WO2002004587A1

WO2002004587A1 - Process for imparting conditioning and good fragrance perception to both damp and dry fabric

Info

Publication number: WO2002004587A1
Application number: PCT/US2001/021334
Authority: WO
Inventors: Thomas Mcgee; Kenneth Leo Purzycki
Original assignee: Givaudan S.A.
Priority date: 2000-07-07
Filing date: 2001-07-05
Publication date: 2002-01-17
Also published as: AU2001270305A1; EP1299514A1

Abstract

The present invention provides a process for conditioning and fragrancing a substrate. This process includes contacting a fragrance delivery vehicle containing a water insoluble oil, a cationic active, and at least 0.1 %(wt) of a fragrance composition with a substrate in an aqueous solution. Compositions for conditioning and fragrancing a substrate are also provided.

Description

PROCESS FOR IMPARTING CONDITIONING AND GOOD FRAGRANCE PERCEPTION TO BOTH DAMP AND DRY FABRIC

FIELD OF THE INVENTION

The present invention relates to a process for imparting optimal fragrance perception to damp and dry fabric. More particularly, the invention relates to a process for conditioning and fragrancing a substrate by providing a fragrance delivery vehicle containing a water insoluble oil, a conditioner containing a cationic active, and a fragrance composition specifically designed for the delivery vehicle. A substrate is then contacted with the fragrance delivery vehicle in an aqueous solution. Compositions are also provided for conditioning and fragrancing a substrate.

BACKGROUND OF THE INVENTION

Liquid conditioning products for treating substrates, such as hair and fabric conditioners, contain cationic materials as a key active ingredient. Other ingredients, such as oils as described in WO 97/44424, may be used in liquid conditioning products together with a cationic active to aid in the deposition of fabric treatment agents. (See also WO98/16538, which is incorporated by reference as if recited in full herein.). Such oils, as part of the conditioner, may be delivered during the final rinse.

It is known that the composition of a fragrance for a liquid conditioner must provide fragrance in sufficient quantities to be perceived in the product, during use on damp and dry substrates. The principles of achieving substantivity and longevity on treated substrates are disclosed by Muller et al., "What Makes A Fragrance Substantive" Perfumer and Flavorist, 1845-1849 (1993) and Escher et al, "A Quantitative Study of Factors that Influence the Substantivity of Fragrance Chemicals on Laundered and Dried Fabrics," JOACS, vol. 71, no. 1 (1994). Muller discloses that the greater the quantity of water insoluble aroma chemicals with low vapor pressures in the fragrance composition, the greater the substantivity of the fragrance. The solubility of an aroma chemical is usually measured, such as described in, for example Etsweiler et al., Analytical Chemistry 67; 655-658 (1995). Low solubility is highly correlated with the hydrophobicity of an aroma chemical.

Escher uses hydrophobicity, determined as the partition coefficient of the chemical between octanol and water and expressed as log P. Similar to Muller' s disclosure that the higher the log P value, the greater the substantivity. Log P may be measured directly but more conveniently it may be calculated from the structure of the molecule, using one of several commercially available software programs, such as ACD Software, ACD/logP calculator version 4.0, Advanced Chemistry Development, Toronto, Ontario Canada. The calculated value is abbreviated to CLogP.

The vapor pressure of an aroma chemical, which is related to its boiling point, is also included to ensure that it does not evaporate during the rinse cycle to which the conditioner is added, and that it survives the drying process ensuring that sufficient aroma chemical is present to provide a lasting scent on the dry substrate. High boiling point aroma chemicals will evaporate more slowly giving a longer lasting fragrance perception. Vapor pressure and boiling point may be measured or calculated using one of the commercially available software programs, such as ACD Software ACD/Boiling Point calculator version 4.0.

Another way to impart good fragrance to a substrate is to have the substantive part of the fragrance composed of an aroma chemical with low perception thresholds. The lower the perception threshold of an aroma chemical, the lower the quantity that is required to smell it. A variety of techniques are available to determine the perception threshold. See e.g., Neuener-Jehle and Etzweiler in Art Science and Technology, editors Lampaski and Muller, ch.6, 153-212 (1991).

Bacon, et al, U.S. Patent No. 5,652,206 discloses that for enduring fragrances, a fragrance must be composed of at least 70% aroma chemicals with a CLogP > 3.0 and a boiling point of >250°C at 760 mm Hg. Similarly, Trihn, et al, U.S. Patent No. 5,833,999 uses the same criteria for defining enduring fragrances for hair and skin products.

