JPH11240916A - Polymer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new polymer for trapping and holding a fragrant composition, especially a specific kind of a flavoring agent or molecules of malodorous substance or a specified malodor compound. SOLUTION: This polymer provides at least one kind of a binding site of a material acceptable by an organ sensation. Especially, at least a part of the binding site is molecular-imprinted with the material acceptable by the organ sensation. The polymer having characteristics binding to a specific kind of the molecule acceptable by the organ sensation can be used in the whole use aiming long term sustaining activities of the material acceptable by the organ sensation, for example, in a cosmetic, a deodorant, an air-refreshing product, a detergent product and a fiber for clothes. When the polymer is imprinted with a malodorous molecule, the polymer is used for decrease of the malodor.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a polymer which presents a binding site for at least one organoleptic receptor, and in particular, wherein said binding site, for example, releases at least one aromatic compound slowly. And at least partially molecularly imprinted polymers of organoleptic species. In particular, the invention relates to the preparation and use of fragrance compositions, in particular these novel polymers, for trapping and retaining molecules of one particular fragrance or malodorous substance or of particular malodorous compounds. These polymers, which have the property of binding certain types of organoleptic molecules, include, for example, cosmetics, deodorants, air refresh products,
It can be used in laundry products (e.g. detergents and fabric softeners) and in textile fibers for all applications where the long-lasting effect of organoleptic substances is intended. For example, if the polymer had been imprinted with malodor molecules, the polymer would be used to reduce previous malodors, for example, in deodorants, cosmetics, air refresh or laundry product applications.

[0002]

SUMMARY OF THE INVENTION Smell (od)
A common method currently used to impart our) is to directly mix the fragrance with the product. The main drawback of this method is that most of the fragrance is lost during manufacture because the fragrance molecules are too volatile and / or too unstable. Fragrances are often lost because of their lack of adhesion to the substrate to which they are applied, for example, skin, hair or fabric.

[0003] Occasionally, inclusion complexes that reduce volatility and improve stability are included.
The fragrance may be microencapsulated or treated with cyclodextrin to form x). However, these methods often do not provide satisfactory results or are very expensive. For example, US Pat. No. 5,382,567 states that the major drawback of cyclodextrins used to date is that they exhibit high water solubility immediately upon use in aqueous applications.

[0004] Most materials that have been used as solid phase adsorbents for the above purposes act in a relatively non-specific manner. In recent years, molecularly imprinted polymers (mol
ecully imprinted polymer
r) (Singular or plural forms are hereinafter abbreviated as MIP)
Are mock receptors capable of recognizing and binding various highly functionalized or high molecular weight molecules.
mimics) or plastic antibodies (K. Mosbach et al., Th.
e Emerging Technology of M
olecular printing and it
s Future Impact on Biotech
nology, Bio / Technology, 199
February 2006, 162-169 and M.P. T. Muldon
Et al., Plastic antibodies: mole
culturally imprinted polymers,
Chemistry & Industry, March 1996
18-204, 205-205). Thus, because of the low molecular weight and relatively low or no functionality of fragrance compounds, fragrance compounds seem to be unsuitable as print molecules for MIPs and have been produced to date. Did not.

According to Mosbach et al., The described MIP
To date, has been applied to the following fields: chromatographic separation of drug substances, use as artificial antibodies, simulated enzymes, catalysts and artificial enzymes in immunoassays, and devices for biosensors for structure-specific detection.

According to MT Muldon et al., MIP
In the first step of producing, the imprinted molecule is covalently linked to a polymerizable entity or the molecule is allowed to form a non-covalent interaction with the polymerizable entity. Subsequently, these molecular assemblies were cross-linked (Mosbach et al., Hydrolytical).
(see extraction) or, in the case of non-covalent interactions, solvent extraction of the imprinted molecule is a hard, insoluble solution containing recognition and binding sites specific for the printed molecule. ,
This produces a macroporous polymer.

[0007] The advantages of molecularly imprinted polymers compared to biological polymers such as proteins or antibodies are that they are easy to produce and that they are subject to harsh conditions, ie, especially pH, high temperature stability and the presence of solvents. It has the following chemical stability.

