Amine dispersants

Patent metadata

Field	Value
Publication number	US-12516202-B2
Application number	US-202017604131-A
Country	US
Kind code	B2
Filing date	Apr 15, 2020
Priority date	Apr 18, 2019
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

The presently claimed invention relates to a dispersant containing oxyalkylenecarbonyl units and a process for its preparation. The presently claimed invention is also directed to the use of the dispersant in a coating composition or an ink composition.

First claim

The invention claimed is:

1 . A dispersant of formula (I),
T −( A ) m −L −Z  formula (I),
wherein T is hydrogen or R 1 —C(═O)—, R 1 is a substituted or unsubstituted, linear or branched C 1 -C 24 alkyl; wherein (A) m is (A 1 ) M1 (A 2 ) M2 , wherein A 1 and A 2 are different from each other and selected from the group consisting of —O—(CH 2 ) 5 —C(═O)—, —O—(CH 2 ) 4 —C(═O)— and —O—(CH 2 ) 3 —C(═O)—; and M1 and M2 are, identical or different, an integer in the range from 1 to 40, and the ratio of M1 and M2 is in the range from 10:1 to 1:10; L represents a group selected from the group consisting of —O— and —NH—; Z is a nitrogen containing group selected from the group consisting of Z 1 , Z 2 , and Z 3 and the dispersant has an amine number from 10 to 200 mg KOH/g, as determined according to DIN 53176:2002-11; wherein Z 1 is R 11 R 12 N—R 13 —, Z 2 is Y—R 14 —, and Z 3 is Y—CH 2 —CH 2 —C(═O)—OR 14 — R 11 and R 12 are independently selected from hydrogen and substituted or unsubstituted, linear or branched C 1 -C 12 alkyl which can be the same or different, or R 11 and R 12 together with the nitrogen to which they are attached form a 3- to 12-membered ring comprising 0 to 3 heteroatoms, R 13 is a substituted or unsubstituted, linear or branched C 1 -C 12 alkylene; Y is a 5- or 6-membered N-containing heterocycle which comprises 1 or 2 nitrogen atoms and which can additionally comprise an oxygen atom, R 14 is a substituted or unsubstituted, linear or branched C 1 -C 12 alkylene; or Z is a quaternary ammonium salt derivable from the nitrogen containing group selected from the group consisting of Z 1 , Z 2 , and Z 3 and the dispersant has an amine number from 1 to 20 mg KOH/g, as determined according to DIN 53176:2002-11; wherein the quaternary nitrogen is attached to R 15 and an anion X—, R 15 is selected from the group consisting of hydrogen, a substituted or unsubstituted, linear or branched C 1 -C 24 alkyl, a substituted or unsubstituted C 4 -C 10 cycloalkyl, a substituted or unsubstituted C 6 -C 18 aryl, and substituted or unsubstituted, branched or unbranched C 7 -C 18 arylalkyl; wherein the C 1 -C 24 alkyl is optionally interrupted by —O— and/or is optionally substituted by a group selected from —OH and —O—C 1 -C 10 alkyl; and X − is selected from the group consisting of Cl, Br, I, acetate and benzoate.

2 . The dispersant according to claim 1 , wherein R 1 selected from the group consisting of CH 3 (CH 2 ) 3 —, CH 3 (CH 2 ) 10 —, and CH 3 (CH 2 ) 16 —.

3 . The dispersant according to claim 1 , wherein m is an integer in the range from 3 to 20.

4 . The dispersant according to claim 1 , wherein (A) m is (—O—(CH 2 ) 5 —C(═O)—) M1 (—O—(CH 2 ) 4 —C(═O)—) M2 , wherein M1 and M2 are, identical or different, an integer in the range from 1 to 40, and the ratio of M1 and M2 is in the range from 10:1 to 1:10.

5 . The dispersant according to claim 1 , wherein R 11 and R 12 are independently unsubstituted, linear or branched C 1 -C 8 alkyl, and R 13 is unsubstituted, linear or branched C 1 -C 8 alkylene.

6 . The dispersant according to claim 1 , wherein R 11 is methyl, R 12 is methyl and R 13 is —CH 2 CH 2 CH 2 —.

7 . The dispersant according to claim 1 , wherein Y is selected from the group consisting of imidazolyl, morpholinyl and piperidinyl.

8 . The dispersant according to claim 1 , wherein R 14 is selected from the group consisting of —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — and —CH 2 CH 2 CH 2 CH 2 —.

9 . The dispersant according to claim 1 , wherein R 15 is selected from the group consisting of —CH 2 CH(OH) CH 2 —O—CH 2 CH(C 2 H 5 ) CH 2 CH 2 CH 2 CH 3 , —CH 2 -phenyl and —CH 2 CH 2 CH 2 -phenyl, wherein phenyl is unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of chloride, bromide, hydroxy, NO 2 and methoxy.

10 . A process for preparing a dispersant according to claim 1 comprising
i. mixing a compound of formula R 11 R 12 N—R 13 —NH 2 with a lactone monomer of formula (II),

 or a polyester homopolymer or copolymer obtainable from the lactone monomer of formula (II) to obtain a reaction mixture, wherein R 2 , R 11 , R 12 and R 13 are as defined as in claim 1 ;
ii. heating the reaction mixture as obtained in step i. at a temperature in the range of 70 to 150° C. to obtain a homogeneous mixture; and
iii. heating the homogeneous mixture as obtained in step ii. at a temperature in the range of 100 to 300° C. to obtain the dispersant of formula (I).

11 . A process for preparing the dispersant according to claim 1 comprising
a. heating a hydroxyalkyl acrylate of formula CH 2 ═CH—C(═O)—O—R 14 —OH with a 5- or 6-membered N-containing heterocycle of formula YH at a temperature in the range of 30 to 100° C. to obtain a resultant mixture, wherein Y and R 14 is defined as in claim 1 ; and
b. adding the lactone monomer of formula (II)

 wherein R 2 is defined as in claim 1 ,
 or a polyester homopolymer or copolymer obtainable from the lactone monomer of formula (II) to the resultant mixture as obtained in step a. to obtain a reaction mixture;
c. heating the reaction mixture as obtained in step b. at a temperature in the range of 70 to 150° C. to obtain a homogeneous mixture; and
d. heating the homogeneous mixture as obtained in step c. at a temperature in the range of 100 to 300° C. to obtain the dispersant of formula (I).

12 . The process according to claim 10 further comprising a step of quaternizing the dispersant obtained in step (iii) or step (d) by heating a mixture comprising the dispersant and an alkylating agent at a temperature in the range of 50 to 150° C.

13 . A liquid composition in the form of a dispersion comprising the dispersant according to claim 1 , a particulate solid material selected from the group consisting of pigments and fillers, and a liquid diluent.

14 . A method comprising utilizing the dispersant according to claim 1 as a component of a coating composition or an ink composition.

Assignees

• Basf Se

Inventors

• Kou Huiguang
• Onclin Steffen
• Gernandt Andreas
• Willenbacher Johannes Hermann
• Auschra Clemens

Classifications

• C09K23/16

  Amines or polyamines · CPC title

• C09K23/42

  Ethers, e.g. polyglycol ethers of alcohols or phenols · CPC title

• C09D11/326

  characterised by the pigment dispersant · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08G63/685

  containing nitrogen · CPC title