Status of Related Application

This application claims priority to U.S. Provisional Patent Application No. 63/313,755, filed February 25, 2022, the contents hereby incorporated by reference as if set forth in its entirety.

Background of Invention

Fragrance compositions are used in a variety of consumer products to deliver several benefits ranging from masking unpleasant base or malodors, providing a pleasant olfactory aesthetic benefit, inducing consumer feelings (e.g., happiness, stimulation, relaxation, etc.), and implying a signal of product attributes and function (e.g., freshness, cleanliness, etc.). Effort has been made to achieve fragrance compositions that exhibit superior or enhanced strength leading to consumer benefits.

In general, fragrance strength correlates with fragrance concentrations. Consumer products of high fragrance strength with long lastingness generally contain high levels of fragrance ingredients and therefore commend high prices. Consequently, fragrance enhancers which are used at low levels , without altering the inherent hedonics, reduce the use of fragrance ingredients and have become valuable tools in achieving the desired fragrance strength and longevity with less amount of fragrance ingredients.

Summary of the Invention

This invention relates to a fragrance enhancer represented by Formula I set forth below:

R ¹ -(S) _n -R ²

Formula I wherein R ¹ and R ² each independently represent C1-C12 alkyl, C2-C12 alkenyl, C2- Cn alkynyl, C2-Ci2 acyl or C2-C12 acetate; optionally substituted by one or more hydroxyl, ether, thiol, sulfide, polysulfide, cyclopentyl, cyclohexyl, cyclopentadienyl, benzyl, pyridinyl or furanyl groups; wherein n represents an integer of 2-8, preferably 2-6, and more preferably 2 or 3; and wherein R ¹ and R ² may be linked to form a ring or a polymer.

This invention further relates to a fragrance enhancer represented by Formula II set forth below: wherein R represents C1-C12 alkyl, C2-C 12 alkenyl, C2-Ci2 alkynyl, C2-Ci2 acyl or C2- C12 acetate; optionally substituted by one or more hydroxyl, ether, thiol, sulfide, polysulfide, cyclopentyl, cyclohexyl, cyclopentadienyl, benzyl, pyridinyl or furanyl groups.

This invention provides a method of enhancing the fragrance of a fragrance composition comprising the step of adding an effective amount of the compound provided above to the fragrance composition.

In another embodiment, the present invention is directed to a fragrance composition comprising a fragrance ingredient and an effective amount of the compound provided above.

In another embodiment, the present invention is directed to a fragrance product containing a fragrance composition comprising a fragrance ingredient and an effective amount of the compound provided above.

These and other embodiments of the present invention will be apparent by reading the following specification. Detailed Description of the Invention

The compounds of the present invention can be, for example, but not limited to, represented by the following structures:

1 ,3 -diisopentyltrisulfane

3-(isopentyldisulfanyl)butan-2-one

3-(isopentyltrisulfanyl)butan-2-one

1 ,2-bis(3 -methylbut-2-en- 1 -yl)disulfane 1 ,3 -bi s (3 -methylbut-2-en- 1 -yl)trisulfane

3 -((3 -methylbut-2-en- 1 -yl)disulfanyl)butan-2-one

3 -((3 -methylbut-2-en- 1 -yl)trisulfanyl)butan-2-one

3,3'-disulfanediylbis(butan-2-one)

3,3'-trisulfanediylbis(butan-2-one)

