IP Library Granted Patent US 11,033,031
Granted Patent B1
US 11,033,031 · App. 17/200,245 · Granted Jun 15, 2021

Broad spectrum antimicrobial coatings comprising combinations of organosilanes

Inventors: Gavri Grossman (Dallas, TX); Jie Fang (Carrollton, TX); Parham Asgari (Arlington, TX); Maha El-Sayed (Fremont, CA); Valerie Beck (Plano, TX); Elias Shaheen (Plano, TX)
Assignee: ALLIED BIOSCIENCE, INC.
A01N55/00A01N25/02A01N33/08A01N59/16A61L2/00B05D1/02B05D1/04B05D7/14B05D7/544C08G77/26C09D5/14C09D179/02C09D183/08C23C26/00C08K3/22C08K2003/2241C09D183/00
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Quick Facts
Patent No.
US 11,033,031
App. No.
17/200,245
Granted
Jun 15, 2021
Kind
B1
Abstract

An aqueous antimicrobial coating composition capable of forming an antimicrobial coating on a surface comprises at least two organosilanes, each of the at least two organosilanes having a structure, R—Si(OR′) 3 wherein R=—(CH 2 ) 3 —Y; Y= + —N(CH 3 ) 2 (C 18 H 37 )X − ; + —N(CH 3 ) 2 (C 14 H 29 )X − ; + —N(C 10 H 21 ) 2 (CH 3 )X − ; —Cl or —NH 2 ; X − =halide, sulfate, nitrate, phosphate, carbonate, organic sulfonate, organic carbonate, BF 4 − , or ClO 4 − ; and R′=H, methyl or ethyl, or a C 3 -C 6 straight-chained, branched or cyclic alkyl group, with the proviso that the organosilane R—Si(OR′) 3 having the C 3 -C 6 straight-chained, branched or cyclic alkyl group hydrolyzes in the aqueous antimicrobial coating composition to R—Si(OH) 3 .

Claims (28)

1. An aqueous antimicrobial coating composition comprising:

(a) a mixture from about 0.1 wt. % to about 1.0 wt. % of dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride (DMOD), 3-chloropropyltrimethoxysilane (CPTMS) and from about 2.5 wt. % to about 12.5 wt. % 3-aminopropyltriethoxysilane (APTES) in water; and

(b) optionally, at least one organic amine having a structure R 9 R 10 R 11 N, wherein R 9 , R 10 , and R 11 are independently H, alkyl, substituted alkyl, aryl, substituted aryl or cyclic, having a molecular weight of less than about 200 g/mole and a pKa of from about 7 to about 12,

wherein the aqueous antimicrobial coating composition exhibits an absorbance at 600 nm of less than about 0.2 after 4-weeks of ambient storage.

2. The aqueous antimicrobial coating composition of claim 1 , wherein the at least one organic amine is present at from about 0.01 wt. % to about 1.0 wt. %, based on the total weight of the aqueous antimicrobial coating composition.

3. The aqueous antimicrobial coating composition of claim 1 , wherein the at least one organic amine comprises triethanolamine.

4. The aqueous antimicrobial coating composition of claim 1 , comprising 0.045 wt. % triethanolamine.

5. The aqueous antimicrobial coating composition of claim 1 , comprising from about 0.01 wt. % to about 0.5 wt. % 3-chloropropyltrimethoxysilane.

6. The aqueous antimicrobial coating composition of claim 1 , comprising 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride.

7. The aqueous antimicrobial coating composition of claim 1 , comprising 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride.

8. The aqueous antimicrobial coating composition of claim 1 , consisting essentially of 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride; 0.12 wt. % 3-chloropropyltrimethoxysilane; 7.31 wt. % 3-aminopropyltriethoxysilane; 0.045 wt. % triethanolamine; remainder water.

9. The aqueous antimicrobial coating composition of claim 1 , consisting essentially of 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride; 0.15 wt. % 3-chloropropyltrimethoxysilane; 7.31 wt. % 3-aminopropyltriethoxysilane; and 0.045 wt. % triethanolamine; remainder water.

