Fragrance compositions
Abstract
A composition comprising: (a) a fragrance oil comprising: (i) perfume raw material, or mixture of perfume raw materials, of high note with a lower boiling point, or equal, at 250 ° C to 101 kPa (1 pressure atmosphere); (ii) perfume raw material, or mixture of perfume raw materials, of medium or low notes with a boiling point above 250 ° C at 101 kPa (1 pressure atmosphere); (b) a trapping material that is selected from the group consisting of capsules, microcapsules and nanocapsules; liposomes; perfume precursors selected from more than 1 type of chemical precursors; absorbents; cyclic oligosaccharides and mixtures thereof; (c) more than 50% volatile solvent having a vapor pressure of 2 kPa or greater than 25 ° C; wherein the weight ratio between high grade perfume raw materials and medium or low perfume perfume raw materials within the fragrance oil is in the range of 1:20 to 20: 1.
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Projected expiry passed 1 June 2021, 5.3 years ago.
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24 claims: 5 independent, 19 dependent
- 1ES 2 294 007 T3 REIVINDICACIONES 1. Una composición que comprende:(a) un aceite de fragancia que comprende: (i) materia prima de perfume, o mezcla de materias primas de perfume, de nota alta con un punto de ebullición inferior, o igual, a 250°C a 101 kPa (1 atmósfera de presión);(ii) materia prima de perfume, o mezcla de materias primas de perfume, de notas media o baja con un punto de ebullición superior a 250°C a 101 kPa (1 atmósfera de presión);(b) un material de atrapamiento que se selecciona del grupo que consiste en cápsulas, microcápsulas y nanocápsulas;liposomas;precursores de perfume seleccionados de más de 1 tipo de precursores de sustancia química;absorbentes;oligosacáridos cíclicos y mezclas de los mismos;(c) más de 50% de disolvente volátil que tiene una presión de vapor de 2 kPa o superior a 25°C;en donde la relación de peso entre las materias primas de perfume de nota alta y las materias primas de perfume de notas media o baja dentro del aceite de fragancia está en el intervalo de 1:20 a 20:1.
- 2Una composición según la reivindicación 1, en la que la relación de peso entre materias primas de perfume de nota alta y materias primas de perfume de notas media o baja dentro del aceite de fragancia está en el intervalo de 1:10 a 10:1, más preferiblemente de 8:1 a 1:2 y aún más preferiblemente es 1,2:1 a 1:1,2.
- 3Una composición según la reivindicación 1 ó 2, en la que la composición comprende de 0,01% a 99%, preferiblemente de 0,25% a 50%, más preferiblemente de 0,5% a 40%, aún más preferiblemente de 1% a 25% y con máxima preferencia de 2,5% a 25%, en peso, del aceite de fragancia.
- 4Una composición según cualquiera de las reivindicaciones 1 a 3, en la que las materias primas de perfume de nota alta se seleccionan de aldehídos con una masa molecular relativa inferior o igual a 200, ésteres con una masa molecular relativa inferior o igual a 225, terpenos con una masa molecular relativa inferior o igual a 200, alcoholes con una masa molecular relativa inferior o igual a 200, cetonas con una masa molecular relativa inferior o igual a 200, nitrilos, piracinas y mezclas de los mismos.
- 5Una composición según cualquiera de las reivindicaciones 1 a 4, en la que el aceite de fragancia comprende de 5% a 99%, preferiblemente de 5% a 70%, más preferiblemente de 10% a 60%, y aún más preferiblemente de 25% a 60%, en peso del aceite de fragancia, de materias primas de perfume de nota alta.
- 6Una composición según cualquiera de las reivindicaciones 1 a 5, en la que el aceite de fragancia comprende de 0,01% a 95%, preferiblemente de 5% a 85%, más preferiblemente de 10% a 60%, en peso de aceite de fragancia, de las materias primas de perfume de notas media y baja.
- 7Una composición según cualquiera de las reivindicaciones 1 a 6, en la que las materias primas de perfume de nota alta del aceite de fragancia comprenden 5% o más, en peso, de las materias primas de perfume de nota alta, en donde las materias primas de perfume de nota alta tienen un umbral de detección de olor de menos de, o igual a, 50 partes por mil millones, preferiblemente menos de, o igual a, 10 partes por mil millones.
- 8Una composición según cualquiera de las reivindicaciones 1 a 7, en la que las materias primas de perfume de nota media o baja del aceite de fragancia comprenden 10% o más, más preferiblemente 20% o más y con máxima preferencia 50% o más, en peso, de las materias primas de perfume de notas media y baja, en donde las materias primas de perfume de notas media o baja tienen un umbral de detección de olor de menos de, o igual a, 50 partes por mil millones, preferiblemente de menos de 10 partes por mil millones.
- 9Una composición según cualquiera de las reivindicaciones 1 a 8, en la que el material de atrapamiento se selecciona del grupo que consiste en precursores de perfume seleccionados de más de 1 tipo de sustancia química precursora;absorbentes;oligosacáridos cíclicos y mezclas de los mismos.
- 10Una composición según cualquiera de las reivindicaciones 1 a 9, en la que el material de atrapamiento se selecciona de oligosacáridos cíclicos.
- 11Una composición según cualquiera de las reivindicaciones 1 a 10, en la que el oligosacárido cíclico tiene seis, siete u ocho unidades sacárido y mezclas del mismo, preferiblemente seis o siete unidades sacárido y más preferiblemente siete unidades sacárido.
- 12Una composición según cualquiera de las reivindicaciones 1 a 11, en la que el oligosacárido cíclico es una ciclodextrina. ES 2 294 007 T3
- 13Una composición según cualquiera de las reivindicaciones 1 a 12, en la que el oligosacárido cíclico está sustituido con un sustituyente seleccionado de grupos alquilo o hidroxialquilo Ci -C 8 y mezclas de los mismos, preferiblemente grupos alquilo o hidroxialquilo C 1 -C 4 y mezclas de los mismos.
- 14Una composición según cualquiera de las reivindicaciones 1 a 13, en la que dicho oligosacárido cíclico está preferiblemente sustituido con grupos alquilo C 1 -C 4 y más preferiblemente sustituido con metilo.
- 15Una composición según cualquiera de las reivindicaciones 1 a 14, en la que dicho oligosacárido cíclico es aciclodextrina, β-ciclodextrina, metil-a-ciclodextrina, metil-e-ciclodextrina o mezclas de las mismas.
- 16Una composición según cualquiera de las reivindicaciones 1 a 15, en la que el oligosacárido cíclico es metil-βciclodextrina.
- 17Una composición según cualquiera de las reivindicaciones 1 a 16, que comprende de 0,1% a 95%, más preferiblemente de 0,5% a 50%, aún más preferiblemente de 1% a 25% y con máxima preferencia de 2% a 8%, en peso, de dicho material de atrapamiento.
- 18Una composición según cualquiera de las reivindicaciones 1 a 17, en la que el disolvente volátil tiene un punto de ebullición a 101 kPa (1 atmósfera de presión) de menos de 150°C, más preferiblemente menos de 100°C, aún más preferiblemente menos de 90°C, aún más preferiblemente todavía de menos de 80°C.
- 19Una composición según cualquiera de las reivindicaciones 1 a 18, en la que el disolvente volátil se selecciona de éteres, alcoholes y dioles de cadena lineal o ramificada, siliconas volátiles, propelentes y mezclas de los mismos;preferiblemente se selecciona de alcoholes C 1 -C 4 de cadena lineal o ramificada.
- 20Una composición según cualquiera de las reivindicaciones 1 a 19, en la que el disolvente volátil es etanol.
- 21Una composición según cualquiera de las reivindicaciones 1 a 20, que comprende de 55% a 99,9%, preferiblemente de 60% a 95%, más preferiblemente de 65% a 75%, en peso, de disolvente volátil.
- 22Una composición según cualquiera de las reivindicaciones 1 a 21, en la que la composición es una composición cosmética, preferiblemente una composición de fragancia.
- 23Un método de aplicación de una fragancia a un sustrato que comprende:(i) aplicar una composición según cualquiera de las reivindicaciones 1 a 22 a dicho sustrato;y preferiblemente (ii) dejar secar dicha composición.
- 24Uso de una composición según cualquiera de las reivindicaciones 1 a 22 para proporcionar un carácter de nota alta a un sustrato durante al menos 2 horas, preferiblemente durante al menos 4 horas, más preferiblemente durante al menos 6 horas.
Independent claims24
198 paragraphs in 8 sections, as filed
ES 2 294 007 T3
DESCRIPTION
Fragrance compositions.
Field of the invention
The present invention relates to compositions, in particular to cosmetic compositions and more especially to fragrance compositions, comprising a fragrance oil, an entrapment material and more than 50% volatile solvent, wherein the fragrance oil comprises both perfume raw materials of "high note" as of "middle and low note", wherein the weight ratio between both types of fragrance raw materials is in the range of about 1:20 to about 20: 1. More especially this invention relates to cosmetic compositions in which the fragrance character of the "top note" perfume raw materials remains detectable on the substrate for at least 2 hours after application. The compositions of the present invention are suitable for application to a wide variety of substrates but especially to the skin and hair.
