Antimicrobial compositions and articles and related methods

Patent metadata

Field	Value
Publication number	US-2024114905-A1
Application number	US-202218274779-A
Country	US
Kind code	A1
Filing date	Jan 28, 2022
Priority date	Jan 28, 2021
Publication date	Apr 11, 2024
Grant date	—

Abstract

The composition includes an antimicrobial monomer represented by formula CH2═C(R1)—C(O)—O-Q-N+(R)2CnH2n+1(X—), a non-fluorinated crosslinking monomer having at least two acrylate groups, methacrylate groups, or a combination thereof, a polar monomer having at least one of acrylic acid, methacrylic acid, or a carboxylate salt thereof, and a nonpolar monomer represented by formula CH2═C(R1)—C(O)—O—R2. The antimicrobial monomer, the non-fluorinated crosslinking monomer, the polar monomer, and the nonpolar monomer together account for greater than 95 percent by weight, based on the total weight of the composition. The article includes a film having a plurality of pendent groups represented by formula —C(O)—O-Q-N+(R)2CnH2n+1(X—) covalently bonded in a crosslinked non-fluorinated acrylic network. A method of making an article is also described.

First claim

1 . A composition comprising:
an antimicrobial monomer represented by formula CH 2 ═C(R 1 )—C(O)—O-Q-N + (R) 2 C n H 2n+1 (X—), wherein R 1 is hydrogen or methyl, Q is alkylene having up to six carbon atoms, each R is independently alkyl having up to four carbon atoms, n is an integer from 1 to 22, and X— is an anion; a non-fluorinated crosslinking monomer having at least two acrylate groups, methacrylate groups, or a combination thereof, wherein the crosslinker is present in an amount of greater than 30 percent by weight, based on the total weight of the composition; a polar monomer comprising at least one of acrylic acid, methacrylic acid, or a carboxylate salt thereof, wherein the polar monomer is present in an amount from 0 percent to 50 percent by weight, based on the total weight of the composition; and a nonpolar monomer represented by formula CH 2 ═C(R 1 )—C(O)—O—R 2 in an amount from 0 percent to 50 percent by weight, based on the total weight of the composition, wherein R 1 is hydrogen or methyl and R 2 is alkyl having from four to 18 carbon atoms;
wherein the antimicrobial monomer, the non-fluorinated crosslinking monomer, the polar monomer, and the nonpolar monomer together account for greater than 95 percent by weight, based on the total weight of the composition.

2 . The composition of claim 1 , wherein n is an integer from 12 to 16.

3 . The composition of claim 1 , wherein the non-fluorinated crosslinking monomer has at least three acrylate groups, methacrylate groups, or a combination thereof.

4 . The composition of claim 1 , wherein the non-fluorinated crosslinking monomer is present in an amount of at least 35 percent by weight, the polar monomer is present in an amount of at least 25 percent by weight, and the nonpolar monomer is present in an amount of 0 percent by weight.

5 . An article comprising a film comprising a plurality of pendent groups represented by formula —C(O)—O-Q-N + (R) 2 C n H 2n+1 (X—) covalently bonded in a crosslinked acrylic network, wherein Q is alkylene having up to six carbon atoms, each R is independently alkyl having up to four carbon atoms, n is an integer from 1 to 22, and X— is an anion, and wherein the crosslinked acrylic network is derived from the composition of claim 1 .

6 . The article of claim 5 , wherein the film has a surface comprising microstructures, nanostructures, or combinations thereof.

7 . An article comprising a film having a surface comprising microstructures, nanostructures, or combinations thereof, the film comprising a plurality of pendent groups represented by formula —C(O)—O-Q-N + (R) 2 C n H 2n+1 (X—) covalently bonded in a crosslinked non-fluorinated acrylic network, wherein Q is alkylene having up to six carbon atoms, each R is independently alkyl having up to four carbon atoms, n is an integer from 1 to 22, and X— is an anion.

8 . The article of claim 7 , wherein the crosslinked non-fluorinated acrylic network is derived from a composition comprising:
an antimicrobial monomer represented by formula CH 2 ═C(R 1 )—C(O)—O-Q-N + (R) 2 C n H 2n+1 (X—), wherein R 1 is hydrogen or methyl, Q is alkylene having up to six carbon atoms, each R is independently alkyl having up to four carbon atoms, n is an integer from 1 to 22, and X— is an anion; a non-fluorinated crosslinking monomer having at least two acrylate groups, methacrylate groups, or a combination thereof, wherein the crosslinker is present in an amount of greater than 25 percent by weight, based on the total weight of the composition; a polar monomer comprising at least one of acrylic acid, methacrylic acid, or a carboxylate salt thereof, wherein the polar monomer is present in an amount from 0 percent to 50 percent by weight, based on the total weight of the composition; and a nonpolar monomer represented by formula CH 2 ═C(R 1 )—C(O)—O—R 2 in an amount from 0 percent to 50 percent by weight, based on the total weight of the composition, wherein R 1 is hydrogen or methyl and R 2 is alkyl having from four to 18 carbon atoms.

9 . The article of claim 6 , wherein the microstructures, nanostructures, or combinations thereof comprise at least one of continuous peaks and adjacent valleys, pyramids, cones, hemispherical bumps, upstanding posts, or cube corners.

10 . The article of claim 6 , wherein the microstructures, nanostructures, or combinations thereof have a complement cumulative slope magnitude distribution such that at least 30 percent have a slope magnitude of at least 0.7 degrees, and at least 25 percent have a slope magnitude of less than 1.3 degrees.

11 . The article of claim 6 , further comprising a substrate having a first structured surface, wherein the first structured surface comprises microstructures, nanostructures, or combinations thereof, wherein the film is disposed on the first structured surface.

12 . The article of claim 11 , wherein the substrate comprises a fluoropolymer.

13 . The article of claim 11 , wherein substrate has a second surface opposite the first structured surface, and wherein the article further comprises a pressure sensitive adhesive disposed on the second surface of the substrate.

14 . The article of claim 6 , wherein the article further comprises an interior or exterior surface of a vehicle, a housing or case of an electronic device, or a furniture component.

15 . A process of making an article, the process comprising:
combining the composition of claim 1 with a photoinitiator, coating the resulting composition onto a substrate; and exposing the composition to actinic radiation to form a film.

16 . The process of claim 15 , wherein the substrate has a first structured surface, wherein the first structured surface comprises microstructures, nanostructures, or combinations thereof, and wherein the composition is coated on the first structured surface.

17 . The process of claim 15 , wherein the substrate comprises a tool having a negative replication of a surface comprising microstructures, nanostructures, or combinations thereof, the process further comprises removing the film from the tool.

18 . The process of claim 15 , further comprising thermoforming the article or the substrate.

19 . The article of claim 8 , wherein the polar monomer is present in an amount of at least 25 percent by weight based on the total weight of the composition, and wherein the nonpolar monomer is present in an amount of 0 percent by weight to 49 percent by weight, based on the total weight of the composition.

20 . The article of claim 8 , wherein the nanostructures are on the microstructures.

Assignees

• 3M Innovative Properties Company

Inventors

• Ali Mahfuza B
• Connell Jodi L
• Invie Judith M
• Stepanova Narina Y
• Hunt Bryan V
• Hebrink Timothy J

Classifications

• A01N37/44 Primary

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids · CPC title

• A01N25/10

  Macromolecular compounds · CPC title

• A01P1/00 Primary

  Disinfectants; Antimicrobial compounds or mixtures thereof · CPC title

• A01N33/12

  Quaternary ammonium compounds · CPC title