Hydroxythiol Curable Compositions for High Sensitivity and Storage Stability

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Solution Overview

Problem

Current curable compositions face challenges with low sensitivity, poor storage properties, insufficient curing due to light penetration issues, oxygen inhibition, and poor developability, particularly in the development of color filters and other optical materials.

Innovation Solution

The use of hydroxythiol compounds with both mercapto and hydroxyl groups, combined with compounds having ethylenically unsaturated double bonds and photopolymerization or thermal polymerization initiators, to enhance sensitivity, developability, and storage stability, eliminating the need for oxygen shielding layers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If polyfunctional thiol compounds are used to increase sensitivity, then photopolymerization sensitivity is improved, but storage properties deteriorate

Engineering Contradiction:
Improvephotopolymerization sensitivityVSAvoidstorage properties
Core Design Contradiction:
Measurement precisionVSStability of the object's composition

Solution Approach 1:

The invention changes the chemical structure parameter of the thiol compound by introducing a hydroxyl group adjacent to the mercapto group. This structural modification enables the compound to function as both a photopolymerization initiator and a stabilizer, resolving the contradiction between sensitivity and storage properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The hydroxythiol compound serves multiple functions simultaneously: it acts as a photopolymerization initiator, a stabilizer preventing premature polymerization, and a contributor to developability. This multi-functionality eliminates the need for separate additives and resolves the contradiction between sensitivity enhancement and storage stability

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Reliability

If greater light energy is applied to achieve sufficient curing, then curing depth is improved, but energy consumption increases

Engineering Contradiction:
Improvecuring depthVSAvoidenergy consumption
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The invention changes the absorption characteristics parameter by selecting compounds with ethylenically unsaturated double bonds that absorb light at specific wavelengths. Combined with the hydroxythiol initiator's high sensitivity, this enables effective curing at lower light energy levels while maintaining adequate curing depth

Inventive Principle:
Principle #35Parameter changes

3Productivity

If excessive amount of photopolymerization initiator is used to increase sensitivity, then photopolymerization speed is improved, but storage stability deteriorates

Engineering Contradiction:
Improvephotopolymerization speedVSAvoidstorage stability
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The invention changes the chemical reactivity parameter by introducing the hydroxyl group that forms hydrogen bonds with the mercapto group. This interaction stabilizes the initiator during storage, allowing use of sufficient initiator amounts for high polymerization speed without compromising storage stability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The hydroxyl group acts as an intermediary that mediates between the mercapto group and environmental factors. It provides steric and electronic stabilization, enabling the system to achieve both high initiator concentration for fast curing and storage stability

Inventive Principle:
Principle #24Intermediary (Mediator)

4Reliability

If oxygen shielding membrane is provided to prevent oxygen inhibition, then curing quality is improved, but device complexity increases

Engineering Contradiction:
Improvecuring qualityVSAvoidoxygen shielding membrane
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention converts the harmful effect of oxygen into a beneficial one by utilizing the hydroxyl group's ability to interact with oxygen-containing environments. The hydroxyl group provides stability even in the presence of oxygen, eliminating the need for shielding membranes while maintaining curing quality

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The hydroxythiol compound provides self-protection against oxygen inhibition through its molecular structure. The hydroxyl group inherently stabilizes the system without requiring external oxygen shielding, allowing the composition to serve itself and eliminate complex shielding structures

Inventive Principle:
Principle #25Self-service

5Stability of the object's composition

If aliphatic groups are increased to improve storage stability, then storage properties are improved, but developability deteriorates

Engineering Contradiction:
Improvestorage stabilityVSAvoiddevelopability
Core Design Contradiction:
Stability of the object's compositionVSEase of operation

Solution Approach 1:

The invention changes the molecular weight and structural complexity parameters by using relatively low molecular weight hydroxythiol compounds with simple structures. This maintains good developability while the hydroxyl group provides the necessary storage stability without requiring excessive aliphatic content

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 curable compositions exhibit improved sensitivity, excellent developability, and good storage properties, enabling efficient curing and pattern formation without the need for additional shielding, suitable for applications like color filters and optical materials.

Implementation Method 1

curable compositions that are cured with heat or light... photopolymerization or thermal polymerization initiator... cured by polymerization reaction

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Implementation Method 2

curable compositions that are cured with heat or light... thermal polymerization initiator... cured by polymerization reaction

Methodology Applied
Scientific EffectThermal polymerization:

Data Source

PatentUS8053167B2Curable compositions containing hydroxythiol compound, and cured products thereof
Publication Date: 2011.11.08 RESONAC CORP
  • US8053167B2 patent drawing
  • US8053167B2 patent drawing
  • US8053167B2 patent drawing

AI summary

Curable compositions have high sensitivity and excellent developability, and further have good storage properties as required. The compositions include a hydroxythiol compound represented by Formula (1) below and a compound with an ethylenically unsaturated double bond:wherein R1 and R2 are each independently a hydrogen atom, a C1-10 alkyl group or an aromatic ring; X is an aliphatic group, an aromatic ring-containing group or a heterocyclic ring-containing group; Y is an ester bond; k and l are each an integer ranging from 1 to 20; m is an integer of 0, 1 or 2; and n is 0 or 1.