Granted Patent B2

US 12,365,808 · App. 17/533,206 · Granted Jul 22, 2025

Inventors: Genggeng Qi (Webster, NY); Yu Qi (Penfield, NY); Chieh-Min Cheng (Rochester, NY)

C09D11/326C08F220/06C08F220/1807C08F220/1818C08F220/286C08F220/56C09D11/033C09D11/107

Abstract

Claims (207)

1. A self-crosslinked polymeric dispersant comprising:

a copolymer comprising:

an acid group;

a base group;

a hydrophobic group selected from a member of the group consisting of an alkyl group having from about 4 to about 40 carbon atoms; an aromatic group; and combinations thereof; and

a steric hydrophilic group.

2. The polymeric dispersant of claim 1 , wherein the acid group is selected from a member of the group consisting of carboxylic acid, phosphoric acid, sulphonic acid, phenol, aromatic nitrate, and combinations thereof.

3. The polymeric dispersant of claim 1 , wherein the base group is selected from a member of the group consisting of an aromatic amine, an aliphatic amine, pyridine, imidazole, benzimidazole, histidine, guanidine, a phosphazene base, an ammonium base, a phosphonium base, an onium base, and combinations thereof.

4. The polymeric dispersant of claim 1 , wherein the steric hydrophilic group comprises a member selected from the group consisting of polyethylene glycol, polypropylene glycol, and combinations thereof.

5. The polymeric dispersant of claim 1 , wherein the steric hydrophilic group comprises polyethylene glycol having a weight average molecular weight of from about 500 to about 20,000.

6. The polymeric dispersant of claim 1 , wherein the copolymer is of the structure:

wherein m 1 is an integer of from 1 to about 400;

wherein m 2 is an integer of from 0 to about 800;

wherein m 3 is an integer of from 1 to about 150;

wherein m 4 is an integer of from 1 to about 400;

wherein m 5 is an integer of from 1 to about 600;

wherein L 1 through L 5 are optional linking groups;

wherein L 1 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 2 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 3 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 4 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 5 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein R 1 is —(CH 2 ) 3-39 CH 3 ;

wherein R 2 is an aromatic group having from 6 to about 40 carbon atoms;

wherein R 3 is —(CH 2 CH 2 O) m (CH 2 CHCH 3 O) n R, wherein m is about 10 to about 450, n is about 0 to about 80, and R is H or CH 3 ;

wherein R 4 is a base group selected from a member of the group consisting of an amine, a pyridine, an imidazole, a benzimidazole, a histidine, a guanidine, a phosphazene base, an ammonium base, a phosphonium base, and an onium base;

wherein R 5 is an acid group selected from a member of the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, phenol, and aromatic nitrate; and

wherein R 1 ′, R 2 ′, R 3 ′, and R 4 ′ are each independently selected from a member of the group consisting of H, an alkyl group having from 1 to about 5 carbon atoms, and an aromatic group having from 6 to about 30 carbon atoms, and R 5 ′ is selected from a member of the group consisting of H, an alkyl group having from 1 to about 5 carbon atoms, an aromatic group having from 6 to about 30 carbon atoms, an acid group selected from a member of the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, phenol, and aromatic nitrate, and combinations thereof.

7. The polymeric dispersant of claim 1 , wherein the equations

0.05

<

m

1

(

M

R

1

+

M

R

1

′

)

+

m

2

(

M

R

2

+

M

R

2

′

)

∑

1

5

m

i

(

M

R

i

+

M

R

i

′

)

<

0.8

⁢

and

⁢

m

4

⁢

M

R

4

m

3

⁢

M

R

3

<

10

are used to define the dispersant components;

wherein M R1 is the molecular weight of the R 1 group;

wherein M R1 ′ is the molecular weight of the R 1 ′ group;

wherein M R2 is the molecular weight of the R 2 group;

wherein M R2 ′ is the molecular weight of the R 2 ′ group;

wherein M Ri is the molecular weight of the R i group;

wherein M Ri ′ is the molecular weight of the R i ′ group;

wherein i is 1 through 5 (that is R i =R 1 , R 2 , R 3 , R 4 , R 5 );

wherein m 1 is an integer of from 1 to about 400; m 2 is an integer of from 0 to about 800; m 3 is an integer of from 1 to about 150; m 4 is an integer of from 1 to about 400; and wherein m 5 is an integer of from 1 to about 600.

