Fragrance precursor compounds

Details Fragrance precursor compounds Fragrance precursor compounds

1999-12-20

2002-04-09

Kumar, Shailendra (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C252S008630, C424S065000, C514S532000, C514S617000, C554S035000, C554S213000, C560S060000, C564S170000

Reexamination Certificate

active

06369248

ABSTRACT:

The invention relates to fragrance and/or antibacterial precursor compounds. In particular, the invention relates to the use of compounds which can act as fragrance and/or antibacterial precursors in cosmetic products such as deodorants and antiperspirants and in laundry products such as detergents and fabric softeners or in air fresheners or hard surface cleaners. These compounds are normally odourless or nearly so, but upon contacting the skin as for example, in skin care compositions or in personal care compositions, produce fragrances. The compounds also produce fragrances when used in the presence of enzymes such as lipases and proteases, e.g. used in (laundry) detergents and fabric softeners, thus providing a prolongation of the fabric scenting effect. The compounds can also produce fragrances when heated.
A principal strategy currently employed in imparting odours to consumer products is the admixing of the fragrance directly into the product. There are however, several drawbacks to this strategy. The fragrance material can be too volatile, resulting in fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in loss during storage.
In some cases, fragrances are microencapsulated or treated with cyclodextrins to form inclusion complexes to help decrease volatility and improve stability. However, these methods are for a number of reasons often not successful. In addition, cyclodextrins can be too expensive.
In many consumer products it is desirable for the fragrance to be released slowly over time. Microencapsulation and cyclodextrins have been used to provide slow-release properties, however, they are subject to the same limitations as above.
The present invention now provides compounds which show a low level of odour, or are even odourless, and can be cleaved under activating conditions, e.g. by heat or by an acid, a base, bacteria or enzymes, to give fragrant molecules. So, for example, the compounds of the invention are odourless prior to application to the skin, but release fragrant molecules after application to the skin, that is, they provide a delayed release of the fragrance, in particular to the skin in the axilla which is the result of the cleavage by bacteria. The compounds of the present invention also release fragrant molecules when used in the presence of enzyme-containing products and, this way, provide a prolongation of the fabric scenting effect. The compounds of the present invention also release fragrant molecules when heated.
The compounds under consideration are compounds of the formula
in which n is 1, 2 or 3 and R
1
to R
6
represent, independently, branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic-radicals or hydrogen wherein these radicals may in addition contain one or more —O— and/or
groups, whereby one or two rings can be build by the combination of the respective R
1
to R
6
and this/these ring(s) can be further substituted by an alkyl-group, in which X is either O and R
7
represents a radical of an alcohol or phenol R
7
OH or X is N and R
7
represents the radical of an amine R
7′
R
7″
NH, whereby R
7′
and R
7″
represent independently, branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic radicals or either R
7′
R
7″
may be hydrogen, whereby the amine is a fragrant amine or the amine has more than 9 C atoms, whereby R
7
of the alcohol or phenol and R
7′
and/or R
7″
of the amine, respectively, may further contain at least one remaining part C(OH)R
1
R
2
—CR
3
R
4
—(CR
5
R
6
)
n
—CO— of formula I. Thus, the precursor compounds are esters of formula Ia
in which n is 1, 2 or 3 and R
1
to R
6
represent, independently, branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic-radicals or hydrogen wherein these radicals may in addition contain one or more —O— and /or
groups, R
7
represents a radical of an alcohol or phenol R
7
OH, whereby one or two rings can be build by the combination of the respective R
1
to R
6
and this/these ring(s) can be further substituted by an alkyl-group, whereby R
7
may further contain the remaining part C(OH)R
1
R
2
—CR
3
R
4
—(CR
5
R
6
)
n
—CO— of formula Ia, or amides of formula Ib
in which n is 1, 2 or 3 and R
1
to R
6
represent, independently, branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic-radicals or hydrogen wherein these radicals may in addition contain one or more —O— and /or
groups, whereby one or two rings can be build by the combination of the respective R
1
to R
6
and this/these ring(s) can be further substituted by an alkyl-group, and R
7
represents a radical of an amine R
7′
R
7″
NH, whereby R
7′
and R
7″
represent, independently, branched or unbranched, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic radicals or either R
7′
or R
7″
may be hydrogen, whereby the amine is a fragrant amine or the amine has more than 9 C atoms, whereby R
7′
and/or R
7″
may further contain at least one remaining part C(OH)R
1
R
2
—CR
3
R
4
—(CR
5
R
6
)
n
—CO— of formula Ib. With respect to the precursor compounds of formula Ia specifically the invention is related to those compounds in which n is 1, 2 or 3 and R
1
to R
6
represent, independently, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic-radicals or hydrogen wherein these radicals may in addition contain one or more —O— and/or
groups, R
7
represents a radical of a fragrant alcohol R
7
OH, whereby one or two rings can be build by the combination of the respective R
1
to R
6
and this/these ring(s) can be further substituted by an alkyl-group.
Further characteristics and advantages of the invention are described by claims 4 to 29 and by the following description and examples.
The compounds of formula I are not limited to any particular stereoisomers, all possible stereoisomers (enantiomers, diastereomers) and all mixtures are thus included within the scope of formula I.
The compounds of formula I may preferably be used as sustained release odorants but also to mask or attenuate undesirable odours or to provide additional odours not initially present in consumer products, i.e. laundry detergents, fabric softeners, fabric softeners sheets, hard surface cleaners, automatic dishwasher detergents and (other) enzyme-containing consumer products. Additional applications include cosmetic products destined for application to human skin such as underarm deodorants or antiperspirants or other deodorants contacting the body, or in hand lotions, baby powders, baby lotions, ointments, foot products, facial cleansers, body wipes, facial make-up, colognes, after-shave lotions, shaving creams, etc. Further additional applications include ironing treatments and air fresheners dispensed via heat.
The compounds of formula I may be used individually in an amount effective to enhance the characteristic odour of a material. More commonly, however, the compounds are mixed with other fragrance components in an amount sufficient to provide the desired odour characteristics.
The amount required to produce the desired, overall effect varies depending upon the particular compounds of formula I chosen, the product in which it will be used, and the particular effect desired.
For example, depending upon the selection and concentration of the compound(s) of formula I chosen, when added either singly or as a mixture, e.g. to a deodorant, laundry product, hard surface cleaner or air freshener composition at levels ranging from about 0.1 to about 10% by weight, or most preferred about 0.25 to about 4% by weight, an odorant, i.e. an odoriferous alcohol and an odoriferous lactone in an organoleptically effective amount is released when the product

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