Task specific ionic liquid-impregnated polymeric surface coatings for antibacterial, antifouling, and metal scavenging activity

Patent metadata

Field	Value
Publication number	US-11045833-B2
Application number	US-201816482954-A
Country	US
Kind code	B2
Filing date	Feb 5, 2018
Priority date	Feb 3, 2017
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

Disclosed are polymer-coated surfaces encapsulating task specific ionic liquids (ILs), IL complexes, or oils. Also disclosed are polymer-coated surfaces, wherein the polymer comprises ILs or neutral ethylene diamine compounds. Also disclosed are methods of antimicrobial treatment, metal remediation, and gas absorption using polymer coatings encapsulating ILs, IL complexes, and oils or polymer coatings comprising ILs and neutral ethylene diamine compounds.

First claim

The invention claimed is:

1. A method of coating a surface of an object, a device, or an assembly, comprising the steps of:
(a) providing in a partially evacuated vessel an object, a device, or an assembly comprising a surface;
(b) heating or irradiating a free radical initiator, thereby producing a gaseous free radical initiator;
(c) introducing into the partially evacuated vessel one or more gaseous monomers and the gaseous free radical initiator, thereby forming a cross-linked coating on the surface; and
(d) contacting the cross-linked coating with an ionic liquid comprising a cation and an anion; thereby forming the coating on the surface of the object, the device, or the assembly;
wherein the cation is represented by:
structural formula I:

wherein, independently for each occurrence:
R 1 is —(C(R) 2 ) n -;
n is 2, or 3;
R 2 is —(C(R) 2 ) m -R″;
m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and
R is H, F, C 1 -C 3 alkyl, or C 1 -C 3 fluoroalkyl;
R′ is H, F, C 1 -C 8 alkyl, or C 1 -C 8 fluoroalkyl; and
R″ is H, F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, C 1 -C 3 fluoroalkyloxy, C 6 -C 10 aryl, C 2 -C 8 alkenyl or C 2 -C 8 fluoroalkenyl; wherein each instance of C 6 -C 10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, and C 1 -C 3 fluoroalkyloxy, or
structural formula II:

wherein, independently for each occurrence:
R 1 is —(C(R) 2 ) n -;
n is 2, or 3;
R 2 is —(C(R′) 2 ) m -R″;
m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and
R is H, F, C 1 -C 3 alkyl, or C 1 -C 3 fluoroalkyl;
R′ is H, F, C 1 -C 8 alkyl, or C 1 -C 8 fluoroalkyl; and
R″ is H, F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, C 1 -C 3 fluoroalkyloxy, C 6 -C 10 aryl, C 2 -C 8 alkenyl or C 2 -C 8 fluoroalkenyl; wherein each instance of C 6 -C 10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, and C 1 -C 3 fluoroalkyloxy.

2. The method of claim 1 , wherein the cation is represented by structural formula I:

wherein, independently for each occurrence:
R 1 is —(C(R) 2 ) n -;
n is 2, or 3;
R 2 is —(C(R′) 2 ) m -R″;
m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and
R is H, F, C 1 -C 3 alkyl, or C 1 -C 3 fluoroalkyl;
R′ is H, F, C 1 -C 8 alkyl, or C 1 -C 8 fluoroalkyl; and
R″ is H, F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, C 1 -C 3 fluoroalkyloxy, C 6 -C 10 aryl, C 2 -C 8 alkenyl or C 2 -C 8 fluoroalkenyl; wherein each instance of C 6 -C 10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, and C 1 -C 3 fluoroalkyloxy.

3. The method of claim 1 , wherein the the cation is represented by structural formula II:

wherein, independently for each occurrence:
R 1 is —(C(R) 2 ) n -;
n is 2, or 3;
R 2 is —(C(R′) 2 ) m -R″;
m is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and
R is H, F, C 1 -C 3 alkyl, or C 1 -C 3 fluoroalkyl;
R′ is H, F, C 1 -C 8 alkyl, or C 1 -C 8 fluoroalkyl; and
R″ is H, F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, C 1 -C 3 fluoroalkyloxy, C 6 -C 10 aryl, C 2 -C 8 alkenyl or C 2 -C 8 fluoroalkenyl; wherein each instance of C 6 -C 10 aryl is optionally substituted with one, two, three, four or five substituents independently selected from the group consisting of F, C 1 -C 3 alkyl, C 1 -C 3 fluoroalkyl, C 1 -C 3 alkyloxy, and C 1 -C 3 fluoroalkyloxy.

