Synthesis of highly branched polymers via high throughput screening

Patent metadata

Field	Value
Publication number	US-2025236694-A1
Application number	US-202519032863-A
Country	US
Kind code	A1
Filing date	Jan 21, 2025
Priority date	Jan 19, 2024
Publication date	Jul 24, 2025
Grant date	—

Abstract

Efficient condition optimization for the synthesis of highly branched polymers using high throughput screening has been developed. This innovation allows rapid production of soluble, highly branched polymers with different properties (molecular weight, degree of branching, etc.). Moreover, this versatile technique has the potential to be extended to other monomer/linker systems and polymerization techniques such as emulsion or suspension polymerization, anionic polymerization and continuous flow synthesis. A resin composition is further disclosed.

First claim

What is claimed is:

1 . A resin composition, comprising:
70.0 mol % or more of monofunctional (meth)acrylic acid alkyl esters; 20.0 mol % or less of multifunctional (meth)acrylic acid alkyl esters or a multifunctional vinyl compound, 0 or 0.01 mol % to 5 mol % or 10 mol % of (meth)acrylic acid, wherein: a glass transition temperature of said resin composition is from −80° C. to 80° C., the resin composition is characterized by uniform dissolution of said resin composition in an organic solvent to form a solution comprising 1% to 80% by weight of the resin composition.

2 . The resin composition of claim 1 wherein:
one or more of the monofunctional (meth)acrylic acid alkyl esters comprise alkyl, alkynyl or aryl groups of one or more carbon atoms, and/or
one or more of the multifunctional (meth)acrylic acid alkyl esters comprise alkylene, alkynylene or arylene groups of 18 carbon atoms or less.

3 . The resin composition of claim 1 , further comprising 99.9 mol % or more of the monofunctional (meth)acrylic acid alkyl esters and 0.01 mol % or less of the multifunctional (meth)acrylic acid alkyl esters.

4 . The resin composition of claim 1 , wherein one or more of the monofunctional (meth)acrylic acid alkyl esters comprise 1≤number of carbon atoms ≤18 and one or more the multifunctional (meth)acrylic acid alkyl esters comprise 1≤number of carbon atoms ≤18.

5 . The resin composition of claim 1 , wherein the monofunctional and/or multifunctional (meth)acrylate acid alkyl esters comprise 2 or more carbons in the alkyl groups.

6 . The resin composition of claim 1 , wherein the multifunctional (meth)acrylate acid alkyl esters comprise asymmetric multifunctional (meth)acrylate acid alkyl esters.

7 . The resin composition of claim 1 , wherein the dissolution of the resin composition in the organic solvent forms composition polymers having a molecular weight larger than 70 kDa.

8 . The resin composition of claim 1 , wherein less than 50% of the solvent by volume is used in the polymerization of the resin composition in the solvent.

9 . The resin composition of claim 1 , further comprising 0.1 mol % to 10 mol % of (meth)acrylic acid.

10 . The resin composition of claim 1 , wherein a weight average molecular weight Mw of the resin composition by Gel Permeation Chromatography (GPC) measurement as polystyrene equivalent is between 0.5 kDa and 1000.0 kDa, and the polydispersity (PDI) is between 1.00 and 120.

11 . The resin composition according to claim 1 , wherein the multifunctional (meth)acrylic acid alkyl ester is either ethylene glycol di(meth)acrylate or 2-(acryloyloxy)ethyl methacrylate (AEMA).

12 . The resin composition of claim 1 , wherein the solution comprises a liquid and/or the solution of the resin composition shows or is characterized by flowability when the displacement of the sample solution is not zero when 1 g of the sample solution is taken in a vial and the vial is placed upside down and allowed to stand for 1 hour.

13 . An adhesive comprising the resin composition according to claim 1 .

14 . The adhesive of claim 14 that exhibits adhesive strength between 0.1 N/25 mm and 50 N/25 mm in a 180° peel test.

15 . The resin composition of claim 1 , of the structure:

wherein
70.0 mol %≤x≤99.9 mol %,
0.01 mol %≤y≤20 mol %,
z≤10 mol %,
R 1 , R 3 , R 5 , and R 6 are each independently a hydrogen atom or a methyl group,
R 2 is an alkyl, alkenyl, or aryl group having 1 to 18 carbon atoms, and
R 4 is a group having 1 to 18 carbon atoms or having 1 to 6 (meth)acryloyl groups.

16 . The resin composition of claim 15 , wherein the monofunctional (meth)acrylic acid alkyl ester units are each of n-butyl acrylate (nBA) and the multifunctional (meth)acrylic acid alkyl ester units are each of ethylene glycol diacrylate, ethylene glycol dimethacrylate, 2-acryloyloxyethyl methacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate or dipentaerythritol pentaacrylate.

17 . The resin composition of claim 1 further comprising the solution comprising the resin composition and a metal salt, wherein the metal salt comprises 0.05% to 5% or 10% or less of the resin composition by weight.

18 . The resin composition of claim 15 further comprising a crosslinker crosslinking the sidechains of the resin compound.

19 . A resin composition of the structure:

wherein
70.0 mol %≤x≤99.9 mol %,
0.01 mol %≤y≤20 mol %,
z≤10 mol %,
R 1 , R 3 , R 5 and R 6 are each independently a hydrogen atom or a methyl group,
R 2 is an alkyl, alkenyl, or aryl group having 1 to 18 carbon atoms, and
R 4 is a group having 1 to 18 carbon atoms or having 1 to 6 (meth)acryloyl groups.

20 . The resin composition of claim 19 , further comprising a cross-linker crosslinking the side-chains of the resin compound.

Assignees

• Univ California
• The Mitsubishi Chemical Corp

Inventors

• Xu Mizhi
• Iwaso Kazuhisa
• Shannon Declan
• Bates Morgan W
• Wang Hengbin
• Chatani Shunsuke
• Hawker Craig J

Classifications

• C08F2/38

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

• C08F2/06

  Organic solvent · CPC title

• C09J133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08F220/1804 Primary

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C09J7/385

  Acrylic polymers · CPC title