Pro-fragrance linear acetals and ketals

Details Pro-fragrance linear acetals and ketals Pro-fragrance linear acetals and ketals

2002-05-09

2004-01-13

Gupta, Yogendra N. (Department: 1751)

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

Organic compounds

Oxygen containing

C568S062000, C568S075000, C510S101000

Reexamination Certificate

active

06677491

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to pro-fragrance compounds useful in laundry detergent compositions. The pro-fragrance compounds comprise a fragrance raw material component and a solubility or substantivity component which can be independently adjusted to meet the specific requirements of the formulator. The pro-fragrance compounds are especially useful for delivering a “through the wash” fresh-like or clean-like fragrance to fabric which remains on the fabric and is continuously released for extended periods after the conclusion of the laundry cycle.
BACKGROUND OF THE INVENTION
In addition to the removal of stains, dirt, soil, grime, and grease from fabric, laundry detergent formulators have attempted to deliver a “fresh” or “clean” odor to washed clothing to provide an olfactory aesthetic benefit and to serve as a signal that the product is effective. Laundry detergent compositions, including rinse-added fabric softeners and dryer-added substrates, are currently formulated with perfume and fragrance ingredients which are aesthetically pleasing to the consumer but which fail to deliver a prolonged “fragrance” or “pleasurable smell” to the finished, cleaned fabric.
Among the most readily perceived fragrance materials are the perfume “top” and “middle” notes which are highly volatile compounds and which are usually detectable at low levels. However, these highly volatile materials are typically lost either during the prolonged heating which takes place in an automatic dryer or they lack the substantivity necessary to deposit onto the fabric surface and are therefore lost during the laundry rinsing process.
Attempts have been made to deliver perfume ingredients onto fabric which can survive the laundry rinsing and drying cycles and therefore provide a residual “fresh” or “clean” odor to the washed material. However, none of these attempts have suitably provided fabric with a protracted release of fragrance raw materials which provide a “fresh” or “clean” smell for a period up to two weeks after washing. There has especially been a long felt need to deliver certain tertiary alcohol fragrance raw materials inter alia linalool and dihydromyrcenol.
Accordingly, there remains a need in the art for a fragrance delivery system wherein perfume raw materials are delivered to fabric by way of a laundry detergent composition which provides the cleaned clothing or fabric with a “fresh” or “clean” smell for a period up to two weeks after washing. Also, there is a need for fragrance releasing compounds which deliver a “fresh” or “clean” fragrance in which the solubility and substantivity properties of the compound can be varied to match various formulation and delivery parameters inter alia compatibility with surface active adjuncts and fabric type. In addition, there is a need for a fragrance delivery system suitable for providing sustained release or enhanced longevity fragrances to a variety of personal care and personal hygiene products inter alia deodorants, body lotions or creams, and shampoos.
BACKGROUND ART
The following relate to the subject matter of fragrance ingredients. U.S. Pat. No. 5,232,612 Trinh et al., issued Aug. 3, 1996; U.S. Pat. No. 5,506,201 McDermott et al., issued Apr. 9, 1996; U.S. Pat. No. 5,378,468 Suffis et al., issued Jan. 3, 1995; U.S. Pat. No. 5,266,592 Grub et al., issued Nov. 30, 1993; U.S. Pat. No. 5,081,111 Akimoto et al., issued Jan. 14, 1992; U.S. Pat. No. 4,994,266 Wells, issued Feb. 19, 1991; U.S. Pat. No. 4,524,018 Yemoto et al., issued Jun. 18, 1985; U.S. Pat. No. 3,849,326 Jaggers et al., issued Nov. 19, 1974; U.S. Pat. No. 3,779,932 Jaggers et al., issued Dec. 18, 1973; JP 07-179,328 published Jul. 18, 1995; JP 05-230496 published Sept. 7, 1993; WO 96/14827 published May 23, 1996; WO 95/04,809 published Feb. 16, 1995; and WO 95/16660 published Jun. 22, 1995. In addition, P. M. Muller, D. Lamparsky
