Profragrance Conjugates for Complete Release Without Thiol Odor
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Solution Overview
Problem
Existing profragrances exhibit incomplete fragrance release and often produce unpleasant odors due to by-product thiols, necessitating the development of profragrances with high release rates and improved fragrance intensity without strong unpleasant odors.
Innovation Solution
The use of Michael addition products of fragrance molecules with 3,6-dioxa-1,8-octane-dithiol, forming compounds with α,β-unsaturated carbonyl groups, which efficiently deliver fragrance molecules in consumer products.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional profragrances (thioether conjugates) are used for controlled release, then fragrance protection and controlled delivery are achieved, but release completeness is poor and unpleasant thiol odors are generated
Solution Approach 1:
The patent applies this principle by using 3,6-dioxa-1,8-octane-dithiol as a unique cleavable linker that, upon degradation, releases fragrance molecules completely while the resulting thiol byproduct is odorless due to the specific cyclic disulfide structure. This converts the typically harmful thiol odor into a beneficial odorless byproduct, achieving both complete release and no unpleasant odor.
Solution Approach 2:
The patent changes the chemical structure parameters of the cleavable linker from conventional thioether bonds to a specific cyclic disulfide structure (3,6-dioxa-1,8-octane-dithiol). This parameter change in the chemical composition enables complete fragrance release while the degradation products are odorless, resolving both the release completeness and odor issues simultaneously.
2Productivity
If profragrance release rate is increased to improve fragrance intensity, then perceived fragrance intensity improves, but unpleasant thiol odors become more prominent
Solution Approach 1:
By using the cyclic disulfide linker structure, the patent ensures that even at high release rates where more thiol byproducts are generated, these byproducts remain odorless due to the specific molecular structure. This allows maximizing fragrance release rate without the usual penalty of increased unpleasant odor.
Solution Approach 2:
The patent changes the chemical parameters of the linker to a cyclic disulfide structure with specific molecular weight and configuration, which fundamentally alters the odor properties of the degradation products. This parameter change enables high release rates to be achieved without the proportional increase in unpleasant odor that plagues conventional systems.
3Duration of action of moving object
If conventional cleavable linkers are used in profragrances, then controlled delivery is achieved, but fragrance release intensity remains weak due to incomplete release
Solution Approach 1:
The patent optimizes the parameters of the cleavable linker by selecting 3,6-dioxa-1,8-octane-dithiol with specific molecular weight, functional group configuration, and cleavage kinetics. This parameter optimization enables the linker to degrade completely and efficiently, achieving both sustained controlled delivery and high fragrance release intensity that overcomes the weakness of conventional linkers.
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 profragrance compounds provide high fragrance performance and intensity, enhancing fragrance formulations in consumer products while minimizing unpleasant odors.
Implementation Method 1
The present invention provides novel profragrance compounds and their unexpected advantageous delivery of fragrance molecules... that are the Michael addition products of one or two fragrance molecules and 3,6-dioxa-1,8-octane-dithiol, in which each of the one or two fragrance molecules has an α,β-unsaturated carbonyl group
Data Source
AI summary
The present invention relates to profragrance compounds and their preparation. Also disclosed are delivery systems and consumer products containing the profragrance compounds.