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

Patent metadata

Field	Value
Publication number	US-10308599-B2
Application number	US-201615370658-A
Country	US
Kind code	B2
Filing date	Dec 6, 2016
Priority date	Jan 3, 2011
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

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.

First claim

What is claimed and desired to be secured by Letters Patent of the United States is:

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.

Assignees

• Silver Michael E
• The William M Yarbrough Found

Inventors

• Silver Michael E

Classifications

• A61K31/198

  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 title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61K31/26

  Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters · CPC title

• A61K9/0014

  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 title

• C07C331/20 Primary

  of a saturated carbon skeleton · CPC title