Enol Ether Properfume Oxidation for Fragrance Longevity

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Solution Overview

Problem

The perfume industry faces challenges in creating long-lasting perfumes for volatile or poorly substantive perfumery raw materials, which often degrade quickly and fail to maintain their perfuming effect after washing or drying, particularly in applications like laundry.

Innovation Solution

Enol ether compounds are used to release carbonyl, formate ester, or alcohol compounds through oxidation, tethering volatile perfumery raw materials to a molecular anchor and triggering their release under specific environmental conditions, such as ambient oxygen, to enhance longevity and control fragrance release profiles.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If volatile perfumery raw materials are used to create fragrances, then the fragrance intensity is improved, but the duration of the perfuming effect deteriorates

Engineering Contradiction:

Improvefragrance intensityVSAvoidduration of perfuming effect

Core Design Contradiction:

Illumination intensityVSDuration of action of moving object

Solution Approach 1:

The patent applies preliminary action by pre-tethering volatile perfumery raw materials to a molecular anchor (enol ether compound) before application. The volatile compound is not released immediately but is held in reserve and released later through oxidation-triggered cleavage, thereby extending the duration of the perfuming effect while maintaining the original fragrance intensity when released.

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The enol ether compound acts as an intermediary molecular anchor that temporarily holds the volatile perfumery raw material. This intermediary structure enables the volatile compound to be deposited in greater amounts onto the surface (improving intensity) while being released controllably over time through oxidation (extending duration), thus resolving the contradiction between intensity and duration.

Inventive Principle:

Principle #24Intermediary (Mediator)

2Ease of manufacture

If volatile perfumery raw materials are applied to laundry, then the fragrance diffusion is improved, but the substantivity after washing deteriorates

Engineering Contradiction:

Improvefragrance diffusionVSAvoidsubstantivity after washing

Core Design Contradiction:

Ease of manufactureVSReliability

Solution Approach 1:

The volatile perfumery raw material is pre-bound to the enol ether molecular anchor before laundry application. This preliminary tethering allows the fragrance to be deposited in greater amounts onto the laundry surface (improving diffusion) while being protected from wash-off. The fragrance is released in-situ during wear through oxidation, ensuring persistence through washing and drying cycles.

Inventive Principle:

Principle #10Preliminary action

Solution Approach 2:

The enol ether compound serves as a mediator that bridges the volatile fragrance and the laundry substrate. It enables strong initial deposition (improving diffusion) while the oxidation-triggered release mechanism ensures the fragrance survives washing and drying (improving substantivity), thus resolving the contradiction between diffusion and reliability.

Inventive Principle:

Principle #24Intermediary (Mediator)

3Stability of the object's composition

If perfumery ingredients are protected against degradation, then the stability is improved, but the release of active compound deteriorates

Engineering Contradiction:

Improvestability of perfumery ingredientVSAvoidrelease of active compound

Core Design Contradiction:

Stability of the object's compositionVSProductivity

Solution Approach 1:

The patent extracts the volatile perfumery raw material from its unstable free state and separates it from degradation-prone environmental factors by tethering it to the enol ether molecular anchor. The active compound is held protected in this bound state (improving stability) and is selectively released only when oxidation occurs (maintaining productivity through controlled cleavage of the anchor).

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The enol ether compound acts as a protective intermediary that shields the volatile perfumery ingredient from degradation pathways (improving stability) while maintaining the capability for controlled release through oxidation-triggered cleavage (preserving productivity). The intermediary structure thus resolves the contradiction between protection and release.

Inventive Principle:

Principle #24Intermediary (Mediator)

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 method effectively prolongs the perfuming effect of volatile ingredients, providing a controlled and intensified fragrance diffusion that persists over time, even after washing or drying, addressing the limitations of traditional perfumes.

Implementation Method 1

a method to release a compound being a carbonyl of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV), by exposing the compound of formula (I) to an environment wherein it is oxidized

Methodology Applied

Scientific EffectOxidation: Oxidation

Data Source

PatentUS12252465B2Enol ether properfume

Publication Date: 2025.03.18 FIRMENICH SA

AI summary

Described herein are compounds of formula (I) as properfume compounds, as well as a method to release a compound being a carbonyl of formula (II), a formate ester of formula (III) and/or an alcohol of formula (IV), by exposing the compound of formula (I) to an environment wherein it is oxidized. Also described herein are a perfuming composition and a perfume consumer product including at least one compound of formula (I).