Multi-amine polyester dispersant made via an anhydride intermediate
The present invention relates to a dispersant derived from anhydride functionalized polyester derived from carboxylic acid functionalized polyester. The anhydride functionalized polyester is then reacted with a multi-amine species forming amide and salt bonds. The technology allows lower reaction temperatures when the multi-amine species is present. The lower reaction temperature allows the use of a broader selection of polyester repeat units.
1. A dispersant of the following structure:
wherein:
MA is a multi-amine species;
PE1 is a polyester chain of number average molecular weight between 500 and 4,000 g/mole attached to the multi amine species (MA) via an amide bond;
wherein a carbonyl group is formed from a terminal group of PE1 and a nitrogen from the MA;
PE2 is a polyester chain of number average molecular weight between 500 and 4,000 g/mole attached to the multi amine species (MA) via a salt linkage;
wherein a deprotonated carboxylic acid group is formed from a terminal group of PE2 and a protonated nitrogen from the MA;
A1 is the residue of a C 2-5 carboxylic acid attached to the MA via an amide bond, wherein a carbonyl group is formed from a terminal group of A1 and a nitrogen from the MA;
A2 is the residue of a C 2-5 carboxylic acid attached to the MA via a salt linkage, wherein a deprotonated carboxylic acid group is formed from a terminal group of A2 and a protonated nitrogen from the MA;
the relative molar ratios of amide bonds represented by p and p′ to salt linkages represented by q and q′ are between 5:95 and 50:50;
p+p′ can never be greater than q+q′;
p is 1 or greater than 1, and p′ is 1 or greater than 1;
q is 1 or greater than 1, and q′ is 1 or greater than 1; and
p+p′+q+q′ is between 4 and 2000.
2. The dispersant composition of claim 1 , wherein MA is selected from the group consisting of a non-polymeric alkyl amine with 3 or more nitrogen atoms, polyvinylamine, or polyallylamine.
3. The dispersant composition of claim 1 , wherein MA comprises polyethyleneimine or modified polyethyleneimine.
4. The dispersant of claim 1 , wherein p+q is on average from 4 to 36.
5. The dispersant composition of claim 1 , wherein said PE1 is of the formula R 1 —[OR 3 —C(═O)] n — and said PE2 is of the formula R 1 —[OR 3 —C(═O)] n —O −
wherein:
R 1 is H— or R 2 C(═O)—;
R 2 is a branched or linear, saturated or unsaturated hydrocarbon chain containing between 1 and 25 carbons atoms;
R 3 is a branched or linear, saturated or unsaturated hydrocarbon chain containing between 1 and 25 carbons atoms or —R 4 —OC(═O)R 5 —;
R 4 is a branched or linear, saturated or unsaturated hydrocarbon chain containing between 2 and 30 carbons atoms;
R 5 is a branched or linear, saturated or unsaturated hydrocarbon chain containing between 1 and 20 carbons atoms; and
n is between 3 and 43.
6. The dispersant composition of claim 5 , wherein at least 10 mole % of the R 3 units are linear or branched alkyl groups of 1 to 5 carbon atoms.
7. The dispersant composition of claim 5 , wherein at least 5 mole % of the R 3 units are linear or branched alkyl groups of 4 and/or 5 carbon atoms.
8. The dispersant composition of claim 5 , wherein at least 10 mole % of the R 3 units are linear or branched alkyl groups of 6 to 17 carbon atoms.
9. The dispersant composition of claim 5 , wherein at least 5 mole % of the R 3 units are linear or branched alkyl groups of 1 or 2 carbon atoms.
10. The dispersant of claim 1 , further comprising an amine group of said multi-amine species being a reaction product of: i) one more primary or secondary amines groups of said multi-amine species with (a) an isocyanate, lactone, epoxy, anhydride, cyclic carbonate, (meth)acrylate via Michael addition reaction, or a polymeric species having a group that reacts with a primary or secondary amine to form a salt or covalent bond; (b) an oxidizing species that could convert the amine group to a nitric oxide; or (c) a salification agent; or ii) a tertiary amine group reacted with a quaternization agent to form a quaternized amine group.
11. A coating, paint, ink or plastic comprising the dispersant of claim 1 .
12. The dispersant composition of claim 1 , wherein at least one of PE1 or PE2 independently comprises from 1 to 50 mole % of at least one di-hydroxy compound.
13. The dispersant composition of claim 12 , wherein the at least one di-hydroxy compound comprises at least one of 2,2-bis(hydroxymethyl)butyric acid or 2,2-bis(hydroxymethyl)propionic acid.
14. The dispersant composition of claim 5 , wherein R 4 is a branched or linear, saturated or unsaturated hydrocarbon chain containing between 2 and 30 carbons atoms, which contains 1 or more ether linkages.