Improved long-lasting fragrance

Abstract

The present invention relates to a fragrance having a long-lasting fragrance performance, a consumer product and its use based on at least one fragrance carrier selected based on the Hansen Solubility Parameters and a perfume raw material having medium and / or high volatility.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of priority to European Application No. 21201805.5, filed October 11, 2021, U.S. Provisional Application No. 63 / 253,723, filed October 8, 2021, and U.S. Provisional Application No. 63 / 242,366, filed September 9, 2021, the entire contents of which are expressly incorporated herein by this reference.

[0002] FIELD OF THEINVENTION The present invention relates to the field of fragrances, more particularly to fragrances with improved long-lasting performance.

[0003] background Longevity has long been a desired goal in the fragrance industry. Fragrance longevity and tenacity are key components of fragrance performance and are a desired consumer benefit in applications such as fine fragrances and antiperspirants / deodorants. This attribute has typically been pursued using pyramidal fragrance constructions that select large amounts of low volatility odorants (base notes), intermediate amounts of medium volatility odorants (middle notes), and minimum amounts of high volatility odorants (top notes).

[0004] Summary of the Invention The present invention uniquely combines the selection of a fragrance preservative based on the Hansen Solubility Parameter (HSP) with a fragrance ingredient having a middle note and / or a top note to identify a fragrance preservative with superior performance, which improves the longevity, linearity, and freshness sustainability of the fragrance.

[0005] The present invention encompasses the selection of fragrance carriers based on HSP values ​​for leave-on products such as, for example, eau de toilette, eau de parfum, body sprays, deodorants, antiperspirants, and air care products.

[0006] Fragrances according to the invention may include: (a) at least one fragrance component selected from the group consisting of a fragrance component having a top note, a fragrance component having a middle note, and combinations thereof; and (b) at least one flavoring agent having: i. In a solution with a compound that has a vapor pressure of more than 0.08 Torr at 22°C, the atomic dispersion force (δ d ), dipole moments 1-7 (δ p ), and hydrogen bonds (δ h At least two Hansen solubility parameters selected from the first group consisting of: ii. In a solution with a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C, the atomic dispersion force (δ d ), dipole moments 1-8 (δ p ), and 4–11 hydrogen bonds (δ h At least two Hansen solubility parameters selected from the second group consisting of:

[0007] The fragrance may further comprise alcohol and water.

[0008] In one embodiment of the present invention, group (i) has an atomic dispersion force (δ d ), dipole moment (δ p ), and hydrogen bonds (δ h Group (ii) can be selected from the group consisting of an atomic dispersion force (δ) of 16.86±2.72; d ), dipole moment (δ p ), and hydrogen bonds (δ h ).

[0009] The odorant according to the present invention may be, for example, octan-1-ol, octan-2-ol, 2-butyloctan-1-ol, 11-methyldodecan-1-ol, 2-hexyldodecan-1-ol, 14-methylpentadecan-1-ol, 16-methylheptadecan-1-ol, 2-octyldodecan-1-ol, 2-octyldodecan-1-ol, 2-decyltetradecan-1-ol, 2-dodecylhexadecan-1-ol, 2-tetradecyloctadecane-1-ol, [3-(2-ethylhexanoyloxy)-2,2-dimethylpropyl]2-ethylhexanoate, 3-tetradecoxypropan-1-ol, or a combination thereof.

[0010] The fragrance preservative according to the present invention can be little or no fragrance.

[0011] In one aspect of the invention, the preservative comprises 0.1% or more by weight of the fragrance.

[0012] In a further embodiment, the flavoring agent is present in a ratio of at least 1 / 10 relative to the at least one fragrance ingredient. The flavoring agent can also be present in a ratio of at least 1 / 4 relative to the at least one fragrance ingredient.

[0013] In embodiments of the present invention, the odorant has formula (I): CH3-(CH2) x -CHZ-(CH2) y -(CH3) (I) where: Z is a CH2OH, CHO, CO2H, CH2NH2 or CH2SH group; x is an integer from 3 to 15; y is an integer from 3 to 15; However, |xy| is less than 8.

[0014] The fragrance preservative according to the present invention may be a pro-fragrance.

