Thursday, February 28, 2008

Patents on smells, malodor counteractants

Chandler Burr of the New York Times wrote:

Similarly, the scent makers — Symrise of Holzminden, Germany; Givaudan of Geneva; International Flavors and Fragrances of New York; and Takasago of Tokyo — spend billions on research to find new smell molecules, patent them and sell them. The innovative scents of these “captives,” as the patented molecules are known, are crucial to enticing consumers to buy the 600 or so new perfumes introduced every year and appealing to buyers of other fragrant products like soaps and air fresheners.(...)Like Pfizer, Abbott Laboratories or Novartis, Givaudan’s annual report prominently lists its new patents: “Three new molecules were introduced to the perfumers’ palette in the first half of 2007. Zinarine, natural green and tomato leaf notes with aspects of mint, fig, hyacinth; petitgrain Paradisamide, a long-lasting, fresh tropical fruit note with nuances of grapefruit, rhubarb and cassis; and Florymoss, a floral, green, mossy note which blends well with floral fruity and spicy accords.”

US 7,078,570 (to Givaudan) is a patent relating to molecules with fragrance. The abstract states: The present invention relates to substituted cyclohexenes, to their use as well as to their preparation method. These compounds have powerful long lasting natural fruity grapefruit notes with minty and fresh green tonalities.

Within the '570 patent, one has:


Synthesis of 2,6-dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enone

Odor: fruity, grapefruit, minty, bergamot



Synthesis of 2,2,6-trimethyl-6-(3-methyl-but-2-enyl)-cyclohex-3-enone

Odor: grapefruit, sage, saffron, lavander [sic]




Odor: minty, rhubarb, agrestic


Synthesis of 2,6-dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enol

Odor: grapefruit, vetiver, rhubarb, rosy

**Note separately -->


TABLE-US-00004 Pink grapefruit flavor for a yoghurt parts per weight Ethanol 805.2 Nootkatone (nature identical BV) 4.8 Orange oil 7.8-fold Brazil 34.0 Juniper berry extract CO.sub.2 10.0 Orange essence oil 10-fold Brazil 47.0 Orange oil 5-fold Palestine 50.0 Grapefruit base 48.0 1,2,6-Trimethyl-6-(3-methyl-but-2-enyl)-cyclohex- 1.0 2-enol 1000.0

In this pink grapefruit flavor 1,2,6-trimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enol increases freshness and harmonizes well with its fruity-hesperidic note. The compound gives volume and a more natural taste in a yoghurt.

US 7,332,462 (to Givaudan) notes:

Several approaches have been used to counteract malodors. These approaches include masking by superimposing the malodor with a pleasant stronger odor, cross-adaptation by blocking of the malodor olfactory receptors, suppression of the malodor by mixing with an ingredient that causes a negative deviation of Raoult's law, elimination of the malodor by chemical reaction, absorption of the malodor by a porous or cage-like structure, and avoidance of the formation of malodors by such routes as antimicrobials and enzyme inhibitors. All of these approaches are deficient, however, because they provide a perfumer with only limited options for malodor counteractants. Accordingly, there is still a need for additional and improved malodor counteractancy compositions.

It is known that fragrances may be designed to counteract malodors. The fragrance materials, which are most common to mask a malodor are those that contain a carbon-carbon double bond conjugated with one or more carbonyl groups. Aldehydes are the most commonly used materials of this class for malodor counteractancy, the most commonly used for deodorant properties are trimethyl hexanal, other alkyl aldehydes, benzaldehyde, and vanillin. For example, European Patent Application 0404470 discloses the use of fragrance materials with good malodor reduction efficacy, and European Patent Application 0545556 discloses mixtures of fragrance materials that mask malodors. The use of fragrance materials alone, however, may limit the types of fragrances a perfumer can create.

Other materials have also been shown to have malodor counteractancy (MOC) properties. Schleppnik, U.S. Pat. No. 4,622,221 ("Schleppnik '221") discloses the use of cyclohexyl alcohols and ester derivatives in room fresheners. Kulka, U.S. Pat. No. 3,074,891 discloses esters of alpha-, beta-unsaturated monocarboxylic acids as malodor counteractants. Kulka, U.S. Pat. No. 3,077,457 discloses fumaric acid esters as malodor counteractants. Schleppnik, U.S. Pat. No. 4,187,251 discloses alkyl cyclohexyl alkyl ketones as malodor counteractants. Schleppnik, U.S. Pat. No. 4,310,512 discloses the use of derivatives of acetic and propionic acids, and Schleppnik et al., U.S. Pat. No. 4,009,253 discloses the use of 4-cyclohexyl-4-methyl-2-pentanone as a malodor counteractant. These materials, however, are not capable of neutralizing all types of functional groups contained in malodor molecules. All of the U.S. patents discussed above are hereby incorporated by reference as if recited in full herein.