[0008] However, there are several disadvantages with respect to the MIPs described to date. First, the currently known M
IP is only suitable for highly functionalized and non-volatile molecules, flavors and / or fragrances are very volatile, non-polar and often only slightly functionalized, Is not considered appropriate. In the conventional state, the crosslinking agent 100 mmol
Less than 2 mmol of imprinting product per MI
Used for the production of P.

[0009] Second, however, the actual maximum capacity is M
Less than 1 mg of bound target product per gram of IP. This ability is too small to be used as a specific carrier for organoleptic applications, particularly those that slowly release aromatic molecules.

[0010]

SUMMARY OF THE INVENTION Contrary to the general belief of the person skilled in the art, it is surprising that volatile molecules, in particular flavor molecules or fragrance molecules (having at most a low polarity) are incorporated into the polymer by molecular incorporation. It was found that it could be printed. Furthermore, by imprinting the polymer with a large amount of these molecules, unexpected specific binding capabilities could be obtained. For example, surprisingly, less than 2 mmol of fragrance product could be bound per mmol of crosslinker.

[0011] Accordingly, the present invention provides a use for which a specific affinity for aroma products is exhibited and a long-lasting effect is required.
For example, polymers that adsorb and slowly release these molecules when used as perfuming agents in cosmetics, deodorants, air refreshers, laundry products (eg, detergents, fabric softeners) or textile fibers I will provide a.

When these polymers are imprinted, for example, with malodor molecules, they adsorb malodors to deodorize the surrounding air or, in deodorant applications, absorb sweat malodors Alternatively, it may be specially designed to adsorb odors in the wastewater. Examples of sweat-derived malodorous substances include steroids, for example,
Androstenone (Eigen et al., J. of the)
Soc. Of Cosmetic Chemist
1991, 173-185), fatty acids such as 3-methyl-2-hexenoic acid (Preti et al., Jo).
urnal of Chemical Economy,
17 (7), 1991, 1469-1492) and sulfur-containing substances (see WO 91/11988).

[0013]

DETAILED DESCRIPTION OF THE INVENTION To form a MIP according to the present invention, a functional monomer is polymerized with a free-radical generator as a cross-linking agent and a catalyst in the presence of one or more aroma products to be imprinted. . Here, the fragrance product (s) can be a fragrance composition, a particular fragrance, a malodorous product or a particular malodorous compound.

Typical functional monomers include a kind of acrylic acid and methacrylic acid (hereinafter referred to as (meth) acrylic acid), vinylbenzoic acid, phenylvinyl derivatives (eg, styrene), phenylpropenyl derivatives (eg, eugenol, any molecule having methyl eugenol acetate Oigeniru) or methylene or a vinyl group, i.e., RR'C = CH ₂ (wherein, R is an aliphatic or aromatic group, R 'represents an aliphatic group, an aromatic Which is a group or H).

[0015] Methacrylic acid and styrene are preferred monomers.

One or more other monomers can also be copolymerized with the above functional monomers. According to the invention, the comonomers are specifically selected such that the stiffness of the copolymerized polymer matrix is improved compared to the unmodified polymer matrix. Typical comonomers in the art include methyl (meth) acrylate, isobornyl (meth) acrylate (met)
h) acrylate), vinyl acetate, vinyl halide (vinyl halide).

Other functional monomers can be mixed with the above monomers and comonomers or used alone. Functional monomers include, for example, hydroxyalkyl (meth) acrylates, (meth) acrylalkylalkyl sulfonic acids and salts of metal (meth) acrylalkylsulfonates and quaternized ammonium alkyl (meth) acrylates.

Typical crosslinkers have at least two double bonds belonging to methylene or vinyl groups. Preference is given to ethylene glycol dimethacrylate, divinylbenzene or mixtures thereof. The molar ratio of crosslinker / functional monomer is between 1 and 10, preferably between 2 and 5.

To produce MIP, a functional monomer or a mixture of several different functional monomers is imprinted with an imprinting product.
cts) or forms a non-covalent interaction with the product. This can be performed in the presence or absence of a solvent.

Non-covalent interactions are preferred so that the imprinting product (s) can be easily removed after polymerization without hydrolysis in the next step.

