Urethane Acrylate Resin Cure Accelerators for Anaerobic Adhesives

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Solution Overview

Problem

There is a need for alternative anaerobic cure accelerators to replace conventional components like saccharin and acetyl phenylhydrazine, which have faced regulatory scrutiny and supply chain concerns, while maintaining comparable cure speeds and physical properties in anaerobic adhesive compositions.

Innovation Solution

The development of urethane/urea/thiourethane (meth)acrylate resins as cure accelerators, formed from compounds with specific functional groups and isocyanate materials, which can be used in place of conventional accelerators to accelerate the curing process of anaerobic adhesives and sealants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional cure accelerators like saccharin and acetyl phenylhydrazine are used, then cure speed is maintained, but regulatory compliance and supply chain reliability deteriorate

Engineering Contradiction:
Improveregulatory compliance and supply chain reliabilityVSAvoidcure speed
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention changes the chemical structure parameters of the accelerator from conventional saccharin/APH-based systems to urethane/urea/thiourethane (meth)acrylate resins with specific functional groups (-OH, -NH2, or -SH). This structural parameter change enables regulatory compliance while maintaining cure acceleration functionality through the reactive functional groups that interact with the anaerobic curable composition.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention employs composite accelerator resins that combine multiple functional groups (hydroxyl, amino, or thiol) within a single molecular structure containing (meth)acrylate functionality. This composite approach creates a multifunctional accelerator that can participate in both the curing reaction and provide the required regulatory compliance, replacing the need for separate accelerator and monomer components.

Inventive Principle:
Principle #40Composite materials

2Reliability

If new alternative accelerators are developed, then regulatory compliance improves, but cure performance may deteriorate

Engineering Contradiction:
Improveregulatory complianceVSAvoidcure performance
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention optimizes molecular parameters including the selection of X (C1-20 alkyl, C2-20 alkenyl, or C7-20 alkaryl groups), the type of functional groups (-OH, -NH2, or -SH), and the value of z (1-3) to tune the reactivity and performance of the accelerator resin while maintaining regulatory compliance. These parameter adjustments enable customization of cure performance for different applications.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces specific local functional groups (-OH, -NH2, or -SH) at designated positions within the molecular structure to provide localized reactivity zones that interact with the curable composition. This local quality approach ensures that the accelerator functionality is concentrated at specific sites, optimizing cure performance while the rest of the molecular structure provides regulatory compliance and stability.

Inventive Principle:
Principle #3Local quality

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

These new cure accelerators provide comparable or improved cure speeds and physical properties, offering a regulatory compliant and supply chain resilient solution for anaerobic curable compositions, reducing dependence on restricted chemicals.

Implementation Method 1

urethane/urea/thiourethane (meth)acrylate resins from diols

Methodology Applied
Scientific EffectUrethane formation: Chemical Bonding

Implementation Method 2

urethane/urea/thiourethane (meth)acrylate resins from diols

Methodology Applied
Scientific EffectUrea formation: Chemical Bonding

Implementation Method 3

urethane/urea/thiourethane (meth)acrylate resins from diols

Methodology Applied
Scientific EffectThiourethane formation: Chemical Bonding

Implementation Method 4

a free-radically polymerizable acrylate ester monomer

Methodology Applied
Scientific EffectFree-radical polymerization: Photopolymerisation

Data Source

PatentEP2424931B1Cure accelerators for anaerobic curable compositions
Publication Date: 2015.03.04 HENKEL IP & HOLDING GMBH
  • EP2424931B1 patent drawingFigure 1
  • EP2424931B1 patent drawingFigure 2
  • EP2424931B1 patent drawingFigure 3

AI summary

The present invention relates to cure accelerators useful for anaerobic curable compositions, such as adhesives and sealants. The cure accelerators are constructed as urethane/urea/thiourethane (meth)acrylate resins from diols and include a unit embraced within structure A (see A) where X is C1-20 alkyl, C2-20 alkenyl, or C7-20 alkaryl, any of which may be interrupted by one or more hereto atoms, and which are functionalized by at least one and preferably at least two groups selected from -OH, -NH2 or -SH and Z is 1-3.