IP Library › Granted Patent US 12,746,299
Granted Patent B2
US 12,746,299 · App. 18/270,508 · Granted Sep 29, 2026

Antimicrobial compounds based on glucoheptonic acids and their salts

Inventors: Peter Radford (Lenexa, KS); Diana Crain (Overland Park, KS); Larry Morris (Smithville, MO); Kevin Sikkema (Overland Park, KS); Amol Ashok Walke (Mapusa Bardez Goa, IN); Jose C. J. M. D. S. Menezes (Bicholim-Goa, IN); Prasanta Mayapur (Mapusa Bardez, IN)
Assignee: HARCROS CHEMICALS, INC.
A61L2/18A01N37/36A01N47/44
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Quick Facts
Patent No.
US 12,746,299
App. No.
18/270,508
Granted
Sep 29, 2026
Kind
B2
Abstract

The invention relates to methods for disinfecting or sanitizing. The invention is also directed to methods for the preparation of certain compounds useful as a disinfectant or sanitizer, such as glucoheptonic acid, chlorhexidine diglucoheptonate, benzalkonium glucoheptonate, and combinations thereof. The invention is still further directed to methods for evaluating a compound for performance in microbial disinfecting or sanitizing.

Claims (28)

1 . A method of disinfecting or sanitizing, wherein the method comprises:

contacting an aqueous composition comprising a component selected from the group consisting of chlorhexidine diglucoheptonate, benzalkonium glucoheptonate, and combinations thereof with a microbial population;

wherein, when the aqueous composition comprises chlorhexidine diglucoheptonate, the chlorhexidine diglucoheptonate comprises chlorhexidine di-α-glucoheptonate and chlorhexidine di-β-glucoheptonate and ratio of chlorhexidine di-β-glucoheptonate to chlorhexidine di-α-glucoheptonate is 1.5 or greater; and

wherein, when the aqueous composition comprises benzalkonium glucoheptonate, the benzalkonium glucoheptonate comprises 90% or greater of benzalkonium α-glucoheptonate.

2 . The method of claim 1 , wherein a Log Reduction of the microbial population is 3 or greater, 30 seconds after application.

3 . The method of claim 1 , wherein the aqueous composition further comprises glucoheptonic acid.

4 . The method of claim 3 , wherein the aqueous composition comprises α-glucoheptonic acid and β-glucoheptonic acid and the composition comprises an α-glucoheptonic acid concentration, based on total isomers of glucoheptonic acid, of 90% or greater.

5 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises from 60% to 75% chlorhexidine di-β-glucoheptonate (chlorhexidine di-β73-glucoheptonate).

6 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises 81% chlorhexidine di-β-glucoheptonate (chlorhexidine di-β81-glucoheptonate).

7 . The method of claim 1 , wherein the aqueous composition comprises benzalkonium glucoheptonate.

8 . The method of claim 1 , wherein the microbial population comprises C. albicans; S. aureus, S. epidermidis, E. coli, S. abony, L. monocytogenes , or combinations thereof.

9 . The method of claim 1 , wherein the microbial population comprises SARS-COV-2.

10 . The method of claim 7 , wherein the benzalkonium glucoheptonate is prepared by a method comprising:

combining a benzalkonium salt and a glucoheptonate salt in a container and stirring the combination;

wherein the glucoheptonate salt comprises 90% or greater of an α-glucoheptonate salt.

11 . The method of claim 1 , wherein the benzalkonium glucoheptonate comprises 96% or greater of benzalkonium α-glucoheptonate.

12 . The method of claim 1 , wherein the benzalkonium glucoheptonate comprises 98% or greater of benzalkonium α-glucoheptonate.

13 . The method of claim 1 , wherein the benzalkonium glucoheptonate comprises 99% or greater of benzalkonium α-glucoheptonate.

14 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises from 61% to 73% chlorhexidine di-β-glucoheptonate.

15 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises from 61% to 71% chlorhexidine di-β-glucoheptonate.

16 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises from 65% to 71% chlorhexidine di-β-glucoheptonate.

17 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises from 67% to 71% chlorhexidine di-β-glucoheptonate.

18 . The method of claim 1 , wherein the chlorhexidine diglucoheptonate comprises from 68% to 71% chlorhexidine di-β-glucoheptonate.

19 . A method of preparing chlorhexidine diglucoheptonate, the method comprising:

combining chlorhexidine and water to form a slurry; and

adding glucoheptonic acid to the slurry and mixing the combination;

wherein the glucoheptonic acid comprises α-glucoheptonic acid and β-glucoheptonic acid and ratio of β-glucoheptonic acid and α-glucoheptonic acid is 1.5 or greater.

20 . The method of claim 19 , wherein the chlorhexidine diglucoheptonate has a molar ratio of glucoheptonic acid to chlorhexidine of from 1.5:1 to 3:1.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2023
From: MENEZES, JOSE C.J. M.D.S.; WALKE, AMOL ASHOK; MAYAPUR, PRASANTA
To: ESTEEM INDUSTRIES PVT. LTD.
Reel/Frame 064122/0460 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2023
From: CRAIN, DIANA; MORRIS, LARRY; SIKKEMA, KEVIN; RADFORD, PETER
To: HARCROS CHEMICALS, INC.
Reel/Frame 064122/0484 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 30, 2023
From: ESTEEM INDUSTRIES PVT. LTD.
To: HARCROS CHEMICALS, INC.
Reel/Frame 064122/0509 →
Continuity (2)
Provisional Application 63133440 · Jan 4, 2021
Related Publication 20240197938A1 · Jun 20, 2024
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