For example, imprinting fragrances or flavor molecules exhibit some affinity with functional monomers, such as, for example, hydrogen bonding, lipophilicity or electrostatic interaction, and due to their olfactory properties they are perfumed.
Alternatively, it is derived from any substance or mixture of substances used in the flavor. These include alcohols, phenols, carboxylic acids, esters, carbonates, lactones, saturated and unsaturated ketones and aldehydes, aromatic compounds, nitrogen-containing products, sulfur-containing products, etc. known to those skilled in the art. Of various functionalities. Examples of fragrance or flavor products include citronellol,
Geraniol, phenylethyl alcohol, fixolide, cis-3-hexenol, eugenol, vanillin, substituted pyrazines and thiogeraniol.

Obviously, it is not possible to give a complete list of fragrance products or mixtures of such products that can be used for imprinting in polymers.
It is impossible to give a complete list of stench. However, several malodors have already been described and can be used to make the MIPs according to the invention.

The molar ratio of crosslinker / fragrance imprinted product is preferably between 0.5 and 50, preferably between 10 and 25.
Is particularly preferred.

To make the polymers of the present invention, any inert, non-aqueous organic solvent having excellent solubility in monomers (functional monomers and crosslinkers) can be used, Examples include toluene, hexane or chloroform, with toluene being preferred.
In some cases, it may be convenient to carry out the polymerization without any solvent (see Example 4 below).

The polymerization is carried out by standard methods known to those skilled in the art. Standard methods are described in the chemical literature, e.g.
J. Whitecombe et al., A new method.
dfor the introduction of
recognitionsite functiona
ly into polymers prepare
d by molecular imprintin
g: Synthesis and Character
ization of polymericrecept
tors for chocolate, J.A.
m. Chem. Soc., 117, 7105-711.
1, 1995. In the simple case, the following standard methods of free radical polymerization in solution are used: functional monomer (s), fragrance (s), and (one or more) of)
A mixture of the crosslinking agent and the solvent (s) at a temperature of -10 ° C to 70 ° C, preferably 0 to 5 ° C, is treated with a radical generator such as α, α'-azobisisobutyronitrile ( AIBN), di-t-butyl peroxide and / or UV light. In the presence of AIBN alone, a reaction temperature of 50 to 70 ° C., preferably
5 ° C is required.

The imprinted polymer can also be prepared in the presence of the molecule to be imprinted by other polymerization methods, such as polyaddition, ring opening polymerization or polycondensation. Typical monomers for polycondensation are tetra-alkylsilanes and tetra-alkoxysilanes.

Preferred catalysts (initiators) as radical generators are selected from the group consisting of diazo compounds such as AIBN, peroxides such as hydrogen peroxide, di-t-butyl peroxide and t-butyl hydroperoxide.
Reducing agents may be conveniently used in combination with the above peroxides. Preferred reducing agents are sodium metabisulfite and sodium formaldehyde sulfoxylate.

If desired, the polymer can be functionalized to improve its affinity for a suitable substrate. Typical functionalized monomers include one of the following compounds:
Hydroxyalkyl (meth) acrylates, (meth) acrylalkyl sulfonic acids, metal (meth) acrylalkyl sulfonates and salts of quaternary ammonium alkyl (meth) acrylates.

The molecularly imprinted polymer presenting the (free) binding site of the present invention is obtained by washing with a solvent to remove at least a portion of the imprinting product (s).
Any solvent for the imprinting product (s) and unreacted monomer (s) can be used. Preferably, the solvent is one of the group consisting of ethanol, methanol, acetic acid or a mixture thereof, optionally adding water. These polymers are used in particular to bind the odor (s).

The present invention provides a surprisingly high amount of fragrance and / or flavor chemical or fragrance composition (hereinafter referred to as "fragrance: fra") which has been used for imprinting.
(generally referred to as "grance"). For example, they can fill from about 1% to about 10%, preferably about 5%, by weight of the "fragrance" / polymer.
The resulting filled polymer has a substantially slower release profile in the washing process when used in detergents, soaps or fabric softeners than when applied directly to these products. For example, when an imprinted polymer loaded with a "fragrance" is used in a softener, the fragrance will remain on the fabric for a much longer time compared to a similar non-imprinted polymer.

The great advantage of the imprinted polymers of the present invention is that they can be filled with large amounts of "fragrances". By analysis and olfactory evaluation, "fragrance"
Released much more slowly from imprinted polymers in the solid phase than similar non-imprinted polymers, indicating that the odor lasted longer. This is important, for example, for air fresheners, cosmetics and all applications where it is important to release slowly when perfuming textile fibers. The imprint polymer itself can also constitute the fiber.