The active agents disclosed as conditioners by these patents are predominantly cationic, having at least one of the alkyl chains with a chain length at least equal to 12, preferably greater than 16. The level of cationic active used in the conditioner product depends upon whether the product is dilute or concentrated. The levels of active in dilute products ranges from l%(wt) to 7%(wt) and in concentrated products from 10%( t) to 20%(wt). In summary, optimum fragrancing of both damp and dry substrates has been difficult to achieve using the methods summarized above, which rely solely on water insolubility, boiling point, and perception threshold.

SUMMARY OF THE INVENTION

In the present invention, it has been found that enhanced deposition of fragrance onto a treated substrate is achieved with a cationic active and a water insoluble oil. This gives enhanced fragrance perception on dry fabric, however, in order to maintain at least equal perception on a damp fabric to that achieved from a simple cationic conditioning vehicle, one has to formulate the fragrance differently than the prior art teaches.

Surprisingly, it has been found that a water insoluble oil, when combined with a cationic active, provides excellent fragrance deposition and perception on both damp and dry substrates, such as fabrics or hair, so long as the fragrance composition is constructed according to the present invention.

In particular, the inclusion of an oil in, e.g. a fragrance delivery vehicle enliances the deposition of a substantive aroma chemical, i.e. one that has a CLogP higher than 3.0. These oils may be present in dilute products from 0.5%(wt) to 7%(wt) and in concentrated products from l%(wt) to 20%(wt).

Thus, in the present process, it is now possible to maintain an enhanced perception of the fragrance from, e.g., a dry fabric, and maintain at least equal perception from, e.g., the damp fabric if the composition of the fragrance is constructed as set forth in more detail below.

Accordingly, one embodiment of the invention is a process for conditioning and fragrancing damp and dry substrates. This process includes providing a fragrance delivery vehicle containing a conditioner having a cationic active at a level above 0.5%(wt), a water insoluble oil, and up to 5%(wt) of a fragrance composition, wherein the fragrance composition provides enhanced perception on dry treated substrates and maintains good perception on damp treated substrates when added to the final rinse of a washing process.

Another embodiment of the invention is a process for conditioning and fragrancing a substrate. This process includes providing a fragrance delivery vehicle containing a conditioner having a cationic active, a water insoluble oil, and at least 0.1%(wt) of a fragrance composition. The fragrance delivery vehicle is then contacted with a substrate in an aqueous solution.

Another embodiment of the invention is a fragrance delivery vehicle.

This fragrance delivery vehicle includes a water insoluble oil, a conditioner containing a cationic active, and at least 0.1%(wt) of a fragrance composition consisting of at least 2 %(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 and a vapor pressure at 25°C of less than 0.02 mm Hg.

A further embodiment of the invention is a fragrance delivery vehicle made by the process of combining a water insoluble oil, a conditioner containing a cationic active, and at least 0.1 %(wt) of a fragrance composition consisting of at least 2%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 and a vapor pressure at 25°C of less than 0.02 mm Hg. Another embodiment of the invention is a process for enhancing the fragrance of a consumer product. This process includes incorporating a fragrance improving quantity of the fragrance delivery vehicle of the invention into a consumer product.

DETAILED DESCRIPTION OF THE INVENTION

The process according to the present invention includes providing a fragrance delivery vehicle containing a water insoluble oil, a cationic active in a fabric conditioner, and a fragrance composition to provide enhanced fragrancing of both damp and dry substrates, such as a fabric or hair. The fragrance delivery vehicle is then contacted with a substrate in an aqueous solution.

In the present invention, the fragrance delivery vehicle is contacted with the substrate using any conventional method, such as for example by adding it to the rinse cycle of a conventional washing machine in the case of a fabric. The fragrance delivery vehicle is contacted with the substrate in an aqueous solution. In the present invention, the aqueous solution is water or a solution containing a substantial amount of water that is suitable for fabric or hair washing.

As used herein, the term "substrate" means hair or a fabric (natural, synthetic, or natural/synthetic blends) that is suitable for conventional washing and drying.

The fragrance delivery vehicle contains a cationic active above

0.5%(wt), a water insoluble oil above 0.1%(wt), and a fragrance composition above 0.1%(wt). The fragrance composition contains at least 2%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP greater than 4.0 and a vapor pressure of less than 0.01 mm Hg, preferably less than 0.008 mm Hg, at 25°C.

The aroma chemical in the fragrance composition will have a perception threshold below 100 ng per liter at 25°C, preferably, a perception threshold below 50 ng per liter at 25°C, such as for example, a perception threshold below 30 ng per liter at 25°C. hi the present invention, the CLogP and vapor pressure were calculated using ACD/CLogP calculator version 4.0 and ACD/Boiling Point calculator version 4.0, respectively, from Advanced Chemicals Development ACD/Labs Software (Toronto, Ontario, Canada).