3-((furan-2-ylmethyl)disulfanyl)butan-2-one

3-((furan-2-ylmethyl)trisulfanyl)butan-2-one

1 ,3 -bis(furan-2-ylmethyl)trisulfane

Additional compounds of the present invention include, for example, but not limited to, 3,3 '-dithiobis(l -hexanol) (CAS 344738-34-7), 3-((furanylmethyl)disulfanyl)hexan-l-ol, or their mixture with furfuryl disulfide (CAS 4437-20-1); (2-methyl-3 -furyl) furfuryl disulfide (CAS 109537-55-5), di(2-methylfuran-3-yl) disulfide (CAS 28588-75-2), or their mixture with furfuryl disulfide; 3, 3'-dithiobis[2 -butanol] (CAS 1129288-51-2), 3-((furanylmethyl)disulfanyl)butan-2-ol, or their mixture with furfuryl disulfide; ((cyclohexyldisulfanyl)methyl)furan (CAS 2427536-75-0), dicyclohexyl disulfide (CAS 2550-40-5), or their mixture with furfuryl disulfide; diethoxy carbonylmethyl disulfide (CAS 1665-65-2), ethyl 2-((furanylmethyl)disulfanyl)acetate, or their mixture with furfuryl disulfide; dibenzoyl disulfide (CAS 644-32-6), (furanylmethyl)benzo(dithioperoxoate), or their mixture with furfuryl disulfide; 2-pyridyl disulfide (CAS 2127-03-9), 2-((furanylmethyl)disulfanyl)pyridine, or their mixture with furfuryl disulfide; bis(2 -ethoxy- 1 -methyl -2 -oxoethyl) disulfide (CAS 6328-50-3), ethyl 2-

((furanylmethyl)disulfanyl)propanoate, or their mixture with furfuryl disulfide; l,4-bis(furan-2- ylmethyl)tetrasulfane (CAS 2427537-09-3), 1,4,7,8-dioxadithiecane (CAS 6573-57-5), 1,4-dioxa- 7,8,9-trithiacycloundecane (CAS 81328-01-0), triethylene glycol dithiol homopolymer (CAS 911218-12-7), copolymer of l,8-dimercapto-3,6-dioxaoctane with sulfur and furfuryl mercaptan, copolymer of l,8-dimercapto-3,6-dioxaoctane with sulfur, and any mixture thereof with difurfuryl disulfide and/or l,3-bis(furan-2-ylmethyl)trisulfane (CAS 71243-23-7). Those with skill in the art will recognize that the compounds of the present invention contain chiral centers, thereby providing numerous isomers of the claimed compounds. The compounds described herein include isomeric mixtures as well as single isomers that may be separated using techniques known to those having skill in the art. Suitable techniques include chromatography such as high performance liquid chromatography, referred to as HPLC, and particularly silica gel chromatography and gas chromatography trapping known as GC trapping. Yet, commercial products are mostly offered as isomeric mixtures.

It is unexpectedly found that the compound of the present invention, when incorporated in a fragrance composition at a level that is close to or lower than its odor detection threshold, provides enhanced fragrance strength and longevity without altering the odor characters of the fragrance composition to which it is added. A desired fragrance effect can therefore be achieved with less amount of fragrance ingredients. In particular, superior fragrance enhancement of the present invention is achieved in the presence of moisture such as water and heat such as at an elevated temperature of about 30-90 °C, preferably 40-80 °C.

The compounds of the present invention can be used in combination with other perfuming compositions, solvents, adjuvants and the like. The nature and variety of the other ingredients that can also be employed are known to those with skill in the art. Many types of fragrances can be employed in the present invention, the only limitation being the compatibility with the other components being employed. Suitable fragrances include but are not limited to fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, raspberry; musk, flower scents such as lavender-like, rose-like, iris-like, carnation-like. Other pleasant scents include herbal and woodland scents derived from pine, spruce and other forest smells. Fragrances may also be derived from various oils, such as essential oils, or from plant materials such as peppermint, spearmint and the like.

A list of suitable fragrances is provided in US Pat. No. 4,534,891, the contents of which are incorporated by reference as if set forth in its entirety. Another source of suitable fragrances is found in Perfumes. Cosmetics and Soaps. Second Edition, edited by W. A. Poucher, 1959. Among the fragrances provided in this treatise are acacia, cassis, chypre, cyclamen, fem, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, freshly-cut hay, orange blossom, orchid, reseda, sweet pea, trefle, tuberose, vanilla, violet, wallflower, and the like. Fragrance compositions comprising the compounds of the present invention can further contain a complementary fragrance compound. The term “complementary fragrance compound” as used herein is defined as a fragrance compound selected from the group consisting of 2-[(4- methylphenyl)methylene]-heptanal (Acalea), iso-amyl oxyacetic acid allylester (Allyl Amyl Glycolate), 4,4,10,10,11,12, 12-heptamethyl-3 -oxatricyclo [7.3.0.0<2,6>]dodecane (Amber

