Amidine Catalyst for Silane Crosslinking

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Solution Overview

Problem

Curable compositions containing silane groups face challenges with catalysts that are toxic, volatile, and prone to migration, leading to slow crosslinking and stability issues, particularly with organotin compounds and certain amidine and guanidine catalysts.

Innovation Solution

A catalyst with aliphatic amidine or guanidine groups is developed, which has high catalytic activity, low viscosity, and excellent compatibility, allowing for rapid curing without affecting storage stability and minimizing odor and toxicity, and is suitable for use without solvents due to its liquid state at room temperature.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If organotin compounds are used as catalysts, then crosslinking activity is high, but toxicity and environmental hazard increase

Engineering Contradiction:
Improvecrosslinking activityVSAvoidtoxicity
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the catalyst by replacing organotin compounds with organotitanate, zirconate, or aluminate compounds. These alternative catalysts have different chemical properties that reduce toxicity while maintaining crosslinking activity. The patent specifically uses metal alkoxides or metal carboxylates with controlled molecular weights and functional groups to achieve both low toxicity and high catalytic performance in silane crosslinking reactions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs catalysts that are less persistent and less toxic than organotin compounds. The organotitanate, zirconate, and aluminate catalysts described are designed to be more environmentally benign and less hazardous, effectively replacing the harmful organotin compounds with safer alternatives that still provide the necessary crosslinking function.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Object-affected harmful factors

If alternative metal catalysts (organotitanates, zirconates, aluminates) are used, then toxicity is reduced, but crosslinking speed decreases

Engineering Contradiction:
ImprovetoxicityVSAvoidcrosslinking speed
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent optimizes the molecular weight, functional groups, and structural parameters of the alternative metal catalysts to enhance their crosslinking activity. By carefully selecting metal alkoxides or carboxylates with specific properties, the patent achieves high crosslinking speeds comparable to organotin compounds while maintaining the lower toxicity of the alternative metals. The patent controls parameters such as metal-to-alkoxide ratio, molecular weight of the organic ligand, and presence of co-catalysts to maximize reaction rate.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent may use composite catalyst systems combining alternative metal compounds with organic co-catalysts or promoters to achieve synergistic effects. This composite approach allows the alternative metal catalyst to provide low toxicity while the organic components enhance the crosslinking speed, effectively resolving the contradiction between safety and performance.

Inventive Principle:
Principle #40Composite materials

3Stability of the object's composition

If alternative metal catalysts are used, then storage stability is improved, but catalytic activity decreases due to hydrolysis

Engineering Contradiction:
Improvestorage stabilityVSAvoidcatalytic activity
Core Design Contradiction:
Stability of the object's compositionVSProductivity

Solution Approach 1:

The patent carefully controls the hydrolysis resistance parameters of the alternative metal catalysts by selecting metals and ligands with appropriate properties. The patent uses metal alkoxides or carboxylates with controlled water sensitivity, balancing storage stability against catalytic activity. By adjusting the molecular weight of the organic ligand, the metal-to-alkoxide ratio, and the presence of protective groups, the patent achieves catalysts that remain stable during storage but become highly active under crosslinking conditions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent may incorporate preliminary protective measures such as using water-scavenging agents, controlling moisture content in the composition, or pre-forming stable catalyst complexes that only become active when needed. This allows the catalyst to maintain storage stability while ensuring high catalytic activity is available when the crosslinking reaction commences.

Inventive Principle:
Principle #10Preliminary action

4Productivity

If basic compounds (amines) are combined with metal catalysts, then hydrolysis acceleration is improved, but storage stability decreases

Engineering Contradiction:
Improvehydrolysis accelerationVSAvoidstorage stability
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent optimizes the basicity and concentration of amine co-catalysts to achieve the desired balance between hydrolysis acceleration and storage stability. By carefully controlling the type, amount, and molecular weight of the amine compound used in combination with the alternative metal catalyst, the patent enhances the hydrolysis rate of silane groups during crosslinking while minimizing premature reactions during storage. The patent may use weakly basic amines or control the pH of the system to prevent excessive basicity that would compromise storage stability.

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 catalyst enables rapid and high-quality curing of compositions with silane groups, ensuring mechanical stability and low emission, while maintaining storage stability and preventing migration-related defects such as sticky surfaces or substrate contamination.

Implementation Method 1

Catalysts are often used to accelerate such crosslinking reactions... The catalyst according to claim 1 contains aliphatic amidine or guanidine groups and shows high catalytic activity

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3131670B1Cross-linking catalyst with polyether structural units
Publication Date: 2021.08.25 SIKA TECH AG
  • EP3131670B1 patent drawing
  • EP3131670B1 patent drawing
  • EP3131670B1 patent drawing

AI summary

The present invention concerns a catalyst of formula (I) having amidine- or guanidine groups and containing a polyoxyalkylene group or a group of a polyoxyalkylated compound. At room temperature the catalyst is fluid and odourless. It is particularly suitable as a cross-linking catalyst for curable compositions, in particular for silane group-containing compositions. It is particularly good at accelerating the hardening of such groups, without impairing stability in storage, and displays little volatility but good compatibility, as a result of which such compositions do not tend towards separation or migration or evaporation of the catalyst.