WATER- AND OIL-REPELLENT FLUOROURETHANES AND FLUOROUREAS

• US 20060142474A1
• Filed: 12/12/2005
• Published: 06/29/2006
• Est. Priority Date: 12/28/2004
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Moore, George G. I., Klun, Thomas P., Qiu, Zai-Ming, Jariwala, Chetan P., Kumar, Ramesh C., Clark, John C.
• Granted Patent: US 7,268,197 B2
• Time in Patent Office: Days
• US Class Current: 524/589
• CPC Class Codes: C08G 18/2845 Monohydroxy epoxy compounds
• CPC Class Codes: C08G 18/2885 containing halogen atoms
• CPC Class Codes: C08G 18/3228 acyclic
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/6212 Polymers of alkenylalcohols; Acetals thereof; Oxyalkylation products thereof
• CPC Class Codes: C08G 18/6705 Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
• CPC Class Codes: C08G 18/71 Monoisocyanates or monoisothiocyanates
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

A fluorochemical compound comprises the reaction product of: (a) the reaction product of: (i) at least one fluorochemical alcohol represented by the formula:
C_nF_2n+1—X—OH
wherein: 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, q=1 to 8; and (ii) at least one unbranched symmetric diisocyanate, and (b) at least one co-reactant comprising two or more functional groups that are capable of reacting with an isocyanate group.

Claims

1. A fluorochemical compound comprising the reaction product of:

(a) the reaction product of;

(i) at least one fluorochemical alcohol represented by the formula;

C_nF_2n+1—

X—

OH

wherein;

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,

q=1 to 8; and

(ii) at least one unbranched symmetric diisocyanate, and

(b) at least one co-reactant comprising two or more functional groups that are capable of reacting with an isocyanate group.

2. The fluorochemical compound of claim 1 wherein n=1 to 5.

3. The fluorochemical compound of claim 2 wherein n=4.

4. The fluorochemical compound of claim 1 wherein X is

5. The fluorochemical compound of claim 1 wherein the fluorochemical alcohol is C₄F₉SO₂NCH₃(CH₂)₂OH.

6. The fluorochemical compound of claim 1 wherein the unbranched symmetric diisocyanate is 4,4′

-diphenylmethane diisocyanate.

7. The fluorochemical compound of claim 1 wherein the co-reactant comprises two or more -Z-H groups, wherein each Z is independently selected from the group consisting of O, N, and S.

8. The fluorochemical compound of claim 7 wherein Z is O or N.

9. The fluorochemical compound of claim 1 wherein the co-reactant is a polyol.

10. The fluorochemical compound of claim 1 wherein the co-reactant is a polyamine.

11. The fluorochemical compound of claim 1 wherein the co-reactant is a polythiol.

22. A coating composition comprising a solvent and the fluorochemical compound of claim 1.

23. The coating composition of claim 22 wherein the coating composition is a release coating.

25. An article comprising a substrate having one or more surfaces coated with the coating composition of claim 22.

26. The article of claim 25 wherein the substrate is a hard substrate or a fibrous substrate.

12. A fluorochemical compound comprising the reaction product of:

(a) at least one fluorinated isocyanate represented by the following general formula;

C_nF_2n+1—

X—

OC(O)NH-A-NCO

wherein;

R=H or an alkyl group of 1 to 4 carbon atoms,

m=2 to 8,

R_f=C_nF_2n+1,

y=0 to 6,

q=1 to 8, and

A=an unbranched symmetric alkylene group, arylene group, or aralkylene group; and

(b) at least one co-reactant comprising two or more functional groups that are capable of reacting with an isocyanate group.

13. The fluorochemical compound of claim 12 wherein n=1 to 5.

14. The fluorochemical compound of claim 13 wherein n=4.

15. The fluorochemical compound of claim 12 wherein X

16. The fluorochemical compound of claim 12 wherein A

17. The fluorochemical compound of claim 12 wherein the co-reactant comprises two or more -Z-H groups, wherein each Z is independently selected from the group consisting of O, N, and S.

18. The fluorochemical compound of claim 17 wherein Z is O or N.

19. The fluorochemical compound of claim 12 wherein the co-reactant is a polyol.

20. The fluorochemical compound of claim 12 wherein the co-reactant is a polyamine.

21. The fluorochemical compound of claim 12 wherein the co-reactant is a polythiol.

24. A coating composition comprising a solvent and the fluorochemical compound of claim 12.

27. An article comprising a substrate having one or more surfaces coated with the coating composition of claim 24.

28. The article of claim 27 wherein the substrate is a hard substrate or a fibrous substrate.

29. A method for making a fluorochemical compound comprising:

(a) reacting at least one fluorochemical alcohol with at least one unbranched symmetric diisocyanate to form a fluorinated isocyanate, the fluorochemical alcohol being represented by the formula;

C_nF_2n+1—

X—

OH

wherein;

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,

q=1 to 8; and

(b) reacting the fluorinated isocyanate with at least one compound comprising two or more functional groups that are capable of reacting with an isocyanate group.

30. A method for making a fluorochemical compound comprising:

reacting (a) at least one compound comprising two or more functional groups that are capable of reacting with an isocyanate group, and (b) at least one fluorinated isocyanate represented by the formula;

C_nF_2n+1—

X—

OC(O)NH-A-NCO

wherein;