Xtreme), (3,3-dimethylcyclohexyl)ethyl ethyl propane-1, 3-dioate (Applelide), (E/Z)- 1 -ethoxy- 1- decene (Arctical), 2-ethyl-4-(2,2,3-trimethyl-3-cyclo-penten-l-yl)-2-buten-l-ol (Bacdanol), 2- methyl-3-[(l,7,7-trimethylbicyclo[2.2.1]hept-2-yl)oxy] exo- 1 -propanol (Bomafix), 1,2, 3, 5, 6, 7- hexahydro-l,l,2,3,3-pentamethyl-4H-inden-4-one (Cashmeran), trimethylcyclopentenylmethyloxabicyclooctane (Cassiffix), 1, l-dimethoxy-3,7-dimethyl-2,6- octadiene (Citral DMA), 3,7-dimethyl-6-octen-l-ol (Citronellol), 3A,4,5,6,7,7A-hexahydro-4,7- methano-7H-inden-5/6-yl acetate (Cyclacet), 3A,4,5,6,7,7A-hexahydro-4,7-methano-7H-inden- 5/6-yl propinoate (Cyclaprop), 3A,4,5,6,7,7A-hexahydro-4,7-methano-lG-inden-5/6-yl butyrate (Cyclobutanate), l-(2,6,6-trimethyl-3-cyclohexen-l-yl)-2-buten-l-one (Delta Damascene), 3-(4- ethylphenyl)-2,2-dimethyl propanenitrile (Fleuranil), 3-(O/P-ethylphenyl) 2,2-dimethyl propionaldehyde (Floralozone), tetrahydro-4-methyl-2-(2-methylpropyl)-2H-pyran-4-ol (Floriffol), l,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma -2-benzopyran (Galaxolide), l-(5,5-dimethyl-l-cyclohexen-l-yl)pent-4-en-l-one (Galbascone), E/Z-3,7- dimethyl-2,6-octadien-l-yl acetate (Geranyl Acetate), a-methyl-l,3-benzodioxole-5-propanal (Helional), l-(2,6,6-trimethyl-2-cyclohexen-l-yl)-l,6-heptadien-3-one (Hexalon), (Z)-3 -hexenyl - 2-hydroxybenzoate (Hexenyl Salicylate, CIS-3), 4-(2,6,6-trimethyl-2-cyclohexen-l-yl)-3-buten-2- one (Ionone a), l-(l,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthale nyl)-ethan-l-one (Iso E Super), methyl 3 -oxo-2 -pentylcyclopentaneacetate (Kharismal), 2,2,4-trimethyl-4-phenyl- butanenitrile (Khusinil), 3,4,5,6,6-pentamethylhept-3-en-2-one (Koavone), 3/4-(4-hydroxy-4- methyl-pentyl) cyclohexene- 1-carboxaldehyde (Lyral), 3-methyl-4-(2,6,6-trimethyl-2- cyclohexen-l-yl)-3-buten-2-one (Methyl Ionone y), l-(2,6,6-trimethyl-2-cyclohexen-l-yl) pent-1- en-3-one (Methyl Ionone a Extra, Methyl Ionone N), 3-methyl-4-phenylbutan-2-ol (Muguesia), cyclopentadec-4-en-l-one (Musk Z4), 3,3,4,5,5-pentamethyl-l l,13- dioxatricyclo[7.4.0.0<2,6>]tridec-2(6)-ene (Nebulone), 3,7-dimethyl-2,6-octadien-l-yl acetate (Neryl Acetate), 3,7-dimethyl-l,3,6-octatriene (Ocimene), ortho-tolylethanol (Peomosa), 3- methyl-5 -phenylpentanol (Phenoxanol), 1 -methyl -4-(4-methyl-3 -pentenyl) cyclohex-3-ene-l- carboxaldehyde (Precyclemone B), 4-methyl-8-methylene-2 -adamantanol (Prismantol), 2-ethyl-4- (2,2,3 -trimethyl-3-cyclopenten-l-yl)-2-buten-l-ol (Sanjinol), 2-methyl-4-(2,2,3-trimethyl-3- cyclopenten- 1 -yl)-2-buten- 1 -ol (Santaliff), 3 -[cis-4-(2-methylpropyl)cyclohexyl]propanal

