Formulated to provide long-lasting fragrance performance

Abstract

The present invention provides long-lasting fragrance compositions that impart to consumers a lasting perception and / or intensity of fragrance during the period of fragrance wear. The present invention provides long-lasting fragrance compositions for extending the performance of fragrance oils.

Description

Technical Field

[0001] The present invention relates to compositions and methods for providing long-lasting fragrance (scent / fragrance) performance. Background Art

[0002] Maintaining fragrance intensity and / or profile over time is an important consideration for commercial fragrance compositions. In the perfumery industry, there is a constant need to find new ways to extend the intensity and perception of fragrance over time. For example, it is generally accepted that fragrance compositions should maintain intensity and / or fragrance profile for at least 8 hours to meet consumer needs.

[0003] Therefore, it is desirable to have a fragrance composition that retains a significant portion of its initial fragrance characteristics over time. It is also desirable to have a fragrance composition whose fragrance intensity remains noticeable to consumers over a long period of time. Summary of the invention

[0004] The formulations according to the present invention impart to the consumer a lasting perception and / or intensity of the fragrance and an acceptable skin feel during the fragrance wear period.The present invention provides long-lasting fragrance compositions, methods and uses for extending the performance of fragrance oils.

[0005] A long-lasting fragrance composition according to the present invention comprises oil; a gelling agent, wherein the gelling agent accounts for 0.01 to 15% w / w of the long-lasting fragrance composition; a volatile solvent; and water. In certain forms, the gelling agent accounts for 0.3 to 0.6% w / w of the long-lasting fragrance composition.

[0006] The gelling agent of the present invention can be selected from the group consisting of: n-alkanes with more than 16 CH2 chains, hydroxyalkanoic acids, hydroxy-octadecanoyl, hydroxy-hexadecanoyl, dihydroxyalkanoic acids, dicarboxylic acids, fatty acid alkyl esters with an alkyl chain length of more than 20 CH2 groups, hydroxyalkanols, glycyrrhizic acid, anthracene derivatives, dendrimers n-alkanes, oligo(p-phenylene vinylene), dipyridyl urea-carboxylic acid combinations, diamine-linked dendrons, dibutyl ethylhexanoyl glutamide, dibutyl lauroyl monoglycerol, dibutyl lauroyl 2-glycerol, dibutyl lauroyl glycerate, dibutyl lauroyl glycerol ether, dibutyl lauroyl monoethanolamide, dibutyl lauroyl diethanolamide, dibutyl lauroyl glutamine, organic gelling agents, amino acid-based gelling agents, hydroxy fatty acid gelling agents, ester gums, hydroxypropyl cellulose and combinations thereof.

[0007] In some forms of the present invention, the long-lasting fragrance composition comprises a fragrance oil, a gelling agent, and an amphiphilic oil-soluble compound. The amphiphilic oil-soluble compound may account for 0.01% to 40% w / w of the long-lasting fragrance composition. In other forms, the amphiphilic oil-soluble compound accounts for 0.5% to 30% w / w of the long-lasting fragrance composition.

[0008] The amphiphilic oil-soluble compounds of the present invention include compounds having one of the following chemical structures:

[0009] or

[0010] wherein n represents the number of CH2 groups and is greater than 14, m represents the number of unsaturated CC bonds and is greater than or equal to 1, and Ri is selected from the group consisting of:

[0011]

[0012]

[0013]

[0014] Serinolamide, methylpropylene glycolamide, ethylpropylene glycolamide, urea, ureaol, biuret, biuretol, anandamine, glycerol ethers, glycolipids, and combinations thereof.

[0015] In certain forms, the amphiphilic oil-soluble compound is glyceryl monooleate or phytantriol or a combination thereof.

[0016] The long-lasting fragrance composition of the present invention may comprise 0.01% to 40% w / w of an amphiphilic oil-soluble compound, a volatile solvent and water. The amphiphilic oil-soluble compound may account for 0.5 to 10% w / w of the long-lasting fragrance composition.

[0017] Fragrance oils may comprise from 0.01 to 70% w / w of the long-lasting fragrance composition.

[0018] The long-lasting fragrance composition according to the present invention may comprise fragrance oil, an amphiphilic oil-soluble compound accounting for 0.01% to 40% w / w of the long-lasting fragrance composition, a volatile solvent and water. In certain forms, the amphiphilic oil-soluble compound accounts for 0.5 to 10% w / w of the long-lasting fragrance composition.

[0019] In some aspects of the invention, water comprises 0.01 to 60% w / w of the long-lasting fragrance composition. In other aspects, water comprises 0.7 to 60% w / w of the long-lasting fragrance composition. In some aspects of the invention, the water content can be 0.1 to 60% w / w of the long-lasting fragrance composition; 0.7 to 50% w / w of the long-lasting fragrance composition; or 1% to 30% w / w of the long-lasting fragrance composition.

[0020] The volatile solvent may be, for example, ethanol, isopropanol, ether or a mixture thereof.

[0021] The long-lasting fragrance composition of the present invention may further include a regulator. In some forms of the present invention, the regulator can be selected from the group consisting of: methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol di(ethylhexanoate); sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether; polyglyceryl-4 ether; isoceteth-5; isoceteth-7, isoceteth- 10; isoceteth-12; isoceteth-15; isoceteth-20; isoceteth-25; isoceteth-30; disodium lauroamphodipropionate; hexaethylene glycol monododecyl ether; and mixtures thereof; neopentyl glycol diisononanoate; cetearyl ethylhexanoate; panthenol ethyl ether, DL-panthenol, hexadecyl nonanoate, hexadecyl nonanoate, nerolidol, polymethylol, profragrance, cyclodextrin, encapsulating agents, and combinations thereof.

[0022] In some forms, the modulator accounts for 0.5% to 20% w / w of the total weight of the long-lasting fragrance composition. In one form of the present invention, the modulator accounts for 1% w / w of the total weight of the long-lasting fragrance composition. In another form, the modulator accounts for 2% w / w of the total weight of the long-lasting fragrance composition. In another form, the modulator accounts for 3% w / w of the total weight of the long-lasting fragrance composition. In a further form, the modulator can account for 4% or 5% w / w of the total weight of the long-lasting fragrance composition.

