IP Library Granted Patent US 9,944,821
Granted Patent B2
US 9,944,821 · App. 14/774,963 · Granted Apr 17, 2018

Polyaspartic coating compositions

Inventors: Edward P. Squiller (Bridgeville, PA); Terrell D. Wayt (Moundsville, WV); John Forsythe (Allison Park, PA); Kurt E. Best (Sewickley, PA); Ahren Olson (Aliquippa, PA); Alan Ekin (Coraopolis, PA)
Assignee: Covestro LLC
C09D175/02C08G18/3256C08G18/3821C08G18/792
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Quick Facts
Patent No.
US 9,944,821
App. No.
14/774,963
Granted
Apr 17, 2018
Kind
B2
Abstract

Two-component coating systems and compositions are disclosed. The coating compositions form crosslinked polyurea coatings and have relatively long pot life and relatively short dry time. The coating compositions include a polyisocyanate, a polyaspartic ester, and a polyetheraspartic ester.

Claims (51)

1. A two-component coating system for the production of polyurea coatings, the coating system comprising:

(A) a polyisocyanate;

(B1) a polyaspartic ester corresponding to the following formula:

wherein:

X represents an aliphatic residue; and

R 1 and R 2 represent ethyl residues; and

(B2) a polyetheraspartic ester corresponding to the following formula:

wherein:

n is an integer of 3;

m is independently an integer of 1 to 5;

Z′ represents a 1,1,1-tris(methyl)propyl residue;

R 1 and R 2 represent ethyl residues; and

R 3 represents isopropyl (1-methylethyl) residues.

2. The coating system of claim 1 , wherein the polyisocyanate comprises an isocyanurate trimer of 1,6-hexamethylene diisocyanate.

3. The coating system of claim 1 , wherein the polyisocyanate comprises an iminooxadiazine dione asymmetric trimer of 1,6-hexamethylene diisocyanate.

4. The coating system of claim 1 , wherein the polyisocyanate comprises a diisocyanate adduct of isophorone diisocyanate.

5. The coating system of claim 1 , wherein X is selected from the group consisting of a dicyclohexylmethane residue, a 3,3′-dimethyl-dicyclohexylmethane residue, and a 2-methyl-pentane residue.

6. The coating system of claim 1 , wherein the ratio of un-reacted isocyanate groups to amine groups is 1:1 to 1.5:1.

7. The coating system of claim 1 , further comprising an organic solvent.

8. The coating system of claim 1 , further comprising:

(B3) at least one of a polyaldimine and a polyketimine corresponding to the following formula:

wherein:

R 4 and R 5 independently represent hydrogen or a hydrocarbon group with up to 20 carbon atoms, or R 4 and R 5 form a 5-membered or 6-membered cycloaliphatic ring together with the carbon atom;

R 6 is a (p+1)-valent residue obtained by removing the primary amino groups from a corresponding polyamine, optionally containing oxygen; and

p is an integer from 1 to 3.

9. The coating system of claim 8 , wherein (B3) comprises a polyaldimine comprising a reaction product of isobutyraldehyde and isophorone diamine.

10. A coating formed from the two-component coating system claim 1 .

11. A two-component polyurea coating composition comprising:

(A) a polyisocyanate;

(B1) a polyaspartic ester corresponding to the following formula:

wherein:

Z′ represents a 1,1,1-tris(methyl)propyl residue; and

R 1 and R 2 represent ethyl residues; and

(B2) a polyetheraspartic ester corresponding to the following formula:

wherein:

n is an integer of 3;

m is independently an integer of 1 to 5;

Z represents a 1,1,1-tris(methyl)propyl residue;

R 1 and R 2 represent ethyl residues; and

R 3 represents isopropyl (1-methylethyl) residues.

12. The coating composition of claim 11 , wherein the polyisocyanate comprises a polyisocyanate adduct selected from the group consisting of an isocyanurate trimer of 1,6-hexamethylene diisocyanate and an iminooxadiazine dione asymmetric trimer of 1,6-hexamethylene diisocyanate.

13. The coating composition of claim 11 , further comprising:

(B3) at least one of a polyaldimine and a polyketimine corresponding to the following formula:

wherein:

R 4 and R 5 are independently hydrogen or a hydrocarbon group with up to 20 carbon atoms, or R 4 and R 5 form a 5-membered or 6-membered cycloaliphatic ring together with the carbon atom;

R 6 is a (p+1)-valent residue obtained by removing the primary amino groups from a corresponding polyamine, optionally containing oxygen; and

p is an integer from 1 to 3.

14. The coating composition of claim 13 , wherein (B3) is a polyaldimine comprising a reaction product of isobutyraldehyde and isophorone diamine.

15. The coating composition of claim 11 , wherein the ratio of un-reacted isocyanate groups to amine groups is 1:1 to 1.5:1.

16. The coating system of claim 11 , further comprising an organic solvent.

17. A coating formed from the two-component coating composition of claim 11 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2016
From: SQUILLER, EDWARD P.; WAYT, TERRELL D.; FORSYTHE, JOHN; BEST, KURT E.; OLSON, AHREN; EKIN, ABDULLAH
To: COVESTRO LLC
Reel/Frame 037963/0336 →
Continuity (2)
Provisional Application 61787538 · Mar 15, 2013
Related Publication 20160024339A1 · Jan 28, 2016