(Starfleur), Terpineol, 2,4-dimethyl-3 -cyclohexene- 1-carboxaldehyde (Triplal), decahydro- 2,6,6,7,8,8-hexamethyl-2H-indeno[4,5-B]furan (Trisamber), 2-tert-butylcyclohexyl acetate (Verdox), (3E)-4-methyldec-3-en-5-one (Veridian), 4-tert-butylcyclohexyL acetate (Vertenex), acetyl cedrene (Vertofix), 3,6/4,6-dimethylcyclohex-3-ene-l-carboxaldehyde (Vertoliff) and (3Z)- l-[(2-methyl-2-propenyl)oxy]-3-hexene (Vivaldie).

As used herein, the term “a” or “an” is understood to mean one or more. The term “a compound” is understood to mean one or more of the compounds represented by Formula I or Formula II as described herein. The compounds of the present invention can be prepared according to the known methods (e.g., US Patent No. 2237625; Harpp, et al., (1979) J. Org. Chem., 44(23): 4140-4144).

The terms “fragrance formulation”, “fragrance composition”, and “perfume composition” mean the same and refer to a consumer composition that is a mixture of compounds including, for example, alcohols, aldehydes, ketones, esters, ethers, lactones, nitriles, natural oils, synthetic oils, and mercaptans, which are admixed so that the combined odors of the individual components produce a pleasant or desired fragrance. The fragrance formulation of the present invention is a consumer composition comprising a fragrance ingredient and a compound of the present invention. The fragrance formulation of the present invention comprises a fragrance ingredient, a compound of the present invention and further a complementary fragrance compound as defined above.

The terms “fragrance product” and “functional product” mean the same and refer to a consumer product containing a fragrance ingredient that adds fragrance or masks malodor. Fragrance products may include, for example, perfumes, colognes, toilet water, bar soaps, liquid soaps, shower gels, foam baths, cosmetics, personal care and skin care products such as creams, lotions and shaving products, hair care products for shampooing, rinsing, conditioning, bleaching, coloring, dyeing and styling, deodorants and antiperspirants, feminine care products such as tampons and feminine napkins, baby care products such as diapers, bibs and wipes, family care products such as bath tissues, facial tissues, paper handkerchiefs or paper towels, air care products such as fragrance diffusers including reed diffusers, liquid wicks, candles, plug-in diffusers and gel diffusers, cosmetic preparations, cleaning products and disinfectants such as detergents, dishwashing materials, scrubbing compositions, glass and metal cleaners such as window cleaners, countertop cleaners, floor and carpet cleaners, toilet cleaners and bleach additives, laundry products such as washing agents including all-purpose, heavy duty, and hand washing or fine fabric washing agents, rinse additives, fabric conditioners, fabric softeners including fabric softener sheets, fabric refreshers and ironing spray, dental and oral hygiene products such as toothpastes, tooth gels, dental flosses, denture cleansers, denture adhesives, dentifrices, tooth whitening and mouthwashes, health care and nutritional products and food products such as snack and beverage products. The fragrance product of the present invention is a consumer product that contains a compound of the present invention, wherein the consumer product is preferably an air care product such as a reed diffuser, a liquid wick, a candle, a plug-in diffuser or a gel diffuser; or a laundry product such as a washing agent, a rinse additive, a fabric conditioner, a fabric softener or an ironing spray.