[0023] In some aspects of the invention, the amphiphilic oil-soluble compound has one of the following chemical structures:

[0024] or

[0025] wherein n represents the number of CH2 groups and is greater than 14, m represents the number of unsaturated CC bonds and is greater than or equal to 1, and Ri is selected from the group consisting of:

[0026]

[0027]

[0028]

[0029] Serinolamide, methylpropylene glycol amide, ethylpropylene glycol amide, urea, urea alcohol, biuret, biuretol, N-arachidonic acid aminoethanol, glycerol ethers, glycolipids and combinations thereof.

[0030] In certain forms, the amphiphilic oil-soluble compound is monoolein or phytantriol or a combination thereof. In some embodiments, the amphiphilic oil-soluble compound accounts for 1% to 5% w / w of the total weight of the long-lasting fragrance composition. In another embodiment, the amphiphilic oil-soluble compound accounts for about 3% of the total weight of the long-lasting fragrance composition.

[0031] In some forms of the present invention, 40 to 100% of the fragrance oils in the long-lasting fragrance composition are volatile components, which contain at least one fragrance raw material with a vapor pressure greater than 0.0008 Torr at 22° C. In another form, the volatile component contains at least one fragrance raw material with a vapor pressure greater than 0.08 Torr.

[0032] The long-lasting fragrance composition may further comprise a second fragrance raw material having a vapor pressure greater than 0.08 Torr at 22°C.

[0033] In some forms, 0.08 to 85% of the fragrance oil in the long-lasting fragrance composition is a volatile component, which includes at least one fragrance raw material having a vapor pressure of 0.0008 to 0.08 Torr at 22° C. The long-lasting fragrance composition may also include a second fragrance raw material having a vapor pressure of 0.0008 to 0.08 Torr at 22° C.

[0034] The present invention includes a leave-on consumer product containing a volatile solvent, which comprises a long-lasting fragrance composition. The leave-on consumer product containing a volatile solvent can be a perfume (Parfum), a light perfume (Eau de Toilette), a light fragrance (Eau de parfum), an Eau de Cologne (Eau de Cologne), a moisturizing spray (Body mist), a body spray (bodyspray), a body smear perfume (Body splash), a hair mist (Hair mist), an air care spray (air carespray), a leave-on hair care product (Hair Leave products), a fabric refresher (Fabric refreshers) and a deodorant (Deodorant).

[0035] Leave-on consumer products containing volatile solvents may also contain dyes, UV filters, antioxidants, quenchers, chelators, solubilizers, moisturizers, humectants, anti-aging actives, soothing agents, emollients, anti-pollution actives, or combinations thereof. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 is a bar graph showing the relative intensity of the fragrance ingredient styryl acetate dissolved in the headspace of formulations EDT 1 to 4 at different evaporation times.

[0037] Figure 2 is a bar graph showing the relative intensity of the fragrance A component from formulation EDT2 (using gelling agent AGA) after 6 hours of evaporation.

[0038] Figure 3 is a bar graph showing the effect of compound concentration on aroma retention after evaporation at 32°C for 6 hours.

[0039] Figure 4 It is a bar graph showing the sensory panel comparison results of aroma SP in EDT without and with 3% GMO, aroma SP in EDT without and with 5% ICA, and aroma SP in EDT without and with 3% GMO + 5% ICA. There was no difference with 3% GMO; there was a significant difference with 5% ICA at 4 hours and 5 hours; there was a significant difference with 3% GMO + 5% ICA at 5 hours and 6 hours.

[0040] Figure 5is a bar graph showing the results of a sensory panel comparison using a mixture of GMO and Hedione. The sensory panel compared the fragrance SP in EDT without and with 3% GMO; in EDT without and with 5% Hedione; in EDT without and with 3% GMO + 5% Hedione. No difference with 3% GMO, significant difference with 5% Hedione from 2 to 4 hours, significant difference with 3% GMO + 5% Hedione from 2 to 6 hours: significant difference. The formulation with the GMO-Hedione mixture performed better after 2 hours of evaporation.

[0041] Figure 6 A and B are bar graphs showing the performance of two highly volatile aroma ingredients, benzyl acetate and dihydromyrcenol, after 2, 4 and 6 hours of evaporation, and comparing them with the performance of the reference sample EDT0 (value 1). In the presence of phytantriol and in the presence of a mixture of phytantriol and a gelling agent, the intensity of the aromatizing ingredients increased significantly after 6 hours of evaporation.

[0042] Figure 7 A and B are bar graphs showing the intensity of (A) benzyl acetate containing 10% phytantriol, and benzyl acetate containing 10% phytantriol and β-cyclodextrin (CD); and (B) dihydromyrcenol containing 10% phytantriol, and dihydromyrcenol containing 10% phytantriol and β-cyclodextrin.

[0043] Figure 8 is a graph showing the total area summed over the entire evaporation process for the Research Accord HT1 formulation containing 5% phytantriol, 2% polyol and 0.3% EB21 compared to the RAHT1 formulation alone. The data shows that the sum of all compounds was retained more throughout the evaporation process for the 5% phytantriol, 2% polyol and 0.3% EB21 formulation compared to the control.

[0044] Fig. 9 is a graph showing the total area summed over the entire evaporation process for the Research Accord HT1 formulation containing 5% phytantriol, 2% Schercemol, and 0.3% EB21 compared to the RAHT1 formulation alone. The data shows that the sum of all compounds was retained more throughout the evaporation process for the 5% phytantriol, 2% Schercemol, and 0.3% EB21 formulation compared to the control.

[0045] Fig.10is a graph showing direct injection data for a 1 hour evaporation of the Research Accord HT1 formulation containing 5% phytantriol, 2% polyol and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds, with the most prominent high and mid volatile notes on the left.