As used herein, the phrase "fabric conditioner" means a product that imparts softness, drape, and other similar benefits, such as antistatic properties, color care properties, etc., to fabrics. As used herein the phrase "hair conditioner" means a product that imparts softness, easier combing, and shine to hair. In the present invention, the term "conditioner" is used throughout to refer to fabric conditioners, hair conditions, or both, as the context may dictate.

The phrase "aroma chemical" as used herein means a chemical that is volatile and that is detected by the nose as a smell. As noted above, the phrase "perception threshold" means the lowest quantity of an aroma chemical, in the vapor phase that may be perceived by the nose.

The cationic active in the conditioning delivery vehicle may be, for example, dialkyldimethyl ammonium chloride, dialkyldimethyl ammonium methyl sulfate, di (hydrogenated tallow) dimethyl ammonium chloride, dihexadecyldiethylammonium chloride, distearyldimethylammonium chloride, dibehenyldimethylammoinium chloride, di(coconut alkyl)dimethyl ammonium chloride, ditallowdimethyl ammonium chloride, ester quaternium compounds, dialkylyloxy dimethyl ammonium chloride, N,N-di(tallowyl-oxy-ethyl)-N N- dimethylammonium chloride, N N-(ditallowoxyl-oxy-ethyl)-N,N-dimethyl ammonium chloride, dialkyl imidazolium methyl sulfate, amido silicones, and mixtures thereof. The level of cationic active in a dilute f agrance delivery vehicle of the invention may be 0.5%(wt) - 7.0%(wt), preferably 0.75%(wt) - 6.0%(wt), such as for example, 1.0%(wt) - 5.0%(wt). Levels of the cationic active in a concentrated delivery vehicle of the invention may be from 7%(wt) to 20%(wt), preferably 10%(wt) to 15%(wt). The water insoluble oils of the fragrance delivery vehicle may be selected from, for example, mineral oils, ester oils, sugar ester oils or oily sugar derivative, natural oils, such as vegetable oils, and mixtures thereof. The level of water insoluble oil in a dilute fragrance delivery vehicle of the invention is 0.1%(wt) - 7.0% (wt), preferably 0.3%(wt) - 6.0%( t), such as for example, 0.5%(wt) - 5.0%(wt). In a concentrated fragrance delivery vehicle of the invention the level of water insoluble oil is l%(wt) - 25%(wt), preferably 3%(wt)-20%(wt). It is preferred that the water insoluble oil used in the present invention be in liquid form.

In the present invention, the terms "sugar ester oil," "sucrose poly ester" (SPE), and "oily sugar derivative" are used interchangeably and are defined in detail in WO 00/7004, which is incorporated by reference as if recited in full herein. Preferably, the ester oils are esters containing straight or branched, saturated or unsaturated carboxylic acids. The ester oil or oily sugar derivative is a liquid or soft solid derivative of a cyclic polyol or of a reduced saccharide, said derivative resulting from 35 to 100% of the hydroxyl groups in said polyol or in said saccharide being esterified or etherified. The derivative has two or more ester or ether groups independently attached to a C₈-C₂₂ alkyl or alkenyl chain.

The oily sugar derivatives of the invention are also referred to herein as "derivative-CP" and "derivative-RS" dependent upon whether the derivative is a product derived from a cyclic polyol or from a reduced saccharide starting material respectively.

Preferably the derivative-CP and derivative-RS contain 35% by weight tri or higher esters, e.g. at least 40%.

Preferably 35 to 85% most preferably 40 to 80%, even more preferably 45 to 75%, such as 45 to 70% of the hydroxyl groups in said cyclic polyol or in said reduced saccharide are esterified or etherified to produce the derivative-CP and derivative-RS respectively.

For the derivative-CP and derivative-RS, the tetra, penta etc. prefixes only indicate the average degrees of esterification or etherification. The compounds exist as a mixture of materials ranging from the monoester to the fully esterified ester. It is the average degree of esterification as determined by weight that is referred to herein.

The derivative-CP and derivative-RS used do not have substantial crystalline character at 20°C. Instead they are preferably in a liquid or soft solid state, as hereinbelow defined, at 20°C.

The starting cyclic polyol or reduced saccharide material is esterified or etherified with C₈-C₂₂ alkyl or alkenyl chains to the appropriate extent of esterification or etherification so that the derivatives are in the requisite liquid or soft solid state. These chains may contain unsaturation, branching or mixed chain lengths.

Typically the derivative-CP or derivative-RS has 3 or more, preferably

4 or more, for example 3 to 8, e.g. 3 to 5, ester or ether groups or mixtures thereof. It is preferred if two or more of the ester or ether groups of the derivative-CP and derivative-RS are independently of one another attached to a C₈ to C₂₂ alkyl or alkenyl chain. The alkyl or alkenyl groups may be branched or linear carbon chains.

