Thermally Triggered Silyl Hydride Epoxide Curing via Amine Blocking

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Solution Overview

Problem

Existing Lewis acid catalyzed reactions, such as those between silyl hydrides and epoxides, are highly reactive and difficult to control, making it challenging to create shelf-stable one-part systems that can be triggered to react on demand, especially when exposed to UV light or at elevated temperatures.

Innovation Solution

A composition comprising a silyl hydride, epoxide, and a thermally triggered amine blocking agent that complexes with the Lewis acid catalyst at room temperature, preventing reaction, but releases the catalyst at elevated temperatures to initiate the reaction, allowing for a shelf-stable one-part system that can be triggered to react quickly upon heating.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If UV light sensitive blocking agents are used to block Lewis acid catalysts, then the system can be stored stably in the dark, but the system requires UV light exposure to initiate reaction and needs to be kept in the dark during storage

Engineering Contradiction:
Improvestorage stabilityVSAvoidease of initiation
Core Design Contradiction:
Stability of the object's compositionVSAdaptability or versatility

Solution Approach 1:

The patent changes the triggering parameter from UV light exposure to thermal energy. The amine blocking agent is selected to release the Lewis acid catalyst at elevated temperatures (e.g., above 50°C) while maintaining stable complexation at room temperature, enabling simple thermal initiation without UV light equipment and eliminating the need for dark storage.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If the reaction system is made highly reactive to achieve fast curing, then the cure speed improves, but the system becomes difficult to control and reacts too quickly once components are combined

Engineering Contradiction:
Improvecure speedVSAvoidcontrollability
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The patent applies preliminary action by pre-complexing the Lewis acid catalyst with the amine blocking agent in a stable complex that can be stored indefinitely at room temperature. The actual catalytic activity is postponed until thermal energy triggers the release of the catalyst from the complex, providing precise control over when the fast reaction occurs.

Inventive Principle:
Principle #10Preliminary action

3Ease of operation

If a one-part system is created to simplify application, then the ease of operation improves, but the system loses shelf stability because reactants and catalyst would react immediately upon mixing

Engineering Contradiction:
Improvesimplicity of useVSAvoidshelf stability
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent introduces an intermediary substance (the amine blocking agent) that temporarily deactivates the Lewis acid catalyst by forming a stable complex. This intermediary allows all reaction components to coexist in a single part without immediate reaction, and can be removed by applying thermal energy during use, enabling both one-part simplicity and shelf stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 rapid curing at elevated temperatures (e.g., 95 °C) with a cure speed of 10 minutes or less, maintaining stability at room temperature and allowing for controlled reaction initiation, suitable for applications in coatings and adhesives.

Implementation Method 1

Heating the composition releases the Lewis acid catalyst from the amine blocking agent and allows it to catalyze a reaction between the silyl hydride and epoxide

Methodology Applied
Scientific EffectThermal energy triggers dissociation of the amine-Lewis acid complex: Thermolysis

Implementation Method 2

Strong Lewis acids are known catalysts for numerous reactions. For instance, the Piers-Rubinsztajn (PR) reaction between silyl hydride and silyl ether is a well-known reaction catalyzed by a strong Lewis acid, particularly tris(pentafluorophenyl) borane ('BCF')

Methodology Applied
Scientific EffectLewis acid catalysis: Catalysis

Data Source

PatentEP3980431B1Thermally initiated acid catalyzed reaction between silyl hydride and epoxides
Publication Date: 2023.05.10 DOW SILICONES CORP
  • EP3980431B1 patent drawing
  • EP3980431B1 patent drawing
  • EP3980431B1 patent drawing

AI summary

A composition contains a mixture of silyl hydride, an epoxide, a Lewis acid catalyst and an amine having the following formula: R1 R2 R3 N; where the nitrogen (N) is not a member of a N=C-N linkage and wherein each of R1, R2, and R3 is independently selected from a group consisting of hydrogen, alkyl, substituted alkyl, and conjugated moieties; and wherein at least one of R1, R2, and R3 is a conjugated moiety connected to the nitrogen by a conjugated carbon if the epoxide is linear and wherein none of R1, R2, and R3 are connected to the amine nitrogen with a conjugated carbon if the epoxide is a cyclic epoxide.