The term “fragrance enhancement” is understood to mean the increase of fragrance strength and/or longevity. The term “fragrance enhancer” is understood to mean a compound that provides fragrance enhancement. The term “improving” in the phrase “improving, enhancing or modifying a fragrance formulation" is understood to mean raising the fragrance formulation to a more desirable character. The term “enhancing” is understood to mean making the fragrance formulation greater in effectiveness or providing the fragrance formulation with an improved character. The term “modifying” is understood to mean providing the fragrance formulation with a change in character.

The term “olfactory acceptable amount” is understood to mean the amount of a fragrance ingredient in a fragrance composition, wherein the fragrance ingredient will contribute its individual olfactory characteristics. However, the olfactory effect of the fragrance composition will be the sum of effect of each of the fragrance ingredients. The compound of the present invention can be used to improve or enhance the aroma characteristics of the fragrance composition, or to reduce the amount of fragrance ingredients in the fragrance composition.

The term “effective amount” refers to the amount of a fragrance enhancer in a fragrance composition, wherein the fragrance enhancer provides fragrance enhancement. In the present invention, “an effective amount” is preferably the amount of a compound of the present invention in a fragrance composition, wherein the compound provides fragrance enhancement without altering the odor characters of the fragrance composition. The effective amount is preferably close to or lower than the odor detection threshold, which refers to the lowest vapor concentration of an odorant that can be olfactorily detected. The average odor detection threshold of the compounds of the present invention is about 50 ppm.

The effective amount of the compounds of the present invention employed in a fragrance composition varies from about 1 ppt to about 10,000 ppm, preferably from about 10 ppt to about 1,000 ppm, more preferably from about 0.1 to about 100 ppm, and even more preferably from about 0.5 to about 50 ppm. Those with skill in the art will be able to employ the desired amount to provide desired fragrance effect and intensity. In addition to the compounds of the present invention, other materials can also be used in conjunction with the fragrance formulation to encapsulate and/or deliver the fragrance. Some well-known materials are, for example, but not limited to, polymers, oligomers, other non-polymers such as surfactants, emulsifiers, lipids including fats, waxes and phospholipids, organic oils, mineral oils, petrolatum, natural oils, perfume fixatives, fibers, starches, sugars and solid surface materials such as zeolite and silica. Some preferred polymers include polyacrylate, polyurea, polyurethane, polyacrylamide, polyester, polyether, polyamide, poly(acrylate-co-acrylamide), starch, silica, gelatin and gum Arabic, alginate, chitosan, polylactide, poly(melamine-formaldehyde), poly(urea-formaldehyde), or a combination thereof.

A fragrance formulation containing the compound of the present invention can be further incorporated in a fragrance product, wherein the amount of the compound varies from about 0.1 pptto about 1,000 ppm, preferably from about 0.5 pptto about 100 ppm. For example, the amount of the compound can be from about 1 ppt to about 100 ppm or preferably from about 10 ppt to about 50 ppm in a candle, from about 1 ppt to about 100 ppm or preferably from about 5 ppt to about 10 ppm in a plug-in diffuser, or from about 0.5 ppt to about 100 ppm or preferably from about 1 ppt to about 50 ppm in a laundry product. In a preferred embodiment, the fragrance product is used at a temperature of from about 30 to about 90 °C, preferably from about 40 to about 80 °C.

In addition, a fragrance composition comprising the compounds of the present invention are also surprisingly found to provide superior ingredient performance and possess unexpected advantages in malodor counteracting applications such as body perspiration, environmental odor such as mold and mildew, bathroom, and etc. A fragrance composition comprising the compounds of the present invention substantially eliminate the perception of malodors and/or prevent the formation of such malodors, thus, can be utilized with a vast number of functional products. Malodor counteracting effective amount is understood to mean the amount of the inventive malodor counteractant employed in a functional product that is organoleptically effective to abate a given malodor while reducing the combined intensity of the odor level, wherein the given malodor is present in air space or has deposited on a substrate. The exact amount of malodor counteractant agent employed may vary depending upon the type of malodor counteractant, the type of the carrier employed, and the level of malodor counteractancy desired. In general, the amount of malodor counteractant agent present is the ordinary dosage required to obtain the desired result. Such dosage is known to the skilled practitioner in the art. In a preferred embodiment, when used in conjunction with malodorous solid or liquid functional products, e.g., soap and detergent, a fragrance composition comprising the compounds of the present invention may be present in an amount ranging from about 0.005 to about 50 weight percent, preferably from about 0.01 to about 20 weight percent, and more preferably from about 0.05 to about 5 weight percent, and when used in conjunction with malodorous gaseous functional products, a fragrance composition comprising the compounds of the present invention may be present in an amount ranging from about 0.1 to 10 mg per cubic meter of air.

