US2004106741A1PendingUtilityA1

Nanofilm compositions with polymeric components

Priority: Sep 17, 2002Filed: Apr 29, 2003Published: Jun 3, 2004

Est. expirySep 17, 2022(expired)· nominal 20-yr term from priority

Inventors:Joshua W. Kriesel Donald B. Bivin David Olson Jeremy J. Harris

C08F 8/30C08F 2/00B82B 3/00

PatentIndex Score

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References

Claims

Abstract

Nanofilms useful for filtration are prepared from amphiphilic species and one or more polymeric components. The amphiphilic species or components may be oriented on an interface or surface. A nanofilm may be prepared by coupling one or more of the components. The nanofilm may also be deposited or attached to a substrate.

Claims

exact text as granted — not AI-modified

What is claimed is:

1 . A nanofilm composition comprising a reaction product of macrocyclic modules and at least one polymeric component.

2 . The nanofilm composition of claim 1 , wherein the macrocyclic modules are coupled to each other.

3 . The nanofilm composition of claim 2 , wherein the macrocyclic modules are coupled to each other through linker molecules.

4 . The nanofilm composition of claim 3 , wherein the linker molecules are selected from the group consisting of

and mixtures therefor; wherein m is 1-10, n is 1-6, R is —H or —CH 3 , R′ is —(CH 2 ) n — or phenyl, R″ is —(CH 2 ) n —, polyenthylene glycol (PEG), or polypropylene glycol (PPG), and X is Br, Cl, I, or other leaving group.

5 . The nanofilm composition of claim 1 , wherein the macrocyclic modules are coupled to the at least one polymeric component.

6 . The nanofilm composition of claim 5 , wherein the macrocyclic modules are coupled to the at least one polymeric component through linker molecules.

7 . The nanofilm composition of claim 6 , wherein the linker molecules are selected from the group consisting of

and mixtures thereof; wherein m is 1-10, n is 1-6, R is —H or —CH 3 , R′ is —(CH 2 ) n — or phenyl, R″ is —(CH 2 ) n —, polyethylene glycol (PEG), or polypropylene glycol (PPG), and X is Br, Cl, I, or other leaving group.

8 . The nanofilm composition of claim 1 , wherein the macrocyclic modules are selected from the group consisting of Hexamer 1a, Hexamer 1dh, Hexamer 3j-amine, Hexamer 1jh, Hexamer 1jh-AC, Hexamer 2j-amine/ester, Hexamer 1dh-acryl, Octamer 5jh-aspartic, Octamer 4jh-acryl, and mixtures thereof.

9 . The nanofilm composition of claim 8 , wherein the macrocyclic modules are Hexamer 1dh.

10 . The nanofilm composition of claim 1 , wherein the polymeric component is selected from the group consisting of poly(maleic anhydride)s, poly(ethylene-co-maleic anhydride)s, poly(maleic anhydride-co-alpha olefin)s, polyacrylates, polymethylmethacrylate, polymers containing at least one oxacyclopropane group, polyethyleneimides, polyetherimides, polyethylene oxides, polypropylene oxides, polyurethanes, polystyrenes, poly(vinyl acetate)s, polytetrafluoroethylenes, polyethylenes,kpolypropylenes, ethylene-propylene copolymers, polyisoprenes, polyneopropenes, polyamides, polyimides, polysulfones, polyethersulfones, polyethylene terephthalates, polybutylene terephthalates, polysulfonamides, polysulfoxides, polyglycolic acids, polyacrylamides, polyvinylalcohols, polyesters, polyester ionomers, polycarbonates, polyvinylchlorides, polyvinylidene chlorides, polyvinylidene fluorides, polyvinylpyrrolidones, polylactic acids, polypeptides, polysorbates, polylysines, hydrogels, carbohydrates, polysaccharides, agaroses, amyloses, amylopectins, glycogens, dextrans, celluloses, cellulose acetates, chitins, chitosans, peptidoglycans, glycosaminoglycans, polynucleotides, poly(T), poly(A), nucleic acids, proteoglycans, glycoproteins, glycolipids, and mixtures thereof.

11 . The nanofilm composition of claim 1 , wherein the polymeric component is poly(maleic anhydride-co-alpha olefin).

12 . The nanofilm composition of claim 1 , wherein the polymeric component comprises a polymerizable monomer.