Background of the invention
It has long been a feature of many types of compositions, including cosmetic compositions, that they comprise a fragrance oil in order to provide a pleasant odor. This can improve overall consumer acceptance of the composition or mask unpleasant odors. In fact, the sole purpose of some compositions may be to convey a pleasant odor to the skin, hair, or other suitable substrate.
Fragrance oils used in cosmetic compositions usually comprise many different perfume raw materials. Each perfume raw material used differs from the others by several important properties including individual character, volatility, and level of olfactory detection (known as the odor detection threshold). Taking into account these different properties, and others, the perfume raw material can be blended to develop a fragrance oil with an overall specific character profile. Character is typically designed to change and evolve over time as different perfume raw materials evaporate from the substrate and are detected by the user. For example, perfume raw materials that have high volatility and low persistence are commonly used to give an initial burst of characters, such as light, fresh, fruity, citrus, vegetal or delicate floral, to the fragrance oil and are detected shortly after application. These types of materials are usually called "top notes" in the fragrance field. In contrast, less volatile and more persistent perfume raw materials are typically used to provide a character such as musky, sweet, balsamic, spicy, woody, or intense floral to the fragrance oil which, although may be detected shortly after the application, also persists longer. These materials are commonly referred to as "middle notes" or "base notes." Very experienced perfume specialists are usually tasked with carefully blending the perfume raw materials so that the resulting fragrance oils have the desired overall fragrance character profile.
To date, the physical characteristics of the perfume raw materials themselves have limited the overall fragrance character profiles that can be created by perfumery experts. One of these limitations is that it has only been possible to develop fragrance oils that impart a "top note" character for a short period of time. This is because high note perfume raw materials are very volatile and therefore quickly release from the substrate. As such, the element of a longer lasting fragrance character profile has been achieved by utilizing middle and base notes, which in turn limit the achievable characters of musky, sweet, balsamic, spicy, woody or intense floral and the like. . Incorporating larger amounts of high note perfume raw materials into a fragrance oil does not enhance the long-lasting nature of the light, fresh, fruity, citrus, vegetable, or delicate floral "top note" fragrance character, but instead it could produce a stronger initial burst that would again evaporate quickly and therefore not last.
Consumer preference for fragrance compositions is known to be primarily driven by the initial "top note" character. It is therefore desirable to have a fragrance in which the "top note" character is long-lasting and perceived throughout use (ie, after application of the composition to the substrate). It is, therefore, also desirable to be able to create new profiles in the world of fragrance character profiles, in which one or more well-recognized "high note" characters remain over time so as to create a unique long-lasting "high, middle and low note" character. As such, it would be advantageous to be able to create a fragrance oil that would convey, in a new way, high note fragrance characteristics to a composition in which the top note character is released from the composition for a significant period of time and, in turn, particularly where the high note fragrance character remains detectable for at least two hours after application.
Many attempts have been made in the past to retard the volatility profiles of fragrance oils in many types of compositions and thereby enhance the overall fragrance effect. For example, the fragrance oil can be formulated to include a higher proportion of perfume raw materials with low volatility, which are consequently more persistent on the substrate. However, as stated above, this restricts the fragrance character that can be achieved over time. Another method has been to chemically and reversibly modify the perfume raw materials to obtain a perfume precursor compound which is described in WO 98/47477; WO 99/43667; WO 98/07405 and WO 98/47478. Perfume precursors are not themselves
ES 2 294 007 T3 volatile but, after the chemical modification is reversed, usually by hydrolysis when applied to the substrate, the perfume raw material is released and can then be evaporated in the usual way. In these examples, the release rate of the perfume raw materials is controlled by the reaction rate for the transformation of the perfume precursor into the perfume raw material.
A number of other methods have been discussed to improve the overall longevity of a fragrance by delaying the evaporation of fragrance oils. A wide variety of techniques have been described, including encapsulation of perfume raw materials, for example, within capsules (described in JP-A-58/052211, EP-A-303,461), absorption of materials to a surface, using for example carbon or zeolite (described in US-6,033,679) limiting by occlusion the release of perfume raw materials, for example, by forming a film (described in US-3,939,099) and complexing perfume raw materials, for example, with cyclic oligosaccharides. The state of the art of this last method includes patents JP-A-6/287127 and JP-A-8/176587, which describe the use of hydroxyalkylated cyclodextrins in cosmetic compositions to maintain the effect of fragrance, and JP-A -8/183719 and JP-A-10/120541, which describe a combination of fragrance encapsulated in cyclodextrin and fragrance not encapsulated within a deodorant composition to extend the duration of the fragrance to at least 2 hours. WO 00/67714 A (PROCTER & GAMBLE) describes a cosmetic vaporizer (Examples I-III) comprising:
- a: 10-15% of a fragrance
- b: 5-10% cyclic oligosaccharide
- c: 70% ethanol.
Although the compositions and descriptions of the state of the art provide descriptions useful for prolonging the overall fragrance character of a cosmetic composition, the methods have limitations. The perfume precursor method is limited by those chemical modifications that can be conveniently made to the perfume raw materials. Furthermore, the state of the art is limited by the chemical precursors used or by the use of low levels of perfume precursors, thus preventing the development of a fragrance oil that exhibits a wide range of high note characters throughout. weather. On the other hand, entrapment materials, when used in the traditional way, interact with a wide range of perfume materials including top, middle and bottom notes, prolonging the overall character of the fragrance as a whole. The state of the art does not sufficiently describe how to preferably delay the evaporation of a wide range of top note perfume materials within a single fragrance composition. Furthermore, since entrapment, as described, generally inhibits evaporation of only a relatively small amount of perfume raw materials, the low level of delayed release is often not perceptible to the user. The state of the art does not adequately describe how to provide a fragrance with a perceptible and lasting "top note" character.
Surprisingly it has now been discovered that compositions, especially cosmetic compositions, comprising a fragrance oil and a material that is capable of delaying evaporation of the fragrance oil, wherein the fragrance oil is mixed to comprise volatile "top notes" and residual "middle and bottom notes", where the weight ratio between both types of notes is in the range of approximately 1:20 to approximately 20: 1, and preferably in conjunction with a remainder of perfume raw materials with a low odor detection threshold, they can be used to create a long-lasting fragrance character profile that has perceptible and prolonged "top note" characteristics. In addition, it has been discovered that this long-lasting "top note" character of fragrance oils can be combined with the "middle and bottom note" characters to exceptionally achieve a long-lasting fragrance character profile with a broad spectrum of "top notes. , medium and low ”that would not have been possible to develop using traditional perfumery techniques.
Without wishing to be bound by theory, it is believed that when a composition according to the present invention is applied to a substrate there is an association between the perfume raw materials and the entrapment material that delays the evaporation of the perfume raw materials. Over time, this association is broken, resulting in the release of the perfume raw materials. Since the composition comprises a fragrance oil that has been developed with a given ratio between "top note" perfume raw materials and "middle and low note" perfume raw materials, the "top note" character is still perceived. over time by the user. Furthermore, since the fragrance oil can preferably be developed with the rest of the perfume raw materials with a low odor detection threshold, the user will perceive a very noticeable and novel fragrance character profile over time. This is because the perfume raw materials are still detectable even though only a relatively small level is being released.
Furthermore, since the volatilization rate of any given ingredient has hitherto been primarily related to its own boiling point, it has not been possible to obtain recurring and intermittent emissions (or pulses) of specific fragrance characters throughout the entire period of use. . Surprisingly it has now been discovered that, once a fragrance has been applied to a substrate using a composition of the present invention, the fragrance can be renewed over time, naturally or deliberately, releasing periodic and unexpected emissions of one or more fragrance characters. Without pretending to impose any theory, it is believed that this
ES 2 294 007 T3 can be achieved by increasing the natural decomposition rate of the fragrance oil trapping material association, for example by applying water naturally by breathing into the complex or by sweating, or artificially by spraying a mist and the like. This "activation" results in the user receiving a perceptible emission of the fragrance character. Surprisingly, it has been found that it is possible to "activate" this complex and therefore generate fragrance emissions several times during use. It is also believed that negative consumer perception of becoming accustomed to a scent can be minimized or avoided by periodic "activation" that produces an unexpected perceptible alteration of the overall character of the fragrance.
An object of the present invention is to provide compositions, especially cosmetic compositions, which convey a light, fresh, fruity, citrus, vegetal, or delicate floral "top note" fragrance character to the substrate on which they are applied. This and other objects of this invention will become apparent from the following description.
Summary of the invention
The present invention relates to a composition comprising:
(a) a fragrance oil comprising:
(i) perfume raw material, or perfume raw material mixture, of high note with a boiling point less than or equal to 250 ° C at 0.1 MPa (1 atmosphere pressure);
(ii) perfume raw material, or mixture of perfume raw materials, of medium or low note with a boiling point greater than 250 ° C at 0.1 MPa (1 atmosphere pressure);
(b) an entrapment material selected from the group consisting of capsules, microcapsules and nanocapsules, liposomes, perfume precursors selected from more than 1 type of chemical precursors, absorbents, cyclic oligosaccharides, and mixtures thereof;
(c) more than 50% volatile solvent having a vapor pressure of 2 kPa or more at 25 ° C;
wherein the weight ratio between the high note perfume raw materials and the medium or low note perfume raw materials within the fragrance oil is in the range of about 1:20 to about 20: 1.
