Thiosulfonate Triazinane Crosslinkers for Rubber Aging and Fatigue

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Solution Overview

Problem

Existing vulcanized rubber compositions lack desirable aging properties and dynamic properties when using lower sulfur and higher accelerator ratios, and separate addition of cross-linking agents and accelerators limits compounding freedom.

Innovation Solution

Development of triazinanes with three neutral thiosulfonate end-groups that form flexible crosslinks during vulcanization, synthesized through reactions involving sulfide salts, alkylarenesulfonyl halides, haloalkylamine hydrohalides, and aldehydes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If lower proportions of sulfur and increased proportions of accelerator are used relative to conventional cure, then aging properties are improved, but dynamic properties become inferior

Engineering Contradiction:

Improveaging propertiesVSAvoiddynamic properties

Core Design Contradiction:

ReliabilityVSStrength

Solution Approach 1:

The patent combines the accelerator and cross-linking agent into a single triazinane molecule that contains both accelerator and cross-linking functionalities. This merging allows the compound to simultaneously improve aging properties through accelerator activity while maintaining dynamic properties through cross-linking activity, resolving the trade-off between these two properties.

Inventive Principle:

Principle #5Merging (Combining)

Solution Approach 2:

The triazinane compounds serve multiple functions: they act as accelerators to speed up vulcanization, as cross-linking agents to form sulfur bridges, and as aging inhibitors. This multi-functionality allows a single compound to address multiple requirements simultaneously, including improving aging properties without sacrificing dynamic properties.

Inventive Principle:

Principle #6Universality (Multi-functionality)

2Reliability

If bis(sulfenamides) and compounds containing two or more accelerator groupings are used, then aging properties are improved, but freedom for variations in compounding is lost

Engineering Contradiction:

Improveaging propertiesVSAvoidfreedom for variations in compounding

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The triazinane compounds are designed with a specific segmented structure where the triazinane core provides accelerator functionality and attached sulfur-containing groups provide cross-linking functionality. This segmentation of functions within a controlled molecular architecture allows for systematic variation of compounding parameters while maintaining both accelerator and cross-linking activities.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The patent employs parameter changes by varying the substituents on the triazinane core (different R groups, different numbers of sulfur atoms) to create a series of compounds with different accelerator and cross-linking strengths. This allows for fine-tuning of compounding formulations to achieve desired balances between processing speed, cross-linking density, and aging resistance.

Inventive Principle:

Principle #35Parameter changes

3Adaptability or versatility

If separate entities of cross-linking agent and accelerator are used, then compounding freedom is maintained, but molecular species having both accelerator and cross-linking activity are not available

Engineering Contradiction:

Improvecompounding freedomVSAvoidaccelerator and cross-linking activity

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The patent merges the accelerator and cross-linking agent into a single triazinane molecule that contains both accelerator and cross-linking functionalities. This merging allows the compound to simultaneously improve aging properties through accelerator activity while maintaining dynamic properties through cross-linking activity, resolving the trade-off between these two properties.

Inventive Principle:

Principle #5Merging (Combining)

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 triazinanes increase the cross-linked network density, improving reversion properties and providing enhanced adhesion, antidegradant, and antifatigue performance in rubber compositions.

Implementation Method 1

Tridentate molecules possessing 3 rubber reactive end-groups can potentially crosslink with 3 rubber chains upon vulcanization

Methodology Applied

Scientific EffectCrosslinking: Chemical Bonding

Implementation Method 2

These crosslinks provide increased retention of physical and dynamic properties when exposed to anaerobic conditions at elevated temperatures

Methodology Applied

Scientific EffectHybrid crosslinking: Chemical Bonding

Data Source

PatentUS12516028B2Triazinanes possessing thiosulfonate end-groups and methods of making them

Publication Date: 2026.01.06 FLEXSYS IP HOLDINGS LLC

AI summary

The present invention is directed to compounds represented by the formula (I): wherein R1 comprises a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, wherein R2 comprises an alkylene group, an arylene group, or a heterocyclic group. The three R2 groups may be the same or different, wherein A comprises an alkyl, an aryl, or an alkylaryl group. The three A groups may be the same or different.