[0046] Fig.11 is a graph showing direct injection data for a 1 hour evaporation of the Research accordHT1 formulation containing 5% phytantriol, 2% Schercemol and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds, with the most prominent high and medium volatile notes on the left.

[0047] Fig.12 is a graph showing direct injection data of a 2 hour evaporation of the Research accord HT1 formulation containing 5% phytantriol, 2% polyol and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds, with the most prominent high and mid volatile notes on the left.

[0048] Fig.13 is a graph showing direct injection data for a 2 hour evaporation of the Research accordHT1 formulation containing 5% phytantriol, 2% Schercemol and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds, with the most prominent high and medium volatile notes on the left.

[0049] Fig.14 is a graph showing direct injection data of a 4-hour evaporation of the Research accord HT1 formulation containing 5% phytantriol, 2% polyol and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds - with the most prominent mid- and low-volatility notes on the right - even after the majority of the high-volatility notes on the left have evaporated for 4 hours.

[0050] Fig.15 is a graph showing direct injection data of a 4-hour evaporation of the Research accordHT1 formulation containing 5% phytantriol, 2% Schercemol, and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds - with the most prominent mid- and low-volatility notes on the right - even after the majority of the high-volatility notes on the left have evaporated for 4 hours.

[0051] Fig.16is a graph showing direct injection data for a 6-hour evaporation of the Research accord HT1 formulation containing 5% phytantriol, 2% polyol and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds - with the most prominent mid- and low-volatility notes on the right - even after the majority of the high-volatility notes on the left have evaporated for 6 hours.

[0052] Fig.17 is a graph showing direct injection data for a 6-hour evaporation of the Research accordHT1 formulation containing 5% phytantriol, 2% Schercemol, and 0.3% EB21 compared to the HT1 formulation alone. The data show higher retention of all compounds - with the most prominent mid- and low-volatility notes on the right - even after the majority of the high-volatility notes on the left have evaporated for 6 hours. DETAILED DESCRIPTION

[0053] The present invention provides compositions that prolong the performance of fragrance oils. As used herein, "long-lasting fragrance composition" means that the fragrance oil according to the present invention has a prolonged performance relative to the fragrance oil alone. The prolonged performance can be measured by methods known in the art. For example, by quantitative GC-MS analysis after evaporation kinetics; by sensory panel rating of all intensities or rating of olfactory attributes.

[0054] The present invention provides compositions that improve fragrance performance by imparting a long-lasting fragrance perception perceived by the consumer during the wear of the fragrance while maintaining a clear, transparent, sprayable and stable hydroalcoholic formulation and solution with an acceptable skin feel.

[0055] The long-lasting fragrance composition of the present invention is suitable for use in consumer fragrance products for skin or hair containing volatile solvents (e.g., ethanol). In one embodiment, an atomizer can be used to dispense the long-lasting fragrance composition of the present invention into a micronized mist, which will enhance the fragrance performance due to the use of a dispensing system consisting of a multi-channel nozzle.

[0056] The long-lasting fragrance composition of the present invention can be diluted with a solvent (e.g., ethanol)-water mixture to obtain a final consumer product, such as perfume, eau de toilette, eau de parfum, moisturizing spray, body spray, body smear perfume, deodorant, hair spray, lotion, air care products and other solvent-based consumer products. Optionally, the long-lasting fragrance composition can be coupled with an unscented fragrance modulator, a scented fragrance modulator, an encapsulated macromolecule such as cyclodextrin and / or a fragrance precursor to enhance the lasting benefits.

[0057] The composition according to the invention may comprise: A) a hydrophobic active substance, such as a fragrance oil; B) an amphiphilic oil-soluble compound; C) a volatile solvent (such as ethanol) having an evaporation rate or vapor pressure higher than water (VP = 3.17 kPa at 25°C and 5.62 kPa at 35°C); D) water; E) a low molecular weight gelling agent and optionally F) a hydroptopic salt.

[0058] The amphiphilic oil-soluble compounds of the present invention include compounds having one of the following chemical structures:

[0059] or

[0060] wherein n represents the number of CH2 groups and is greater than 14, m represents the number of unsaturated CC bonds and is greater than or equal to 1, and Ri is one or a combination of the following groups:

[0061]

[0062]

[0063]

[0064] Serinolamide, methylpropanediolamide, ethylpropanediolamide, urea, urea alcohol, biuret, biuretol, N-arachidonic acid aminoethanol, glycerol ether and / or glycolipid. Amphiphilic oil-soluble compounds are easily soluble in volatile solvents, insoluble or slightly soluble in water, and have a packing parameter>1.

[0065] In certain forms, the amphiphilic oil-soluble compound is monoolein, phytantriol, a long chain fatty acid (more than 14 CH2) or a surfactant with a hydrophile-lipid balance (HLB) of less than 10.

[0066] The amphiphilic oil-soluble compound can be a surface active compound, such as a surfactant with HLB<10, a long chain fatty acid with CH2>14, and a fatty alcohol, such as myristyl, palmityl, oleyl, behenyl, and the like.

[0067] "Fragrance oils" according to the present invention include fragrances, fragrance ingredients, essential oils, and mixtures of aromatic compounds with natural ingredients such as essential oils, extracts and resins.

[0068] The fragrance oil may comprise 0.01% to 80% w / w of the long-lasting fragrance composition. In one aspect of the present invention, the fragrance oil may comprise 1% to 30% w / w of the long-lasting fragrance composition.

[0069] The gelling agent (gelling agent) according to the present invention can be a molecule from the class of low molecular weight gelling agents (LMWG) compounds, such as long chain (> 16 CH2) n-alkanes, hydroxyalkanoic acids such as hydroxy-octadecanoyl, hydroxy-hexadecanoyl, etc., dihydroxyalkanoic acids, dicarboxylic acids, fatty acid alkyl esters with alkyl chain lengths> 20 CH2 groups, hydroxyalkanols, steroidal derivatives such as glycyrrhizic acid, caffeine, anthracene derivatives, molecules containing steroids and fused aromatic rings, dendrimer n-alkanes, oligo(p-phenylene vinylene), dipyridyl urea-carboxylic acid combinations, diamine-linked dendrons, amino acid-based gelling agents such as dibutyl ethylhexanoyl glutamine and dibutyl lauroyl monoglycerol, 2-glycerol, glycerides, glycerol ethers, monoethanolamides, diethanolamides, glutamine, carbohydrate-derived gelling agents, peptide-based derivatives, etc. Preferred gelling agents are organic gelling agents. Preferred gelling agents are amino acid-based gelling agents and hydroxy fatty acid gelling agents.