10. The aqueous antimicrobial coating composition of claim 1 , consisting essentially of 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride; 0.27 wt. % 3-chloropropyltrimethoxysilane; 7.31 wt. % 3-aminopropyltriethoxysilane; 0.045 wt. % triethanolamine; remainder water.

11. A method of forming an antimicrobial coating on a surface, the method comprising:

(a) applying an aqueous antimicrobial coating composition to the surface, the aqueous antimicrobial coating composition comprising:

(i) a mixture from about 0.1 wt. % to about 1.0 wt. % of dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride (DMOD), 3-chloropropyltrimethoxysilane (CPTMS), and from about 2.5 wt. % to about 12.5 wt. % 3-aminopropyltriethoxysilane (APTES) in water; and

(ii) optionally, at least one organic amine having a structure R 9 R 10 R 11 N, wherein R 9 , R 10 , and R 11 are independently H, alkyl, substituted alkyl, aryl, substituted aryl or cyclic, having a molecular weight of less than about 200 g/mole and a pKa of from about 7 to about 12; and

(b) allowing the aqueous antimicrobial coating composition to dry on the surface under ambient conditions, or drying the aqueous antimicrobial coating composition on the surface under heated conditions, to form the antimicrobial coating on the surface;

wherein the aqueous antimicrobial coating composition, prior to applying to the surface, exhibits an absorbance at 600 nm of less than about 0.2 after 4-weeks of ambient storage.

12. The method of claim 11 , wherein the at least one organic amine is present at from about 0.01 wt. % to about 1.0 wt. %, based on the total weight of the aqueous antimicrobial coating composition.

13. The method of claim 11 , wherein the at least one organic amine comprises triethanolamine.

14. The method of claim 11 , comprising 0.045 wt. % triethanolamine.

15. The method of claim 11 , comprising from about 0.01 wt. % to about 0.5 wt. % 3-chloropropyltrimethoxysilane.

16. The method of claim 11 , comprising 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride.

17. The method of claim 11 , comprising 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride.

18. The method of claim 11 , wherein the applying comprises spray application of the aqueous antimicrobial coating composition to the surface.

19. The method of claim 18 , wherein the spray application further comprises electrostatic spraying.

20. A method of stabilizing a high pH aqueous antimicrobial coating composition comprising from about 0.1 wt. % to about 1.0 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride (DMOD); from about 1.0 wt. % to about 15.0 wt. % 3-aminopropyltriethoxysilane (APTES); and from about 0.01 wt. % to about 1.0 wt. % triethanolamine (TEA) in water comprises adding from about 0.01 wt. % to about 0.5 wt. % 3-chloropropyltrimethoxysilane (CPTMS) to the aqueous coating composition, wherein the aqueous coating composition resulting therefrom exhibits an absorbance at 600 nm of less than about 0.2 after 4-weeks of ambient storage.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECT THE EXECUTION DATE FROM 01/11/2024 TO 11/01/2024 PREVIOUSLY RECORDED AT REEL: 69120 FRAME: 619. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Nov 20, 2024
From: SRFC BIO, INC.
To: TUCKER, JEFF
Reel/Frame 069405/0278 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 4, 2024
From: SRFC BIO, INC.
To: TUCKER, JEFF
Reel/Frame 069120/0619 →
CHANGE OF NAME Recorded May 27, 2022
From: ALLIED BIOSCIENCE, INC.
To: SRFC BIO, INC.
Reel/Frame 060205/0169 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2021
From: GROSSMAN, GAVRI; FANG, JIE; ASGARI, PARHAM; EL-SAYED, MAHA; BECK, VALERIE; SHAHEEN, ELIAS
To: ALLIED BIOSCIENCE, INC.
Reel/Frame 055580/0327 →
Continuity (7)
Continuation 16940159 · Jul 27, 2020
Continuation In Part 16591785 · Oct 3, 2019
Continuation In Part 15718997 · Sep 28, 2017
Division 15041974 · Feb 11, 2016
Continuation In Part 14932840 · Nov 4, 2015
Provisional Application 62114998 · Feb 11, 2015
Provisional Application 62075020 · Nov 4, 2014