Chain transfer agent and emulsion polymerization using the same

Patent metadata

Field	Value
Publication number	US-9452978-B2
Application number	US-201113575775-A
Country	US
Kind code	B2
Filing date	Jan 27, 2011
Priority date	Jan 27, 2010
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

To provide a novel compound having both a surface-activating ability and a polymerization controlling ability.
A compound represented by the following general formula (1) or (2):

wherein, R 1 and R 3 are an organic group having the hydrophile-lipophile balance (HLB) determined by Griffin's method of 3 or more. The definitions of R 1 , R 2 , R 3 , R 4 , Z, p and q are described in the Description.

First claim

The invention claimed is:

1. A method for radical-polymerizing a vinyl monomer, the method comprising:
radical-polymerizing a vinyl monomer with the compound of formula (1):

wherein:
R 1 represents an organic group having a hydrophile-lipophile balance (HLB) determined by Griffin's method of 3 or more, wherein the organic group comprises polyethylene glycol, polypropylene glycol, or a polyethylene glycol/polypropylene glycol block copolymer and optionally comprising a carboxylic acid metal salt or sulfonic acid metal salt;
Z represents an unsubstituted aromatic hydrocarbon group;
when a plurality of R 1 are present, they may be the same or different;
p is represented by an integer of 1 or more; and
R 2 is a p-valent organic group having one or more carbons, and said p-valent organic group optionally comprises at least one selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a halogen atom, a silicon atom, a phosphorous atom, and a metal atom.

2. The method according to claim 1 , wherein the radical polymerizing comprises emulsion polymerization.

3. A method for radical polymerizing a vinyl monomer, the method comprising:
preparing an aqueous solution comprising a compound of fommla (1) and an emulsifying agent in the absence of a vinyl monomer, to obtain a mixed micelle comprising the emulsifying agent and the compound of formula (1); and then
adding a vinyl monomer to the aqueous solution comprising the mixed micelle and emulsion polymerizing the vinyl monomer.

wherein:
R 1 represents an organic group having a hydrophile-lipophile balance (HLB) determined by Griffin's method of 3 or more, wherein the organic group comprises polyethylene glycol, polypropylene glycol, or a polyethylene glycol/polypropylene glycol block copolymer and optionally comprising a carboxylic acid metal salt or sulfonic acid metal salt, wherein when a plurality of R 1 are present, they may be the same or different;
Z represents an unsubstituted aromatic hydrocarbon group;
p is represented by an integer of 1 or more; and
R 2 is a p-valent organic group having one or more carbons, and said p-valent organic group optionally comprises at least one selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a halogen atom, a silicon atom, a phosphorous atom, and a metal atom.

4. The method according to claim 1 , wherein after a first vinyl monomer or a mixture thereof is polymerized, a second vinyl monomer or a mixture thereof is newly added to produce a diblock copolymer.

5. The method according to claim 1 , wherein after a first vinyl monomer or a mixture thereof is polymerized, a second vinyl monomer or a mixture thereof is added and polymerized, and then a vinyl monomer or a mixture thereof is added and polymerized in multi stages to produce a multiblock copolymer.

6. The method according to claim 1 , wherein, in formula (1), R 2 is an unsubstituted hydrocarbon group, an unsubstituted aromatic hydrocarbon, or a cyano group.

7. The method according to claim 1 , wherein, in formula (1), R 2 is a group of the formula:

wherein, R 21 and R 22 are each independently alkyl groups having 1-8 carbon.

8. The method according to claim 7 , wherein, R 21 and R 22 are each a methyl group.

9. The method of claim 1 , wherein, in formula (1), p is 2.

10. The method of claim 1 , wherein, in formula (1), Z is a phenyl group.

11. The method of claim 1 , wherein, in formula (1), R 1 has an HLB value determined by Griffin's method of 11.1 or more.

12. The method of claim 1 , wherein, in formula (1), R 1 has an HLB value determined by Griffi's method of 17.3 or more.

Assignees

• Noda Tetsuya
• Nakaya Fuminori
• Sakashita Keiichi
• Matsunaga Yosuke
• Oonuma Taeko
• Irie Yoshiko
• Mitsubishi Rayon Co

Inventors

• Noda Tetsuya
• Nakaya Fuminori
• Sakashita Keiichi
• Matsunaga Yosuke
• Oonuma Taeko
• Irie Yoshiko

Classifications

• C08F8/08

  Epoxidation · CPC title

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C08F6/14

  Treatment of polymer emulsions {(C08F6/001, C08F6/006, C08F6/008, C08F6/02, C08F6/04 take precedence)} · CPC title

• C08F2/26

  anionic · CPC title

• C08F20/14

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