[0070] The volatile solvent according to the present invention has a higher evaporation rate or vapor pressure than water. The vapor pressure of water at 35° C. is 5.62 kPa. In one form of the present invention, the volatile solvent is ethanol.

[0071] The long-lasting fragrance of the present invention may include a hydrotrope or hydrotropic salt (e.g. sodium salicylate). Suitable ranges of hydrotrope or hydrotropic salt are 0 to 5% w / w of the long-lasting fragrance, or 0.01% to 2% w / w of the long-lasting fragrance.

[0072] The long-lasting fragrance composition of the present invention may include a permeation agent. The permeation agent may be a slightly water-soluble compound, such as a moisturizer (e.g., glycols, such as dipropylene glycol, 1,3-butylene glycol, 1,2-propylene glycol, glycerol, pentanediol, hexanediol, 1,3-propylene glycol (propanediols), 1,4-butylene glycol (butanediols), xylitol), an emollient, a natural permeation agent (tetrahydropyrimidine) and a biopolymer. The permeation agent may account for 0 to 1% or 0.01% to 0.5% w / w of the long-lasting fragrance.

[0073] Consumer Products:

[0074] Leave-on consumer products containing volatile solvents, such as perfumes, eau de toilette, parfums, moisturizing sprays, body sprays, body rubs, hair sprays, air care sprays, leave-on hair care products, fabric fresheners, deodorants, etc.

[0075] Leave-on consumer products containing volatile solvents may also contain dyes, UV filters, antioxidants, quenchers, chelating agents, solubilizers, humectants, moisturizers, anti-aging actives, soothing agents, anti-pollution actives, emollients, or combinations thereof.

[0076] Example

[0077] The following examples illustrate but do not limit the invention.

[0078] Example 1 :Reference EDT (EDT0)

[0079] a) Formulation and process

[0080] A reference EDT formulation was prepared and used as a reference for evaluating fragrance performance. Water was added to ethanol as shown in Table 1. After stirring, fragrance was added to this solution. The final mixture was stirred until homogeneous.

[0081] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 70 Solvent water 20 Solvent Fragrance 10 Fragrance

[0082] Table 1

[0083] 1) Anhydrous ethanol; Source: Carlo Erba.

[0084] Example 2 :EDT containing phytantriol (EDT1)

[0085] b) Formulation and process

[0086] The amphiphilic oil-soluble compound phytantriol is dissolved in ethanol. Water is added to this solution. After stirring, a fragrance is added to this mixture. The final solution is stirred until homogeneous. See Table 2.

[0087] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 70 Solvent water 19 Solvent <![CDATA[Phytantriol 2) > 1 Amphiphilic oil-soluble compounds Fragrance 10 Fragrance

[0088] Table 2

[0089] 1) Anhydrous ethanol; product of Carlo Erba.

[0090] 2) 3,7,11,15-Tetramethylhexadecane-1,2,3-triol (phytantriol), a product of DSM.

[0091] Example 3 : EDT (EDT2) containing phytantriol and ammonium glycyrrhizinate (AGA)

[0092] a) Formulation and process

[0093] Phytantriol and ammonium glycyrrhizinate are mixed in ethanol. Water is added to this solution. After stirring, fragrance is added to this mixture. The final solution is stirred until homogeneous. See Table 3.

[0094] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 70 Solvent water 19 Solvent <![CDATA[Phytanetriol 2) > 0.75 Amphiphilic oil-soluble compounds <![CDATA[Ammonium glycyrrhizinate 3) > 0.25 Gel Fragrance 10 Fragrance

[0095] Table 3

[0096] 1) Anhydrous ethanol; Source: Carlo Erba.

[0097] 2) Phytantriol; Source: DSM.

[0098] 3) Ammonium glycyrrhizinate from liquorice root (Glycyrrhiza uralensis); Source: Sigma-Aldrich.

[0099] Example 4 : EDT containing phytantriol and caffeine (EDT3)

[0100] a) Formulation and process

[0101] Phytantriol and caffeine are mixed in ethanol. Water is added to this solution. After stirring, fragrance is added to this mixture. The final solution is stirred until homogeneous. See Table 4.

[0102] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 70 Solvent water 19 Solvent <![CDATA[Phytanetriol 2) > 0.75 Amphiphilic oil-soluble compounds <![CDATA[Caffeine 3) > 0.25 Gel Fragrance 10 Fragrance

[0103] Table 4

[0104] 1) Anhydrous ethanol; Source: Carlo Erba.

[0105] 2) Phytantriol; Source: DSM.

[0106] 3) Caffeine; Source: Fluka Analytical.

[0107] Example 5 : EDT containing phytantriol and sodium salicylate (EDT4)

[0108] a) Process

[0109] Phytantriol and sodium salicylate are mixed in ethanol. Water is added to this solution. After stirring, fragrance is added to this mixture. The final solution is stirred until homogeneous. See Table 5.

[0110] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 70 Solvent water 18.8 Solvent <![CDATA[Phytanetriol 2) > 1 Amphiphilic oil-soluble compounds <![CDATA[Sodium salicylate 3) > 0.2 Hydrotropic salt Fragrance 10 Fragrance

[0111] Table 5

[0112] 1) Anhydrous ethanol; Source: Carlo Erba.

[0113] 2) Phytantriol; Source: DSM.

[0114] 3) Sodium salicylate, 99%; Source: Alfa Aesar.

[0115] Example 6 : EDT containing monoolein

[0116] Mix glyceryl monooleate (GMO) into ethanol. Add water to this solution. After stirring, add fragrance to this mixture. Stir the final solution until homogeneous. See Table 6.