[0015] The present invention includes consumer products that contain the fragrances of the present invention. [Brief description of the drawings]

[0016] [Figure 1] FIG. 1 shows an illustration of the Hansen space subtended in three directions by the interactions (D, P and H), where R0 is the radius of the solute's characteristic melt sphere. [Diagram 2] FIG. 1 shows the total area sum at 1 hour evaporation for different levels of PPG-20 methyl glucose ether (EDT B) and different levels of isocetyl alcohol (EDT C). [Diagram 3] FIG. 1 shows the total area sum over 2 hours of evaporation for different levels of PPG-20 methyl glucose ether (EDT B) and different levels of isocetyl alcohol (EDT C). [Figure 4] FIG. 1 shows the total area sum over 4 hours of evaporation for different levels of PPG-20 methyl glucose ether (EDT B) and different levels of isocetyl alcohol (EDT C). [Diagram 5] FIG. 1 shows direct injection data for each compound during 2-hour evaporation of RAHT1 alone (EDT A), RAHT1 in 5% PPG-20 methyl glucose ether (EDT B), and RAHT1 in 5% isocetyl alcohol (EDT C). [Figure 6] FIG. 1 shows the sum of fragrance areas after 4 hours of evaporation for EDT D (professional fragrance 1), EDT E (professional fragrance 2) and EDT F (professional fragrance 3) and the control EDT A. [Figure 7] FIG. 1 shows the total area sum throughout evaporation for RAHT2 alone (EDT1 RAHT2), RAHT2 with 5% hexyldecanol (EDT2 RAHT2), and RAHT2 with 5% octyldodecanol (EDT3 RAHT2). [Figure 8]FIG. 1 shows direct injection data for each compound during 2-hour evaporation of RAHT2 alone (EDT1 RAHT2), RAHT2 in 5% hexyldecanol (EDT2 RAHT2), and RAHT2 in 5% octyldodecanol (EDT3 RAHT2). [Figure 9] FIG. 1 shows direct injection data for each compound during 4-hour evaporation of RAHT2 alone (EDT1 RAHT2), RAHT2 in 5% hexyldecanol (EDT2 RAHT2), and RAHT2 in 5% octyldodecanol (EDT3 RAHT2). [Figure 10] FIG. 1 shows direct injection data for each compound during 6-hour evaporation of RAHT2 alone (EDT1 RAHT2), RAHT2 in 5% hexyldecanol (EDT2 RAHT2), and RAHT2 in 5% octyldodecanol (EDT3 RAHT2). [Figure 11] FIG. 1 shows that fragrances containing hexyldecanol (Jarcol I-16 N) were perceived as more intense after 2 and 4 hours of drydown compared to fragrances containing isocetyl alcohol (ICA).

[0017] Detailed Description An "odor retainer" or "modulator" according to the present invention is a material that adjusts the vapor pressure of a fragrance ingredient and retards the evaporation profile of the fragrance ingredient. The odor retainer or modulator may be unscented or may be a pro-fragrance with odor retaining properties.

