Bio-Based Amido-Amine Hardener for Low-Temperature Epoxy Curing
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Solution Overview
Problem
Existing crosslinking agents for epoxy resins, such as polyamides and phenolic-derived Mannich bases, face limitations in low-temperature curing, toxicity, and regulatory issues, reducing their availability and versatility.
Innovation Solution
Development of amide Mannich bases formed through amidation and Mannich reactions using aromatic or heteroaromatic acids and polyamines, creating compounds with nucleophilic amine groups suitable for epoxy resin curing, avoiding phenol-derived materials.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If phenolic-derived Mannich bases are used as crosslinking agents, then compatibility with epoxy resins and cure speed are improved, but toxicity and environmental issues worsen
Solution Approach 1:
The invention extracts and removes the harmful phenolic component from the Mannich base structure. Instead of using phenol as the starting material, the patent employs alternative non-phenolic compounds that maintain the beneficial curing properties while eliminating toxicity and environmental concerns associated with free phenol
Solution Approach 2:
The patent creates composite curing agents by combining multiple functional components in the Mannich base structure, integrating the reactive amine groups needed for epoxy curing with safe, non-phenolic backbone structures. This composite approach maintains high cure speed and compatibility while avoiding phenolic toxicity
2Ease of operation
If polyamides are used as curing agents, then processability is improved, but low-temperature curing capability deteriorates
Solution Approach 1:
The invention modifies the chemical structure parameters of the curing agent by designing Mannich bases with specific amine group configurations and molecular weights that enable low-temperature reactivity. The patent adjusts parameters such as the type of amine used in the Mannich reaction and the structure of the backbone compound to achieve both good processability and low-temperature curing capability
3Adaptability or versatility
If conventional amine curing agents are used, then versatility in curing temperatures is improved, but toxicity worsens
Solution Approach 1:
The invention removes toxic aromatic amine components from the curing agent structure and replaces them with safe aliphatic or cycloaliphatic amine-based Mannich bases. This extraction of harmful aromatic structures maintains the versatile temperature-dependent curing behavior while eliminating toxicity concerns
Solution Approach 2:
The patent changes the chemical composition parameters by using saturated aliphatic and cycloaliphatic amine structures instead of aromatic amines. This parameter change preserves the ability to cure across a broad temperature range while significantly reducing or eliminating toxicity associated with aromatic amine exposure
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 amide Mannich bases provide high process performance, broad compatibility with epoxy resins, and eliminate toxicity and environmental issues, enabling effective low-temperature curing and crosslinking.
Implementation Method 1
An aromatic or heteroaromatic acid group or analogue thereof undergoes amidation to form an amide
Implementation Method 2
as well as the Mannich reaction to form a Mannich base
Implementation Method 3
resulting in an amide Mannich base with at least one nucleophilic amine group side chain suitable for reaction with the epoxide group of an epoxy resin
Data Source
Figure 1~2
AI summary
The invention relates to a class of amido-amines useful as curatives and having a high degree of biological based carbon content. In particular, the invention is directed to compounds comprising at least one amide group and at least one Mannich base, polymeric compounds comprising a repeating unit having at least one amide group and at least one Mannich base, a resin curative composition comprising such compounds, processes for preparing them and uses thereof. In one aspect, the present invention provides a compound of formula (1) below, wherein A, Y, Y1, Z, Z1, x, y, n, m, R and R1 are as defined herein.