Curable Composition With Saccharin for Delayed Cationic Curing

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Solution Overview

Problem

Existing curable compositions with delayed curing properties face challenges in achieving a balance between crosslinking acceleration and inhibition, particularly when using cationically polymerizable compounds like epoxy compounds, and have limited raw material options, making it difficult to control delayed curing properties effectively.

Innovation Solution

A curable composition comprising a compound with a (meth)acryloyl group, saccharin, and a photocationic or thermal cationic catalyst, optionally with a radical polymerization accelerator, which allows for delayed curing after irradiation or heating, regardless of the transparency of the adherend.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If a polyalcohol compound, polyether compound or plasticizer is added as a retarder to an epoxy compound and a cationic catalyst, then delayed curing property is achieved, but it is difficult to balance the degree of crosslinking acceleration by the cationic catalyst and the degree of crosslinking inhibition by the retarder

Engineering Contradiction:
Improvedelayed curing timeVSAvoidcontrol of crosslinking balance
Core Design Contradiction:
Duration of action of moving objectVSEase of operation

Solution Approach 1:

The patent changes the chemical structure parameters of the retarder from conventional polyalcohol/polyether compounds to a specific compound with formula (1) containing a carboxylic acid group and a hydroxyl group. This structural parameter change enables simultaneous achievement of delayed curing property and controllable crosslinking balance, as the specific molecular structure provides both retarder function and compatibility with the cationic catalyst system.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite curing system combining the cationic catalyst (photocationic or thermal cationic catalyst) with the specifically structured retarder compound of formula (1). This composite approach allows the retarder to work synergistically with the catalyst, achieving both delayed curing and proper crosslinking balance that cannot be achieved with conventional single-function retarders.

Inventive Principle:
Principle #40Composite materials

2Duration of action of moving object

If cationically polymerizable compounds like epoxy compounds are used, then delayed curing property can be achieved, but the number of functional groups and raw material options are limited

Engineering Contradiction:
Improvedelayed curing timeVSAvoidraw material options
Core Design Contradiction:
Duration of action of moving objectVSAdaptability or versatility

Solution Approach 1:

The patent develops a universal retarder compound of formula (1) that can be used with various cationic catalyst systems (both photocationic and thermal cationic catalysts) and different cationically polymerizable compounds. This multi-functional retarder structure provides versatility across different raw material options while maintaining delayed curing property, overcoming the limitation of epoxy compound-specific retarders.

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

Solution Approach 2:

The patent introduces a new class of retarder compounds with specific structural parameters (carboxylic acid group combined with hydroxyl group in formula (1)) that expands the raw material options beyond conventional epoxy-based systems. This parameter change in retarder structure enables broader adaptability to different cationically polymerizable compounds while maintaining the desired delayed curing effect.

Inventive Principle:
Principle #35Parameter changes

3Duration of action of moving object

If a retarder is added to achieve delayed curing property, then curing time is extended, but the degree of crosslinking is inhibited

Engineering Contradiction:
Improvedelayed curing timeVSAvoiddegree of crosslinking
Core Design Contradiction:
Duration of action of moving objectVSStrength

Solution Approach 1:

The patent changes the chemical parameters of the retarder to achieve optimal balance between delayed curing time and crosslinking degree. The specific compound of formula (1) with carboxylic acid group and hydroxyl group provides controlled retardation that extends working time while maintaining sufficient crosslinking density for mechanical strength, unlike conventional retarders that overly inhibit crosslinking.

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 composition secures a delayed curing time for works like laminating or tightening, ensuring effective curing after a specific period post-irradiation or heating, with improved control over curing time and broader applicability to various materials.

Implementation Method 1

an epoxy compound and the like have curability due to light irradiation in the presence of a cationic catalyst

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Implementation Method 2

a photocationic catalyst as a component (C-1)

Methodology Applied
Scientific EffectPhoto-initiated cationic polymerization: Photopolymerisation

Implementation Method 3

a thermal cationic catalyst as a component (C-2)

Methodology Applied
Scientific EffectThermal polymerization:

Implementation Method 4

a composition having delayed curing property that the composition is not cured immediately after irradiation with an energy ray and is cured after specific time has elapsed

Methodology Applied
Scientific EffectDelayed curing:

Data Source

PatentUS12528893B2Curable composition
Publication Date: 2026.01.20 THREE BOND CO LTD
  • US12528893B2 patent drawing
  • US12528893B2 patent drawing
  • US12528893B2 patent drawing

AI summary

The present invention provides a curable composition capable of securing delayed curing time for carrying out a work such as laminating or tightening after carrying out irradiation with an energy ray or heating and capable of exhibiting delayed curing property after that, regardless of whether an adherend is transparent or not. The present invention is a curable composition comprising components (A) to (C): a component (A): a compound having a (meth)acryloyl group in a molecule; a component (B): saccharin; and a component (C): at least one of a photocationic catalyst as a component (C-1) and a thermal cationic catalyst as a component (C-2).