GB2546519A - Improvements in or relating to organic compounds - Google Patents

Abstract

(I) Use of a compound of formula (I) as a perfume potentiator compound in perfume composition is provided. Preferably the perfume composition is encapsulated in a core-shell microcapsule, in particular, an aminoplast microcapsule or a starch microcapsule. A perfume composition comprising a compound of formula (I) as a perfume potentiator; a method of potentiating the performance of a perfume composition by admixing to the perfume composition a compound of formula (I); and a method of potentiating the performance of an encapsulated perfume composition by admixing a compound according to formula (I) to a perfume composition that will be encapsulated are also provided.

Description

Improvements in or relating to organic compounds Field of the Invention

This invention relates to the use of 3-(4-isobutyl-2-methylphenyl)propanal as a perfume potentiator compound in a perfume composition containing 3-(4-isobutyl- 2- methylphenyl)propanal and at least one additional perfume ingredient. The invention further relates to perfume compositions containing said perfume potentiator compound, as well as to consumer products containing said perfume compositions.

Background to the Invention 3- (4-isobutyl-2-methylphenyl)propanal and its use in perfumery, particularly as a replacer for Lilial ™, is disclosed in WO2014180945.

Lilial ™ has been shown to exhibit toxic effects on the reproductive organs of male rats and dogs, and under the Global Harmonized System (GHS) classification system it is classified as a CMR2 material. Given that it is necessary to establish that CMR category 2 materials are harmless to humans in the quantities proposed for use, it is increasingly likely that Lilial ™ usage levels of the material will dwindle in the future.

The muguet odour characteristics of 3-(4-isobutyl-2-methylphenyl)propanal are remarkably reminiscent of Lilial ™, and as such it has been proposed as a substitute in both fine perfumery and technical perfumery.

However, when the level of Lilial ™ in a perfume composition is reduced or eliminated altogether the applicant found that not only is the odour profile of the perfume composition changed, but the performance of the perfume composition is diminished too, and particularly so when the perfume composition is in encapsulated form. More particularly, trained perfumers remark that perfume compositions containing no Lilial ™ or containing substantially reduced levels of Lilial ™ are physically less performing. More particularly still, they are considered to be less impactful, possess less volume, or are lacking in some other related olfactory attribute.

Furthermore, although Lilial ™ substitutes described in the literature (see for example, W02010/105873, W02009/027957 and W02013/045301) are described as being able to mimic the olfactive character of Lilial ™, the performance of these Lilial ™ - free perfume compositions is affected adversely.

There remains a need to provide perfume compositions that are reduced in Lilial ™ or are Lilial ™-free, which nevertheless possess substantially the same odour characteristics of Lilial ™-containing perfume compositions, and which are also as performant as Lilial ™-containing perfume compositions, particularly when those compositions are in encapsulated form.

Surprisingly it was found that 3-(4-isobutyl-2-methylphenyl)propanal, in addition to its ability to reproduce the odour characteristics of Lilial ™, is also able to potentiate the performance of Lilial ™ - free perfume compositions.

Summary of the Invention

The present invention addresses the deficiencies in the prior art and provides in a first aspect the use of 3-(4-isobutyl-2-methylphenyl)propanal as a perfume potentiator compound in a perfume composition containing at least one additional perfumery ingredient.

The present invention also relates to a perfume composition comprising a perfume composition potentiating amount of 3-(4-isobutyl-2-methylphenyl)propanal.

The present invention further relates to a consumer product containing said perfume composition.

Detailed description of the Invention

As used herein, the term "perfume potentiator compound" as it relates to 3-(4-isobutyl-2-methylphenyl)propanal refers to the use of this compound to enhance the olfactory attributes of a perfume composition in which it is incorporated. Olfactory attributes are diverse and include perfumery descriptors such as intensity or impact, volume, bloom, coherence and the like.

The impact or intensity of a perfume composition is a function of Odour Detection Threshold and Vapour Pressure, which are both well-known parameters in the field of perfumery. "Volume" is likewise a term of art well known to the skilled perfumer, and relates to the impact or intensity of a perfume composition at a defined distance from its source. The ability of a perfume to be recognised in a space some distance from its source is an important characteristic of a perfume.

