Polyalkyleneimine-based polymer as dispersants

1 . A polymer having

a) from 0.5 to 25 weight % of a polyalkyleneimine backbone based on the total weight of the polymer;

b) from 0.5 to 25 weight % of at least one aromatic moiety P.1, which is bound to a nitrogen atom of the polyalkyleneimine backbone via a carboxamide or carboximide group, based on the total weight of the polymer;

c) from 1 to 50 weight % of at least one polyester moiety P.2, which is bound to a nitrogen atom of the polyalkyleneimine backbone via a carboxamide, based on the total weight of the polymer; and

d) from 30 to 90 weight % of at least one aliphatic polyether moiety P.3, which is bound to a nitrogen atom of the polyalkyleneimine backbone via a direct bond or via a linker, based on the total weight of the polymer,

wherein the at least one aromatic moiety P.1 is selected from the moieties of the formulae (P.1′) and (P.1″),

wherein

#indicates the point of attachment of the aromatic moiety P.1 to a nitrogen atom of the polyalkyleneimine backbone;

Ar is selected from the group consisting of phenyl and naphthyl, wherein phenyl and naphthyl, each independently, are unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals, which are selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C(═O)—OH, C(═O)—NH 2 , NH 2 , NO 2 , NH—C(═O)—H, NH—C 1 -C 4 -alkyl and NH—C(═O)—C 1 -C 4 -alkyl; and

Ar′ is selected from the group consisting of 1,2-phenylene, 1,2-, 2,3-, or 1,8-naphthylene, wherein phenylene and naphthylene, each independently, are unsubstituted or substituted by 1, 2, 3, 4 or 5 radicals, which are selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C(═O)—OH, C(═O)—NH 2 , NH 2 , NO 2 , NH—C(═O)H, NH—C 1 -C 4 -alkyl, and NH—C(═O)—C 1 -C 4 -alkyl,

wherein the polyester moiety P.2 is a radical of the formula (P.2a)

wherein,

#indicates the point of attachment to a nitrogen atom of the polyalkyleneimine backbone;

T 1 is hydrogen or R 1 —C(═O)— wherein R 1 is C 1 -C 24 alkyl;

A 1 and A 2 are each independently selected from C 2 -C 12 alkylene;

m is an integer from 0 to 100;

n is an integer from 0 to 100; and

m+n is an integer from 2 to 100.

2 . The polymer according to claim 1 , wherein the polyalkyleneimine backbone has a weight average molecular weight in the range of from 100 g/mol to 20,000 g/mol, as determined according to DIN 55672-1.

3 . The polymer according to claim 1 , wherein the polyalkyleneimine backbone is a polyethyleneimine backbone.

4 . The polymer according to claim 1 , wherein the at least one aromatic moiety P.1 is selected from the group consisting of moieties of formulae (P.1a), (P.1b), (P.1c), (P.1d), and (P.1e),

wherein

#indicates the point of attachment of the aromatic moiety to a nitrogen atom of the polyalkyleneimine backbone;

R′ is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, —C(═O)—H and —C(═O)—C 1 -C 4 -alkyl;

k is 0, 1, 2, 3 or 4; and

R is, identical or different, a radical selected from the group consisting of halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C(═O)—OH, C(═O)—NH 2 , NH 2 , NO 2 , NH—C(═O)—H, NH—C 1 -C 4 -alkyl, and NH—C(═O)—C 1 -C 4 -alkyl.

5 . The polymer according to claim 1 , wherein the at least one aliphatic polyether moiety P.3 is selected from (P.3a) and (P.3b),

wherein,

#indicates the point of attachment to a nitrogen atom of the polyalkyleneimine backbone;

L is a linker;

R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 2 -alkyl;

p is an integer from 0 to 200;

q is an integer from 0 to 200;

p+q is an integer from 2 to 200; and

T 2 is hydrogen, C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C(═O)—C 2 -C 20 -alkenyl or C(═O)—C 1 -C 20 -alkyl, wherein C 2 -C 20 -alkenyl has 1, 2, 3 or 4 olefinic C═C-double bonds, and wherein 1, 2, 3, or 4 non-adjacent CH 2 groups of C 1 -C 20 -alkyl may be replaced by O.

