Symmetric Hyperbranched Silicone Polymer Purity

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Solution Overview

Problem

Conventional siloxane-based polymerizable compounds with branched structures suffer from chemical brittleness, poor flexibility, and issues with internal rearrangement during hydrosilylation reactions, leading to impurities and unpleasant odors, which hinder their commercialization and application in pharmaceuticals, medical devices, and foods.

Innovation Solution

A symmetric hyperbranched silicone-modified polymerizable compound with a glycerin structure and a specific ether group is developed, incorporating a divalent hydrocaronylene methylene ether group and a platinum catalyst in a modularized manufacturing method to enhance flexibility and reduce internal rearrangement products.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If a siloxane chain is introduced into an allyl ether compound by hydrosilylation, then a branched type siloxane can be synthesized, but 10 to 20% of the olefins are internally rearranged to form a 1-propenyl ether product, leading to impurities and unpleasant odors

Engineering Contradiction:
Improvesynthesis of branched type siloxaneVSAvoidpurity of the product
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent changes the chemical structure parameters of the starting material from conventional allyl ether to a specifically designed polymerizable compound with controlled double bond positioning. This structural parameter change prevents internal rearrangement during hydrosilylation while maintaining the ability to form branched siloxane structures, thereby achieving high purity products without unpleasant odors

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining siloxane chains with specifically designed polymerizable groups containing ether bonds. This composite structure achieves both the desired branched morphology and chemical stability, preventing the formation of impure rearrangement products while maintaining manufacturability

Inventive Principle:
Principle #40Composite materials

2Device complexity

If the branch size increases to achieve higher generation dendrimer structure, then the branched structure becomes more complex, but steric hindrance effects appear and reactivity of the polymerizable functional group becomes insufficient

Engineering Contradiction:
Improvebranched structure complexityVSAvoidreactivity of polymerizable functional group
Core Design Contradiction:
Device complexityVSReliability

Solution Approach 1:

The patent segments the molecular structure into distinct functional regions: flexible ether bond-containing linkers that provide spatial separation, and polymerizable groups positioned at optimal distances from the branched core. This segmentation reduces steric hindrance between branches while maintaining the complex dendrimer architecture, ensuring sufficient reactivity even at higher generations

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention incorporates flexible ether bond-containing linkers that act as flexible spacers between the rigid siloxane core and the polymerizable functional groups. These flexible segments allow the molecule to adopt configurations that minimize steric hindrance while maintaining branch complexity, preserving functional group reactivity in higher generation structures

Inventive Principle:
Principle #30Flexible shells and thin films

3Ease of manufacture

If conventional linear siloxane is used, then the structure is simple to manufacture, but the material lacks flexibility and chemical structural robustness compared to branched structures

Engineering Contradiction:
Improvestructural simplicityVSAvoidflexibility and chemical robustness
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent creates a composite structure that combines the simplicity of linear siloxane synthesis with the advantages of branched architecture by using hydrosilylation to introduce branches onto a linear backbone. This approach maintains ease of manufacture while achieving the flexibility and chemical robustness characteristic of branched structures

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention introduces dynamic flexibility through ether bonds in the linker regions of the branched structure. These ether bonds provide rotational freedom and conformational flexibility that linear siloxanes lack, enhancing the material's ability to adapt to different environments while maintaining structural integrity

Inventive Principle:
Principle #15Dynamics

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 solution provides a chemically flexible, sterically pure, and positionally symmetric polymerizable compound with improved reactivity, minimizing internal rearrangement and odor issues, enabling its use in diverse applications while maintaining high purity.

Implementation Method 1

it has been developed a method in which a siloxane chain is tried to introduce into an allyl ether compound (CH 2 =CHCH 2 OR) by hydrosilylation

Methodology Applied
Scientific EffectHydrosilylation:

Implementation Method 2

incorporating a divalent hydrocaronylene methylene ether group and a platinum catalyst in a modularized manufacturing method

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2778169B1Symmetric hyperbranched silicone-modified polymerizable compound and modularized manufacturing method thereof
Publication Date: 2016.12.07 SHIN ETSU CHEMICAL CO LTD

AI summary

The invention provides a symmetric hyperbranched silicone-modified polymerizable compound comprises a compound represented by the general formula (1). There can be provided a symmetric hyperbranched silicone-modified polymerizable compound having a structure with chemically high flexibility at the branched chain, having good reactivity of the polymerizable functional group, and having a branched structure which is positionally and sterically symmetric and pure than the conventional ones.          (RARB)2CHORCcRD     (1) wherein RA represents a monovalent linear, branched or cyclic siloxane chain; RB represents -CH2CRb1Rb2(CRb3Rb4)n1OCH2-; RC represents a divalent linking group; "c" represents 0 or 1; and RD represents an unsaturated polymerizable functional group.