Aspartate-Terminated Prepolymers for Adhesive Applications

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Solution Overview

Problem

Conventional two-component polyurethane adhesive compositions for flexible packaging face challenges in achieving sufficient mechanical strength and preventing primary aromatic amine migration, especially when exposed to elevated temperatures, while maintaining fast cure times.

Innovation Solution

The development of aspartate-terminated prepolymers, which are reaction products of aliphatic NCO-terminated prepolymers and specific compounds, combined with aliphatic polyisocyanates at optimized equivalent ratios, to form adhesives that minimize primary aromatic amine migration and ensure rapid curing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If aromatic polyisocyanates are used in two-component polyurethane adhesive compositions, then fast cure time is achieved, but primary aromatic amine migration occurs at elevated temperatures

Engineering Contradiction:
Improvecure timeVSAvoidprimary aromatic amine migration
Core Design Contradiction:
SpeedVSObject-generated harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters by using aliphatic polyisocyanates instead of aromatic polyisocyanates, and employs specific polyol components with controlled molecular weights and functionalities. This parameter change eliminates the formation of primary aromatic amines while maintaining acceptable cure characteristics through optimized component selection and ratios.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The adhesive composition uses a composite approach by combining aliphatic polyisocyanate with specific polyol components (including polyether polyols and polyester polyols) to create a multi-component system that achieves both safety (no PAA migration) and performance (adequate cure speed and mechanical properties).

Inventive Principle:
Principle #40Composite materials

2Object-generated harmful factors

If aliphatic polyisocyanates are used to eliminate primary aromatic amine migration, then health and safety requirements are met, but cure time becomes much slower

Engineering Contradiction:
Improveprimary aromatic amine migrationVSAvoidcure time
Core Design Contradiction:
Object-generated harmful factorsVSLoss of time

Solution Approach 1:

The invention optimizes physical parameters including viscosity, molecular weight, and functionality of the polyol components to compensate for the slower reactivity of aliphatic polyisocyanates. By selecting polyols with appropriate characteristics and controlling the NCO:OH ratio, the system achieves practical cure speeds despite using safer aliphatic isocyanates.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a substitute system that copies the functional benefits of aromatic polyisocyanate-based adhesives (fast cure, strong bonding) using aliphatic polyisocyanates combined with specifically selected polyol components, thereby achieving similar performance without the harmful byproducts.

Inventive Principle:
Principle #26Copying

3Strength

If extended storage at elevated temperatures is used to complete curing, then mechanical strength is sufficient, but productivity and efficiency are reduced

Engineering Contradiction:
Improvemechanical strength of adhesive bondVSAvoidcuring efficiency
Core Design Contradiction:
StrengthVSProductivity

Solution Approach 1:

The adhesive formulation is designed to achieve adequate initial bond strength and mechanical properties within a practical time frame at moderate temperatures, eliminating the need for extended high-temperature storage. The component selection and ratios are optimized to provide sufficient reactivity and crosslinking density to achieve target performance without prolonged curing cycles.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention modifies the chemical composition parameters (isocyanate index, polyol molecular weight distribution, functionality ratios) to enhance the rate of polymerization and crosslinking, thereby achieving sufficient mechanical strength in a shorter time at lower temperatures, which improves productivity and reduces energy consumption.

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 adhesives with improved mechanical strength, reduced primary aromatic amine migration, and faster cure times, allowing for efficient lamination without the need for extended storage at elevated temperatures.

Implementation Method 1

an aspartate-terminated prepolymer which is a reaction product of a first reaction mixture including an aliphatic NCO-terminated prepolymer and a compound of formula (I)... combined at an NCO:NH equivalent ratio of 1:1.5 to 1:5

Methodology Applied
Scientific EffectIsocyanate-amine reaction: Chemical Bonding

Implementation Method 2

two component (2K) polyurethane adhesive compositions... After the adhesive is applied and the films are laminated, the films are wound onto large rolls and are stored at elevated temperatures for several days to allow for any unreacted polyisocyanate monomer to complete curing

Methodology Applied
Scientific EffectPolymerization: Chemical Bonding

Data Source

PatentEP4321549A1Low viscosity aspartate terminated prepolymers for adhesive applications
Publication Date: 2024.02.14 COVESTRO LLC
  • EP4321549A1 patent drawing
  • EP4321549A1 patent drawing
  • EP4321549A1 patent drawing

AI summary

An aspartate-terminated prepolymer can be a reaction product of a reaction mixture including an aliphatic NCO-terminated prepolymer having an NCO content of from 0.5% to 15% and a number average NCO functionality of < 2, and a compound according to formula (I) wherein, X represents a linear or branched aliphatic group obtained by removing amino groups from a linear or branched aliphatic polyamine, R1 and R2 are identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100°C or less, R3 and R4 are identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100°C or less, n represents an integer with a value of at least 2. The aliphatic NCO-terminated prepolymer can the compound according to formula I can be combined at an NCO:NH equivalent ratio of 1:1.5 to 1:5.