Ruthenium Alkylidene Catalysts for Homogeneous Cycloolefin Polymerization

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for ring-opening metathesis polymerization of cycloolefins using ruthenium-based catalysts face issues such as inadequate control over polymerization, leading to inhomogeneous materials with bubbles and insufficient compressive strength, and require organic solvents, which are environmentally harmful and costly.

Innovation Solution

The use of ruthenium alkylidene complexes with 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligands for ring-opening metathesis polymerization, which provides high compressive strength, controlled polymerization, and eliminates the need for organic solvents, allowing for a more environmentally friendly and cost-effective process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If Grubbs II catalyst is used for ring-opening metathesis polymerization, then compressive strength is improved, but polymerization control deteriorates leading to inhomogeneous material with bubbles

Engineering Contradiction:
Improvecompressive strengthVSAvoidpolymerization control
Core Design Contradiction:
StrengthVSManufacturing precision

Solution Approach 1:

The patent modifies the ligand structure from symmetric (Grubbs II uses symmetric NHC ligands) to asymmetric 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligands. This structural parameter change in the catalyst maintains high compressive strength while improving polymerization control and eliminating bubbles, resolving the contradiction between strength and manufacturing precision.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional ruthenium catalysts are used, then polymerization activity is maintained, but material homogeneity deteriorates resulting in inhomogeneous polymer

Engineering Contradiction:
Improvepolymerization activityVSAvoidmaterial homogeneity
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent changes the ligand configuration from conventional symmetric structures to asymmetric 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligands. This parameter change preserves polymerization activity while achieving homogeneous material formation without bubbles, resolving the contradiction between productivity and composition stability.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If organic solvents are added to the reaction mixture, then catalyst dissolution is improved, but environmental impact worsens and cost increases

Engineering Contradiction:
Improvecatalyst dissolutionVSAvoidenvironmental impact
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent extracts and eliminates the organic solvent from the reaction system by designing catalysts with improved solubility characteristics. The asymmetric NHC ligand catalysts achieve adequate dissolution in the reaction mixture without requiring additional organic solvents, thereby removing the harmful factor while maintaining ease of manufacture.

Inventive Principle:
Principle #2Taking out (Extraction)

4Productivity

If polymerization rate is increased to improve productivity, then output increases, but material homogeneity deteriorates causing excessive viscosity increase and inhomogeneous material

Engineering Contradiction:
Improvepolymerization rateVSAvoidmaterial homogeneity
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent modifies the catalyst structure by introducing asymmetric 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligands, which changes the polymerization kinetics parameters. This allows maintaining high productivity through controlled polymerization rates while preventing excessive viscosity increase and ensuring homogeneous material formation.

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 ruthenium alkylidene complexes achieve a high compressive strength similar to Grubbs II catalysts while ensuring homogeneous material formation and reducing environmental impact by minimizing solvent use, thus offering a better compromise of properties and cost-effectiveness.

Implementation Method 1

The present invention relates to a method for the polymerization of cycloolefins by ring-opening metathesis. The reaction is carried out in the presence of at least one particular catalyst, selected from the ruthenium alkylidene complexes

Methodology Applied
Scientific EffectRing-opening metathesis polymerization (ROMP): Chemical Bonding

Data Source

PatentUS11261290B2Method for the polymerization of cycloolefins by means of ring-opening metathesis
Publication Date: 2022.03.01 VIPO FRANCE SAS
  • US11261290B2 patent drawing
  • US11261290B2 patent drawing
  • US11261290B2 patent drawing

AI summary

The present invention relates to a method for the polymerization of cycloolefins by ring-opening metathesis. The reaction is carried out in the presence of at least one particular catalyst, selected from the ruthenium alkylidene complexes comprising at least one 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand and mixtures thereof. The invention also relates to a kit for implementing this method.