13 . The nanofilm composition of claim 12 , wherein the polymerizable monomer comprises CH 2 ═CHC(O)OCH 2 CH 2 OH.

14 . The nanofilm composition of claim 1 , wherein the polymeric component comprises a polymerizable amphiphile.

15 . The nanofilm composition of claim 13 , wherein the polymerizable amphiphile is selected from the group consisting of amphiphilic acrylates, amphiphilic acrylamides, amphiphilic vinyl esters, amphiphilic anilines, amphiphilic diynes, amphiphilic dienes, amphiphilic acrylic acids, amphiphilic enes, amphiphilic cinnamic acids, amphiphilic amino-esters, amphiphilic oxiranes, amphiphilic amines, amphiphilic diesters, amphiphilic diacids, amphiphilic diols, amphiphilic polyols, and amphiphilic diepoxides.

16 . The nanofilm of claim 1 , further comprising a non-polymerizable amphiphile.

17 . The nanofilm of claim 16 , wherein the non-polymerizable amphiphile is selected from the group consisting of decylamine and stearic acid.

18 . The nanofilm composition of claim 1 prepared by spin coating, spray coating, dip coating, grafting, casting, phase inversion, electroplating, or knife-edge coating.

19 . The nanofilm composition of claim 1 , wherein the area fraction of the polymeric components is from 0.5 to 98 percent.

20 . The nanofilm composition of claim 1 , wherein the area fraction of the polymeric components is less than about 20 percent.

21 . The nanofilm composition of claim 1 , wherein the area fraction of the polymeric components is less than about 5 percent.

22 . The nanofilm composition of claim 1 , wherein the thickness of the nanofilm composition is less than about 30 nanometers.

23 . The nanofilm composition of claim 1 , wherein the thickness of the nanofilm composition is less than about 6 nanometers.

24 . The nanofilm composition of claim 1 , wherein the thickness of the nanofilm composition is less than about 2 nanometers.

25 . The nanofilm composition of claim 1 , wherein the surface loss modulus of the nanofilm composition at a surface pressure from 5-30 mN/m is less than about 50% of the surface loss modulus of the same nanofilm composition made without the polymeric components.

26 . The nanofilm composition of claim 1 , wherein the surface loss modulus of the nanofilm composition at a surface pressure from 5-30 mN/m is less than about 30% of the surface loss modulus of the same nanofilm composition made without the polymeric components.

27 . The nanofilm composition of claim 1 , wherein the surface loss modulus of the nanofilm composition at a surface pressure from 5-30 mN/m is less than about 20% of the surface loss modulus of the same nanofilm composition made without the polymeric components.

28 . The nanofilm composition of claim 1 , having the following filtration function:

MOLECULAR

SOLUTE
WEIGHT
PASS/NO PASS

Albumin
68
kDa
NP

Ovalbumin
44
kDa
P

Myoglobin
17
kDa
P

β 2 -Microglobulin
12
kDa
P

Insulin
5.2
kDa
P

Vitamin B 12
1350
Da
P

Urea, H 2 O, ions
&lt;1000
Da
P

29 . The nanofilm composition of claim 1 , having the following filtration function:

MOLECULAR

SOLUTE
WEIGHT
PASS/NO PASS

β 2 -Microglobulin
12
kDa
NP

Insulin
5.2
kDa
NP

Vitamin B 12
1350
Da
NP

Glucose
180
Da
NP

Creatinine
131
Da
NP

H 2 PO 4 − , HPO 4 2−
≈97
Da
NP

HCO 3 −
61
Da
NP

Urea
60
Da
NP

K+
39
Da
P

Na+
23
Da
P

30 . The nanofilm composition of claim 1 , wherein the nanofilm is impermeable to viruses and larger species.

31 . The nanofilm composition of claim 1 , wherein the nanofilm is impermeable to immunoglobulin G and larger species.

32 . The nanofilm composition of claim 1 , wherein the nanofilm is impermeable to albumin and larger species.

33 . The nanofilm composition of claim 1 , wherein the nanofilm is impermeable to β 2 -Microglobulin and larger species.

34 . The nanofilm composition of claim 1 , wherein the nanofilm is permeable only to water and smaller species.

35 . The nanofilm composition of claim 1 , having a molecular weight cut-off of 13 kDa.

36 . The nanofilm composition of claim 1 , having a molecular weight cut-off of 190 Da.

37 . The nanofilm composition of claim 1 , having a molecular weight cut-off of 100 Da.

