Modified Polyamide Curing Agents for Epoxy Resins

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Solution Overview

Problem

Current polyamide curing agents for epoxy resins face challenges such as high viscosity, requiring high solvent levels, and environmental regulations limiting solvent use, while also suffering from issues like heat instability and undesirable byproducts, which affect the performance and cost-effectiveness of coatings and adhesives.

Innovation Solution

The development of polyamides and amidoamines formed from selectively modified amines, specifically through alkylation or benzylation of polyamines, which react with fatty acids to create curing agents with lower viscosity, reduced induction time, and improved miscibility with epoxy resins, enabling transparent mixing and enhanced surface appearance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional polyamide curing agents are used, then epoxy resins can be cured effectively, but the viscosity is high requiring high solvent levels which conflicts with environmental regulations

Engineering Contradiction:
Improvecuring effectivenessVSAvoidsolvent content
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the amine component through selective benzylation or alkylation. This changes the molecular parameters (adding aromatic or aliphatic groups) which reduces the viscosity of the final polyamide curing agent, thereby reducing the solvent content needed while maintaining curing effectiveness.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite curing agents by combining benzylated or alkylated polyamines with fatty acids. This composite approach produces a curing agent with optimized properties - the modified amine provides lower viscosity and reduced solvent requirements, while the fatty acid component maintains the curing functionality.

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If benzylated amine is used to reduce viscosity, then miscibility with epoxy resin improves, but undesirable chlorine byproducts are formed that must be removed

Engineering Contradiction:
ImprovemiscibilityVSAvoidchlorine byproducts
Core Design Contradiction:
Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The patent extracts the harmful chlorine-containing benzyl chloride reagent from the process and replaces it with alternative benzylating agents (benzaldehyde, toluene) or alkylating agents that do not produce chlorine byproducts, thereby eliminating the need for byproduct removal steps.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent uses simpler, more environmentally friendly reagents (benzaldehyde, toluene, fatty acids) that are easier to handle and do not require complex purification steps, replacing the more problematic benzyl chloride reagent.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Adaptability or versatility

If styrenated product is used, then some polyamidoamines can be prepared, but the product is not heat stable and retro reaction occurs during manufacture

Engineering Contradiction:
Improvepolyamidoamine preparationVSAvoidheat stability
Core Design Contradiction:
Adaptability or versatilityVSStability of the object's composition

Solution Approach 1:

The patent converts the potential instability issue into a benefit by carefully controlling the degree of benzylation or alkylation and selecting appropriate fatty acid components, which stabilizes the product against retro-reaction while maintaining the desired polyamidoamine structure and properties.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

4Object-affected harmful factors

If viscosity is reduced by using modified amines, then solvent levels decrease, but the amine hydrogen equivalent weight also decreases affecting formulation

Engineering Contradiction:
Improvesolvent contentVSAvoidamine hydrogen equivalent weight
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by carefully selecting the degree of benzylation or alkylation and the molecular weight of the fatty acid components to balance two opposing parameters: reducing viscosity (to lower solvent content) while maintaining adequate amine hydrogen equivalent weight (for proper formulation and curing stoichiometry).

Inventive Principle:
Principle #35Parameter changes

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 selectively modified polyamide curing agents achieve lower viscosity, longer pot life, and improved surface properties, including high gloss and hardness, while reducing solvent content and compliance with environmental regulations, making them suitable for various industrial applications.

Implementation Method 1

The polyamides and amidoamine curing agents are formed from the reaction of a selectively modified amine component with a fatty acid component

Methodology Applied
Scientific EffectCondensation reaction:

Data Source

PatentEP2686364A2Polyamides and amidoamines from selectively modified amine amines
Publication Date: 2014.01.22 EVONIK OPERATIONS GMBH

AI summary

The present disclosure provides polyamides and amidoamine curing agents including the reaction product of (1) a modified amine component comprising at least one multifunctional amine of structure 1: wherein R1 is selected from C1 - C16 linear, cyclic, and branched alkyl, alkenyl, and alkaryl groups; R2 and R4 are hydrogen, R3 is R1 or hydrogen, X, Y, and Z are independently selected from C2 - C10 alkylene, hexylene and cycloalkylene groups, n=0, 1, 2, 3, 4, 5, 6, or 7; and (2) a fatty acid component. Exemplary fatty acid components include at least one of monomer fatty acids, dimer fatty acids, trimer fatty acids, polymer fatty acids, esters of monomer, dimer, trimer, and polymer fatty acids and combinations thereof. The method for making the curing agents and articles formed therefrom are also disclosed.