Thiol-ene CAN Polymer for Reshaping and Recycling

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Solution Overview

Problem

Conventional polymer fabrication methods, such as 3D printing and casting, do not allow for easy reshaping of polymer objects once they have been formed, and there is a significant issue with polymer waste that is not recyclable.

Innovation Solution

A thiol-ene covalent adaptable network (CAN) polymer system is developed, using monomers with thiol and anhydride functional groups that form reversible thioester bonds, enabling objects to be reshaped at low temperatures and subsequently fixed in a permanent shape by deactivating the catalyst, and can be degraded using a solution with free thiols and a catalyst for recycling.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If conventional polymer fabrication methods are used, then polymer objects can be manufactured, but they cannot be easily reshaped once formed

Engineering Contradiction:
ImproveReshaping capabilityVSAvoidShape fixation
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent applies dynamic covalent chemistry by incorporating reversible thioester bonds into the polymer network. These bonds can dynamically break and reform under specific conditions (presence of free thiols and catalyst), allowing the polymer object to transition between fixed and reshapeable states. This resolves the contradiction by making the polymer composition dynamically adaptable rather than statically fixed.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent changes the chemical parameter of the polymer bonds from permanent covalent bonds to reversible thioester bonds. By controlling the presence/absence of free thiol compounds and catalysts, the polymer network can switch between stable and reshappable states, enabling both shape fixation and reshaping capability.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If conventional polymer fabrication methods are used, then polymer objects can be manufactured, but polymer wastes cannot be recycled

Engineering Contradiction:
ImproveManufacturing capabilityVSAvoidPolymer waste
Core Design Contradiction:
Ease of manufactureVSLoss of substance

Solution Approach 1:

The patent enables polymer waste recovery through controlled degradation. The reversible thioester bonds allow the polymer network to be broken down into its monomeric components using free thiol compounds and catalysts. These recovered monomers can then be reused for new polymer fabrication, eliminating waste and enabling a circular economy approach.

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The patent extracts the polymer network into its constituent monomers through chemical degradation. By applying free thiol compounds and catalysts, the thioester bonds are cleaved, releasing the original monomers that can be separated, purified, and reused for new polymer synthesis.

Inventive Principle:
Principle #2Taking out (Extraction)

3Adaptability or versatility

If reversible bonds are used to enable reshaping, then polymer objects can be reshaped, but the bonds must be deactivated to fix the permanent shape

Engineering Contradiction:
ImproveShape adjustmentVSAvoidPermanent shape fixation
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent uses dynamic covalent chemistry where the thioester bonds are reversible under specific conditions but stable under others. The presence of free thiols and catalysts enables bond exchange for reshaping, while their absence or deactivation leads to stable, permanent shape fixation. This dynamic behavior resolves the contradiction between adaptability and reliability.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent applies preliminary anti-action by using deactivation of the catalyst or removal of free thiol compounds to prevent further bond exchange after the desired shape is achieved. This deactivation step locks the polymer network into its current configuration, ensuring permanent shape fixation and preventing unintended future reshaping.

Inventive Principle:
Principle #9Preliminary anti-action

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 CAN polymer system allows for the reshaping and recycling of polymer objects, addressing the limitations of conventional methods and reducing polymer waste through controlled degradation and recycling.

Implementation Method 1

a reversible thioester group formed by a thiol group from the first repeating unit and an anhydride functional group from the second repeating unit

Methodology Applied
Scientific EffectThioester bond formation: Chemical Bonding

Implementation Method 2

a thioether group from by a thiol group from the first repeating unit and an alkene functional group from the second repeating unit

Methodology Applied
Scientific EffectThiol-ene addition reaction: Chemical Bonding

Implementation Method 3

subject the polymer to a solution including a free thiol compound and a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20240124645A1Composition for reversible polymerization of thioester and methods thereof
Publication Date: 2024.04.18 THE REGENTS OF THE UNIVERSITY OF COLORADO
  • US20240124645A1 patent drawing
  • US20240124645A1 patent drawing
  • US20240124645A1 patent drawing

AI summary

Described herein is a composition for producing a thiol-ene covalent adaptable network (CAN) polymer. The composition includes a first monomer including at least one thiol group; and a second monomer including at least one anhydride functional group and at least one alkene functional group. Also described herein are a polymer produced from the composition, a method of producing the polymer using the composition, a method of fabricating a polymer article using the composition, as well as a method of degrading the polymer.