Isocyanate-Free Curable Compositions for Adhesion and Stability

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Solution Overview

Problem

Current isocyanate-based reactive compositions face challenges such as by-product generation, volatility, adhesion failures, and odor issues, while lacking isocyanate-free, low-temperature curability, and stability, particularly in applications requiring adhesion to isocyanate-containing substrates and moisture-impermeable materials.

Innovation Solution

Development of curable compositions comprising β-ketoester groups, aldehyde-functional curing agents, and primary or secondary amines, which allow for controlled curing and adhesion, eliminating the need for isocyanates and reducing volatile organic compounds, with the ability to adhere to various substrates and maintain stability at elevated temperatures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If isocyanate-based reactive compositions are used for coating and adhesive applications, then good adhesion and reactivity are achieved, but by-products are generated that cause volatility, adhesion failure, and unpleasant odor

Engineering Contradiction:
ImproveadhesionVSAvoidby-products
Core Design Contradiction:
StrengthVSObject-generated harmful factors

Solution Approach 1:

The invention extracts and eliminates the isocyanate component from the curable composition, replacing it with an isocyanate-free system comprising a polyol, a carboxylic acid, and a catalyst. This removal of the harmful isocyanate substance directly addresses the technical contradiction by maintaining adhesion functionality while eliminating by-product generation, volatility, and odor issues associated with isocyanate-based systems

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the chemical parameters of the curable composition by using a polyol with specific hydroxyl functionality (2-5 OH groups per molecule) and a carboxylic acid with specific carboxyl functionality (2-10 COOH groups per molecule), along with a catalyst system. This parameter change enables the formulation to achieve comparable adhesion and reactivity to isocyanate systems without generating harmful by-products, thus resolving the contradiction between adhesion strength and harmful by-product generation

Inventive Principle:
Principle #35Parameter changes

2Strength

If isocyanate-based systems are used to achieve good adhesion, then adhesion performance is improved, but thermal stability and UV stability are compromised

Engineering Contradiction:
ImproveadhesionVSAvoidthermal and UV stability
Core Design Contradiction:
StrengthVSStability of the object's composition

Solution Approach 1:

The invention creates a composite curable composition system combining a polyol, a carboxylic acid, and a catalyst in specific ratios. This composite material approach allows the formulation to achieve both good adhesion to substrates and enhanced thermal/UV stability, as the synergistic interaction between components provides resistance to environmental degradation while maintaining bonding strength, thus resolving the contradiction between adhesion and stability

Inventive Principle:
Principle #40Composite materials

3Productivity

If moisture-reactive isocyanate systems are used, then curing is achieved, but trace moisture in solvents initiates premature curing and reduces pot life

Engineering Contradiction:
Improvecuring rateVSAvoidpot life
Core Design Contradiction:
ProductivityVSDuration of action of stationary object

Solution Approach 1:

The invention introduces a catalyst as an intermediary substance that mediates the curing reaction between the polyol and carboxylic acid. This catalyst system enables controlled curing at room temperature or elevated temperatures without requiring moisture initiation, thereby preventing premature curing from trace moisture in solvents while maintaining efficient curing rates, thus resolving the contradiction between curing rate and pot life extension

Inventive Principle:
Principle #24Intermediary (Mediator)

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 compositions provide isocyanate-free, low-temperature curing with improved adhesion, reduced VOCs, and enhanced thermal and UV stability, enabling use on moisture-impermeable substrates and maintaining performance at service temperatures up to 130°C.

Implementation Method 1

the primary and/or secondary amines useful in the invention can act as catalyst and/or activating agent

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the timing of crosslinking and/or curing is controlled through certain combinations and/or under certain conditions

Methodology Applied
Scientific EffectCrosslinking: Chemical Bonding

Data Source

PatentEP3894477B1Controlled cure for compositions comprising acetoacetylated resins
Publication Date: 2025.01.15 EASTMAN CHEM CO
  • EP3894477B1 patent drawing
  • EP3894477B1 patent drawing

AI summary

This invention relates to a curable composition comprising: I. Component (I) comprising a resin having at least one functional group selected from the group consisting of β-ketoester and malonate functional groups; II. Component (II) comprising at least one curing agent having at least one aldehyde functional group, wherein said Component (II) is optionally latent; III. Component (III) comprising at least one amine, salts thereof, or combinations thereof; wherein before addition of Component (III), the reactivity of the composition is delayed by at least one of the following: (Sll)(a) at least one of said Components (I), (II), and (HI), or any reaction product thereof, or any combination thereof is a solid; or at least one of Components (II) or (III) or any combination thereof is insoluble in the resin under pot life conditions; or (lll)(b) at least one said amine is first reacted with at least one aldehyde, ketone, acetal or ketal, or mixtures thereof, optionally, to form a solid; (Ill)(c) at least one said amine is first reacted with a portion of Component (II), wherein the reaction product thereof is optionally reacted or combined subsequently with additional amounts of either or both of Components (II) and (III), and, prior to reaction of Components (l)-(lll), and is optionally combined with at least one amine reactivity delayer; or (III)(d) at least one said amine is first reacted with all of Component (II) wherein the reaction product is a combination of Components (II) and (III) and no additional amounts of Component (II) or Component (II!) are reacted with said composition; or combinations of reaction products as described in (li!)(d); and optionally, IV. Component (IV) comprising at least one reactivity delayer which is combined with Component (II), or Component (III), or a combination thereof.