Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1998-06-23
2001-03-27
Killos, Paul J. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S064000, C560S067000, C560S076000, C560S081000, C560S072000, C560S104000, C560S105000, C560S085000, C560S122000, C560S127000, C560S193000, C560S174000, C560S254000, C554S115000, C554S213000
Reexamination Certificate
active
06207857
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a new group of precursors for organoleptic compounds (such as fragrances and masking agents) and antimicrobial compounds.
BACKGROUND OF THE INVENTION
A principal strategy currently employed in imparting odors 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 many consumer products it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes 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 can be too expensive.
Fragrance precursors for scenting fabrics being washed in the presence of a lipase-containing detergents are described in WO 95/04809. The fragrance precursors contained in the detergent and/or in the softener are cleaved by the lipase and a single odoriferous compound, either an odoriferous alcohol or aldehyde or ketone is yielded. Thereby a prolonged scenting effect on the fabric is obtained.
SUMMARY OF THE INVENTION
One object of the present invention is to provide new precursors for compounds with different activities. It is a preferred object of the present invention to provide compounds cleaved under different activating conditions. A further object of the invention is to provide new compounds which are stable under transport and storage conditions. A further object of the present invention is to provide precursor molecules supplying different active compounds simultaneously or successively.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to compounds of the formula I
wherein
R
1
represents the residue of the enol form of an aldehyde or ketone,
X represents a saturated or unsaturated bivalent hydrocarbon residue with a straight or branched chain with 1 to 20 carbon atoms optionally containing one or more heteroatoms, such as O, N, S and/or P and/or a group —C(O)— and/or substituents of the formula —COOY, —OH, —C═O, or —NH
2
and Y is H, a metal atom or R
4
, and R
4
is the rest of an alcohol or phenol R
4
OH or has the same definition as R
1
and is the same or different as R
1
,
R
2
represents saturated or unsaturated, substituted or unsubstituted carbocyclic or heterocyclic residue or —COOY, wherein Y is H, a metal atom or R
3
, and R
3
is the rest of an alcohol or phenol or has the same definition as R
1
and is the same or different as R
1
, and R
2
can be H if X is substituted by —OH:
n is 0 or 1.
The present invention also includes a compound as defined in formula I which is selected from the group consisting of:
a) succinic acid methyl ester undeca-1,9-dienyl ester;
b) succinic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester methyl ester;
c) phenyl-acetic acid 2-methyl-undec-1-enyl ester;
d) phenyl-acetic acid undeca-1,9-dienyl ester;
e) phenyl-acetic acid 2,4-dimethyl-cyclohex-3-enylidenemethyl ester;
f) (4-methoxy-phenyl)-acetic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester;
g) 3-phenyl-propionic acid undeca-1,9-dienyl ester;
h) 3-phenyl-propionic acid 2,4-dimethyl-cyclohex-3-enylidene-methyl ester;
i) 3-phenyl-propionic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester;
j) 4-methoxy-benzoic acid 2-methyl-undec-1-enyl ester;
k) 4-methoxy-benzoic acid 2,4-dimethyl-cyclohex-3-enylidenemethyl ester;
l) 4-methoxy-benzoic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester;
m) 4-methoxy-benzoic acid undeca-1,9-dienyl ester;
n) succinic acid bis-[3-(4-tert-butyl-phenyl)-2-methyl-propenyl] ester;
o) succinic acid bis-[3-(3-isopropyl-phenyl)-but-1-enyl] ester;
p) succinic acid 3,7-dimethyl-oct-6-enyl ester 3-(isopropyl-phenyl)-but-1-enyl ester;
q) succinic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester 3,7-dimethyl-oct-6-enyl ester;
r) succinic acid 3,7-dimethyl-oct-6-enyl ester undeca-1,9-dienyl ester;
s) 3-phenyl-acrylic acid 3-(4-tert-butyl-phenyl)-2-methyl-3-phenyl-propenyl ester;
