N-Oxide Hydrotropes for Biodegradable Cleaning Formulations

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Solution Overview

Problem

Existing surfactants, particularly quaternary ammonium compounds used as hydrotropes, face environmental and safety concerns due to their persistence and toxicity, necessitating the development of bio-based alternatives with low ecotoxicity for cleaning formulations.

Innovation Solution

Development of a compound of formula (I), derived from ethoxylating a secondary amine and oxidizing it to an N-oxide, which serves as an efficient hydrotrope for nonionic surfactants, enhancing cleaning performance while being readily biodegradable and environmentally friendly.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If quaternary ammonium compounds are used as hydrotropes to solubilize surfactants, then cleaning performance is improved, but environmental persistence and ecotoxicity increase

Engineering Contradiction:

Improvecleaning performanceVSAvoidecotoxicity

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical structure parameters of the hydrotrope by introducing a bio-based amine component with specific chain lengths (C8-C30) and ethoxylation degree (n≥8), transforming it from a conventional quaternary ammonium compound to an N-oxide derivative that maintains cleaning efficacy while reducing ecotoxicity and improving biodegradability

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining a fatty amine chain (R), a short alkyl group (R1), and an ethoxylated N-oxide head group, where the synergistic interaction between these components achieves both effective hydrotrope performance and reduced environmental impact

Inventive Principle:

Principle #40Composite materials

2Stability of the object's composition

If conventional hydrotropes are used to achieve clear solutions, then solubility is improved, but environmental persistence increases

Engineering Contradiction:

ImprovesolubilityVSAvoidenvironmental persistence

Core Design Contradiction:

Stability of the object's compositionVSDuration of action of stationary object

Solution Approach 1:

The patent designs the hydrotrope to be readily biodegradable (short-lived in the environment) while maintaining its solubilization function, effectively replacing persistent conventional hydrotropes with a bio-based alternative that breaks down quickly after performing its cleaning function

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

3Reliability

If quaternary ammonium salts are used as hydrotropes, then cleaning efficacy is improved, but safety concerns and labeling requirements increase

Engineering Contradiction:

Improvecleaning efficacyVSAvoidsafety concerns

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent converts the potentially harmful quaternary ammonium structure into a beneficial N-oxide derivative structure that retains cleaning efficacy while eliminating toxicity concerns, effectively transforming a harmful chemical class into a safe alternative

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 compound of formula (I) effectively solubilizes nonionic surfactants, providing excellent cleaning performance comparable to existing hydrotropes like BEROL® R648 NG, with high biodegradability and low toxicity, and a Renewable Carbon Index (RCI) exceeding 50%, addressing regulatory and environmental issues.

Implementation Method 1

compounds of the formula (I) are very efficient hydrotropes for nonionic surfactants

Methodology Applied

Scientific EffectHydrotropy:

Implementation Method 2

oxidizing the ethoxylated amine of the formula (III) to give the N-oxide of formula (I)

Methodology Applied

Scientific EffectOxidation: Oxidation

Data Source

PatentUS20250382549A1Multifunctional n-oxide hydrotropes, cleaning formulations containing them and use thereof

Publication Date: 2025.12.18 AKZO NOBEL CHEMICALS INTERNATIONAL BV

AI summary

An N-oxide compound has the formula (I):whereinR represents a fatty linear or branched, saturated or unsaturated alkyl group having 8-30 carbon atoms;R1 represents a linear or branched, saturated or unsaturated lower alkyl group having 1-8 carbon atoms; andn represents at least 8 and at most 25.The compound of formula (I) acts as a hydrotrope and is useful for cleaning applications. Processes of preparing the compound, cleaning compositions containing the compound, and methods of using the compound to clean an object are also disclosed.