The assessment of a perfume composition at distance from a source is typically evaluated in a smelling booth, which measures the ability of an odour to fill a space defined by the booth. This enables a quantitative assessment of the amount of perfume composition which has accumulated in a booth between the moment when the perfume composition was delivered to the booth and the moment of its detection or observation.

An attribute or parameter related to the spatio-temporal olfactory profile of perfume compositions is its so-called "bloom". Bloom refers to the build-up in perfume intensity and volume that is experienced upon dissolution of a perfume composition in use. This can be either an instantaneous "burst" of perfume, for example after applying shampoo in the shower, or a more diffusive bloom that is noticed while hand-washing dishes or clothes. This parameter or attribute can likewise be measured in a smelling booth. A perfume composition's so-called "coherence" is another of its olfactive attributes. A perfume composition will be understood to deliver a coherent olfactory impact if its component ingredients are perceived within a period of time at some distance from the source in such a way that the olfactory characteristics of the impact will be homogeneous and remain qualitatively substantially unchanged as time evolves. In contrast, a perfume composition exhibits an incoherent olfactory impact when it is characterized by successive smells having different olfactory characteristics. For example, a fragrance composition having an incoherent olfactory impact may develop in a first step a powdery smell, followed by a floral smell and evolving step by step until it becomes perceived as a full perfume.

The olfactory performance of a perfume composition containing 3-(4-isobutyl-2-methylphenyl)propanal can at least match, or even exceed, the performance of similar perfume compositions containing Lilial ™ in at least one of the olfactory attributes referred to herein above.

As stated herein above, the perfume composition contains at least one perfume ingredient in addition to 3-(4-isobutyl-2-methylphenyl)propanal.

The nature and type of these perfuming co-ingredients do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to the nature of the product to be perfumed and the desired olfactory effect. In general terms, however, these perfuming co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compounds and essential oils of natural or synthetic origin. Many of these ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, N.J., USA, or its more recent versions, or in other works of a similar nature, such as Leffingwell or thegoodscentcompany.com website, as well as in the abundant patent literature covering the art of perfumery.

Similarly, a detailed description of the nature and type of solvents commonly used in perfuming compositions cannot be exhaustive. A skilled person is able to select them on the basis of the nature of the product to be perfumed. However, as nonlimiting examples of such solvents, one can cite dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate as well as ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar ™ or glycol ethers and glycol ether esters such as those known under the trademark Dowanol ™.

In a particular embodiment of the invention, the perfume co-ingredients include ingredients which provide a muguet accord, or are commonly used in perfumes having muguet characteristics.

Particular perfume ingredients include, but are not limited to (E/Z)-9-hydroxy-5,9-dimethyldec-4-enal, 3-(2-isobutyl-4-methylphenyl)propanal, 6-methoxy-2,6-dimethylheptan-l-al (methoxymelonal), 5,9-di methyl-4,8-decadienal (geraldehyde), beta-methyl-3-(l-methylethyl)benzenepropanal (Florhydral), octahydro-8,8-dimethylnaphthalene-2-carbaldehyde (Cyclomyral), alpha-methyl-1,3-benzodioxole-5-propionaldehyde (helional), 5-methyl-2-(l-methylbutyl)-5-propyl-l,3-dioxan (Troenan), 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde (Floralozone), farnesol, 3,7,ll-trimethyldodeca-l,6,10-trien-3-ol, optionally as an isomeric mixture (nerolidol), 2-methyl-4-phenylbutan-2-ol (dimethylphenylethylcarbinol), cis-4-(isopropyl)cyclohexanemethanol (Mayol), 1-(l-hydroxyethyl)-4-(l-methylethyl)cyclohexane (optionally as a mixture of the diastereoisomers) (mugetanol), (4-methyl-3-pentenyl)cyclohexenecarbaldehyde (Citrusal), cyclohexyl salicylate, hexyl salicylate, benzyl salicylate, amyl salicylate, 3- (p-(2-methylpropyl)phenyl)-2-methylpropionaldehyde (Silvial), 3-p-cumenyl-2-methylpropionaldehyde (cyclamenaldehyde), mixtures of: cis-tetrahydro-2-isobutyl- 4- methylpyran-4-ol; trans-tetrahydro-2-isobutyl-4-methylpyran-4-ol; (Floral), triethyl citrate and dipropylene glycol.

