Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1999-08-17
2003-02-18
Solola, T. A. (Department: 1609)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06521797
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to oxime carboxylic acid derivatives and the use of oxime carboxylic acid derivatives as precursors for (a) organoleptic compounds, especially for flavors, fragrances, (b) masking agents, and/or (c) antimicrobial compounds.
BACKGROUND OF THE INVENTION
A principal strategy currently employed to impart odors to consumer products is the admixing of a fragrance, flavor, masking agent or antimicrobial compound directly into the product to be treated. There are, however, several drawbacks to this strategy. The fragrance material may, for example, be too volatile and/or too soluble, resulting in, e.g., fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in fragrance loss during storage.
In many consumer products, it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes, especially with cyclodextrins, have been used to help decrease volatility, improve stability, and provide slow-release properties. However, these methods are, for a number of reasons, often not successful. In addition, cyclodextrins are too expensive to use commercially.
Fragrance precursors used to impart scent into fabrics during a washing cycle in the presence of a lipase-containing detergent are reportedly described in WO 95/04809. The fragrance precursors contained in the detergent and/or in the softener are cleaved by the lipase yielding a single odoriferous compound; either an odoriferous alcohol, aldehyde, or ketone. In this way, a prolonged scenting effect on the fabric is obtained.
SUMMARY OF THE INVENTION
An object of the present invention is to provide new precursors for organoleptic and/or antimicrobial compounds with varying activities.
Another object of the invention is to provide new precursors that are stable under conventional transport and storage conditions.
Another object of the invention is to provide precursors that supply different active compounds simultaneously or successively.
One embodiment of the present invention is an oxime carboxylic acid derivative precursor of the formula I:
wherein n is 1 or 0, X is O or N, R
2
and R
3
are part of an oxime R
2
R
3
C═NOH and R
1
is a substituted or unsubstituted, branched or unbranched alkyl-, alkenyl-,alkynyl, cycloalkyl-, cycloalkenyl-, alkoxyalkyl-, aryloxyaryl-, alkoxyaryl-, aryloxyalkyl-, or aromatic radical, or X
n
R
1
represents
and upon decomposition the precursor forms an organoleptic compound, a masking agent, and/or an antimicrobial compound.
Another embodiment of the invention is a composition that includes a compound selected from the following group: formula I, formula II, formula III, and mixtures thereof.
Another embodiment of the invention is a process for prolonging the effect of diffusion of a characteristic odor of an odoriferous compound on human skin that includes applying a composition containing at least one compound selected from the group consisting of formula I, formula II, formula III, and mixtures thereof to a surface of the skin.
Another embodiment is a process for prolonging the effect of diffusion of a characteristic odor of an odoriferous compound in laundry products, detergents or fabric softeners that includes applying a composition containing at least one compound selected from the group consisting of formula I, formula II, formula III, and mixtures thereof into a laundry product, a detergent or a fabric softener.
Another embodiment is a method for dosing a composition with a fragrance that includes adding a fragrance precursor selected from the group consisting of formula I, formula II, formula III and mixtures thereof to a composition selected from the group consisting of a cosmetic, a laundry product, a detergent, a fabric softener, a beverage, a food, an animal feed, a tobacco product, an air freshener, a candle, and a cleaning composition.
Another embodiment is a carboxylic acid derivative having the formula I
wherein n is 1 or 0, X is O or N, R
2
and R
3
are an oxime R
2
R
3
C═NOH and R
1
is a substituted or unsubstituted, branched or unbranched alkyl-, alkenyl-, alkynyl, cycloalkyl-, cycloalkenyl-, alkoxyalkyl-, aryloxyaryl-, alkoxyaryl-, aryloxyalkyl- or aromatic radical, or X
n
R
1
represents
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, certain oxime carboxylic acid derivatives have been found to be useful as organoleptic precursors. These oxime carboxylic acid derivatives are defined by formula I below:
wherein n is 1 or 0, X is O or N, R
2
and R
3
are part of an oxime R
2
R
3
C═NOH, and R
1
is a substituted or unsubstituted, branched or unbranched alkyl-, alkenyl-, alkynyl, cycloalkyl-, cycloalkenyl-, alkoxyalkyl-, aryloxyaryl-, alkoxyaryl-, aryloxyalkyl- or aromatic radical, preferably with 1 to 30 C atoms, or X
n
R
1
is
The compounds of formula I are not limited to any particular stereoisomer. Thus, the present invention includes all possible stereoisomers including E/Z isomers, enantiomers, diastereomers, as well as mixtures thereof.
In the present invention, R
1
may be selected from the following groups: oxo, hydroxo, carboxylic acid, ester, carbonate, carbamate, amide, amine, aryl, cycloalkyl, cycloalkenyl, oxime carboxylic acid derivative, and nitrile. Thus, for example R
1
may be substituted by at least one ester and/or carbonate group, that forms at least an alcohol, phenol, aldehyde, and/or ketone after cleavage of the oxime carboxylic acid derivative. R
1
may also be substituted with at least one carbamate and/or nitrile that forms an amine and/or a nitrile after cleavage of the oxime carboxylic acid derivative.
If X=N and n=1, R
1
may also represent the radical of an amino acid NH
2
R
1
or its derivatives.
In an oxime carboxylic acid derivative according to the present invention, when X is O and n is 1, R
1
is the radical of an alcohol or phenol or the enol form of an aldehyde or ketone, all represented by the general formula R
1
OH.
In another embodiment of the oxime carboxylic acid derivative of the present invention, when X is N and n is 1, —NR
1
represents the radical R′R″N— of an amine R′R″NH and R′ and R″ are independently, branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic radicals or either R′ or R″ may be hydrogen.
In another embodiment of the oxime carboxylic acid derivative of the present invention, when n is 0 and R′ is substituted with a hydroxy group, the oxime carboxylic acid derivative after cleavage forms a lactone. At least one of the yielded decomposition products, i.e. the oxime, alcohol, phenol, aldehyde, amine, lactone and/or nitrile is organoleptic, especially odoriferous, has masking activity, and/or antimicrobial activity.
The present invention includes as compounds of specific oxime carboxylic acid derivatives represented by the formula II:
and oxime carboxylic acid derivatives of formula III:
wherein R
2
and R
3
are defined as set forth in formula I, R
5
is branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkynyl, cycloalkyl-, cycloalkenyl- or aromatic radical R
4
is R
1
. For example, R
4
may be the radical of an alcohol, phenol, or the enol form of an aldehyde or ketone. In the present invention, precursors of fragrant alcohols, phenols, aldehydes or ketones are preferred.
In the present invention, a “precursor” is a compound that after decomposition under activating conditions, forms one of the following odoriferous oximes: 1,5-dimethyl-bicyclo[3.2.1]octan-8-one oxime; 2,4,4,7-tetramethyl nona-6, 8-dien-3-one oxime; 5-methyl-heptan-3-one oxime; or 1-bicyclo [2.2.1]hept-5-en-2-yl-ethanone oxime.
The present invention also includes non-organoleptic oxime precursors so long as they are effective as odor masking and/or antimicrobial agents and/or if other cleavage products thereof have at least one of the features set forth above.
The compounds of f
Anderson Denise
Frater Georg
Givaudan AG
Norris McLaughlin & Marcus P.A.
Parfomak Andrew N.
Solola T. A.
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