Tri-substituted aromatic-containing monomers, copolymers and methods for use

Patent metadata

Field	Value
Publication number	US-10029967-B2
Application number	US-201514661808-A
Country	US
Kind code	B2
Filing date	Mar 18, 2015
Priority date	Mar 18, 2014
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Disclosed are novel tri-substituted aromatic-alkoxylated monomers, polymers made with the novel tri-substituted aromatic-alkoxylated monomers, pH responsive polymers made with the novel tri-substituted aromatic-alkoxylated monomers, and related methods. Also disclosed is an aqueous coating composition including at least one latex polymer derived from at least one monomer copolymerized or blended with alkali swellable acrylate copolymer. 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):
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 a moiety having a site of ethylenic unsaturation; 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 9 -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 9 -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 ethylenically unsaturated monomer 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.

3. The ethylenically unsaturated monomer of claim 1 wherein the monomer is 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 a moiety having a site of ethylenic unsaturation;
R 11 is according to 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 9 -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 9 -C 30 branched or alkyl group or alkenyl group and at least one of R 1 , R 2 and R 3 is selected from D.XIIIa, D.XIIIb, D.XIIIc, or D.XIIId.

4. The monomer of claim 3 wherein R 18 is according to structure (D.XV):

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

5. The monomer of claim 1 wherein the C 9 -C 30 branched or linear alkyl group or alkenyl group is a C 10 -C 30 branched or linear alkyl group.

6. The monomer of claim 1 wherein the C 9 -C 30 branched or linear alkyl group or alkenyl group is a C 10 -C 24 branched or linear alkenyl group.

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

9. The monomer of claim 1 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 9 -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 9 -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.

10. The monomer 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 9 -C 30 branched or linear alkyl group or alkenyl group.

11. The monomer of claim 10 wherein the C 9 -C 30 branched or linear alkyl group or alkenyl group is a C 9 -C 14 branched or linear alkyl group or alkenyl group.

12. A copolymer comprising at least one monomer according to structure D.XVI:

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 19 is hydrogen; methyl or ethyl;
R 11 is according to 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 9 -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 9 -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, D.XIIId.

13. A pH responsive 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, preferably a C 3 -C 8 alpha beta-ethylenically unsaturated carboxylic acid 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 nonionic ethylenically unsaturated hydrophobic monomer according to claim 1 .

14. The pH responsive copolymer of claim 13 , 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, preferably a C 3 -C 8 alpha beta-ethylenically unsaturated carboxylic acid 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 the at least one ethylenically unsaturated hydrophobic monomer according to structure D.XVI:

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 19 is hydrogen; methyl or ethyl;
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 2 -C 30 branched or linear alkyl group or al

Assignees

• Rhodia Operations

Inventors

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

Classifications

• C08F220/306

  and polyethylene oxide chain in the alcohol moiety · CPC title

• C07C37/14

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

• C07C41/03

  by reaction of oxirane rings with hydroxy groups · CPC title

• C07C43/2055 Primary

  containing more than one ether bond · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title