Malodor counteractant compositions

Perfume compositions – Perfume compositions – Ring containing active ingredient

Reexamination Certificate

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Reexamination Certificate

active

06610648

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to malodor counteractancy compositions. More particularly, the present invention relates to fragrance compositions containing one or more malodor counteractancy compounds.
BACKGROUND OF THE INVENTION
Malodors are offensive odors, which are encountered in the air and on many substrates such as fabrics, hard surfaces, skin, and hair. Malodors have either personal or environmental origin. For example sweat, urine, and feces malodors are personal in origin, whereas, kitchen, gasoline, cooking, tobacco smoke, etc. malodors are of environmental origin. While personal malodors are easily deposited on fabric, hair, and skin, environmental malodors also have a propensity to deposit on these substrates. Combinations of personal and environmental malodors make up a composite malodor, which has many oil soluble, water soluble, and solid components that have a vapor pressure at ambient temperatures, which is why humans can detect them.
Amines, thiols, sulfides, short chain aliphatic and olefinic acids, aldehydes, and esters form the largest and most unpleasant chemical groups found in sweat, household, and environmental malodors. These types of malodors typically include indole, skatole, and methanethiol found in toilet and animal odors; piperidine and morpholine found in urine; pyridine and triethyl amine found in kitchen and garbage odors, such as fish; hydrogen sulfide, nicotine, and various pyrroles found in cigarette smoke odors; and short chain fatty acids in axilla malodors.
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.
Unsaturated non-perfumery chemical compounds have also been shown to act as effective deodorants on the basis that many reactive odor-causing molecules may be eliminated by addition across the double bond. Unfortunately, many of the unsaturated compounds themselves have very unpleasant and offensive odors.
SUMMARY OF THE INVENTION
While all of the approaches set forth above are designed to mitigate malodors, none of them adequately eliminates the malodor. Accordingly, a need exists for compounds that counteract malodors alone, or in combination with other malodor counteractants. Ideally, the compounds should have little or neutral odors so that they may also be used in products that contain fragrance.
Accordingly, one embodiment of the invention is a composition containing a Class A compound of the formula:
wherein
R
1
is an hydrogen, an alkyl, an alkoxy, a substituted or unsubstituted aryl; and
R
2
is an alkyl having more than 6 carbon atoms, an aryl or a substituted aryl, and the Class A compound exhibits a malodor counteractancy (MOC) effect.
Another embodiment of the invention is a process for dispersing a malodor counteractancy (MOC) composition into a space. This process includes:
(a) incorporating into a consumer product a MOC composition containing a Class A compound of the formula:
 wherein
R
1
is an hydrogen, an alkyl, an alkoxy, a substituted or unsubstituted aryl; and
R
1
is an alkyl having more than 6 carbon atoms, an aryl or a substituted aryl; and
(b) dispersing an effective amount of the consumer product to achieve a MOC effect in the space.
A further embodiment of the invention is a process for imparting a MOC effect to a substrate. This process includes:
(a) contacting a substrate with a consumer product containing a Class A compound of the formula:
 wherein
R
1
is an hydrogen, an alkyl, an alkoxy, a substituted or unsubstituted aryl; and
R
2
is an alkyl having more than 6 carbon atoms, an aryl or a substituted aryl, which Class A compound has a MOC effect.
Another embodiment of the invention is a fragrance composition containing:
(a) a Class A compound having a malodor counteractancy (MOC) effect of the formula:
 wherein
R
1
is an hydrogen, an alkyl, an alkoxy, a substituted or unsubstituted aryl; and
R
2
is an alkyl having more than 6 carbon atoms, an aryl or a substituted; and
(b) a fragrance.
DETAILED DESCRIPTION OF THE INVENTION
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.
In the present invention, compounds having an aromatic unsaturated carboxylic ester, wherein the unsaturation is conjugated to both the aromatic ring and the carbonyl group of the carboxylic ester

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