Multi-functional unsaturated polyester polyols

• US 20030148126A1
• Filed: 02/01/2002
• Published: 08/07/2003
• Est. Priority Date: 02/01/2002
• Status: Active Grant

• Current Assignee: AFI Licensing LLC (Armstrong World Industries Incorporated)
• Original Assignee: AWI Licensing Company (Armstrong World Industries Incorporated)
• Inventors: Tian, Dong, Ross, Jeff S.
• Granted Patent: US 6,916,547 B2
• Time in Patent Office: Days
• US Class Current: 428/480
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C09D 167/06 Unsaturated polyesters having carbon-to-carbon unsaturation
• CPC Class Codes: C09D 167/07 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: Y10T 428/24355 Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
• CPC Class Codes: Y10T 428/25 Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
• CPC Class Codes: Y10T 428/257 Iron oxide or aluminum oxide
• CPC Class Codes: Y10T 428/31786 Of polyester [e.g., alkyd, etc.]

Abstract

Novel multifunctional unsaturated polyester polyols, UV-curable top coat formulations including these polyols, and a one-step process for preparing these polyols, are disclosed. Surface coverings and surface covering components including these top coat formulations are also disclosed. The polyols are generally formed by the ring opening polymerization of a lactone with a compound of the formula (R¹)_aR(OH)_b, where a+b>2. R¹ is a double bond-containing moiety such as allyl, vinyl, vinylidene, vinyl ether, acrylate, and the like. R is generally an alkyl, aryl, aralkyl, alkaryl, ether or ester group, including substituted versions thereof. R can be a polymer, including polymers with a plurality of functional groups. Examples of lactone groups which can be used include caprolactone, lactide and glycolide. The polyols can be used in 100% solids, solvent and water based radiation cured coatings, thermal cured coatings, dual cure (thermal with UV/e-beam, or UV/e-beam with thermal curing) coatings, and other types of coatings. These new resins enhance coating performance due to their multi-functional groups in the polymer chain.

Claims

1. a multifunctional unsaturated polyester polyol prepared by reacting a lactone with a compound of the formula (R¹)_aR(OH)_b, wherein:

a and b are, independently, equal to or greater than 1, and a+b combined are greater than 2,

R is an alkyl, aryl, aralkyl, alkaryl, ether or ester group, or substituted versions thereof, and

R¹ is an olefin-containing moiety.

2. The polyol of claim 1 wherein at least one R¹ comprises an allyl, vinyl ether, vinyl, vinylidine or (meth)acrylate group.

3. The polyol of claim 2, wherein a is at least 2 and each R¹ is structurally different.

4. A multifunctional unsaturated polyester polyol of the formula:

(R¹)_aR—

[O—

(C(O)—

(CR²R³)_n—

O—

)_mH)]_b

wherein;

a and b are, independently, equal to or greater than 1, and a+b combined are greater than 2,

n is a number between 1 and 20, typically between 3 and 14,

m is a number between 2 and 50,

R is an alkyl, aryl, aralkyl, alkaryl, ether or ester group, or substituted versions thereof,

R¹ is an olefin-containing moiety, and

R² and R³ are, independently, H, alkyl, aryl, aralkyl, alkaryl, ether, alkoxy, ester, or substituted versions thereof, or R² and R³ combine to form a cycloalkane wherein one or more of the carbons is optionally replaced with a heteroatom,

wherein one or more of the C(R²R³) groups can be replaced with a heteroatom.

5. The polyol of claim 4, wherein at least one R¹ comprises an allyl, vinyl ether, vinyl, vinylidine or (meth)acrylate group.

6. The polyol of claim 4, wherein R is selected from the group consisting of alkyl and alkaryl.

7. The polyol of claim 4, wherein R² and R³ are, independently, selected from the group consisting of H and C_1-6 alkyl.

8. The polyol of claim 4, wherein a is between 2 and about 6.

9. The polyol of claim 4, wherein b is between 2 and 6.

10. The polyol of claim 4, wherein n is between 1 and about 20.

11. A UV-curable top coat formulation comprising the polyol of claim 4.

12. The top coat formulation of claim 11, further comprising one or more additional components, selected from the group consisting of flatting agents, photoinitiators, reactive diluents, hard particles such as aluminum oxide, and adhesion promoters.

13. An e-beam curable top coat formulation comprising the polyol of claim 4.

14. A thermally curable top coat formulation comprising the polyol of claim 4.

15. The formulation of claim 14, wherein the thermal curing involves melamine cross-linking chemistry.

16. A two step curable formulation comprising the polyol of claim 4.

17. The formulation of claim 16 wherein the two step curing comprises both thermal and radiation curing.

18. A surface covering comprising a top coat layer formed from a top coat formulation of comprising the polyol of claim 4.

19. The surface covering of claim 18, wherein the surface covering is a floor covering.

20. The surface covering of claim 19, further comprising a wear layer.

21. The surface covering of claim 19, further comprising a design layer.

22. The surface covering of claim 19, further comprising a foam layer.

23. The surface covering of claim 19, further comprising a base layer.

24. A method of forming a multifunctional unsaturated polyester polyol, comprising:

a) reacting a compound of the formula (R¹)_aR(OH)_b, where a+b>

2, and a is greater than one, with a lactone in the presence of a suitable acid catalyst, wherein;

R is an alkyl, aryl, aralkyl, alkaryl, ether or ester group, or substituted versions thereof, and

R¹ is an olefin-containing moiety.

25. The method of claim 24, wherein R is selected from the group consisting of alkyl and alkaryl.

26. The method of claim 24, wherein at least one R¹ is an allyl, vinyl ether, vinyl, vinylidene or (meth)acrylate group

27. The method of claim 24, wherein a is at least 2 and each R¹ is structurally different.

28. The method of claim 24, wherein a is equal to 2 through 6.

29. The method of claim 24, wherein b is equal to 1 through 6.