It has been found that imprinted polymers exhibit some specificity for imprinting molecules, for example, polymers imprinted with phenylethanol have no affinity for citronellol.

It has further been found that the polymer can be imprinted with a standard fragrance composition such that it has an affinity for most components of the fragrance or structurally related products.

The present invention also provides malodorous products, for example, polymers imprinted with perspiration, smoke, and cigarette smoke, to specifically bind malodors rather than perfumes in some applications. Interesting uses for polymers imprinted with sweat odors are in the fields of deodorants, air fresheners, cosmetics and the like. For example, 3-methyl-2-hexenoic acid, which is described in G. Preti et al., Journal of
An important human sweat component described in Chemical Ecology, Vol. 17 (7), 1991, the imprinted polymer specifically identifies this sweat component only from a mixture containing standard fragrances. Adsorption was found.

The present invention will be described in more detail with reference to the following examples, which do not limit the effective scope of the present invention.

EXAMPLES Example 1 Impregnated with diphenyl oxide for use in softeners
Linted styrene / ethylene glycol dimethacrylate
Preparation of Molecular Polymer Imprinted Polymers α, α′-azo-isobutyronitrile (AIBN, 164.0 mg, 1.0 mmol in toluene (40 ml))
l) and ethylene glycol dimethacrylate (19.
82 g, 100 mmol) and styrene (4.17 g,
40 mmol) and diphenyl oxide (1.2 g,
7.1 mmol) was stirred mechanically under argon while cooling on an ice bath (4 ° C.) until the AIBN was completely dissolved. Transfer the resulting solution as a thin layer about 5 mm thick to the photochemical reaction vessel, cool on an ice bath,
Then it was placed under a UV source (high pressure mercury lamp, 150 watts) for 17 hours. The resulting polymer was ground into small particles in a mechanical mixer. This powder is treated with a solution of ethanol (480 ml) in deionized water (720 ml), ethanol (500 ml) and methanol (500 ml).
Washed thoroughly. After drying under vacuum at 45 ° C. overnight, 14.2 g of purified diphenyl oxide-free, imprinted polymer was recovered. As a control polymer, exactly the same procedure was performed without using diphenyl oxide.

Preparation of Softeners Both the imprinted polymer and the control polymer have:
After filling with 5% by weight of diphenyl oxide in 25 ml of diethyl ether and homogenization, the solvent was completely evaporated. The resulting filled polymer (4.8 g, containing 0.233 g of diphenyl oxide) was added to a conventional softener base (2
3.3 g, eg Arq from Akzo Chemie
ud 2HT, Genapol T-150 and a 5/1/100 mixture of water). For reference experiments, 0.233 g of diphenyl oxide (1% / softener base) was added directly to the same softener base.

Treatment of cotton towel with softener The softener prepared above was diluted with 3 liters of cold water,
It was used to soften freshly washed cotton towels at room temperature for about 5 minutes by simulating the treatment in a washing machine. After the treatment, the towel was centrifuged at about 700 rpm in a washing machine. The towels were smelled by a panel of 10 persons in a humid state, a dry state after 6 hours and a dry state after 24 hours, respectively, at room temperature, by headspace measurement. Table 1 shows olfactory evaluation
Summarized in

[0038]

[Table 1]

Headspace Measurement The headspace (4 to 10 ml for wet towels, 1000 ml for dry towels) was loaded with adsorbent (Tena).
x), extracted with hexane and analyzed for diphenyl oxide content by gas chromatography (GC) analysis (30
mx 0.32 mm CP-wax 52-CB column, 6
(0 ° C., 60 to 235 ° C., 10 ° C./min). The results are listed in Table 2.

[0040]

[Table 2]

Example 2 Implemented with a standard fragrance composition for use in softeners
Styrene / ethylene glycol dimethacrylate
According to the procedure described in Example 1, the polymer was imprinted with 1.2 g of a standard perfume composition containing equal amounts of the 15 volatile components listed in Table 5. The resulting polymer and the corresponding control polymer are perfume-loaded control polymers,
The softener base of Example 1 was used to treat cotton towels, each containing only the perfume-loaded imprinted polymer and the perfume as a reference. The towels were olfactory evaluated by a panel of 10 persons and headspace measurements as described in Example 1. The results are summarized in Tables 3 to 5.

