Dithioester RAFT Agent for Crosslinked Polymer Efficiency

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Solution Overview

Problem

Conventional RAFT agents used in controlled radical polymerization have a low ability to abstract hydrogen, which hampers the efficiency of forming crosslinked polymer structures, leading to reduced forming efficiency when used as additives in synthesizing polymer materials with crosslinked structures.

Innovation Solution

A novel dithioester compound is developed, represented by a specific formula, which generates an aralkyloxy radical with a high ability to abstract hydrogen, suitable for use as a RAFT agent in synthesizing polymer materials with crosslinked structures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If a conventional RAFT agent is used to control radical polymerization, then the polymerization can be controlled, but the hydrogen abstraction ability is low which reduces the efficiency of forming crosslinked structures

Engineering Contradiction:

Improveforming efficiency of crosslinked structureVSAvoidhydrogen abstraction ability

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The patent changes the chemical structure parameters of the RAFT agent by introducing specific groups ( Formula 1 shows the structural modification with R1, R2, R3, and Z groups) to enhance the hydrogen abstraction ability of the generated radical, thereby improving crosslinking efficiency while maintaining polymerization control

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite functional structure by combining the RAFT agent functionality with enhanced hydrogen abstraction capability through specific molecular design, resulting in a dual-functional compound that performs both polymerization control and efficient crosslinking

Inventive Principle:

Principle #40Composite materials

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The dithioester compound effectively enhances the hydrogen abstraction ability of the aralkyloxy radical, improving the efficiency of forming crosslinked polymer structures when used as a RAFT agent.

Implementation Method 1

R cleaves to generate a radical (R.), and this radical has an ability of reacting with a monomer to re-initiate polymerization

Methodology Applied

Scientific EffectRadical reaction:

Implementation Method 2

the dithioester compound generates an aralkyloxy radical (R1R2R3CO.) having high ability of abstracting hydrogen

Methodology Applied

Scientific EffectHydrogen abstraction:

Implementation Method 3

Z affects the stability of the intermediate radical, and controls the reactivity of the thiocarbonyl group (C═S) of the RAFT agent to free radical addition

Methodology Applied

Scientific EffectFree radical addition:

Data Source

PatentUS11370760B2Dithioester compound

Publication Date: 2022.06.28 SUMITOMO RUBBER INDUSTRIES LTD

AI summary

An object of the present invention is to provide a dithioester compound generating an aralkyloxy radical having high ability of abstracting hydrogen. The present invention provides a dithioester compound represented by a formula (1).In the formula (1), R1 and R2 each independently represent an alkyl group having 1 or more carbon atoms, an alkenyl group having two or more carbon atoms, an alkynyl group having two or more carbon atoms, an aryl group having 6 or more carbon atoms and optionally having a substituent group, an aralkyl group having 6 or more carbon atoms, a hydrogen atom, or a halogen atom; R3 represents an aryl group having 6 or more carbon atoms and optionally having a substituent group, or an aralkyl group having 6 or more carbon atoms and optionally having a substituent group.