Cyclocarbonate Polyurethane Adhesive for Food Packaging

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Solution Overview

Problem

Polyurethane-based adhesives used in flexible packaging often contain residual aromatic diisocyanates, leading to toxicity issues and instability, particularly during high-temperature sterilization processes, resulting in degradation of the adhesive joint and unsuitability for food packaging.

Innovation Solution

A two-component adhesive composition comprising cyclocarbonate-terminated polyurethane prepolymer and a diamine/polyamine mixture, with a specific molar ratio of primary amine functions to cyclocarbonate functions, which is free from residual polyisocyanates and exhibits improved thermal resistance and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If NCO terminated polyurethane adhesives are used to achieve good adhesion properties, then adhesion performance is improved, but residual aromatic diisocyanate content increases leading to toxicity and stability problems

Engineering Contradiction:
Improveadhesion performanceVSAvoidtoxicity from residual diisocyanate
Core Design Contradiction:
StrengthVSObject-affected harmful factors

Solution Approach 1:

The harmful NCO groups are extracted and transformed through reaction with cyclocarbonate compounds. The patent converts the toxic isocyanate functionality into non-toxic cyclocarbonate-terminated polyurethane, eliminating residual diisocyanate while preserving adhesion properties through the resulting adhesive composition.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The chemical structure and properties of the polyurethane are changed by modifying the terminal groups from NCO to cyclocarbonate. This parameter change transforms the toxic, reactive NCO groups into stable, non-toxic cyclocarbonate groups, fundamentally altering the safety and stability parameters while maintaining adhesive performance.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If polyurethane compositions with low MDI content are used to reduce toxicity, then residual diisocyanate content is reduced, but viscosity increases and stability over time deteriorates

Engineering Contradiction:
Improveresidual diisocyanate contentVSAvoidviscosity stability over time
Core Design Contradiction:
Object-affected harmful factorsVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameters of the polyurethane by introducing cyclocarbonate terminal groups, which fundamentally alter the molecular weight distribution and intermolecular interactions. This parameter change resolves the viscosity-stability issue by creating a molecular structure that maintains flow properties while improving temporal stability.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If conventional adhesives are used for multilayer packaging, then lamination process is simple, but thermal resistance during sterilization is insufficient leading to adhesive joint degradation

Engineering Contradiction:
Improvelamination process simplicityVSAvoidthermal resistance during sterilization
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent creates a composite adhesive system by combining cyclocarbonate-terminated polyurethane with diamine/polyamine hardeners. This composite material approach provides both the simplicity of a two-component mixing process and superior thermal resistance, as the crosslinked network structure formed upon hardening delivers excellent sterilization resistance while maintaining ease of manufacture.

Inventive Principle:
Principle #40Composite materials

4Strength

If aromatic diisocyanate-based polyurethanes are used to achieve good adhesion, then bonding strength is improved, but chemical resistance and food safety are compromised

Engineering Contradiction:
Improvebonding strengthVSAvoidchemical resistance and food safety
Core Design Contradiction:
StrengthVSObject-generated harmful factors

Solution Approach 1:

The harmful aromatic diisocyanate component is extracted and replaced with aliphatic or aromatic diisocyanates used only as intermediates that are fully consumed in the synthesis. The final adhesive contains no residual aromatic diisocyanate, eliminating toxicity while maintaining bonding strength through the cyclocarbonate-terminated polyurethane structure.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The chemical composition parameters are changed by eliminating aromatic diisocyanate residues and introducing cyclocarbonate terminal groups. This parameter change improves food safety and chemical resistance while preserving bonding strength, as the cyclocarbonate groups provide reactive functionality for crosslinking without the toxicological concerns of aromatic diisocyanates.

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 adhesive composition provides enhanced thermal resistance and stability, ensuring the multilayer structure's integrity during sterilization, making it suitable for food packaging without toxicity risks.

Implementation Method 1

preparing an NCO-terminated polyurethane prepolymer by a polyaddition reaction: i) of at least one polyisocyanate chosen from diisocyanates and triisocyanates, ii) with at least one polyol chosen from polyether polyols and polyester polyols

Methodology Applied
Scientific EffectPolyaddition reaction: Chemical Bonding

Implementation Method 2

The adhesive composition consists of composition A comprising at least one cyclocarbonate-terminated polyurethane prepolymer and composition B comprising at least one diamine and at least one polyamine

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Data Source

PatentEP3484973B1Adhesive dual-component composition based on polyurethane
Publication Date: 2020.12.23 BOSTIK SA(FR)
  • EP3484973B1 patent drawing
  • EP3484973B1 patent drawing
  • EP3484973B1 patent drawing

AI summary

The invention relates to an adhesive dual-component composition comprising a composition A based on a polyurethane prepolymer with cyclocarbonate terminations and a composition B based on a mixture comprising at least one diamine B1 comprising only two primary amine groups of the -CH2-NH2 type and at least one polyamine B2 comprising at least three primary amine groups of the -CH2-NH2 type. The invention also relates to a multilayer structure produced from the adhesive composition according to the invention and to the method for the production thereof.