Aromatic Vinyl Ether Curing via Structured Sulfonium Salt

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Solution Overview

Problem

Cationically polymerizable curable compositions containing a vinyl ether compound with an aromatic group substituted with a vinyloxy group often fail to cure favorably upon light exposure and/or heating.

Innovation Solution

Incorporating a sulfonium salt with a specific structure as a cationic polymerization initiator, which includes a benzene ring with a methyl group at the ortho position relative to the sulfur atom, to facilitate curing of the aromatic vinyl ether compound.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If a vinyl ether compound with an aromatic group substituted with a vinyloxy group is used as a curable component, then the cured product achieves excellent hardness, but the composition fails to cure favorably upon light exposure and/or heating

Engineering Contradiction:

Improvehardness of cured productVSAvoidcuring performance

Core Design Contradiction:

StrengthVSReliability

Solution Approach 1:

The invention changes the chemical structure parameters of the cationic polymerization initiator by specifying that at least one of R1 or R2 must not be an alkyl group optionally substituted with a halogen atom. This structural parameter change enables the initiator to effectively initiate polymerization of aromatic vinyl ether compounds, resolving the contradiction between achieving hard cured products and maintaining reliable curing performance.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite curable composition system combining specifically structured sulfonium salt initiators with aromatic vinyl ether compounds. This composite approach allows the initiator and monomer to work synergistically, where the initiator's specific structure compensates for the aromatic group's steric hindrance, enabling both excellent hardness and favorable curing.

Inventive Principle:

Principle #40Composite materials

2Ease of manufacture

If conventional cationic polymerization initiators are used with aromatic vinyl ether compounds, then the composition can be formulated, but curing does not proceed favorably under light exposure or heating

Engineering Contradiction:

Improveformulability of compositionVSAvoidcuring performance

Core Design Contradiction:

Ease of manufactureVSReliability

Solution Approach 1:

The invention modifies the initiator structure parameters by defining specific constraints on R1 and R2 groups. This parameter optimization maintains ease of formulation while dramatically improving curing reliability, allowing the composition to be easily manufactured and then effectively cured under light or heat.

Inventive Principle:

Principle #35Parameter changes

3Device complexity

If a sulfonium salt with alkyl groups optionally substituted with halogen atoms is used, then the initiator structure is simple, but it cannot effectively initiate polymerization of aromatic vinyl ether compounds

Engineering Contradiction:

Improvestructural complexity of initiatorVSAvoidpolymerization initiation capability

Core Design Contradiction:

Device complexityVSReliability

Solution Approach 1:

The invention optimizes the initiator structure by imposing specific constraints: at least one of R1 or R2 must not be an alkyl group optionally substituted with a halogen atom. This parameter change increases structural complexity slightly but dramatically improves polymerization initiation capability, resolving the contradiction between simplicity and effectiveness.

Inventive Principle:

Principle #35Parameter changes

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 use of this sulfonium salt ensures favorable curing of the aromatic vinyl ether compound, resulting in a cured product with excellent hardness and mechanical properties, even under light exposure and/or heating.

Implementation Method 1

a cationic polymerization initiator (A) and an aromatic vinyl ether compound (B)... easily cured upon at least one of light exposure and heating

Methodology Applied

Scientific EffectPhotopolymerization: Photopolymerisation

Implementation Method 2

easily cured upon at least one of light exposure and heating

Methodology Applied

Scientific EffectThermal polymerization initiation:

Data Source

PatentUS10479879B2Curable composition, cured product of the curable composition, and method of producing a cured product using the curable composition

Publication Date: 2019.11.19 TOKYO OHKA KOGYO CO LTD

AI summary

A cationically polymerizable curable composition comprising a compound having a vinyloxy group bonded to an aromatic group which is easily cured upon light exposure and/or heating, a cured product of the curable composition, and a method of producing a cured product using the curable composition. In a cationically polymerizable curable composition that includes a compound having a vinyloxy group bonded to an aromatic group, a sulfonium salt having a specific structure is used as a curing agent. A cured product is produced by shaping the curable composition into a predetermined shape, and subjecting the shaped curable composition to light exposure and/or heating.