Croda International, Inc.

Givaudan S.a.

Croda Americas LLC

Hanamanthsa Shankarsa Bevinakatti

Alan Geoffrey Waite

Christopher P Newman

Trevor Graham Blease

Neil Grainger

Simon Ellwood

William Harry McNamee

Christian Joseph Dederen

Johny Denis Grade

Fabio Arico

Pietro Tundo

Martin Schroeder

Tracey Joanne Wardell

Stuart Jackson

Caroline L Kelly

Jackie Frank

Johnny Denis Grade

Thomas Phillip Wells

William Harry Manamee

Christian J Dederen

Caroline Louise Kelly

The invention relates to novel demulsifiers for use in the demulsification of oils from water and vice versa, including the demulsification of crude oil from sea water or brine. In particular, the present invention relates to novel demulsifiers which are environmentally friendly, or 'green', and which can be used without restriction on-site in offshore oil drilling fields, for example in the North Sea. The novel demulsifiers are based on the reaction product of alkoxylated polyols or polyol esters with dicarboxylic acids.

Demulsifiers

Polyester oil structurants are obtainable by the reaction of a Cto CQ dicarboxylic acid, a polyol and a Cto C, particularly a Cto C, monocarboxylic fatty acid. The structurants can be used to provide structure, particularly thickening and/or gelling, in oils of a wide range of polarity. Thickened oils can find application in a range of personal care and other applications.

Structurants for oil phases

A compound of the formula R.[(AO).&#x2014;R](I) where: Ris the residue of a group having at least m active hydrogen atoms; AO is an alkylene oxide residue; each n is independently from 1 to 100; m is at least 2; and each Ris independently H, a Cto Chydrocarbyl, or an acyl group &#x2014;OC.R, where Ris a Cto Chydrocarbyl group, wherein on average greater than one of the Rgroups is or comprises a Cto Chydrocarbyl group comprising at least two ethylenic double bonds. The compounds are particularly suitable for use in preparing aqueous emulsions or dispersions of resins and polymers, especially alkyd resins.

Surfactant

Polyglycerol carboxylic acid esters are made by reaction of a, typically Cto C, particularly Cto C, carboxylic acid with glycerol carbonate, particularly with base catalyst, and desirably at temperatures from 170&#xb0; C. to 250&#xb0; C. Other carbonates e.g. cyclic diol carbonates such as ethylene or propylene carbonates, may be used in combination with the glycerol carbonate to make novel mixed polymeric esters. The molar ratio of carboxylic acid group to glycerol carbonate is typically from 2 to 30, but can be up to 100. The base catalyst is desirably alkali metal hydroxide, carbonate or alkoxide. The reaction is desirably carried out in an inert atmosphere, and reducing agent such as phosphorous acid, hypophosphorous acid or borohydride and/or activated carbon, may be included to improve product color.

Method of making polyglycerol esters

A surfactant composition contains at least one sorbitan ester and at least one sorbitol ester wherein the mean number of carbon atoms of the hydrophobe of the sorbitan ester is greater than that of the sorbitol ester. The surfactant composition is particularly suitable for use in stabilizing emulsions, especially personal care or cosmetic products.

Surfactant composition

Fatty esters of oligoesters of a dicarboxylic acid and a polyol retaining at least one free hydroxyl group, particularly of the formula (I): R&#x2014;[ORO&#x2014;C(O)&#x2014;R&#x2014;(O)C&#x2014;]&#x2014;R(I), where Ris H, a monocarboxylic acid group, or RO&#x2014;[C(O)&#x2014;R&#x2014;(O)C]&#x2014;; Rs are residues of polyols having at least one substituent free hydroxyl; Rs are hydrocarbylene; Ris &#x2014;OH, &#x2014;OM where M is a salt forming metal, amine or ammonium, &#x2014;OR, or &#x2014;ORO&#x2014;R; Ris Cto Chydrocarbyl; Ris Cto Chydrocarbyl; Ris H, or &#x2014;C(O)R; and m is 1 to 20; provided that at least one of Rand Ris or includes a Cto Cgroup, are surfactants. A range of surfactant properties can be obtained by varying the molecules within these ranges. Especially where Ris derived from a higher polyol e.g. sorbitol, Ris Cto C, and the fatty terminal group is Cto C, the products can be highly water soluble and effective oil in water emulsifiers.

Surfactant compounds

A process of preparing cyclic ethers is described. The process involves the reaction of at least one organic compound such as a dioi or a polyol which it has at least one pair of hydroxyl groups separated by 4 or 5 carbon atoms, and which is capable of being converted into an ether linkage, with an organic carbonate in the presence of a base. The base is an alkoxy, a carbonate or a hydroxide base or is a mixture of such bases. At least one of the hydroxyl groups of the organic compound is not a tertiary hydroxyl group.

Cyclic ethers

Oligoesters including residues of alk(en)yl succinic anhydrides and polyols having at least 3 OH groups, optionally further esterified with fatty acid residues are surfactants which can be used for emulsifiers or similar uses. The surfactants are usually made from Cto Calk(en)yl succinic anhydride and polyols having at least 4 hydroxyl groups and are particularly of the formula (I): R&#x2014;[ORO(O)C.C(HR).(HR)C.C(O)]&#x2014;R(I), where R, R, R, R, R, R, Rand m have defined meanings. The surfactants are useful as emulsifiers, particularly oil in water emulsifiers.

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Ingleby Barwick, United Kingdom

Hanamanthsa Shankarsa Bevinakatti