38 . The nanofilm composition of claim 1 , having a molecular weight cut-off of 45 Da.

39 . The nanofilm composition of claim 1 , having a molecular weight cut-off of 20 Da.

40 . The nanofilm composition of claim 1 , having high permeability for water molecules and Na + , K + , and Cs + in water.

41 . The nanofilm composition of claim 36 , having low permeability for glucose and urea.

42 . The nanofilm composition of claim 1 , having high permeability for water molecules and Cl − in water.

43 . The nanofilm composition of claim 1 , having high permeability for water molecules and K + in water, and low permeability for Na + in water.

44 . The nanofilm composition of claim 1 , having high permeability for water molecules and Na + in water, and low permeability for K + in water.

45 . The nanofilm composition of claim 1 , having low permeability for urea, creatinine, Li + , Ca 2 + , and Mg 2 + in water.

46 . The nanofilm composition of claim 41 , having high permeability for Na + , K + , hydrogen phosphate, and dihydrogen phosphate in water.

47 . The nanofilm composition of claim 41 , having high permeability for Na + , K + , and glucose in water.

48 . The nanofilm composition of claim 1 , having low permeability for myoglobin, ovalbumin, and albumin in water.

49 . The nanofilm composition of claim 1 , having high permeability for organic compounds and low permeability for water.

50 . The nanofilm composition of claim 1 , having low permeability for organic compounds and high permeability for water.

51 . The nanofilm composition of claim 1 , having low permeability for water molecules and high permeability for helium and hydrogen gases.

52 . A nanofilm composition comprising at least two layers of the nanofilm of claim 1 .

53 . The nanofilm composition of claim 52 , fuirther comprising at least one spacing layer between any two of the nanofilm layers.

54 . The nanofilm composition of claim 53 , wherein the spacing layer comprises a layer of a polymer, a gel, or inorganic particles.

55 . The nanofilm composition of claim 1 , deposited on a substrate.

56 . The nanofilm composition of claim 55 , wherein the nanofilm is coupled to the substrate through the polymeric component.

57 . The nanofilm composition of claim 55 , wherein the substrate is porous.

58 . The nanofilm composition of claim 55 , wherein the substrate is non-porous.

59 . The nanofilm composition of claim 55 , wherein the nanofilm is coupled to the substrate through biotin-strepavidin mediated interaction.

60 . A nanofilm composition comprising a reaction product of a polymeric component and an amphiphile.

61 . The nanofilm of claim 60 , wherein the amphiphile is a polymerizable amphiphile.

62 . The nanofilm composition of claim 61 , wherein the polymerizable amphiphile is selected from the group consisting of amphiphilic acrylates, amphiphilic acrylamides, amphiphilic vinyl esters, amphiphilic anilines, amphiphilic diynes, amphiphilic dienes, amphiphilic acrylic acids, amphiphilic enes, amphiphilic cinnamic acids, amphiphilic amino-esters, amphiphilic oxiranes, amphiphilic amines, amphiphilic diesters, amphiphilic diacids, amphiphilic diols, amphiphilic polyols, and amphiphilic diepoxides.

63 . The nanofilm of claim 60 , wherein the amphiphile is non-polymerizable.

64 . The nanofilm of claim 63 , wherein the non-polymerizable amphiphile is selected from the group consisting of decylamine and stearic acid.

65 . The nanofilm composition of claim 60 , wherein the polymeric component is selected from the group consisting of poly(maleic anhydride)s, poly(ethylene-co-maleic anhydride)s, poly(maleic anhydride-co-alpha olefin)s, polyacrylates, polymethylmethacrylate, polymers containing at least one oxacyclopropane group, polyethyleneimides, polyetherimides, polyethylene oxides, polypropylene oxides, polyurethanes, polystyrenes, poly(vinyl acetate)s, polytetrafluoroethylenes, polyethylenes, polypropylenes, ethylene-propylene copolymers, polyisoprenes, polyneopropenes, polyamides, polyimides, polysulfones, polyethersulfones, polyethylene terephthalates, polybutylene terephthalates, polysulfonamides, polysulfoxides, polyglycolic acids, polyacrylamides, polyvinylalcohols, polyesters, polyester ionomers, polycarbonates, polyvinylchlorides, polyvinylidene chlorides, polyvinylidene fluorides, polyvinylpyrrolidones, polylactic acids, polypeptides, polysorbates, polylysines, hydrogels, carbohydrates, polysaccharides, agaroses, amyloses, amylopectins, glycogens, dextrans, celluloses, cellulose acetates, chitins, chitosans, peptidoglycans, glycosaminoglycans, polynucleotides, poly(T), poly(A), nucleic acids, proteoglycans, glycoproteins, glycolipids, and mixtures thereof.

