URETHANE POLYOL PRECURSORS FOR COATING COMPOSITIONS

• US 20100227169A1
• Filed: 05/18/2010
• Published: 09/09/2010
• Est. Priority Date: 01/27/2004
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Rukavina, Thomas G.
• Granted Patent: US 7,935,422 B2
• Time in Patent Office: Days
• US Class Current: 428/412
• CPC Class Codes: B32B 17/10018 comprising only one glass sheet
• CPC Class Codes: B32B 17/1033 Laminated safety glass or glazing containing temporary protective coatings or layers
• CPC Class Codes: B32B 2307/584 Scratch resistance
• CPC Class Codes: B32B 2307/712 Weather resistant
• CPC Class Codes: B32B 2369/00 Polycarbonates
• CPC Class Codes: B32B 2457/20 Displays, e.g. liquid crystal displays, plasma displays
• CPC Class Codes: B32B 2605/006 Transparent parts other than made from inorganic glass, e.g. polycarbonate glazings
• CPC Class Codes: B32B 27/40 comprising polyurethanes
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/44 Polycarbonates
• CPC Class Codes: C08G 18/664 with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08J 2475/00 Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C09D 175/06 from polyesters
• CPC Class Codes: Y10T 428/31507 Of polycarbonate
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31598 Next to silicon-containing [silicone, cement, etc.] layer
• CPC Class Codes: Y10T 428/31601 : Quartz or glass

Abstract

Unsymmetrical polyurethane polyol prepolymers are disclosed for use in the formation of coating compositions. The prepolymers are prepared as a reaction product of a diisocyanate with a short chain aliphatic dial and a long chain polymeric diol. The prepolymers are intended as the first component for reaction with a second component polyisocyanate in a two-component coating composition. The coating compositions exhibit excellent abrasion resistance and weatherability, and are particularly useful as coatings for polymeric window transparencies.

Claims

1-9. -9. (canceled)

10. A coating composition, comprising the reaction product of:

a) a polyurethane polyol precursor comprising the reaction product of;

i) a diisocyanate;

ii) an aliphatic diol having 1-6 carbon atoms; and

iii) a polymeric diol having at least one oxycarbonyl linkage and having from 5-20 carbon atoms; and

b) a polyisocyanate.

11. A coating composition as in claim 10, wherein the polyisocyanate is selected from 2,4,6-trioxo-1,3,5-tris(6-isocyanatohexyl)hexahydro-1,3,5-triazine, N-isocyanatohexylaminocarbonyl-N,N′

-bis(isocyanatohexyl)urea, the biuret of hexanediisocyanate, polymeric methane diisosocyanate, and polymeric isophorone diisocyanate.

12. A coating composition as in claim 10, wherein the composition further comprises a catalyst for promoting reaction of the polyurethane polyol precursor with the polyisocyanate.

13. A coating composition as in claim 10, wherein the catalyst is selected from dibutyltin dilaurate, dibutyltin diacetate, stannous octoate, butyl stannoic acid, and bismuth carboxylate.

14. A coating composition as in claim 10, wherein the composition further comprises one or more additives selected from the group consisting of antioxidants, colorants, UV absorbers, light stabilizers, and surfactants.

15. A coating composition as in claim 10, wherein the diisocyanate of the polyurethane polyol precursor is selected from 2,2,4-trimethylhexamethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,1′

-methylene-bis-(4-isocyanatocyclohexane), 4,4′

-methylene-bis-(cyclo hexyl diisocyanate), hydrogenated toluene diisocyanate, 4,4′

-isopropylidene-bis-(cyclohexyl isocyanate), 1,4-cyclohexyl diisocyanate, 4,4′

-dicyclohexyldiisocyanate, and 3-isocyanato methyl-3,5,5-trimethylcyclohexyl diisocyanate, and mixtures and combinations thereof.

16. A coating composition as in claim 10, wherein the aliphatic diol is selected from 1,2-propanediol, ethyl-1,3-hexanediol, 1,6-hexanediol, 2-methyl propanediol, and 1,5-pentanediol, and mixtures and combinations thereof.

17. A coating composition as in claim 10, wherein the polymeric diol is selected from polycarbonate diols and polycaprolactone diols, and mixtures thereof.

18. A coating composition as in claim 10, wherein the polyurethane polyol precursor comprises the reaction product of 2,2,4-trimethylhexamethylene diisocyanate, 1,5-pentanediol, and polyoxohexylene carbonate diol.

19. A coating composition as in claim 18, wherein the polyurethane polyol precursor is further reacted with 2,4,6-trioxo-1,3,5-tris(6-isocyanatohexyl)hexahydro-1,3,5-triazine in the presence of dibutyltin dilaurate as a catalyst.

24. The coating composition of claim 10, wherein the aliphatic diol is a linear aliphatic diol, wherein the polymeric diol is a linear polymeric diol, and wherein the ratio of the diisocyanate:

aliphatic diol polymeric diol is from about 1;

1.9;

0.1 to about 1;

1.1;

0.9.

20. A substrate having a coating on at least one surface thereof, said coating comprising the reaction product of:

a) a polyurethane polyol precursor comprising the reaction product of;

i) a diisocyanate;

ii) an aliphatic diol having 1-6 carbon atoms; and

iii) a polymeric dial having at least one oxycarbonyl linkage and having from 5-20 carbon atoms; and

b) a polyisocyanate.

21. A substrate as in claim 20, wherein the substrate is glass.

22. A substrate as in claim 20, wherein the substrate comprises a polymeric material.

23. A substrate as in claim 22, wherein the substrate comprises a polycarbonate sheet.

25. The substrate of claim 20, wherein the aliphatic diol is a linear aliphatic diol, wherein the polymeric diol is a linear polymeric diol, and wherein the ratio of the diisocyanate:

aliphatic diol;

polymeric diol is from about 1;

1.9;

0.1 to about 1;

1.1;

0.9.