[0117] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 72 Solvent water 15 Solvent <![CDATA[Glycerol monooleate 2) > 3 Structural amphiphilic oil-soluble compounds Fragrance 10 Fragrance

[0118] Table 6

[0119] 1) Anhydrous ethanol; Source: Carlo Erba.

[0120] 2) Glyceryl monooleate; Source: Dupont.

[0121] Example 7 : EDT containing isocetyl alcohol

[0122] Mix isocetyl alcohol (ICA) in ethanol. Add water to this solution. After stirring, add fragrance to this mixture. Stir the final solution until homogeneous. See Table 7.

[0123] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 70 Solvent water 15 Solvent <![CDATA[Isocetyl alcohol 2) > 5 Conditioner Fragrance 10 Fragrance

[0124] Table 7

[0125] 1) Anhydrous ethanol; Source: Carlo Erba.

[0126] 2)Isocetyl alcohol; Source: Ashland.

[0127] Example 8 : EDT containing glyceryl monooleate and isocetyl alcohol

[0128] Glyceryl monooleate (GMO) and isocetyl alcohol (ICA) were mixed in ethanol. Water was added to the solution. After stirring, fragrance was added to the mixture. The final solution was stirred until homogeneous. See Table 8.

[0129] Element Amount (%wt) Function <![CDATA[Ethanol 1) > 67 Solvent water 15 Solvent <![CDATA[Glycerol monooleate 2) > 3 Amphiphilic oil-soluble compounds <![CDATA[Isocetyl alcohol 3) > 5 Conditioner Fragrance 10 Fragrance

[0130] Table 8

[0131] 1) Anhydrous ethanol; Source: Carlo Erba.

[0132] 2) Glyceryl monooleate; Source: Dupont.

[0133] 3) Isocetanol; Source: Ashland.

[0134] Example 9 : EDT containing glyceryl monooleate, nerolidol and dibutyl ethylhexanoyl glutamine

[0135] Glyceryl monooleate (GMO), nerolidol and dibutyl ethylhexanoyl glutamine (EB-21) were mixed in ethanol. Water was added to the solution. After stirring, fragrance was added to the mixture. The final solution was stirred until homogeneous. See Table 9.

[0136] Element Amount (%wt) Function Ethanol 70.70 Solvent water 15 Solvent Glyceryl Monooleate 3 Amphiphilic oil-soluble compounds Nerolidol 1 Conditioner Dibutyl Ethylhexanoyl Glutamine 0.3 Gel Fragrance 10 Fragrance

[0137] Table 9

[0138] Example 10 : EDT containing glyceryl monooleate, nerolidol, polyhydroxymethylol and dibutyl ethylhexanoyl glutamine

[0139] Glyceryl monooleate (GMO), nerolidol, polyhydroxymethylol and dibutyl ethylhexanoyl glutamine (EB-21) were mixed in ethanol. Water was added to this solution. After stirring, fragrance was added to this mixture. The final solution was stirred until uniform. See Table 10.

[0140] Element Amount (%wt) Function Ethanol 69.70 Solvent water 15 Solvent Glyceryl Monooleate 3 Amphiphilic oil-soluble compounds Nerolidol 1 Conditioner Polyhydroxymethyl 1 Conditioner Dibutyl Ethylhexanoyl Glutamine 0.3 Gel Fragrance 10 Fragrance

[0141] Table 10

[0142] Embodiment 11 : EDT containing glyceryl monooleate, nerolidol, polyhydroxymethylol and dibutyl ethylhexanoyl glutamine

[0143] Glyceryl monooleate (GMO), polyhydroxymethyl and dibutyl ethylhexanoyl glutamine (EB-21) were mixed in ethanol. Water was added to the solution. After stirring, fragrance was added to the mixture. The final solution was stirred until uniform. See Table 11.

[0144] Element Amount (%wt) Function Ethanol 69.70 Solvent water 15 Solvent Glyceryl Monooleate 3 Amphiphilic oil-soluble compounds Polyhydroxymethyl 2 Conditioner Dibutyl Ethylhexanoyl Glutamine 0.3 Gel Fragrance 10 Fragrance

[0145] Table 11

[0146] Example 12 -Performance

[0147] a) Process

[0148] Evaporation kinetics studies were performed. Test and reference compositions were deposited on the glass bottom of headspace vials and evaporated under stirring at 32°C (corresponding to skin temperature) after 2 hours, 4 hours, 6 hours or sometimes 24 hours. At a given moment, the vials were closed and placed at 32°C to saturate the headspace. A small amount of saturated headspace vapor was injected into a GC-MS instrument and the vapor composition was analyzed.

[0149] Sample preparation

[0150] For kinetic analysis, six identical samples were prepared simultaneously. For each sample, a piece (1×1 cm) of scent paper (Scentis, 160 mm×20 mm) was placed at the bottom of a 20 mL headspace-GCMS screw cap vial (BGB Analytik, 180420). 10 μL of EDT-type sample was deposited on the scent paper using a micropipette. All vials were closed after the desired evaporation time (0 h, 2 h, 4 h, or 6 h).

[0151] The CTC PAL was installed on a GC-MS (6890 Series GC System and 5973 Network MS) for injection. The CTC PAL was equipped with a 1 mL injection needle. 1 mL of headspace gas was taken from the sample and injected into the GC-MS instrument. Before each injection, the designer of the GCMS stirred the sample at 32°C for 30 minutes.

[0152] GC parameters

[0153] Agilent GC was used with a split / splitless inlet and helium as carrier gas. A septum BTO (Bleed & Temp Optimized septum, 11 mm / Agilent 5183-4757) was installed and the liner was heated to 250°C (liner, splitless, single trap, deactivated / Agilent 5181-3316). Samples were analyzed with a split ratio of 5:1.