Said perfume ingredients may additionally include Amyl Salicylate (2050-08-0 ); Aurantiol ® (89-43-0); Benzyl Salicylate (118-58-1); Cis-3-hexenyl Salicylate (65405-77-8); Citronellyl Oxyacetaldehyde (7492-67-3); Cyclemax (7775-00-0); Cyclohexyl Salicylate (25485-88-5); Cyclomyral ® (68738-94-3); Citronellol (106-22-9); Geraniol (106-24-1); Cyclopentol He 937165 (84560-00-9); Cymal (103-95-7); Dupical (30168-23-1); Ethyl Linalool (10339-55-6); Floral Super (71077-31-1); Florhydral ® (125109-85-5); Floral ® (63500-71-0 ); Gyrane (24237-00-1); Hexyl Salicylate (6259-76-3); Helional (TM) (1205-17-0); Hydroxycitronellal (107-75-5); Linalool (78-70-6); Lyral ® (31906-04-4); Majantol ® (103694-68-4); Mayol ® (13828-37-0); Melafleur (68991-97-9); Melonal (106-72-9); Mugetanol (63767-86-2); Muguesia (56836-93-2); Muguet alcohol (13351-61-6); Verdantiol (91-51-0); Peonile ® (10461-98-0); Phenoxanol ® (55066-48-3); Rossitol ® (215231-33-7); Silvial ® (6658-48-6); Suzural (6658-48-6); Muguol ® (18479-57-7); Tetrahydro Linalol (78-69-3 ); Acalea (84697-09-6); Dihydro Iso Jasmonate (37172-53-5); Hexyl Cinnamic Aldehyde (101-86-0); Hedione ® (24851-98-7); Acetoin (513-86- 0) ; Adoxal (141-13-9); Aldolone ® (207228-93-1); Ambrocenide ® (211299-54-6); Ambroxan (3738-00-9); Azurone ® (362467-67-2); Bacdanol ® (28219-61-6); Calone 1951 ® (28940-11-6); Cetalox ® (3738-00-9); Cinnamic alcohol (104-54- 1) ; Citral (5392-40-5); Cyclabute (67634-20-2); Cyclacet (TM) (5413-60-5); Cyclaprop ™ (17511-60-3); Cyclohexadecanolide (109-29-5 ); Cyclohexadecenone (3100-36-5); Cyclopentadecanone (507-72-7); Delta Damascone (57378-68-4 ); Ebanol ® (67801-20-1); Elintaal Forte (40910-49-4); Ethyl Vanillin (121-32-4); Ethylene Brassylate (105-95-3); Exaltenone 942008 (14595-54-1); Exaltolide Total 935985 (106-02-5); Floralozone (67634-14-4); Fructalate (72903-27-6); Gamma

Decalactone (706-14-9); Habanolide (111879-80-2); Helvetolide ® (141773-73-1); Hexamethylindanopyran (1222-05-5); Hydroxyambran ® (118562-73-5); Iso E Super ® (54464-57-2); Iso Hexenyl Cyclohexenyl Carboxaldehyde (37677-14-8); Jasmal (18871-14-2); Javanol ® (198404-98-7); Laurie Aldehyde (112-54-9); Mefranal (55066-49-4); Muscenone (63314-79-4); Tonalid ® (1506-02-1); Nectaryl ® (95962-14-4); Norlim Banol (70788-30-6); Para Hydroxy Phenyl Butanone (5471-51-2 ); Pino Acetaldehyde (33885-51-7); Romandolide ® (236391-76-7); Sanjinol (28219-61-6); Silvanone ® Supra (109-29- 5/507-72-7); Terpineol (8000-41-7); Vanillin (121-33-5); and Velvione ® (37609-25-9), wherein, the figures in parentheses are CAS numbers.

