Polyaspartic ester compositions, and methods of making and using same

Patent metadata

Field	Value
Publication number	US-10717702-B2
Application number	US-201816489556-A
Country	US
Kind code	B2
Filing date	Mar 2, 2018
Priority date	Mar 3, 2017
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

Methods of preparing a polyaspartic ester composition comprise reacting a primary diamine reactant composition with a diester reactant composition under conditions to prepare a polyaspartic ester composition having a primary amine value of less than 35 mg KOH/g wherein, at the time of the reaction, the combined water content of the primary diamine reactant composition and the diester reactant composition is less than 300 ppm. Compositions and methods of use of the compositions are also described.

First claim

What is claimed is:

1. A method of preparing a polyaspartic ester composition comprising
a) providing a primary diamine reactant composition;
b) providing a diester reactant composition comprising a diester selected from the group consisting of diesters of maleic acid, fumaric acid or combinations thereof, and
c) reacting the primary diamine reactant composition with the diester reactant composition under conditions to prepare a polyaspartic ester composition having a primary amine value of less than 35 mg KOH/g;
wherein, at the time of the reaction, the combined water content of the primary diamine reactant composition and the diester reactant composition is less than 300 ppm.

2. A method of preparing a polyaspartic ester composition comprising
a) providing primary diamine reactant composition comprising at least one diamine compound;
b) providing a diester reactant composition comprising at least one diester compound selected from the group consisting of diesters of maleic acid, fumaric acid or combinations thereof; and
c) reacting the primary diamine reactant composition with the diester reactant composition under conditions to prepare a polyaspartic ester composition having a primary amine value of less than 35 mg KOH/g;
wherein, at the time of the reaction, the combined water content of the primary diamine reactant composition and the diester reactant composition is less than 300 ppm; and
wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Gel Time of from about 40 minutes to about 100 minutes.

3. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Gel Time of from about 45 minutes to about 90 minutes, or from about 55 minutes to about 80 minutes, or from about 60 minutes to about 75 minutes.

4. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Shore D Hardness at 24 hours of greater than 60.

5. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Shore D hardness at 24 hours of from 70 to 100.

6. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a 15 second Small Cracking Mandrel Bend value of greater than 10.

7. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Chemical Resistance rating at 250 rubs of at least 4 for methyl ethyl ketone, or has a Chemical Resistance rating at 250 rubs of at least 5 for methyl ethyl ketone.

8. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Chemical Resistance rating at 250 rubs of at least 4 for Skydrol, or has a Chemical Resistance rating at 250 rubs of at least 5 for Skydrol.

9. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has an Impact Resistance Test Failure of greater than 30 lbs.

10. The method of claim 2 , wherein the diamine compounds and the diester compounds of the primary diamine reactant composition and the diester reactant composition are selected such that the polyaspartic ester composition, when reacted with hexamethylene diisocyanate trimer, has a Buchholz Hardness Mar Resistance of greater than 85.

11. The method of claim 1 , wherein the primary diamine reactant composition comprises an amine that is 2,4′-methylene bis cyclohexylamine.

12. The method of claim 11 , wherein from about 2 percent to about 20 percent of the amine in the primary diamine reactant composition is 2,4′-methylene bis cyclohexylamine.

13. The method of claim 1 , wherein the primary diamine reactant composition comprises an amine that is 4,4′-methylene bis cyclohexylamine.

14. The method of claim 13 , wherein at least about 80 percent of the amine in the primary diamine reactant composition is 4,4′-methylene bis cyclohexylamine.

15. The method of claim 13 , wherein at least about 95 percent of the amine in the primary diamine reactant composition is 4,4′-methylene bis cyclohexylamine.

16. The method of claim 1 , wherein the diester is selected from diesters of maleic acid.

17. The method of claim 1 , wherein the diester is selected from C1-4 alkyl diesters of maleic acid, or mixtures thereof.

18. The method of claim 1 , wherein the diester is diethyl maleate.

19. A polyaspartic ester composition made by the method of claim 1 .

Assignees

• Cargill Inc

Inventors

• Karl Andrew M
• Kurth Todd L

Classifications

• C07C227/06 Primary

  by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid · CPC title

• C07C201/00

  Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C227/18

  by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title