[0154] A non-polar column was installed in an oven. (Agilent_19091S-433_HP-5MS – bound with a fused silica capillary column, PDMS ((5%-phenyl)-methylpolysiloxane – length 30 m, diameter 250 μm, film thickness 0.25 μm). The analysis was performed at a constant flow rate with an initial flow rate of 1 mL / min (corresponding to an average velocity of 36 cm / s). The oven program started at 40°C. The temperature was increased to 150°C at a ramp rate of 20°C / min and then to 250°C at a ramp rate of 50°C / min. The oven maintained the temperature at 250°C for one minute.

[0155] MS parameters – SIM method

[0156] The SIM method was used to determine the aromatized components in the headspace gas. No solvent delay was used. Masses between 35 and 320 were analyzed with a threshold of 25.

[0157] b) Results

[0158] 1) Performance of single fragrance ingredients

[0159] The fragrance ingredient styraxyl acetate (supplied by Firmenich SA, volatility equal to 1320.4 μg / L air) was dissolved in formulations EdT1-4 and deposited according to the above "Sample Preparation". Figure 1 The values ​​are shown as relative to the reference EdT formulation intensity in . The results show that formulations EDT 1 to 4 have an improved aroma performance after 2 hours and even after 4 hours of evaporation compared to the reference sample corresponding to 1 (EDT0).

[0160] 2) Model spice mixture performance

[0161] Test 1:

[0162] Model fragrance A shown in Table 12 was dissolved in EDT2 and deposited as described in “Sample Preparation”. The intensity of the fragrance components was tracked at different times during the evaporation process. The performance of the fragrance components 6 hours after deposition was Figure 2 The values ​​are shown as relative intensities to the reference EdT formulation. Values ​​>1 indicate intensities greater than the reference EdT0.

[0163]

[0164] Table 12

[0165] Test 2:

[0166] Table 13. Research Accord HT1 (RAHT1) used in this experiment consists of the following 44 components in equal concentrations, ranging from high to low volatility components.

[0167]

[0168] Table 14A-C. The following are the three formulations tested - a model fragrance as a control (RAHT1 in EDT), Technology 1 as a model fragrance containing 5% Phytantriol, 2% Polyhydroxymethyl, 0.3% EB-21 gellant, and Technology 2 as a model fragrance containing 5% Phytantriol, 2% Schercemol, 0.3% EB-21 gellant.

[0169]

[0170] The methods used are as follows:

[0171] Evaporation was performed in a Tzero cover. A Prazitherm PZ72 slide heater was preheated to 32 degrees Celsius for 30 minutes. Each crucible was placed on a precision hotplate. Using a variable volume pipette, 10 μL of fragrance was injected directly into the center of the crucible and evaporated on a precision hotplate at 32 °C for 1 hour, 2 hours, 4 hours, and 6 hours. Repeat for each sample and each test condition. After reaching the time point, each crucible was placed in a 2-mL Agilent GC sample vial (Agilent 5183-2068) and 600 μL of ethanol was added to stop evaporation. The vial was capped and mixed by shaking for at least 1 minute. Samples were analyzed by GC-MS direct injection method. See Figures 8 to 17 .

[0172] 3) Effect of concentration of amphiphilic oil-soluble compounds

[0173] Effect of concentration of amphiphilic oil-soluble compounds on the retention of fragrance ingredients Figure 3 As shown. Fragrance A was dissolved at 10%wt in a mixture of ethanol, water, and phytantriol at different phytantriol concentrations. The water concentration was kept constant and equal to 20%wt. Increasing the phytantriol concentration led to better results; after 6 hours of evaporation, the highly volatile benzyl acetate and dihydromyrcenol had higher concentrations in the headspace compared to the reference sample.

[0174] 4) Sensory evaluation in the presence of phytantriol or monoolein or a mixture

[0175] Sensory evaluation of aroma intensity was performed. 20 μl of the formulation was deposited on a glass plate, which was maintained at 32° C. on a heating platform. At different times (t=0 min (fresh), 2 h, 4 h, 5 h and 6 h), the glass plates were randomly evaluated by 15 panelists.

[0176] The test was conducted using the 3-Alternative Forced Choice (or 3-AFC) method. For each time point, the panelists were presented with 3 samples, two of which were fragrances (SP) and one was a fragrance according to the present invention. The panelists indicated the sample with the higher overall intensity.

[0177] Assumptions:

[0178] -H0: There is no difference between the two samples.

[0179] -H1: In terms of overall intensity, samples with technology are more intense than samples without technology.

[0180] Related risks:

[0181] -H0 rejected = α risk:

[0182] -The risks associated with false positives, concluding that products are different when in fact they are not.

[0183] Data were analyzed using binomial statistics.

[0184] Data interpretation:

[0185] - If a p-value is obtained for α ≤ 0.05, then the sample with technology is stronger than the sample without technology in terms of overall strength

[0186] - If a p-value is obtained for α of 0.05 < α ≤ 0.10, a trend difference is determined.

[0187] - If a p-value is obtained for α > 0.10, then the samples are not significantly different.

[0188] Fragrance SP contains 44% fragrance ingredients with logP<4 (high volatility).

[0189] The results of the sensory panel presented in Table 15 show that the formulation according to the invention performs better after 4 hours of evaporation in the presence of 10% phytantriol and after 2 hours of evaporation in the presence of 10% GMO.

[0190]

[0191] Table 15

[0192] The performance of mixtures of GMO and ICA was studied.

[0193] Sensory panels were conducted in turn to compare:

[0194] - Fragrance SP in EDT without and with 3% GMO (Table 6),

[0195] - Fragrance SP in EDT without and with 5% ICA (Table 7),

[0196] - Fragrance SP in EDT without and with 3% GMO + 5% ICA (Table 8).

[0197] Figure 4 The results presented in show:

[0198] -Contains 3% GMO: No difference,

[0199] -Containing 5% ICA: There was a significant difference between 4 and 5 hours,

[0200] -Containing 3% GMO + 5% ICA: There was a significant difference between 5 hours and 6 hours.

[0201] After 5 hours of evaporation, the formulation containing the GMO-ICA mixture performed better.

[0202] The same experiment was performed using a mixture of GMO and Hedione.