66 . The nanofilm of claim 60 , wherein the polymeric component is amphiphilic.

67 . The nanofilm of claim 60 , wherein the polymeric component comprises a polymerizable monomer.

68 . The nanofilm of claim 60 , wherein the polymeric component comprises a polymerizable amphiphile.

69 . The nanofilm composition of claim 61 , wherein the nanofilm is prepared by a process comprising polymerizing the polymerizable amphiphiles at an air-water interface.

70 . The nanofilm composition of claim 60 , wherein the nanofilm is prepared by a process comprising polymerizing the polymeric component at an air-water interface.

71 . The nanofilm of claim 63 , wherein the polymeric component is a polymer, and wherein the non-polymerizable amphiphiles are coupled to the polymer.

72 . A nanofilm composition comprising a reaction product of a polymeric component, wherein the polymeric components are linked by linker molecules.

73 . The nanofilm composition of claim 72 , wherein the polymeric component is selected from the group consisting of poly(maleic anhydride)s, poly(ethylene-co-maleic anhydride)s, poly(maleic anhydride-co-alpha olefin)s, polyacrylates, polymethylmethacrylate, polymers containing at least one oxacyclopropane group, polyethyleneimides, polyetherimides, polyethylene oxides, polypropylene oxides, polyurethanes, polystyrenes, poly(vinyl acetate)s, polytetrafluoroethylenes, polyethylenes, polypropylenes, ethylene-propylene copolymers, polyisoprenes, polyneopropenes, polyarnides, polyimides, polysulfones, polyethersulfones, polyethylene terephthalates, polybutylene terephthalates, polysulfonamides, polysulfoxides, polyglycolic acids, polyacrylamides, polyvinylalcohols, polyesters, polyester ionomers, polycarbonates, polyvinylchlorides, polyvinylidene chlorides, polyvinylidene fluorides, polyvinylpyrrolidones, polylactic acids, polypeptides, polysorbates, polylysines, hydrogels, carbohydrates, polysaccharides, agaroses, amyloses, amylopectins, glycogens, dextrans, celluloses, cellulose acetates, chitins, chitosans, peptidoglycans, glycosaminoglycans, polynucleotides, poly(T), poly(A), nucleic acids, proteoglycans, glycoproteins, glycolipids, and mixtures thereof.

74 . A nanofilm composition comprising a reaction product of at least two polymeric components, wherein the first polymeric component is a polymerizable amphiphile, and the second polymeric component is a polymerizable monomer.

75 . A composition comprising a mixture of macrocyclic modules and at least one polymeric component in organic solvent.

76 . A composition comprising a thin film of a reaction product of macrocyclic modules and at least one polymeric component, wherein the composition is prepared by a process comprising contacting the macrocyclic modules and the at least one polymeric component at an air-liquid or liquid-liquid interface.

77 . A method for making a nanofilm composition comprising: (a) providing a mixture of macrocyclic modules and at least one polymeric component; and (b) forming the mixture into a thin film at an air-liquid or liquid-liquid interface.

78 . The method of claim 77 , wherein the polymeric component is polymerizable, further comprising polymerizing the polymeric component at the air-liquid or liquid-liquid interface.

79 . A method for making a nanofilm composition comprising the reaction product of macrocyclic modules and at least one polymeric component, comprising: (a) providing a subphase containing the at least one polymeric component; and (b) contacting macrocyclic modules with the surface of the subphase.

80 . The method of claim 79 , further comprising: (c) contacting a linker molecule with the surface of the subphase.

81 . A method for making a nanofilm composition comprising the reaction product of macrocyclic modules and at least one polymeric component, comprising: (a) providing a first liquid phase comprising the macrocyclic modules; (b) providing a second liquid phase comprising the at least one polymeric component; and (c) forming a liquid-liquid interface from the first liquid phase and the second liquid phase.

82 . A method for filtration comprising using the nanofilm composition of claim 1 to separate a component from a fluid.

83 . A method for filtration comprising using the nanofilm composition of claim 1 to separate a component from a mixture of at least two gases.

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