Two-Component RT Curable Resin Eliminates Toxic Oxime Release

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Solution Overview

Problem

Existing RT-curable resin compositions face issues with toxicity and environmental impact due to the release of carcinogenic oxime compounds and toxic alcohols during curing, as well as the use of tin catalysts which are environmentally hazardous.

Innovation Solution

A two-pack RT fast-curing resin composition is developed, featuring a first pack with an organic polymer capped with hydrolyzable silyl or hydroxysilyl groups, a hydrolyzable organosilane compound, and a curing catalyst, and a second pack with an additional organic polymer. This composition releases a cyclic ketone compound like cyclobutanone or cyclopentanone upon curing, which is non-toxic and environmentally safe, eliminating the need for tin catalysts.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If deoximation type curing agents are used, then curing speed is improved, but carcinogenic oxime compounds are released

Engineering Contradiction:
Improvecuring speedVSAvoidcarcinogenic oxime compounds release
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical parameter of the curing agent from deoximation type (releasing oxime) to dealcoholization type (releasing alcohol), specifically using organosilane compounds that release non-toxic alcohols like cyclohexanol or nonane-1,3-diol, thereby maintaining curing efficiency while eliminating carcinogenic emissions

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the harmful oxime release mechanism into a beneficial alcohol release mechanism by selecting organosilane crosslinking agents that undergo dealcoholization condensation, where the released alcohol compounds serve as harmless byproducts that even contribute to the polymer network formation without causing health hazards

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

2Object-affected harmful factors

If dealcoholization type curing agents are used, then non-toxic curing is achieved, but toxic alcohol compounds are released

Engineering Contradiction:
Improvetoxicity reductionVSAvoidtoxic alcohol release
Core Design Contradiction:
Object-affected harmful factorsVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical parameter of the released alcohol from toxic small molecules (like methanol) to non-toxic cyclic alcohols (like cyclohexanol) or diols (like nonane-1,3-diol) by selecting specific organosilane structures, thereby eliminating toxicity while maintaining the dealcoholization curing mechanism

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite organosilane compounds combining silicon atoms with specific cyclic alcohol groups (cyclohexyl, nonane-1,3-diol structures) that provide both the crosslinking functionality and the non-toxic alcohol release characteristic, creating a multi-functional curing agent

Inventive Principle:
Principle #40Composite materials

3Productivity

If tin catalysts are used, then curing catalysis is improved, but environmental pollution increases

Engineering Contradiction:
Improvecuring catalysis efficiencyVSAvoidenvironmental pollution
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention extracts and removes tin catalysts from the curing system entirely, replacing them with non-toxic organic catalysts such as triethylamine or dibenzylideneacetone, thereby eliminating the environmental pollution source while maintaining catalytic functionality through alternative chemical mechanisms

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention introduces organic base catalysts as intermediary substances that mediate the hydrolysis and condensation reactions of organosilane compounds, providing alternative catalytic pathways that do not involve toxic metal catalysts while still achieving efficient curing

Inventive Principle:
Principle #24Intermediary (Mediator)

4Ease of operation

If one-pack RT curable composition is used, then ease of operation is improved, but curing speed decreases

Engineering Contradiction:
Improvehandling convenienceVSAvoidcuring speed
Core Design Contradiction:
Ease of operationVSProductivity

Solution Approach 1:

The invention divides the curable composition into two separate packs: Pack A containing the organopolysiloxane base polymer and Pack B containing the organosilane crosslinking agent, allowing stable storage of individual components and enabling fast curing only after mixing, thus resolving the contradiction between ease of storage and curing speed

Inventive Principle:
Principle #1Segmentation

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 achieves fast cure and excellent deep-section cure without the toxicity and environmental concerns associated with previous compositions, making it suitable for various applications such as adhesives, sealing agents, and coating agents.

Implementation Method 1

A polymer having a reactive silicon group (referred to as 'hydrolyzable silyl group,' hereinafter) hydrolyzes and condenses in the presence of water

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 2

a silicon group having a hydroxy group on the silicon atom (referred to as 'hydroxysilyl or silanol group,' hereinafter) condenses with a hydrolysis product of the hydrolyzable silyl group or a silanol group

Methodology Applied
Scientific EffectCondensation: Condensation

Implementation Method 3

the composition crosslinks or cures through hydrolytic condensation reaction at RT (23±15°C) with the aid of airborne moisture or water after mixing of two packs

Methodology Applied
Scientific EffectHydrolytic condensation reaction: Hydrolysis

Data Source

PatentEP4556531A1Two-component type room temperature rapid-curable resin composition and article
Publication Date: 2025.05.21 SHIN ETSU CHEMICAL CO LTD
  • EP4556531A1 patent drawing
  • EP4556531A1 patent drawing
  • EP4556531A1 patent drawing

AI summary

This two-component type room temperature rapid-curable resin composition comprises, at a specific ratio: a first agent containing, at a specific ratio, (A) an organic polymer in which the molecule chain terminals are blocked by a hydrolysable silyl group and/or a hydroxyl silyl group, and in which an organopolysiloxane structure is not included in the polymer main chain, (B) a hydrolyzable organosilane compound represented by formula (1) (in formula (1), R1 represents a monovalent hydrocarbon group, n represents 1-8, and m represents 3 or 4) and/or a partial hydrolysis condensate thereof, and (C) a curing catalyst; and a second agent containing (A') an organic polymer in which the molecule chain terminals are blocked by a hydrolysable silyl group and/or a hydroxyl silyl group, and in which an organopolysiloxane structure is not included in the polymer main chain. The two-component type room temperature rapid-curable resin composition has excellent rapid curability and deep curability, provides fine workability, and, when being cured, causes elimination/release of a cyclic ketone compound such as cyclobutanone and cyclopentanone as a leaving group (elimination compound). Thus, the composition solves problems regarding safety and hazardous properties with respect to human and the environment.