Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2001-06-04
2001-11-06
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C556S437000, C556S438000, C556S439000, C514S063000, C424S070800, C424S070120, C424S078020, C424S078030
Reexamination Certificate
active
06313329
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to composition of matter of certain eugenol functionalized silicone polymers useful to make substantive delivery systems for eugenol to the skin. Eugenol applied to the skin is an effective herbal remedy for a variety of conditions including male pattern baldness.
BACKGROUND AND ART
Clove bud oil has long been used as a herbal remedy. The oil is distilled from the dried-flower buds. It is used in many natural-based toothpastes. It is also a strong insect repellent, and especially useful as a moth repellent. Clove bud oil is a strong antiseptic, anti-spasmodic. Clove bud is also anti viral, anti fungal and healing, and the second most powerful essential oil-directly behind Tea tree oil (melaleuca alternifolia). Clove bud oil has wonderful soothing and calming aromatherapy benefits.
This particular oil comes from the buds of cloves which are known worldwide as a domestic spice. The oil has been used traditionally to remedy skin infections and to reduce digestive upsets. It is also used to kill intestinal parasites and to aid in childbirth. A tea that is made from cloves is often used to relieve nausea. In Chinese history the bud oil has been used for the symptoms above as well as for diarrhea, hernias, bad breath and bronchitis.
The oil can be used to reduce acne, athlete's foot and pain from burns. It has also been found that the oil is a very effective insect repellent and will relieve the pain of most toothaches, ulcers and wounds. The vapors of this oil are found to have beneficial effects on arthritis, rheumatism and most sprains.
The vapor generated from this oil are attributed to eugenol, a volatile material that is very difficult to deliver to the skin as a pure compound. The incorporation of eugenol into a silicone ester having differing amount of polyoxyalkylene groups results in a delivery system for the eugenol that makes delivery of the volatile portion possible.
DESCRIPTION OF THE INVENTION
OBJECTIVE OF THE INVENTION
It is the object of the invention to provide silicone functionalized eugenol esters that provide a mechanism by which eugenol can be delivered over time by hydrolysis of the ester bond linking it to silicone.
SUMMARY OF THE INVENTION
The compounds of the present invention conform to the following structure:
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20;
R is:
DETAILED DESCRIPTION OF THE INVENTION
The silicone esters of the present invention are made by the reaction of eugenol and certain methyl ester containing silicone compounds.
Eugenol conforms to the following structure:
The OH group is reacted with a carboxy methyl ester silicone conforming to the following structure:
To give the desired compounds:
wherein;
a is an integer ranging from 0 to 2000;
b is an integer ranging from 1 to 20;
c is an integer ranging from 1 to 20;
d is an integer ranging from 0 to 20;
n is an integer ranging from 10 to 20;
x is an integer ranging 0 to 20;
y is an integer ranging 0 to 20;
z is an integer ranging 0 to 20;
R is
It should be clear that the compounds of the present invention offer the possibility of making delivery products that can be used in many different applications areas. Products can be made with varying solubility in water, silicone compounds, and oil. The different solubilities of the compounds come by changing the values of “a”, “c” and “d” in the molecule. By increasing the value of “a” increased silicone solubility is achieved. By increasing the value of“c”, increased water solubility is achieved. Alternatively, by increasing the values of “x”, “y” and “z” differing water solubility can be achieved. Finally, by increasing the value of“d”, the oil solubility will increase. Interestingly, by increasing the value of “b” the amount of active eugenol in the molecule will increase.
The ability to place the compound into any solvent desired allow for the formulation of products for many personal care applications.
The silicone ester derivative of eugenol as contemplated by this invention has improved substantivity to hair, skin and as such is not prone to wash off these substrates. The fact that the compounds of the present invention are esters makes them slowly hydrolyze to release the very eugenol molecule that is the active ingredient.
The amount of silicone eugenol ester necessary to properly effectuate the desired characteristics to the hair and skin ranges from a ratio of wt % between the substrate and the weight of silicone ester should be from about 100:0.01 to about 100:1. Preferably, this range is from about 100:0.03 to about 100:0.6, and most preferably from about 100:0.1 to about 100:0.25.
REFERENCES:
patent: 5136063 (1992-08-01), O'Lenick, Jr.
patent: 5296625 (1994-03-01), O'Lenick, Jr. et al.
patent: 6114561 (2000-09-01), O'Lenick, Jr.
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