Guanidine-Functionalized Polymers with Adjustable Side Chain Density

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Solution Overview

Problem

Current methods lack a process to produce polymers with a controllable number of guanidine groups beyond α,ω-guanidine-functionalized polyethers, limiting the versatility of guanidine-group-containing compounds in various applications.

Innovation Solution

A process involving the reaction of a hydroxy-functional starter with epichlorohydrin and alkylene oxides using a double metal cyanide catalyst, followed by reaction with guanidine compounds, to produce guanidine-group-containing polymers with adjustable guanidine functionality.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If α,ω-guanidine-functionalized polyethers are synthesized using conventional methods, then guanidine groups are introduced at terminal positions only, but the number of guanidine groups per polymer chain is limited to two and cannot be adjusted

Engineering Contradiction:
Improveadjustability of guanidine group numberVSAvoidprocess complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent changes the key parameter of guanidine group number from fixed (2 groups) to adjustable (1 to many groups) by modifying the polymer structure to include internal guanidine groups at可控 positions along the chain, enabled by the new synthesis method using dihaloalkane bridges

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces dihaloalkane compounds as intermediary bridging structures between polymer chains and guanidine groups. These intermediaries allow controlled attachment of multiple guanidine groups at internal positions rather than only at terminal positions, enabling adjustable functionality

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If conventional synthesis methods are used for guanidine-functionalized polymers, then the process is simple and well-established, but the polymer can only achieve twofold guanidine functionality with no control over the number of inserted guanidine groups

Engineering Contradiction:
Improvecontrol over guanidine group insertion numberVSAvoidprocess simplicity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The invention changes the manufacturing parameter from fixed terminal functionality to adjustable internal functionality by modifying the reaction conditions, catalyst system, and intermediate structures to enable controlled insertion of varying numbers of guanidine groups

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent segments the polymer structure into distinct functional regions: hydrophobic segments, hydrophilic segments, and internally positioned guanidine groups separated by dihaloalkane bridges. This segmentation allows independent control of each functional element's position and number

Inventive Principle:
Principle #1Segmentation

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

This process enables the production of polymers with a controlled number of guanidine groups, enhancing their applications in cosmetics, as cationic emulsifiers, and providing improved properties such as moisturizing effects and improved combability and softness for hair.

Implementation Method 1

A process involving the reaction of a hydroxy-functional starter with epichlorohydrin and alkylene oxides using a double metal cyanide catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

can, as structural element, bring about higher polarity or hydrophilicity and form hydrogen bridge bonds

Methodology Applied
Scientific EffectHydrogen bonding:

Data Source

PatentUS10106644B2Polyoxyalkylenes containing guanidine and method for the production thereof
Publication Date: 2018.10.23 EVONIK OPERATIONS GMBH
  • US10106644B2 patent drawing
  • US10106644B2 patent drawing
  • US10106644B2 patent drawing

AI summary

The invention relates to polyoxyalkylenes which contain guanidine groups in the side chain, and to a process for their preparation.