IP Library Granted Patent US 10,308,599
Granted Patent B2
US 10,308,599 · App. 15/370,658 · Granted Jun 4, 2019

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

Inventor: Michael E. Silver (Holland, MI)
Assignee: The William M. Yarbrough Foundation
C07C331/20A61K9/0014A61K9/06A61K31/145A61K31/198A61K31/26A61K45/06A61K47/10
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,308,599
App. No.
15/370,658
Granted
Jun 4, 2019
Kind
B2
Abstract

An isothiocyanate functional surfactant, wherein the protonated form of the surfactant includes the structure of formula (IA): wherein R 1 includes the structure of formula (IIA), (IIIA), or (IVA), wherein X includes an integer ranging from approximately 0 to approximately 20, wherein R 2 comprises a linear or branched aliphatic group containing approximately 8 to approximately 25 carbon atoms, and wherein R 3 comprises an aliphatic or aromatic group containing approximately 1 to approximately 20 carbon atoms and at least one—N═C═S group.

Claims (37)

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

wherein R 1 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 R 2 is a linear or branched aliphatic group containing 8 to 25 carbon atoms; and

wherein R 3 is an aliphatic or aromatic group containing 1 to 20 carbon atoms and at least one—N═C═S group.

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

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

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

5. The compound according to claim 4 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

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

7. The compound according to claim 6 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

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

wherein R 1 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 R 2 is a linear or branched aliphatic group containing 8 to 25 carbon atoms;

wherein R 3 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 + .

9. The compound according to claim 8 , wherein R 1 is the structure of formula (IIB).

10. The compound according to claim 9 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

11. The compound according to claim 8 , wherein R 1 is the structure of formula (IIIB).

12. The compound according to claim 11 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

13. The compound according to claim 8 , wherein R 1 is the structure of formula (IVB).

14. The compound according to claim 13 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

15. A formulation, comprising:

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

wherein R 1 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 R 2 is a linear or branched aliphatic group containing 8 to 25 carbon atoms;

wherein R 3 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.

16. The formulation according to claim 15 , wherein R 1 is the structure of formula (IIB).

17. The formulation according to claim 16 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

18. The formulation according to claim 15 , wherein R 1 is the structure of formula (IIIB).

19. The formulation according to claim 18 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

20. The formulation according to claim 15 , wherein R 1 is the structure of formula (IVB).

21. The formulation according to claim 20 , wherein R 2 is an aliphatic group containing 12 to 20 carbon atoms.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 3, 2017
From: SILVER, MICHAEL E.
To: THE WILLIAM M YARBROUGH FOUNDATION
Reel/Frame 041461/0610 →
Continuity (7)
Continuation In Part 15353260 · Nov 16, 2016
Continuation In Part 15297304 · Oct 19, 2016
Continuation 14594788 · Jan 12, 2015
Continuation 13342516 · Jan 3, 2012
Provisional Application 61502067 · Jun 28, 2011
Provisional Application 61429325 · Jan 3, 2011
Related Publication 20170081281A1 · Mar 23, 2017