Borate-Based Base Generator for Stable Epoxy Curing

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Solution Overview

Problem

Existing base generators for polymerization reactions, particularly those generating strong bases like biguanides, face challenges with storage stability when mixed with base-reactive compounds, leading to premature curing and convenience issues during storage and use.

Innovation Solution

A borate-based compound with a specific structure, capable of generating strong bases upon irradiation or heating, is developed, which forms a salt with a cation having high basicity, exhibiting low nucleophilicity and thus minimizing reaction with base-reactive compounds, ensuring high storage stability and efficient curing initiation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If a base generator generating strong bases like biguanides is used for polymerization reactions, then curing efficiency is improved, but storage stability deteriorates due to premature curing

Engineering Contradiction:
Improvecuring efficiencyVSAvoidstorage stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The base generator is divided into two separate components: a borate compound and a generating agent. These components can be stored separately without reacting with each other, maintaining storage stability. When mixed with the base-reactive compound and activated, they work together to generate strong bases for efficient curing.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The borate compound acts as an intermediary that, when combined with the generating agent, produces the strong base effect. The borate compound itself does not react with base-reactive compounds, but enables their reaction when activated by the generating agent, thus resolving the contradiction between storage stability and curing efficiency.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of operation

If a base generator is mixed with base-reactive compounds in advance, then convenience is improved, but storage stability deteriorates leading to premature curing

Engineering Contradiction:
ImproveconvenienceVSAvoidstorage stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The base generator components (borate compound and generating agent) are segmented and can be stored separately in the mixed composition without causing premature curing. This segmentation allows the composition to be prepared in advance with improved convenience while maintaining storage stability, as the components only interact when activated.

Inventive Principle:
Principle #1Segmentation

3Reliability

If weak bases like primary and secondary amines are used for curing epoxy groups, then storage stability is improved, but curing speed deteriorates requiring high temperature heating

Engineering Contradiction:
Improvestorage stabilityVSAvoidcuring speed
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention changes the base strength parameter by using a borate compound that generates strong bases (biguanides, phosphazenes, phosphoniums) when activated, instead of using weak bases directly. This parameter change enables fast curing at lower temperatures while maintaining storage stability through the segmented base generator design.

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 borate-based compound maintains storage stability without reacting with base-reactive compounds, allowing for long-term storage without performance degradation and enables effective curing of base-reactive compositions upon activation.

Implementation Method 1

a base generator which generates a base by irradiation of light (active energy rays) or by heating

Methodology Applied
Scientific EffectPhoto-decomposition: Photodissociation

Implementation Method 2

a base generator which generates a base by irradiation of light (active energy rays) or by heating

Methodology Applied
Scientific EffectThermal decomposition: Thermolysis

Data Source

PatentEP3098226B1Borate-based base generator, and base-reactive composition comprising such base generator
Publication Date: 2018.12.12 FUJIFILM WAKO PURE CHEMICAL CORP
  • EP3098226B1 patent drawing
  • EP3098226B1 patent drawing
  • EP3098226B1 patent drawing

AI summary

An object of the present invention is to provide a compound which is capable of attaining a composition having high storage stability without reacting with a base-reactive compound, even in the case of storage for a long period of time in a mixed state with the base-reactive compound, such as an epoxy-based compound, as well as capable of generating a strong base (guanidines, biguanides, phosphazenes or phosphoniums) by irradiation of light (active energy rays) or heating; a base generator comprising the compound; and a base-reactive composition comprising the base generator and the base-reactive compound. The present invention relates to the compound represented by the general formula (A); the base generator comprising the compound; and the base-reactive composition comprising the base generator and the base-reactive compound. (wherein R1 represents an alkyl group; an arylalkynyl group which may be substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group; an alkenyl group; a 2-furylethynyl group; a 2-thiophenylethynyl group; or a 2,6-dithianyl group; R2 to R4 each independently represent an alkyl group; an arylalkynyl group which may be substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group; the aryl group which may be substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group; a furanyl group; a thienyl group; or an N-alkyl-substituted pyrrolyl group; Z+ represents an ammonium cation having a guanidinium group, a biguanidium group or a phosphazenium group, or a phosphonium cation.)