[0042]

[Table 3]

[0043]

[Table 4]

[0044]

[Table 5]

Example 3 3-methyl-2-hexenoic acid (a sweat component) for a deodorant was used.
Imprinted methacrylic acid / ethylene glycol dye
Preparation of Tacrylate Polymer Molecularly Imprinted Polymer α, α′-azo-isobutyronitrile (AIBN, 82.1 mg, 0.5 mmol) in toluene (20 ml)
And ethylene glycol dimethacrylate (9.91
g, 50 mmol) and methacrylic acid (1.72 g, 2
0 mmol) and the sweat component 3-methyl-2-hexenoic acid (256.3 mg, 2 mmol) were treated with AIB
Stir mechanically under argon while cooling on an ice bath until the N is completely dissolved. The resulting solution is transferred to a photochemical reaction vessel as a thin layer about 5 mm thick and placed on ice (4
° C) and then a UV source (high pressure mercury lamp, 150
(Watts) for 17 hours. The resulting polymer was ground into small particles in a mechanical mixer. This polymer powder is mixed with ethanol (240 ml) and acetic acid (120 m
l) and a mixture of deionized water (240 ml), a mixture of ethanol (200 ml) and acetic acid (50 ml), and finally washed thoroughly with pure methanol (250 ml). Purified after drying overnight at 45 ° C. under vacuum, 3
8.21 g of a polymer imprinted with -methyl-2-hexenoic acid were recovered. As a control, exactly the same procedure was performed without using the methylhexenoic acid. To the imprinted polymer and the control polymer (100 mg), respectively,
1 ml of a diethyl ether solution of 3-methyl-2-hexenoic acid (1 g / l), 1 ml of a standard perfume diethyl ether solution as described in Example 2 (1 g / l) and 50 microliters of water were charged. After homogenization,
The ether was evaporated with gentle heating for 0 minutes. After standing at room temperature in air for 3 hours, the samples were evaluated olfactoryly. Eight of the nine panels rated the imprint sample as having a much more pleasant, cleaner, less sweaty odor compared to the non-imprint control.

Example 4 Use in air fresheners, cosmetics or textile fibers
Methacrylic imprinted with citronellol
Preparation of Molecularly Imprinted Polymer without Using Acid / Ethylene Glycol Dimethacrylate Polymer Solvent α, α′-azo-isobutyronitrile (AIBN, 6
5.7 mg, 0.4 mmol), a mixture of ethylene glycol dimethacrylate (9.91 g, 50 mmol), methacrylic acid (861.0 mg, 10 mmol) and citronellol (12.9 g, 83 mmol) was completely purified by AIBN. And mechanically stirred under argon while cooling on an ice bath until dissolved. Transferring the resulting solution as a thin layer about 5 mm thick to the photochemical reaction vessel,
Cooled on ice (4 ° C.) and then placed under a UV source (high pressure mercury lamp, 150 watts) for 16 hours. The resulting polymer was ground into small particles in a mechanical mixer.
The polymer powder was mixed with a mixture of ethanol (240 ml), acetic acid (120 ml) and deionized water (240 ml), a mixture of ethanol (200 ml) and acetic acid (50 ml), and finally pure methanol (250 ml).
Washed thoroughly in l). After drying under vacuum at 45 ° C overnight,
8.21 g of the purified polymer imprinted with citronellol was recovered. For the reference polymer imprinted with a smaller amount of citronellol, the same procedure was performed using a further 15 ml of toluene and only 195.9 mg (1.25 mmol of citronellol). As a control, exactly the same procedure was performed without citronellol and using 15 ml of toluene. 50 mg of each of the three types of polymer was added to 0.025 mg of citronellol /
and suspended in 5 ml of a 70% methanol solution containing 18 ml for 18 hours. After centrifugation, the amount of adsorbed citronellol was evaluated by GC analysis. The amounts of citronellol (% / polymer) adsorbed on the control polymer and imprinted polymer prepared with or without solvent are shown in Table 6.

[0047]

[Table 6] The adsorption capacity of citronellol increases with the amount of citronellol used for imprinting.

