Reactive surfactant composition for emulsion polymerization

Patent metadata

Field	Value
Publication number	US-11345764-B2
Application number	US-202016923186-A
Country	US
Kind code	B2
Filing date	Jul 8, 2020
Priority date	Oct 9, 2015
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

The present invention is concerned with a reactive surfactant composition for emulsion polymerization, which is able to micronize the particle diameter of a polymer emulsion and to reduce the addition amount of the reactive surfactant composition to be used. The reactive surfactant composition for emulsion polymerization of the present invention contains a reactive anionic surfactant (component A) represented by the following formula (I):

wherein AO represents an alkyleneoxy group having a carbon number of 3 or more and 18 or less; EO represents an ethyleneoxy group; p represents an integer of 1 or more and 15 or less; m′ represents an integer of 0 or more; n′ represents an integer of 0 or more; M + represents a hydrogen ion or a cation; and plural kinds of AOs may coexist.

First claim

The invention claimed is:

1. A method of producing a reactive anionic surfactant, comprising the following steps (i) to (iii), the reactive anionic surfactant being represented by the following formula (1) and being satisfied with the following requirement R (provided that in the requirement R, when n is 0, then the step (ii) is not performed):
Step (i): a step of adding an alkylene oxide having a carbon number of 4 or more and 18 or less to a compound represented by the following formula (2) in the presence of an aluminum-magnesium complex oxide catalyst to thereby obtain a compound represented by the following formula (3);
Step (ii): a step of adding ethylene oxide to the compound represented by the following formula (3) in the presence of an alkali catalyst to thereby obtain a compound represented by the following formula (4); and
Step (iii): a step of sulfating the compound represented by the following formula (4) with a sulfating agent and neutralizing with a basic substance:

wherein AO represents an alkyleneoxy group having a carbon number of 4 or more and 18 or less; EO represents an ethyleneoxy group; p represents an integer of 1 or more and 15 or less; m′ represents an integer of 0 or more; n′ represents an integer of 0 or more; M + represents a hydrogen ion or a cation; and plural kinds of AOs may coexist: and
Requirement R: an average addition molar number m of AO is a number of 1 or more and 50 or less; an average addition molar number n of EO is a number of 0 or more and 200 or less; and when in the compound represented by the formula (1) (component A), a component having an addition molar number of AO of (m−3) or less is defined as (component A-1), and a component having an addition molar number of AO of (m+2) or more is defined as (component A-2), X in the following formula (I) is less than 30, provided that when m is less than 3, (m′=0) is defined as (component A-1):
X ={(molar number of component A -1)+(molar number of component A -2)}÷(molar number of component A )×100  (I).

2. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the formula (1), m′ is an integer of 1 or more and an integer of 100 or less.

3. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the formula (1), m′ is an integer of 2 or more and an integer of 50 or less.

4. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the formula (1), n′ is an integer of 1 or more and an integer of 400 or less.

5. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the formula (1), n′ is an integer of 2 or more and an integer of 200 or less.

6. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the formula (1), the carbon number of the alkyleneoxy group represented by AO is 8 or less.

7. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the requirement R, m is 2 or more and 20 or less.

8. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the requirement R, m is 3 or more and 10 or less.

9. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the requirement R, n is 1 or more and 150 or less.

10. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the requirement R, (m+n) is {3≤(m+n)≤100}.

11. The method of producing a reactive anionic surfactant according to claim 1 , wherein in the formula (1), X is 10 or more and 29 or less.

12. The method of producing a reactive anionic surfactant according to claim 1 , wherein a reaction temperature in Step (i) is 70° C. or higher and 150° C. or lower.

13. The method of producing a reactive anionic surfactant according to claim 1 , wherein the use amount of the catalyst in Step (i) is 0.05% by mass or more and 20% by mass or less relative to the compound represented by the formula (2).

14. The method of producing a reactive anionic surfactant according to claim 1 , wherein the compound represented by the formula (2) is 3-methyl-3-buten-1-ol.

15. The method of producing a reactive anionic surfactant according to claim 1 , wherein after Step (i), there is a step in which the reaction product is cooled, and water or a filter aid for the purpose of reducing the viscosity is added, followed by filtration of the catalyst.

16. The method of producing a reactive anionic surfactant according to claim 1 , wherein in Step (ii) the pressure is 0.1 MPa or more and 3 MPa or less, and the reaction temperature is 60° C. or higher and 200° C. or lower.

17. The method of producing a reactive anionic surfactant according to claim 1 , wherein in Step (iii) the compound represented by the formula (4) is sulfated with a sulfating agent in the presence of an amide compound (exclusive of a sulfonic acid amide compound) or an amine compound at the temperature of 60° C. or higher and 140° C. or lower.

18. The method of producing a reactive anionic surfactant according to claim 1 , wherein in Step (iii) the sulfating agent is amidosulfuric acid.

19. A method of producing a polymer emulsion, comprising subjecting a radical polymerizable monomer to emulsion polymerization in the presence of the reactive anionic surfactant obtained by the method according to claim 1 .

20. The method of producing a polymer emulsion according to claim 19 , wherein the use amount of the reactive anionic surfactant is 0.1% by mass or more and 10% by mass or less relative to the total amount of the radical polymerizable monomer.

Assignees

• Kao Corp

Inventors

• Kamenoue Shogo
• Ikenaga Takayuki
• Mori Atsuhito

Classifications

• C08F2/26 Primary

  anionic · CPC title

• C09K23/04

  Sulfonates or sulfuric acid ester salts derived from polyhydric alcohols or amino alcohols or derivatives thereof (sulfated or sulfonated fatty oils C09K23/08) · CPC title

• C08F290/062

  Polyethers · CPC title

• C09D133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C09D125/14

  with unsaturated esters · CPC title