Data processing: structural design – modeling – simulation – and em – Modeling by mathematical expression
Reexamination Certificate
2001-12-19
2004-05-25
Hardee, John (Department: 1751)
Data processing: structural design, modeling, simulation, and em
Modeling by mathematical expression
C512S001000, C510S101000
Reexamination Certificate
active
06741954
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to a selection method for odorants for use in perfumed products, in which mathematical determination models are used. The invention also relates to products perfumed with odorants in which the odorants are selected using the mathematical determination models and also to a selection method for the preparation of novel odorants in which mathematical determination models are used. The invention further relates to odorants for which mathematical determination models are used for selection for the preparation of odorants as well as to products perfumed with odorants in which mathematical determination models are used for the selection for the preparation of the odorants.
BACKGROUND OF THE INVENTION
Odorants are used to improve the hedonic odor in a large number of products (perfumed consumer products). As a result of the perfuming, the impression of freshness and purity in the case of, for example, air fresheners, detergents and cleaners, and also the impression of the care action of bodycare compositions can be significantly enhanced. The use of odorants, therefore, represents a product improvement.
Throughout all of the application steps of the various perfumed consumer products, i.e. before, during and after application, some of the odorants are lost and cannot be perceived by smell by the user. Thus, for example, the formulations of various perfumed consumer products may include parts of the perfuming in such a way that the odor above the consumer product is significantly reduced. Furthermore, during the washing of laundry, for example, some of the perfuming is dissolved in the wash water and can likewise no longer be perceived by smell (U.S. Pat. No. 5,780,404).
To solve this problem, perfumers have hitherto selected, based on their experience and following laborious odor tests during washing experiments, the odorants which have a high scent intensity during and after the washing operation in the product to be perfumed in each case. In the case of these odorants, loss during the washing operation is reduced, i.e. the substantivity increases. This process is very laborious and is unable to give a comprehensive overview with regard to the suitability of all relevant odorants in all application steps of the product.
Further selection methods for odorants are described in U.S. Pat. Nos. 5,849,310, 5,833,999, 5,780,404, 5,668,094, 5,540,853, 5,500,154, 5,500,137, PCT 9,734,993, PCT 9,734,988, PCT 9,734,987, PCT 9,731,097, PCT 9,731,094, PCT 9,730,689 and PCT 9,730,688. Here, the physical parameters of the boiling point and the base-ten logarithm of the octanol/water partition coefficient (logP or logK
ow
) are used as descriptors.
U.S. Pat. No. 5,780,404 describes a method of reducing the loss of odorants during the washing operation. According to this, an odorant should have a logP value above 3 and a high boiling point above 250° C. in order to be transferred as so-called enduring perfume ingredient during the washing operation onto the laundry.
This selection method is often unsatisfactory (D. Pybus, C. Sell, The Chemistry of Odorants, p. 199), since not all of the properties of the odorants and interactions with the perfumed product (perfumed phase) or the substrate to be perfumed (phase to be perfumed) are taken into consideration. In general, the logP value, being a one-dimensional representative of the polarity, has proven unsuitable for describing the molecular interactions of complex systems (H.-D. Höltje, G. Folkers, Molecular Modeling, p. 50).
For example, some of the odorants deposited onto the perfumed product, such as, for example, laundry, cannot subsequently be released into the headspace (substrate to be perfumed), but are only removed during the next washing operation. This means that some of the odorants are likewise lost or un-utilized. Consequently, what is useful is not the unlimited adhesion of an odorant, but the targeted release of the desired amount of odorants at the desired time point.
Perring (D. Pybus, C. Sell, The Chemistry of Odorants, p. 188-200) and P. Müller (P. Müller, N. Neuner-Jehle, F. Etzweiler, Perfumer & Flavorist, 1993, 18, p. 45-49) discuss the volatility and substantivity and also the quantitative structure activity relationship (QSAR) for the correlation of the experimental values against physical parameters of odorants, such as the octanol/water partition coefficient (logK
ow
), the solubility in water and the vapor pressure. These physical parameters can either be determined experimentally or calculated using so-called fragment programs (clog P, Daylight, USA; Epiwin, Syracuse, USA).
For the correlation in the case of odorants, only a moderate correlation e.g. of the so-called affinity towards the logK
ow
value is described (S. Escher, E. Oliveros, JAOCS, 71, 1994, p. 31-40). On the basis of these experimental measurements and the correlations, it is not possible to adequately predict the partition behavior of odorants. In particular, the prediction of the relative headspace concentrations and the partition parameters of odorants between the perfumed phase and the phase to be perfumed has not been possible to an adequate degree.
This method permits only a rough estimation with regard to the partition behavior of odorants. However, an exact quantitative a priori prediction of odorant concentrations or partition parameters is not possible (D. Pybus, C. Sell, The Chemistry of Odorants, p. 200; P. Müller, D. Lamparsky, Perfumes, Art, Science & Technology, p. 198).
As is known, humans perceive an odor (G. Ohloff, Riechstoffe und Geruchssinn [Odorants and Sense of Smell], p. 1-5) as a result of the contact of volatile organic compounds with the olfactory mucosa present in the nose. This means that a perfume containing odorants must exist with a sufficient concentration in the headspace above the perfumed product and must not remain permanently within the perfumed consumer product or on the substrate to be perfumed. In this connection, a partition parameter is defined as the distribution of the odorant between the solid or liquid phase in the consumer product or its application form, such as, for example, an aqueous solution, on the one hand, and the gas phase surrounding the consumer product on the other hand: the higher the concentration of the odorant in the gas phase relative to the concentration of the odorant in the solid or liquid phase of the consumer product, the higher the numerical value of the partition parameter. This distribution depends individually on the formulation of the consumer product and the application step in question, and on the specific molecular properties of the odorants.
To determine the olfactory quality and suitability of odorants both from consumer products and also during and after use of the consumer products, a large number of laborious and time-consuming experimental work is usually carried out. This ascertains the odorants suitable for the perfuming. This work includes both analytical and also sensory measurements. This information is then used in the preparation of perfume oils.
It is also known that different consumer products influence the release of odorants to markedly varying degrees (P. Müller, D. Lamparsky, Perfumes, Art, Science & Technology, p. 198-206). It is noteworthy that even different formulations of a consumer product category, e.g. different washing powders, shampoo or soap formulations, differ in their odorant release behavior such that determination of the partition parameters should expediently be carried out for each individual formulation. In practice, this work cannot be carried out due to the enormous cost. Perfumes, Art, Science & Technology, p. 172-180 describes the experimental work for determining odorants in the headspace.
In a QSAR (Böhm, Klebe, Kubinyi, Wirkstoffdesign [Active Ingredient Design], p. 363), a correlation between experimental values, such as, for example, the active concentration of active ingredients, on the one hand and physicochemical values on the other hand is carried out. These physicoch
Bürger Thorsten
Finke Anja
Klamt Andreas
Lohrenz John
Matthiesen Svend
Hardee John
Pendorf & Cutliff
Symrise GmbH & Co. KG
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