Cyclic Siloxane Compounds with Fluorinated Alkyl Groups

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Solution Overview

Problem

Cyclic siloxane compounds with both aliphatic unsaturation-containing organic groups and fluorinated alkyl groups within the molecular structure are not previously known, limiting the ability to further improve polymer performances and provide novel properties in silicone fluids and rubbers.

Innovation Solution

A novel cyclic siloxane compound is synthesized by reacting a dichlorosilane with a fluorinated cyclic siloxane in the presence of a catalyst, followed by hydrolysis to form a silane compound with chloro groups at both ends, which then undergoes ring-closure to produce the target cyclic siloxane compound with improved properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If cyclic siloxane compounds with both aliphatic unsaturation-containing organic groups and fluorinated alkyl groups are synthesized, then polymer performance and novel physical properties are improved, but the synthesis complexity and difficulty increase

Engineering Contradiction:
Improvepolymer performanceVSAvoidsynthesis complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The synthesis is divided into two distinct stages: first forming a silane compound with chloro groups at both ends through condensation reaction, then performing ring-closure to form the cyclic siloxane structure. This segmentation simplifies the overall synthesis by breaking down a complex one-step process into manageable sequential steps, each with controlled conditions and intermediates that can be isolated and characterized.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The silane compound with chloro groups at both ends serves as a key intermediate structure that bridges the starting materials (dichlorosilane and fluorinated cyclic siloxane) and the final cyclic siloxane product. This intermediate allows for controlled transformation and ensures proper molecular structure formation during the ring-closure step.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If a multi-step synthesis method is used to create the cyclic siloxane compound, then the desired molecular structure with both functional groups is achieved, but the manufacturing process becomes more complex and time-consuming

Engineering Contradiction:
Improvemolecular structure precisionVSAvoidmanufacturing ease
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The first synthesis step preliminarily forms the silane compound with chloro terminal groups, establishing the correct molecular framework and functional groups before the ring-closure reaction. This preliminary action ensures that when the second step occurs, the molecular structure is already properly configured for cyclization, reducing side reactions and improving yield.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The synthesis utilizes parameter changes including temperature control, catalyst selection, and solvent conditions to optimize each reaction step. By adjusting these parameters appropriately for each stage, the method achieves high molecular structure precision while maintaining reasonable manufacturing ease through controlled and predictable reaction conditions.

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If novel cyclic siloxane compounds are developed, then new physical properties and polymer performances are achieved, but the availability of raw materials and synthesis accessibility decrease

Engineering Contradiction:
Improvephysical propertiesVSAvoidsynthesis accessibility
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The method employs parameter changes such as varying the aliphatic unsaturation-containing organic group (X) and the fluorinated alkyl group (R) to achieve different physical properties and polymer performances. By systematically changing these parameters while maintaining the core synthesis methodology, novel compounds with desired properties can be developed using commercially available starting materials, preserving synthesis accessibility.

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 resulting cyclic siloxane compounds serve as effective modifiers for silicone fluids and rubbers, enhancing performance and providing novel physical properties when used as polymerizable monomers, with high yields and purity achieved through a simple method using commercially available materials.

Implementation Method 1

reacting a dichlorosilane with a fluorinated cyclic siloxane in the presence of a catalyst, followed by hydrolysis to form a silane compound with chloro groups at both ends

Methodology Applied
Scientific EffectCondensation reaction:

Implementation Method 2

followed by hydrolysis to form a silane compound with chloro groups at both ends, which then undergoes ring-closure to produce the target cyclic siloxane compound

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS7189868B2Cyclic siloxane compounds and making method
Publication Date: 2007.03.13 SHIN ETSU CHEMICAL CO LTD
  • US7189868B2 patent drawing
  • US7189868B2 patent drawing
  • US7189868B2 patent drawing

AI summary

Novel cyclic siloxane compounds have both an aliphatic unsaturation-containing organic group and fluorinated alkyl groups within the molecular structure. When used to form silicone fluids and rubbers, they are useful as a modifier for giving novel physical properties thereto and when used as polymerizable monomers, they are effective for improving the performance of polymers or forming polymers with novel physical properties.