Enantiomeric Cyclohexylethyl Esters for Specific Malodor Counteraction

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Solution Overview

Problem

Existing methods for counteracting malodors are not specific and require high amounts of counteracting compositions to effectively eliminate particular malodors, with no disclosed effect of cyclohexylethyl carboxylic acid ester compounds against specific malodors.

Innovation Solution

The use of enantiomeric cyclohexylethyl carboxylic acid ester compounds, specifically (1R)-1-cyclohexylethyl butyrate and (1S)-1-cyclohexylethyl acetate, which selectively target and effectively counteract mold/mildew and sweat malodors respectively, allowing for malodor-specific counteraction at lower doses.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If conventional fragrance materials are used to mask malodors, then the malodor perception is reduced, but large quantities are required and no specific effect against particular malodors is achieved

Engineering Contradiction:
Improvemalodor perceptionVSAvoidamount of counteracting composition
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent applies local quality by using different enantiomers of cyclohexylethyl carboxylic acid esters for different malodor types. Specifically, (1R)-1-cyclohexylethyl butyrate is used for mold/mildew malodors while (1S)-1-cyclohexylethyl acetate is used for sweat malodors. This targeted approach allows each enantiomer to specifically address its corresponding malodor type, improving effectiveness while reducing the overall quantity needed compared to using generic fragrance materials for all malodors.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent employs parameter changes by utilizing the chiral configuration (enantiomeric form) of cyclohexylethyl carboxylic acid esters to achieve malodor-specific effects. The spatial arrangement of atoms in (1R) and (1S) enantiomers creates distinct interactions with different malodor compounds, allowing effective counteraction at lower concentrations than conventional fragrance materials that lack such specific molecular recognition.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If conventional fragrance materials are used to mask malodors, then the malodor perception is reduced, but the fragrance materials must be used in large quantities which increases cost and reduces efficiency

Engineering Contradiction:
Improvemalodor perceptionVSAvoidefficiency of malodor counteraction
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent improves productivity by implementing local quality through enantiomer-specific applications. Each enantiomer ((1R)-1-cyclohexylethyl butyrate for mold/mildew, (1S)-1-cyclohexylethyl acetate for sweat) is optimized for its target malodor type, creating a highly efficient counteraction mechanism that works at low concentrations. This specificity eliminates the need to use large quantities of generic fragrance materials, thereby increasing the efficiency of malodor counteraction.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent enhances efficiency through parameter changes in molecular configuration. The chiral centers in the cyclohexylethyl carboxylic acid ester molecules create enantiomers with distinct three-dimensional structures that selectively interact with specific malodor compounds. This molecular-level specificity allows for efficient malodor counteraction at low dosages, significantly improving productivity compared to conventional fragrance materials that require high concentrations to achieve any masking effect.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If racemic cyclohexylethyl carboxylic acid ester compounds are used, then malodor counteraction is achieved, but the effectiveness is lower compared to specific enantiomers

Engineering Contradiction:
Improvemalodor counteraction effectVSAvoidconsistency of malodor counteraction
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent resolves this contradiction by applying local quality through enantiomer selection. Instead of using racemic mixtures containing both (1R) and (1S) forms, the patent specifies using individual enantiomers matched to specific malodor types: (1R)-1-cyclohexylethyl butyrate for mold/mildew and (1S)-1-cyclohexylethyl acetate for sweat. This targeted approach ensures consistent and reliable malodor counteraction by eliminating the variability inherent in racemic mixtures, where only half of the molecules (the correct enantiomer) would be effective against each malodor type.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent improves reliability through parameter changes in stereochemistry. By controlling the chiral configuration to produce pure enantiomers rather than racemic mixtures, the patent ensures that 100% of the molecules possess the correct spatial arrangement for effective interaction with specific malodor compounds. This eliminates the 50% inefficiency inherent in racemic mixtures and provides consistent, reliable malodor counteraction across different applications and conditions.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2281581B1Method of using cyclohexylethyl carboxylic acid esters for reducing malodors
Publication Date: 2013.04.17 INTERNATIONAL FLAVORS & FRAGRANCES INC
  • EP2281581B1 patent drawing
  • EP2281581B1 patent drawing
  • EP2281581B1 patent drawing

AI summary

The present invention pertains to a method of counteracting a malodor by introducing a malodor counteracting effective amount of an enantiomeric compound selected from the group consisting of (1R)-1-cyclohexylethyl butyrate and (1S)-1-cyclohexylethyl acetate.