The following are provided as specific embodiments of the present invention. Other modifications of this invention will be readily apparent to those skilled in the art. Such modifications are understood to be within the scope of this invention. As used herein all percentages are weight percent unless otherwise noted, ppm is understood to stand for parts per million, ppb is understood to stand for parts per billion, ppt is understood to stand for parts per trillion, L is understood to be liter, mL is understood to be milliliter, g is understood to be gram, Kg is understood to be kilogram, mol is understood to be mole, mmol is understood to be millimole, psi is understood to be pound-force per square inch, and mmHg be millimeters (mm) of mercury (Hg). IFF as used in the examples is understood to mean International Flavors & Fragrances Inc., New York, NY, USA.

Example I: Preparation of Sulfide Compound Mixtures

A 3-((furan-2-ylmethyl)disulfanyl)butan-2-one mixture (Mixture 1) was prepared according to known methods (e.g., US Patent No. 2237625; Harpp, et al., (1979) J. Org. Chem., 44(23): 4140-4144). Mixture 1 contained 3,3'-disulfanediylbis(butan-2-one), 3-((furan-2- ylmethyl)disulfanyl)butan-2-one, furfuryl disulfide, 3,3'-trisulfanediylbis(butan-2-one), 3-((furan- 2-ylmethyl)trisulfanyl)butan-2-one and l,3-bis(furan-2-ylmethyl)trisulfane with a weight ratio of about 17:45:29: 1:2:6.

The obtained Mixture 1 had the following NMR spectral characteristics:

¹ H NMR (600 MHz, CDC1 ₃ ) 5: 7.40, 6.20-6.35, 3.70-4.10, 3.30-3.70, 2.25-2.35, 1.35-1.50

A 3-((3-methylbut-2-en-l-yl)disulfanyl)butan-2-one mixture (Mixture 2) was similarly prepared. Mixture 2 contained 3,3'-disulfanediylbis(butan-2-one), 3-((3-methylbut-2-en-l- yl)disulfanyl)butan-2-one, l,2-bis(3-methylbut-2-en-l-yl)disulfane, 3,3'-trisulfanediylbis(butan-2- one), 3-((3-methylbut-2-en-l-yl)trisulfanyl)butan-2-one and l,3-bis(3-methylbut-2-en-l- yl)trisulfane with a weight ratio of about 34:45:7:5:7:2.

The obtained Mixture 2 had the following NMR spectral characteristics: ¹ H NMR (500 MHz, CDC1 ₃ ) 5: 5.05-5.15, 3.40-3.70, 3.20-3.50, 2.15-2.25, 1.55-1.70, 1.25-1.40

A 3,3'-disulfanediylbis(butan-2-one) mixture (Mixture 3) was similarly prepared. Mixture 3 contained 3,3'-disulfanediylbis(butan-2-one) and 3,3'-trisulfanediylbis(butan-2-one) with a weight ratio of about 3:2.