We have surprisingly found that certain aromatic unsaturated carboxylic esters wherein the unsaturation is conjugated to both the aromatic ring and the carbonyl group portion of the carboxylic ester counteract malodors. This malodor counteractancy effect is additive to that achieved by some classes of known malodor counteractancy, ingredients and, therefore, provides an additional advantage to e.g., perfumers who require low odor intensity or neutral odor malodor counteractancy compounds More surprisingly, these compounds may act synergistically with specific known MOC compounds.

As used herein, malodor counteractancy ("MOC") means the reduction of the perception of the offensiveness of a malodor or malodors to the human sense of smell. In the present invention, MOC is evaluated as set forth in the Examples. As used herein, a MOC effect is said to be "additive" when the malodor counteractancy effect of a MOC composition is equal to the sum of the malodor counteractancy effects of each MOC compound in the composition alone. An effect is said to be "synergistic" when the malodor counteractancy effect of a MOC composition is greater than the sum of the malodor counteractancy effects exhibited by each MOC compound in the composition alone.

The present invention provides a composition containing a compound or mixture of compounds having low odor intensity or neutral odor that counteracts malodors.

US 6,803,033 notes:

Absorbent materials are well known in the art to absorb moisture or malodors in products such as sanitary products, diapers, cat litter, air fresheners, and the like. Often mixtures of absorbents are used to obtain optimum performance with good odor control. For example, Brewer, U.S. Pat. No. 3,789,797 discloses an animal litter prepared from alfalfa, bentonite, and a binder for absorbing and neutralizing the odors of animal waste matter. Dickey, U.S. Pat. No. 4,519,340 discloses an absorbent composition for absorbing animal waste made from a mixture of natural absorbents such as corn stalks, wood shavings, hulls of cereal grain, and other components. Goodwin et al., U.S. Pat. No. 4,571,389 discloses an absorbent based on rice hull ash with multiabsorbent purposes. Karapasha et al., U.S. Pat. No. 5,306,487 discloses a particle composition for use with diapers and the like, which is based upon a high absorbent gelling material combined with odor-controlling materials such as zeolites, for example molecular sieve zeolites marketed under the trade name of ABSCENTS (Union Carbide Corporation and UOP), and activated carbon. Guarracino et al., U.S. Pat. No. 6,096,299 discloses an odor control material based upon a zeolite with a specific particle size. Neckernann, U.S. Pat. No. 3,816,577 discloses a cherry pit extract for deodorizing animal waste.

In absorbent products, it is also desirable to release a deodorant or a masking scent to maintain a pleasant smelling environment. In such products, fragrances are normally added directly to a particulate material or pre-mixed into an absorbent carrier. It is recognized that absorbers, especially those with high odor absorption capacity, may reduce the impact of fragrances if the fragrance is added directly to the absorber or premixed with, e.g., a zeolite.

One embodiment of the invention is a process for absorbing moisture and/or malodor, and providing a fragrance to the surrounding ambience. This process includes (a) providing a delivery vehicle containing an enrobement material, a fragrance, and a fixative, wherein the delivery vehicle is a free flowing powder; (b) combining the delivery vehicle with an absorbent material to form a mixture; and (c) contacting the mixture of (a) and (b) with a moisture and/or a malodor source.

Another embodiment of the invention is a fragranced delivery vehicle. This fragranced delivery vehicle includes a fragrance composition dispersed in a fixative and an enrobement material, wherein the fragrance composition, fixative, and enrobement material, when combined, form a free flowing powder.


In the present invention, the delivery vehicle is composed of a fixative and a fragrance that is enrobed in enrobement materials, i.e., powder materials that are capable of absorbing oleophilic fragrance materials to such an extent that the resultant mixture is a free flowing powder. In the present invention, the enrobement materials include for example, clays; silicas; celites; zeolites; metal salts, including for example, phosphates; cellulose, such as methyl cellulose; starches, carbonates, such as sodium bicarbonate; borates, such as sodium borate; sulfates such as sodium sulfate; water soluble polymers, borax; and mixtures thereof.


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