[0018] A "pro-perfume" or "pro-fragrance" is a compound that, under an external influence, can release one, two or more fragrant ingredients, also called PRMs (perfume raw materials), so as to prolong the fragrance effect of the PRM. In the present invention, the terms "pro-perfume" or "pro-fragrance" are used interchangeably. The perfume raw materials can be released from the pro-perfume compound by one or more mechanisms. For example, the perfume raw materials can be released from the pro-perfume compound by (chemical) cleavage of the pro-perfume compound. The external influence that leads to the cleavage of the pro-perfume compound can be light. By "light" we mean any form of electromagnetic radiation, not limited to a specific wavelength. The release of PRMs from such pro-perfume compounds is usually more effective at lower wavelengths (higher energy input). The cleavage of certain pro-perfume compounds can also be induced by air / oxygen. The PRMs can then be released from the pro-perfume compound by oxidation in the presence of air (ambient air) or oxygen. Furthermore, PRMs can be released from certain proparfume compounds by heat. By "heat" we mean any energy input resulting from an increase in temperature. Furthermore, PRMs can be released from certain proparfume compounds by moisture. Such proparfume compounds may exhibit chemical bonds that are susceptible to cleavage by water and therefore are cleavable in the presence of water. In some cases, a certain pH value may induce and / or support the cleavage. Furthermore, PRMs can be released from certain proparfume compounds upon exposure to enzymes. Such proparfume compounds may exhibit chemical bonds that can be efficiently cleaved in the presence of enzymes. In some cases, PRMs can be released from certain proparfume compounds based not only on one type of release mechanism but also on two or more of the above-mentioned release mechanisms simultaneously, for example release by air / oxygen and moisture. Typically, the proparfume itself has low volatility and ideally has (almost) no scent. Properfume may advantageously be characterized by a vapor pressure of less than 0.01 Pa, as calculated using EPIwin v. 3.10 software (2000, available from the United States Environmental Protection Agency). According to one embodiment:The vapor pressure is less than 0.001 Pa. Properfumes may also advantageously be characterized by a molecular weight of more than 270, or even more than 300, or even more than 350. The terms "properfume" or "profragrance" have their usual meaning in the art, as reported, for example, in A. Herrmann, Angew. Chem. Int. Ed., 2007, 46, 5836-5863. Profragrances may be in the form of α-ketoesters, α-ketoacids, enol ethers, Knoevenagel adducts, Michael adducts, esters, α,β-unsaturated esters, diesters, siloxanes, imines, cinnamyl ethers, heterocyclic compounds such as aminals, imidazolidinones or oxazolidines, non-limiting examples of suitable properfumes include 4-(dodecylthio)-4-(2,6,6-trimethyl- 2-Cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 3-(dodecylsulfonyl)-1-(2,6,6-trimethylcyclohexen-3-en-1-yl)butan-1-one, (3-mercaptopropyl )(methyl)dimethoxysilane linear polysiloxane copolymer, 2-(dodecylthio)octan-4-one, 2-(dodecylsulfonyl)octan-4-one, 4-oxooctane-2-yl dodecanoate, 2-phenylethyloxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-1-yloxo(phenyl)acetate, (Z)-hex-3-en-1-yloxo(phenyl)acetate, 3,7- Dimethyl-2,6-octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl)succinate, (2E,6Z)-2,6-nonadienyl hexadecanoate, (2E,6Z)-2,6-nonadien-1-yl tetradecanoate, (2E,6Z)-2,6-nonadien-1-yl dodecanoate, (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene,1-Methoxy-4-(3-methyl-4-phenethoxybut-3-en-1-yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3-yloxy)undec-1-ene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1 -Phenethoxyprop-1-en-2-yl)benzene, 2-(1-phenethoxyprop-1-en-2-yl)naphthalene, (2-phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2-phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl )benzene, 1-methoxy-4-(1-phenethoxyprop-1-en-2-yl)benzene, (2-((2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(2-methyl-3-phenethoxyallyl)benzene, (2-((2-isopropyl-5-methylcyclohexylidene)methoxy)ethyl)benzene, 1-isopropyl-4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methyl Examples of suitable fragrances include 2-ethoxy-1-((2-pentylcyclopentylidene)methoxy)-4-propylbenzene, 2-ethoxy-1-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 3-methoxy-4-((2-methoxy-2-phenylvinyl)oxy)benzaldehyde, 1-isopropyl-2-((2-methoxy-2-phenylvinyl)oxy)-4-methylbenzene, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde, or mixtures thereof. In particular, the fragrances having fragrance retention properties areIt may be 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, trans-3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone or (2-((2-methylundec-1-en-1-yl)oxy)ethyl)benzene.

[0019] The preservatives according to the present invention comprise materials selected on the basis of their solubility parameters believed to allow gentle interaction with volatile perfume raw materials (PRMs). The preservatives' odor contribution is low to unscented so as to minimize the olfactory impact on fragrance mixtures in which they are included.

[0020] In an embodiment of the invention, the formulation according to the invention comprises: [Table 1]

[0021] In another embodiment, the formulation according to the invention comprises: [Table 2]

[0022] a. Hansen solubility parameters The preservative according to the present invention has an HSP that optimizes the affinity to top and middle notes. HSP is a physicochemical parameter used to estimate the type of interaction force that causes compatibility between substances. A complete description of HSP and its application to fragrance design is described in WO2020 / 234154, which is incorporated herein by reference in its entirety.

[0023] The basis of HSP is that the cohesive energy (E) is proportional to the atomic dispersion (E d ), dipole-dipole intermolecular interactions (E p ) and hydrogen bond interactions (Eh ) corresponding to the different types of intermolecular interactions mentioned above. Similarly, the total solubility parameter is divided into three parts, namely, the dispersion (δ d ), polarity (δ p ) and hydrogen bonds (δ h ) can be divided into

[0024] The Hansen solubility parameters are as follows: 1. Atomic dispersion force δ d The dispersion term of HSP is thought to be based on dispersion energy. Even in systems that do not have heteroatoms such as oxygen or nitrogen, charge distributions can occur due to the transfer of electrons. The electric fields generated by these charge distributions create dispersion attractive forces between molecules.