In the context of the present invention the terms derivative-CP and derivative-RS encompass all ether or ester derivatives of all forms of saccharides, which fall into the above definition. Examples of preferred saccharides for the derivative-CP and derivative-RS to be derived from are monosaccharides and disaccharides.

Examples of monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose. Glucose is especially preferred. An example of a reduced saccharide is sorbitan. Examples of disaccharides include maltose, lactose, cellobiose and sucrose. Sucrose is especially preferred.

If the derivative-CP is based on a disaccharide it is preferred if the disaccharide has 3 or more ester or ether groups attached to it. Examples include sucrose tri, tetra and penta esters. Where the cyclic polyol is a reducing sugar it is advantageous if each ring of the derivative-CP has one ether group, preferably at the C-_. position. Suitable examples of such compounds include methyl glucose derivatives.

Examples of suitable derivative-CPs include esters of alkyl(poly)glucosides, in particular alkyl glucoside esters having a degree of polymerization from 1 to 2.

The HLB of the derivative-CP and derivative-RS is typically between 1 and 3.

The derivative-CP and derivative-RS may have branched or linear alkyl or alkenyl chains (with varying degrees of brandling), mixed chain lengths and/or unsaturation. Those having unsaturated and/or mixed alkyl chain lengths are preferred.

One or more of the alkyl or alkenyl chains (independently attached to the ester or ether groups) may contain at least one unsaturated bond.

For example, predominantly unsaturated fatty chains may be attached to the ester/ether groups, e.g. those attached may be derived from rape oil, cotton seed oil, soybean oil, oleic, tallow, palmitoleic, linoleic, erucic or other sources of unsaturated vegetable fatty acids.

The alkyl or alkenyl chains of the derivative-CP and derivative-RS are preferably predominantly unsaturated, for example sucrose tetratallowate, sucrose tetrarapeate, sucrose tetraoleate, sucrose tetraesters of soybean oil or cotton seed oil, cellobiose tetraoleate, sucrose trioleate, sucrose triapeate, sucrose pentaoleate, sucrose pentarapeate, sucrose hexaoleate, sucrose hexarapeate, sucrose triesters, pentaesters and hexaesters of soybean oil or cotton seed oil, glucose trioleate, glucose tetraoleate, xylose trioleate, or sucrose tetra-,tri-, penta- or hexa- esters with any mixture of predominantly unsaturated fatty acid chains.

However some derivative-CPs and derivative-RS s may be based on alkyl or alkenyl chains derived from polyunsaturated fatty acid sources, e.g. sucrose tetralinoleate. It is preferred that most, if not all, of the polyunsaturation has been removed by partial hydrogenation if such polyunsaturated fatty acid chains are used.

Oily sugar derivatives suitable for use in the compositions include sucrose pentalaurate, sucrose tetraoleate, sucrose pentaerucate, sucrose tetraerucate, and sucrose pentaoleate and the like. Suitable materials include some of the Ryoto series available from Mitsubishi Kagaku Foods Corporation, such as for example

Ryoto ER290.

The liquid or soft solid derivative-CPs and derivative-RS s are characterized as materials having a solid:liquid ratio of between 50:50 and 0:100 at 20°C as determined by T₂ relaxation time NMR, preferably between 43:57 and 0:100, most preferably between 40:60 and 0:100, such as, 20:80 and 0:100. The T₂ NMR relaxation time is commonly used for characterizing solid:liquid ratios in soft solid products such as fats and margarines. For the purpose of the present invention, any component of the NMR signal with a T of less than 100 microsecond is considered to be a solid component and any component with T₂ greater than 100 microseconds is considered to be a liquid component.

The liquid or soft solid derivative-CPE and derivative-RSE can be prepared by a variety of methods well known to those skilled in the art. These methods include acylation of the cyclic polyol or of a reduced saccharide with an acid chloride; trans-esterification of the cyclic polyol or of a reduced saccharide material with short chain fatty acid esters in the presence of a basic catalyst (e.g. KOH); acylation of the cyclic polyol or of a reduced saccharide with an acid anhydride, and, acylation of the cyclic polyol or of a reduced saccharide with a fatty acid. Typical preparations of these materials are disclosed in US 4 386 213 and AU 14416/88 (Procter and Gamble).

