Urethane polyol precursors for coating compositions

• US 7,935,422 B2
• Filed: 05/18/2010
• Issued: 05/03/2011
• Est. Priority Date: 01/27/2004
• Status: Expired due to Fees

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Rukavina, Thomas G.
• Primary Examiner(s): Tran; Thao T.
• Application Number:
  US12/782,252
• Publication Number:
  US 20100227169A1
• Time in Patent Office: 350 Days
• Field of Search: 428/423.1, 428/425.6, 528/45, 528/49, 528/65
• US Class Current: 428/423.1
• 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. 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;

b) a polyisocyanate,

wherein the coating composition comprises a molar ratio of diisocyanate;

aliphatic diol;

polymeric diol from about 1;

1.9;

0.1 to about 1;

1.1;

0.9; and

wherein the polyurethane polyol consists of hydroxyl termination.

2. The coating composition as in claim 1, 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 diisocyanatediisosocyanate, and polymeric isophorone diisocyanate.

3. The coating composition as in claim 1, wherein the composition further comprises a catalyst for promoting reaction of the polyurethane polyol precursor with the polyisocyanate.

4. The coating composition as in claim 1, wherein the catalyst is selected from dibutyltin dilaurate, dibutyltin diacetate, stannous octoate, butyl stannoic acid, and bismuth carboxylate.

5. The coating composition as in claim 1, wherein the composition further comprises one or more additives selected from the group consisting of antioxidants, colorants, UV absorbers, light stabilizers, and surfactants.

6. The coating composition as in claim 1, 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-(cyclohexyl 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.

7. The coating composition as in claim 1, 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.

8. The coating composition as in claim 1, wherein the polymeric diol is selected from polycarbonate diols and polycaprolactone diols, and mixtures thereof.

9. The coating composition of claim 1, wherein the aliphatic diol is a linear aliphatic diol, and wherein the polymeric diol is a linear polymeric diol.

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,

wherein the polyurethane polyol precursor comprises the reaction product of 2,2,4-trimethylhexamethylene diisocyanate, 1,5-pentanediol, and polyoxohexylene carbonate diol.

11. 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;

wherein the polyurethane polyol precursor comprises the reaction product of 2,2,4-trimethylhexamethylene diisocyanate, 1,5-pentanediol, and polyoxohexylene carbonate diol; and

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.

12. 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 diol having at least one oxycarbonyl linkage and having from 5-20 carbon atoms;

b) a polyisocyanate,

wherein the coating composition comprises a molar ratio of diisocyanate;

aliphatic diol;

polymeric dial from about 1;

1.9;

0.1 to about 1;

1.1;

0.9; and

wherein the polyurethane polyol consists of hydroxyl termination.

13. A substrate as in claim 12, wherein the substrate is glass.

14. A substrate as in claim 12, wherein the substrate comprises a polymeric material.

15. A substrate as in claim 14, wherein the substrate comprises a polycarbonate sheet.

16. The substrate of claim 12, wherein the aliphatic diol is a linear aliphatic diol, and wherein the polymeric diol is a linear polymeric diol.