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 method of preparing a polyester containing dispersant by reacting a pre-made polyester with a multi-amine species comprising the steps of:
a) preparing a polyester having a single carboxylic acid terminal group and 3 to 43 ester repeat units on average in each chain;
b) converting at least 10 mole % of carboxylic acid terminal groups on said polyester to anhydride functionality by reacting with a dehydrating agent which is an anhydride of two carboxylic acid molecules of 2 to 5 carbon atoms; and
c) reacting the reaction product of step b) with a multi-amine species at a temperature of 100° C. or less to create a multi-amine with pendant polyester chains thereon.
2. The method of claim 1 , wherein said step b) includes reacting said polyester with dehydrating agent selected from the group of acetic anhydride, propionic anhydride, and butyric anhydride at a temperature between 100° C. and 199° C.
3. The method of claim 1 , wherein said polyester with a single carboxylic acid terminal group is of the formula
R 1 —[OR 3 —C(═O)] n —OH
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.
4. The method of claim 3 , wherein at least 10 mole % of the R 3 units are linear or branched alkyl groups of 1 to 5 carbon atoms.
5. The method of claim 3 , wherein at least 5 mole % of the R 3 units are linear or branched alkyl groups of 4 and/or 5 carbon atoms.
6. The method of claim 3 , wherein at least 10 mole % of the R 3 units are linear or branched alkyl groups of 6 to 17 carbon atoms.
7. The method of claim 3 , wherein at least 5 mole % of the R 3 units are linear or branched alkyl groups of 1 or 2 carbon atoms.
8. The method of claim 3 , further comprising a step where i) one more primary or secondary amines groups of said multi-amine species or the dispersant containing a multi-amine species are reacted with (a) an isocyanate, lactone, epoxy, anhydride, cyclic carbonate, (meth)acrylate via Michael addition reaction, and/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; and/or (c) a salification agent; or ii) a tertiary amine group of said multi-amine species or the dispersant containing the multi-amine species is reacted with a quaternization agent to form a quaternized amine group.
9. A dispersant comprising the reaction product of the method of claim 3 .
10. A coating, paint, ink or plastic comprising the dispersant of claim 9 .
11. The method of claim 1 , wherein said polyester comprises from 1 to 50 mole % of at least one di-hydroxy compound.
12. The method of claim 11 , 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.
13. The method of claim 3 , 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.