Cyclic Anhydride Crosslinkers for Formaldehyde-Free Packaging Coatings

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Solution Overview

Problem

Existing coatings often contain formaldehyde, which industries seek to reduce or eliminate due to health and environmental concerns, and there is a need for formaldehyde-free thermoset coatings that provide protective and decorative qualities.

Innovation Solution

A coating composition comprising a film-forming resin with active hydrogen atoms and a crosslinking material formed from a reaction mixture with ≥70% cyclic unsaturated acid anhydride and/or its diacid derivative, which reacts with alcohol, amine, thiol, or water to create a crosslinking material with an acid number of at least 100 mg KOH/g, eliminating the need for formaldehyde-based crosslinkers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If formaldehyde-based crosslinkers are used, then crosslinking effectiveness is achieved, but harmful formaldehyde is released causing health and environmental issues

Engineering Contradiction:
Improvecrosslinking effectivenessVSAvoidformaldehyde release
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical parameters of the crosslinking system by replacing formaldehyde-based crosslinkers with cyclic unsaturated acid anhydrides (≥70% by weight) that undergo polycondensation reactions. This parameter change eliminates formaldehyde release while maintaining crosslinking effectiveness through alternative reaction mechanisms involving alcohol, amine, thiol, or water functional groups.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the harmful formaldehyde byproduct into a beneficial formaldehyde-free system by using cyclic unsaturated acid anhydrides as crosslinking materials. The polycondensation reaction of these anhydrides with functional groups (alcohol, amine, thiol, or water) produces crosslinked networks without generating harmful formaldehyde, thus transforming a harmful process into a benign one.

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

2Duration of action of stationary object

If conventional crosslinking materials are used, then coating durability is improved, but the coating contains harmful formaldehyde

Engineering Contradiction:
Improvecoating durabilityVSAvoidformaldehyde content
Core Design Contradiction:
Duration of action of stationary objectVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters of the crosslinking material from formaldehyde-based compounds to cyclic unsaturated acid anhydrides with ≥70% content. This parameter change enables the coating to achieve durable crosslinked networks through polycondensation reactions while eliminating formaldehyde content, thus improving both durability and safety.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention uses composite crosslinking materials formed by the reaction product of cyclic unsaturated acid anhydride with functional groups (alcohol, amine, thiol, or water). This composite approach creates crosslinked networks that provide long-term durability while being free of harmful formaldehyde, combining the benefits of durability with environmental safety.

Inventive Principle:
Principle #40Composite materials

3Object-generated harmful factors

If formaldehyde-free crosslinking materials are used, then health and environmental safety is improved, but crosslinking performance may be compromised

Engineering Contradiction:
Improveformaldehyde-free compositionVSAvoidcrosslinking performance
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The invention changes the chemical parameters by using cyclic unsaturated acid anhydrides (≥70% by weight) with controlled molecular weight and functionality. These parameter changes enable the crosslinking material to achieve sufficient crosslinking density and network formation without formaldehyde, thereby maintaining crosslinking performance while ensuring formaldehyde-free composition.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention applies local quality by ensuring that the cyclic unsaturated acid anhydride component has specific functional group distributions and reactivity characteristics. This local quality control at the molecular level ensures that the crosslinking performance is maintained in the formaldehyde-free system through optimized reaction kinetics and crosslinking density.

Inventive Principle:
Principle #3Local quality

4Reliability

If high acid number crosslinking material (≥100 mg KOH/g) is used, then acid resistance is improved, but formulation complexity increases

Engineering Contradiction:
Improveacid resistanceVSAvoidformulation complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention changes the acid number parameter of the crosslinking material to ≥100 mg KOH/g by using cyclic unsaturated acid anhydrides with appropriate functionality. This parameter change provides the necessary acid resistance for packaging applications while the systematic approach to formulation (using ≥70% cyclic unsaturated acid anhydride with standard functional groups) keeps the complexity manageable through standardized reaction patterns.

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 solution provides a formaldehyde-free coating with effective crosslinking properties, ensuring suitable acid resistance and flexibility for packaging applications while maintaining decorative qualities.

Implementation Method 1

a crosslinking material comprising the reaction product of a reaction mixture comprising: (i) ≥70% by weight of a cyclic unsaturated acid anhydride and/or diacid derivative thereof by total solid weight of the monomers from which the crosslinking material is formed; (ii) optionally, an ethylenically unsaturated monomer; and (iii) optionally, an alcohol, amine, thiol and/or water, wherein at least a portion of the cyclic unsaturated acid anhydride and/or diacid derivative thereof is reacted with the alcohol, amine, thiol and/or water

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

a crosslinking material operable to crosslink the functional group having an active hydrogen atom on the film-forming resin

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Data Source

PatentEP4126989B1Coating composition comprising a film-forming resin and a crosslinking material
Publication Date: 2025.07.09 PPG INDUSTRIES OHIO INC
  • EP4126989B1 patent drawing

AI summary

A crosslinking material, the crosslinking material comprising the reaction product of a reaction mixture comprising: (ii) ≥70% by weight of a cyclic unsaturated acid anhydride and/or diacid derivative thereof by total solid weight of the monomers from which the crosslinking material is formed; (ii) optionally, an ethylenically unsaturated monomer; and (iii) optionally, an alcohol, amine, thiol and/or water, wherein at least a portion of the cyclic unsaturated acid anhydride and/or diacid derivative thereof is reacted with the alcohol, amine, thiol and/or water, when present; and wherein the crosslinking material has an acid number of at least 100 mg KOH/g.