4. The method of claim 1 , wherein the ionic liquid comprises water.

5. The method of claim 1 , wherein the free radical initiator is selected from the group consisting of a peroxide, an aryl ketone, and an azo compound.

6. The method of claim 1 , wherein the free radical initiator comprises triethylamine.

7. The method of claim 1 , wherein the free radical initiator is an azo compound selected from the group consisting of 4,4′-Azobis( 4 -cyanovaleric acid), 4,4′-Azobis(4-cyanovaleric acid), 1,1′-Azobis(cyclohexanecarbonitrile), 2,2′-Azobis(2-methylpropionamidine) dihydrochloride, 2,2′-Azobis(2-methylpropionitrile), and 2,2′-Azobis(2-methylpropionitrile).

8. The method of claim 1 , wherein the free radical initiator is a peroxide selected from the group consisting of tent-butyl hydroperoxide, tent-butyl peracetate, cumene hydroperoxide, dicumyl peroxide, benzoyl peroxide, tent-amyl peroxide, tent-butyl peroxide, and tent-butyl peroxybenzoate.

9. The method of claim 1 , wherein the monomer is at least one of an acrylate, an acrylamide, a siloxane, a silane, and a vinyl compound.

10. The method of claim 1 , wherein the one or more monomers are selected from the group consisting of methyl methacrylate, butyl acrylate, glycidal methacrylate, hydroxyl ethyl methacrylate, ethylene glycol diacrylate, propargyl methacrylate, pentafluorophenyl methacrylate, hydroxyethyl methacrylate, cyclohexyl methacrylate, methacrylic acid-co-ethyl acrylate, 1H,1H,6H,6H-perfluorohexyldiacrylate, 1H,2H,2H-perfluorooctyl acrylate, 1H,2H,2H-perfluorodecyl acrylate, N,N-dimethylacrylamide, polydimethylacrylamide, 2-vinyl pyridine, 4-vinyl pyridine, p-divinylbenzene, m-divinylbenzene, trivinlytrimethylcyclotri siloxane, tetravinyltetramethylcyclotetra-siloxane, trichlorovinylsilane, di(ethylene glycol) divinyl ether, xylylene, vinylene, dimethylaminomethyl styrene, pyrrole, 3-thiopheneacetic acid, and copolymers thereof.

11. The method of claim 1 , wherein the one or more monomers are selected from N,N-dimethylacrylamide, polydimethylacrylamide, trichlorovinylsilane, and di(ethylene glycol) divinyl ether.

12. The method of claim 1 , wherein each n is 2.

13. The method of claim 1 , wherein each n is 2; and each R is H.

14. The method of claim 1 , wherein each m is 6; and each R″ is H.

15. The method of claim 1 , wherein each R 2 is 2-ethylhexyl.

16. The method of claim 1 , wherein the anion is boron tetrafluoride, phosphorus tetrafluoride, phosphorus hexafluoride, alkylsulfonate, fluoroalkylsulfonate, arylsulfonate, bis(alkyl sulfonyl)amide, bis(fluoroalkylsulfonyl)amide, bis(arylsulfonyl)amide, (fluoroalkylsulfonyl)(fluoroalkylcarbonyl)amide, halide, nitrate, nitrite, sulfate, hydrogensulfate, alkyl sulfate, aryl sulfate, carbonate, bicarbonate, carboxylate, phosphate, hydrogen phosphate, dihydrogen phosphate, hypochlorite, or an anionic site of a cation-exchange resin.

17. The method of claim 1 , wherein the anion is boron tetrafluoride, phosphorus hexafluoride, methanesulfonate, trifluoromethanesulfonate, benzenesulfonate, p-toluenesulfonate, bis(methanesulfonyl)amide, bis(trifluoromethanesulfonyl)amide, bis(benzenesulfonyl)amide, or bis(p-toluenesulfonyl)amide.

18. The method of claim 1 , wherein the anion is bis(trifluoromethanesulfonyl)amide or (trifluoromethanesulfonyl)(trifluoroacetyl)amide.

19. The method of claim 5 , wherein the anion is bor

Assignees

• Massachusetts Inst Technology

Inventors

• Voskian Sahag
• De La Fuente Nunez Cesar
• Hatton T Alan
• Shaw Ryan Alex
• Brown Paul

Classifications

• B05D1/60 Primary

  Deposition of organic layers from vapour phase (vapour phase deposition in general C23C14/00, C23C16/00) · CPC title

• A01N59/20

  Copper · CPC title

• B05D5/00

  Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures · CPC title

• B01D2253/202

  Polymeric adsorbents · CPC title

• A01N59/06

  Aluminium; Calcium; Magnesium; Compounds thereof · CPC title