8. The polymeric dispersant of claim 1 , wherein the polymeric dispersant is free of alkyl phenol ethoxylates.

9. A self-crosslinked polymeric dispersant comprising:

a copolymer comprising:

an acid group;

a base group;

a hydrophobic group; and

a steric hydrophilic group comprising a member selected from the group consisting of polyethylene glycol, polypropylene glycol, and combinations thereof.

10. A self-crosslinked polymeric dispersant comprising:

a copolymer comprising:

an acid group;

a base group;

a hydrophobic group; and

a steric hydrophilic group;

wherein the copolymer is of the structure:

wherein m 1 is an integer of from 1 to about 400;

wherein m 2 is an integer of from 0 to about 800;

wherein m 3 is an integer of from 1 to about 150;

wherein m 4 is an integer of from 1 to about 400;

wherein m 5 is an integer of from 1 to about 600;

wherein L 1 through L 5 are optional linking groups;

wherein L 1 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 2 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 3 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 4 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein L 5 is a linking group selected from a member of the group consisting of ether, urea, epoxy, ester, amide, oxygen, sulfur, carbon, and an alkyl chain of from about 1 to about 6 carbon atoms;

wherein R 1 is —(CH 2 ) 3-39 CH 3 ;

wherein R 2 is an aromatic group having from 6 to about 40 carbon atoms;

wherein R 3 is —(CH 2 CH 2 O) m (CH 2 CHCH 3 O)R, wherein m is about 10 to about 450, n is about 0 to about 80, and R is H or CH 3 ;

wherein R 4 is a base group selected from a member of the group consisting of an amine, a pyridine, an imidazole, a benzimidazole, a histidine, a guanidine, a phosphazene base, an ammonium base, a phosphonium base, and an onium base;

wherein R 5 is an acid group selected from a member of the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, phenol, and aromatic nitrate; and

wherein R 1 ′, R 2 ′, R 3 ′, and R 4 ′ are each independently selected from a member of the group consisting of H, an alkyl group having from 1 to about 5 carbon atoms, and an aromatic group having from 6 to about 30 carbon atoms, and R 5 ′ is selected from a member of the group consisting of H, an alkyl group having from 1 to about 5 carbon atoms, an aromatic group having from 6 to about 30 carbon atoms, an acid group selected from a member of the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, phenol, and aromatic nitrate, and combinations thereof.

11. A self-crosslinked polymeric dispersant comprising:

a copolymer comprising:

an acid group;

a base group;

a hydrophobic group; and

a steric hydrophilic group;

wherein the equations

0.05

<

m

1

(

M

R

1

+

M

R

1

′

)

+

m

2

(

M

R

2

+

M

R

2

′

)

∑

1

5

m

i

(

M

R

i

+

M

R

i

′

)

<

0.8

⁢

and

⁢

m

4

⁢

M

R

4

m

3

⁢

M

R

3

<

10

are used to define the dispersant components;

wherein M R1 is the molecular weight of the R 1 group;

wherein M R1 ′ is the molecular weight of the R 1 ′ group;

wherein M R2 is the molecular weight of the R 2 group;

wherein M R2 ′ is the molecular weight of the R 2 ′ group;

wherein M Ri is the molecular weight of the R i group;

wherein M Ri ′ is the molecular weight of the R i ′ group;

wherein i is 1 through 5 (that is R i =R 1 , R 2 , R 3 , R 4 , R 5 );

wherein m 1 is an integer of from 1 to about 400; m 2 is an integer of from 0 to about 800; m 3 is an integer of from 1 to about 150; m 4 is an integer of from 1 to about 400; and wherein m 5 is an integer of from 1 to about 600.

Assignments (7)