This invention further relates to methods of using such compositions and to the use of such compositions to delay the release of volatile perfume raw materials from the substrate.
Detailed description of the invention
All percentages and ratios used herein are by weight of the total composition and all measurements are made at 25 ° C, unless otherwise specified. Unless otherwise indicated, all percentages, ratios, and levels of ingredients cited herein are based on the actual amount of the ingredient and do not include solvents, fillers, or other materials that could be combined with the ingredient in commercial products.
The term "dermatologically acceptable" as used herein means that the compositions, or components thereof, are suitable for use in contact with human skin without undue toxicity, incompatibility, instability, allergic response, and the like.
The term "safe and effective amount" as used herein means an amount of a compound, component, or composition sufficient to significantly induce a positive benefit, but low enough to avoid serious adverse effects, that is, to provide a ratio between Reasonable benefit and risk, within the scope of a well-founded medical judgment.
Active substances and other ingredients useful in the present invention can be categorized or described herein by their cosmetic and / or therapeutic advantage or by their postulated mode of action. However, it is understood that the active substance and other ingredients useful in the present invention may in some cases provide more than one cosmetic and / or therapeutic benefit or act through more than one mode of action. Accordingly, the classifications of the present invention are made for convenience of use and are not intended to be limited to one ingredient for the specially described application (s).
The elements of these compositions are described in more detail below.
ES 2 294 007 T3
Fragrance oil
The compositions of the present invention preferably comprise from about 0.01% to about 99%, preferably from about 0.25% to about 50%, more preferably from about 0.5% to about 40%, even more preferably from about 1% to about 25% and most preferably from about 2.5% to about 25%, by weight, of the fragrance oil.
As used herein, the term "fragrance oil" refers to the mixture of perfume raw materials that are used to impart a pleasant overall odor profile to a composition. As used herein the term "perfume raw material" refers to any chemical compound that is odoriferous when in an untrapped state, for example, in the case of perfume precursors the perfume component is considered, for the purposes of this invention, is a perfume raw material and the precursor chemical that serves as an anchor is considered to be the entrapment material. Furthermore, "perfume raw materials" are defined as materials with a ClogP value preferably greater than about 0.1, more preferably greater than about 0.5, even more preferably greater than about 1.0. As used herein the term "ClogP" means the base 10 logarithm of the octanol / water partition coefficient. This can be easily calculated with the aid of a program called "CLOGP" available from Daylight Chemical Information Systems Inc., Irvine CA, USA. Octanol / water partition coefficients are described in greater detail in US-A-5,578. 563.
In the present invention, by mixing various different perfume raw materials within the given ranges of weight ratio between "top note" and "middle or low note" a fragrance oil can be achieved which, when used in a composition, especially a cosmetic composition, in conjunction with an entrapment material, can convey a certain long-lasting character including "high note" characters to the composition in which it is used. The mixture of perfume raw materials used will be carefully selected and mixed to obtain a fragrance oil with the desired overall fragrance character profile.
The fragrance oil itself can comprise any suitable perfume raw material for use in the composition, especially cosmetic compositions. In general, the fragrance oil will most often be liquid at room temperature and will consist of a single individual perfume raw material. A wide variety of fragrance chemicals are known, including aldehydes, ketones, and esters. However, vegetable and animal oils and exudates comprising complex mixtures of various chemical components are also commonly known for their use as fragrances. Individual perfume raw materials comprising a known natural oil can be found in magazines commonly used by experts, such as "Perfume and Flavorist" or "Journal of Essential Oil Research". Additionally, some perfume raw materials are supplied by fragrance houses as proprietary blends in the form of special chords.
In order that fragrance oils can be developed with the appropriate character for the present invention, perfume raw materials have been classified based on two key physical characteristics:
(i) boiling point (PE) measured at 0.1 MPa (1 atmosphere pressure). The boiling points of many fragrance materials are described in Perfume and Flavor Chemicals (Aroma Chemicals) by Steffen Arctander (1969). The perfume raw materials for use in the present invention are divided into volatile raw materials (having a boiling point of less than or equal to about 250 ° C) and residual raw materials (having a boiling point greater than about 250 ° C, preferably greater than about 275 ° C). Volatile raw materials are considered to be, for the purposes of this invention, those that convey "top note" characters ie light, fresh, fruity, citrus, vegetable or delicate floral, to fragrance oil and the like. Similarly, residual perfume raw materials are considered to be those that convey "middle or low notes", ie musky, sweet, balsamic, spicy, woody, or rich floral, to fragrance oil and the like. All perfume raw materials will preferably have boiling points (BP) of about 500 ° C or less.
(ii) odor detection threshold which is defined as the lowest vapor concentration of the material that can be detected olfactorily. The odor detection threshold and some odor detection threshold values are described, for example, in "Standardized Human Olfactory Thresholds", M. Devos et al., IRL Press at Oxford University Press, 1990, and "Compilation of Odor and Taste Threshold Values Data ”, FA Fazzalar, publisher ASTM Data Series DS 48A, American Society for Testing and Materials, 1978, both publications being incorporated by reference. Perfume raw materials for use in the present invention can be defined as those with a low odor detection threshold of less than 50 parts per billion, preferably less than 10 parts per billion and those with an odor detection threshold. high that are detectable at a level greater than 50 parts per billion (values determined by reference above).
Since, in general, perfume raw materials refer to a single single compound, their physical properties (such as ClogP, boiling point, odor detection threshold) can be obtained from the reference texts cited above. In the case that the perfume raw material is a natural oil comprising a mixture of several compounds, the physical properties of the complete oil should be taken as the weighted average of
ES 2 294 007 T3 the individual components. In case the perfume raw material is a proprietary special accord, the physical properties will have to be obtained from the supplier.
In order to develop fragrance oils that are suitable for use in the present invention, it is necessary that the weight ratio between volatile "top note" and residual "middle and bottom notes" perfume raw materials is in the range of about 1:20 to about 20: 1, preferably about 1:10 to about 10: 1, more preferably from about 8: 1 to about 1: 2 and most preferably from about 1.2: 1 to about 1: 1.2. It is preferred that the fragrance oil comprises about 5% or more, more preferably about 5% to about 99%, even more preferably from about 5% to about 70%, still more preferably from about 10% to about 60% and with maximum preferably from about 25% to about 60%, by weight of the fragrance oil, of volatile "top note" perfume raw materials, ie, with a boiling point less than or equal to about 250 ° C. It is preferred that the fragrance oil also comprises from about 0.01% to about 95%, preferably from about 5% to about 85%, more preferably from about 10% to about 60%, by weight of the fragrance oil, of the Residual "middle and low note" perfume raw materials, that is, those with a boiling point greater than about 250 ° C. In a very specific embodiment of this application, the weight ratio of volatile "top note" perfume raw materials to residual "medium and low note" perfume raw materials within the fragrance oil is in the range of about 1: 20 to about 1:19 and less than about 5%, by weight of the fragrance oil, of top note perfume raw materials. This embodiment allows the fragrance character of a composition to be prolonged but is useful for preparing fragrance characters where specific "top note" characters are less desirable, eg, fragrances for use in men's toiletries and the like.
Additionally, in order to develop fragrance oils with a suitable character profile over time, it is preferred that the remaining raw materials in the fragrance oil have a low odor detection threshold. For use in the present invention it is preferred that the "top note" perfume raw materials in the fragrance oil comprise 5% or more by weight of the "top note" perfume raw materials, of the perfume raw materials. "high note" that have an odor detection level of less than or equal to 50 parts per billion, preferably less than 10 parts per billion. Furthermore, it is highly preferred that the "middle or low note" perfume raw materials in the fragrance oil comprise 10% or more, more preferably 20% or more and most preferably 50% or more, by weight of the raw materials. of "middle or low note", of "middle notes" or "low notes", or a mixture thereof, with an odor detection threshold of less than or equal to 50 parts per billion, preferably less than 10 parts per billion. Since materials with low odor detection levels can be detected when only very low levels are present, they are especially useful in developing the durable character of the fragrance oil released over time from the entrapment material. In general, it is preferred that all of the fragrance oil comprises from about 5% to about 95%, preferably from about 20% to about 75%, more preferably from about 25% to about 50%, and even more preferably from about 25% to about 40%, by weight of the fragrance oil, of perfume raw materials with a high odor impact.
It is another feature of the present invention that the fragrance oil preferably comprises a residue of perfume raw materials with a low odor detection threshold, so that the compositions can comprise levels of fragrance oil lower than would traditionally be present. This can be advantageous to minimize skin sensitization and also to reduce overall costs. As such, the compositions of the present invention may preferably comprise from about 1% to about 15%, more preferably from about 1% to about 8%, by weight, of fragrance oil.