Example 5 Use for air fresheners, cosmetics or textile fibers
Methacrylic imprinted with citronellol
Preparation of Molecularly Imprinted Polymer in the Presence of Acid / Ethylene Glycol Dimethacrylate Polymer Toluene α, α′-azo-isobutyronitrile (AIBN, 82.1 mg, 0.5 mmol) in toluene (10 ml)
And ethylene glycol dimethacrylate (9.91
g, 50 mmol) and methacrylic acid (1.72 g, 2
0 mmol) and citronellol (2.476 g, 1
5.8 mmol) was mechanically stirred under argon while cooling on an ice bath until the AIBN was completely dissolved. The resulting solution is transferred to the photochemical reaction vessel as a thin layer about 5 mm thick, cooled on ice (4 ° C.) and then placed under a UV source (high pressure mercury lamp, 150 watts).
Installed for 8 hours. The resulting polymer was ground into small particles in a mechanical mixer. This polymer powder was mixed with ethanol (240 ml), acetic acid (120 ml) and deionized water (240 ml), and ethanol (200 m
1) and acetic acid (50 ml), and finally washed thoroughly with pure methanol (250 ml). After drying under vacuum at 45 ° C. overnight, 8.3 g of purified citronellol-imprinted polymer was recovered. As a reference, exactly the same method was performed without using citronellol. Evaluation by adsorption in solid phase The imprinted polymer and the reference polymer were filled with citronellol (50 mg / g described in Example 1), compared by GC analysis of the methanol extract, and olfactory evaluation was performed for 14 days. Table 7 shows the results.

[0049]

[Table 7] Eleven panels unanimously found that the imprint material was stronger on olfactory properties after 18 days. Example 6 For use in air fresheners or textile fibers
Mixed imprinted with 2-phenylethanol
Tylene / methacrylic acid / ethylene glycol dimethacrylate
Preparation of Rate Polymer Molecularly Imprinted Polymer α, α′-azo-isobutyronitrile (AIBN, 82.1 mg, 0.5 mmol) in toluene (20 ml)
And ethylene glycol dimethacrylate (9.91
g, 50 mmol) and methacrylic acid (861.0 m
g, 10 mmol) and styrene (1.04 g, 10 m
mol) and 2-phenylethanol (244.3 mg,
2 mmol) was mechanically stirred under argon while cooling on an ice bath until the AIBN was completely dissolved. The resulting solution is transferred to the photochemical reaction vessel as a thin layer about 5 mm thick, cooled on ice (4 ° C.) and then cooled under a UV source (high pressure mercury lamp, 150 watts).
Set up for hours. The resulting polymer was ground into small particles in a mechanical mixer. This polymer powder was mixed with ethanol (240 ml), acetic acid (120 ml) and deionized water (240 ml), and ethanol (200 m
1) and acetic acid (50 ml) and then thoroughly washed with finally pure methanol (250 ml). After drying under vacuum at 45 ° C. overnight, 6.45 g of purified phenylethanol-imprinted polymer was recovered.
As a reference, exactly the same procedure was performed without using phenylethanol. Evaluation by adsorption in the solid phase
After filling with 0 mg / g phenylethanol, 50 mg / g citronellol and a standard fragrance composition (50 mg / g, 15 components, see Example 2), after 14 days at room temperature, GC
(Solid Phase Micro Extrac
(SPME) Supelco). The results are summarized in Table 8.

[0050]

[Table 8] From these results, the polymer imprinted with phenylethanol has high specificity for phenylethanol,
It showed specificity for perfume and no specificity for citronellol.

Continuation of the front page (51) Int.Cl. ⁶ Identification code FI C08F 20/00 C08F 20/00 C08J 9/26 102 C08J 9/26 102 (72) Inventor Werner Stauch Switzerland Wintertool, Geiselweitstrasse 42

Claims (29)