[0025] The van der Waals and refractive index based parameters are used to define whether a molecule of interest is aliphatic, alicyclic, or aromatic and are calculated according to the method described in Blanks and Prausnitz. The dispersion parameters are atomic based and are primarily determined by the critical temperature T c This critical temperature T c can be estimated using the Lydersen group contributions.

[0026] 2. Polar solubility parameter (dipole moment) δ p The polar solubility parameter is based on permanent dipole-permanent dipole interactions. It is based on the equation developed by Hansen and Beerbower: δ p =37.4(DM) / V 1 / 2 where DM is the dipole moment of the molecule and V is the molar volume.

[0027] 3. Hydrogen bond δ h Hydrogen bonding can be considered as a special type of dipole-dipole interaction that occurs between polar molecules, where a hydrogen atom bonded to one electronegative atom is attracted to another electronegative atom in another polar molecule, such as nitrogen or oxygen. Due to the large difference in electronegativity between hydrogen and electronegative elements, hydrogen bonding is the strongest intermolecular interaction.

[0028] Group contribution methods (GSMs) can be used to theoretically estimate solubility parameters. The method is based on the assumption that each functional group of a molecule contributes to the overall thermodynamic properties in addition to being additive. As shown in the following equation, the three Hansen components can be estimated by the method of Hoftyzer and van Krevelen:

number

[0029] Here, F d is the dispersibility functionality, F p is the polar functional group value, and E h is the hydrogen bonding functionality and V is the molar volume.

[0030] The selection of the ideal carrier is based on Hansen's dissolving sphere.

[0031] Based on the idea of ​​interaction energy additivity, Hansen proposed that the cohesive energy can be expressed as the sum of three components corresponding to three different types of interactions: atomic dispersion forces (D), permanent dipole-permanent dipole intermolecular interactions (P), and electron exchange hydrogen bond interactions (H). Hansen therefore decomposed the Hildebrand solubility parameter into three components according to the following equation:

[0032]

number

[0033] Figure 1 shows an illustration of the Hansen space defined in three directions by the interactions (D, P and H), where R0 is the radius of the solute's characteristic solubility sphere and Ra is the distance between the solute's solubility parameter (center of the solubility sphere) and the solvent's solubility parameter.

[0034] For fragrance mixtures, the simplest way to calculate the HSP of the mixture is to assume an ideal mixture of each compound:

number

[0035] Where:

number

[0036] HSP can be calculated accurately using software called "HSPiP". The ratio RED (Relative Energy Difference) is defined as follows:

number

[0037] The RED value is used as a measure of the affinity of one compound with another.

[0038] If RED<1, the selected flavoring has a "good" affinity for the other PRMs. The affinity limit is reached when RED=1.

[0039] · RED>1 flavorants are considered to have no affinity for the PRM.

[0040] The present invention encompasses the use of an unscented preservative in a hydroalcoholic solution of perfume. The preservative is present in a concentration of 0.1% or more by weight of the perfume solution and has an affinity for top and middle notes based on HSP values. The preservative has a ratio of at least 1 / 10, or preferably at least 1 / 4, to the fragrance loading.

[0041] According to the present invention, the volatility of PRMS is based on the absolute vapor pressure expressed in Torr. Therefore, the top and middle notes are defined accordingly: [Table 3]

[0042] Thus, in certain embodiments, the flavoring agent is selected as follows: i. The odorant is present in a final consumer product containing 0.5%-95% fragrance containing odorant molecules at a loading level of 0.05% or more, 1% or more, or 3% or more. The ratio of odorant loading to fragrance loading may be 1:4.

[0043] ii. The solubility parameters can be targeted to top and middle notes based on the ranges set out below: The preservative has at least two of the three Hansen Solubility Parameters for each class defined as top and middle notes.

[0044] [Table 4]

[0045] In one embodiment, the at least one flavoring agent comprises a compound having: i. In a solution with a compound that has a vapor pressure of more than 0.08 Torr at 22°C, the atomic dispersion force (δ d ), dipole moments 1-7 (δ p ), and hydrogen bonds (δ h) at least two HSPs selected from the group consisting of: ii. In a solution with a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C, the atomic dispersion force (δ d ), dipole moments 1-8 (δ p ), and 4–11 hydrogen bonds (δ h ).