In general, a wide range of suitable perfume raw materials can be found in US-A-4,145,184, US-A-4,209,417, US-A-4,515,705 and US-A-4,152,272. The following are non-exclusive examples of perfume raw materials that are useful in mixing and formulating fragrance oils for the present invention. Any proprietary perfume, natural oil, or specialty accord raw material known to those skilled in the art can be used in the present invention.
The volatile ("high note") perfume raw materials useful in the present invention are selected, but not limited to, from aldehydes with a relative molecular mass of less than or equal to about 200, esters with a relative molecular mass of less of or equal to about 225, terpenes with a relative molecular mass of less than or equal to about 200, alcohols with a relative molecular mass of less than or equal to about 200 ketones with a relative molecular mass of less than or equal to about 200, nitriles, pyrazines, and mixtures thereof.
Examples of "high note" volatile perfume raw materials having a boiling point of less than or equal to 250 ° C, with a low odor detection threshold, are selected, but not limited to, from anethole, methyl-heptin carbonate, ethyl acetoacetate, para-cymene, nerol, decyl aldehyde, para-cresol, methyl-phenyl-carbinyl acetate, alpha-ionone, beta-ionone, undecylenic aldehyde, undecyl aldehyde, 2,6 -nonadienal, nonyl aldehyde, octyl aldehyde. Other examples of volatile perfume raw materials having a boiling point of less than or equal to 250 ° C, which are generally known to have a low odor detection threshold include, but are not limited to, phenyl acetaldehyde. , anisic aldehyde, benzyl acetone, ethyl-2-methyl butyrate, damascenone, alpha-damascone, beta-damascone, flower acetate, frutene, fructone, herbavert, iso-citral cycle, methyl
ES 2 294 007 T3 isobutenyl tetrahydro pyran, iso-propyl quinoline, 2,6-nonadien-1-ol, 2-methoxy-3- (2-methylpropyl) -pyrazine, methyl-octine carbonate, tridecene-2-nitrile, allyl-amyl glycolate, cyclogalbanate, cyclal C, melonal, gamma nonalactone, cis1,3-oxathian-2-methyl-4-propyl.
Other "high note" volatile perfume raw materials having a boiling point of less than or equal to 250 ° C, which are useful in the present invention and have a high odor detection threshold are selected from, although but not limited to, benzaldehyde, benzyl acetate, camphor, carvone, borneol, bornyl acetate, decyl alcohol, eucalyptol, linalol, hexyl acetate, isoamyl acetate, thymol, carvacrol, limonene, menthol, iso-amyl alcohol, phenyl alcohol ethyl, alpha-pinene, alpha-terpineol, citronellol, alpha-thujone, benzyl alcohol, beta-gamma hexenol, dimethyl-benzyl carbinol, phenyl-ethyl-dimethyl carbinol, adoxal, allyl cyclohexane propionate, beta-pinene, citral, citronellyl acetate , citronellal nitrile, di-hydromyrcenol, geraniol, geranyl acetate, geranyl nitrile, hydroquinone dimethyl ether, hydroxycitronellal, linalyl acetate, phenyl acetaldehyde dimethyl acetal, phenylpropyl alcohol, prenyl acetate, triplal, tetrahydrolinalol, verdox and cis-3-hexenyl acetate.
Examples of residual "mid and low note" perfume raw materials having a boiling point greater than 250 ° C and a low odor detection threshold are selected, but not limited to, from ethyl methyl phenyl glycidate. , ethyl vanillin, heliotropin, indole, methyl anthranilate, vanillin, amyl salicylate and coumarin. Other examples of residual perfume raw materials having a boiling point greater than 250 ° C which are generally known to have a low odor detection threshold include, but are not limited to, ambrox, bacdanol, benzyl salicylate, anthranilate butyl, cetalox, ebanol, cis-3-hexenyl salicylate, lilial, gamma-undecalactone, gamma-dodecalactone, gamma-decalactone, calone, cimal, dihydro-iso-jasmonate, isoeugenol, liral, methyl-beta-naphthyl ketone, beta-naphthol methyl ether, para-hydroxyl phenyl butanone, 8-cyclohexadecen-1-one, oxocyclohexadecen-2-one / habanolide, florhydral, and intraleven aldehyde.
Other residual perfume raw materials having a "medium and low note" boiling point greater than 250 ° C that are useful in the present invention, but have a high odor detection threshold, are selected from, but not from limiting form, eugenol, cinnamic amyl aldehyde, cinnamic hexyl aldehyde, hexyl salicylate, methyl dihydro jasmonate, sandalora, velutone, undecavertol, exaltolide / cyclopentadecanolide, zingerone, methyl cedrilone, sandela, dimethyl benzyl carbinyl butyrate, dimethyl benzyl carbinyl isobutyrate, triethyl citrate, cashmeran, phenoxyethyl isobutyrate, iso-eugenol acetate, helional, iso-E super, gamma-methyl-ionone, pentalide, galaxolide and phenoxy-ethyl propionate.
Entrapment material
The compositions of the present invention comprise an entrapment material preferably at a level of from about 0.1% to about 95%, preferably from about 0.5% to about 50%, more preferably from about 1% to about 25% and still more preferably from about 2% to about 8%, by weight, of an entrapment material.
As defined herein an "entrapment material" is any material, which, upon application of the composition to a substrate, inhibits the volatility of the perfume raw materials in the fragrance oil, thereby delaying their evaporation. It is not necessary for the entrapment material to form an association with the perfume raw material within the composition itself, it is only necessary for this association to exist on the substrate after application of the composition. Non-exclusive examples of mechanisms by which evaporation delay can occur are obtained through the reversible or irreversible physical or chemical association of the entrapment material with the perfume raw material through complex formation, encapsulation, occlusion, absorption. , binding, or otherwise adsorption of the perfume raw materials from the fragrance oil.
As defined herein, "reversible entrapment" means any association of the entrapment material with the perfume raw material where the association can be undone so that the entrapment material and the perfume raw materials are released from each other. As defined herein, "irreversible entrapment" means any association of the entrapment material with the perfume raw material that cannot be undone. As defined herein, "chemically associated" means that the entrapment material and the perfume raw material are linked through a covalent, ionic, hydrogen, or other type of chemical bond. As defined herein, "physically associated" means that the entrapment material and the perfume raw material are linked through a bond with a force weaker than the Van der Waals force. It is highly preferred that the entrapment material and the perfume raw material form a reversible physical or chemical association on the substrate.
As defined herein, "retarding the evaporation of a perfume raw material" means slowing or inhibiting the evaporation rate of said perfume raw material from the substrate so that the "top note" fragrance character of the material perfume premium is detectable for at least 2 hours after application to the substrate.
The entrapment materials for use in the present invention are selected from capsules, microcapsules and nanocapsules, liposomes, perfume precursors selected from more than 1 type of chemical precursor, absorbents, cyclic oligosaccharides, and mixtures thereof. Preferred perfume precursors are selected
ES 2 294 007 T3 of more than 1 type of precursor chemical, absorbents and cyclic oligosaccharides and mixtures thereof. Cyclic oligosaccharides are highly preferred.
Within the entrapment association it is preferred that the weight ratio between the high note perfume raw material and the entrapment material in the associated form is in the range of about 1:20 to about 20: 1, more preferably in the range of about 1:20 to about 20: 1. range from about 1:10 to about 10: 1 and even more preferably in the range from about 1:10 to about 1: 4.
Complex formation using, for example, cyclic oligosaccharides
It is highly preferred for the compositions of the present invention that the entrapment material reversibly chemically and physically complexes with the perfume raw materials. Non-exclusive and preferred examples of entrapment materials that act in this way are cyclic oligosaccharides, or mixtures of different cyclic oligosaccharides.
As used herein the term "cyclic oligosaccharide" means a cyclic structure comprising six or more saccharide units. Preferred cyclic oligosaccharides for use in the present invention are those having six, seven or eight saccharide units and mixtures thereof, more preferably six or seven saccharide units and even more preferably seven saccharide units. It is common practice in the art to abbreviate the six-, seven-, and eight-unit cyclic oligosaccharides as α, β, and γ, respectively.
The cyclic oligosaccharide of the compositions used for the present invention can comprise any suitable saccharide or mixtures of saccharides. Examples of suitable saccharides include, but are not limited to, glucose, fructose, mannose, galactose, maltose, and mixtures thereof. However, the preferred ones for use in the present invention are the cyclic oligosaccharides of glucose. The preferred cyclic oligosaccharides for use in the present invention are α-cyclodextrins or / α-cyclodextrins or mixtures thereof and the most preferred cyclic oligosaccharides for use in the present invention are j¿-cyclodextrins.
