Benzoate esters of hydroxyl terminated polyether...

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

Reexamination Certificate

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C556S445000, C424S070120, C424S078030

Reexamination Certificate

active

06552212

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates generally to improved ester compositions, and more particularly to novel benzoate esters of hydroxyl terminated polyether polysiloxane copolyols, their process of manufacture and their use as a cosmetic ingredient for toiletry and cosmetic formulations. The esters are useful for personal care cleansing products, such as skin and hair care products, and bar and liquid soaps.
2. Description of the Related Art
Esters and acids are known for a variety of different applications for cosmetic, pharmaceutical and medicinal purposes. Benzoate esters of certain alcohols and alcohol mixtures, and their uses are disclosed in assignee's U.S. Pat. Nos. 4,275,222, 4,322,545, 4,323,693, and 4,323,694 all to Scala, Jr.; U.S. Pat. Nos. 4,278,655, and 4,293,544 both to Elmi; and U.S. Pat. Nos. 5,271,930, 5270,421, and 4,791,097 all to Walele et al. The disclosures of these patents are incorporated herein by reference.
U.S. Pat. Nos. 5,807,545; 5,843,418, and 5,855,878 to Coffindaffer et al. disclose a vehicle system having a thickening system which comprises a nonionic long-chain alkylated water-soluble polymer and a specific cationic quaternary ammonium surfactant component dispersed in a compatible solvent. The vehicle system is used to deliver an active component to the hair or skin. Compositions containing said vehicle system may additionally contain a hair setting agent, a distributing aid, and a surfactant. Polysiloxanes and other silicone compounds are useful as hair conditioning components in the compositions of the invention.
U.S. Pat. No. 6,030,630 to Fleury et al. discloses a cosmetic composition for the hair and/or skin comprising at least one water-dispersible sulfonated copolyester containing polyorganosiloxane units incorporating a plurality of repeating sulfonated polyester units and polyorganosiloxane units.
U.S. Pat. No. 5,136,063 to O'Lenick, Jr. discloses silicone fatty esters prepared by esterification of a fatty carboxylic acid, ester or anhydride and a hydroxy containing silicone compound. Examples of suitable reactants are fatty acids such as lauric, myristic, stearic, oleic, and linoleic acid. These are esters of fatty acids, i.e., aliphatic long chain fatty carboxylic acids.
U.S. Pat. No. 5,166,297 to O'Lenick, Jr. discloses a dimethicone copolyol halo ester intermediate which is useful for reaction with amines to prepare silicone based quaternary compounds.
U.S. Pat. No.5,226,923 to O'Lenick, Jr. discloses processes for treating fiber with silicone fatty esters which act as conditioning agents for hair, skin, textile and other fibers. The silicone fatty esters are prepared by reacting the hydroxyl group in a silicone polymer with a fatty carboxylic acid, ester or anhydride, preferably in the presence of a catalyst. Examples of suitable reactants are fatty acids such as lauric, myristic, stearic, oleic, linoleic, and hydroxystearic.
U.S. Pat. No. 5292,847 To O'Lenick, Jr. discloses a series of silicone alkoxylates prepared by reacting a carboxy functional silicone and an ethylene oxide, propylene oxide or mixtures thereof. The products provide surfactant properties, specifically emulsification properties for many oil phases.
U.S. Pat. No. 5,296,625 to O'Lenick, Jr. et al. discloses a series of silicone alkoxylated esters which contain terminal carboxyl groups. The compounds are prepared by reacting the hydroxyl group in a silicone polymer with an anhydride. The compounds provide softening and lubrication when applied to fibers.
U.S. Pat. No. 5,378,787 to Vrckovnik et al. discloses a series of silicone reactive amino containing dimethicone copolyols. The amino silicone polymers are made by reacting an amino trialkoxy silane and a silanol to make an intermediate which is subsequently reacted with a dimethicone copolyol in the presence of alkaline catalyst. The reactive group is selected from silanol hydroxyl and optionally an alkoxy group.
