Isothiocyanate functional surfactant and associated method of use

• US 10,647,668 B2
• Filed: 06/04/2019
• Issued: 05/12/2020
• Est. Priority Date: 01/03/2011
• Status: Active Grant

• Current Assignee: The William M. Yarbrough Foundation
• Original Assignee: The William M. Yarbrough Foundation
• Inventors: Silver, Michael E.
• Primary Examiner(s): Neagu, Irina
• Application Number:
  US16/431,255
• Publication Number:
  US 20190284133A1
• Time in Patent Office: 343 Days
• Field of Search: 514514, 514562, 514563, 514625, 514663, 514665, 558 17
• CPC Class Codes: A61K 31/145 having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2) isothiourea A61K31/155
• CPC Class Codes: A61K 31/198 Alpha-amino acids, e.g. alanine or edetic acid [EDTA] betaine A61K31/205; proline A61K31/401; tryptophan A61K31/405; histidine A61K31/4172; peptides not degraded to individual amino acids A61K38/00
• CPC Class Codes: A61K 31/26 Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 47/24 containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
• CPC Class Codes: A61K 47/34 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers A61K47/10 takes precedence
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/0019 Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner non-active ingredients are additionally classified in A61K47/00
• CPC Class Codes: C07C 331/20 of a saturated carbon skeleton

Abstract

A method for treating phytophotodermatitis including the steps of applying an isothiocyanate functional surfactant to an area affected by phytophotodermatitis, wherein said isothiocyanate functional surfactant comprises at least one isothiocyanate functional group associated with an aliphatic and/or aromatic carbon atom of the isothiocyanate functional surfactant.

Claims

1. An isothiocyanate functional surfactant, comprising:

a lysine derivative having an α

-nitrogen and an ε

-nitrogen, and wherein an alkyl substituent comprising at least 8 carbon atoms is bound to the α

-nitrogen, and further wherein the ε

-nitrogen forms part of an isothiocyanate functional group.

2. The isothiocyanate functional surfactant according to claim 1, in combination with an additional surfactant selected from at least one of the group comprising a non-ionic surfactant, an anionic surfactant, a cationic surfactant, a zwitterionic surfactant, and combinations thereof.

3. The isothiocyanate functional surfactant according to claim 2, wherein the additional surfactant comprises a non-ionic surfactant.

4. The isothiocyanate functional surfactant according to claim 3, wherein the non-ionic surfactant is selected from at least one of the group comprising alcohols, alkanolamides, amine oxides, esters, glycerides, ethoxylated glycerides, polyglyceryl esters, sorbitan esters, carbohydrate esters, ethoxylated carboxylic acids, phosphoric acid triesters, ethers, ethoxylated alcohols, alkyl glucosides, ethoxylated polypropylene oxide ethers, alkylated polyethylene oxides, alkylated polypropylene oxides, alkylated PEG/PPO copolymers, and combinations thereof.

5. The isothiocyanate functional surfactant according to claim 2, wherein the additional surfactant comprises an anionic surfactant.

6. The isothiocyanate functional surfactant according to claim 5, wherein the anionic surfactant is selected from at least one of the group comprising taurates, isethionates, alkyl sulfates, alkyl ether sulfates, succinamates, alkyl sulfonates, alkylaryl sulfonates, olefin sulfonates, alkoxy alkane sulfonates, salts of fatty acids derived from natural plant and/or animal sources and/or synthetically prepared, alkylated ammonium salts of alkylated and/or acylated amino acids and/or peptides, alkylated sulfoacetates, alkylated sulfosuccinates, acylglyceride sulfonates, alkoxyether sulfonates, phosphoric acid esters, phospholipids, and combinations thereof.

7. The isothiocyanate functional surfactant according to claim 2, wherein the additional surfactant comprises a cationic surfactant.

8. The isothiocyanate functional surfactant according to claim 7, wherein the cationic surfactant is selected from at least one of the group comprising alkylated quaternary ammonium salts R₄NX, alkylimidazolines, alkoxylated amines, and combinations thereof.

9. The isothiocyanate functional surfactant according to claim 2, wherein the additional surfactant comprises a zwitterionic surfactant.

10. The isothiocyanate functional surfactant according to claim 9, wherein the zwitterionic surfactant is selected from at least one of the group comprising betaines, sultaines, hydroxysultaines, amido betaines, amidosulfo betaines, and combinations thereof.