The cyclic oligosaccharide or mixture of cyclic oligosaccharides for use in the present invention may be substituted by any suitable substituent or mixture of substituents. As used herein the use of the term "mixture of substituents" means that two or more other suitable substituents can be substituted on a cyclic oligosaccharide. Derivatives of cyclodextrin consist mainly of molecules in which some of the OH groups have been substituted. Suitable substituents include, but are not limited to, alkyl groups; hydroxyalkyl groups; dihydroxyalkyl groups; (hydroxyalkyl) alkylenyl bridging groups such as glycerol ethers of cyclodextrin; aryl groups; maltosyl groups; allyl groups; benzyl groups; alkanoyl groups; cationic cyclodextrins such as those containing 2-hydroxy-3- (dimethylamino) propyl ether; quaternary ammonium groups; anionic cyclodextrins such as carboxyalkyl groups, sulfobutyl ether groups, sulfate and succinylate groups, amphoteric cyclodextrins, and mixtures thereof. Other cyclodextrin derivatives are described in co-pending US application 09/32192 (May 27, 1999), all of which are incorporated by reference herein.
The substituents can be saturated or unsaturated, straight chain or branched. Preferred substituents include alkyl groups and hydroxyalkyl groups, both saturated and straight chain, and mixtures thereof. Preferred alkyl and hydroxyalkyl substituents are selected from Ci-C alkyl or hydroxyalkyl groups.<sub>8</sub> or mixtures thereof, more preferably the alkyl and hydroxyalkyl substituents are selected from the Ci-C alkyl or hydroxyalkyl groups<sub>6</sub> or mixtures thereof and even more preferably the alkyl and hydroxyalkyl substituents are selected from the Ci-C alkyl or hydroxyalkyl groups<sub>4</sub> and mixtures thereof. Especially preferred alkyl and hydroxyalkyl substituents are propyl, ethyl and methyl, more especially hydroxypropyl and methyl and even more preferably methyl.
The preferred cyclic oligosaccharides for use in the present invention are unsubstituted or substituted only with saturated straight chain alkyl or hydroxyalkyl substituents. Accordingly, preferred examples of cyclic oligosaccharides for use in the present invention are α-cyclodextrin, / α-cyclodextrin, methyl- α-cyclodextrin, methyl- / α -cyclodextrin, hydroxypropyl-α-cyclodextrin and hydroxypropyl- / α-cyclodextrin. The most preferred examples of cyclic oligosaccharides for use in the present invention are methyl-α-cyclodextrin and methyl- / α-cyclodextrin. These are marketed by Wacker-Chemie GmbH Hans-Seidel-Platz 4, Munich, Germany, under the trade names Alpha W6 M and Beta W7 M, respectively. Methyl- / α-cyclodextrin is especially preferred.
Cyclic oligosaccharide modification methods are well known in the art. For example, see "Methods of Selective Modifications of Cyclodextrins" Chemical Reviews (1998) vol. 98, No. 5, pp. 1977-1996, Khan et al. and US-A-5,710,268.
In addition to the preferred substituents themselves it is also preferred that the cyclic oligosaccharides of the compositions used for the present invention have an average degree of substitution of at least 1.6, where the term "degree of substitution" means the average number of substituents per saccharide unit. The preferred cyclic oligosaccharides for use in the present invention have an average degree of substitution of less than about 2.8. More preferably the cyclic oligosaccharides for use in the present invention have a medium degree of substitution
ES 2 294 007 T3 from about 1.7 to about 2.0. The average number of substituents can be determined using common nuclear magnetic resonance techniques known in the art.
The cyclic oligosaccharides of the compositions used for the present invention are preferably soluble in water and in ethanol. As used herein "soluble" means that at least about 0.1 g of solute is dissolved in 100 ml of solvent, at 25 ° C and 0.1 MPa (1 atmosphere pressure). Preferably the cyclic oligosaccharides for use in the present invention have a solubility of at least about 1 g / 100 ml, at 25 ° C and 0.1 MPa (1 atm) pressure. It is preferred that cyclic oligosaccharides are only present at levels up to their solubility limits in a given composition at room temperature. One skilled in the art will recognize that the levels of cyclic oligosaccharides used in the present invention will also depend on the components of the composition and their corresponding levels, for example the solvents used, the exact fragrance oils or the combination of the oils. fragrance, present in the composition. Therefore, although the cited limits for entrapment material are preferred, they are not exclusive.
Encapsulation using capsules, microcapsules and nanocapsules
Encapsulation of fragrances in capsules, microcapsules or nanocapsules that can decompose due to environmental triggers can be used to reduce the volatility of fragrance oils by surrounding the oil with small droplets as a strong wall. This could be sensitive or insensitive to water. In the first case, the fragrance is released when the encapsulated particle is affected by loss of moisture from the skin, while in the second case the wall of the capsule will have to be mechanically broken before the fragrance is released. Encapsulation techniques are well known in the art and are described, inter alia, in DE 1,268,316; US3,539,465; US 3,455,838.
Moisture sensitive capsules, microcapsules and nanocapsules are preferably formed from, but not limited to, a polysaccharide polymer. Examples of suitable polymers are dextrins, especially low viscosity dextrins, including maltodextrins. An especially preferred example of a low viscosity dextrin is one which, as a 50% dispersion in water, has a viscosity at 25 ° C, using a Brookfield viscometer equipped with a type "A" T-bar that rotates at 2.09 rad / s (20 rpm) in helical mode, 330 ± 20 mPa.s. This dextrin is known as Encapsul 855 and is sold by National Starch and Chemicals Ltd. Another example of a polysaccharide that can be used to form moisture sensitive capsules is acacia gum.
Temporary release microcapsules are also suitable for use in the compositions of the present invention to entrap hydrophobic perfume raw materials. Said compositions comprise the perfume raw materials encapsulated in a wax or polymer matrix, which in turn is coated with a compatible surfactant. The wax or polymers used to form the matrix have a melting point in the range of about 35 ° C to about 120 ° C at 0.1 MPa (1 atmosphere pressure). These are described in detail in EP-A-908,174.
Perfume precursors
Synthesis of perfume precursors or fragrance precursors from perfume raw materials can give rise to compounds that transmit a delayed release mechanism to that specific perfume raw material. The perfume precursors useful in the present invention include those selected from more than 1 type of precursor chemical which ensures the use of a wide range of possible perfume raw materials. This is consistent with the goal of providing unique fragrances with a broad spectrum of "top note" characters.
In a perfume precursor the perfume raw material has been reacted with more than one type of chemical groups, such as acetal, ketal, ester, and hydrolyzable organic or inorganic groups. As defined in the present invention, the perfume raw material is considered to be part of the fragrance oil and the chemical groups are considered to be part of the entrapment material. The perfume precursors themselves are designated as non-volatile or with very low volatility. However, once on the substrate, the perfume raw material is released from the perfume precursor. Once released, the perfume raw material has its original characteristics. The perfume raw material can be released from the perfume precursor in various ways. For example, it can be released as a result of simple hydrolysis, by displacement of an equilibrium reaction, by a change in pH, or by enzymatic release. The fragrances of the present invention can be relatively simple in composition and comprise a single chemical product or they can comprise highly sophisticated complex mixtures of natural and synthetic chemical components, all selected in order to obtain a desired odor.
Non-exclusive perfume precursors suitable for use in the present application are described in WO 98/47477, WO 99/43667, WO 98/07405, WO 98/47478 and in co-pending applications US 60/105380 (October 23, 1998 ) (WO 00/24721) and US 60/130108 (April 20, 1999) (WO 00/63339).
ES 2 294 007 T3
Absorption of perfume raw material
When the solution is not required to be clear, odor absorbing materials, such as zeolites and / or activated carbon, can be used to modify the release rate of the perfume raw materials.
A preferred class of zeolites are the so-called "intermediate" silicate / aluminate zeolites. Intermediate zeolites are characterized by SiO molar ratios<sub>2</sub>/Hello<sub>2</sub> of less than about 10, preferably in the range of about 2 to about 10. Intermediate zeolites have advantages over "high" zeolites since they have an affinity for amine-type odors, they are more efficient by weight in terms of odor absorption as they have a larger specific surface area, they are more tolerant to humidity and maintain their odor absorption capacity in water better than high zeolites. There are a wide variety of commercial intermediate zeolites suitable for use in the present invention such as Valfor® CP301-68, Valfor® 300-63, Valfor® CP30035 and Valfor® 300-56 available from PQ Corporation and the CBV100® series of zeolites from Conteka. Zeolite materials marketed under the names Abscents are also preferred.<sup>®</sup> and Smellrite<sup>®</sup> by The Union Carbide Corporation and UOP. These materials are typically available as a white powder in a particle size range of 3 to 5 pm. Such materials are preferred over zeolite intermediates for controlling sulfur-containing odors, eg, thiols and mercaptans.
Carbon materials suitable for use in the present invention are materials well known in commercial practice as absorbents for organic molecules and / or for air purification purposes. Such carbon material is often referred to as "activated carbon" or "active carbon." Said charcoal is marketed by commercial suppliers with names like Type CPG®; Type PCB®; Type SGL®; Type CAL® and Type OL® from Calgon.
Other suitable odor absorbers for use in the present invention include silica, activated alumina, bentonite, and kaolonite molecular sieves.
Volatile solvent
The compositions of the present invention comprise greater than about 50%, preferably from about 55% to about 99.9%, more preferably from about 60% to about 95%, even more preferably from about 65% to about 75%, by weight. , from a volatile solvent or mixture of volatile solvents. Any volatile solvent suitable for use in the compositions can be used in the present invention. The solvents for use in the present invention are preferably volatile organic solvents.
