Thioether Derivatives for Controlled Release of Fragrance Molecules
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Solution Overview
Problem
The perfume industry faces challenges with volatile and non-substantive fragrances that lack long-lasting effects, particularly in applications like laundry, where traditional perfuming ingredients have poor tenacity and are quickly rinsed off, leading to brief and intense perfuming effects. Additionally, existing pro-fragrances are not atom-efficient, resulting in a low weight ratio of perfume to pro-fragrance and are negatively impacted by the use of short chain thiols, which are considered odorless and hydrophilic.
Innovation Solution
The development of short chain β-sulfur carbonyl moieties that efficiently liberate active molecules such as enones or enals, providing improved long-lasting olfactive performance, despite preconceptions against short chain thiols. These compounds are synthesized through [1,4]-addition reactions between odoriferous α,β-unsaturated ketones or aldehydes and sulfur-containing compounds, forming thioether derivatives that release pleasant fragrances.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If short chain β-sulfur carbonyl moieties are used, then atom-efficiency is improved, but olfactive performance is expected to deteriorate due to hydrophilicity and short chain characteristics
Solution Approach 1:
The patent changes the chain length parameter of the thiol moiety from the conventional long chain (C8-C18) to short chain (C3-C5), which improves atom-efficiency while surprisingly maintaining or enhancing olfactive performance. This parameter change directly resolves the contradiction by challenging the conventional wisdom that long chains are necessary for good olfactive performance.
Solution Approach 2:
The patent inverts the conventional approach by using short chain thiols instead of long chain thiols. While prior art recommended C8 or heavier thiols to avoid unpleasant odors and ensure performance, this patent successfully uses C3-C5 thiols, achieving both atom-efficiency and pleasant olfactive effects, thus applying the inversion principle to resolve the contradiction.
2Reliability
If long chain thiols (C8 or heavier) are used, then olfactive performance is improved, but atom-efficiency deteriorates due to low weight ratio of perfume to pro-fragrance
Solution Approach 1:
The patent changes the chain length parameter from long (C8-C18) to short (C3-C5), which reduces the molecular weight of the pro-fragrance while maintaining the active perfume molecule. This increases the weight ratio of perfume to pro-fragrance, thereby improving atom-efficiency while preserving olfactive performance.
Solution Approach 2:
The patent creates a simplified version of conventional pro-fragrances by using short chain analogs (C3-C5) instead of long chains (C8-C18). These short chain compounds copy the essential function of releasing active molecules while having lower molecular weight, thus improving atom-efficiency without sacrificing performance.
3Quantity of substance
If traditional perfuming ingredients are used, then fragrance intensity is achieved, but duration of action deteriorates due to poor substantivity and volatility
Solution Approach 1:
The patent applies preliminary action by using pro-fragrances that are precursors to the active perfume molecules. These pro-fragrances are applied first and then gradually release the active fragrance molecules over time through hydrolysis or other degradation processes, providing both initial fragrance intensity and extended duration of action.
Solution Approach 2:
The patent uses pro-fragrances as intermediary compounds that mediate between the applied substance and the active fragrance. The pro-fragrance serves as a carrier that releases the active perfume molecule gradually, extending the duration of action while maintaining fragrance intensity. The short chain β-sulfur carbonyl moiety acts as an effective intermediary for this controlled release.
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 short chain β-sulfur carbonyl moieties achieve superior olfactive performance and increased atom-efficiency, delivering a positive hedonic effect while maintaining fragrance intensity over time, even in applications where traditional ingredients would fail, such as in laundry and hard surface cleaners.
Implementation Method 1
short chain β-sulfur carbonyl moieties capable of liberating an active molecule, namely an enone or an enal, in a very efficient way
Implementation Method 2
P represents a group susceptible of generating a perfuming α,β-unsaturated ketone or aldehyde
Data Source
AI summary
The present invention relates to the field of perfumery. More particularly, it concerns short chain β-sulfur carbonyl moieties capable of liberating an active molecule, such as a perfuming α,β-unsaturated ketone or aldehyde. The present invention concerns also the use of said compounds in perfumery as well as the perfuming compositions or perfumed articles comprising the invention's compounds.