# US 10,308,599 B2 · Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,308,599 B2 - Document ID: US10308599B2 - Status: Granted - Kind: B2 - Application number: 15/370,658 - Filed: 2016-12-06 - Published: 2017-03-23 - Granted: 2019-06-04 - Earliest claimed: 2011-01-03 - Assignees: The William M. Yarbrough Foundation - Applicants: Michael E. Silver - Inventors: Michael E. Silver - Web page: https://patentgrep.com/patent/US10308599B2 ## CPC - C07C 331/20: of a saturated carbon skeleton - 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)} - A61K 9/06: Ointments; Bases therefor; {Other semi-solid forms, e.g. creams, sticks, gels (composition of ointments, creams or gels A61K47/00)} - 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) - 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) - A61K 31/26: Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers - A61K 47/20: containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract An isothiocyanate functional surfactant, wherein the protonated form of the surfactant includes the structure of formula (IA): wherein R1 includes the structure of formula (IIA), (IIIA), or (IVA), wherein X includes an integer ranging from approximately 0 to approximately 20, wherein R2 comprises a linear or branched aliphatic group containing approximately 8 to approximately 25 carbon atoms, and wherein R3 comprises an aliphatic or aromatic group containing approximately 1 to approximately 20 carbon atoms and at least one—N═C═S group. ## Claims ### Claim 1 A compound represented by the structure of formula (IA): wherein R1 is selected from the group consisting of the structures of formula (IIA), (IIIA), and (IVA); wherein X is an integer ranging from 1 to 20; wherein R2 is a linear or branched aliphatic group containing 8 to 25 carbon atoms; and wherein R3 is an aliphatic or aromatic group containing 1 to 20 carbon atoms and at least one—N═C═S group. ### Claim 2 (depends on 1) The compound according to claim 1, wherein R1 is the structure of formula (IIA). ### Claim 3 (depends on 2) The compound according to claim 2, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 4 (depends on 1) The compound according to claim 1, wherein R1 is the structure of formula (IIIA). ### Claim 5 (depends on 4) The compound according to claim 4, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 6 (depends on 1) The compound according to claim 1, wherein R1 is the structure of formula (IVA). ### Claim 7 (depends on 6) The compound according to claim 6, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 8 A compound represented by structure of formula (IB): wherein R1 is selected from the group consisting of the structures of formula (IIB), (IIIB), and (IVB); wherein X is an integer ranging from 0 to 20; wherein R2 is a linear or branched aliphatic group containing 8 to 25 carbon atoms; wherein R3 is an aliphatic or aromatic group containing 1 to 20 carbon atoms and at least one—N═C═S group; and wherein M+ is selected from the group consisting of Li+, Na+, K+, and H+. ### Claim 9 (depends on 8) The compound according to claim 8, wherein R1 is the structure of formula (IIB). ### Claim 10 (depends on 9) The compound according to claim 9, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 11 (depends on 8) The compound according to claim 8, wherein R1 is the structure of formula (IIIB). ### Claim 12 (depends on 11) The compound according to claim 11, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 13 (depends on 8) The compound according to claim 8, wherein R1 is the structure of formula (IVB). ### Claim 14 (depends on 13) The compound according to claim 13, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 15 A formulation, comprising: a compound represented by the structure of formula (IB): wherein R1 is selected from the group consisting of the structures of formula (IIB), (IIIB), and (IVB); wherein X is an integer ranging from 1 to 20; wherein R2 is a linear or branched aliphatic group containing 8 to 25 carbon atoms; wherein R3 is an aliphatic or aromatic group containing 1 to 20 carbon atoms and at least one—N═C═S group; wherein M+ is selected from the group consisting of Li+, Na+, K+, and H+; and a non-hygroscopic solvent. ### Claim 16 (depends on 15) The formulation according to claim 15, wherein R1 is the structure of formula (IIB). ### Claim 17 (depends on 16) The formulation according to claim 16, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 18 (depends on 15) The formulation according to claim 15, wherein R1 is the structure of formula (IIIB). ### Claim 19 (depends on 18) The formulation according to claim 18, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms. ### Claim 20 (depends on 15) The formulation according to claim 15, wherein R1 is the structure of formula (IVB). ### Claim 21 (depends on 20) The formulation according to claim 20, wherein R2 is an aliphatic group containing 12 to 20 carbon atoms.