[0046] In one embodiment, group (i) has an atomic dispersion force (δ d ), dipole moment (δ p ), and hydrogen bonds (δ h ).

[0047] In a further embodiment, group (ii) has an atomic dispersion force (δ) of 16.86±2.72. d ), dipole moment (δ p ), and hydrogen bonds (δ h ).

[0048] The at least one modulator may, for example, be selected from the compounds listed in the table below.

[0049] [Table 5]

[0050] In some embodiments of the present invention, the odorant is an aliphatic alcohol and the alcohol functionality is a non-terminal functionality. For example, the alcohol functionality may occur at least 2, at least 3, or at least 4 carbons from the terminal carbon. One example of such an odorant is 2-hexyldecan-1-ol: [ka] It is.

[0051] The fatty alcohols according to the present invention may be linear or branched. The longest chain in the fatty alcohol is at least 5 carbons long. The fatty alcohol may be, for example, up to 32 carbons long.

[0052] Surprisingly, the fragrance preservatives according to the invention, which have an alcohol moiety in the middle of the carbon chain, perform better than similar molecules with terminal alcohol functionality. Known fragrance preservatives that do not have an HSP value of 2-3 within the above range have been found to be less effective than the fragrance preservatives of the invention.

[0053] According to the present invention, a professional fragrance can be a fragrance preservative by satisfying the HSP criteria. A professional fragrance can also be used in combination with a fragrance preservative of the present invention. A professional fragrance can extend the freshness of a fragrance by releasing its fragrant compounds upon application and / or can act as a fragrance preservative before the release of the fragrant ingredients.

[0054] B. Aroma components As used herein, "fragrance ingredient" or "perfume raw material" refers to a compound for use in perfumery that is used for its ability to emit a pleasant odor and to impart a hedonic effect or a pleasant odor, either by itself or in admixture with other such ingredients, to the product into which it is incorporated or to the surface to which it is applied, such as the skin or hair. A fragrance ingredient has the ability to impart or modify the odor of a composition or surface in a positive or pleasant way. If the composition or surface has a malodor, the fragrance ingredient can also mask such a malodor so as to make the overall odor perceived pleasant.

[0055] "Odorable ingredients" or "perfume raw materials" can include any perfume raw materials suitable for fragrance applications, including materials such as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogen- or sulfur-containing heterocyclic compounds, and essential oils. Also included are oils and exudates of natural origin, animal and vegetable origin, which contain complex mixtures of various chemical components. Individual perfume raw materials, including known natural oils, can be found by consulting journals commonly used by those skilled in the art, such as "Perfume and Flavourist" or "Journal of Essential Oil Research", or are listed in reference books such as Perfume and Flavor Chemicals, 1969, by S. Arctander, Montclair, New Jersey, USA, and recently republished by Allured Publishing Corporation Illinois (1994). In addition, some perfume raw materials are supplied as mixtures by fragrance houses in the form of their own special accords. EXAMPLES

[0056] [Example 1 - Comparison of a preservative that meets three HSP criteria with a preservative that meets one HSP criterion] Jarcol I16N (hexyldecanol) (Jarchem) meets three of the HSP criteria of the present invention. Glucam P20 (PPG-20 methyl glucose ether) (Lubricol) meets one HSP parameter within the HSP range of the present invention (see table below).

[0057] [Table 6]

[0058] (EDT A - Reference) A reference EDT formulation (EDT A) was prepared and used as a control to evaluate the fragrance performance. Water was added to ethanol. After stirring, fragrance was added to this solution. The final mixture was stirred until homogenous.

[0059] [Table 7]

[0060] (EDT B containing PPG-20 methyl glucose ether) PPG-20 Methyl Glucose Ether (MGE) was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0061] [Table 8]

[0062] * The test concentrations of ICA were varied as follows: 0.5%, 2%, 5% and 10%, and the amount of 96° ethanol was adjusted as follows: 79.5%, 78%, 75% and 70%, respectively.

[0063] (EDT C containing isocetyl alcohol) Isocetyl alcohol (ICA) was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0064] [Table 9]

[0065] * The test concentrations of MGE were varied as follows: 0.5%, 2%, 5% and 10%, and the amount of 96° ethanol was adjusted as follows: 79.5%, 78%, 75% and 70%, respectively.

[0066] Research Accord HT1 (RAHT1) used in Experiments 1 and 1B consisted of equal concentrations of the highly to less volatile components shown in Table 10A.

[0067] [Table 10-1]

[0068] [Table 10-2]

[0069] Evaporation was performed with a Tzero lid. A Prazitherm PZ72 slide warmer was preheated to 32°C for 30 minutes. Each crucible was placed on a precision hot plate. Using an adjustable volume pipette, 10 μL of fragrance was added directly to the center of the crucible and evaporated on the precision hot plate for 5 minutes (considered as time zero), 30 minutes, 1 hour, 2 hours, 4 hours, and 6 hours at 32°C. A set of duplicate replicates was performed for each sample and each test condition. Once each time point was reached, each crucible was placed in a 2 mL Agilent GC vial (Agilent 5183-2068) and evaporation was stopped by adding 600 μL of ethanol. The vial was closed and shaken to mix for at least 1 minute. Samples were analyzed by GC-MS direct injection.

[0070] Figures 2-4 show the total area sums for 1 hour, 2 hours, and 4 hours of evaporation for different levels of PPG-20 methyl glucose ether (EDT B) and different levels of isocetyl alcohol (EDT C).

[0071] The data show that total retention of all compounds was greater with isocetyl alcohol (EDT C) at all levels throughout evaporation than with PPG-20 methyl glucose ether (EDT B) at all levels except 0.5%, which showed the opposite effect during the 4-h evaporation.

[0072] FIG. 5 shows the direct injection data for each compound during the 2-hour evaporation of RAHT1 alone (EDT A), RAHT1 in 5% PPG-20 methyl glucose ether (EDT B), and RAHT1 in 5% isocetyl alcohol (EDT C).

[0073] The data show that retention of all compounds was higher with 5% isocetyl alcohol (EDT C) than with the control at 2 h evaporation. The same results were observed with PPG-20 methyl glucose ether (EDT B), but to a lesser extent.

[0074] Example 1B - Pro-fragrances that meet two of the HSP criteria have aroma retention properties.

[0075] Pro-Fragrances 1 to 3 meet two of the HSP criteria of the present invention.

[0076] [Table 11]

[0077] (EDT D containing Pro Fragrance 1) Pro-Fragrance 1 was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0078] [Table 12]

[0079] (EDT E containing Pro Fragrance 2) Pro-Fragrance 2 was mixed with ethanol and water. After stirring, the fragrance was added to the mixture. The final solution was stirred until homogenous.

[0080] [Table 13]

[0081] (EDT F with Pro Fragrance 3) Pro-Fragrance 3 was mixed with ethanol and water. After stirring, the fragrance was added to the mixture. The final solution was stirred until homogenous.

[0082] [Table 14]

[0083] Evaporation was performed with a Tzero lid. A Prazitherm PZ72 slide warmer was preheated to 32°C for 30 minutes. Each crucible was placed on a precision hot plate. Using an adjustable volume pipette, 10 μL of fragrance was added directly to the center of the crucible and evaporated on the precision hot plate for 5 minutes (considered as time zero), 30 minutes, 1 hour, 2 hours, 4 hours, and 6 hours at 32°C. A set of duplicate replicates was performed for each sample and each test condition. Once each time point was reached, each crucible was placed in a 2 mL Agilent GC vial (Agilent 5183-2068) and evaporation was stopped by adding 600 μL of ethanol. The vial was closed and shaken to mix for at least 1 minute. Samples were analyzed by GC-MS direct injection.

[0084] FIG. 6 shows the sum of fragrance areas after 4 hours of evaporation for EDT D (Pro-fragrance 1), EDT E (Pro-fragrance 2) and EDT F (Pro-fragrance 3) and the control EDT A.

[0085] The data show that EDT D (Pro-Fragrance 1), EDT E (Pro-Fragrance 2) and EDT F (Pro-Fragrance 3) have greater fragrance retention than the control EDT A after 4 hours of evaporation.

[0086] Example 2 - Preservatives with non-terminal alcohol functionality are efficient preservatives

[0087] (EDT1 - Reference) A reference EDT formulation was prepared and used as a control to evaluate the fragrance performance. Water was added to ethanol. After stirring, fragrance was added to this solution. The final mixture was stirred until homogenous.

[0088] [Table 15]

[0089] (EDT2 containing hexyldecanol) Hexyldecanol was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0090] [Table 16]

[0091] (EDT3 containing octyldodecanol) Octyldodecanol was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0092] [Table 17]

[0093] Evaporative GC-MS kinetics The following evaporation kinetics study was performed: The Research Accord HT2 (RAHT2) used in this study consisted of equal concentrations of high to low volatility components.

