Oxazolidine Curing Agent for Odorless Polyurethane

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Solution Overview

Problem

Existing latent curing agents for curable polyurethane compositions, such as oxazolidine-based agents, face issues like premature crosslinking, volatile odor emissions, limited storability, and blistering due to carbon dioxide release, which restrict their use in industrial applications.

Innovation Solution

Development of a compound with an oxazolidino group having a six-membered ring structure or sulfur/tertiary amine instead of oxygen, which remains liquid at typical use temperatures, has low viscosity, and upon hydrolysis, releases a nonvolatile, odorless blocking agent, ensuring stable storage and curing without blistering.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If oxazolidine curing agents are used to prevent carbon dioxide blistering, then curing quality improves, but storage stability deteriorates due to premature crosslinking

Engineering Contradiction:
Improvecuring qualityVSAvoidstorage stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent modifies the molecular structure of oxazolidine curing agents by introducing specific substituents (combinations of R1-R6 groups including alkyl, alkoxy, aryl, and heteroatoms) to adjust reactivity parameters. This allows the curing agent to remain stable during storage while maintaining effective crosslinking capability when activated, thus resolving the contradiction between storage stability and curing quality.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If traditional latent curing agents are used to achieve rapid crosslinking, then curing speed improves, but open time decreases too much

Engineering Contradiction:
Improvecuring speedVSAvoidopen time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent creates a dynamic curing system where the oxazolidine ring structure remains stable during storage but undergoes controlled hydrolysis when exposed to moisture, dynamically adjusting the release rate of the active amine. This dynamic behavior allows rapid crosslinking when needed while maintaining adequate open time for application and repositioning.

Inventive Principle:
Principle #15Dynamics

3Strength

If oxazolidine curing agents are used to increase crosslinking density, then mechanical strength improves, but odor emissions increase due to blocking agent release

Engineering Contradiction:
Improvemechanical strengthVSAvoidodor emissions
Core Design Contradiction:
StrengthVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the blocking agent by selecting specific aldehydes with higher molecular weights and lower volatility (such as those with C10-C20 alkyl chains). These modified blocking agents release fewer odorous compounds during curing while still effectively protecting the amino groups, thus achieving high crosslinking density without excessive odor emissions.

Inventive Principle:
Principle #35Parameter changes

4Ease of manufacture

If solid oxazolidine curing agents are used to achieve low cost, then material cost decreases, but handling complexity increases due to melting or dissolution requirements

Engineering Contradiction:
Improvematerial costVSAvoidhandling complexity
Core Design Contradiction:
Ease of manufactureVSEase of operation

Solution Approach 1:

The patent exploits phase transition principles by designing oxazolidine compounds that remain in the liquid phase at room temperature through careful selection of substituent groups. This eliminates the need for melting or dissolution steps, simplifying handling and application while maintaining cost-effectiveness compared to solid alternatives.

Inventive Principle:
Principle #36Phase transitions

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 new oxazolidine curing agents provide stable, high-quality polyurethane polymers with improved mechanical strength, extensibility, and heat stability, suitable for indoor and large-area applications without odor emissions or substrate damage, and exhibit excellent compatibility with the cured polymer.

Implementation Method 1

which release amino groups on contact with moisture and are crosslinked rapidly with the isocyanate groups

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS11535694B2Latent curing agent and curable polyurethane composition
Publication Date: 2022.12.27 SIKA TECH AG
  • US11535694B2 patent drawing
  • US11535694B2 patent drawing
  • US11535694B2 patent drawing

AI summary

A compound of formula (I) having advantageous properties when used as a latent curing agent for compositions containing isocyanate groups, and to compositions containing the compound of formula (I). The compound of formula (I) is odourless, is liquid and has comparatively low viscosity at room temperature and is stable in storage together with isocyanates. It makes possible odourless single-component polyurethane compositions which have good stability in storage, do not produce bubbles when cured in the presence of moisture, and cause no problematic odour emissions, giving a cured elastic material having good mechanical properties, good heat stability, a surprisingly non-adhesive surface and little tendency towards plasticizer migration.