# US 10,865,278 B2 · Vesicles formed from block copolymers, and novel block copolymers

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- Number: US 10,865,278 B2
- Document ID: US10865278B2
- Status: Granted
- Kind: B2
- Application number: 15/560,961
- Filed: 2016-03-24
- Published: 2018-03-22
- Granted: 2020-12-15
- Earliest claimed: 2015-03-24
- Assignees: Applied Biomimetic A/S; The Penn State Research Foundation
- Applicants: Applied Biomimetic A/S; The Penn State Research Foundation
- Inventors: Mariusz Piotr Grzelakowski; Manish Kumar; Ian T. Sines
- Web page: https://patentgrep.com/patent/US10865278B2

## CPC

- C08G 81/024: {Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G}
- A61K 8/14: Liposomes; Vesicles
- A61K 8/64: Proteins; Peptides; Derivatives or degradation products thereof
- A61K 8/90: Block copolymers (A61K8/89 takes precedence)
- A61K 9/1271: Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers (liposomes as conjugates {A61K47/6911})
- A61K 9/1277: Preparation processes; Proliposomes
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 47/42: Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein (oligopeptides having up to five amino acids {A61K47/183}; polyamino acids A61K47/34)
- B01D 69/125: {In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction}
- B01D 71/24: Rubbers
- B01D 71/56: Polyamides, e.g. polyester-amides
- B01D 71/80: Block polymers
- B01D 71/82: characterised by the presence of specified groups, e.g. introduced by chemical after-treatment
- C02F 1/44: by dialysis, osmosis or reverse osmosis {(general membrane separation processes B01D61/00, membrane modules B01D63/00, electrodialysis C02F1/4693, combination of membrane modules and bioreactors C02F3/1268)}
- C08G 73/0233: {Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups}
- C08L 87/005: {Block or graft polymers not provided for in groups C08L1/00 - C08L85/04}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Vesicles formed from a block copolymer comprising at least one (poly)2-C1-3alkyl-2-oxazoline block and at least one polybutadiene block; and membranes comprising such vesicles. Block copolymers comprising at least one (poly)2-C1-3alkyl-2-oxazoline block and at least one polybutadiene block, provided that the copolymer is not the diblock copolymer consisting of 40 butadiene units and 190 2-methyl-2-oxazoline units terminated by a hydroxy group, are novel, and also form part of the invention.

## Claims

### Claim 1

A block copolymer comprising at least one (poly)2-C1-3alkyl-2-oxazoline block and at least one polybutadiene block, which is a diblock copolymer AB, in which (poly)2-C1-3alkyl-2-oxazoline forms the A block and polybutadiene forms the B block, and which comprises an end group at the end of a (poly)2-C1-3alkyl-2-oxazoline block wherein the end group is selected from carboxy, activated carboxy, amine, methacrylate, thiol, azide, and alkyne and wherein the B block contains 5 to 15 butadiene units.

### Claim 2 (depends on 1)

A block copolymer as claimed in claim 1, in which the number of butadiene units in the B block is at least half the number of 2-C1-3alkyl-2-oxazoline units in the A block.

### Claim 3 (depends on 2)

A block copolymer as claimed in claim 2, in which the number of butadiene units in the B block is at least twice the number of 2-C1-3alkyl-2-oxazoline units in the A block.

### Claim 4 (depends on 1)

A block copolymer as claimed in claim 1, which contains from 5 to 180 2-C1-3alkyl-2-oxazoline units in the A block.

### Claim 5 (depends on 1)

A block copolymer as claimed in claim 1, in which said end group is selected from carboxy, activated carboxy, or an amine end group having the formula —NHR in which R represent an alkyl group having from one to 6 carbon atoms substituted by at least one —NH2 group.

### Claim 6 (depends on 1)

A block copolymer as claimed in claim 1, in which the (poly)2-C1-3alkyl-2-oxazoline is (poly)2-methyl-2-oxazoline.

### Claim 7 (depends on 1)

Vesicles formed from a block copolymer of claim 1.

### Claim 8 (depends on 7)

Vesicles as claimed in claim 7, in which C═C double bonds present in polybutadiene blocks of different block copolymer chains are cross-linked together.

### Claim 9 (depends on 7)

Vesicles as claimed in claim 7, having transmembrane proteins incorporated therein.

### Claim 10 (depends on 9)

Vesicles as claimed in claim 9, in which the transmembrane protein is an aquaporin.

### Claim 11 (depends on 7)

Vesicles as claimed in claim 7, containing a drug or a cosmetic agent.

### Claim 12 (depends on 9)

A filtration membrane comprising vesicles as claimed in claim 9.

### Claim 13 (depends on 12)

A filtration membrane as claimed in claim 12, which comprises a porous support and, covalently bonded to a surface thereof, a layer comprising a plurality of vesicles formed from the block copolymer, and having transmembrane proteins incorporated therein; and in which within said layer, vesicles are covalently linked together to form a coherent mass.

### Claim 14 (depends on 13)

A process for the preparation of a membrane as claimed in claim 13, which comprises providing an aqueous suspension of vesicles formed from the block copolymer, and having transmembrane proteins incorporated therein; depositing said suspension of vesicles on a surface of a porous support; and providing reaction conditions such that covalent bonds are formed between different vesicles and between vesicles and said surface.

### Claim 15 (depends on 14)

A process as claimed in claim 14, which comprises either:
(a) providing an aqueous suspension of vesicles formed from the block copolymer, and having transmembrane proteins incorporated therein, said vesicles being formed from block copolymers having reactive end groups X;
(b) providing a multifunctional linking agent having at least two reactive groups Y which are reactive with polymer end groups X;
(c) depositing said suspension of vesicles and said multifunctional linker on a support having a surface which is reactive with either polymer end groups X or reactive groups Y; and
(d) causing reaction of end groups X with groups Y, and either end groups X or groups Y with the surface of the support; or
(aa) providing a first aqueous suspension of vesicles formed from the block copolymer, and having transmembrane proteins incorporated therein, said vesicles being formed from block copolymers having reactive end groups X;
(bb) providing a second aqueous suspension of vesicles formed from the block copolymer, and having transmembrane proteins incorporated therein, said vesicles being formed from block copolymers having reactive end groups Y which are reactive with polymer end groups X;
(cc) depositing said suspensions of vesicles on a support having a surface which is reactive with either polymer end groups X or Y; and
(dd) causing reaction of end groups X with end groups Y, and either end groups X or end groups Y with the surface of the support.

### Claim 16 (depends on 15)

A process as claimed in claim 15, in which said multifunctional linking agent of step (b) is N-sulfosuccinimidyl-6-(4′-azido-2′-nitrophenylamino)hexanoate.

### Claim 17 (depends on 12)

A filtration membrane as claimed in claim 12, in which the transmembrane protein is an aquaporin.

### Claim 18 (depends on 13)

A membrane as claimed in claim 13, in which the transmembrane proteins are aquaporins.