Whereas certain perfume ingredients recited herein above are referred to in terms of their trade names, perfume compositions of the present invention are not limited to proprietary perfume ingredients, and reference to a perfume ingredient by its trade name is also a reference to the generic molecule, which it embodies. The skilled person would immediately recognise the relationship between the trade name and the generic molecule known by its more formal chemical nomenclature, such as IUPAC nomenclature, or the relationship could be easily found with reference to common perfumery reference works such as Arctander, Leffingwell and thegoodscentcompany.com (.supra).

In an embodiment of the invention the perfume composition will contain at least 10 wt % of perfume ingredients having a ClogP of at least 2.0 and at least 30 wt % of perfume ingredients having a ClogP of at least 4.0. ClogP refers to the calculated octanol/water partitioning coefficient (P) of fragrance ingredients, which is giving the ratio between its equilibrium concentrations in octanol and in water.

The proportions in which 3-(4-isobutyl-2-methylphenyl)propanal can be incorporated into perfume composition of the present invention, will depend on the nature of the other perfumery co-ingredients, and on the olfactory effect sought, namely the intensity, volume, bloom or coherence of the perfume composition in which it is incorporated. Applicant found, however, that 3-(4-isobutyl-2-methylphenyl)propanal can replace Lilial ™ in terms of providing both the olfactive character of Lilial ™ as well as providing a potentiating effect with 0.5 dose equivalent of Lilial ™ or less. The benefit in using a lower dosage equivalent of 3-(4-isobutyl-2-methylphenyl)propanal to provide a potentiating effect to perfume compositions in the absence of Lilial ™ will be immediately apparent to the skilled addressee. The use of relative low levels of (4-isobutyl-2-methylphenyl)propanal means that it can provide its potentiating effect without overpowering the perfume composition with it olfactory character, allowing a potentiating effect to be achieved whilst maintaining a harmonious scent impression.

Typical dosage levels of Lilial ™ in a perfume composition may be from 1 to 30 wt % based on the total weight of the perfume composition. Accordingly, in a particular embodiment of the present invention a potentiating amount of 3-(4-isobutyl-2-methylphenyl)propanal is from 0.1 to 20 wt %, and more particularly from 0.1 to 15 wt %, and still more particularly 0.1 to 10 wt %, and even more particularly from 1 to 5 wt % based on the total weight of the perfume composition

In an embodiment of the invention, 3-(4-isobutyl-2-methylphenyl)propanal is used in a perfume composition that is in encapsulated form.

It is known to encapsulate perfume compositions. Perfume encapsulation is the process of isolating droplets of perfume oil within protective polymers in order to protect the perfume from evaporation, reaction, oxidation or otherwise dissipating prior to use. In general, the encapsulation may provide core shell or a matrix encapsulates. Suitable polymers for use in encapsulated perfume compositions of the present invention include vinyl polymer; an acrylate polymer, melamine-formaldehyde, urea formaldehyde and mixtures thereof. The common encapsulates are based on aminoplasts, starch, polyuria or polyurethane. Encapsulation and methods of encapsulation are well known in the art and do not warrant a more detailed description here, which in any case would not be exhaustive.

The perfume compositions containing 3-(4-isobutyl-2-methylphenyl)propanal according to the invention are suitable for use in fine perfumery articles, such as in perfumes, colognes or after-shave lotions, as well as in other current uses in functional perfumery articles such as perfumed soaps, shower or bath gels, hygiene products, or hair care products such as shampoos or conditioners, body deodorants and air fresheners or cosmetic preparations, in order to impart an intensity, roundness, richness and substantivity to said fine and functional articles.

The perfuming compositions according to the invention can also be used in articles such as liquid or solid detergents for textile treatment, fabric softeners, or also in detergent compositions or cleaning products for cleaning dishes or varied surfaces, for industrial or household use.

Said fine or functional perfumery articles are also referenced as perfumed articles.

There now follows a series of examples that serve to further illustrate the invention.

Example 1:

Lilial replacement in aminoplast capsules

Fabric softener A comprising 0.5% by weight of slurry of encapsulated perfume composition in aminoplast capsules was evaluated. Cotton terry towels were washed in a European washing machine. The olfactive impression was evaluated in a blind test by three trained persons on a scale from 1 to 5 at different stages. The results are set out in Table 1.

