Aromatic Thioether Monomers for High-Index Optical Polymers

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Solution Overview

Problem

Current thiol-ene and thiol-yne polymerization systems face limitations in achieving high refractive index materials with enhanced cure rates for optical applications, particularly in communications, sensors, and displays.

Innovation Solution

The development of aromatic thioether compounds with terminal alkene and/or alkyne functionality, combined with organic polythiols and a free-radical photoinitiator, to form high-index optical materials through partial polymerization, allowing for enhanced cure rates and suitable polymer compositions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional thiol-ene and thiol-yne polymerization systems are used, then polymerization can proceed, but the cure rates are slow and the refractive index is insufficient for advanced optical applications

Engineering Contradiction:
Improvecure rateVSAvoidrefractive index
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent modifies the chemical structure of the thiol-ene/yne monomers by introducing aromatic rings and specific functional groups (allyl or propargyl groups) to change the optical parameters (refractive index) and reaction kinetics (cure rate) of the polymerization system

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite polymer structures by combining aromatic thioether compounds with terminal alkene/alkyne groups and polythiol compounds, achieving both high refractive index and enhanced cure rates through the synergistic interaction of multiple functional groups

Inventive Principle:
Principle #40Composite materials

2Reliability

If high refractive index materials are synthesized through conventional methods, then optical properties improve, but the cure rates remain insufficient for advanced applications

Engineering Contradiction:
Improverefractive indexVSAvoidcure rate
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of the monomers by using aromatic thioether compounds with terminal alkene/alkyne groups, which simultaneously enhances the refractive index and accelerates the cure rate through improved reaction kinetics

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs aromatic thioether compounds as intermediary substances that facilitate faster polymerization reactions while providing the desired high refractive index properties, acting as a bridge between the thiol and the unsaturated group

Inventive Principle:
Principle #24Intermediary (Mediator)

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 resulting polymerized compositions exhibit improved cure rates and refractive index properties, making them suitable for advanced optical materials in communications, sensors, and displays.

Implementation Method 1

The composition may be combined with an organic polythiol having at least two sulfhydryl groups and a free-radical photoinitiator, and then at least partially polymerized to form a polymerized composition

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Implementation Method 2

Both reactions are often facilitated by a free-radical initiator and/or UV irradiation

Methodology Applied
Scientific EffectUV irradiation: Light

Implementation Method 3

The thiol-ene reaction is a reaction between a thiol and an alkene to form an alkyl sulfide

Methodology Applied
Scientific EffectThiol-ene reaction: Chemical Bonding

Implementation Method 4

the thiol-yne reaction is a reaction between a thiol and an alkyne to produce an alkenyl sulfide

Methodology Applied
Scientific EffectThiol-yne reaction: Chemical Bonding

Data Source

PatentUS11505653B2Compositions and methods of making a polymerized composition
Publication Date: 2022.11.22 3M INNOVATIVE PROPERTIES CO
  • US11505653B2 patent drawing
  • US11505653B2 patent drawing
  • US11505653B2 patent drawing

AI summary

A composition comprising at least one terminally-unsaturated diarylsulfide compound represented by the formula: wherein each R represents an allyl group or a propargyl group. The composition may further comprise an organic polythiol, and optionally a free-radical initiator, and may be formulated as a two-part polymerizable composition. Methods of polymerizing the compositions are also disclosed.