As used herein "volatile" refers to substances with a significant level of vapor pressure under ambient conditions, as is known to those skilled in the art. Volatile solvents for use in the present invention will have a vapor pressure of about 2 kPa or higher, more preferably about 6 kPa or higher at 25 ° C. Volatile solvents for use in the present invention will preferably have a boiling point less than 0.1 MPa (1 atm) of less than about 150 ° C, more preferably less than about 100 ° C, even more preferably less than about 90 ° C and even more preferably still less than about 80 ° C.
The volatile solvents for use in the present invention will preferably be safe for use on a wide range of substrates, more preferably on human or animal skin or hair. Suitable volatile solvents include, but are not limited to, those found in the CTFA International Cosmetic Ingredient Dictionary and Handbook, 7<sup>to</sup> edition, volume 2, pp. 1670-1672, edited by Wenninger and McEwen (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, DC, 1997). Conventionally used volatile solvents include C hydrocarbons<sub>3</sub> -C<sub>14</sub> saturated and unsaturated, straight or branched chain such as cyclohexane, hexane, heptane, isooctane, isopentane, pentane, toluene, xylene; halogenated alkanes such as perfluorodecalin; ethers such as dimethyl ether, diethyl ether; straight or branched chain alcohols and diols such as methanol, ethanol, propanol, isopropanol, n-butyl, t-butyl, benzyl alcohol, butoxypropanol, butylene glycol, isopentyldiol; aldehydes and ketones such as acetone; volatile silicones such as cyclomethicones, e.g. eg, octamethyl-cyclotetrasiloxane and decamethylcyclopentansiloxane; Volatile siloxanes such as phenyl-pentamethyldisiloxane, phenylethyl-pentamethyldisiloxane, hexamethyl-disiloxane, methoxypropyl-heptamethyl-cyclotetrasiloxane, chloropropyl-pentamethyldisiloxane, hydroxypropyl-pentamethyldisiloxane, octamethyl-cyclopentasiloxane, octamethyl-cyclotetrasiloxane, octamethyl-cyclotetrasiloxane, octamethyl-cyclotetrasiloxane propellants and mixtures thereof. Preferred volatile solvents are ethers such as dimethyl ether, diethyl ether; straight or branched chain alcohols and diols such as methanol, ethanol, propanol, isopropanol, n-butyl alcohol, t-butyl alcohol, benzyl alcohol, butoxy propanol, butylene glycol, isopentyldiol; volatile silicones such as cyclomethicones, for example octamethylcyclotetrasiloxane and decamethylcyclopentansiloxane; propellants and mixtures thereof. The most preferred alcohols for use in the present invention are C alcohols.<sub>1</sub> -C<sub>4</sub> straight or branched chain such as methanol, ethanol, propanol, isopropanol and butanol and mixtures thereof, ethanol being the most preferred use in the present invention.
ES 2 294 007 T3
Rest of the composition
The compositions in the present invention are useful for using a fragrance component in a wide variety of different types of compositions including those such as cosmetic compositions, fragrance compositions for use in humans or animals, air freshener compositions, aromatherapy compositions, washing compositions. of clothes and cleaners, products of type paper, cloth or other substrate with fragrance and the like and, in fact, in any type of composition that comprises a fragrance. In all of these cases, the compositions should comprise a variety of other optional ingredients that should make the compositions more acceptable or provide additional usage benefits. Such conventional optional ingredients are well known to those skilled in the art and will vary greatly depending on the field in which the compositions are to be used. Although the compositions according to the second aspect of this invention comprise more than 50% volatile solvent, they should be considered useful for inclusion in a wide variety of compositions with cosmetic and non-cosmetic benefits.
For cosmetic compositions in particular, the compositions may comprise any cosmetically acceptable ingredient, such as those described in the CTFA International Cosmetic Ingredient Dictionary and Handbook, 7<sup>to</sup> edition, edited by Wenninger and McEwen, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, DC, 1997). As used herein "cosmetically acceptable" means a material (eg, compound or composition) that is suitable for use in contact with the skin, hair, or other suitable substrate as defined herein below. However, the fact that these ingredients are cited as useful for inclusion in a cosmetic composition does not exclude them from being incorporated in any other type of composition comprising a fragrance formulated according to the present invention.
Non-volatile solvents
Although the compositions of the present invention must comprise a volatile solvent, they can also comprise "non-volatile" solvents. Suitable non-volatile solvents include, but are not limited to, benzyl benzoate, diethyl phthalate, isopropyl myristate, and mixtures thereof.
Molecular wedge materials
When cyclic oligosaccharides are present in the compositions of the present invention, a low molecular weight polyol molecular wedge material having from about 2 to about 12 carbon atoms is preferably used herein, preferably from about 2 to about 6 carbon atoms and at least one -OH functional group, preferably at least 2 -OH functional groups, to further prolong the fragrance character of the composition. These polyols can also contain ether groups in the carbon chain. Suitable examples include ethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,6-hexanediol, and mixtures thereof. When these polyols are present, they will be present at a level of from about 0.01% to about 20%, preferably from about 0.1% to about 10%, and especially from about 0.5% to about 5%, by weight, of the composition. It is preferred that the molar ratio of the molecular wedge material to the oligosaccharide is 10: 1 to 1:10, preferably 1: 1 or higher and especially 1: 1.
Without wishing to be bound by theory, the aforementioned molecular wedge molecules can form tertiary inclusion complexes with the complexed perfume material and the cyclic oligosaccharide. These small zwitterionic molecules can enter the cavity of the cyclic oligosaccharide and attach via their OH groups to the outer edge of the cyclic oligosaccharide via a hydrogen bond. This allows the inclusion of all or part of the fragrance material in the cavity of the cyclic oligosaccharide in such a way that the stability of the tertiary complex formed is increased relative to the complex formed by the fragrance material and the oligosaccharide alone.
Water
The compositions of the present invention can also comprise water. If present, the water will preferably comprise from about 0.1% to about 40%, more preferably from about 1% to about 30%, even more preferably from about 5% to about 20%, by weight, of the total composition.
There are numerous examples of additional ingredients that are suitable for inclusion in the present compositions. These include, but are not limited to, alcohol denaturants such as denatonium benzoate; UV stabilizers such as benzophenone-2; antioxidants such as tocopheryl acetate; preservatives such as phenoxyethanol, benzyl alcohol, methyl paraben, propyl paraben; dyes; pH regulators such as lactic acid, citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; deodorants and antimicrobials such as farnesol and zinc phenolsulfonate; humectants like glycerin; oils; skin conditioners like allantoin; cooling agents such as trimethyl-isopropyl-butanamide and menthol; hair conditioning ingredients such as panthenol, pantethine, pantothein or panthenyl ethyl ether and combinations thereof; silicones; solvents like hexi
ES 2 294 007 T3 lenglycol, polymers for fixing hair such as those described in WO-A-94/08557, salts in general, such as potassium acetate and sodium chloride, and mixtures thereof. If present, these additional ingredients will preferably be present at a level of less than 10% by weight of the total composition. More preferably these additional ingredients will be present at a level of less than 5% by weight of the total composition.
Forms of product presentation
The compositions for use in the present invention may be in any form suitable for use, more preferably for cosmetic use. These include, but are not limited to, vaporizers, sprays, emulsions, lotions, liquids, creams, gels, sticks, ointments, pastes, foams, and cosmetics (eg, semi-solid or liquid makeup, including foundation). Compositions for use in the present invention are preferably in the form of a vapor spray. The compositions of the present invention can be further added as an ingredient in other compositions in which they are compatible. As such, they can be used in a solid composition or applied to substrates, etc.
Compositions for use in the present invention will preferably comprise an acceptable carrier. The term "acceptable carrier" as used herein means one or more solid or liquid fillers, diluents, extenders, and the like that are acceptable as defined hereinbefore. The term "compatible", as used herein, means that the components of the compositions of this invention are capable of combining with the primary active substances of the present invention, and with each other, so that there is no interaction that can substantially reduce the efficacy of the composition in ordinary use situations. The type of vehicle used in the present invention depends on the type of product desired and may comprise, but is not limited to, solutions, aerosols, emulsions (including those of the oil-in-water or water-in-oil type), gels, solids, and liposomes.
Preparation of the composition
Fragrance compositions and oils for use in the present invention should be prepared according to procedures commonly used and well known to those skilled in the art, with similar phase fractionating materials being added in any order. Entrapment of the perfume raw materials can take place at any reasonable stage during the preparation of the overall composition. As such, the fragrance oil can be prepared in its entirety and then trapped with a suitable material prior to its addition to the remainder of the composition. Alternatively the entrapment material can be added to the remainder of the composition prior to the addition of the full fragrance oil. Lastly, it is possible to trap any individual perfume raw material, or group of raw materials, individually prior to their addition to the rest of the fragrance oil or to the rest of the composition.