[0203] Sensory panels were conducted in turn to compare:

[0204] - Fragrance SP in EDT without and with 3% GMO (Table 6)

[0205] - Fragrance SP in EDT without and with 5% Hedione (Table 7).

[0206] - Fragrance SP in EDT without and with 3% GMO + 5% Hedione (Table 8)

[0207] Figure 5 The results presented in show:

[0208] -Contains 3% GMO: No difference,

[0209] -Contains 5% Hedione: Significant difference between 2 and 4 hours,

[0210] -Contains 3% GMO + 5% Hedione: There is a significant difference from 2 to 6 hours.

[0211] After 2 hours of evaporation, the formula containing the GMO-Hedione mixture performed better.

[0212] 5) Examples of Synergistic Mixtures

[0213] Mixtures of an amphiphilic oil-soluble compound (phytantriol) and a fixative (ICA) or a gelling agent (EB-21) were prepared and incorporated into an ethanol-water solution in the proportions shown in Table 2. The performance of two highly volatile fragrance ingredients, benzyl acetate and dihydromyrcenol, was followed after 2, 4 and 6 hours of evaporation and compared with that of the reference sample EDT0 (value 1). In the presence of phytantriol and the mixture of phytantriol and gelling agent, the intensity of the aromatizing ingredients increased significantly after 6 hours of evaporation. Figure 6 .

[0214] Mixtures of (A) benzyl acetate with 10% phytantriol, and benzyl acetate with 10% phytantriol and β-cyclodextrin (CD); and (B) dihydromyrcenol with 10% phytantriol, and dihydromyrcenol with 10% phytantriol and CD were prepared and incorporated into ethanol-water solutions in the proportions mentioned in Table 2. The performance of two highly volatile fragrance ingredients, benzyl acetate and dihydromyrcenol, was followed after evaporation for 2, 4 and 6 hours. The intensity of the mixture containing CD was greater. See Figure 7 .

[0215] Mixtures of fragrances SP and LS with GMO and with conditioners and gelling agents were prepared and incorporated into ethanol-water solutions in the proportions mentioned in Tables 9, 10 and 11. The glass plates were randomly evaluated by 7 panelists after different moments t=0 minutes (fresh), 4 hours and 6 hours. The results presented in Table 16 show that after 4 hours of evaporation, for both fragrances SP and LS, the formulations according to the invention have a better performance compared to the control.

[0216] The combination of 3% GMO, 1% Nerolidol and 0.3% EB-21 was the most effective as it provided better performance for both fragrances SP and LS after 4 and 6 hours.

[0217] The lower p-value of fragrance LS compared to SP indicates that LS has a better performance, which may be related to its fragrance structure containing more core notes.

[0218]

[0219] *N=number of team members

[0220] Table 16

[0221] The influence of fragrance structure

[0222] The sensory panel evaluated model fragrances with different configurations that deviated from the typical pyramid construction (medium volatility components were present at higher levels than low and high volatility components) and were tested in the presence of GMO solutions.

[0223] The results presented in Table 17 indicate that the performance using GMOs depends on the fragrance architecture based on the volatility of the fragrance raw materials.

[0224] The results shown below are based on the perceived intensity of the panel at 10% fragrance in the presence of 3% GMO compared to 10% fragrance alone. Improved performance was observed when the percentage of correct answers was >55% with the listed significance (p-value).

[0225]

[0226] Table 17

[0227] The fragrance formula gives an extra boost of performance and includes the following aromatic ingredients:

[0228] ● Volatile ingredients, ranging from 35% to 100% by weight of the fragrance ingredients, including at least one fragrance raw material having a first vapor pressure greater than 0.0008 Torr at 22°C;

[0229] ●And, in the above fragrance structure:

[0230] ○ Configuration 1 - Volatile ingredients, in an amount of 40-100 wt% of the fragrance ingredients, comprising at least one fragrance raw material having a first vapor pressure greater than 0.08 Torr and optionally, at least one second fragrance raw material having a first vapor pressure greater than 0.08 Torr at 22°C;

[0231] ○ Structure 2 - Volatile ingredients, in an amount of 0.08 to 85 wt % of the fragrance ingredients, comprising a first at least one fragrance raw material having a first vapor pressure ranging from 0.0008 to 0.08 Torr at 22°C; and optionally, a second at least one fragrance raw material having a first vapor pressure ranging from 0.0008 to 0.08 Torr at 22°C;

[0232] c) Conclusion

[0233] Comparison of these different evaporation kinetics shows that the formulations of the present invention have higher fragrance retention than standard eau de toilette compositions. In the EdT formulations of the present invention containing an amphiphilic oil-soluble compound (phytantriol) and a low molecular weight gelling agent, fragrance retention is significant. The long-lasting performance of the present invention relative to the standard EdT formulation is demonstrated 4 to 6 hours after deposition. It was surprisingly found that the synergistic mixture provides better fragrance retention.

[0234] Publications cited throughout this article are incorporated herein by reference in their entirety. Although various aspects of the present invention have been described above with reference to examples and preferred embodiments, it should be understood that the scope of the present invention is not limited by the foregoing description, but is defined by the appended claims appropriately interpreted under the principles of patent law.

Claims

1. A long-lasting fragrance composition, comprising: a. Fragrance oil, b. 0.01% to 40% w / w of an amphiphilic oil-soluble compound based on the long-lasting fragrance composition, c. volatile solvents, and d. Water, and e. Gel; The amphiphilic oil-soluble compound includes a compound having one of the following chemical structures: or wherein n represents the number of CH2 groups and is greater than 14, m represents the number of unsaturated CC bonds and is greater than or equal to 1, and Ri is selected from the group consisting of: and combinations thereof; and The gel is selected from the group consisting of glycyrrhizic acid, caffeine, dibutyl ethylhexanoyl glutamine, dibutyl lauroyl glutamine, and combinations thereof.

2. The long-lasting fragrance composition according to claim 1, wherein the amphiphilic oil-soluble compound accounts for 0.5% to 30% w / w of the long-lasting fragrance composition.