[0094] [Table 18-1]

[0095] [Table 18-2]

[0096] RAHT2 was solubilized with EDT1, EDT2, and EDT3.

[0097] Evaporation was performed with a Tzero lid. A Prazitherm PZ72 slide warmer was preheated to 32°C for 30 minutes. Each crucible was placed on a precision hot plate. Using an adjustable volume pipette, 10 μL of fragrance was added directly to the center of the crucible and evaporated on the precision hot plate for 5 minutes (considered as time zero), 30 minutes, 1 hour, 2 hours, 4 hours, and 6 hours at 32°C. A set of duplicate replicates was performed for each sample and each test condition. Once each time point was reached, each crucible was placed in a 2 mL Agilent GC vial (Agilent 5183-2068) and evaporation was stopped by adding 600 μL of ethanol. The vial was closed and shaken to mix for at least 1 minute. Samples were analyzed by GC-MS direct injection.

[0098] FIG. 7 shows the total area sum throughout evaporation for RAHT2 alone (EDT1 RAHT2), RAHT2 with 5% hexyldecanol (EDT2 RAHT2), and RAHT2 with 5% octyldodecanol (EDT3 RAHT2).

[0099] The data show that the total retention of all compounds was higher with 5% hexyldecanol (EDT2) than with the control throughout evaporation, and the same results were observed with 5% octyldodecanol (EDT3).

[0100] Figures 8 to 10 show the direct injection data for each compound after 2-hour, 4-hour, and 6-hour evaporation of RAHT2 alone (EDT1 RAHT2), 5% hexyldecanol containing RAHT2 (EDT2 RAHT2), and 5% octyldodecanol containing RAHT2 (EDT3 RAHT2).

[0101] The data show high retention of all compounds, most notably the medium and low volatility notes.

[0102] [Sensory evaluation] A sensory evaluation of the overall strength of fragrance CF, which is composed of the following ingredients, was carried out.

[0103] [Table 19]

[0104] A Prazitherm PZ72 slide warmer was preheated to 32° C. for 30 min. The glass plate was placed on a precision hot plate. Using an adjustable volume pipette, 20 μL of EDT was added directly to the center of the glass plate and allowed to evaporate at 32° C. Seven panelists evaluated randomized glass plates at different times (t=0 min (fresh), 2 h, 4 h, and 6 h).

[0105] A three-arm forced choice (3-AFC) test was used. At each time point, panelists were presented with three samples, two of which were fragrance CF (EDT1) and one of which was a fragrance CF according to the invention (EDT2 or EDT3). Panelists indicated the sample that they perceived as stronger in terms of overall intensity.

[0106] hypothesis: - H0: There is no difference between the two samples. - H1: In terms of overall strength, samples with technology are stronger than samples without technology.

[0107] Associated risks: - H0 rejection = α risk: - The risk of false alarms resulting in concluding that the products are different when in fact they are not.

[0108] Data were analyzed using binomial statistics.

[0109] Interpretation of the data: - If a p-value is obtained with α ≤ 0.05, the overall strength of the samples with the technology is stronger than that of the samples without the technology; - If a p-value is obtained with 0.05<α≦0.10, it is judged that there is a trend difference. - If a p-value is obtained with α>0.10, the samples are not significantly different.

[0110] The results of the sensory panel, shown in the table below, show that the formulation according to the invention performs better in the presence of 5% hexyldecanol (EDT2) fresh and after 4 hours of evaporation, and in the presence of 5% octyldodecanol (EDT3) at all time points.

[0111] [Table 20]

[0112] Example 3: Hexyldecanol has more sustained sensory benefits than ICA.

[0113] (EDT2 containing hexyldecanol) Hexyldecanol was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0114] [Table 21]

[0115] (EDT4 containing isocetyl alcohol) Isocetyl alcohol was mixed with ethanol and water. After stirring, fragrance was added to the mixture. The final solution was stirred until homogenous.

[0116] [Table 22]

[0117] [Sensory evaluation] Fragrance CF was subjected to a sensory evaluation of overall strength.

[0118] A Prazitherm PZ72 slide warmer was preheated to 32° C. for 30 min. The glass plate was placed on a precision hot plate. Using an adjustable volume pipette, 20 μL of EDT was added directly to the center of the glass plate and allowed to evaporate at 32° C. Seven panelists evaluated randomized glass plates at different times (t=0 min (fresh), 2 h, 4 h, and 6 h).