The obtained Mixture 3 had the following NMR spectral characteristics:

‘H NMR (600 MHz, CDCI3) 5: 3.54 (q, J = 7.0 Hz, 1H), 3.49 (q, J = 7.0 Hz, 1H), 2.28 (s, 3H), 2.27 (s, 3H), 1.39 (d, J = 7.0 Hz, 3H), 1.38 (d, J = 7.0 Hz, 3H) Example II: Inherent Odor Properties of Sulfide Compound Mixtures

Sulfide compound mixtures obtained above were prepared in an odorless solvent, isopropyl myristate (IPM), to provide a series of solutions of various concentrations. The inherent odor properties of sulfide compound mixtures were evaluated using odor strength of 0 to 10, where 0 = none, 1 = very weak, 5 = moderate, 10 = extremely strong.

The odor profiles and averaged scores of Mixture 1 are reported in the following:

At 0.001 and 1 ppm, Mixture 1 exhibited no odor; atlO ppm, very low odor was detected.

The odor profiles and averaged scores of Mixture 2 are reported in the following:

At 0.001 and 1 ppm, Mixture 2 exhibited no odor; at 10 and 100 ppm, very low odor was detected. The odor profiles and averaged scores of Mixture 3 are reported in the following:

At 0.001, 1 and 10 ppm, Mixture 3 exhibited no odor.

Example III: Fragrance Enhancement in Burning Candles

Modeling Burning Candles: A candle base that had freshly baked cookie, lemon and warm vanilla notes was prepared based on Applicants’ proprietary formulations for assessing the effectiveness of sulfide compounds in burning candles.

Preparation of Test Samples: The candle base was used as the control sample. Mixture 1 obtained above was added into the candle base to provide test samples with final concentrations of sulfide compounds at 0.001, 1 and 10 ppm, respectively.

Testing Procedure: Test was conducted in a smelling booth. Each sample was lit in the smelling booth for 15 minutes prior to the sensory evaluation. The temperature of the wax reached about 60-80 °C. The control and test samples were presented in a blind and random order to a group of internal panelists.

Results and Discussion: The odor profiles and averaged scores are reported in the following:

Mixture 1 provided fragrance enhancement in burning candles at 1 ppm. The fragrance enhancement was significantly intense at 10 ppm.

Example IV: Fragrance Enhancement in Plug-in Diffusers

Modeling Plug-in Diffusers: A plug-in diffuser was prepared based on Applicants’ proprietary formulations for assessing the effectiveness of sulfide compounds in plug-in diffusers. The plugin diffuser contained vanilla-based fragrances, which displayed floral and warm vanilla sugar notes.

Preparation of Test Samples: The fragrance only containing plug-in diffuser was used as the control sample. Mixture 1 obtained above was added to the fragrance in the plug-in diffusers to provide test samples with final concentrations of sulfide compounds at 0.001, 1 and 10 ppm, respectively.

Testing Procedure: Test was conducted in a smelling booth. Each sample was plugged in the smelling booth for 15 minutes prior to the sensory evaluation. The temperature of the plug-in diffuser reached about 60-80 °C. The control and test samples were presented in a blind and random order to a group of internal panelists.

Results and Discussion: The odor profiles and averaged scores are reported in the following:

Mixture 1 provided fragrance enhancement in plug-in diffusers at 1 and 10 ppm.

Example V: Fragrance Enhancement in Fabric Conditioners

Modeling Fabric Conditioners: A fabric conditioner was prepared based on Applicants’ proprietary formulations for assessing the effectiveness of sulfide compounds in fabric conditioners. The fabric conditioner contained vanilla-based fragrances, which displayed vanilla, sweet, jasmine, apple, pear, musk and wood notes.

Preparation of Test Samples: The fragrance only containing fabric conditioner was used as the control sample. Mixture 1 obtained above was added to the fragrance in the fabric conditioner to provide test samples with final concentrations of sulfide compounds at 0.001, 1 and 10 ppm, respectively.

Testing Procedure: Each sample was washed with 86/14 cotton/polyester blend face cloth and then dried with a regular cycle for 40 minutes. The temperature of the face cloth reached about 40-80 °C. The control and test samples were presented on trays in a blind and random order to a group of internal panelists.

Results and Discussion: The odor profiles and averaged scores are reported in the following:

Mixture 1 provided provided fragrance enhancement in fabric conditioners at 1 and 10 ppm.