Chain transfer agent and emulsion polymerization using the same
View Patent ↗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.
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.