Preferably, the water insoluble oils used in the present invention are hydrophobia It is also preferred that the water insoluble oils be sugar ester oils or an oil with substantially no surface activity. It is preferred that if the water insoluble oil is an ester oil, that it be a sugar ester oil or a mineral oil. Suitable oils include those in the Sirius range of mineral oils (e.g., Silkolene). Suitable ester oils include the saturated ester oils (e.g., Unichema) and the unsaturated sugar ester oils (e.g., Mitsubishi Kagaku). It is preferred that the ester oils of the invention be hydrophobic. It is further preferred that the ester oil be saturated (i.e., hardened) in nature, unless it is a sugar ester oil or a plant derivative, in which case, unsaturation is preferred.

Suitable ester oils are the fatty ester of a mono or polyhydric alcohol having from 1 to about 24 carbon atoms in the hydrocarbon chain and mono or poly carboxylic acids having from 1 to about 24 carbon atoms in the hydrocarbon chain, with the proviso that the total number of carbon atoms in the ester oil is equal to or greater than 16 and that at least one of the hydrocarbon radicals in the ester oil has 12 or more carbon atoms. Ester oils most suitable for use in the present invention are the PRIOLUBES from Unichema. In particular, PRIOLUBE 1407, PRIOLUBE 1447, PRIOLUBE 1415, PRIOLUBE 1446, PRIOLUBE 1427, PRIOLUBE 1445, PRIOLUBE 2045, PRIOLUBE 3988, PRIOLUBE 3987, PRIOLUBE 2091, ESTOL 1545, and ESTOL 1527 are advantageously employed in the present invention. Of these, ESTOL 1545, which is a 2-ethyl hexyl stearate, is particularly useful. Suitable mineral oils include the Esso Marcol technical grade range of oils, such as the Silkolene medicinal Sirius range (e.g., M40, M70, and Ml 80). The molecular weight of the mineral oil is typically within the range 150 to 400.

It is preferred that the density of the mineral oil be from 0.80 to 0.90 g/cm², such as for example from 0.83 to 0.88 g/cm². The viscosity of the ester oil or mineral oil may be from 2 mPas to 400 mPas at a temperature of 25°C, preferably a viscosity from 2 mPas to 150 mPas, such as for example, a viscosity from 10 mPas to 100 mPas. The viscosity of the sugar ester oil should be below 50,000 mPas, preferably 5,000 mPas to 20,000 mPas, such as for example from 6,000 mPas to 20,000 mPas. All viscosities are measured at 25°C. It is further preferred that the refractive index of the oil be from 1.445 to 1.490, such as from 1.460 to 1.485. The fragrance composition of the present invention may be composed of aroma chemicals selected from one or more of the following classes: alcohols, aldehydes, ketones, esters, acetals, oximes, nitriles, ethers, and essential oils.

The fragrance delivery vehicle may optionally contain, viscosity modifiers, antioxidants, UV absorbers, non ionics, zwiterionics, dye transfer ingredients, enzymes, antimicrobial agents, cationic agents, antistatic agents, dyes, fatty acids, emulsifiers, shape retention agents, anti-wrinkling agents, color care agents, bluing agents, optical brighteners, preservatives, anti-corrosion agents, insect repellent agents, and mixtures thereof.

The fragrance delivery vehicle of the present invention (i.e., the water insoluble oil, cationic active, and fragrance composition) also serves to improve the fragrance perception of any consumer product to which it is added. For example a hair conditioner, fabric softener, etc. not only to provide enhanced fragrance and conditioning to a substrate-to-be-treated (e.g., hair or fabric), but also to improve the fragrance of the underlying consumer product. Thus, in the present invention, a fragrance-improving quantity of the fragrance delivery vehicle may be incorporated (i.e., mixed into, or combined with) any suitable consumer product.

Accordingly, another embodiment of the invention is a process for enhancing the fragrance of a consumer product. This process includes incorporating a fragrance improving quantity of the fragrance delivery vehicle of the invention into a consumer product.

In the present invention, a "fragrance-improving quantity" of the fragrance delivery vehicle corresponds to the amount of the fragrance delivery vehicle required to condition and impart a fragrance to a substrate. Thus, a fragrance- improving quantity of the fragrance delivery vehicle as used herein means from about 0.5 to about 25%) wt, preferably from about 1% to about 20%(wt), such as for example from about 5% to about 10%(wt) based on the weight of the consumer product.

As used herein, a consumer product includes any commercially available product to which the present fragrance delivery vehicles may be added, without significantly altering the underlying function of the consumer product. Thus, a consumer product includes for example, laundry detergents, laundry and hair conditioners, soaps, shampoos, face, hair, and body creams, fabric softeners, dewrinklers, cleansers, and the like.

The following examples are provided to further illustrate the processes and compositions of the present invention. These examples are illustrative only and are not intended to limit the scope of the invention in any way.

EXAMPLES

In the examples, all percent are %wt unless otherwise noted.

