Method for protection of stone with fluorinated urethane

• US 6,790,924 B2
• Filed: 06/13/2002
• Issued: 09/14/2004
• Est. Priority Date: 02/22/2001
• Status: Expired due to Fees

• Current Assignee: The Chemours Company FC, LLC (The Chemours Company)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Anton, Douglas Robert, Kirchner, Jack Robert, Tuminello, William Howard
• Primary Examiner(s): GORR, RACHEL F
• Application Number:
  US10/168,117
• Publication Number:
  US 20030050367A1
• Time in Patent Office: 824 Days
• Field of Search: 427/385.5, 428/421, 528/49, 528/70, 525/17
• US Class Current: 528/49
• CPC Class Codes: C04B 41/4884 Polyurethanes; Polyisocyanates
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers

Abstract

This invention relates to the application of fluorinated urethane compositions to stone in order to protect the stone from the deleterious effects of water and pollution.

Claims

1. A process comprising contacting stone with a non-polymeric urethane having the formula

2. The process of claim 1 wherein p=1, R¹ is a diradical, R² is perfluoroalkyl or alkyl.

3. The process of claim 2 wherein R¹ is a cycloaliphatic diradical, R² is methyl, ethyl, or perfluoroalkyl, R³ is hydrogen, n=0, and m=1 to 20.

4. The process of claim 3 wherein m=1, R² is a perfluoroalkyl radical having from 5-13 carbons, and R¹ is a cycloaliphatic diradical represented by the formula

wherein R⁵, R⁶, and R⁷ are all methyl.

5. The process of claim 4 wherein R⁵, R⁶, and R⁷ are methyl.

6. The process of claim 1 wherein said solution comprises supercritical CO₂.

7. The process of claim 6 wherein said solution further comprises an organic solvent which is fugitive at a temperature at or above about 0°

C.

8. The process of claim 7 wherein said organic solvent is selected from the group consisting of acetone, methyl-ethyl ketone, methyl isobutyl ketone, ethyl acetate, t-butyl acetate, hydrochlorofluorocarbons, and perfluorocarbons.

9. The process of claim 7 wherein the solvent is methyl isobutyl ketone.

10. A composition comprising stone and a non-polymer urethane having the formula

11. The composition of claim 10 wherein p=1, R¹ is a diradical, R² is perfluoroalkyl or alkyl.

12. The composition of claim 11 wherein R¹ is a cycloaliphatic diradical, R² is methyl, ethyl, or perfluoroalkyl, R³ is hydrogen, n=0, and m=1 to 20.

13. The composition position of claim 12 wherein m=1, R²is a perfluoroalkyl radical having from 5-13 carbons, and R₁ is a cycloaliphatic diradical represented by the formula

wherein R⁵, R⁶, and R⁷ are all alkyl.

14. The composition of claim 13 wherein R⁵, R⁶, and R⁷ are methyl.