Monomer composition containing unsaturated polyalkylene glycol ether-based monomer, method for producing composition thereof, polymer obtained using composition thereof, and method for producing polymer thereof

Patent metadata

Field	Value
Publication number	US-9850378-B2
Application number	US-201113876665-A
Country	US
Kind code	B2
Filing date	Sep 22, 2011
Priority date	Sep 30, 2010
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A monomer composition containing an unsaturated polyalkylene glycol ether-based monomer is provided having excellent stability. The monomer composition contains an unsaturated polyalkylene glycol ether-based monomer represented by the following chemical formula (1):

YO(R 1 O) n R 2   (1)

[in the formula, Y represents an alkenyl group having 2 to 7 carbon atoms; R 1 O represents one or two or more types of oxyalkylene groups having 2 to 18 carbon atoms; n represents an average addition mole number of oxyalkylene groups and is a number of 5 to 500; and R 2 represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms], an organic acid, and water, and having a pH of 4 to 13.

First claim

The invention claimed is:

1. A method for producing the monomer composition, the method comprising:
a reaction step for reacting alkenyl alcohol with alkylene oxide having 2 to 18 carbon atoms in the presence of an alkali catalyst to give an unsaturated polyalkylene glycol ether-based monomer, said alkenyl alcohol; selected from the groups consisting of 3-methyl-3-buten-1-ol (CH 2 ═C(CH 3 )—CH 2 CH 2 —OH), 2-methyl-3-buten-1-ol (CH 2 ═CHCH(CH 3 )—CH 2 —OH), 5-hexen-1-ol (CH 2 ═CHCH 2 CH 2 CH 2 CH 2 —OH), and 3-hepten-1-ol (CH 2 CH 2 CH 2 CH═CHCH 2 CH 2 —OH);
a concentration adjustment step for adding water to the reaction liquid obtained from the reaction step to yield an aqueous solution: and
a neutralization step for neutralizing the reaction liquid obtained from the reaction step to pH 4 to pH 13 by using an organic acid, wherein the organic acid is a hydrocarbon having 1 to 10 carbon atoms and has a carboxy group or a sulfo group.

2. A method for producing a polycarboxylic acid-based polymer, the method comprising:
a reaction step for reacting alkenyl alcohol with alkylene oxide having 2 to 18 carbon atoms in the presence of an alkali catalyst to give an unsaturated polyalkylene glycol ether-based monomer, said alkenyl alcohol selected from the group consisting of 3-methyl-3-buten-1-ol (CH 2 ═C(CH 3 )—CH 2 CH 2 —OH), 2-methyl-3-buten-1-ol (CH 2 ═CHCH(CH 3 )—CH 2 —OH), 5-hexen-1-ol (CH 2 ═CHCH 2 CH 2 CH 2 CH 2 —OH), and 3-hepten-1-ol (CH 3 CH 2 CH 2 CH═CHCH 2 CH 2 —OH);
a concentration adjustment step for adding water to the reaction liquid obtained from the reaction step to yield an aqueous solution;
a neutralization step for neutralizing the reaction liquid obtained from the reaction step to pH 4 to pH 13 by using an organic acid, wherein the organic acid is a hydrocarbon having 1 to 10 carbon atoms and has a carboxy group or a sulfo group; and
a polymerization step for obtaining the polycarboxylic acid-based polymer by using the monomer composition obtained after the neutralization step and reacting the unsaturated polyalkylene glycol ether-based monomer contained in the monomer composition with the unsaturated acid-based monomer represented by the following chemical formula (2):

[in the formula,
R 3 , R 4 , and R 5 each independently represent a hydrogen atom, a methyl group, or a —(CH 2 ) p COOH group (here, p is an integer of from 0 to 2); and
M represents a hydrogen atom, a metal atom, an ammonium group, or an organic amine group].

3. A method for producing a polycarboxylic acid-based polymer according to claim 2 , wherein a time interval between end of the neutralization step and beginning of the polymerization step is 6 hours or more.

4. The method according to claim 2 , wherein the organic acid is a hydrocarbon having 1 to 10 carbon atoms which has a sulfo group.

5. The method according to claim 2 , wherein the organic acid is selected from the group consisting of acetic acid, phenylacetic acid, phenoxyacetic acid, chloroacetic acid, propionic acid (propane acid), 2-bromopropane acid, 3-phenylpropane acid, lactic acid, butyric acid (butanoic acid), benzoic acid, phthalic acid, terephthalic acid, salicylic acid (2-hydroxybenzoic acid), acetylsalicylic acid (2-acetoxybenzoic acid), citric acid, gluconic acid, methane sulfonic acid, ethane sulfonic acid, benzene sulfonic acid, p-chlorobenzene sulfonic acid, p-toluene sulfonic acid, p-phenol sulfonic acid, and 4-nitrobenzene sulfonic acid.

6. The method according to claim 2 , wherein the organic acid is p-toluene sulfonic acid.

7. The method according to claim 2 , wherein a content of the organic acid is 0.0001 to 5 parts by weight relative to 100 parts by weight of the monomer.

8. The method according to claim 2 , wherein a content of the water is 1 to 50 parts by weight relative to 100 parts by weight of the monomer.

9. The method according to claim 2 , wherein an alkali metal ion is included in an amount of 5 to 30,000 ppm by weight.

10. The method according to claim 2 , wherein a time interval between end of the neutralization process and start of the polymerization process is 240 hours or more.

11. The method according to claim 2 , wherein a temperature of the monomer composition is 50 to 90° C. between end of the neutralization process and start of the polymerization process.

Assignees

• Kawabata Hiroshi
• Nippon Catalytic Chem Ind

Inventors

• Kawabata Hiroshi

Classifications

• C08G65/30

  Post-polymerisation treatment, e.g. recovery, purification, drying · CPC title

• C08L71/02 Primary

  Polyalkylene oxides · CPC title

• C08L33/02

  Homopolymers or copolymers of acids; Metal or ammonium salts thereof · CPC title

• C04B24/2647

  containing polyether side chains · CPC title

• C08F228/02

  by a bond to sulfur · CPC title