[Claims] 1. A polymer that presents a binding site for at least one organoleptic receptor. 2. The polymer according to claim 1, wherein the binding site is molecularly imprinted with at least one organoleptic substance. 3. The polymer according to claim 1, wherein said organoleptic substance is selected from the group consisting of aromatic compounds, flavor compounds and malodorous compounds. 4. The aromatic compound is an alcohol, a phenol, a carboxylic acid, an ester, a carbonate, a lactone, a saturated or unsaturated ketone, an aldehyde, an aromatic compound, a nitrogen-containing compound or the above compound. The polymer of claim 3, wherein the polymer is selected from the group consisting of any mixture of: 5. The flavor compound is selected from alcohols, phenols, carboxylic acids, esters, lactones, saturated or unsaturated ketones, aldehydes, aromatic compounds, nitrogen-containing compounds and any mixture of the above compounds. The polymer of claim 3, wherein the polymer is selected from the group consisting of: 6. The polymer according to claim 3, wherein the malodorous compound is selected from compounds present in human sweat, especially steroids, fatty acids and sulfur-containing compounds. 7. The polymer according to claim 6, wherein said malodorous compound is 3-methyl-2-hexenoic acid. 8. The method according to claim 1, wherein the aromatic compound (s) or the flavor compound (s) is released slowly.
The polymer according to Item. 9. The method according to claim 8, wherein the slow release of the aromatic compound (s) is effected by evaporation from a solid phase or release in an aqueous or organic solvent suspension. polymer. 10. The binding site according to claim 1, wherein the binding site is partially imprinted with at least one aromatic compound, and is capable of partially binding to an odorous compound. Polymer. 11. The method according to claim 2, which is produced by polymerizing at least one functional monomer and at least one crosslinker in the presence of at least one organoleptic substance. The polymer as described. 12. The imprinted organoleptic receptor (s) is at least partially purified by washing the polymer in a solvent (s) for the organoleptic receptor (s). 12. The polymer of claim 11, wherein the polymer is removed. 13. The solvent is selected from the group consisting of ethanol, methanol, acetic acid and mixtures thereof,
13. The polymer according to claim 12, wherein water is optionally added. 14. The polymer of claim 12, wherein the organoleptic receptor (s) is a malodorous compound (s). 15. There are two types of binding sites, one type imprinted with an aromatic compound (s), the other type imprinted with at least one malodorous compound, 13. The polymer of claim 12, wherein the malodorous compound (s) is subsequently dissolved by washing with a suitable solvent. 16. The polymer according to claim 11, wherein the functional monomer has a group having a double bond, preferably has a methylene or vinyl group. 17. The method of claim 17, wherein the functional monomer is acrylic acid,
17. The polymer according to claim 16, wherein the polymer is at least one selected from the group consisting of methacrylic acid, styrene and a phenylpropenyl derivative. 18. The polymer according to claim 11, wherein the crosslinking agent has at least two groups with double bonds, preferably two methylene or vinyl groups. 19. The polymer according to claim 18, wherein said crosslinking agent is ethylene glycol dimethyl acrylate, divinylbenzene or a mixture thereof. 20. A crosslinking agent / functionalized monomer molar ratio of 1
20. The polymer according to any one of claims 11 and 16 to 19, wherein the polymer is from 2 to 10, preferably 2 to 5. 21. Crosslinker / imprinting fragrance molar ratio of 0.5 to 50, preferably 10 to 25.
21. The polymer according to any one of claims 11 and 16 to 20, wherein 22. The polymer according to claim 11, wherein the polymerization is carried out in the presence of a catalyst and / or UV light as a radical initiator. 23. The polymer according to claim 11, wherein the polymer is obtained by polyaddition, ring opening polymerization or polycondensation. 24. The polymer according to claim 1, which is used for perfuming cosmetics, deodorants, air refreshers, laundry products, especially detergents or fabric softeners, and textile fibers. . 25. The method according to claim 10, wherein imprinting of the malodorous compound (s) is used to reduce malodor in deodorants, cosmetics, air refreshing or laundry applications. The polymer as described. 26. The method according to claim 1, wherein the imprint material (s) is present at about 1 to 10% by weight.
6. The polymer according to any one of 5. 27. A mixture of a functional monomer (s) and at least one crosslinking agent is polymerized in the presence of at least one organoleptic substance, and then the (one or more) 27) The method for producing a molecularly imprinted polymer according to any one of claims 2 to 26, comprising removing an organoleptic substance. 28. Polymerization of a mixture of the functionalized monomer (s) and at least one crosslinker in the presence of at least one organoleptic substance, and then the (one or more) The method for producing a molecularly imprinted polymer according to claim 1, comprising removing an organoleptic substance. 29. The method according to claim 27, wherein the removal is performed by washing with a solvent for the imprint organ sensory receptor substance (s).