Substituted catechol monomers, copolymers and methods for use

Patent metadata

Field	Value
Publication number	US-11623972-B2
Application number	US-201916556590-A
Country	US
Kind code	B2
Filing date	Aug 30, 2019
Priority date	Aug 30, 2018
Publication date	Apr 11, 2023
Grant date	Apr 11, 2023

Abstract

Disclosed are novel substituted catechol monomers, polymers made with the substituted catechol monomers, pH responsive polymers made with the substituted catechol monomers, and related methods. 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. An ethylenically unsaturated monomer 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 a moiety having a site of ethylenic unsaturation;
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 monomer 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 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.

3. The monomer of claim 1 wherein R 4 and R 8 are independently according to structure (D.XV):

wherein R 19 is H or (C 1 -C 4 )alkyl.

4. The monomer 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 monomer of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 9 -C 30 branched or linear alkenyl group.

6. The monomer 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.

7. The monomer of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 9 -C 14 branched or linear alkenyl group.

8. The monomer 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.

9. The monomer of claim 1 wherein the C 2 -C 30 branched or linear alkyl group or alkenyl group is a C 23 -C 30 branched or linear alkenyl group.

10. The monomer 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.

11. A copolymer of unsaturated copolymerizable monomers, said unsaturated copolymerizable monomers comprising, based on total weight of monomers:
A. about 0-60 weight percent of at least one C 3 -C 8 alpha beta-ethylenically unsaturated acidic monomer;
B. about 15-70 weight percent of at least one nonionic, copolymerizable C 2 -C 12 alpha, beta-ethylenically unsaturated monomer; and
C. about 0.05 to 30 weight percent of at least one ethylenically unsaturated monomer according to claim 1 wherein the ethylenically unsaturated monomer is nonionic and hydrophobic.

12. The copolymer of claim 11 , wherein the copolymer is pH responsive.

13. The copolymer of claim 11 , comprising, based on total weight of monomers:
A. about 5 to 60 weight percent of the at least one C 3 -C 8 alpha beta-ethylenically unsaturated acidic monomer;
B. about 15-70 weight percent of the at least one non-ionic, copolymerizable C 2 -C 12 alpha, beta-ethylenically unsaturated monomer; and
C. about 0.05 to 30 weight percent of at least one ethylenically unsaturated monomer according to claim 1 wherein the ethylenically unsaturated monomer is nonionic and hydrophobic.

14. The copolymer of claim 13 , wherein the at least one C 3 -C 8 alpha beta-ethylenically unsaturated acidic monomer (A) is present from about 25 weight percent to about 60 weight percent based on total monomer weight.

15. The copolymer of claim 13 wherein the at least one C 3 -C 8 alpha beta-ethylenically unsaturated acidic monomer (A) is selected from a group consisting of methacrylic acid, acrylic acid and a combination thereof.

16. The copolymer of claim 13 wherein the nonionic monomer (B) is alkyl acrylate.

17. An aqueous composition, comprising water and the pH responsive copolymer of claim 12 .

18. A method for thickening an aqueous emulsion, comprising: forming a blend by blending with the aqueous emulsion an amount of the pH-responsive copolymer of claim 12 to thicken the aqueous emulsion when pH of the blend is adjusted to a pH in the range of about 6.5 to about 11.

19. The copolymer of claim 11 , wherein the at least one C 3 -C 8 alpha beta-ethylenically unsaturated acidic monomer is at least one C 3 -C 8 alpha beta-ethylenically unsaturated carboxylic acid monomer.

20. The copolymer of claim 13 , wherein the at least one C 3 -C 8 alpha beta-ethylenically unsaturated acidic monomer is at least one C 3 -C 8 alpha beta-ethylenically unsaturated carboxylic acid monomer.

Assignees

• Rhodia Operations

Inventors

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

Classifications

• C08F2/22

  Emulsion polymerisation · CPC title

• C09D133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C08F2/24 Primary

  with the aid of emulsifying agents · CPC title

• C09D5/02

  Emulsion paints {including aerosols} · CPC title