Polysiloxane conjugates as fragrance delivery systems

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Solution Overview

Problem

The perfume industry faces challenges in achieving prolonged and improved olfactory performance from perfuming ingredients due to volatility and poor substantivity, with existing polymer-based solutions offering modest performance and unsatisfactory dispersion and deposition.

Innovation Solution

Development of polysiloxane conjugates with a β-thio carbonyl moiety capable of releasing odoriferous molecules like α,β-unsaturated ketones or aldehydes, which are designed to provide controlled and enhanced fragrance release while maintaining flowable properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of moving object

If polymer-based ingredients are used to prolong the effect of active ingredients, then the duration of action is improved, but the release properties remain modest

Engineering Contradiction:
Improveduration of fragrance effectVSAvoidrelease properties
Core Design Contradiction:
Duration of action of moving objectVSProductivity

Solution Approach 1:

The invention uses styrene co-polymer combined with specific monomeric derivatives (isobornyl 2-mercapto-2-methylpropanoate and/or 3-mercaptopropyltrimethoxysilane) to create a composite fragrance delivery system. This composite approach allows the polymer matrix to provide prolonged release while the specific monomeric components enhance the release properties, resolving the contradiction between duration and release efficiency.

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If non-flowable crosslinked siloxane-based polymers are used to improve deposition, then the deposition performance is improved, but the dispersion becomes poor

Engineering Contradiction:
Improvedeposition performanceVSAvoiddispersion
Core Design Contradiction:
Manufacturing precisionVSStability of the object's composition

Solution Approach 1:

The invention changes the flowability parameter of siloxane-based polymers by adjusting crosslinking density and molecular weight, transforming non-flowable polymers into flowable forms. This parameter change maintains the deposition capability while improving dispersion properties, allowing the polymer to be effectively applied without aggregation issues.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If chemical binding of polymers to surface is promoted to improve fragrance delivery, then the fragrance delivery is improved, but the target surface is modified

Engineering Contradiction:
Improvefragrance deliveryVSAvoidsurface modification
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The invention introduces siloxane-based polymers as intermediary carriers between the fragrance molecules and the target surface. These polymers provide physical adsorption sites that enable fragrance delivery without requiring direct chemical bonding to the surface, thus maintaining surface integrity while achieving effective fragrance release.

Inventive Principle:
Principle #24Intermediary (Mediator)

4Quantity of substance

If standard free oil or commercial monomeric profragrances are used, then the fragrance intensity is maintained, but the flowable properties and substantivity are insufficient

Engineering Contradiction:
Improvefragrance intensityVSAvoidflowable properties
Core Design Contradiction:
Quantity of substanceVSEase of operation

Solution Approach 1:

The invention applies local quality by incorporating specific functional groups (mercapto groups) at specific positions within the polymer structure. This localized functionalization enhances both the flowable properties through molecular design and the substantivity through targeted interactions, while maintaining fragrance intensity released from these specific sites.

Inventive Principle:
Principle #3Local quality

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 polysiloxane conjugates demonstrate superior performance compared to free active molecules and prior art polymers, offering improved fragrance release and substantivity, ensuring prolonged odor benefits in perfumery applications.

Implementation Method 1

polysiloxane conjugates with a β-thio carbonyl moiety capable of releasing odoriferous molecules like α,β-unsaturated ketones or aldehydes

Methodology Applied
Scientific EffectDecomposition (chemical): Decomposition (biological)

Data Source

PatentUS9765282B2Polysiloxane conjugates as fragrance delivery systems
Publication Date: 2017.09.19 FIRMENICH SA
  • US9765282B2 patent drawing
  • US9765282B2 patent drawing
  • US9765282B2 patent drawing

AI summary

The present invention relates to the field of perfumery. More particularly, it concerns polymers derived from siloxane derivatives and comprising at least one β-thio carbonyl moiety capable of liberating an active molecule such as, for example, an α,β-unsaturated ketone or aldehyde. The present invention concerns also the use of polymers in perfumery as part of a perfuming or malodor counteracting composition as well as the perfuming compositions or perfumed articles comprising the invention's compounds.