Amine Adduct Dispersants for High-Solids Coatings

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Solution Overview

Problem

Existing dispersants for paints and plastics face limitations in universality and effectiveness, particularly in reducing viscosity in highly filled systems, leading to issues like increased viscosity, color drift, and loss of gloss due to inadequate dispersion and reagglomeration of solid particles.

Innovation Solution

A process for producing an amine adduct by reacting a polyamine with an epoxide or oxetane, followed by a lactone or hydroxycarboxylic acid, ensuring at least 50 mol% of amino groups are converted, resulting in a product with improved stability and compatibility, which acts as a dispersant with reduced side reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional dispersants are used to disperse solids in liquid systems, then dispersion is achieved, but viscosity reduction is insufficient in highly filled systems

Engineering Contradiction:
Improvesolids concentrationVSAvoidviscosity
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameters of the dispersant by synthesizing amine adducts with specific molecular structures containing both hydrophobic and hydrophilic groups. These modified dispersants achieve superior viscosity reduction at high solids concentrations (above 60 wt%) compared to conventional dispersants, resolving the contradiction between increasing solids content and maintaining low viscosity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The amine adduct dispersants function as composite molecules combining different functional groups (hydrophobic hydrocarbon chains and hydrophilic polar groups) that can simultaneously interact with both organic binders and inorganic solids. This composite structure enables effective dispersion and viscosity control in highly filled systems where conventional single-function dispersants fail

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If polyesters are produced in a separate step by polymerization reaction, then linear monofunctional polyesters are obtained, but the amino groups in the core region of highly branched polyamines remain inaccessible

Engineering Contradiction:
Improvepolyester structure controlVSAvoidamine group accessibility
Core Design Contradiction:
Manufacturing precisionVSAdaptability or versatility

Solution Approach 1:

The patent segments the modification process into two distinct steps: first modifying the accessible outer amino groups with epoxide/oxetane, then modifying the previously inaccessible core amino groups with lactone/hydroxycarboxylic acid. This segmentation enables complete utilization of all amino groups in highly branched polyamines, achieving at least 50 mol% conversion and eliminating residual reactive groups that cause stability problems

Inventive Principle:
Principle #1Segmentation

3Ease of manufacture

If amine adducts contain reactive primary or secondary amino groups, then addition to polyesters occurs, but side reactions occur leading to undesirable stability problems

Engineering Contradiction:
Improveaddition reaction efficiencyVSAvoidstorage stability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent converts the potentially harmful reactive amino groups into beneficial functional groups by reacting them with epoxide/oxetane and lactone/hydroxycarboxylic acid. The reactive amino groups that would otherwise cause unwanted side reactions are transformed into stable amine adduct structures with controlled reactivity, eliminating stability problems while maintaining desired dispersion functionality

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

4Quantity of substance

If dispersants are applied in small quantities, then cost is reduced, but adequate dispersion and viscosity reduction are not achieved in highly filled systems

Engineering Contradiction:
Improvedispersant dosageVSAvoiddispersion effectiveness
Core Design Contradiction:
Quantity of substanceVSProductivity

Solution Approach 1:

The patent changes the effectiveness parameter of the dispersant through molecular structure modification. The amine adduct dispersants achieve significantly higher dispersion effectiveness and viscosity reduction per unit dosage compared to conventional dispersants, enabling adequate performance even at low concentrations in highly filled systems with above 60 wt% solids content

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 amine adducts demonstrate enhanced storage stability, lower viscosity in solid dispersions, improved compatibility with solvents and binders, and reduced tendency for reagglomeration, enabling higher solids concentrations and maintaining gloss in coatings.

Implementation Method 1

the monomer (C) reacts with one of the amino groups (A+) of the polyamine (A) by ring opening and formation of a hydroxyl group (H+), additionally forming either a carbon-nitrogen bond or a urethane bond

Methodology Applied
Scientific EffectRing opening reaction: Chemical Bonding

Implementation Method 2

In the first step, the hydroxyl groups (H+) formed are converted to ester groups, wherein the monomer (B) is selected such that either a terminal hydroxyl group (H++) is additionally formed during its conversion

Methodology Applied
Scientific EffectEsterification reaction: Chemical Bonding

Implementation Method 3

in the second step reacts in such a way that any amino groups (A+) not reacted in the first step are converted to amide groups

Methodology Applied
Scientific EffectAmide formation reaction: Chemical Bonding

Data Source

PatentEP3512899B1Polyester modified amino adducts
Publication Date: 2021.11.10 BYK CHEMIE GMBH
  • EP3512899B1 patent drawing
  • EP3512899B1 patent drawing

AI summary

The invention relates to processes for producing an amine adduct in which in a 1st step a polyamine (A) is reacted with a monomer (C) in the form of an epoxide, an oxetane or a cyclic carbonate to afford an (intermediate) product (AC) which in a subsequent 2nd step is reacted with a monomer (B) in the form of a lactone, an acyclic hydroxycarboxylic acid or a hydroxy-functional acyclic ester to afford a (descendant) product (ACB), wherein the polyamine (A) in each case comprises at least three amino groups (A+) selected from primary and secondary amino groups and each capable of reaction with the monomers (C) and (B), the monomer (C) contains no ester groups, no carboxyl groups and no primary or secondary amino groups and in the 1st step with ring opening and formation of a hydroxyl group (H+) reacts with one of the amino groups (A+) of the polyamine (A) with additional formation of either a carbon-nitrogen bond or a urethane bond, the monomer (B) contains no primary or secondary amino groups, has a molecular weight of 90-300 g/mol and in the 2nd step reacts in such a way that any amino groups (A+) not converted in the 1st step are converted into amide groups and hydroxyl groups (H+) formed in the 1st step are converted into ester groups, wherein the monomer (B) is chosen in such a way that either in the conversion thereof a terminal hydroxyl group (H++) is additionally formed or that the monomer (B) itself already has a terminal hydroxyl group (H++) and that via the terminal hydroxyl groups (H++) with formation of (poly)ester groups a further addition of the monomer (B) is effected, wherein the process parameters are chosen such that in the 1st step and in the 2nd step altogether at least 50 mol% of the amino groups (A+) are converted.