Example 1

For each fragrance delivery vehicle used (A, B, and C), desized Terry toweling was cut into four pieces and was washed in a Terg-O-Tometer using Purex commercial detergent at a cloth to liquid ratio of 1:15 at a product concentration of 2 g in 1050 millihters. Agitation was at 150 rpm for 15 minutes. Excess detergent liquid was removed. The towels were rinsed with water in the Terg-O-Tometer for 5 minutes. A further rinse was carried out containing 3.5g of the fragrance delivery vehicles set forth below (A, B, and C):

A B C Arquad 2HT (75%) 3.8 2.5 2.5

Mineral Oil 3.3 3.3 3.3

Fragrance 0.3 0.3 0.3

Where the fragrance in A and B is denoted Fa and the fragrance in C is denoted Fc below:

Fragrance Fa Fc CLogP Vapor

Pressure Gardenol 10 10 1.38 Luarine 10 10 1.54 Florol 10 10 2.0 Propyl Diantilis 10 10 2.34

Dihydroeugenol 10 ~ 2.71

DMBC acetate 10 ~ 3.0

Folione 10 3.56 0.09

Trans Decen-4-al 10 3.77 0.331

Gamma methyl ionone 10 10 4.25 0.003

Hexyl Salicylate 10 10 4.89 0.0005

Hexyl Cinnamic aldehyde 10 10 5.33 0.0005

Fixolide 10 10 6.37 0.0005

The towels were placed in a spin dryer for 15 seconds. Half the damp towels were used for assessment of fragrance intensity in the damp form and the other half were line dried for 24 hours.

The fragrance imparted to the damp (Damp) and dry (Dry) towelling was assessed by an expert panel of 5 individuals. The results of the panel determinations are set forth below:

Damp

A was significantly stronger than B C was significantly stronger than A

Dry 24 Hour

B was significantly stronger than A C was significantly stronger than A

Example 2

The following softener systems had l%(wt) of the fragrances shown below incorporated:

HEQ SPE HEQ 13.5 0.0 HEQ/SPE 6.5 6.5

Where HEQ is an ester quaternium compounds, dialkylyloxy dimethyl ammonium chloride, where the alky is hardened tallow. SPE is a Sucrose Poly Ester. In Examples 2-5, the SPE is Ryoto ER290.

The following Fragrances were prepared:

Part L

Aroma Chemical % CLogP MMHg

Phenyl Ethyl Alcohol 10.0 1.36 0.037

Cis-3-Hexanol 10.0 1.61 0.962

Dipropylene Glycol* 2.0 - -

* solvent

Part H

Aroma Chemical % CLogP MM Hg

Hexyl Cinnamic Aldehyde 10 5.33 0.00032

Galaxolide 10 5.95 0.00016

Iso-E Super 10 5.28 0.00203

Fixolide 10 6.37 0.00010

Dipropylene Glycol 5

Part M

Aroma Chemical % CLogP MM Hg

Rosalva 10 3.55 0.00734

Peonile 10 3.15 0.00027

Part X 10

Dipropylene glycol 3

Where

X is:

Aroma Chemical CLogP MM Hg

A: Rhubofix 3.31 0.00366

B: 1-Citronellol 2.38 0.01413

C: Fleuroxene 3.27 0.02913

D Jaservate 3.24 0.03974 Dihydrolinalool 3.32 0.08802

The fragrances were combined as follows:

Part L 22%

Part H 45%

Part M 33% The product was assessed for Odor Intensity by a panel of 5 trained panelists. The number in the Table indicates the number of panelist selecting the product with the strongest odor:

Desized Terry Toweling test cloths were pre-washed in 2.05g of Purex Free detergent liquid in tap water at 100°F in a Terg-O-Tometer. The cloth to liquor ratio was 1 :20. The towels were rinsed once in 2 liters of tap water. To the final rinse, 2.05 g of the respective softener was added and agitated for 5 minutes. The toweling pieces were spun dry.

The damp towels were assessed by a panel of 5 trained panelists for odor intensity as described above:

Thus, to restore the intensity of odor on damp fabric an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg was required.

Example 3

The following softener systems had 1% of the fragrances shown below incorporated:

HEQ SPE

HEQ 13.5 0.0

HEQ/SPE 6.5 6.5

The following Fragrances were prepared:

Part L

Aroma Chemical % CLogP MMHg

Phenyl Ethyl Alcohol 10.0 1.36 0.037

Cis-3-Hexanol 10.0 1.61 0.962

Dipropylene Glycol* 2.0 - -

* solvent

Part H

Aroma Chemical % CLogP MM Hg

Hexyl Cinnamic Aldehyde 10 5.33 0.00032

Galaxolide 10 5.95 0.00016

Iso-E Super 10 5.28 0.00203

Fixolide 10 6.37 0.00010

Dipropylene Glycol 5

Part M

Aroma Chemical % CLogP MM Hg

Rosalva 10 3.55 0.00734

Peonile 10 3.15 0.00027

Part 10

Dipropylene glycol 3 Where

X is:

Aroma Chemical CLogP MM Hg A* B C D E

Rliubofix 3.31 0.00366 10 9 8 7 5 Folione 3.56 0.09433 0 1 2 3 5 *The numbers under A, B, C, D, and E correspond to the ratio of Rubofix:Folione in each of the respective compositions.

