Recycled PET Methacrylated Compounds for Coatings

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Solution Overview

Problem

Current methods for producing (meth)acrylated compounds from recycled PET result in low recycled content and inadequate pigment wetting and ink-water balance in energy curable coating compositions and inks.

Innovation Solution

A process involving the depolymerization of thermoplastic polyester with polyhydric alcohols and triglycerides, followed by reaction with fatty acids and (meth)acrylating compounds, to produce (meth)acrylated compounds with a higher PET content and improved pigment wetting and ink-water balance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If glycolysis of PET is used for depolymerization with high glycol/PET molar ratio (at least 2), then the depolymerization reaction proceeds efficiently, but the recycled PET content in the final product becomes low

Engineering Contradiction:
Improvedepolymerization efficiencyVSAvoidrecycled PET content
Core Design Contradiction:
Ease of manufactureVSQuantity of substance

Solution Approach 1:

The invention changes the key parameter of glycol/PET molar ratio from the conventional at least 2 to less than 2 (specifically 0.5-1.5), which fundamentally alters the reaction pathway and product distribution to achieve both efficient depolymerization and high recycled content retention

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If conventional polyester acrylates are used in energy curable coating compositions, then the coating process is simple, but pigment wetting and ink-water balance are inadequate

Engineering Contradiction:
Improvecoating process simplicityVSAvoidpigment wetting and ink-water balance
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The invention creates composite (meth)acrylated compounds that integrate recycled PET segments with fatty acid and triglyceride moieties, producing a multi-functional material that simultaneously provides good processability and superior pigment wetting and ink-water balance properties

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention introduces specific functional groups (fatty acid chains and triglyceride structures) at localized positions within the polymer chain to enhance pigment wetting and ink-water balance, while maintaining the overall simplicity of the coating application process

Inventive Principle:
Principle #3Local quality

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 process achieves (meth)acrylated compounds with a higher PET content and enhanced pigment wetting and ink-water balance, facilitating their incorporation into coating compositions and inks with improved performance.

Implementation Method 1

Reacting a thermoplastic polyester with (a1) at least one polyhydric alcohol... to obtain a depolymerization product A

Methodology Applied
Scientific EffectDepolymerization: Hydrolysis

Implementation Method 2

Reacting the depolymerization product A with (b1) at least one fatty acid and/or (b2) at least one polybasic carboxylic acid... to provide a polyester polyol B

Methodology Applied
Scientific EffectCondensation reaction: Chemical Bonding

Implementation Method 3

Reacting the polyester polyol B with at least one (meth)acrylating compound (c) to provide a methacrylated compound (I)

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Data Source

PatentUS11267949B2(Meth)acrylated compounds based on recycled PET
Publication Date: 2022.03.08 ALLNEX BELGIUM SA

AI summary

The present invention relates to a process for preparing a polyester (meth)acrylate resin (I), said process comprising the steps of: (a) Reacting a thermoplastic polyester with (a1) at least one polyhydric alcohol and, optionally, with (a2) at least one triglyceride, wherein the molar ratio of triglyceride to thermoplastic polyester is between 0 and 0.3, and the molar ratio of polyhydric alcohol to thermoplastic polyester is at most 1.9 to obtain a depolymerization product A that has a hydroxyl number within the range of from 200 to 800 mg KOH/g; (b) Reacting the depolymerization product A with (b1) at least one fatty acid and/or (b2) at least one polybasic carboxylic acid and, optionally, with (b3) at least one polyhydric alcohol to provide a polyester polyol B; (c) Reacting the polyester polyol B with (c) at least one (meth)acrylating compound to provide a (meth)acrylated compound (I), wherein the weight ratio of fatty acid (b1) to the depolymerization product A is between 0 and 0.6, wherein the weight ratio of polybasic carboxylic acid (b2) to the depolymerization product A is less than 0.3, wherein the weight ratio of (meth)acrylating compounds (c) to the depolymerization product A is between 0.1 and 0.8, and wherein the (meth)acrylated compound (I) that is obtained has a number average molecular weight (Mn) of between 500 and 5,000 Dalton. Typically PET is used as starting material. Typically compounds (I) of the invention have a PET content of at least 15 wt %, preferably at least 25 wt %. The present invention also relates to (meth)acrylated compounds (I) thus obtained and to coating compositions and inks based upon these materials. Materials of the invention allow the use of a high amount of PET waste. Inks and coatings prepared from these materials exhibit an excellent pigment wetting and/or ink-water balance.