Cleavable Polyamine Synthesis for Recyclable Epoxy Curing
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Solution Overview
Problem
The recycling of products containing epoxy resins, particularly wind turbine rotor blades, is unsatisfactory, and there is a need for improved biodegradability of polyamine-based polymers.
Innovation Solution
A two-step process involving alkoxylation of amines with alkylene oxides followed by alcohol amination to synthesize functionalized cleavable amines, which are then used as co-reactants, hardeners, or curatives for epoxy resins, enhancing recyclability and biodegradability.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional polyamines are used in epoxy resins, then good mechanical performance and durability are achieved, but recyclability and biodegradability are poor
Solution Approach 1:
The patent changes the chemical structure of polyamines by introducing cleavable functional groups (acetal, ketal, or silyl ketal) into the amine backbone. This structural modification allows the polymer to maintain mechanical performance during normal use while enabling controlled degradation through acid treatment, thereby achieving both reliability and recyclability.
Solution Approach 2:
The patent segments the polyamine structure into distinct functional units with cleavable linkages. The backbone contains repeatable units with embedded cleavable groups that can be selectively broken down, allowing the polymer to be divided into manageable segments for recycling while maintaining overall structural integrity during service.
2Reliability
If conventional polyamines are used in epoxy resins, then good mechanical performance is achieved, but biodegradability is poor
Solution Approach 1:
The patent modifies the chemical parameters of polyamines by incorporating hydrolyzable functional groups (acetal, ketal, silyl ketal) that are susceptible to biological degradation. These structural changes enable the polymer to maintain mechanical strength during normal use while becoming biodegradable under appropriate conditions, thus resolving the contradiction between performance and environmental compatibility.
3Adaptability or versatility
If a two-step process (alkoxylation followed by alcohol amination) is used to synthesize cleavable amines, then recyclability and biodegradability are improved, but process complexity increases
Solution Approach 1:
The patent employs an intermediary approach by using alkylene oxides as intermediaries in the synthesis process. The alkoxylation step introduces a hydroxyl group that serves as a handle for subsequent alcohol amination, enabling the formation of cleavable functional groups through a controlled two-step sequence that balances complexity with effectiveness.
4Adaptability or versatility
If cleavable functional groups are introduced into polyamine backbones, then recyclability is improved, but manufacturing precision requirements increase
Solution Approach 1:
The patent utilizes parameter changes in the form of controlled reaction conditions during alkoxylation and alcohol amination steps. By optimizing temperature, pressure, catalyst selection, and reagent ratios, the process achieves high precision in introducing cleavable groups while maintaining scalability, thus resolving the contradiction between recyclability and manufacturing precision.
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 process enables the production of cleavable amines that improve the recyclability of epoxy systems and enhance the biodegradability of polyamine-based polymers, addressing the limitations of existing technologies.
Implementation Method 1
reacting at least one amine of general formula (I) with at least one C2-C4-alkylene oxide, thereby obtaining at least one first intermediate (I1), wherein the amine of general formula (I) comprises at least one, preferably terminal, group NH which is reacted with the C2-C4-alkylene oxide
Implementation Method 2
aminating the at least one first intermediate (I1) with at least one of ammonia, primary and secondary amines HNR'R'' to form at least one polyamine compound (II), comprising converting the at least one group N-CH2-CHR-OH or N-CHR-CH2-OH to the at least one group N-CH2-CHR-NR'R'' or N-CHR-CH2-NR'R''
Data Source
AI summary
A process for preparing polyamines via alkylene oxide addition to an amine followed by alcohol amination, comprising a) reacting at least one amine of general formula (I) with at least one C2-C4-alkylene oxide, thereby obtaining at least one first intermediate (11), wherein the amine of general formula (I) comprises at least one, preferably terminal, group NH which is reacted with the C2-C4-alkylene oxide, thereby obtaining at least one first intermediate (11), wherein at least one, preferably terminal, group NH of the amine of general formula (I) is converted to at least one group N-CH2-CHR-OH or N-CHR-CH2-OH with R being H or methyl or ethyl, preferably N-CH2-CH2-OH; b) aminating the at least one first intermediate (I1) with at least one of ammonia, primary and secondary amines HNR'R" with R' being H, methyl, ethyl, propyl or isopropyl and R" being H, methyl, ethyl, propyl or isopropyl, or mixtures thereof, to form at least one polyamine compound (II).