Sterically Hindered Aliphatic Polyamine Cross-Linking Agents for Epoxy Resin Recyclability

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Solution Overview

Problem

Conventional epoxy resin compositions have short working times, making them unsuitable for applications requiring long handling and processing periods, and they are not recyclable due to irreversible cross-linking reactions.

Innovation Solution

The development of epoxy resin compositions incorporating sterically hindered aliphatic polyamine cross-linking agents that extend working times and allow for recyclability by using cleavable cross-linking groups, enabling longer processing windows and subsequent degradation for material recovery.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If conventional epoxy resin compositions are used, then the cross-linking reaction is fast and complete, but the working time is short and the material is not recyclable

Engineering Contradiction:
Improveworking timeVSAvoidrecyclability
Core Design Contradiction:
Duration of action of moving objectVSReliability

Solution Approach 1:

The patent changes the chemical structure of the cross-linking agent by introducing sterically hindered aliphatic polyamines with specific molecular structures (Formula 1) that have controlled reactivity. This parameter change in molecular structure allows the system to achieve both extended working time and recyclability by modifying the cross-linking mechanism rather than simply adding more time or heat.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces dynamic characteristics to the cross-linking system through cleavable cross-linking groups that can break down under specific conditions. This allows the cross-linked polymer to transition from a stable cured state to a degradable state, enabling recyclability while maintaining structural integrity during the working time period.

Inventive Principle:
Principle #15Dynamics

2Ease of operation

If conventional epoxy resin compositions are used, then the material cures quickly, but the handling and processing time is limited

Engineering Contradiction:
Improvehandling and processing timeVSAvoidcuring speed
Core Design Contradiction:
Ease of operationVSProductivity

Solution Approach 1:

The patent implements a two-stage curing process with distinct time periods: a first period for polymerization and cross-linking at elevated temperature, and a second period for degradation and recovery at lower temperature. This periodic action allows the system to achieve complete curing when needed while enabling processing and handling during the extended working time period before final curing.

Inventive Principle:
Principle #19Periodic action

Solution Approach 2:

The patent performs preliminary polymerization and cross-linking reactions during the first curing period at elevated temperature, creating a partially cured network that provides structural integrity. This preliminary action allows the material to be handled and processed during the working time period, with the final curing occurring after processing is complete.

Inventive Principle:
Principle #10Preliminary action

3Reliability

If conventional epoxy resin compositions are used, then the cross-linking is irreversible, but recycling and material recovery are not possible

Engineering Contradiction:
Improvestructural stabilityVSAvoidrecyclability
Core Design Contradiction:
ReliabilityVSEase of repair

Solution Approach 1:

The patent enables the degradation of cross-linked polymers under specific conditions to recover and reuse the original monomers and oligomers. The cleavable cross-linking groups allow the network to be systematically broken down, and the recovered materials can be reused in new formulations, creating a circular material flow that maintains structural stability during use while enabling recycling when needed.

Inventive Principle:
Principle #34Discarding and recovering

Solution Approach 2:

The patent introduces dynamic reversibility to the cross-linking system through cleavable cross-linking groups that can transition between bound and unbound states. This dynamic characteristic allows the cross-linked structure to maintain stability during normal use while enabling controlled degradation for recycling, effectively making the cross-linking reaction reversible under appropriate conditions.

Inventive Principle:
Principle #15Dynamics

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 use of sterically hindered aliphatic polyamines in epoxy resin compositions provides extended working times, allowing for longer handling and processing, and enables recyclability by breaking down cross-linked polymers, addressing the limitations of conventional epoxy systems.

Implementation Method 1

epoxy resin compositions containing sterically hindered, reworkable aliphatic amines

Methodology Applied
Scientific EffectChemical Bonding: Chemical Bonding

Implementation Method 2

aliphatic polyamine cross-linking agent comprising a compound having Formula (1)

Methodology Applied
Scientific EffectCross-linking: Chemical Bonding

Implementation Method 3

enables recyclability by breaking down cross-linked polymers

Methodology Applied
Scientific EffectDegradation: Decomposition (biological)

Implementation Method 4

cleavable cross-linking groups

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS9862797B2Sterically hindered aliphatic polyamine cross-linking agents, compositions containing them and uses thereof
Publication Date: 2018.01.09 ADITYA BIRLA CHEM (USA) INC
  • US9862797B2 patent drawing
  • US9862797B2 patent drawing
  • US9862797B2 patent drawing

AI summary

The present disclosure relates, in part, to an epoxy resin composition comprising: an epoxy resin; and an aliphatic polyamine (e.g., as a cross-linking agent), wherein the aliphatic polyamine comprises a compound having the structure of Formula (1): wherein each of R1 and R2 is independently selected from the group consisting of hydrogen, alkyl group, cycloalkyl group and aromatic group; or R1 and R2 together with the carbon atom to which they are attached form a cyclic ring; each of R3 and R4 is independently selected from the group consisting of hydrogen, alkyl group, cycloalkyl group and aromatic group.