The fragrances were combined as follows:

Part L 22%

Part H 45%

Part M 33%

The product was assessed for Odor Intensity by a panel of 5 trained panelists as described in Example 2:

The panelists then selected each composition by odor intensity as described in Example 2:

The improvement in fragrance intensity out of the bottle and on damp fabric can be seen by inclusion of a CLogP material of at least 3.56 and an vapor pressure of greater than 0.09 MM Hg.

Example 4

HEQ SPE

HEQ 13.5 0.0 HEQ/SPE 6.5 6.5

The following Fragrances were prepared:

Part L

Aroma Chemical % CLogP MMHg

Phenyl Ethyl Alcohol 10.0 1.36 0.037

Cis-3-Hexanol 10.0 1.61 0.962

Dipropylene Glycol* 2.0 - -

* solvent

Part H

Aroma Chemical % CLogP MM Hg

Hexyl Cinnamic Aldehyde 10 5.33 0.00032

Galaxolide 10 5.95 0.00016

Iso-E Super 10 5.28 0.00203

Fixolide 10 6.37 0.00010

Dipropylene Glycol 5

Part M

Aroma Chemical % CLogP MM Hg Rosalva 10 3.55 0.00734 Peonile 10 3.15 0.00027 Part X 10 Dipropylene glycol 3

Where

X is:

Aroma Chemical CLogP MM Hg A* B C D E

Rubofix 3.31 0.00366 10 9 8 7

Trans Decen-4-Al 3.77 1.2652 0 1 2 3

*The ratio of Rubofix:Trans Decen-4-Al in compositions A, B, C, D, and E is set forth in columns A, B, C, D, and E.

The fragrances were combined as follows:

Part L 22%

Part H 45%

Part M 33%

The product was assessed for Odor Intensity by a panel of 5 trained panelists as set forth in Example 2:

The panelists then selected each composition by odor intensity as set forth in Example 2:

These data confirm that low levels of the mid range clog P materials with a high vapor pressure and preferably a low perception threshold are required to maintain the odor perception in the delivery system of the present invention.

Example 5 The effect of CLogP of the fragrance materials on the delivery fragrance materials from a rinse solution in cationic only and cationic plus oil systems was investigated.

The following three compositions were prepared in demineralized water incorporating the fragrance RCLP2 shown below at 1%.

HEQ 13% HEQ

3:1 HEQ/SPE 9.75 HEQ + 3.25 SPE

1:1 HEQ/SPE 6.50 HEQ + 6.50 SPE

RCLP2

The following seven materials were mixed together in equal amounts:

% Aroma Chemical CLogP

14.3 Allyl Caproate 3.13

14.3 Linalool 3.30

14.3 Citronellol 3.38

14.3 Florhydral 3.72 14.3 n Hexyl Salicylate 4.89

14.3 Hexyl Cinnamic Aldehyde 5.33 14.3 Fixolide 6.37 The following wash conditions were used:

Desized Terry Toweling test cloths were pre-washed in 2.05g of Purex

Free detergent liquid in tap water at 100°F in a Terg-O-Tometer. The cloth to liquor ratio was 1 :20. The towels were rinsed once in 2 liters of tap water. To the final rinse, 2.05 g of the respective softener was added and agitated for 5 minutes. The toweling pieces were spun dry.

Half of the toweling pieces were extracted with methylene chloride in a Soxhlet apparatus for sufficient time to effect complete extraction of the target analytes. Half of the toweling pieces were analyzed by placing in appropriate headspace collection vessel and collecting sufficient headspace for instrumental analysis.

Both headspace and extracts were analyzed on an Agilent 6890 capillary GC fitted with a high sensitivity Mass Selective Detector.

