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US 2012/0059056 A1Published application
Carbonate derivatives as skin care
AssigneeEastman Chemical Company
InventorNeil Warren Boaz
Life of this patent
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Abstract
Carbonates of anti-aging ingredients, in particular anti-oxidants and skin illuminating phenol ingredients, have been prepared as derivatives of these ingredients with enhanced physical properties. It has been demonstrated that these carbonates will hydrolyze under enzymatic catalysis to release the parent ingredient. In contrast, esters of the phenolic groups in many cases do not hydrolyze under the same conditions.
Claims22
An alkyl carbonate having the general structure 1:
- wherein R is selected from substituted and unsubstituted, branched- and straight-chain, saturated, unsaturated, and polyunsaturated C1-C22 alkyl, and R1, R2, R3, R4, and R5 are independently selected from hydrogen;
- substituted and unsubstituted, branched- and straight-chain saturated C4-C22 alkyl;
- substituted and unsubstituted, branched- and straight-chain C2-C22 alkenyl;
- substituted and unsubstituted, branched- and straight-chain C2-C22 alkynyl;
- substituted and unsubstituted, branched- and straight-chain C4-C22 dienyl;
- substituted and unsubstituted, branched- and straight-chain C6-C22 trienyl;
- C1-C6-alkoxy;
- carboxyl;
- C1-C15 aminocarbonyl;
- C1-C15 amido;
- cyano;
- C2-C15-alkoxycarbonyl;
- C2-C15-alkoxycarbonyloxy;
- C2-C15-alkanoyloxy;
- hydroxyl;
- aryl;
- heteroaryl;
- thiol;
- thioether;
- and halogen.
17 more elements
The process of producing an alkyl carbonate having the general structure 1:
- wherein R is selected from substituted and unsubstituted, branched- and straight-chain, saturated, unsaturated, and polyunsaturated C1-C22 alkyl. and R1, R2, R3, R4, and R5 are independently selected from hydrogen, substituted and unsubstituted, branched- and straight-chain saturated, C4-C22 alkyl, substituted and unsubstituted, branched- and straight-chain C2-C22 alkenyl, substituted and unsubstituted, branched- and straight-chain C2-C22 alkynyl, substituted and unsubstituted, branched- and straight-chain C4-C22 dienyl, substituted and unsubstituted, branched- and straight-chain C6-C22 trienyl, C1-C6-alkoxy, carboxyl, C1-C15 aminocarbonyl, C1-C15 amido, cyano, C2-C15-alkoxycarbonyl, C2-C15-alkoxycarbonyloxy, C2-C15-alkanoyloxy, hydroxy, aryl, heteroaryl, thiol, thioether, and halogen, comprising reacting at least one alcohol of Formula 4:
- with a chloroformate, bromoformate, or dicarbonate to produce said alkyl carbonate of Formula 1.
Dependencies are inferred from the claim text.