Benzylated Mannich Base Curing Agents for Epoxy Resins

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Solution Overview

Problem

Current epoxy resin systems face challenges with slow curing rates at low temperatures and compatibility issues between amine curing agents and epoxy resins, leading to defects like blush and exudate, especially in cold and humid conditions, which affect the performance and appearance of coatings.

Innovation Solution

The development of benzylated Mannich base compositions that are miscible with epoxy resins, providing faster curing rates and improved compatibility, and are free from residual phenol, thus enhancing the properties of cured systems and reducing VOC usage.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If low molecular weight liquid epoxy resins are used to comply with VOC regulations, then VOC content is reduced, but curing rate becomes slow especially at low temperatures

Engineering Contradiction:
ImproveVOC contentVSAvoidcuring rate
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent modifies the chemical structure of the curing agent by introducing benzyl groups and selecting specific polyamine structures (polyethylene polyamine, polypropylene polyamine) to change the reaction kinetics parameters, enabling fast curing at low temperatures while maintaining compatibility with solvent-free epoxy systems

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite curing system combining benzylated Mannich base compounds with specific polyamines, achieving synergistic effects that simultaneously provide fast curing rate, low temperature reactivity, and compatibility with liquid epoxy resins

Inventive Principle:
Principle #40Composite materials

2Object-affected harmful factors

If amine curing agents are used with liquid epoxy resins, then VOC regulations are met, but phase separation occurs leading to blush and exudate defects

Engineering Contradiction:
Improvecoating defectsVSAvoidcompatibility
Core Design Contradiction:
Object-affected harmful factorsVSStability of the object's composition

Solution Approach 1:

The patent changes the molecular parameters of the curing agent by benzylating Mannich bases and selecting specific polyamine structures, which modifies the polarity and solubility characteristics to match liquid epoxy resins, preventing phase separation

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention achieves homogeneous mixing and compatibility between the curing agent and liquid epoxy resin by carefully selecting polyamine structures and benzylation degrees, ensuring single-phase composition that prevents blush and exudate formation

Inventive Principle:
Principle #33Homogeneity

3Productivity

If conventional Mannich bases are used as curing agents, then some curing activity is achieved, but residual phenol remains causing environmental and safety concerns

Engineering Contradiction:
Improvecuring activityVSAvoidresidual phenol
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent removes the harmful residual phenol component from the Mannich base structure through selective synthesis and purification, retaining only the beneficial curing functionality while eliminating the environmental and safety hazards

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention converts the traditional Mannich base synthesis that produces harmful phenol residues into a modified process that eliminates phenol while maintaining or improving curing performance, turning a harmful byproduct issue into a benefit of the new composition

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

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 benzylated Mannich base compositions facilitate faster curing, improved compatibility, and reduced VOC usage, resulting in coatings with better adhesion, clarity, and resistance to carbamation, while maintaining environmental and worker safety.

Implementation Method 1

The curing process is the chemical reaction of the epoxide groups in the epoxy resins and the reactive groups in the curing agents

Methodology Applied
Scientific EffectAmine-epoxide reaction: Chemical Bonding

Implementation Method 2

The benzylated Mannich base compositions facilitate faster curing, improved compatibility

Methodology Applied
Scientific EffectChemical reaction rate enhancement: Catalysis

Data Source

PatentEP3420016B1Benzylated mannich base curing agents, compositions, and methods
Publication Date: 2025.01.15 EVONIK OPERATIONS GMBH
  • EP3420016B1 patent drawing
  • EP3420016B1 patent drawing
  • EP3420016B1 patent drawing

AI summary

Compositions and curing agents comprising a benzylated Mannich base composition. The benzylated Mannich base composition includes a reaction product of (a) a substituted phenolic compound having at least one substituent of formula (I): (I) wherein R1 is each independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R2 is hydrogen, methyl, ethyl or phenyl, with (b) a benzylated polyalkylene polyamine (II): (II) wherein RA is substituted or unsubstituted benzyl; RB is each independently RA, or a hydrogen atom, or a group selected from C1 - C16 linear, cyclic, and branched alkyl, alkenyl, and alkaryl groups; X, Y, and Z are independently selected from C2-C10 alkylene, and cycloalkylene groups; y is an integer from 0 to 7, and z is an integer from 0 to 4; and, optionally, (c) a multifunctional amine. Amine-epoxy compositions and articles produced from these compositions are also disclosed.