# US 10,766,987 B2 · Crosslinked polyolefins for biomedical applications and method of making same

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- Number: US 10,766,987 B2
- Document ID: US10766987B2
- Status: Granted
- Kind: B2
- Application number: 15/861,608
- Filed: 2018-01-03
- Published: 2018-05-10
- Granted: 2020-09-08
- Earliest claimed: 2007-11-08
- Assignees: Innolene LLC
- Applicants: Innolene LLC
- Inventors: Yonghua Zhou; Leonard Pinchuk
- Web page: https://patentgrep.com/patent/US10766987B2

## CPC

- C08F 210/10: Isobutene
- A61F 2/1613: {having special lens configurations, e.g. multipart lenses; having particular optical properties, e.g. pseudo-accommodative lenses, lenses having aberration corrections, diffractive lenses, lenses for variably absorbing electromagnetic radiation, lenses having variable focus}
- A61L 27/16: obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08F 210/14: Monomers containing five or more carbon atoms
- C08F 212/08: Styrene
- C08F 212/12: Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
- C08F 212/32: containing two or more rings
- C08F 293/00: Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule (on to polymers modified by introduction of unsaturated end groups C08F290/02)
- C08F 297/00: Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08J 3/247: {Heating methods}
- G02B 1/043: {Contact lenses}
- A61F 2/1624: {having adjustable focus; power activated variable focus means, e.g. mechanically or electrically by the ciliary muscle or from the outside}
- A61F 2/1629: {for changing longitudinal position, i.e. along the visual axis when implanted}
- A61F 2002/1681: {having supporting structure for lens, e.g. haptics}
- C08F 212/06: Hydrocarbons
- C08J 2323/22: Copolymers of isobutene; butyl rubber
- C08J 2353/00: Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C)
- 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)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS

## Abstract

A method for preparing a copolymer that involves polymerizing at least one branched alkene monomer and at least one olefin monomer having a pendant benzocyclobutene (BCB) group to form a copolymer comprising a random distribution of a plurality of constitutional units corresponding to the at least one branched alkene monomer and the at least one olefin monomer. The polymerizing includes a carbocationic polymerization reaction involving sequential addition of a plurality of mixtures without terminating the carbocationic polymerization reaction, wherein the plurality of mixtures includes a mixture that includes the at least one branched alkene monomer and does not include the at least one olefin monomer having a pendant BCB group and a mixture that includes both the at least one branched alkene monomer and the at least one olefin monomer having a pendant BCB group. The copolymer composition can undergo crosslinking at elevated temperatures (preferably above 180° C.).

## Claims

### Claim 1

A method of preparing a copolymer comprising:
polymerizing at least one branched alkene monomer and at least one olefin monomer having a pendant benzocyclobutene (BCB) group to form a copolymer comprising a random distribution of a plurality of constitutional units that include constitutional units corresponding to the at least one branched alkene monomer and constitutional units corresponding to the at least one olefin monomer having a pendant BCB group;
wherein the polymerizing includes a carbocationic polymerization reaction involving i) forming a mixture that includes the at least one branched alkene monomer and at least one initiator compound to initiate a polymerization reaction of the at least one branched alkene monomer, wherein the mixture does not include the at least one olefin monomer having a pendant BCB group, and ii) adding both the at least one branched alkene monomer and the at least one olefin monomer having a pendant BCB group to the polymerization reaction of i) without terminating the carbocationic polymerization reaction.

### Claim 2 (depends on 1)

A method according to claim 1, wherein:
the first mixture further includes at least one solvent.

### Claim 3 (depends on 1)

A method according to claim 1, wherein:
the at least one branched alkene monomer comprises an isoolefin selected from the group consisting of isobutylene, 2-methyl-1-butene, 2-methyl-1-pentene, 2-methyl-1-hexene, and combinations thereof.

### Claim 4 (depends on 1)

A method according to claim 1, wherein:
the at least one branched alkene monomer comprises isobutylene.

### Claim 5 (depends on 1)

A method according to claim 1, wherein:
the at least one initiator compound of the mixture includes a Lewis acid coinitiator and an initiator selected from the group consisting of: a) organic ethers, b) organic esters, c) organic alcohols, d) organic halides, including tert-ester, tert-ether, tert-hydroxyl and tert-halogen containing compounds, e) alkyl cumyl ethers, cumyl halides, alkyl cumyl esters, cumyl hydroxyl compounds and hindered versions of the same, f) dicumyl chloride, g) 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene (HDCE), h) initiators having three or more initiation sites, and i) tricumyl chloride.

### Claim 6 (depends on 1)

A method according to claim 1, wherein:
the at least one initiator compound of the mixture includes a Lewis acid and 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene (HDCE).

### Claim 7 (depends on 1)

A method according to claim 1, wherein:
the at least one olefin monomer having a pendant BCB group comprises a monomer having the formula
wherein R is hydrogen or an alkyl group and n is 0.

### Claim 8 (depends on 7)

A method according to claim 7, wherein:
the at least one olefin monomer having a pendant BCB group comprises 4-vinylbenzocyclobutene or 2-(4-benzocyclobutenyl)-propene.

### Claim 9 (depends on 1)

A method according to claim 1, wherein:
the at least one olefin monomer having a pendant BCB group comprises a monomer having the formula
wherein R is alkyl group and n is an integer ranging from 0-3.

### Claim 10 (depends on 9)

A method according to claim 9, wherein:
the at least one olefin monomer having a pendant BCB group comprises 2-methyl-3-(4-benzocyclobutenyl)-propene.

### Claim 11 (depends on 1)

A method according to claim 1, wherein:
the copolymer further includes a glass-forming monomer selected from the group consisting of styrene, indene, α-methylstyrene, p-tert-butylstyrene, p-chlorostyrene, norbornene, and combinations thereof.

### Claim 12 (depends on 11)

A method according to claim 11, wherein:
the glass-forming monomer is styrene.

### Claim 13 (depends on 1)

A method according to claim 1, wherein:
the at least one olefin monomer having a pendant BCB group is present in amount ranging from 0.01 to 60 mol % of the monomeric units of the copolymer.

### Claim 14 (depends on 1)

A method according to claim 1, wherein:
the carbocationic polymerization reaction is a living cationic polymerization reaction.

### Claim 15 (depends on 1)

A method according to claim 1, wherein:
the copolymer undergoes crosslinking when exposed to temperatures of at least 180° C.

### Claim 16 (depends on 1)

A method of preparing a thermoset polymer comprising:
processing a copolymer prepared according to claim 1 to form a resultant thermoset polymer, wherein the processing includes heating the copolymer such that the copolymer undergoes crosslinking to form the resultant thermoset polymer.

### Claim 17 (depends on 1)

A method of preparing an implantable medical device comprising:
processing a copolymer prepared according to claim 1 to form at least part of the implantable medical device, wherein the processing includes heating the copolymer such that the copolymer undergoes crosslinking to form a resultant thermoset polymer that is part of the implantable medical device.

### Claim 18 (depends on 17)

A method according to claim 17, wherein:
the implantable medical device comprises an intraocular lens.