Thioether Synthesis for Aerospace Sealants

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Solution Overview

Problem

The high cost of manufacturing polythioethers for aerospace sealant applications due to expensive raw materials, particularly certain polythiols, necessitates the development of thioethers with similar fuel-resistant and elevated-temperature resistance properties but without the use of polythiols.

Innovation Solution

The development of thioethers comprising specific structures formed from alpha, omega dihalo organic compounds, metal hydrosulfides, and metal hydroxides, which are capable of being produced without polythiols, and can be used in curable compositions such as coating and sealant applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If polythiols are used as raw materials to manufacture polythioethers, then fuel resistance and elevated-temperature resistance are achieved, but manufacturing cost increases significantly

Engineering Contradiction:
Improvefuel resistanceVSAvoidmanufacturing cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent extracts and eliminates the polythiol component from the synthesis pathway. Instead of using polythiols as starting materials, the invention employs a stepwise synthesis method that builds the polythioether structure from smaller, cheaper molecular building blocks (haloalkanes and thiols), thereby removing the source of high manufacturing costs while preserving the desired fuel resistance properties.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent replaces expensive polythiol raw materials with inexpensive small-molecule precursors (haloalkanes and simple thiols). These cheap, readily available starting materials are used in a multi-step synthesis to produce the same functional polythioether product, achieving cost reduction without sacrificing the reliability and fuel resistance of the final sealant composition.

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

2Reliability

If polythiols are used as raw materials to manufacture polythioethers, then fuel resistance and elevated-temperature resistance are achieved, but manufacturing complexity increases

Engineering Contradiction:
Improveelevated-temperature resistanceVSAvoidmanufacturing process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent segments the synthesis process into distinct, manageable steps. Rather than relying on complex polythiol chemistry, the invention divides the synthesis into sequential reactions: first forming a halogenated intermediate, then reacting it with thiol groups to build the polythioether chain incrementally. This segmentation simplifies the overall manufacturing process by breaking down complex transformations into simpler, more controllable steps.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent introduces intermediate compounds as mediators in the synthesis pathway. The halogenated intermediate serves as a bridge between simple starting materials and the final polythioether product. This intermediary approach allows for better control over the polymerization process, simplifies reaction conditions, and avoids the complexity of direct polythiol-based synthesis while maintaining elevated-temperature resistance.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If conventional polythioethers are used, then fuel resistance is achieved, but low temperature flexibility deteriorates

Engineering Contradiction:
Improvefuel resistanceVSAvoidlow temperature flexibility
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent applies local quality by carefully controlling the molecular structure at specific locations within the polymer chain. By adjusting the ratio and type of haloalkane and thiol monomers, and by controlling the degree of polymerization (n value), the invention creates local structural variations that maintain fuel resistance in the bulk material while introducing flexibility at molecular levels. This allows different regions of the polymer to exhibit different properties, achieving both fuel resistance and low-temperature flexibility simultaneously.

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

These thioethers exhibit excellent fuel resistance and elevated-temperature resistance while reducing production costs, offering improved low-temperature flexibility and rapid curing properties, making them suitable for aerospace applications.

Implementation Method 1

thioethers that are the reaction product of reactants comprising: (a) an alpha, omega dihalo organic compound, (b) a metal hydrosulfide, and (c) a metal hydroxide

Methodology Applied
Scientific EffectNucleophilic substitution: Chemical Bonding

Data Source

PatentUS8466220B2Thioethers, methods for their preparation, and compositions including such thioethers
Publication Date: 2013.06.18 PRC DESOTO INTERNATIONAL INC
  • US8466220B2 patent drawing
  • US8466220B2 patent drawing
  • US8466220B2 patent drawing

AI summary

Disclosed are thioethers, methods for preparing such thioethers, and curable compositions, such as coating and sealant compositions, that include such thioethers. The thioethers can be the reaction product of (a) an alpha, omega dihalo organic compound, (b) a metal hydrosulfide and (c) a metal hydroxide.