Methods of use
The present invention preferably relates to compositions, especially cosmetic compositions and more especially fragrance compositions, which comprise a fragrance oil together with an entrapment material, such that the fragrance profile of the perfume raw material or perfume raw materials high note remains detectable for more than about 2 hours, preferably more than about 4 hours, more preferably more than about 6 hours, after the composition has been applied to the substrate.
The composition itself is preferably used to provide fragrance to a suitable substrate. As used herein the term "suitable substrate" means any surface on which the present composition can be applied without any adverse effect. This can include a wide range of substrates, including human or animal skin or hair, paper, furniture, materials, and can also include the air in a room. The preferred substrates are the skin or the hair, especially the skin.
The preferred compositions of the present invention can be used in a conventional manner to deliver a fragrance to a suitable substrate. An effective amount of the composition is applied to the substrate, typically about 1 µl to about 1000 µl, preferably about 10 µl to about 250 µl, more preferably about 25 µl to about 100 µl. The composition can be applied by hand, but is preferably applied by spray. Preferably the composition is then allowed to dry.
The periodic release of the compositions of the present invention can be achieved by the application, natural or artificial, of a material, such as water, which will activate the dissociation of the fragrance oil from the entrapment material. Such an emission can be achieved naturally by depositing, exhaling on the substrate to which the fragrance has been applied, rubbing the substrate and the like. In order to achieve such an emission artificially, it is necessary to use a cooling spray in conjunction with the compositions described herein.
ES 2 294 007 T3 memory. Such a refresher spray should comprise a material such as water which is capable of causing decomposition of the association between the fragrance oil and the entrapment material. The freshener spray would be applied to the substrate, for example, from an atomizer, whenever an emission is desired eg every hour after the initial application of the fragrance to the substrate. Whenever the freshener spray is applied, fragrance emissions are expected. Each fragrance release is expected to last for less than about 30 minutes, preferably less than about 15 minutes, more preferably less than about 10 minutes, and even more preferably less than about 5 minutes. It is expected that with use the fragrance can be emitted at least about 2 times or more, preferably about 4 times or more, and more preferably about 6 times or more.
Examples
The following examples better illustrate the preferred embodiments within the scope of the present invention. These examples are offered for illustrative purposes only and are not considered limitations of the present invention, as many variations of the invention can be made without departing from its scope. Unless otherwise indicated, all ingredients are expressed as a percentage by weight of the active ingredient.
Fragrance oil Examples I-VII
Examples I-VII are non-limiting examples of the fragrance oil.
<td>Raw material of</td><td>I (%)</td><td>II (%)</td><td>III (%)</td><td rowspan="2">IV (%)</td><td rowspan="2">V (%)</td><td rowspan="2">SAW(%)</td><td rowspan="2">VII (%)</td>
<td>fragrance</td><td></td><td></td><td></td>
<td>beta-damascone</td><td>or, 1</td><td> 0,0</td><td>0, c</td><td> 1,5</td><td> 0, 0</td><td> 0,0</td><td> 0,0</td>
<td>allylamylglycollate</td><td> 0,1</td><td> 0,0</td><td> 0,0</td><td> 0,0</td><td> 0,0</td><td> 0,3</td><td> 0, 3</td>
<td>beta-ionone</td><td> 3</td><td> 2,5</td><td> 0, 0</td><td>O! OR<sup>;</sup></td><td> 0,0</td><td> 0,0</td><td> 0,0</td>
<td>alpha-damascone</td><td> 0, 0</td><td> 0, 1</td><td> 0,1</td><td> 3</td><td> 0,2</td><td> 0,1</td><td> 0,2</td>
<td>acetate methylphenylcarbinyl</td><td> 0,0</td><td> 1,7</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td><td> 0, 4</td><td> 0, 0</td>
<td>cycloalbonate<sup>1</sup></td><td> 0,0</td><td> 0,0</td><td> 1,5</td><td> 0,0</td><td> 0,0</td><td> 0,0</td><td> 0, 5</td>
<td>methyl-isobutenyltetrahydro pyran</td><td> 0, 0</td><td> 0, 0</td><td> 0, 3</td><td>Or or</td><td> 0, 0</td><td> 0,0</td><td> 0, 1</td>
<td>ethyl-2-methylbutyrate</td><td> 0, 0</td><td> 0,0</td><td> 0,1</td><td>oo</td><td> 0, 0</td><td> 0,0</td><td> 0,1</td>
<td>fructone</td><td> 0, 5</td><td> 0,0</td><td> 2,0</td><td> 0,0</td><td> 0,1</td><td> 0,0</td><td> 1</td>
<td>flower acetate</td><td> 1</td><td> 0,0</td><td> 7,0</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td><td> 2</td>
<td>alpha-ionone</td><td> 0,5</td><td> 0,0</td><td> 3</td><td> 3</td><td> 0,3</td><td> 0,0</td><td> 1</td>
<td>melonal</td><td> 0, 0</td><td> 0, 0</td><td> 0, 0</td><td> 1,5</td><td> 0,2</td><td> 0,0</td><td> 0,0</td>
<td>undecylenic aldehyde</td><td> 0,0</td><td> 0,0</td><td> 0, 0</td><td> 0,0</td><td> 0,0</td><td> 0,4</td><td> 0, 0</td>
ES 2 294 007 T3
<td>Lemon oil, cold pressed</td><td>up to 100</td><td> 5</td><td> 0, 0</td><td> 0,0</td><td> 0,0</td><td> 0, 5</td><td> 0, 0</td>
<td>Bergamot Oil, Eco Essence</td><td> 25</td><td> 0,0</td><td> 0, 0</td><td> 14,5</td><td> 0, 0</td><td> 1,5</td><td> 0, 0</td>
<td>345-L blackcurrant base<sup>2</sup></td><td> 1</td><td> 0,0</td><td> 0, 0</td><td> 30</td><td> 3</td><td> 1,0</td><td> 0, 0</td>
<td>menthol</td><td> 0,5</td><td> 0,0</td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td>
<td>beta gamma hexenol</td><td> 0,5</td><td> 1</td><td> 0, 6</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td><td> 0,0</td>
<td>phenylethyl alcohol</td><td> 2</td><td> 0, 0</td><td> 8</td><td> 0, 0</td><td> 2, 5</td><td> 2, 5</td><td> 0, 0</td>
<td>phenoxyethyl propionate</td><td> 0,0</td><td>oo</td><td> 0, 0</td><td> 0, 0</td><td> 0, 5</td><td> 0, 0</td><td> 0, 0</td>
<td>linalool</td><td> 8</td><td> 5</td><td> 0, 0</td><td> 0, 0</td><td> 0, 0</td><td> 1,5</td><td> 0,0</td>
<td>cis-3hexenyl acetate</td><td> 0,0</td><td> 0,2</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td><td> 0,0</td>
<td>linalyl acetate</td><td> 0, 0</td><td> 5</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 1,2</td><td> 0, 0</td>
<td>dihydromyrcenol</td><td> 0, 0</td><td> 2</td><td>up to 100</td><td> 0,0</td><td>Or or</td><td>Or or</td><td> 0, 0</td>
<td>citronellol</td><td> 0,0</td><td> 10</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 1, 5</td><td> 0, 0</td>
<td>benzyl acetate</td><td> 0,0</td><td> 6</td><td>Or or</td><td> 0, 0</td><td> 0, 0</td><td> 4</td><td> 0, 0</td>
<td>verdox</td><td> 0, 0</td><td> 0,0</td><td> 7</td><td> 0, 0</td><td> 0,0</td><td> 0,0</td><td> 0, 0</td>
<td>triplal</td><td> 0,0</td><td> 0, 0</td><td> 0, 6</td><td> 0, 0</td><td> 0,0</td><td> 0,2</td><td> 0,0</td>
<td>alpha-terpineol</td><td> 0,0</td><td> 0,0</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 1,2</td><td> 0,0</td>
<td>dihydro-isojasmonate</td><td> 3, 5</td><td>up to 100</td><td> 0, 0</td><td> 0,2</td><td> 0,0</td><td> 2</td><td> 5</td>
<td>cetalox<sup>2</sup></td><td> 0,5</td><td> 0,2</td><td> 0, 3</td><td> 2, 2</td><td> 0, 0</td><td> 0, 1</td><td> 0, 0</td>
<td>bacdanol<sup>3</sup></td><td> 0, 1</td><td> 0, 0</td><td> 1,5</td><td> 0, 0</td><td> 0, 0</td><td> 0, 0</td><td> 1</td>
