Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2002-11-04
2003-11-11
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C554S167000, C554S168000, C554S227000, C556S437000, C556S440000, C424S432000
Reexamination Certificate
active
06646144
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to cranberry seed oil derivatives derived by the reaction of dimethicone copolyol and cold pressed cranberry seed oil. The choice of cold pressed cranberry seed oil as a raw material in the preparation of the compounds of the present invention is critical, since it has been found that the cold pressed cranberry seed oil contains antioxidants, antimicrobial compounds and which when reacted with a water soluble or water dispersible silicone result in products that deliver said actives to the skin and hair, resulting in protection of the skin and hair from environmental factors such as acid rain, ozone attack and UV degradation.
U.S. Pat. No. 6,391,345 issued May 2002 describes the refining of cold pressed cranberry seed oil, and is incorporated herein by reference. American cranberries, Vaccinium macrocarpon, are native plants of open, acid peat bogs in North America. Cranberry plants are evergreen perennial vines that produce runners and upright branches with terminal flower buds.
Cranberries have historically been harvested and either ingested as whole berries, such as in cranberry sauce, or have been processed for their juice. Pulp remaining after cranberry juice extraction processing has historically been regarded as an undesirable waste product with little or no utility.
In the United States, cranberries are grown and are harvested in the Northeast, Northwest and Great Lakes regions. Cranberries ripen and are harvested in autumn, which has made cranberries a holiday food. Cranberries have not changed significantly in appearance and nutritional value over time. Cranberries have typically been stored by freezing or drying the whole berries.
Cranberries have become a popular food only in recent years because cranberries have a very bitter taste. Historically, processors have not dealt well with the taste. Cranberries are known to contain quininic acid. It is the quininic acid that imparts to cranberries, the bitter taste. Cranberry juice has become more palatable because it is blended with other sugar-containing aqueous liquids.
Apart from an undesirable taste, quininic acid is believed to have nutraceutical properties. When ingested, quininic acid is converted to hippuric acid. Hippuric acid is believed to remove toxins from the bladder, kidneys, prostate and testicles. Under normal circumstances, oils useful in the cosmetic industry are refined with a variety of steps that are designed to maximize triglyceride content, and minimize color and odor. These steps include steam distillation, a process in which steam is sparged through the oil to remove odor and color bodies and solvent extraction with compounds like hexane, which remove additional odor and color bodies. We have learned that these processes, while improving color and odor, remove many of the desirable “active” materials like tocopherols, antioxidants and the like. What results is a light color, low odor triglyceride with no appreciable added skin benefits. We have surprisingly learned that when the cranberry seed oil that is cold processed is reacted with specific water-soluble silicone compounds, the actives (normally removed in non-cold press process) remain in the product, become water-soluble and have outstanding activity on the skin. In essence two things happen when the cold pressed cranberry seed oil is reacted with dimethicone copolyol. First the triglyceride reacts with the hydroxyl group of the silicone compound, giving a water-soluble ester. Secondly, the water-soluble ester solubilized the active components there as a consequence of cold pressing. Thirdly, these very desirable materials are deposited on the skin by the silicone fatty ester, based upon its proclivity to remain on the skin. The result is a unique delivery of the actives to the skin from totally natural fruit oil.
Silicone esters are known materials. U.S. Pat. No. 4,724,248 issued February 1988 to Dexter et al is the first patent to disclose silicone fatty esters. O'Lenick et al in U.S. Pat. No. 5,136,063 issued Aug. 4, 1992 later expanded the field. However these patents did not disclose or suggest the possibility of using cold pressed cranberry seed oil that is rich in antioxidants and other actives that could be delivered to the skin using a specific silicone ester as a delivery molecule.
SUMMARY OF THE INVENTION
The present invention relates to a series of silicone compounds derived from the reaction of cold pressed cranberry oil and specific silicone compounds.
The present invention also relates to a process of treating hair and skin which comprises contacting the hair and skin with an effective anti-oxidant containing amount of a cranberry silicone compound of the preset invention.
DETAILED DESCRIPTION OF THE INVENTION
We have unexpectantly found that cranberry oil prepared by a cold press extraction process described in U.S. Pat. No. 6,391,345 issued May 2002, contain specific antioxidant materials that are removed by more aggressive refining processes like solvent extraction. These compounds surprisingly survive the reaction with dimethicone copolyol and result in a water-soluble delivery system for these very desirable natural compounds.
Also critical to the practice of the present invention is the fatty composition of the cold pressed cranberry oil. This cranberry oil has a substantially clear appearance with a pale yellow color.
Cold Pressed Cranberry Oil is a triglyceride conforming to the following structure:
The R—C(O)— group has the following composition:
Component
% Weight
16:0 palmitic
5.0 to 6.0
18:0 stearic
1.0 to 2.0
18:1 oleic
20 to 25
18:2 linoleic
35 to 40
18:3 linolenic (alpha)
30 to 35
20:0 arachidic
0.13
20:1 gadoleic
0.20
20:5 (n − 3)
0.32
22:2
1.1
Myristic
0.01
Pentadecanoic
0.02
Palmitoleic (trans)
0.13
Palmitoleic (cis)
0.08
10-heptadecanoic
0.03
Gamma linolenic
0.1 to 0.2
Nonadecanoic
0.1 to 0.2
11-transeicosenic
0.22
11,14 eicosandienoic
0.1
11,14,17 eicosatrienoic
0.01
Eicosapentaenoic
0.01
Behenic
0.03
Erucic
0.02
Docosapentaenoic
0.01
Tricosanoic
0.01
Lignoceric
0.02
Nervonic
0.02
The oil also contains the following very critical “active” components for skin and hair care:
Compound
mg/kg
Campesterol/brassicasterol (mg/kg)
66.0
Stigmasterol (mg/kg)
68.0
Beta-sitosterol (mg/kg)
1319.0
Phosphatidylinositiol (mg/kg)
9.9
Phosphatidylcholine (mg/kg)
202.0
Alpha-tocopherol (mg/kg)
341.0
Gamma-tocopherol (mg/kg)
110.0
When the oil is exposed to steam strip and solvent extraction the concentration of the “active” components drops to vanishingly small levels and the activity is lost.
As can be seen, the cold pressed cranberry seed oil is a rich source of compounds having important properties when applied to hair and skin. Stigmasterol is an anti-stiffness factor. Beta-sitosterol has use as an antihyperlipoproteinemic agent. One or more of the campesterol, stigmasterol and beta-sitosterol has inflammatory activity and may be useful in the treatment of gingivitis, rash, eczema, and other skin lesions. It is also believed that these compounds found in cranberry seed oil have activity as sunscreen agents. Since some of the compounds present in cranberry oil have absorbance in the UV-B range. It is this range that causes the greatest cellular damage. The cold pressed cranberry oil can shield against UV-A induced damage by scattering light as well as by light spectrum absorption. The cold pressed cranberry oil has, then activity as a broad spectrum UV protectant. The cranberry oil may be used alone or in combination with other conventional sunscreens.
The phosphatidylinositiol and phosphatidylcholine and tocopherols are highly desirable materials used on skin. The phosphatidylcholine, also known as lecithin, is found in human beings in the nervous system and the brain. Lecithin also has use as an edible and digestible surfactant. It is usable in manufacturing foods such as margarine and chocolate. Lecithin is a natural antioxidant that can increase oil stability and shelf life. Lecithin also has use in pharmaceutic
Klein Kenneth
O'Lenick, Jr. Anthony J.
Paleksky Irwin
Carr Deborah D.
Zenitech LLC
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