Polyalkylene Glycol Antimicrobial Compound for Low-Concentration Use

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Solution Overview

Problem

Existing antimicrobial compounds like octenidine dihydrochloride are not sufficiently effective and efficient in cosmetic and pharmaceutical compositions, necessitating improved formulations with enhanced antimicrobial properties.

Innovation Solution

A novel antimicrobial compound with a specific structure, derived from the reaction of 4-(R 1< -amino)-pyridine with a disubstituted polyalkylene glycol derivative, exhibits improved water solubility and efficacy at low concentrations, produced efficiently through a controlled reaction process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If octenidine dihydrochloride is used as an antimicrobial compound, then it provides bactericidal, fungicidal, and antiviral properties, but it requires higher concentrations (0.1 to 2.0 wt.%) to achieve effective disinfection

Engineering Contradiction:
Improveantimicrobial efficacyVSAvoidconcentration required
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent modifies the chemical structure of octenidine by replacing the traditional alkyl chain with a polyalkylene glycol derivative chain of specific length (2-6 ether groups). This structural parameter change fundamentally alters the compound's properties, enabling it to achieve the same or better antimicrobial efficacy at significantly lower concentrations (0.001 to 6 wt.%, preferably 0.01 to 1 wt.%), thus resolving the contradiction between efficacy and required quantity

Inventive Principle:
Principle #35Parameter changes

2Reliability

If the antimicrobial compound structure is modified to improve efficacy at low concentrations, then water solubility and efficacy are enhanced, but the molecular structure complexity increases

Engineering Contradiction:
Improveantimicrobial efficacyVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent systematically varies a single key parameter - the number of ether groups (n = 2-6) in the polyalkylene glycol chain - while maintaining the overall molecular framework similar to octenidine. This controlled parameter change approach allows optimization of water solubility and antimicrobial efficacy without excessive structural complexity, achieving the desired balance between performance and structural simplicity

Inventive Principle:
Principle #35Parameter changes

3Reliability

If a disubstituted polyalkylene glycol derivative with 2-6 ether groups is used in the reaction, then the antimicrobial compound achieves high water solubility and efficacy, but the reaction conditions and process control become more specific

Engineering Contradiction:
Improvewater solubilityVSAvoidreaction condition control
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent defines specific parameter ranges for the polyalkylene glycol derivative (2-6 ether groups) that optimize both water solubility and antimicrobial activity. While this requires precise control of the number of ether groups, the patent provides clear guidance on achievable results within this range, balancing manufacturing precision requirements with performance optimization

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 new compound demonstrates high efficacy against bacteria, fungi, and viruses, even at low concentrations, and is suitable for use in cosmetic and pharmaceutical compositions, ensuring effective preservation and disinfection.

Implementation Method 1

The compound is a cationic antimicrobial with a positively charged nitrogen atom that interacts with negatively charged bacterial cell membranes

Methodology Applied
Scientific EffectElectrostatic interaction: Electrostatic Induction

Implementation Method 2

the antimicrobial compound according to the invention has very good water solubility

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentEP4389219B1Antimicrobial compound, method for its preparation and use of the antimicrobial compound for the preparation of a cosmetic or pharmaceutical composition
Publication Date: 2025.09.10 AEROCHEMICA DR DEPPE GMBH
  • EP4389219B1 patent drawing
  • EP4389219B1 patent drawing
  • EP4389219B1 patent drawing

AI summary

The present invention provides an antimicrobial compound with formula (I), wherein R1 is an alkyl group with 4 to 18 carbon atoms, or a cycloalkyl group with 5 to 12 carbon atoms, or a (poly)alkylene glycol group with 1 to 6 alkoxy units, or a phenyl group, or a benzyl group, and R2 is an alkyl group with 2, 3, or 4 carbon atoms, and n is an integer from 1 to 15, and [2A-] represents two monovalent anions (2A) or one divalent anion (A2-). Furthermore, a process for preparing the antimicrobial compound, its use, and a cosmetic or pharmaceutical composition are disclosed.