<td>undecalactone</td><td> 1</td><td> 2</td><td> 2</td><td> 0, 0</td><td> 0,0</td><td> 10, 3</td><td> 1</td>
<td>liral<sup>3</sup></td><td> 10</td><td> 15</td><td> 14</td><td> 0, 0</td><td> 10</td><td> 2</td><td> 10</td>
<td>florhydral<sup>4</sup></td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 5</td><td> 0,0</td><td> 2</td>
<td>cis-3hexenyl salicylate</td><td> 0,0</td><td> 2</td><td> 0, 0</td><td> 0, 0</td><td> 0, 0</td><td> 1,2</td><td> 2</td>
<td>indole</td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td> 0,0</td><td> 0, 5</td><td> 0, 5</td><td> 0, 0</td>
<td>ethylvair.il lina</td><td> 0, 0</td><td> 0,8</td><td> 0,7</td><td> 1,3</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td>
<td>heliotropin</td><td> 0,0</td><td> 0,0</td><td> 0, 0</td><td> 0,0</td><td> 0, 5</td><td> 0,0</td><td> 1,6</td>
<td>ebanol<sup>4</sup></td><td> 0, 0</td><td> 2,0</td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td>Or or</td><td> 0, 0</td>
<td>gamma decalactone</td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td> 4,5</td><td> 0,4</td><td> 0,0</td><td> 0, 0</td>
<td>Prunella<sup>2</sup></td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td>up to 100</td><td> 4</td><td> 0,0</td><td> 0, 0</td>
<td>lilial<sup>4</sup></td><td> 0, 0</td><td> 0,0</td><td> 0,0</td><td> 0,7</td><td> 0,0</td><td> 15</td><td> 10</td>
<td>benzyl salicylate</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td><td>C, 0</td><td>up to 100</td><td>up to 100</td><td> 10</td>
<td>oxocyclohexadecen- 2-one</td><td> 0,0</td><td> 8</td><td> 10</td><td> 1,5</td><td> 10</td><td> 0, 2</td><td> 15</td>
ES 2 294 007 T3
<td>Roselea<sup>3</sup></td><td> 0,0</td><td> 0,0</td><td> 0, 0</td><td> 0, 6</td><td> 0,0</td><td> 0,0</td><td> 5</td>
<td>exaltolide</td><td> 2,5</td><td> 8</td><td> 12</td><td> 0,0</td><td> 12</td><td> 0,4</td><td> 8</td>
<td>hexylcinnamic aldehyde</td><td> 2,2</td><td> 5</td><td> 0,0</td><td> 0,0</td><td> 5</td><td> 2</td><td> 0, 0</td>
<td>zingerone<sup>4</sup></td><td> 0,0</td><td> 0, 5</td><td> 0, 0</td><td> 0,0</td><td>OR 00</td><td>Or or</td><td>Or or</td>
<td>methyl cedrilone</td><td> 0, 0</td><td> 3</td><td> 0, 0</td><td> 0, 0</td><td> 15</td><td> 0,0</td><td> 4</td>
<td>eugenol</td><td> 0,0</td><td> 0,0</td><td> 1,3</td><td> 0,0</td><td> 0, 0</td><td> 0,0</td><td> 0,2</td>
<td>sandela<sup>4</sup></td><td> 0, 0</td><td> 0, 0</td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td> 10</td><td> 5</td>
<td>methyl dihydrojasmonate</td><td>Or or</td><td> 0,0</td><td> 0, 0</td><td> 0, 0</td><td> 10</td><td> 10</td><td>up to 100</td>
<td>gamma-methylionone</td><td> 0,0</td><td> 0,0</td><td> 0,0</td><td> 0,0</td><td> 0, 0</td><td> 10</td><td> 0,0</td>
<sup>1</sup> Dragoco Gerberding & Co AG, D-37601 Holzminden GERMANY <sup>2</sup> Firmenich SA, 1 Route des Jeunes, CH-1211 Geneva 8 SWITZERLAND <sup>3</sup> International Flavors & Fragrances 521 W. 57th St, New York, NY 10019 USA <sup>4</sup> Givaudan-Roure 19-23 voie des Bans BP98, 95101 Argenteuil Cedex, FRANCE
The perfume raw materials were mixed by stirring at room temperature.
Fragrance compositions Examples VIII-XII
<td></td><td>VIII (% by weight)</td><td>IX (% by weight)</td><td>X (% by weight)</td><td>XI (% by weight)</td><td>XII (% by weight)</td>
<td>Fragrance (selected from Examples I-VII) '</td><td> 10</td><td> 12,5</td><td> 15</td><td> 1,5</td><td> 12</td>
<td>Cyclic oligosaccharides<sup>5</sup></td><td> 2,5</td><td> 5</td><td> 10</td><td> 2, 5</td><td> 0, 0</td>
<td>Perfume Precursor I<sup>6</sup></td><td> 0, 0</td><td> 0,0</td><td> 0, 0</td><td> 0,0</td><td> 0,4</td>
<td>Perfume precursor II<sup>7</sup></td><td> 0,0</td><td> 0,0</td><td>Or or</td><td> 0, 0</td><td> 0,4</td>
<td>Ethanol</td><td>until the 100</td><td>until the 100</td><td>until the 100</td><td>until the 100</td><td>until the 100</td>
<td>Shameless water</td><td> 15,75</td><td> 13</td><td> 11, 5</td><td> 15, 8</td><td> 0,0</td>
<sup>5</sup> Beta W7 M available from Wacker-Chemie GmbH, Hanns-Seidel-Platz 4 Munich, DE r
° Perfume precursor comprising pro-melonal oxazolidine, Procter & Gamble, Cincinnati, Ohio <sup>7</sup> Perfume precursor comprising pro-damascone beta-amino ketone, Procter & Gamble, Cincinnati, Ohio
The cyclic oligosaccharide was dissolved in ethanol at room temperature by stirring. The fragrance and water were then added and mixed with stirring.
ES 2 294 007 T3
Cosmetic compositions Examples XIII-XV
<td></td><td>XIII (% by weight)</td><td>XIV (% by weight)</td><td>XV (% by weight)</td>
<td>Fragrance (selected from Examples I-VII)</td><td> 3</td><td> 2</td><td> 3</td>
<td>Cyclic oligosaccharides<sup>5</sup></td><td> 2</td><td> 1,5</td><td> 3</td>
<td>Zinc phenolsulfonate</td><td> 2</td><td> 1</td><td> 2</td>
<td>Dipropylene glycol</td><td> 30,5</td><td> 17</td><td> 14,5</td>
<td>Isopropyl myristate</td><td> 1,5</td><td> 7</td><td> 7</td>
<td>Ethanol</td><td>up to 100</td><td>up to 100</td><td>up to 100</td>
Beta W7 M available from Wacker-Chemie GmbH, Hanns-Seidel-Platz 4 Munich, DE
Zinc phenolsulfonate is added to ethanol and the mixture is stirred until completely dissolved. The dipropylene glycol is then added with stirring. The isopropyl myristate, the cyclic oligosaccharide and the fragrance are then added with stirring. For an aerosol deodorant a propellant, such as propane butane (CAP 40®) can be added to Examples XII-XIV according to standard industrial practice.
When Examples VIII-XV were applied to the substrate, the light, fresh, fruity, citrus, vegetal or delicate floral "top note" fragrance characters could still be perceived two hours after application. In contrast, when control compositions, comprising the same fragrance oil but without the entrapment material, were applied to a substrate, the same long-lasting "top note" effect was not obtained.
Contents8
15 members in 8 offices
Priority claims10
| Document | Office | Kind | Date |
|---|---|---|---|
| 0013534 | United Kingdom | A | |
| 0013534 | United Kingdom | A | |
| 20000013534 | United Kingdom | – | |
| 0026969 | United Kingdom | A | |
| 0026969 | United Kingdom | A | |
| 20000026969 | United Kingdom | – | |
| 0026969 | – | – | – |
| 019482610013534 | – | – | – |
| GB20000013534 | – | – | – |
| GB20000026969 | – | – | – |
Members15
| Document | Office | Kind | |
|---|---|---|---|
| GB0013534D0 | United Kingdom | D0 | |
| GB0026969D0 | United Kingdom | D0 | |
| WO0193814A2 | World Intellectual Property Organization (WIPO) | A2 | |
| AU6973201A | Australia | A | |
| WO0193814A3 | World Intellectual Property Organization (WIPO) | A3 | |
| EP1289485A2 | European Patent Office (EPO) | A2 | |
| US2003211125A1 | United States of America | A1 | |
| US2006243322A1 | United States of America | A1 | |
| US7208464B2 | United States of America | B2 | |
| EP1289485B1 | European Patent Office (EPO) | B1 | |
| AT374059T | Austria | T | |
| ATE374059T1 | Austria | T1 | |
| DE60130653D1 | Germany | D1 | |
| ES2294007T3This record | Spain | T3 | |
| DE60130653T2 | Germany | T2 |
Numbers
- Publication
- 2294007
- Publication, DOCDB
- 2294007
- Publication, EPODOC
- ES2294007T
- Application
- 1948261
- Application, DOCDB
- 01948261
- Application, EPODOC
- ES20010948261T
Titles2
- Spanish
- COMPOSICIONES DE FRAGANCIA.
- English
- FRAGRANCE COMPOSITIONS.
Classification
- CPC, 7
- A61Q13/00
- A61K8/0241
- A61K8/11
- A61K8/34
- A61K8/738
- A61K2800/412
- A61K2800/56
- IPC, 9
- A61Q13 00
- A61K8 04
- A61K8 11
- A61K8 27
- A61K8 37
- A61K8 73
- A61L9 04
- C11D3 50
- D06M13 00