Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use

• US 10,308,599 B2
• Filed: 12/06/2016
• Issued: 06/04/2019
• 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): Chen, Po-Chih
• Application Number:
  US15/370,658
• Publication Number:
  US 20170081281A1
• Time in Patent Office: 910 Days
• Field of Search: None
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• 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 47/10 Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
• CPC Class Codes: A61K 47/20 containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
• 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 9/06 Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels composition of ointments, creams or gels A61K47/00
• CPC Class Codes: C07C 331/20 of a saturated carbon skeleton

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

1. A compound represented by the structure of formula (IA):

2. The compound according to claim 1, wherein R₁ is the structure of formula (IIA).

3. The compound according to claim 2, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

4. The compound according to claim 1, wherein R₁ is the structure of formula (IIIA).

5. The compound according to claim 4, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

6. The compound according to claim 1, wherein R₁ is the structure of formula (IVA).

7. The compound according to claim 6, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

8. A compound represented by structure of formula (IB):

9. The compound according to claim 8, wherein R₁ is the structure of formula (IIB).

10. The compound according to claim 9, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

11. The compound according to claim 8, wherein R₁ is the structure of formula (IIIB).

12. The compound according to claim 11, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

13. The compound according to claim 8, wherein R₁ is the structure of formula (IVB).

14. The compound according to claim 13, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

15. A formulation, comprising:

a compound represented by the structure of formula (IB);

16. The formulation according to claim 15, wherein R₁ is the structure of formula (IIB).

17. The formulation according to claim 16, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

18. The formulation according to claim 15, wherein R₁ is the structure of formula (IIIB).

19. The formulation according to claim 18, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.

20. The formulation according to claim 15, wherein R₁ is the structure of formula (IVB).

21. The formulation according to claim 20, wherein R₂ is an aliphatic group containing 12 to 20 carbon atoms.