Enol Ether Profragrance for Sustained Fragrance Release

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Solution Overview

Problem

The perfume industry faces challenges in creating long-lasting perfumes, as many fragrances are volatile and lack substantivity, leading to brief and intense perfuming effects, especially in applications like laundry where active substances are rinsed off, resulting in poor tenacity and short-lasting perfumes.

Innovation Solution

Enol ether compounds are used to tether volatile perfumery raw materials to a molecular anchor, releasing ketones, aldehydes, or formate esters through oxidation under ambient conditions, prolonging the perfuming effect by controlling the release profile.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If volatile perfumery raw materials are used directly, then the initial perfuming intensity is high, but the duration of action is short due to rapid evaporation and poor substantivity

Engineering Contradiction:
Improveduration of perfume effectVSAvoidsubstantivity of fragrance
Core Design Contradiction:
Duration of action of moving objectVSReliability

Solution Approach 1:

The volatile perfumery raw material is chemically modified in advance to form a profragrance compound with reduced volatility. This preliminary chemical transformation allows the fragrance to be stored stably and then released controllably under specific conditions (sweat, heat, friction), thereby extending the duration of action while improving substantivity.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The invention changes the chemical parameters of the fragrance molecule by forming a derivatized profragrance compound. This parameter change reduces the volatility and increases the molecular weight of the fragrance, allowing it to remain on the skin or fabric longer while still being able to release the original fragrance under appropriate conditions.

Inventive Principle:
Principle #35Parameter changes

2Duration of action of moving object

If profragrance compounds are used to extend perfume duration, then the longevity is improved, but the initial perfuming intensity may be reduced due to controlled release mechanisms

Engineering Contradiction:
Improvelongevity of fragranceVSAvoidperfuming effect intensity
Core Design Contradiction:
Duration of action of moving objectVSUse of energy by moving object

Solution Approach 1:

The profragrance compound releases the volatile perfumery raw material in a periodic manner rather than all at once. The release is triggered by periodic stimuli such as sweating, body heat, or friction, creating a sustained fragrance effect that maintains both longevity and adequate intensity over time.

Inventive Principle:
Principle #19Periodic action

Solution Approach 2:

The profragrance compound acts as an intermediary between the volatile raw material and the environment. It temporarily binds the volatile compound and releases it under specific conditions, thereby mediating the release profile to achieve both extended longevity and maintained intensity.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If standard perfumery ingredients are used in laundry applications, then the perfuming effect is achieved, but the tenacity is poor as substances are rinsed off easily

Engineering Contradiction:
Improvetenacity on laundryVSAvoidpersistence after washing
Core Design Contradiction:
ReliabilityVSDuration of action of moving object

Solution Approach 1:

The fragrance molecule is derivatized to change its physical parameters, specifically increasing molecular weight and reducing water solubility. This parameter change allows the fragrance to bind more strongly to fabric fibers and resist rinsing, thereby improving tenacity and persistence after washing.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The profragrance compound is applied to the laundry in advance, where it binds to the fabric. The volatile raw material is then released progressively during wear and washing cycles, ensuring the fragrance persists through multiple washings while maintaining effectiveness.

Inventive Principle:
Principle #10Preliminary action

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 enhances the longevity and intensity of perfumes by controlling the release of volatile compounds, ensuring a sustained perfuming effect even after washing and drying, addressing the issue of short-lived fragrances in various applications.

Implementation Method 1

exposing the compound of formula (I) to an environment wherein it is oxidized

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS20230257678A1Enol ether properfume
Publication Date: 2023.08.17 FIRMENICH SA
  • US20230257678A1 patent drawing
  • US20230257678A1 patent drawing
  • US20230257678A1 patent drawing

AI summary

The present invention relates to compounds of formula (I) as properfume compounds. In particular, the present invention relates to a method to release a compound being a ketone or aldehyde 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. Moreover, the present invention relates to a perfuming composition and a perfume consumer product comprising at least one compound of formula (I).