The following amount of each aroma chemical deposited on the toweling pieces was as follows:

Aroma Chemical CLogP MM Hg HEQ 3:1 HEQ/SPE 1:1

HEQ/SPE

Ally caproate 3.13 0.48 0 30.9 321.4

Linalool 3.28 0.16 0 0 29.2

Citronellol 3.38 0.01 0 0 29.2

Florhydral 3.72 0.007 278.7 454.7 1206.5

Hexyl Salicylate 4.89 0.0008 7494.6 7609.0 9591.0

Hexyl Cinnamic Aid. 5.33 0.0003 14475.1 16347.0 22094.7

Fixolide 6.4 0.0001 18813.9 19202.0 22094.7

Total Ng/g fabric 41062.2 43643.7 49614.4 The date show that below 3.5 the amount of fragrance deposited is small, much larger amounts of the fragrance, however, are deposited with a CLogP >

4.0. Thus, in the fragrance composition the CLogP should be kept at as high a level as possible taking into account the need for some of the fragrance to perfume the product.

The invention being thus described, it will be obvious that the same may be varied in many ways. Such variations are not to be regarded as a departure from the spirit and scope of the invention and all such modifications are intended to be included within the scope of the following claims.

Claims

WHAT IS CLAIMED IS:

1. A process for conditioning and fragrancing a substrate comprising:

(a) providing a fragrance delivery vehicle comprising a water insoluble oil, a conditioner containing a cationic active at a level above 0.5%(wt), and at least 0.1%(wt) of a fragrance composition; and

(b) contacting the fragrance delivery vehicle with a substrate in an aqueous solution.

2. A process according to claim 1, wherein the cationic active is present in the fragrance delivery vehicle at a level above 1.0%(wt).

3. A process according to claim 1, wherein the water insoluble oil is present in the fragrance delivery vehicle at a level above 0.1%(wt).

4. A process according to claim 3, wherein the water insoluble oil is present in the fragrance delivery vehicle at a level above 0.5%(wt).

5. A process according to claim 1, wherein the water insoluble oil is selected from the group consisting of mineral oils, ester oils, sugar ester oils, natural oils, and mixtures thereof.

6. A process according to claim 5, wherein the water insoluble oils are hydrophobic with substantially no surface activity.

7. A process according to claim 5, wherein the natural oil is a vegetable oil.

8. A process according to claim 1, wherein the fragrance composition is present in the fragrance delivery vehicle at a level above 0.1 %(wι).

9. A process according to claim 8, wherein the fragrance composition is present in the fragrance delivery vehicle at a level 0.2%(wt).

10. A process according to claim 1, wherein the fragrance composition consists of at least 2%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 and a vapor pressure at 25°C of less than 0.02 mm Hg.

11. A process according to claim 10, wherein the aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 has a vapor pressure at 25°C of greater than 0.04 mm Hg.

12. A process according to claim 11, wherein the aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 has a vapor pressure

13. A process according to claim 10, wherein the aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 has a vapor pressure at 25°C of less than 0.01 mm Hg.

14. A process according to claim 13, wherein the aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 has a vapor pressure at 25°C of less than 0.008 mm Hg.

15. A process according to claim 10, wherein the aroma chemical or mixture of aroma chemicals has a perception threshold below 100 ng per liter at 25°C.

16. A process according to claim 15, wherein the aroma chemical or mixture of aroma chemicals has a perception threshold of 50 ng per liter at 25°C.

17. A process according to claim 16, wherein the aroma chemical or mixture of aroma chemicals has a perception threshold of below 30 ng per liter at

25°C.

18. A fragrance delivery vehicle comprising a water insoluble oil, a conditioner containing a cationic active, and at least 0.1%>(wt) of a fragrance composition consisting of at least 2 %(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%(wt) of an aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 and a vapor pressure at 25°C of less than 0.02 mm Hg.

19. A fragrance delivery vehicle according to claim 18, wherein the cationic active is present in the fragrance delivery vehicle at a level above 0.5%(wt).

20. A fragrance delivery vehicle according to claim 18, wherein the water insoluble oil is present in the fragrance delivery vehicle at a level above 0.1%(wt).

21. A fragrance delivery vehicle made by the process of combining a water insoluble oil, a conditioner containing a cationic active, and at least 0.1%(wt) of a fragrance composition consisting of at least 2%(wt) of an aroma chemical or mixture of aroma chemicals with a CLogP between 3.0 and 4.0 and a vapor pressure at 25°C of greater than 0.02 mm Hg and at least 25%>(wt) of an aroma chemical or mixture of aroma chemicals having a CLogP greater than 4.0 and a vapor pressure at 25°C of less than 0.02 mm Hg.

22. A process for enhancing the fragrance of a consumer product comprising:

(a) incorporating a fragrance improving quantity of the fragrance delivery vehicle of claim 18 into a consumer product.

23. A process according to claim 22 wherein the consumer product is selected from the group consisting of laundry detergents, laundry conditioners, hair conditioners, soaps, shampoos, face creams, hair creams, body creams, fabric softeners, dewrinklers, and cleansers.