U.S. Pat. No. 5,656,664 to O'Lenick, Jr. discloses esters prepared by reacting an alpha methyl alcohol and a fatty acid. A preferred ester is prepared using guerbet alcohols. The esters are useful as conditioning agents for skin.
U.S. Pat. Nos. 5,008,103 and 5,066,756 to Raleigh et al. disclose polysiloxane polymers containing organic polyether groups which are polysiloxane surface active agents for use in sun screen oils, antiperspirants, and the like.
U.S. Pat. No. 5,401,870 and 5,451,692 to Raleigh et al. disclose polysiloxane copolymers which are long chain hydrocarbon-modified polydiorganosiloxane polyoxyalkylene copolymers containing polydimethylsiloxy groups. The compounds are useful as emulsifiers in improved stability water-in-oil emulsions.
U.S. Pat. Nos. 5,658,558 and 5,939,058 to Schwartz disclose hair styling compositions containing at least one acrylic hair fixative resin and one or more plasticizing compounds selected from polycarboxylic acid esters and dimethicone copolyols.
U.S. Pat. No. 5,705,147 to Shapiro et al. discloses hair conditioning compositions comprising a mixture prepared by transesterification of a triglyceride with sucrose, and further comprising surfactants and optional ingredients such as polyether siloxane copolymers.
U.S. Pat. No. 5,710,113 to Wells discloses hair conditioning compositions containing a silicone fluid hair conditioning composition and silicone resin.
U.S. Pat. No. 6,022,547 to Herb et al. discloses a water-in-oil-in-water compositions including silicone-based surfactants comprising a dimethicone copolyol.
U.S. Pat. No. 4,654,161 to Kollmeier et al. discloses oxganopolysiloxanes that have one or more betaine groups, processes for their synthesis, and their use in cosmetic preparations.
U.S. Pat. No. 4,717,498 to Maxon et al. discloses dimethicone copolyol sulfosuccinate compounds obtained by reacting the ethoxylated polyether side chains of dimethicone copolyol with maleic anhydride to form a monester and then converting the monester to a sulfosuccinate by sulfonation of the double bond with a metallic sulfite, an amine or with a combination of a metallic sulfite and an amine. The compounds are useful as surfactants for improving the mildness and foam enhancing and stabilizing properties of shampoos and other personal care products.
U.S. Pat. No. 4,960,845 to O'Lenick, Jr. discloses sulfated silicone polymers which have the sulfate group on a pendant functionality rather than within the polymer backbone. The compounds provide a high level of foam in aqueous solution.
U.S. Pat. No. 5,070,168 to O'Lenick, Jr. discloses amino functional silicone polymers which have an ether amino pendant group. The compounds are prepared by introduction of an amino group on to the silicone pendant group. The compounds provide softness and lubrication to substrates.
U.S. Pat. No. 5,070,171 to O'Lenick, Jr. discloses organofunctional silicone polymers which have a phosphate pendant functionality present within the polymer. The phosphated silicone polymers are prepared by phosphation of a hydroxyl group on the silicone polymer.
U.S. Pat. No. 5,073,619 to O'Lenick, Jr. discloses organofunctional silicone polymers which have an amphoteric pendant functionality. The silicone amphoteric polymers are prepared by introduction of an amphoteric group by reaction of acrylic acid or methyl acrylate with a primary alkoxylated amine containing the silicone polymer. The compounds are good detergents and foaming agents.
U.S. Pat. No. 5,098,979 to O'Lenick, Jr. discloses quaternary silicone polymers useful in softening hair and fiber, and in conditioning skin. The compounds are silicone polymers which contain a quaternary nitrogen pendant group.
U.S. Pat. No. 5,120,812 to O'Lenick, Jr. discloses a vinyl silicone monomer which contains urethane functional groups, prepared by reaction of hydroxy containing silicone compounds with Benzene-1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl). The materials are used as intermediates in the preparation of polymers.
U.S. Pat. No.5,149,765 to

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