# US 2020/0399414 A1 · Self-Assembled Elastomers with Molecularly Encoded Tissue-Like Softness, Strain-Adaptive Stiffening and Coloration

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- Number: US 2020/0399414 A1
- Document ID: US20200399414A1
- Status: Published application
- Kind: A1
- Application number: 16/643,736
- Filed: 2018-09-03
- Published: 2020-12-24
- Earliest claimed: 2017-09-03
- Assignees: The University of North Carolina at Chapel Hill
- Applicants: The University of North Carolina At Chapel Hill
- Inventors: Sergei SHEIKO; Mohammad VATANKHAH-VARNOSFADERANI
- Web page: https://patentgrep.com/patent/US20200399414A1

## CPC

- C08F 293/005: {using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent}
- A61K 9/0021: {Intradermal administration, e.g. through microneedle arrays or needleless injectors}
- A61K 9/0024: {Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L)}
- A61L 15/24: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof {(A61L15/225 takes precedence)}
- A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 29/041: {obtained by reactions only involving carbon-to-carbon unsaturated bonds}
- C09D 153/00: Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09J 153/00: Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C08F 2438/01: Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED 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)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

The invention generally relates to linear-bottlebrush-linear copolymer blocks and methods of making and using same. The disclosed copolymer blocks can be useful in, for example, the formation of polymer networks that replicate biological stress-strain behavior. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

## Claims

### Claim 1

A copolymer block comprising a first linear polymer block, a brush-like polymer block, and a second linear polymer block, wherein the brush-like polymer block is positioned between the first and second linear polymer blocks.

### Claim 2 (depends on 1)

The copolymer block of claim 1, wherein each linear block is amorphous.

### Claim 3 (depends on 1)

The copolymer block of claim 1, wherein each linear block is either a methacrylate derivative, an acrylate derivative, a styrene derivative, or a norbornene derivative.

### Claim 4 (depends on 1)

The copolymer block of claim 1, wherein each linear block is independently selected from poly(methyl methacrylate), poly(benzyl methacrylate), polystyrene, poly(vinyl acetate), polycarbonate, and poly(oligo(ethylene glycol) monomethyl ether methacrylate.

### Claim 5 (depends on 1)

The copolymer block of claim 1, wherein the brush-like polymer block comprises the reaction product of:
a) a first monomer having a structure represented by a formula:
wherein R1 is a structure represented by a formula selected from:
wherein R10, when present, is selected from hydrogen and methyl;
wherein R2 is a first linear polymer residue; and
b) a diluent monomer.

### Claim 6 (depends on 5)

The copolymer block of claim 5, wherein the first linear polymer residue is a residue of a polymer selected from poly(butyl acrylate), poly(butyl methacrylate), poly(butyl norbornene), polystyrene, polydimethylsiloxane, and polyethylene glycol.

### Claim 7 (depends on 5)

The copolymer block of claim 5, wherein the second linear polymer residue is a residue of a polymer selected from polydimethylsiloxane, polycaprolactone, and poly(butyl acrylate).

### Claim 8 (depends on 5)

The copolymer block of claim 5, wherein the diluent monomer is selected from an alkyl acrylate monomer, a methacrylate monomer, and a norbornene monomer.

### Claim 9 (depends on 1)

The copolymer block of claim 1, wherein the brush-like polymer block comprises at least one residue having a structure represented by a formula selected from:
wherein r is an integer selected from 2 to 800;
wherein L is an active site of polymerization or a residue of a radical initiator;
wherein Q is an active site of polymerization or a residue of a radical initiator;
wherein each occurrence of R20 is independently selected from a first linear polymer residue and a diluent monomer residue,
provided that at least one occurrence of R20 is a first linear polymer residue and at least one occurrence of R20 is a diluent monomer residue; and
wherein each occurrence of R21, when present, is independently selected from hydrogen and methyl.

### Claim 10 (depends on 1)

The copolymer block of claim 1, wherein the brush-like polymer block is a polydimethylsiloxane derivative.

### Claim 11 (depends on 1)

The copolymer block of claim 1, wherein the copolymer block is a tri-block copolymer.

### Claim 12 (depends on 11)

The copolymer block of claim 11, wherein the tri-block copolymer is represented by a formula A-B-A′, wherein A is the first linear polymer block, B is the brush-like polymer block, and A′ is the second linear polymer block.

### Claim 13 (depends on 1)

A method of making the copolymer block of claim 1, the method comprising the step of synthesizing the copolymer block from a first residue of the first linear polymer block, a residue of the brush-like polymer block, and a second residue of the second linear polymer block, wherein synthesizing is via free radical polymerization (FRP), atom transfer radical polymerization (ATRP), SARA ATRP, anionic polymerization, or reversible addition-fragmentation chain-transfer polymerization (RAFT).

### Claim 14 (depends on 13)

The method of claim 13, wherein synthesizing is via ATRP.

### Claim 15 (depends on 13)

The method of claim 13, wherein the residue of the brush-like polymer block acts as a radical initiator.

### Claim 16 (depends on 1)

A polymer network comprising a plurality of the copolymer blocks of claim 1.

### Claim at position 17

17-27. (canceled)

### Claim 28 (depends on 16)

The polymer network of claim 16, wherein the polymer network has been formed as a medical device.

### Claim 29 (depends on 28)

The polymer network of claim 28, wherein the medical device is selected from an implant, a microneedle array, a wound dressing pad, a tissue adhesive, a tissue sealant, a dermal filler, a vascular graft, or a catheter.

### Claim 30

(canceled)

### Claim 31 (depends on 16)

The polymer network of claim 16, wherein the polymer network has been formed as a coating, a gasket, or an adhesive layer.

### Claim 32 (depends on 16)

An article comprising the polymer network of claim 16.

### Claim at position 23

33-47. (canceled)