Substituted catechol additives in coatings and methods for use

Patent metadata

Field	Value
Publication number	US-11613508-B2
Application number	US-201916556584-A
Country	US
Kind code	B2
Filing date	Aug 30, 2019
Priority date	Aug 30, 2018
Publication date	Mar 28, 2023
Grant date	Mar 28, 2023

Abstract

Disclosed are novel catechol dditives and the like, methods of preparing, as well as compositions and methods using such compositions in various applications. 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):

wherein
R 1 and R 5 are independently absent or a bivalent linking group,
R 2 and R 6 are independently a bivalent polyether group,
R 3 and R 7 are independently absent or a bivalent linking group, and
R 4 and R 8 are independently an anionic group, a cationic group or a nonionic group; and
wherein R 9 and R 10 are independently selected from the following structures D.Ia, D.Ib, D.Ic, D.Id:

or a C 2 -C 30 branched or linear alkyl group or alkenyl group.

2. The compound of claim 1 , wherein R 4 and R 8 are independently selected from —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 2 and R 6 are independently selected from —[CH(R 20 )CH(R 21 )O] x —, wherein x is an integer of from 2 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. The surface active compound of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 3 -C 14 branched or linear alkyl group.

5. The surface active compound of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 6 -C 14 branched or linear alkyl group.

6. The surface active compound of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 8 -C 12 branched or linear alkyl group.

7. The surface active compound of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 4 -C 12 branched or linear alkyl group or alkenyl group.

8. 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.I):

wherein
R 1 and R 5 are independently absent or a bivalent linking group,
R 2 and R 6 are independently a bivalent polyether group,
R 3 and R 7 are independently absent or a bivalent linking group, and
R 4 and R 8 are independently an anionic group, a cationic group or a nonionic group; and
wherein R 9 and R 10 are independently selected from the following structures D.Ia, D.Ib, D.Ic, D.Id:

or a C 2 -C 30 branched or linear alkyl group or alkenyl group.

9. A method for imparting freeze-thaw stability on a low VOC coating composition comprising adding to the composition an additive according to structure (D.I):

wherein
R 1 and R 5 are independently absent or a bivalent linking group,
R 2 and R 6 are independently a bivalent polyether group,
R 3 and R 7 are independently absent or a bivalent linking group, and
R 4 and R 8 are independently an anionic group, a cationic group or a nonionic group; and
wherein R 9 and R 10 are independently selected from the following structures D.Ia, D.Ib, D.Ic, D.Id:

or a C 2 -C 30 branched or linear alkyl group or alkenyl group;
wherein the low VOC comprises at least one latex polymer, water and, optionally, at least one pigment.

10. The method of claim 9 comprising greater than 0.5% of the additive by weight of the polymer.

11. The method of claim 9 comprising greater than 1.3% of the additive by weight of the polymer.

12. The method of claim 9 comprising greater than 1.6% of the additive by weight of the polymer.

13. The method of claim 9 comprising greater than 1% of the additive by weight of the polymer.

14. The composition of claim 8 comprising greater than 0.5% of the additive by weight of the polymer.

15. The composition of claim 8 comprising greater than 1.3% of the additive by weight of the polymer.

16. The composition of claim 8 comprising greater than 1.6% of the additive by weight of the polymer.

17. The composition of claim 8 comprising greater than 1% of the additive by weight of the polymer.

18. The surface active compound of claim 1 wherein the R 4 and R 8 are independently an anionic group.

19. The surface active compound of claim 1 wherein the R 4 and R 8 are independently a cationic group.

20. The surface active compound of claim 1 wherein the R 4 and R 8 are independently a nonionic group.

21. The surface active compound of claim 1 ,
wherein R 4 and R 8 are independently selected from
—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,
alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aryl, arylalkyl, or aryloxy,
alkenyl, aralkyl, alkaryl, a hetero atom, or heterocyclyl, or with one or more functional groups selected from hydroxyl, carbonyl, carboxyl, amino, imino, amido, phosphonic acid, sulphonic acid, or inorganic and organic esters thereof;

wherein R 2 and R 6 are independently selected from
a bivalent polyether group comprising a linear chain of from 2 to 100 units, each of which may independently be (C 2 —C 4 )oxyalkylene,
—[CH(R 20 )CH(R 21 )O] x − , wherein x is an integer of from 2 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,
wherein R 1, R 3, R 5, R 7 are independently the bivalent linking group selected from —(CH 2 ) x O—, wherein x is an integer from 1 to 20, —CH 2 CH(OH)CH 2 O—or —CH 2 CH(CH 2 OH)O—.

Assignees

• Rhodia Operations

Inventors

• Anderson Eugene J
• Martinez-Castro Nemesio
• Zhou Lichang

Classifications

• C09D7/45

  Anti-settling agents · CPC title

• C08L71/12

  Polyphenylene oxides · CPC title

• C07C43/2055 Primary

  containing more than one ether bond · CPC title

• C09D5/024

  characterised by the additives · CPC title

• C07C43/21

  containing rings other than six-membered aromatic rings · CPC title