IP Library Granted Patent US 10,980,236
Granted Patent B2
US 10,980,236 · App. 16/940,159 · Granted Apr 20, 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 10,980,236
App. No.
16/940,159
Granted
Apr 20, 2021
Kind
B2
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 (29)

1. An aqueous antimicrobial coating composition comprising:

(a) a mixture from about 0.5 wt. % to about 0.75 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 consists essentially of triethanolamine.

4. The aqueous antimicrobial coating composition of claim 1 , comprising 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 2.44 wt. % 3-aminopropyltriethoxysilane.

5. The aqueous antimicrobial coating composition of claim 1 , comprising 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 4.87 wt. % 3-aminopropyltriethoxysilane.

6. The aqueous antimicrobial coating composition of claim 1 , comprising 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 12.18 wt. % 3-aminopropyltriethoxysilane.

7. The aqueous antimicrobial coating composition of claim 1 , comprising 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 7.31 wt. % 3-aminopropyltriethoxysilane.

8. The aqueous antimicrobial coating composition of claim 1 , comprising 0.75 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride; 7.31 wt. % 3-aminopropytriethoxysilane; 0.045 wt. % triethanolamine.

9. The aqueous antimicrobial coating composition of claim 1 , consisting essentially of 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 0.10 wt. % 3-chloropropyltrimethoxysilane; and 2.44 wt. % 3-aminopropyltriethoxysilane; remainder water.

10. The aqueous antimicrobial coating composition of claim 1 , consisting essentially of 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 0.10 wt. % 3-chloropropyltrimethoxysilane; and 4.87 wt. % 3-aminopropyltriethoxysilane; remainder water.

11. The aqueous antimicrobial coating composition of claim 1 , consisting essentially of 0.5 wt. % dimethyloctadecyl[3-(trihydroxysilyl)propyl]ammonium chloride and 0.10 wt. % 3-chloropropyltrimethoxysilane; and 12.18 wt. % 3-aminopropyltriethoxysilane; remainder water.

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

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

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

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

16. 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 0.5 wt. % to about 0.75 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 to form the antimicrobial coating on the surface,

wherein the resulting antimicrobial coating retains at least about 60% of its weight after exposure to 30-cycles of abrasion in a straight-line washability machine equipped with a 1 kg weighted boat wrapped in a water-moisturized wiper, and

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

17. The method of claim 16 , 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.

18. The method of claim 16 , wherein the at least one organic amine consists essentially of triethanolamine.

19. The method of claim 16 , wherein the applying comprises spray application of the aqueous antimicrobial coating composition to the surface.

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

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 Aug 18, 2020
From: GROSSMAN, GAVRI; FANG, JIE; ASGARI, PARHAM; BECK, VALERIE; EL-SAYED, MAHA; SHAHEEN, ELIAS
To: ALLIED BIOSCIENCE, INC.
Reel/Frame 053531/0743 →
Continuity (7)
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
Related Publication 20200352170A1 · Nov 12, 2020