Tri-substituted aromatic-containing polymeric dispersants

Patent metadata

Field	Value
Publication number	US-10131605-B2
Application number	US-201514661957-A
Country	US
Kind code	B2
Filing date	Mar 18, 2015
Priority date	Mar 18, 2014
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

Disclosed are novel tri-substituted aromatic-alkoxylated polymeric dispersants and related method of preparing. Also disclosed are methods of dispersing at least one pigment comprising the following steps: contacting an aqueous solution containing at least one pigment with the polymeric dispersant copolymers as described herein.

First claim

What is claimed is:

1. A polymeric dispersant 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 5 -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 5 -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; and
wherein the polymeric dispersant has a weight average molecular weight of between 2,000 g/mole to 25,000 g/mole.

2. The polymeric dispersant of claim 1 wherein the weight average molecular weight is between 2,000 g/mole to 15,000 g/mole.

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

4. The polymeric dispersant of claim 1 wherein the C 5 -C 30 branched or linear alkyl group or alkenyl group is a C 6 -C 14 branched or linear alkyl group.

5. The polymeric dispersant of claim 1 wherein the C 5 -C 30 branched or linear alkyl group or alkenyl group is a C 9 -C 14 branched or linear alkenyl group.

6. The polymeric dispersant of claim 1 wherein the C 5 -C 30 branched or linear alkyl group or alkenyl group is a C 8 -C 12 branched or linear alkyl group.

7. The polymeric dispersant of claim 1 wherein the C 5 -C 30 branched or linear alkyl group or alkenyl group is a C 23 -C 30 branched or linear alkenyl group.

8. The polymeric dispersant 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 5 -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 5 -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.

9. The polymeric dispersant 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 5 -C 30 branched or linear alkyl group or alkenyl group.

10. The polymeric dispersant of claim 1 wherein the polymeric dispersant is characterized as an oligomer.

11. A polymeric dispersant copolymer, comprising, based on total weight of monomers:
A. about 0-60 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 0.01-30 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 5 -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 5 -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; and
wherein the polymeric dispersant has a weight average molecular weight of between 2,000 g/mole to 25,000 g/mole.

12. The polymeric dispersant copolymer of claim 11 wherein the weight average molecular weight is between 2,000 g/mole to 15,000 g/mole.

13. The polymeric dispersant copolymer of claim 11 wherein the carboxylic acid monomer (A) is present from about 15 weight percent to about 60 weight percent based on total monomer weight.

14. The polymeric dispersant copolymer of claim 11 wherein the carboxylic acid monomer (A) is selected from a group consisting of methacrylic acid, acrylic acid and a combination thereof.

15. The polymeric dispersant copolymer of claim 11 wherein the nonionic monomer (B) is alkyl acrylate.

16. A method for dispersing pigments in an aqueous emulsion, comprising: contacting
(i) an aqueous emulsion containing at least one pigment with
(ii) a polymeric dispersant copolymer, comprising, based on total weight of monomers:
A. about 0-60 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 0.01-30 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 5 -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 2 -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; and
wherein the polymeric dispersant has a weight average molecular weight of between 2,000 g/mole to 25,000 g/mole.

17. The method of claim 16 wherein the pigment is carbon black.

18. The method of cl

Assignees

• Rhodia Operations

Inventors

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

Classifications

• C08F220/306

  and polyethylene oxide chain in the alcohol moiety · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07C37/14

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

• C07C43/2055 Primary

  containing more than one ether bond · CPC title

• C08K5/13 Primary

  Phenols; Phenolates · CPC title