3. The long-lasting fragrance composition according to claim 1, wherein the gelling agent accounts for 0.01 to 15% w / w of the long-lasting fragrance composition.

4. The long-lasting fragrance composition according to claim 3, wherein the gelling agent accounts for 0.3 to 0.6% w / w of the long-lasting fragrance composition.

5. The long-lasting fragrance composition according to claim 1, wherein water accounts for 0.01 to 60% w / w of the long-lasting fragrance composition.

6. The long-lasting fragrance composition according to claim 5, wherein the amphiphilic oil-soluble compound accounts for 0.5 to 10% w / w of the long-lasting fragrance composition.

7. The long-lasting fragrance composition according to claim 6, wherein water accounts for 0.7% to 60% w / w of the long-lasting fragrance composition.

8. The long-lasting fragrance composition according to claim 7, wherein water accounts for 0.7 to 50% w / w of the long-lasting fragrance composition.

9. The long-lasting fragrance composition according to claim 8, wherein water accounts for 1% to 30% w / w of the long-lasting fragrance composition.

10. The long-lasting fragrance composition according to claim 1, wherein the volatile solvent is selected from the group consisting of ethanol, isopropanol, ether and mixtures thereof.

11. The long-lasting fragrance composition according to claim 1, further comprising a regulator.

12. The long-lasting fragrance composition according to claim 11, wherein the modulator is selected from the group consisting of: methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol di(ethylhexanoate); sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether; polyglyceryl-4 ether; isoceteth-5; isocetyl alcohol polyether-6; isocetyl alcohol polyether-7; isocetyl alcohol polyether-8; isocetyl alcohol polyether-9; isocetyl alcohol polyether-10; isocetyl alcohol polyether-11; isocetyl alcohol polyether-12; isocetyl alcohol polyether-13; isocetyl alcohol polyether-14; isocetyl alcohol polyether-15; isocetyl alcohol polyether-16; isocetyl alcohol polyether-17; isocetyl alcohol polyether-18; isocetyl alcohol polyether-19; isocetyl alcohol polyether-20 Ceteth-7, Isoceteth-10; Isoceteth-12; Isoceteth-15; Isoceteth-20; Isoceteth-25; Isoceteth-30; Disodium laurylamphodipropionate; Hexaethylene glycol monododecyl ether; Neopentyl glycol diisononanoate; Cetearyl ethylhexanoate; Panthenol ethyl ether, DL-panthenol, Hexadecyl nonanoate, Octadecyl nonanoate, Nerolidol, Fragrance precursors, Coolants, Cyclodextrins, Fatty acids, Fatty alcohols, Polyglyceryl fatty acid esters, Diglyceryl oleate, and combinations thereof.

13. The long-lasting fragrance composition according to claim 1, wherein the amphiphilic oil-soluble compound is glyceryl monooleate or phytantriol or a combination thereof.

14. The long-lasting fragrance composition according to claim 11, wherein the conditioning agent is nerolidol.

15. The long-lasting fragrance composition according to claim 11, comprising: an amphiphilic oil-soluble compound comprising 1% to 10% w / w of the composition; a conditioning agent at 0.5% to 15% w / w of the composition; A gelling agent comprising 0.1% to 10% w / w of the composition, and Water comprises from 1% to 40% w / w of the composition.

16. The long-lasting fragrance composition according to claim 15, wherein the amphiphilic oil-soluble compound accounts for 1% to 6% w / w of the composition, the conditioning agent accounts for 1% to 5% w / w of the composition, the gelling agent accounts for 0.1 to 3% w / w of the composition, and water accounts for 5% to 30% w / w of the composition.

17. The long-lasting fragrance composition according to claim 16, comprising 3% w / w of the amphiphilic oil-soluble compound, 1% to 5% w / w of the regulator and 0.3% w / w of the gelling agent.

18. The long-lasting fragrance composition according to claim 15, wherein the amphiphilic oil-soluble compound is glyceryl monooleate, the gelling agent is dibutyl ethylhexyl glutamine, and the conditioning agent is nerolidol.

19. The long-lasting fragrance composition according to claim 1, wherein 40 to 100% of the fragrance oil is a volatile component, which comprises at least one fragrance raw material having a vapor pressure greater than 0.0008 Torr at 22°C.

20. The long-lasting fragrance composition according to claim 19, wherein the volatile component comprises at least one fragrance raw material having a vapor pressure greater than 0.08 Torr.

21. The long-lasting fragrance composition according to claim 20, further comprising a second fragrance raw material having a vapor pressure greater than 0.08 Torr at 22°C.

22. The long-lasting fragrance composition according to claim 1, wherein 0.08 to 85% of the fragrance oil is a volatile component, which comprises at least one fragrance raw material having a vapor pressure of 0.0008 to 0.08 Torr at 22°C.

23. The long-lasting fragrance composition according to claim 22, further comprising a second fragrance raw material having a vapor pressure of 0.0008 to 0.08 Torr at 22°C.

24. A disposable consumer product containing a volatile solvent, comprising the long-lasting fragrance composition according to claim 1.

25. The disposable consumer product containing volatile solvents according to claim 24, wherein the consumer product is selected from the group consisting of: perfume, eau de toilette, cologne, moisturizing spray, body spray, hair spray, air care spray, disposable hair care products, fabric freshener and deodorant.

26. The disposable consumer product containing a volatile solvent according to claim 24, wherein the consumer product is an eau de toilette.

27. The disposable consumer product containing a volatile solvent according to claim 24, wherein the consumer product is a body perfume.

28. The disposable consumer product containing volatile solvents according to claim 24, further comprising a dye, a UV filter, an antioxidant, a quencher, a chelating agent, a solubilizer, a wetting agent, a moisturizer, an anti-aging active agent, a soothing agent, an anti-pollution active agent, an emollient, a pearlescent compound or a combination thereof.

29. The disposable consumer product containing a volatile solvent according to claim 24, further comprising a dispensing system.

30. Use of a long-lasting fragrance composition as claimed in any one of claims 1 to 23 for prolonging the performance of a fragrance oil.

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