Hydrogel

Patent metadata

Field	Value
Publication number	US-2022185927-A1
Application number	US-202017600072-A
Country	US
Kind code	A1
Filing date	Dec 1, 2020
Priority date	Jan 24, 2019
Publication date	Jun 16, 2022
Grant date	—

Abstract

A hydrogel includes a dendritic core with 2 to 30 arms, and first and second acrylamide monomers incorporated into each arm. The first acrylamide monomer is: (I), wherein R1 and R2 are independently selected from an alkyl, an alkylamino, an alkylamido, an alkylthio, an aryl, a glycol, and optionally substituted variants thereof; and the second acrylamide monomer is: (II), wherein R3 and R4 are independently hydrogen or an alkyl; L is a linker including a linear chain of 2 to 20 atoms selected from carbon, oxygen, and nitrogen and optional substituents on the carbon and any nitrogen atoms; A is an N substituted amide: (III), where R5 is hydrogen or an alkyl; E is a linear chain of 1 to 4 atom(s) selected from carbon, oxygen and nitrogen, and optional substituents on the carbon and any nitrogen atoms; and Z is an optional nitrogen containing heterocycle.

First claim

1 . A hydrogel, comprising:
a dendritic core having from 2 arms to 30 arms; a first acrylamide monomer incorporated into each arm of the dendritic core, the first acrylamide monomer having a structure:

wherein R 1 and R 2 are independently selected from the group consisting of an alkyl, an alkylamino, an alkylamido, an alkylthio, an aryl, a glycol, and optionally substituted variants thereof, and
a second acrylamide monomer incorporated into each arm of the dendritic core, the second acrylamide monomer having a structure:

wherein R 3 is hydrogen or an alkyl; R 4 is hydrogen or an alkyl; L is a linker including a linear chain of 2 atoms to 20 atoms wherein each atom is independently selected from the group consisting of carbon, oxygen, and nitrogen and optional substituents on any carbon and any nitrogen atoms in the chain; A is an N substituted amide having a structure

where R 5 is hydrogen or an alkyl; E is a linear chain of 1 atom to 4 atoms wherein each atom is independently selected from the group consisting of carbon, oxygen and nitrogen, and optional substituents on any carbon and any nitrogen atoms in the chain; and Z is an optional nitrogen containing heterocycle.

2 . The hydrogel as defined in claim 1 , wherein the first acrylamide monomer is N,N-dimethylacrylamide.

3 . The hydrogel as defined in claim 1 or 2 , wherein the dendritic core contains a thiocarbonylthio group in each arm.

4 . The hydrogel as defined in claim 3 , wherein the thiocarbonylthio group is selected from the group consisting of a dithiobenzoate, a trithiocarbonate, and a dithiocarbamate.

5 . The hydrogel as defined in claim 3 , wherein the dendritic core is selected from the group consisting of 3,5-Bis(2-dodecylthiocarbonothioylthio-1-oxopropoxy)benzoic acid, 1,1,1-Tris[(dodecylthiocarbonothioylthio)-2-methylpropionate]ethane, and Pentaerythritol tetrakis[2-(dodecylthiocarbonothioylthio)-2-methylpropionate].

6 . The hydrogel as defined in any of the preceding claims, wherein the dendritic core includes an atom transfer radical polymerization initiator in each arm.

7 . The hydrogel as defined in claim 6 , wherein the dendritic core is selected from the group consisting of Bis[2-(2′-bromoisobutyryloxy)ethyl]disulfide, 2-Bromoisobutyric anhydride, Ethylene bis(2-bromoisobutyrate), Pentaerythritol tetrakis(2-bromoisobutyrate), Dipentaerythritol hexakis(2-bromoisobutyrate), and 1,1,1-Tris(2-bromoisobutyryloxymethyl)ethane.

8 . The hydrogel as defined in any of the preceding claims wherein the dendritic core includes:
a multi-functional central molecule; and a plurality of atom transfer radical polymerization mono-initiators attached to the multi-functional central molecule.

9 . The hydrogel as defined in claim 8 , wherein the atom transfer radical polymerization mono-initiator is selected from the group consisting of 2-azidoethyl 2-bromoisobutyrate, poly(ethylene glycol) methyl ether 2-bromoisobutyrate, 2-(2-Bromoisobutyryloxy)ethyl methacrylate, Dodecyl 2-bromoisobutyrate, 2-Hydroxyethyl 2-bromoisobutyrate, 1-(Phthalimidomethyl) 2-bromoisobutyrate, and Propargyl 2-bromoisobutyrate.

10 . The hydrogel as defined in any of the preceding claims wherein the dendritic core includes a nitroxide mediated polymerization initiator in each arm.

11 . The hydrogel as defined in claim 10 , wherein the dendritic core is selected from the group consisting of 1,3,5-tris((4-(1-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethyl)benzyl)oxy)benzene and 1,3,5-tris((3,5-bis((4-(1-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)ethyl)benzyl)oxy)benzyl)oxy)benzene.

12 . The hydrogel as defined in any of the preceding claims wherein the dendritic core includes:
a multi-functional central molecule; and a plurality of nitroxide mediated polymerization mono-initiators attached to the multi-functional central molecule.

13 . The hydrogel as defined in claim 12 , wherein each of the plurality of nitroxide mediated polymerization mono-initiators has a structure selected from the group consisting of:

and wherein I is selected from the group consisting of

14 . The hydrogel as defined in any of the preceding claims, wherein the first acrylamide monomer and the second acrylamide monomer form a block copolymer, a random copolymer, a statistical copolymer, or an alternating copolymer in each arm of the dendritic core.

15 . The hydrogel as defined in any of the preceding claims wherein second acrylamide monomer is azido acetamido pentyl acrylamide.

16 . A flow cell, comprising:
a substrate; and a hydrogel according to any of the preceding claims on the substrate.

17 . The flow cell as defined in claim 16 , wherein the substrate includes a plurality of depressions separated by interstitial regions, and wherein the hydrogel is positioned within each of the depressions.

18 . The flow cell as defined in claim 16 or 17 , further comprising amplification primers grafted to polymeric hydrogel.

19 . The flow cell as defined in any of the claims 16 - 18 wherein the substrate includes a channel, and wherein the hydrogel is positioned in the channel.

20 . The flow cell as defined in any of the claims 16 - 19 wherein:
the first acrylamide monomer and the second acrylamide monomer form a random copolymer in each arm of the dendritic core; or
the first acrylamide monomer and the second acrylamide monomer form a statistical copolymer in each arm of the dendritic core; or
the first acrylamide monomer and the second acrylamide monomer form an alternating copolymer in each arm of the dendritic core; or
the first acrylamide monomer and the second acrylamide monomer form a block copolymer in each arm of the dendritic core.

21 . A method, comprising:
incorporating a copolymer into each arm of a multi-arm dendritic core component having from 2 arms to 30 arms, wherein the copolymer includes a first acrylamide monomer and a second acrylamide monomer, and wherein: the first acrylamide monomer has a structure:

wherein R 1 and R 2 are independently selected from the group consisting of an alkyl, an alkylamino, an alkylamido, an alkylthio, an aryl, a glycol, and optionally substituted variants thereof; and
the second acrylamide monomer has a structure:

wherein R 3 is hydrogen or an alkyl; R 4 is hydrogen or an alkyl; L is a linker including a linear chain of 2 atoms to 20 atoms wherein each atom is independently selected from the group consisting of carbon, oxygen, and nitrogen and optional substituents on any carbon and any nitrogen atoms in the chain; A is an N substituted amide having a structure

where R 5 is hydrogen or an alkyl; E is a linear chain of 1 atom to 4 atoms wherei

Assignees

• Illumina Cambridge Ltd

Inventors

• Artioli Gianluca Andrea
• Brown Andrew A
• George Wayne N
• Pilkington Colin
• Pitcairn Jem
• Richez Alexandre
• Von Hatten Xavier

Classifications

• C08F265/06 Primary

  Polymerisation of acrylate or methacrylate esters on to polymers thereof · CPC title

• C08F220/54

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• C08F220/603 Primary

  and containing oxygen in addition to the carbonamido oxygen and nitrogen · CPC title

• C08F2/38

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C09D133/24

  Homopolymers or copolymers of amides or imides · CPC title