Beta-Ketoacetate Polyester Resins for Phenolic Crosslinking

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Solution Overview

Problem

Conventional polyester resins used in thermosetting coatings for metal food and beverage containers lack adequate crosslinking density with phenolic resins, resulting in coatings with poor solvent resistance and inadequate properties for food contact applications.

Innovation Solution

The use of curable polyester resins containing beta-ketoacetate moieties, which react effectively with resole phenolic resins to achieve enhanced crosslinking density, resulting in coatings with improved solvent resistance and desirable properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional polyester resins are used with phenolic resins, then the coating system is simple and widely available, but the crosslinking density is insufficient resulting in poor solvent resistance

Engineering Contradiction:

Improvesolvent resistanceVSAvoidcoating composition complexity

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the chemical structure of polyester resin by introducing beta-ketoacetate moieties, changing the reactivity parameters to enable effective crosslinking with phenolic resins. This structural modification transforms the polyester from having poor reactivity to having high reactivity with phenolic resins, achieving adequate crosslinking density and solvent resistance

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite coating system combining modified polyester resin containing beta-ketoacetate groups with phenolic resin. This composite material leverages the complementary properties of both components: the flexibility and adhesion of polyester combined with the crosslinking capability of phenolic resin, achieving a balance of mechanical properties and chemical resistance

Inventive Principle:

Principle #40Composite materials

2Reliability

If epoxy and phenolic resin combinations are used, then excellent coating properties are achieved, but the system contains BPA and BADGE which are being phased out in food contact applications

Engineering Contradiction:

Improvecoating performanceVSAvoidBPA and BADGE presence

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces the problematic epoxy resin component with a modified polyester resin that achieves similar performance through beta-ketoacetate crosslinking. This substitution eliminates BPA and BADGE from the formulation while maintaining the necessary coating properties for food contact applications

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the chemical composition parameters of the coating system by substituting epoxy resin with beta-ketoacetate modified polyester resin. This parameter change maintains the crosslinking mechanism and coating performance while removing harmful substances from the formulation

Inventive Principle:

Principle #35Parameter changes

3Reliability

If crosslinking between conventional polyester and phenolic resin is increased, then solvent resistance improves, but the reactivity under curing conditions remains insufficient

Engineering Contradiction:

Improvecrosslinking densityVSAvoidcuring reactivity

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent introduces beta-ketoacetate moieties into the polyester resin structure, which fundamentally changes the reactivity parameters. The beta-ketoacetate groups are highly reactive with phenolic resins under curing conditions, enabling adequate crosslinking density to be achieved without requiring extreme curing conditions or catalysts

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 combination of beta-ketoacetate-containing polyester resins with resole phenolic resins provides coatings with excellent solvent resistance and improved crosslinking density, addressing the limitations of conventional systems and ensuring effective protection for food contact surfaces.

Implementation Method 1

crosslinking between common polyester and phenolic resin is too poor to provide adequate properties... curable polyester resins containing beta-ketoacetate moieties, which react effectively with resole phenolic resins to achieve enhanced crosslinking density

Methodology Applied

Scientific EffectChemical Bonding: Chemical Bonding

Data Source

PatentUS9598602B2Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds

Publication Date: 2017.03.21 EASTMAN CHEM CO

AI summary

A thermosetting composition having:I. a curable polyester resin containing beta-ketoacetate moieties without vinyl unsaturations; andII. a phenolic resin having at least one methylol group.The curable polyester resin can be made by reacting a polyester resin with a compound containing a beta-ketoacetate moiety that does not contain a vinyl unsaturation such as alkyl acetoacetate compounds or diketene compounds.The curable polyester resin can be dispersed in water or dissolved in a solvent and is suitable for waterborne or solventborne coating compositions. Phenolic based crosslinking coating compositions that contain these curable polyester resins cure well with phenolic resin crosslinking compounds.