Polymeric Phenolic Antioxidants Preventing Migration

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Solution Overview

Problem

Existing antioxidants used in materials are prone to migration, leading to environmental hazards and oxidative degradation, and they often discolor fabrics during laundering, posing a challenge in balancing performance and side effects.

Innovation Solution

Development of phenol compounds with polymeric substituents, specifically phenyl groups bonded to hydroxy groups and multiple monomer units, which are integrated into polyurethane polymers to prevent migration and discoloration, enhancing antioxidant properties while maintaining compatibility with polymer components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antioxidants are used to stabilize materials against oxidative degradation, then antioxidant performance is improved, but migration occurs leading to environmental hazards and material discoloration

Engineering Contradiction:
Improveantioxidant performanceVSAvoidmigration and discoloration
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies composite materials by combining the antioxidant phenolic core structure with polymeric substituent groups. This creates a hybrid molecule that integrates the stabilizing function with polymeric characteristics that prevent migration. The composite structure allows the antioxidant to function effectively while the polymeric portions provide anchoring to the material matrix, eliminating the harmful migration and discoloration effects of conventional antioxidants.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent changes the molecular parameters of antioxidants by introducing polymeric substituents with varying chain lengths, compositions, and architectures. This parameter modification transforms the physical and chemical properties of the antioxidant, reducing its mobility and tendency to migrate while maintaining its radical-scavenging capability. The parameter changes effectively suppress the harmful effects without compromising antioxidant performance.

Inventive Principle:
Principle #35Parameter changes

2Stability of the object's composition

If antioxidants are added to materials to prevent oxidative degradation, then material stability is improved, but the antioxidants discolor fabrics during laundering

Engineering Contradiction:
Improvematerial stabilityVSAvoiddiscoloration
Core Design Contradiction:
Stability of the object's compositionVSObject-generated harmful factors

Solution Approach 1:

The composite structure of polymeric-substituted phenols combines the stabilizing phenolic core with polymeric chains that modify the molecule's interaction with fabric substrates. This composite design prevents the antioxidant from depositing onto fabric surfaces during laundering, thereby eliminating discoloration while preserving the material stability function.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies local quality by differentiating the functions of different parts of the molecule: the phenolic core provides antioxidant activity and material stabilization, while the polymeric substituents provide migration resistance and prevent fabric deposition. This functional differentiation ensures that stabilization is achieved without the harmful discoloration effect.

Inventive Principle:
Principle #3Local quality

3Object-generated harmful factors

If antioxidant levels are reduced to minimize migration, then environmental hazards are reduced, but material susceptibility to oxidative degradation increases

Engineering Contradiction:
ImprovemigrationVSAvoidoxidative degradation resistance
Core Design Contradiction:
Object-generated harmful factorsVSReliability

Solution Approach 1:

The polymeric-substituted phenolic antioxidants represent a composite material that inherently resists migration due to the polymeric chains' interaction with the material matrix. This structural feature allows the use of effective antioxidant concentrations without excessive migration, maintaining both environmental safety and oxidative degradation resistance.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

By changing the molecular parameters through polymeric substitution, the patent creates antioxidants with reduced mobility parameters. This allows maintaining adequate antioxidant levels for protection while the modified parameters prevent excessive migration, resolving the contradiction between hazard reduction and protection maintenance.

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 phenol compounds effectively scavenge free radicals, preventing oxidative degradation and reducing migration, thus extending material lifespan and maintaining fabric color, while being tailored for optimal performance in polymers and laundry care compositions.

Implementation Method 1

Antioxidants are a class of compounds used to stabilize materials (e.g., polymers) that are susceptible to oxidative degradation. One potential pathway to such oxidative degradation is through the formation of free radicals in the material. These free radicals can form through hydrogen abstraction or homolytic cleavage of carbon-carbon bonds

Methodology Applied
Scientific EffectFree radical scavenging: Hydrogenation

Data Source

PatentUS11987552B2Polymeric phenolic antioxidants
Publication Date: 2024.05.21 MILLIKEN & CO
  • US11987552B2 patent drawing
  • US11987552B2 patent drawing
  • US11987552B2 patent drawing

AI summary

A phenol compound comprises a phenyl group, a hydroxy group directly bonded to the phenyl group, and at least one polymeric substituent bound to the phenyl group. The polymeric substituent comprises three or more monomers units. A method for producing a polyurethane polymer comprises the steps of (a) providing a polyol; (b) providing a polyisocyanate compound; (c) providing the phenol compound described above; (d) combining the polyol, the polyisocyanate compound, and the phenol compound to produce a reaction mixture; and (e) allowing the polyol and the polyisocyanate compound to react to produce a polyurethane polymer.