Resorcinol UV Stabilizer Mixtures for Coating Solubility

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Solution Overview

Problem

Diacyl resorcinol derivatives, commonly used as UV absorbers in coatings, face challenges due to their low solubility in organic polymer matrices, particularly in acrylate-based clear coats, which limits their compatibility and effectiveness.

Innovation Solution

The use of mixtures of resorcinol derivatives, obtained through a one-step synthesis, significantly increases solubility in alcoholic solvents, providing an efficient route for weathering protective coatings by enhancing the compatibility of diacyl resorcinol derivatives with the coating matrix.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If diacyl resorcinol derivatives are used as UV absorbers in coatings, then UV protection is improved, but solubility in organic polymer matrices deteriorates

Engineering Contradiction:
ImproveUV protectionVSAvoidsolubility in organic polymer matrices
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent changes the chemical structure parameters of diacyl resorcinol derivatives by introducing alkyl side chains at specific positions (R1-R6) to modify solubility characteristics while preserving UV absorption functionality. This allows the UV absorber to be compatible with organic polymer matrices without sacrificing UV protection.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite UV absorber molecules combining the core diacyl resorcinol structure with alkyl side chain groups. This composite approach integrates the UV-absorbing aromatic core with hydrophobic alkyl groups that enhance solubility in organic polymer matrices, resolving the contradiction between UV protection and solubility.

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If silane side groups are introduced to increase solubility, then compatibility with coating matrix is improved, but synthesis complexity and cost increase

Engineering Contradiction:
Improvecompatibility with coating matrixVSAvoidsynthesis complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent extracts the solubility-enhancing function from complex silane side groups and implements it through simpler alkyl side chains. This extraction of the essential function (increasing solubility) while removing unnecessary complexity (silane chemistry, multiple synthesis steps) reduces both synthesis complexity and cost while maintaining compatibility with coating matrices.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces expensive, complex silane side groups with simpler, more economical alkyl side chains that achieve the same solubility enhancement without requiring multi-step synthesis. This substitution uses cheaper, easier-to-produce structural elements to achieve the desired technical effect.

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

3Adaptability or versatility

If trialkoxysilane side chains are used to improve solubility, then compatibility is improved, but mechanical properties of coating matrix deteriorate

Engineering Contradiction:
Improvecompatibility with coating matrixVSAvoidabrasion resistance
Core Design Contradiction:
Adaptability or versatilityVSStrength

Solution Approach 1:

The patent applies local quality modification by introducing alkyl side chains at specific positions (R1-R6) on the resorcinol core rather than using bulky trialkoxysilane groups. This localized structural modification enhances solubility and compatibility while avoiding the steric bulk that would compromise the mechanical properties and abrasion resistance of the coating matrix.

Inventive Principle:
Principle #3Local quality

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

This approach addresses the inefficiencies of conventional solutions by improving solubility and compatibility, reducing synthesis costs, and maintaining the mechanical properties of the coating, thereby enhancing the weathering resistance of coated materials.

Implementation Method 1

Diacyl resorcinol derivatives used as UV absorbers in coatings for exterior use

Methodology Applied
Scientific EffectUV absorption: Absorption (EM radiation)

Implementation Method 2

a photopolymerizable composition for the formation of a cured coating layer

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentEP4031613B1Curable composition comprising UV stabilizer
Publication Date: 2025.05.21 MOMENTIVE PERFORMANCE MATERIALS INC
  • EP4031613B1 patent drawing
  • EP4031613B1 patent drawing
  • EP4031613B1 patent drawing

AI summary

The present invention relates to curable compositions comprising at least one compound of the formula (1), wherein R is C1-C10 alkyl, and R1-R10 each are independently selected from the group consisting of hydrogen and C1-C10 alkyl, with the proviso that at least one of R1-R10 is alkyl, and wherein the substitution patterns formed by the residues R1-R5 and R6-R10 on each of the aromatic rings are different from each other, cured compositions obtained from such curable compositions, mixtures of compounds of the formula (1), the use of such compounds and mixtures of such compounds as a UV stabilizer in curable compositions, and a process for the manufacture of curable compositions comprising a UV stabilizer of the formula (1).