6 . The polymer according to claim 5 , wherein the linker L is at least one selected from the group consisting of (L.1), (L.2), (L.3) and (L.4),

wherein

#indicates the point of attachment to a nitrogen atom of the polyalkyleneimine backbone;

* indicates the point of attachment to the polyether moiety P.3;

R 5 is H or CH 3 ;

Q is a direct bond or a divalent moiety selected from —O—, —N(H)—, and —S—;

Y is O or NH;

Z is selected from the group consisting of C 1 -C 24 alkyl, C 4 -C 10 cycloalkyl, C 6 -C 18 aryl, and C 7 -C 20 arylalkyl;

A 1 and A 2 are each independently selected from C 2 -C 12 alkylene;

m is an integer from 0 to 100;

n is an integer from 0 to 100; and

m+n is an integer from 2 to 100.

7 . The polymer according to claim 1 , wherein the polymer has an acid number in the range of 0 to 15 mg KOH/g, as determined according to DIN 53402:1990-09.

8 . A process for preparing the polymer according to claim 1 , comprising the following steps,

i. reacting a polyalkyleneimine with an aromatic carboxylic acid, an aromatic carboxylic anhydride or with an amide or imide forming derivative of an aromatic carboxylic acid, in such an amount that theoretically at most 90%, based on the total amount of primary and secondary nitrogen atoms of the polyalkyleneimine can be consumed;

ii. reacting the product of step (i) with a hydroxycarboxylic acid, a lactone monomer or a polyester moiety having a terminal carboxyl group obtainable from the lactone monomer; and

iii. reacting the product of step (ii) with an alkylene oxide or a polyether moiety having a terminal radical selected from an acrylate, an isocyanato, and a carboxylate.

9 . A process for preparing the polymer according to claim 1 , comprising the following steps,

i. reacting a polyalkyleneimine with an aromatic carboxylic acid, an aromatic carboxylic anhydride or with an amide or imide forming derivative of an aromatic carboxylic acid, in such an amount that theoretically at most 90%, based on the total amount of primary and secondary nitrogen atoms of the polyalkyleneimine can be consumed; and

ii. reacting the product of step (i) with

a hydroxycarboxylic acid, a lactone monomer or a polyester moiety having a terminal carboxyl group obtainable from the lactone monomer; and

an alkylene oxide or a polyether moiety having a terminal radical selected from an acrylate, an isocyanato, and a carboxylate.

10 . A process for preparing the polymer according to claim 1 , comprising reacting a polyalkyleneimine with

an aromatic carboxylic acid, an aromatic carboxylic anhydride or with an amide or imide forming derivative of an aromatic carboxylic acid;

a hydroxycarboxylic acid, a lactone monomer or a polyester moiety having a terminal carboxyl group obtainable from the lactone monomer; and

an alkylene oxide or a polyether moiety having a terminal radical selected from an acrylate, an isocyanato, and a carboxylate.

11 . A process for preparing the polymer according to claim 1 , comprising the following steps,

i. reacting a polyalkyleneimine with

an aromatic carboxylic acid, an aromatic carboxylic anhydride or with an amide or imide forming derivative of an aromatic carboxylic acid; and

a hydroxycarboxylic acid, a lactone monomer or a polyester moiety having a terminal carboxyl group obtainable from the lactone monomer; and

ii. reacting the product of step (i) with an alkylene oxide or a polyether moiety having a terminal radical selected from an acrylate, an isocyanato, and a carboxylate.

12 . A liquid composition in the form of a dispersion comprising a particulate solid material selected from the group consisting of pigments and fillers, a liquid diluent, wherein the particulate solid material is dispersed in the liquid diluent, further comprising a polymer according to claim 1 .

13 . The polymer according to claim 1 , wherein T 1 is CH 3 (CH 2 ) 10 —.

14 . The polymer according to claim 13 , wherein Ar is naphthyl and Ar′ is 1,2-, 2,3-, or 1,8-naphthylene.