Polymerizable Ionic Liquid with Aromatic Carboxylate Anion

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Solution Overview

Problem

Current polymerizable ionic liquids have high melting points, making them difficult to use in various applications at ambient temperatures, and they often require solvents, which can lead to inefficiencies and environmental concerns.

Innovation Solution

Development of polymerizable ionic liquids with a cation and an aromatic carboxylate anion, both comprising free-radically polymerizable (meth)acrylate groups, which have a melting point below 100°C, allowing for easier handling and potential solvent-free use due to their low viscosity and ability to cure in air.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If polymerizable ionic liquids are designed with conventional cations and anions, then they exhibit good polymerizability, but their melting points are high making them difficult to use at ambient temperatures

Engineering Contradiction:
Improvemelting pointVSAvoidhandling at ambient temperature
Core Design Contradiction:
TemperatureVSEase of operation

Solution Approach 1:

The patent changes the chemical structure parameters of the ionic liquid components by introducing aromatic carboxylate anions with specific substituents and combining them with suitable cations to achieve low melting points below 100°C while maintaining polymerizability through (meth)acrylate groups

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite ionic liquid structures combining aromatic carboxylate anions with organic cations containing (meth)acrylate groups, achieving a balance between low melting point and polymerizability that neither component could achieve alone

Inventive Principle:
Principle #40Composite materials

2Productivity

If polymerizable ionic liquids are used without solvents, then manufacturing efficiency improves and environmental concerns are reduced, but high melting points make them difficult to handle

Engineering Contradiction:
Improvemanufacturing efficiencyVSAvoidmelting point
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent modifies the physical parameters of the ionic liquid by selecting specific aromatic carboxylate anions and cation combinations that result in melting points below 100°C, enabling solvent-free processing at ambient or slightly elevated temperatures without requiring additional heating energy

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If conventional ionic liquids are used, then ionic character is maintained, but polymerizable groups are absent preventing curing applications

Engineering Contradiction:
Improvecuring capabilityVSAvoidionic liquid structure
Core Design Contradiction:
Adaptability or versatilityVSStability of the object's composition

Solution Approach 1:

The patent merges the ionic liquid structure with polymerizable (meth)acrylate functional groups by combining aromatic carboxylate anions with cations containing these groups, creating a hybrid material that exhibits both ionic liquid properties and polymer curing capability

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent creates multi-functional ionic liquids that simultaneously provide ionic character for liquid state at low temperatures and polymerizable (meth)acrylate groups for curing applications, enabling a single material to serve multiple functions

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 polymerizable ionic liquids can be used to create curable compositions that harden at ambient temperatures, reducing manufacturing time and energy consumption while minimizing volatile organic compound emissions and surface residues.

Implementation Method 1

polymerizable ionic liquids with a cation and an aromatic carboxylate anion, both comprising free-radically polymerizable (meth)acrylate groups

Methodology Applied
Scientific EffectFree-radical polymerization: Photopolymerisation

Data Source

PatentEP2571909B1Polymerizable ionic liquid comprising aromatic carboxylate anion
Publication Date: 2016.10.05 3M INNOVATIVE PROPERTIES CO
  • EP2571909B1 patent drawing
  • EP2571909B1 patent drawing
  • EP2571909B1 patent drawing

AI summary

Presently described are polymerizable ionic liquids comprising a cation and an aromatic carboxylate anion; wherein the cation, anion, or both comprise a free-radically polymerizable group. Also described are curable compositions comprising such polymerizable ionic liquids and at least one other free-radically polymerizable monomer, oligomer, or polymer.