Polyurethanes, articles and coatings prepared therefrom and methods of making the same

• US 9,598,527 B2
• Filed: 12/14/2006
• Issued: 03/21/2017
• Est. Priority Date: 09/01/2004
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Rukavina, Thomas G., Hunia, Robert, Wang, Yan
• Primary Examiner(s): SERGENT, RABON A
• Application Number:
  US11/638,876
• Publication Number:
  US 20100124649A1
• Time in Patent Office: 3,750 Days
• Field of Search: 528/60, 528/61, 528/65, 528/85, 428/422.8, 428/423.1
• US Class Current: 1/1
• CPC Class Codes: B32B 11/046 of synthetic resin
• CPC Class Codes: B32B 13/12 of synthetic resin
• CPC Class Codes: B32B 15/08 of synthetic resin
• CPC Class Codes: B32B 21/08 of synthetic resin
• CPC Class Codes: B32B 2307/302 Conductive
• CPC Class Codes: B32B 2307/412 Transparent
• CPC Class Codes: B32B 2307/54 Yield strength; Tensile strength
• CPC Class Codes: B32B 2307/554 Wear resistance
• CPC Class Codes: B32B 2307/558 Impact strength, toughness
• CPC Class Codes: B32B 2307/712 Weather resistant
• CPC Class Codes: B32B 2307/718 Weight, e.g. weight per square meter
• CPC Class Codes: B32B 2551/00 Optical elements
• CPC Class Codes: B32B 2571/02 defensive, e.g. armour plates, anti-ballistic clothing camouflage nets B32B2459/00
• CPC Class Codes: B32B 27/08 of synthetic resin
• CPC Class Codes: B32B 27/10 of paper or cardboard
• CPC Class Codes: B32B 27/12 next to a fibrous or filamentary layer
• CPC Class Codes: B32B 27/40 comprising polyurethanes
• CPC Class Codes: B32B 9/005 comprising one layer of ceramic material, e.g. porcelain, ceramic tile layered products with at least two ceramic layers composed mainly of ceramic B32B18/00
• CPC Class Codes: B32B 9/045 of synthetic resin
• CPC Class Codes: C08G 18/3203 Polyhydroxy compounds
• CPC Class Codes: C08G 18/3206 : aliphatic
• CPC Class Codes: C08G 18/3212 : containing cycloaliphatic groups
• CPC Class Codes: C08G 18/3221 : hydroxylated esters of carboxylic acids other than higher fatty acids
• CPC Class Codes: C08G 18/4277 : Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/44 : Polycarbonates
• CPC Class Codes: C08G 18/73 : acyclic
• CPC Class Codes: C08G 18/758 : containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 18/765 : alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C08G 18/7671 : containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 18/792 : formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 18/798 : containing urethdione groups
• CPC Class Codes: C09D 175/04 : Polyurethanes
• CPC Class Codes: Y10T 428/249924 : Noninterengaged fiber-containing paper-free web or sheet which is not of specified porosity
• CPC Class Codes: Y10T 428/31551 : Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31591 : Next to cellulosic
• CPC Class Codes: Y10T 428/31601 : Quartz or glass

Abstract

The present invention provides polyurethanes including a reaction product of components including: (a) about 1 equivalent of at least one polyisocyanate; (b) about 0.05 to about 0.9 equivalents of at least one branched polyol having 4 to 18 carbon atoms and at least 3 hydroxyl groups; and (c) about 0.1 to about 0.95 equivalents of at least one diol having 2 to 18 carbon atoms, wherein the reaction product components are essentially free of polyester polyol and polyether polyol and the reaction components are maintained at a temperature of at least about 100° C. for at least about 10 minutes, compositions, coatings and articles made therefrom and methods of making the same.

Claims

1. An article comprising a polyurethane comprising a reaction product of components comprising:

(a) about 1 equivalent of at least one polyisocyanate;

(b) about 0.05 to about 0.9 equivalents of at least one branched polyol having 3 to 18 carbon atoms and at least 3 hydroxyl groups; and

(c) about 0.1 to about 0.95 equivalents of sorbitol, mannitol, and/or at least one diol having 2 to 18 carbon atoms,

wherein the reaction product components comprise less than about 5 weight percent of polyester polyol, polycarbonate polyol or polyether polyol and less than about 2 weight percent of amine curing agent on a basis of total weight of the components,

wherein, upon mixing, the reaction components are maintained at a reaction temperature of at least 110°

C. for at least about 10 minutes, degassed, and reacted at a temperature of about 100°

C. to about 140°

C. for at least about 6 hours, and wherein the article is cured at a temperature of from about 120°

C. to about 150°

C. for a curing time period of from about 0.5 to about 72 hours, and

wherein the article has a Gardner Impact strength of from about 100 in-lb (11 Joules) to about 640 in-lb (72 Joules) according to ASTM-D 5420-04, wherein the Gardner Impact strength is measured after the curing time period.

2. The article according to claim 1, wherein the article is selected from the group consisting of transparencies, optical articles, photochromic articles, ballistic resistant articles, and glazings.

3. The article according to claim 1, wherein the article is an airplane transparency.

4. The article according to claim 1, wherein the article is a curved article.

5. The article according to claim 1, wherein the article is a flat article.

6. The article according to claim 1, wherein the article is a molded article.

7. The article according to claim 6, wherein the molded article is a curved article.

8. The article according to claim 6, wherein the molded article is a flat article.

9. An article comprising a polyurethane comprising a reaction product of components comprising:

(a) about 1 equivalent of at least one polyisocyanate;

(b) about 0.1 to about 0.9 equivalents of at least one branched polyol having 3 to 18 carbon atoms and at least 3 hydroxyl groups; and

(c) about 0.1 to about 0.9 equivalents of sorbitol, mannitol, and/or at least one diol having 2 to 18 carbon atoms,

wherein the reaction product components comprise less than about 5 weight percent of polyester polyol, polycarbonate polyol or polyether polyol, less than about 2 weight percent of amine curing agent on a basis of total weight of the components, and

wherein, upon mixing, the reaction components are maintained at a reaction temperature of at least 110°

C. for at least about 10 minutes, degassed, and reacted at a temperature of about 100°

C. to about 140°

C. for at least about 6 hours, and wherein the article is cured at a temperature of from about 120°

C. to about 150°

C. for a curing time period of from about 0.5 to about 72 hours, and

wherein the article has a Gardner Impact strength of at least about 200 in-lb (23 Joules) according to ASTM-D 5420-04, wherein the Gardner Impact strength is measured after the curing time period.

10. The article according to claim 9, wherein the article is selected from the group consisting of transparencies, optical articles, photochromic articles, ballistic resistant articles, and glazings.

11. The article according to claim 9, wherein the article is an airplane transparency.

12. The article according to claim 9, wherein the article is a curved article.

13. The article according to claim 9, wherein the article is a flat article.

14. The article according to claim 9, wherein the article is a molded article.

15. The article according to claim 14, wherein the molded article is a curved article.

16. The article according to claim 14, wherein the molded article is a flat article.