Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-09-08
2001-05-29
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06239290
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention deals with novel emulsifiers that have excellent feel on the skin are essentially non-irritating to the eyes and skin and can be used to make unique silicone in water and water in silicone emulsions. The compounds are esters made by the reaction of sorbitol and carboxy functionalized silicone compounds. The introduction of the silicone portion of the molecule into the compounds of the present invention results in improved emulsification efficiency of silicone oils, improved oxidative stability and improved liquidity of the sorbitan esters as well as an outstanding skin feel of emulsions made with said emulsifiers. Emulsions made with standard sorbitan esters have a tendency to be sticky and cosmetically unappealing.
2. Description of the Art Practices
U.S. Pat. No. 5,296,625 to O'Lenick et al discloses silicone alkoxylated ester carboxylates. These carboxylates are not suitable to make sorbitan esters, since the linkage group from silicone to the carboxyl group is through an ester group. This group will hydrolyze in the presence of acid or base, and will transesterify if the attempt to react it with sorbitol is made.
Sorbitan esters have likewise been known for years. U.S. Pat. No. 2,322,821 describes the chemistry.
U.S. Pat. No. 6,013,813 issued Jan. 11, 2000 discloses guerbet based sorbitan esters. The guerbet gives improved oxidative stability over standard sorbitan esters, but does not address skin feel and the ability to provide very efficient emulsifiers for silicone oil.
U.S. Pat. No. 5,292,847 incorporated herein by reference issued in March 1994 discloses carboxy silicone alkoxylates. These carboxy silicones are raw materials in the preparation of the compounds of the present invention.
THE INVENTION
This invention relates to the use of a series of silicone functionalized sorbitan esters. The esters are made by the reaction of a silicone carboxylate and a sorbitol to make a new series of sorbitan esters.
Esters are a class of compounds which find applications in many diverse segments of the chemical industry. One of the problems which is encountered using non-branched fatty acids to make sorbitol based esters is the fact that the resulting products are dark in color and possess a mal odor. It is very desirable, particularly in cosmetic applications to have products that are light in color and free of bad odors.
The specific structure of the esters of the present invention determines the functional attributes of the product, including odor, color, emulsification and liquidity. The introduction of silicone into the backbone results in unexpectedly efficient emulsifiers for silicone, and emulsions with a cosmetically elegant skin feel.
REFERENCES:
patent: 5292847 (1994-03-01), O'Lenick
patent: 6013813 (2000-01-01), O'Lenick
patent: 6069259 (2000-05-01), Crivello
patent: 6096903 (2000-08-01), Moszner et al.
patent: 6121463 (2000-09-01), Parker et al.
Buffa Charles W.
O'Lenick, Jr. Anthony J.
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