Norbornene Resin Composition for Fast Curing and Low Shrinkage

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Solution Overview

Problem

Existing thermosetting resin compositions for construction purposes face challenges with slow curing at room temperature, high shrinkage, and toxicity, particularly in chemical anchoring applications, where fast curing and low shrinkage are essential for mechanical strength and adhesion.

Innovation Solution

A resin composition comprising a thiol, a norbornene-containing resin with a molecular weight of at least 500 Dalton, and a methacrylate reactive diluent, with the methacrylate content ranging from 5 to 75 weight percent, which allows for fast curing, low shrinkage, and improved workability, while being robust to variations in reactive diluent content.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of substance

If epoxy resin-amine systems are used for chemical anchoring, then low shrinkage and good adhesion are achieved, but curing is very slow at room temperature and does not occur at low temperatures

Engineering Contradiction:
ImproveshrinkageVSAvoidcuring speed
Core Design Contradiction:
Loss of substanceVSProductivity

Solution Approach 1:

The patent uses a composite resin system combining epoxy resin with methacrylate monomers and oligomers. This hybrid composition leverages the low shrinkage of epoxy resin while incorporating methacrylate components that enable fast curing at room temperature through radical polymerization, thus resolving the contradiction between low shrinkage and fast curing speed.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent modifies the chemical composition parameters of the resin system by adding methacrylate monomers (e.g., MMA, DMA) and oligomers in specific weight percentages (5-75% and 20-80% respectively). This parameter change enables the resin to cure rapidly at room temperature while maintaining low shrinkage characteristics, overcoming the limitation of conventional epoxy-amine systems.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If methacrylate-based resin compositions are used to achieve fast curing, then gel times of several minutes are obtained at room temperature, but substantial shrinkage occurs upon curing

Engineering Contradiction:
Improvecuring speedVSAvoidshrinkage
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The patent creates a composite resin system that combines methacrylate monomers with epoxy resin and oligomers. This composite approach maintains the fast curing speed of methacrylates while the epoxy resin and oligomer components reduce the overall shrinkage, thus resolving the contradiction between fast curing and low shrinkage.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes the weight percentage composition of methacrylate monomers (5-75%) and oligomers (20-80%) to achieve a balance between curing speed and shrinkage reduction. By carefully controlling these parameters, the resin system attains rapid gel times while minimizing shrinkage upon curing.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If reactive diluents like DCPD, norbornadiene, or vinylnorbornene are used to reduce viscosity, then cutting power is improved, but a relatively large amount is required which may reduce mechanical properties

Engineering Contradiction:
Improveviscosity reductionVSAvoidmechanical properties
Core Design Contradiction:
Ease of operationVSStrength

Solution Approach 1:

The patent uses norbornene-containing oligomers with specifically controlled molecular weights (500-50,000 Da) and functional group contents. This parameter optimization provides effective viscosity reduction while maintaining mechanical properties, as the oligomers contribute to the polymer network structure and strength even at lower concentrations compared to conventional reactive diluents.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent incorporates oligomers with specific functional groups (norbornene, carboxylic acid, hydroxyl) that provide localized functionality. These oligomers not only reduce viscosity but also participate in the curing reaction and contribute to mechanical properties, creating a system where viscosity reduction and strength enhancement occur in different functional aspects of the same material.

Inventive Principle:
Principle #3Local quality

4Ease of operation

If the amount of reactive diluent is changed to adjust viscosity, then workability is improved, but the system becomes highly sensitive to variation in reactive diluent content

Engineering Contradiction:
ImproveworkabilityVSAvoidrobustness to composition variation
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent creates a composite system with multiple components (epoxy resin, methacrylate monomers, oligomers) that work synergistically. This composite structure provides buffering capacity against composition variations, as changes in one component can be compensated by the others, thus maintaining system performance and reducing sensitivity to reactive diluent content variations.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent defines specific weight percentage ranges for each component (methacrylate monomers: 5-75%, oligomers: 20-80%) that create a robust formulation window. Within these parameter ranges, the system maintains consistent performance and workability even with variations in reactive diluent content, providing reliability and ease of manufacturing.

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 resin composition achieves fast curing at various temperatures, low shrinkage, and enhanced mechanical properties, providing flexibility in workflow and adhesion strength, suitable for chemical anchoring and adhesive applications.

Implementation Method 1

The resin composition is curable by radical polymerization

Methodology Applied
Scientific EffectRadical polymerization: Photopolymerisation

Implementation Method 2

a methacrylate containing compound as reactive diluent

Methodology Applied
Scientific EffectDilution:

Data Source

PatentUS9181129B2Resin suitable for construction purposes comprising norbornene functional groups and thiols
Publication Date: 2015.11.10 ACR III
  • US9181129B2 patent drawing
  • US9181129B2 patent drawing

AI summary

The present invention relates to a thermosetting resin composition suitable for construction purposes comprising (i) a thiol, (ii) a resin containing at least one norbornene group and having a molecular weight Mn of at least 500 Dalton, and (iii) a methacrylate containing compound whereby the resin composition comprises methacrylate containing compound in an amount of at least 5 wt % and at most 75 wt %, whereby 100 wt. % is the sum of methacrylate containing compound and resin containing at least one norbornene group. The present invention further relates to a two-component resin system consisting of component A and component B, wherein one of the components (A) comprises a resin containing at least one norbornene group and a methacrylate containing compound, whereby component (A) contains methacrylate containing compound in an amount of at least 5 wt % and at most 75 wt %, whereby 100 wt. % is the sum of methacrylate containing compound and resin containing at least one norbornene group; and the other component (B) comprises a thiol and a peroxide.