Perfumes Art, Science,
&
Technology
Blackie Academic & Professional, (New York, 1994) is included herein by reference.
SUMMARY OF THE INVENTION
The present invention meets the aforementioned needs in that it has been surprisingly discovered that certain linear acetals and ketals can be used to deliver perfume or fragrance raw materials onto fabric “through the wash” from a single precursor pro-fragrance molecule having variable fabric substantivity, variable solubility as well as variable fragrance release rate. These pro-fragrances can be used to deliver tertiary alcohol raw materials as well as primary and secondary fragrance raw material alcohols which impart a “fresh” or “clean” aesthetic odor benefit to fabric or to human skin when the skin is contacted with a personal care or personal hygiene product inter alia deodorants, body lotions or creams, and shampoos, which comprises the pro-fragrances of the present invention. In addition to the short-term pleasurable odor benefits, the pro-fragrances according to the present invention continue to release their fragrance raw materials for as long as several weeks depending upon the structure of the pro-accord.
The pro-fragrances described herein comprise fragrance raw materials in a stable, releasable form. The pro-fragrance containing laundry detergent compositions of the present invention can comprise any number of pro-fragrances and are suitable for delivery of any type of fragrance “characteristic” desired by the formulator.
The first aspect of the present invention relates to pro-fragrance compounds having the formula:
R
1
and R
2
are each independently:
a) C
8
-C
22
, preferably C
8
-C
12
linear or branched alkyl;
b) C
8
-C
22
, preferably C
8
-C
12
linear or branched alkenyl;
c) C
2
-C
20
, preferably C
2
-C
12
, more preferably C
2
-C
6
substituted or unsubstituted alkyleneoxy;
d) C
3
-C
20
, preferably C
3
-C
12
, more preferably C
3
-C
6
substituted or unsubstituted alkyleneoxyalkyl;
e) C
7
-C
20
, preferably C
7
-C
12
, more preferably C
7
substituted or unsubstituted alkylenearyl;
f) C
6
-C
20
, preferably C
6
-C
10
, more preferably C
6
substituted or unsubstituted aryloxy;
g) C
7
-C
20
, preferably C
8
-C
12
, more preferably C
8
substituted or unsubstituted alkyleneoxyaryl;
h) C
7
-C
20
, preferably C
7
-C
11
, more preferably C
7
oxyalkylenearyl;
i) C
2
-C
20
, preferably C
2
-C
12
, more preferably C
2
-C
6
alkylenecarboxy having the formula:
—(CH
2
)
x
R
9
wherein R
9
is —CHO, —CO
2
M; —CO
2
R
10
, —CONH
2
, —CONHR
10
, —CONR
10
R
11,
and mixtures thereof; wherein R
10
and R
11
are each independently C
1
-C
12
linear or branched alkyl, preferably methyl or ethyl;
M is hydrogen or a salt forming cation, preferably sodium or potassium; x is an integer from 1 to 19;
j) an anionic unit having the formula:
—(CH
2
)
y
R
12
wherein R
12
is —SO
3
M, —OSO
3
M, —PO
3
M, —OPO
3
M, or mixtures thereof;
wherein M is hydrogen, one or more salt forming cations sufficient to satisfy charge balance, preferably sodium or potassium; or mixtures thereof; y is an interger from 1 to about 22;
k) and mixtures thereof;
R
3
and R
4
are each independently hydrogen, methyl, ethyl, propyl, phenyl, benzyl, and mixtures thereof.
The present invention also relates to laundry detergent compositions which comprise the pro-fragrance linear acetals and ketals described herein. A further aspect of the present invention is the use of the linear acetal and ketal pro-fragrances of the present invention as a post-laundry “freshening agent” for use on fabric which has been laundered but which has not been worn for an extended period of time. A yet further aspect of the present invention is the use of the pro-fragrances of the present invention in rinse-added compositions and in dryer-added compositions. These and other objects, features and advantages will become apparent to those of ordinary skill in the art from a reading of the following detailed description and the appended claims.
All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C.) unless otherwise specified. All documents cited are in relevant

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