Polyamidoamine dispersants

Patent metadata

Field	Value
Publication number	US-12441897-B2
Application number	US-202117382008-A
Country	US
Kind code	B2
Filing date	Jul 21, 2021
Priority date	Jul 23, 2020
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

A pigment dispersant can be obtained by reacting amine-rich moieties C with at least one polymer P having one or more amine reactive groups. The amine-rich moieties C have an amine density of at least 600 mg KOH/g and are obtainable from repetitive self-reaction of at least one type of substance B and/or from cross-reaction of at least one B with at least one substance A. B is an adduct of at least one substance A and at least one linker D. The amine-reactive functionality in B and D are reacted with reactive amines in B and/or A; and if B has only one amine reactive group, then additional D and/or mixture of B and A is reacted to a previously formed C, where such an additional reaction of D and/or mixture of B and A to a formed C is repeated for 1 to 10 times.

First claim

The invention claimed is:

1. A pigment dispersant obtained by reacting amine-rich moieties C with at least one polymer P, said polymer P having one or more amine reactive groups,
wherein said amine-rich moieties C have an amine density of at least 600 mg KOH/g and said amine-rich moieties C are obtainable from repetitive self-reaction of at least one type of substance B and from cross-reaction of at least one B with at least one substance A, wherein the reaction temperature should remain below 230° C.,
wherein the at least one B is an adduct of the at least one substance A and at least one linker D, and B contains 1-15 amine-reactive groups and 4-15 in total number of primary, secondary, tertiary and quaternary amines,
wherein the at least one substance A is a branched and/or linear aliphatic and/or cycloaliphatic or aromatic polyamine containing 4-15 total number of primary, secondary, tertiary and quaternary amines,
wherein the at least one linker D is an acrylate, a maleate/fumarate mono-ester or a maleate/fumarate di-ester containing 1-15 amine-reactive groups, or a mixture thereof;
wherein the amine-reactive groups in B and D are reacted with reactive amines in B and/or A, and if B has only one amine reactive group then additional D and/or mixture of B and A is reacted to a previously formed C,
and wherein such additional reaction of D and/or mixture of B and A to a formed C is repeated for 1 to 10 times.

2. The pigment dispersant according to claim 1 , wherein the amine-rich moieties C have an amine density of 600 mg KOH/g to 1,000 mg KOH/g.

3. The pigment dispersant according to claim 2 , wherein the amine-rich moieties C have an amine density of 700 mg KOH/g to 1,000 mg KOH/g.

4. The pigment dispersant according to claim 1 , wherein the at least one polymer P is a polyester, a polyether, a polyesterether, a poly(meth)acrylate, or a mixture thereof.

5. The pigment dispersant according to claim 1 , wherein the at least one polymer P is a polylactone or a polycaprolactone.

6. The pigment dispersant according to claim 1 , wherein the at least one substance B has 2 to 15 amine-reactive groups, and
wherein the additional D and/or mixture of B and A is reacted to a previously formed C, wherein such additional reaction of D and/or mixture of B and A to a formed C is repeated for 1 to 10 times.

7. The pigment dispersant according to claim 1 , wherein the at least one substance A is at least one selected from the group consisting of triethylenetetramine, tetraethylenepentamine, and pentaethylenehexamine.

8. The pigment dispersant according to claim 1 , wherein the reaction product obtained by reacting the amine-rich moieties C with the at least one polymer P is further reacted with at least one substance Q selected from the group consisting of peroxides, alkyl halide, carboxylic acid, carboxylic ester, ketone, aldehyde, epoxide, isocyanate, uretdiones, carbodiimide, Michael acceptors, and anhydride.

9. The pigment dispersant according to claim 8 , wherein the at least one substance Q is an anhydride.

10. A process for producing a pigment dispersant according to claim 1 , the process comprising:
a) repetitive self-reacting at least one type of substance B and/or cross-reacting at least one B with at least one substance A to produce amine-rich moieties C having an amine density of at least 600 mg KOH/g,
wherein B is an adduct of the at least one substance A and at least one linker D, and B contains 1-15 amine-reactive groups and 4-15 in total number of primary, secondary, tertiary and quaternary amines,
the at least one substance A is a branched and/or linear aliphatic and/or cycloaliphatic or aromatic polyamine containing 4-15 total number of primary, secondary, tertiary and quaternary amines, and
the linker D is an acrylate, a maleate/fumarate mono-ester or a maleate/fumarate di-ester containing 1-15 amine-reactive groups, or a mixture thereof; and
wherein the amine-reactive groups in B and D are reacted with reactive amines in B and/or A, and if B has only one amine reactive group then additional D and/or mixture of B and A is reacted to a previously formed C, wherein such additional reaction of D and/or mixture of B and A to a formed C is repeated for 1 to 10 times; and
b) reacting the amine-rich moieties C with at least one polymer P, said polymer P having one or more amine reactive groups.

11. The process for producing a pigment dispersant according to claim 10 , wherein the amine-rich moieties C have an amine density of 600 mg KOH/g to 1,000 mg KOH/g.

12. The process for producing a pigment dispersant according to claim 10 , wherein the at least one substance B has 2 to 15 amine-reactive groups, and
wherein the additional D and/or mixture of B and A is reacted to a previously formed C, wherein such additional reaction of D and/or mixture of B and A to a formed C is repeated for 1 to 10 times.

13. The process for producing a pigment dispersant according to claim 10 , wherein the at least one substance A is at least one selected from the group consisting of triethylenetetramine, tetraethylenepentamine, and pentaethylenehexamine.

14. The process for producing a pigment dispersant according to claim 10 , wherein the reaction product of the amine-rich moieties C and the at least one polymer P is reacted with a substance Q selected from the group consisting of peroxides, alkyl halide, carboxylic acid, carboxylic ester, ketone, aldehyde, epoxide, isocyanate, uretdiones, carbodiimide, Michael acceptors, and anhydride.

15. The pigment dispersant according to claim 1 , wherein said amine-rich moieties C have an amine density of at least 600 mg KOH/g and said amine-rich moieties C are obtained from repetitive self-reaction of at least one type of substance B and from cross-reaction of at least one B with at least one substance A.

16. The pigment dispersant according to claim 1 , which has a color strength of greater than 115.

17. The pigment dispersant according to claim 1 , wherein the at least one substance A comprises tetraethylenepentamine (TEPA) and the at least one linker D comprises butyl acrylate, diethyl maleate, or monoethyl maleate.

18. The pigment dispersant according to claim 1 , wherein after formation of the C, additional reaction of D and/or mixture of B and A to the formed C is repeated for 1 to 10 times.

19. The pigment dispersant according to claim 1 , wherein initially the at least one B is formed as an adduct of the at least one substance A and at least one linker D, and then after formation of the at least one B, C is formed by the repetitive self-reaction and the cross-reaction.

20. The pigment dispersant according to claim 19 , wherein polyamine A is added after the formation of the at least one B.

Assignees

• Evonik Operations Gmbh

Inventors

• Sze Ming Choon
• Shinde Sunil
• Tang Haihua
• Liu Kerh Li
• Dürr Christoph

Classifications

• C09D17/002

  in organic medium (C09D17/003, C09D17/004 take precedence) · CPC title

• C08K5/19

  Quaternary ammonium compounds · CPC title

• C08G73/028 Primary

  Polyamidoamines · CPC title

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title

• C08F222/06

  Maleic anhydride · CPC title