Use of tristyrylphenol alkoxylate sulfosuccinates in emulsion polymerization and coatings

Patent metadata

Field	Value
Publication number	US-10040964-B2
Application number	US-201615228783-A
Country	US
Kind code	B2
Filing date	Aug 4, 2016
Priority date	Feb 12, 2014
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

Disclosed are the use of novel surfactants for the synthesis of emulsion polymer latexes, particularly those used in paints, coatings, and pressure sensitive adhesives. The surfactant compositions for emulsion polymer latexes comprise sterically bulky surfactants whose composition comprises at least one alkoxylated polyaryl substituted aromatic sulfosuccinate compound. The novel surfactants provide for the production of stable, small particle size distribution emulsion polymer latexes. The resulting latexes, when formulated into latex paint, impart improvements in water resistance as measured by film opacity, blister resistance and improved leveling characteristics, and when formulated into pressure sensitive adhesives, provide improved water resistance characteristics as measured by film opacity.

First claim

We claim:

1. An emulsion comprising:
a. water;
b. at least one radical-polymerizable monomer; wherein the at least one radical-polymerizable monomer comprises (a) an amount of acrylic acid, methacrylic acid, or a mixture thereof from greater than 0 to 2% by weight based on all monomers, and (b) one or more additional monomers selected from the group consisting of vinyl monomers, acrylate monomers, methacrylatemonomers, and mixtures thereof;
c. a surfactant of one or more compounds defined by formula (I),

or a salt thereof, wherein
one of G and G 1 is —SO 3 M and the other is hydrogen, wherein M is hydrogen or a metal cation;

R is —OH, —R 1 , or —R 3 ; wherein
each R 1 is independently -L-R 2 , wherein
R 2 is

 wherein q is 1, 2, or 3, or a mixture thereof;

each L is independently —(OCH(CH 3 )CH 2 ) n —(OCH 2 CH 2 ) m —*
or —(OCH 2 CH 2 ) m —(OCH(CH 3 )CH 2 ) n —*, wherein R 2 is attached to L at the *; and
n and m are each between 0 and 100, provided that at least one of m and n is greater than or equal to 1; and
R 3 is -L-OR 4 or C 1-30 alkoxy, wherein —OR 4 is attached to L at the * and R 4 is hydrogen or C 1-4 alkyl.

2. The emulsion of claim 1 , wherein the surfactant is one or more compounds according to formula (II),

or a salt thereof.

3. The emulsion of claim 1 , wherein the surfactant is one or more compounds according to formula (III),

or a salt thereof, wherein both R 1 groups are the same.

4. The emulsion of claim 1 , wherein R 1 is —(OCH(CH 3 )CH 2 ) n —(OCH 2 CH 2 ) m —R 2 .

5. The emulsion of claim 1 , wherein R 1 is —(OCH 2 CH 2 ) m —(OCH(CH 3 )CH 2 ) n —R 2.

6. The emulsion of claim 1 , wherein R 1 is —(OCH 2 CH 2 ) m —R 2 .

7. The emulsion of claim 1 , wherein R 1 is —(OCH(CH 3 )CH 2 ) n —R 2 .

8. The emulsion of claim 1 , wherein n and m are each independently from 1 to 50.

9. The emulsion of claim 1 , wherein the surfactant is a salt.

10. The emulsion of claim 9 , wherein the surfactant is a mono- or di-sodium salt.

11. The emulsion of claim 1 , further comprising an initiator.

12. A process for preparing an emulsion polymer latex comprising, polymerizing a monomer emulsion in the presence of an initiator to form an emulsion polymer latex, wherein the monomer emulsion comprises:
a. water,
b. at least one radical-polymerizable monomer; wherein the at least one radical-polymerizable monomer comprises (a) an amount of acrylic acid, methacrylic acid, or a mixture thereof from greater than 0 to 2% by weight based on all monomers, and (b) one or more additional monomers selected from the group consisting of vinyl monomers, acrylate monomers, methacrylate monomers, and mixtures thereof; and
c. a surfactant of one or more compounds defined by formula (I),

or a salt thereof, wherein
one of G and G 1 is —SO 3 M and the other is hydrogen, wherein M is hydrogen or a metal cation;
R is —OH, —R 1 , or —R 3 ; wherein
each R 1 is independently -L-R 2 , wherein
R 2 is

 wherein q is 1, 2, or 3, or a mixture thereof;
each L is independently —(OCH(CH 3 )CH 2 ) n —(OCH 2 CH 2 ) m —*
or —(OCH 2 CH 2 ) m —(OCH(CH 3 )CH 2 ) n —*, wherein R 2 is attached to L at the *; and
n and m are each between 0 and 100, provided that at least
one of m and n is greater than or equal to 1; and

