Tri-substituted aromatic-containing additives and surfactants and methods for use

Patent metadata

Field	Value
Publication number	US-9650323-B2
Application number	US-201514661814-A
Country	US
Kind code	B2
Filing date	Mar 18, 2015
Priority date	Mar 18, 2014
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

Disclosed are novel tri-substituted aromatic-alkoxylated surface active compounds. Also provided is a method of preparing an aqueous coating composition such as a latex paint including the above components.

First claim

What is claimed is:

1. A surface active compound according to structure (D.I):
R 18 —R 14 —R 13 —R 12 —R 11   (D.I)

R 12 is absent or is a bivalent linking group,
R 13 is bivalent polyether group,
R 14 is absent or is a bivalent linking group;
R 18 is an anionic group, a cationic group or a nonionic group; and
R 11 is a tri-substituted aromatic group according to the structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from the following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;
wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

2. The compound of claim 1 wherein R 18 is —OH, —OCH 3 , —OC 2 H 5 , —OC 3 H 7 , —OC 4 H 9 , —OC 5 H 11 , —OC 6 H 13 , —Cl, —Br, —CN, Phosphonate (—PO 3 − M + ), Phosphate (PO 4 − M + ), Sulfate (SO 4 − M + ), Sulfonate (SO 3 − M + ), carboxylate (COO − M + ), a nonionic group, or a quaternary ammonium ion, wherein M+ is a counterion.

3. The surface active compound of claim 1 wherein R 13 is —[CH(R 20 )CH(R 21 )O] x —, wherein x is an integer of from 0 to 100, and R 20 and R 21 are independently selected from any of the following:
H; —CH 2 OH; phenyl; —CH 2 Cl;
a C 1 -C 30 straight or branched alkyl or alkenyl;
—CH 2 OR 22 wherein R 22 is C 1 -C 30 straight or branched alkyl or alkenyl, phenyl, or alkyl substituted phenyl; or
R′COOCH 2 — where R′ is C 1 -C 30 straight or branched alkyl or alkenyl.

4. A surface active compound according to structure D.XXX:

wherein:
g is an integer from 2 to 4;
h is an integer from 2 to 4;
b is an integer from 0 to 1;
k is an integer from 0 to 100;
i is an integer from 0 to 40;
j is an integer from 0 to 40;
R 18 is an anionic group, a cationic group or a nonionic group;
R 11 is according to structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from H, any of the following structures D.XIId, D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;
wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

5. The compound according to claim 4 wherein R 18 is —OH, —OCH 3 , —OC 2 H 5 , —OC 3 H 7 , —OC 4 H 9 , —OC 5 H 11 , —OC 6 H 13 , —Cl, —Br, —CN, Phosphonate (—PO 3 − M + ), Phosphate (PO 4 − M + ), Sulfate (SO 4 − M + ), Sulfonate (SO 3 − M + ), carboxylate (COO − M + ), a nonionic group, or a quaternary ammonium ion, wherein M+ is a cation including but not limited to H + , Na + , NH 4 + , K + or Li + .

6. The compound according to claim 4 wherein:
g is an integer from 2 to 4;
h is an integer from 2 to 4;
b is an integer from 0 to 1;
k is an integer from 0 to 25;
i is an integer from 0 to 40;
j is an integer from 0 to 40;
R 11 is a tri-substituted aromatic group according to the structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from the following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 6 -C 30 branched or linear alkyl group or alkenyl group;
wherein at least one of R 1 , R 2 and R 3 is the C 6 -C 30 branched or linear alkyl group or alkenyl group and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

7. The compound of claim 1 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 6 -C 14 branched or linear alkyl group.

8. The compound of claim 4 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 6 -C 14 branched or linear alkenyl group.

9. The compound of claim 1 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 8 -C 12 branched or linear alkyl group.

10. The compound of claim 4 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 8 -C 12 branched or linear alkenyl group.

11. The compound of claim 1 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkyl group or alkenyl group.

12. The compound of claim 4 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkenyl group.

13. The compound of claim 6 wherein R 11 is a tri-substituted aromatic group according to the structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from:
a styryl group, or
a C 6 -C 30 branched or linear alkyl group or alkenyl group;

wherein at least one of R 1 , R 2 and R 3 is the C 6 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is the styryl group.

14. The compound of claim 1 wherein R 11 is a tri-substituted aromatic group according to the structure D.XII-1

wherein R 1 , is the C 4 -C 30 branched or linear alkyl group or alkenyl group.

15. The compound of claim 14 wherein the C 4 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkyl group or alkenyl group.

16. A low VOC latex coating composition comprising:
(a) at least one latex polymer;
(b) optionally, at least one pigment;
(c) water; and
(d) an additive present in an amount effective to impart freeze-thaw stability, having structure D.XII

wherein R 1 , R 2 and R 3 are independently selected from H, any of following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

or a C 4 -C 30 branched or linear alkyl group or alkenyl group;
wherein at least one of R 1 , R 2 and R 3 is the C 4 -C 30 branched or linear alkyl group or alkenyl group, and at least one of R 1 , R 2 and R 3 is selected from structure D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

17. A method for imparting freeze-thaw stability on a low VOC coating composition comprising adding to the composition an effective amount of an additive according to structural formula D.XII

wherein R 1 , R 2 and R 3 are independently selected from H, any of following structures D.XIIIa, D.XIIIb, D.XIIIc, D.XIIId:

Assignees

• Rhodia Operations

Inventors

• Anderson Jr Eugene J
• Pakenham Derek
• Martinez-Castro Nemesio
• Ruiz Jose P
• Rhodes Michael
• Zhou Lichang

Classifications

• C08F220/306

  and polyethylene oxide chain in the alcohol moiety · CPC title

• C07C43/2055 Primary

  containing more than one ether bond · CPC title

• C08K5/13 Primary

  Phenols; Phenolates · CPC title

• C07C37/14

  by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title