[0119] A three-way forced choice (3-AFC) test was used. At each time point, panelists were presented with three samples, two of which were fragrance CF (EDT3) and one of which was fragrance CF according to the invention (EDT2). Panelists indicated the sample that they perceived as stronger in terms of overall intensity.

[0120] hypothesis: - H0: There is no difference between the two samples. - H1: In terms of overall strength, samples with technology are stronger than samples without technology.

[0121] Associated risks: - H0 rejection = α risk: - The risk of false alarms resulting in concluding that the products are different when in fact they are not.

[0122] Data were analyzed using binomial statistics.

[0123] Interpretation of the data: - If a p-value is obtained with α ≤ 0.05, the overall strength of the samples with the technology is stronger than that of the samples without the technology; - If a p-value is obtained with 0.05<α≦0.10, it is judged that there is a trend difference. - If a p-value is obtained with α>0.10, the samples are not significantly different.

[0124] The results of the sensory panel data below show that in the presence of 5% hexyldecanol (EDT2), the formulation according to the invention performs better after 2 and 4 hours of evaporation.

[0125] [Table 23]

[0126] FIG. 11 shows that the fragrance containing hexylsecanol was perceived as more intense after 2 and 4 hours of drydown compared to the fragrance using ICA.

Claims

1. (a) at least one fragrance component selected from the group consisting of a fragrance component having a top note, a fragrance component having a middle note, and combinations thereof; and (b) at least one flavoring agent having: i. In solution with a compound that has a vapor pressure greater than 0.08 Torr at 22°C, the atomic dispersion force (δ ｄ ), dipole moments (δ ｐ ), and 2.5-11 hydrogen bonds (δ ｈ at least two Hansen solubility parameters selected from the first group consisting of: ii. In solution with compounds having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C, atomic dispersion forces (δ ｄ ), 1-8 dipole moments (δ ｐ ), and 4 to 11 hydrogen bonds (δ ｈ At least two Hansen solubility parameters selected from the second group consisting of Including fragrance.

2. Group (i) has an atomic dispersion force (δ ｄ ), dipole moment (δ) of 4.15±2.65 ｐ ), and 6.72 ± 4.11 hydrogen bonds (δ ｈ ), wherein group (ii) is selected from the group consisting of an atomic dispersion force (δ ｄ ), dipole moment (δ) of 4.61 ± 3.10 ｐ ), and 7.66 ± 3.29 hydrogen bonds (δ ｈ 2. The fragrance of claim 1, wherein the aromatic compound is selected from the group consisting of:

3. 2. The fragrance of claim 1, wherein the at least one carrier is selected from the group consisting of octan-1-ol, octan-2-ol, 2-butyloctan-1-ol, 11-methyldodecan-1-ol, 2-hexyldodecan-1-ol, 14-methylpentadecan-1-ol, 16-methylheptadecan-1-ol, 2-octyldecan-1-ol, 2-octyldodecane-1-ol, 2-decyltetradecan-1-ol, 2-dodecylhexadecan-1-ol, 2-tetradecyloctadecane-1-ol, [3-(2-ethylhexanoyloxy)-2,2-dimethylpropyl]2-ethylhexanoate, 3-tetradecoxypropan-1-ol, and combinations thereof.

4. 2. The fragrance of claim 1, wherein the preservative is unscented.

5. 10. The fragrance of claim 1, further comprising a volatile solvent and water.

6. 2. The fragrance of claim 1, wherein said preservative comprises 0.1% or more by weight of said fragrance.

7. 2. The fragrance of claim 1, wherein said preservative is present in a ratio of at least 1 / 10 relative to said at least one fragrant ingredient.

8. 8. The fragrance of claim 7, wherein said preservative is present in a ratio of at least 1 / 4 relative to said at least one fragrant ingredient.

9. The flavoring agent is a compound represented by formula (I): CH ３ -(CH ２ ) ｘ -CHZ-(CH ２ ) ｙ -(CH ３ ) (I) where: Z is CH ２ OH, CHO, CO ２ H, CH ２ NH ２ or CH ２ is an SH group; x is an integer from 3 to 15; y is an integer from 3 to 15; The fragrance according to claim 1, wherein |x-y| is less than 8.

10. 2. The fragrance of claim 1, wherein said preservative is a professed fragrance.

11. A consumer product comprising a fragrance according to any one of claims 1 to 10.

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