Table 1

Reference A: Proprietary perfume composition comprising X wt % Lilial™

Composition B: Reference A with Lilial™ removed

Composition C: Composition B containing 3-(4-isobutyl-2-methyl phenyl)

propanal @ 0.5 X amount of Lilial™ in Reference A

Composition D: Composition B containing 3-(4-isobutyl-2-methyl-

phenyl)propanal @ 0.1 X amount of Lilial™ in Reference A

Composition E: Composition B with a prior art Lilial™ replacer dosed at iso

concentration with Lilial™ used in Reference A

The olfactive impression of neat products and wet samples is usually dominated by the free fragrance composition, and only slightly affected by the encapsulated

fragrance composition, and no strong effect was expected. For the dry samples, the pre rub assessment is influenced by the remaining free fragrance composition and eventually by leaking encapsulated fragrance composition. The effect of the encapsulated fragrance composition can be determined in the assessment of the dry sample in post rub: the capsules deposited on the surface are breaking under pressure and the encapsulated fragrance composition is released.

The olfactive impression was assessed via a reference perfume composition containing Lilial™ (Reference A). If Lilial is removed (Composition B) and no replacer is added, the odour characteristics are changed, but also the volume of the perfume composition is lost. If Lilial™ is replaced by 3-(4-isobutyl-2-methylphenyl)propanal (in 50% and 10% of the original Lilial™ quantity, Compositions C and D respectively), samples close to the reference can be obtained, and no loss of volume occurs. If Lilial™ is replaced by a mixture of molecules that can olfactively mimic Lilial™ (Composition E), also a loss of volume takes place.

Example 2:

Lilial replacement in aminoplast capsules

Fabric softener B comprising 0.5% by weight of slurry of encapsulated perfume composition in aminoplast capsules was evaluated. Cotton terry towels were washed in a European washing machine. The olfactive impression was evaluated in a blind test by three trained persons on a scale from 1 to 5 at different stages. The results are presented in Table 2.

Table 2:

At similar dosages, 3-(4-isobutyl-2-methylphenyl)propanal imparts better performance than Lilial ™ at all stages (entries 1 and 2). At 50% of Lilial ™ dosage, 3-(4-isobutyl-2-methylphenyl)propanal performs well, in particular on dry sample in post rub.

Example 3:

Lilial replacement starch capsules 0.3% of starch capsules containing a perfume accord were incorporated in an powder detergent. 5g of perfumed powder detergent were diluted into 5L of warm water. Olfactive comments are done on the bloom smelt during the dilution of the

detergent powder into the water, by a panel of 4 trained persons giving qualitative description in comparison to the sample comprising Lilial ™. The results are set out in Table 3. Table 3:

IPM: Isopropyl myristate

In both accords it was found that samples with Lilial ™ or 3-(4-isobutyl-2-methylphenyl)propanal tend to round the accord, respectively. Samples with 3-(4-isobutyl-2-methylphenyl)propanal are even preferred and perceived more powerful while the dosage of the replacer is decreased by 2. In contrast, samples with IPM only are perceived as aggressive, not well balanced, and tending to be harsh.

Claims (9)

1. Claims:

   1. Use of a compound according to the formula (I)

   as a perfume potentiator compound in perfume compositions.
2. 2. Use of a compound according to claim 1, wherein the perfume composition is encapsulated.
3. 3. Use of a compound according to claim 1 or 2, wherein the perfume composition is encapsulated in a core-shell microcapsule.
4. 4. Use of a compound according to claim 3, wherein the core-shell microcapsule is an aminoplast microcapsule.
5. 5. Use of a compound according to claim 3, wherein the core-shell microcapsule is a starch microcapsule.
6. 6. A perfume composition comprising a compound according to the formula (I)

   as a perfume potentiator compound.
7. 7. The perfume composition according to claim 6, wherein the perfume composition is encapsulated.
8. 8. A method of potentiating the performance of a perfume composition by admixing to the perfume composition a compound according to the formula (I)
9. 9. A method of potentiating the performance of an encapsulated perfume composition by admixing a compound according to the formula (I)

   to a perfume composition that will be encapsulated.