t) succinic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester methyl ester;
u) succinic acid 3-methoxycarbonylmethyl-2-pentyl-cyclopent-1-enyl ester methyl ester;
v) succinic acid 3-(4-isopropyl-phenyl)-2-methyl-propenyl ester methyl ester;
w) phenyl acetic acid 3-(4-isopropyl-phenyl)-2-methyl-propenyl ester;
x) phenyl acetic acid 3-methoxy carbonyl methyl-2-pentyl-cyclopent-1-enyl;
y) phenyl acetic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester;
z) (4-methoxy-phenyl)-acetic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester;
aa) 3-phenyl-propionic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester;
bb) 4-methoxy-benzoic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester;
cc) succinic acid bis-[3-(4-isopropyl-phenyl)-2-methyl-propenyl] ester;
dd) succinic acid bis-(2,6,10-trimethyl-undeca-1,9-dienyl) ester;
ee) succinic acid bis-(2,6-dimethyl-hepta-1,5-dienyl) ester;
ff) succinic acid bis-[2-(3,7-dimethyl-oct-6-enyloxy)-vinyl] ester;
gg) terephthalic acid bis-[3-(4-tert-butyl-phenyl)-2-methyl-propenyl] ester;
hh) 4-hydroxy-undecanoic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester;
ii) succinic acid 3,7-dimethyl-octa-2,6-dienyl ester 3-(3-isopropyl-phenyl)-but-1-enyl ester;
jj) succinic acid 3-(3-isopropyl-phenyl)-but-1-enyl ester phenethyl ester;
kk) succinic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester 3,7-dimethyl-octa-2,6-dienyl ester;
ll) succinic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester phenethyl ester;
mm) succinic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester 1,2-dimethyl-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-3-enyl ester;
nn) succinic acid 3,7-dimethyl-octa-2,6-dienyl ester undeca-1,9-dienyl ester;
oo) succinic acid 3-(4-isopropyl-phenyl)-2-methyl-propenyl ester phenethyl ester;
pp) succinic acid 3,7-dimethyl-oct-6-enyl ester 3-(4-isopropyl-phenyl)-2-methyl-propenyl ester;
qq) succinic acid 3,7-dimethyl-oct-5-enyl ester 2,6,10-trimethyl-undeca-1,9-dienyl ester;
rr) succinic acid 2,6-dimethyl-hepta-1,5-dienyl ester 3,7-dimethyl-octa-2,6-dienyl ester;
ss) succinic acid hex-3-enyl ester 3-methoxycarbonyl-methyl-2-pentyl-cyclopent-1-enyl ester;
tt) succinic acid 3,7-dimethyl-oct-6-enyl ester 3-methoxycarbonyl-methyl-2-pentyl-cyclopent-1-enyl ester; and
uu) phenyl-acetic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester.
The present invention also relates to personal care and laundry products containing a compound defined by formula I.
The compounds of formula I are not limited to any particular stereoisomers, all possible stereoisomers (E/Z isomers, enantiomers, diastereomers) and all mixtures are thus included within the scope of the invention.
The compounds of formula I are virtually odorless under room temperature, atmospheric conditions and about 20 to 100% relative humidity. However, under activating conditions, they are cleaved and one or more active compounds with organoleptic and/or antimicrobial properties are generated.
The activating conditions which lead to cleavage and the desired active compounds comprise the presence of skin bacteria, especially axilla bacteria, of an enzyme such as protease or lipase, elevated temperature or acidic or alkaline pH-values. The compounds of formula I, upon cleavage, provide aldehydes, ketones, lactones and/or alcohols having organoleptic and/or antimicrobial activity and therefore permit the development of useful consumer products with enhanced organoleptic and/or microbiological properties.
The compounds of the present invention can act as fragrance precursors in personal care products, in laundry products, cleaning compositions, pet care products and environment scents such as air fresheners. They can also act as precursors for odor masking agents in the same products as the fragrance precursors. They also can act as precursors for antimicrobial agents.
Anderson Denise
Frater Georg
Bryan Cave LLP
Givaudan-Roure (International) S.A.
Haracz Stephen M.
Killos Paul J.
Waddell Mark E.
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