R 3 is -L-OR 4 or C 1-30 alkoxy, wherein —OR 4 is attached to L at the * and R 4 is hydrogen or C 1-4 alkyl.

13. An emulsion comprising:
a. water;
b. at least one radical-polymerizable monomer;
c. a surfactant of one or more compounds according to formula (IVa) or (IVb),

a mixture thereof, or a salt thereof, wherein
wherein M is hydrogen or a metal cation;
each R 1 is -L-R 2 , wherein
R 2 is

 wherein q is 1, 2, or 3, or a mixture thereof;

each L is independently -(OCH(CH 3 )CH 2 ) n —(OCH 2 CH 2 ) m —*
or —(OCH 2 CH 2 ) m —(OCH(CH 3 )CH 2 ) n —*, wherein R 2 is attached to L at the *; and
n and m are each between 0 and 100, provided that at least one of m and
n is greater than or equal to 1; and
R 3 is -L-OR 4 or C 1-30 alkoxy, wherein —OR 4 is attached to L at the * and R 4 is hydrogen or C 1 - 4 alkyl.

14. The emulsion of claim 13 , wherein R 3 is -L-OR 4 .

15. The emulsion of claim 13 , wherein R 3 is C 1-30 alkoxy.

16. An emulsion comprising:
a. water;
b. at least one radical-polymerizable monomer; wherein the at least one radical-polymerizable monomer comprises (a) an amount of acrylic acid, methacrylic acid, or a mixture thereof from greater than 0 to 2% by weight based on all monomers, and (b) one or more additional monomers selected from the group consisting of vinyl monomers, acrylate monomers, methacrylate monomers, and mixtures thereof;
c. a surfactant of one or more compounds defined by formula (I),

or a salt thereof, wherein
G is —SO 3 M and G 1 is hydrogen, wherein M is hydrogen or a metal cation; R is —OH or —R 1 ; wherein
each R 1 is independently -L-R 2 , wherein
R 2 is

 wherein q is a mixture of 1, 2, and 3;

each L is independently —(OCH(CH 3 )CH 2 ) n —(OCH 2 CH 2 ) m —*
or —(OCH 2 CH 2 ) m —(OCH(CH 3 )CH 2 ) n —*, wherein R 2 is attached to L at the *; and
n and m are each between 0 and 100, provided that at least one of m and
n is greater than or equal to 1; and wherein the surfactant is defined by:
a. R is —OH, G is —SO 3 Na, G 1 is hydrogen, m is 16, n is 0, and q is a mixture of 1, 2, and 3;
b. R is —OH, G is —SO 3 Na, G 1 is hydrogen, m is 4, n is 0, and q is a mixture of 1, 2, and 3;
c. R is —OH, G is —SO 3 Na, G 1 is hydrogen, m is 16, n is 1.5, and q is a mixture of 1, 2, and 3;
d. R is R 1 , G is —SO 3 Na, G 1 is hydrogen, m is 8, n is 0, and q is a mixture of 1, 2, and 3;
e. R is —OH, G is —SO3Na, G 1 is hydrogen, m is 8, n is 0, and q is a mixture of 1, 2, and 3; or f. R is —OH, G is —SO3Na, G 1 is hydrogen, m is 7, n is 8, and q is a mixture of 1, 2, and 3;
or a salt thereof.

Assignees

• Stepan Co

Inventors

• Luebke Gary
• Reschak Keith
• Luka Renee
• Kaltenbach Jarrod

Classifications

• C09J133/02

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

• C08F2/36

  Polymerisation in solid state · CPC title

• C09D5/027

  Dispersing agents (anti-settling agents C09D7/45) · CPC title

• C09D133/02

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

• C08F2/26

  anionic · CPC title