Bicyclic Amine Catalyst for Scratch-Resistant Automotive Coatings

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Solution Overview

Problem

Current coating agents for automotive clear coats lack sufficient scratch resistance and weather stability, particularly against UV radiation in the wet-dry cycle, and often exhibit post-crosslinking issues that lead to stress cracks, while also requiring complex formulations and toxic catalysts.

Innovation Solution

The use of bicyclic amines, specifically 1,5-diazabicyclo[4.3.0]non-5-ene or 1,8-diazabicyclo[5.4.0]undec-7-en, as catalysts in combination with phosphorus-containing catalysts to facilitate complete crosslinking reactions of silane and isocyanate groups, enhancing scratch resistance and weather stability without post-crosslinking.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If conventional catalysts (tertiary amines or metal catalysts) are used for isocyanate crosslinking, then crosslinking speed is improved, but silane condensation is inhibited and post-crosslinking occurs causing stress cracks

Engineering Contradiction:
Improvecrosslinking speedVSAvoidweather stability
Core Design Contradiction:
SpeedVSReliability

Solution Approach 1:

The patent divides the catalysis function into two separate specialized catalysts: a phosphorus-containing catalyst specifically for silane condensation and a bicyclic amine catalyst specifically for isocyanate crosslinking. This segmentation allows each catalyst to optimize its respective reaction without interfering with the other, eliminating post-crosslinking issues and stress cracks while maintaining fast initial curing speed.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent introduces a bicyclic amine as an intermediary catalyst that mediates the isocyanate crosslinking reaction without catalyzing silane condensation. This intermediary catalyst enables precise control over reaction selectivity, allowing isocyanate groups to react completely during the curing process without triggering unwanted silane post-crosslinking that would cause stress cracks.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Strength

If high crosslinking density is achieved for scratch resistance, then mechanical strength is improved, but weather stability against UV radiation deteriorates due to stress cracks

Engineering Contradiction:
Improvescratch resistanceVSAvoidweather stability
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent segments the crosslinking process into two distinct reaction pathways catalyzed by different catalysts: silane condensation forming inorganic crosslinks and isocyanate crosslinking forming organic crosslinks. This segmentation ensures complete conversion of isocyanate groups during curing, creating a dense crosslinked network for scratch resistance without leaving unreacted groups that would cause post-crosslinking stress cracks under UV exposure.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent changes the catalytic parameters by selecting a bicyclic amine with specific structural characteristics that provide high catalytic activity for isocyanate crosslinking but low activity for silane condensation. This parameter change in catalyst selection enables achieving high crosslinking density for scratch resistance while preventing the conditions that lead to stress cracks during weathering.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If complete conversion of isocyanate groups is achieved, then chemical stability is improved, but post-crosslinking occurs leading to stress cracks under UV radiation

Engineering Contradiction:
Improvechemical stabilityVSAvoidresistance to stress cracks
Core Design Contradiction:
Stability of the object's compositionVSReliability

Solution Approach 1:

The patent segments the catalytic functions to ensure that isocyanate crosslinking is catalyzed exclusively by the bicyclic amine without phosphorus catalyst interference. This segmentation allows complete conversion of isocyanate groups for chemical stability while the phosphorus catalyst independently manages silane condensation, preventing the interaction that would cause post-crosslinking stress cracks.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The bicyclic amine acts as a selective intermediary catalyst that promotes isocyanate crosslinking to completion while being inactive toward silane condensation. This intermediary role ensures that all isocyanate groups are converted to stable urea linkages without triggering subsequent silane post-crosslinking reactions that would generate stress cracks during UV exposure and wet-dry cycling.

Inventive Principle:
Principle #24Intermediary (Mediator)

4Productivity

If toxic catalysts (tin-containing) are used for complete crosslinking, then conversion efficiency is improved, but environmental compatibility deteriorates

Engineering Contradiction:
Improvecrosslinking conversion efficiencyVSAvoidtoxicity
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces toxic tin catalysts with environmentally benign phosphorus-containing catalysts and bicyclic amine catalysts. Although these alternative catalysts may have different handling characteristics, they eliminate the toxicological and ecological problems associated with tin compounds while maintaining effective crosslinking conversion efficiency for both silane and isocyanate reactions.

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

Solution Approach 2:

The patent changes the chemical parameters of the catalyst system by selecting phosphorus-containing compounds and bicyclic amines as catalysts. These parameter changes in catalyst chemistry provide comparable or superior catalytic activity for crosslinking reactions while fundamentally improving environmental compatibility and eliminating the harmful effects of tin-containing catalysts.

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 coating agents achieve high scratch resistance and chemical stability immediately after curing, with excellent resistance to UV radiation and wet-dry cycles, allowing for thicker layer applications without stress cracks, and are produced with simpler, more reproducible processes without ecological or toxicological issues.

Implementation Method 1

at least one phosphorus-containing catalyst (C) for the crosslinking of silane groups

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

one or more components of the coating agent contain hydrolyzable silane groups

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Implementation Method 3

at least one another catalyst (D) wherein one or more components of the coating agent contain hydroxyl groups, (b) at least one compound (B) with free and/or blocked isocyanate groups

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2225300B1Coating composition having a high scratch resistance and weathering stability
Publication Date: 2016.07.06 BASF COATINGS GMBH
  • EP2225300B1 patent drawing
  • EP2225300B1 patent drawing
  • EP2225300B1 patent drawing

AI summary

The present invention relates to a coating composition containing (a) at least one hydroxyl-containing compound (A), (b) at least one compound (B) having free and/or blocked isocynate groups and (c) at least one phosphate-containing catalyst (C) for the crosslinking of silane groups, (d) at least one further catalyst (D), where one or more constituents of the coating composition contain hydrolyzable silane groups, characterized in that the catalyst (D) is a bicyclic amine.