Anionic polymerization process and polymer production method

Patent metadata

Field	Value
Publication number	US-12281185-B2
Application number	US-201917271431-A
Country	US
Kind code	B2
Filing date	Aug 22, 2019
Priority date	Aug 27, 2018
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

A process for anionically polymerizing a (meth)acrylic acid in the presence of a tertiary organoaluminum compound (A), an organolithium compound (B) and at least one kind of a Lewis base (C) in a polymerization system. The tertiary organoaluminum compound (A) includes a tertiary organoaluminum compound (A1) having a chemical structure in which at least two of three unshared electrons of an aluminum atom are bonded to an aromatic ring via an oxygen atom, and the tertiary organoaluminum compound (A) has a molar ratio (A2)/(A1) in the range of 0% or above and 0.8% or below between a tertiary organoaluminum compound (A2) having a chemical structure in which at most one of three unshared electrons of an aluminum atom is bonded to an aromatic ring via an oxygen atom, and the tertiary organoaluminum compound (A1).

First claim

The invention claimed is:

1. A process, comprising:
anionically polymerizing a (meth)acrylic acid ester in the presence of a tertiary organoaluminum compound (A), 1-methylpropyllithium, and a Lewis base in a polymerization system, to produce a polymer,
wherein the tertiary organoaluminum compound (A) comprises isobutylbis(2,6-di-t-butyl-4-methylphenoxy)aluminum (A1) and diisobutyl(2,6-di-t-butyl-4-methylphenoxy)aluminum (A2), and
wherein an (A2)/(A1) molar ratio of the tertiary organoaluminum compound (A), based on moles of isobutylbis(2,6-di-t-butyl-4-methylphenoxy)aluminum (A1) and moles of diisobutyl(2,6-di-t-butyl-4-methylphenoxy)aluminum (A2) is in a range of from more than 0 to 0.8%.

2. The process of claim 1 , wherein the (A2)/(A1) molar ratio is in a range of from 0.001 to 0.8%.

3. The process of claim 1 , wherein the Lewis base comprises a tertiary polyamine compound.

4. The process of claim 3 , wherein the tertiary polyamine compound comprises N,N,N′,N′-tetramethylethylenediamine, N,N,N′,N″,N″-pentamethyldiethylenetriamine, and/or 1,1,4,7,10,10-hexamethyltriethylenetetramine.

5. The process of claim 1 , wherein the Lewis base comprises an ether compound.

6. The process of claim 5 , wherein the ether compound comprises an acyclic ether compound having one or more ether bonds in a molecule thereof or a cyclic ether compound having two or more ether bonds in the molecule.

7. The process of claim 1 , wherein the Lewis base comprises N,N,N′,N′-tetramethylethylenediamine.

8. The process of claim 1 , wherein the Lewis base comprises N,N,N′,N″,N″-pentamethyldiethylenetriamine.

9. The process of claim 1 , wherein the Lewis base comprises 1,1,4,7,10,10-hexamethyltriethylenetetramine.

10. The process of claim 1 , wherein the (A2)/(A1) molar ratio is in a range of from 0.001 to 0.5%.

11. The process of claim 1 , wherein the (A2)/(A1) molar ratio is in a range of from 0.001 to 0.3%.

12. The process of claim 1 , wherein the (A2)/(A1) molar ratio is in a range of from 0.00438 to 0.505%.

13. The process of claim 1 , wherein the (A2)/(A1) molar ratio is in a range of from 0.00438 to 0.307%.

14. The process of claim 1 , wherein no gel forms in the anionically polymerizing.

15. The process of claim 1 , wherein the anionically polymerizing is performed twice to produce a diblock copolymer.

16. The process of claim 15 , wherein the diblock copolymer has a polydispersity index in a range of from 1.20 to 1.31.

17. The process of claim 1 , which has a polymerization initiation efficiency in a range of from 0.85 to 0.98.

18. The process of claim 1 , wherein the (A2)/(A1) molar ratio is in a range of from 0.00438 to 0.731%.

19. A method for producing a polymer, the method comprising:
polymerizing a (meth)acrylic acid ester by the process of claim 1 .

20. A method for producing a block copolymer, the method comprising:
polymerizing two or more kinds of (meth)acrylic acid esters by the process of claim 1 .

Assignees

• Kuraray Co

Inventors

• Kawahara Moe
• Ono Tomohiro

Classifications

• C08K5/56

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C08F2438/00

  Living radical polymerisation · CPC title

• C08F297/026 Primary

  polymerising acrylic acid, methacrylic acid or derivatives thereof · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title