# US 11,897,983 B2 · Hydrolysis-tolerant crosslinked polymers from reverse-acrylate multifunctional monomers

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- Number: US 11,897,983 B2
- Document ID: US11897983B2
- Status: Granted
- Kind: B2
- Application number: 17/203,648
- Filed: 2021-03-16
- Published: 2021-10-07
- Granted: 2024-02-13
- Earliest claimed: 2020-03-26
- Assignees: TDA Research, Inc.
- Applicants: TDA Research, Inc
- Inventors: Robert Donald Bolskar; James William Raebiger; Rhia M Martin; Silvia De Vito Luebben
- Web page: https://patentgrep.com/patent/US11897983B2

## CPC

- C07C 69/734: Ethers
- C08F 222/1025: {of aromatic dialcohols}
- C07C 69/618: having unsaturation outside the six-membered aromatic ring
- C08F 2/48: by ultraviolet or visible light
- C08F 2/50: with sensitising agents
- C08F 2438/00: Living radical polymerisation
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

Crosslink-forming monomers, comprising reverse-acrylate groups, and crosslinked polymer networks formed by the polymerization of monomers that comprise said reverse-acrylate crosslink-forming monomers. Crosslink-forming monomers, comprising reverse-acrylate groups, comprising an alkyl, an aryl, an alkoxyl, and an alkylamino group bridging one or more reverse-acrylate groups. Crosslink-forming monomers, comprising reverse-acrylate groups, comprising an alkyl, an aryl, an alkoxyl, and an alkylamino ester groups. Crosslink-forming monomers, comprising reverse-acrylate groups, comprising alkyl groups where the group is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl. Reverse-acrylate crosslink-forming monomers comprise a chemical structure where the two or more polymerizable carbon-carbon double bonds are connected by a crosslinking group on the opposite side of the hydrolysable ester groups relative to normal crosslinking acrylate monomers. The crosslink-forming monomers herein form crosslinked polymer networks that do not lose their crosslinking upon hydrolysis of the ester linkages.

## Claims

### Claim 1

A crosslink-forming monomer, comprising the chemical structure:
wherein, R1 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; wherein, R2 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; and R3 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino.

### Claim 2 (depends on 1)

The crosslink-forming monomer of claim 1, wherein R2 is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl; and wherein, R3 is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl.

### Claim 3 (depends on 2)

The crosslink-forming monomer of claim 2, wherein R2 and R3 are each an ethyl group, the crosslink-forming monomer comprising the chemical structure:
wherein, R1 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino.

### Claim 4 (depends on 3)

The crosslink-forming monomer of claim 3, further comprising the chemical structure:

### Claim 5 (depends on 3)

The crosslink-forming monomer of claim 3, further comprising the chemical structure:

### Claim 6 (depends on 1)

A crosslinked polymer network comprising crosslinks formed from the polymerization of the crosslink-forming monomer of claim 1, wherein the crosslinked polymer network comprises a plurality of crosslink group having the chemical structure:
wherein, R1 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; wherein, R2 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; and R3 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino.

### Claim 7 (depends on 6)

The crosslinked polymer network of claim 6, wherein the crosslinked polymer network comprises a plurality of crosslink group having the chemical structure:
wherein, R1 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino.

### Claim 8 (depends on 7)

The crosslinked polymer network of claim 7, wherein the crosslinked polymer network comprises a plurality of crosslink group having the chemical structure:

### Claim 9 (depends on 7)

The crosslinked polymer network of claim 7, wherein the crosslinked polymer network comprises a plurality of crosslink group having the chemical structure:

### Claim 10 (depends on 1)

The crosslink-forming monomer of claim 1, further comprising the chemical structure:
wherein, R1 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; wherein, R2 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; R3 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino; and R4 is selected from the group consisting of an alkyl, an aryl, an alkoxyl, and an alkylamino.

### Claim 11 (depends on 10)

The crosslink-forming monomer of claim 10, wherein R2 is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl; wherein, R3 is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl; and wherein, R4 is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl.