Phosphorus-Tocopherol Oligomers for Low-Migration Polymer Stabilization

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing oligomeric and polymeric antioxidants are not based on renewable raw materials and do not include a 6-hydroxychroman core, posing challenges in stabilizing organic materials, particularly at elevated temperatures, with issues of migration and volatility.

Innovation Solution

Development of oligomers and polymers comprising a phosphorus-containing structural element with a 6-hydroxychroman core, derived from renewable resources, which are used in compositions to stabilize organic materials, including plastics and rubbers, by incorporating specific repeating units and ratios.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional oligomeric and polymeric antioxidants are used, then stabilization effectiveness is achieved, but migration and volatility increase particularly at elevated temperatures

Engineering Contradiction:
Improvestabilization effectivenessVSAvoidmigration and volatility
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent changes the molecular weight parameter of the antioxidant by polymerizing tocopherol units to form oligomers with 2-50 repeating units. This parameter change reduces volatility and migration while maintaining antioxidant effectiveness, as the higher molecular weight prevents sublimation and enhances thermal stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite antioxidant structure by combining tocopherol units with phosphorus-containing stabilizer units in an oligomeric framework. This composite structure integrates the antioxidant properties of tocopherol with the stabilizing properties of phosphorus compounds, achieving both protection against oxidation and reduced migration/volatility.

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If renewable raw materials are used for antioxidants, then environmental sustainability is improved, but availability of suitable compounds with low migration and volatility is limited

Engineering Contradiction:
Improverenewable raw material usageVSAvoidmigration and volatility
Core Design Contradiction:
Adaptability or versatilityVSLoss of substance

Solution Approach 1:

The patent modifies the molecular weight parameter of renewable tocopherol by polymerizing it into oligomers with 2-50 repeating units. This transformation maintains the renewable origin of the material while fundamentally improving its physical properties to reduce migration and volatility, overcoming the limitations of low molecular weight natural antioxidants.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses phosphorus-containing stabilizer units as intermediary components that link tocopherol units together in the oligomeric structure. This intermediary approach allows the combination of renewable tocopherol with synthetic phosphorus compounds to create a hybrid oligomer that achieves both sustainability and reduced migration/volatility.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Loss of substance

If molecular weight of antioxidants is increased to reduce migration and volatility, then stabilization at elevated temperatures is improved, but synthesis complexity increases

Engineering Contradiction:
Improvemigration and volatilityVSAvoidsynthesis complexity
Core Design Contradiction:
Loss of substanceVSDevice complexity

Solution Approach 1:

The patent systematically varies the number of tocopherol repeating units (n=2-50) to achieve the desired molecular weight and performance characteristics. This controlled parameter change allows optimization of the balance between reduced migration/volatility and manageable synthesis complexity, with higher n values providing better performance but requiring more complex synthesis.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs phosphorus-containing stabilizer units as intermediary building blocks that facilitate the polymerization of tocopherol units. These intermediary units provide reactive sites for chain extension and crosslinking, enabling the synthesis of high molecular weight oligomers through controlled polymerization reactions rather than direct coupling of tocopherol molecules.

Inventive Principle:
Principle #24Intermediary (Mediator)

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 developed oligomers and polymers effectively stabilize organic materials, reducing migration and volatility while maintaining effectiveness, particularly in high-temperature applications, using renewable raw materials.

Implementation Method 1

antioxidants, which interfere with the free radicals formed during autoxidation and thus interrupt the degradation process

Methodology Applied
Scientific EffectFree radical interference:

Implementation Method 2

secondary antioxidants, which react with intermediately formed hydroperoxides

Methodology Applied
Scientific EffectHydroperoxide reaction:

Data Source

PatentUS12545765B2Oligomer or polymer, composition, use of the oligomer or polymer and intermediate
Publication Date: 2026.02.10 FRAUNHOFER GESELLSCHAFT ZUR FORDERUNG DER ANGEWANDTEN FORSCHUNG EV
  • US12545765B2 patent drawing
  • US12545765B2 patent drawing
  • US12545765B2 patent drawing

AI summary

This object is achieved by an oligomer or polymer, comprising a phosphorus-comprising structural element described herein, its composition comprising the aforementioned oligomer or polymer and an organic component to be stabilized, and by the possible uses of the oligomers or polymers according to the invention, relating to a molding compound or a molded part, and relating to an intermediate suitable for synthesizing the oligomers or polymers according to the invention. Advantageous developments thereof are also described.