Water- and oil-repellent fluoroacrylates

• US 7,659,351 B2
• Filed: 03/19/2007
• Issued: 02/09/2010
• Est. Priority Date: 12/31/2003
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Kinning, David J., Moore, George G I., Kirk, Alan R., Caldwell, Gregg A., Klun, Thomas P., Qiu, Zai-Ming, Ross, Richard B., Kumar, Ramesh C., Mader, Roger A., Clark, John C.
• Primary Examiner(s): Wu; David
• Assistant Examiner(s): BERNSHTEYN, MICHAEL
• Application Number:
  US11/688,074
• Publication Number:
  US 20070173149A1
• Time in Patent Office: 1,058 Days
• Field of Search: 526/242, 526/286, 526/319, 528/70, 524/544, 560/167
• US Class Current: 526/242
• CPC Class Codes: C07C 271/20 to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 311/09 the carbon skeleton being further substituted by at least two halogen atoms
• CPC Class Codes: C08F 220/387 and containing nitrogen and oxygen
• CPC Class Codes: Y10T 442/2287 Fluorocarbon containing

Abstract

Fluoroacrylates comprise the reaction product of:

• • (a) at least one fluorochemical alcohol represented by the formula:
    C_nF_2n+1—X—OH
  • wherein:
    • n=1 to 4,

• • • R=hydrogen or an alkyl group of 1 to 4 carbon atoms,
    • m=2 to 8,
    • R_f=C_nF_2n+1,
    • y=0 to 6, and
    • q=1 to 8;
  • (b) at least one unbranched symmetric diusocyanate; and
  • (c) at least one hydroxy-terminated alkyl (meth)acrylate or 2-fluoro acrylate monomer having 2 to about 30 carbon atoms in its alkylene portion.

Claims

1. A fluoroacrylate represented by the following general formula:

C_nF_2n+1—

X—

OC(O)NH-A-HNC(O)O—

(C_pH_2p)(O)COC(R′

)═

CH₂

wherein;

n=1 to 5,

2. The fluoroacrylate of claim 1 wherein said n is 1 to 4.

3. The fluoroacrylate of claim 2 wherein n is 4.

4. The fluoroacrylate of claim 1 wherein said X is

5. The fluoroacrylate of claim 4 wherein said R is CH₃.

6. The fluoroacrylate of claim 5 wherein said m is 2 to 4.

7. The fluoroacrylate of claim 1 wherein said A is selected from the group consisting of —

C₆H₁₂—

,

8. The fluoroacrylate of claim 7 wherein said A is

9. The fluoroacrylate of claim 1 wherein said p is 2 to 12.

10. The fluoroacrylate of claim 9 wherein said p is selected from the group consisting of 2, 4, 6, 10, and 12.

11. The fluoroacrylate of claim 10 wherein said p is 2.

12. The fluoroacrylate of claim 1 wherein said R′

is H.

14. A fluorinated acrylic polymer comprising repeating units of the fluoroacrylate of claim 1.

15. The fluorinated acrylic polymer of claim 14 further comprising repeating units derived from one or more nonfunctional comonomers.

16. The fluorinated acrylic polymer of claim 14 further comprising repeating units derived from one or more functional comonomers.

17. A coating composition comprising a solvent and the fluorinated acrylic polymer of claim 14.

18. An article comprising a substrate having one or more surfaces coated with the coating composition of claim 17.

19. The article of claim 18 wherein said substrate is a hard substrate or a fibrous substrate.

20. A release coating composition comprising a solvent and the fluorinated acrylic polymer of claim 14.

21. An article comprising a substrate having one or more surfaces coated with the release coating composition of claim 20.

13. A fluorinated isocyanate represented by the following general formula:

C_nF_2n+1—

X—

OC(O)NH-A-NCO

wherein;

n=1 to 5,