N-[3-(methyl-phenyl-amino)-propyl]-acrylamide is prepared by:
(1) dissolving N-(3-aminopropyl)-N-methylaniline, triethylamine, and methacryloyl chloride in tetrahydrofuran respectively to prepare a dilute solution with a concentration of 1 g/10 mL;
(2) mixing and vigorously stirring the N-(3-aminopropyl)-N-methylaniline solution and the triethylamine solution at 0° C.-5° C. to form a mixed solution, simultaneously dropping the methacryloyl chloride solution into the mixed solution slowly, reacting for 24 hours, filtering out a filtrate, removing a solvent in the filtrate by rotary evaporation to obtain a crude product, and dissolving the crude product in diethyl ether and dropping into n-hexane for recrystallization to obtain the reductant monomer MPAEMA.

3. The method of claim 2 , wherein a mole ratio of N-(3-aminopropyl)-N-methylaniline, triethylamine, and methacryloyl chloride in (2) is 4:6:5.

4. The method of claim 1 , wherein a total mass of the emulsifiers is 10% of a mass of the toluene.

Assignees

• Univ Changzhou

Inventors

• Huang Wenyan
• Jiang Bibiao
• Jiang Li
• Yang Hongjun
• Jiang Qimin
• Xue Xiaoqiang
• Zhu Di

Classifications

• C08F120/20 Primary

  of polyhydric alcohols or {polyhydric} phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F220/20 Primary

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F2/30

  non-ionic · CPC title

• C08F4/40

  Redox systems · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title