Functionalized F-POSS monomer compositions and uses thereof

• US 10,442,823 B2
• Filed: 09/14/2017
• Issued: 10/15/2019
• Est. Priority Date: 10/07/2014
• Status: Active Grant

• Current Assignee: Henkel AG & Co KGaA
• Original Assignee: NBD Nanotechnologies, Inc. (Henkel AG & Co KGaA)
• Inventors: Warner, John C., Loebelenz, Jean R., Cheruku, Srinivasa Rao, Gero, Thomas Woodrow, Catchings, Sr., Perry L.
• Primary Examiner(s): Brooks, Clinton A
• Assistant Examiner(s): Adzamli, Kofi
• Application Number:
  US15/705,089
• Publication Number:
  US 20180094006A1
• Time in Patent Office: 761 Days
• Field of Search: None
• CPC Class Codes: C07F 7/21 Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
• CPC Class Codes: C08G 77/045 containing less than 25 silicon atoms
• CPC Class Codes: C08G 77/24 halogen-containing groups
• CPC Class Codes: C08K 5/549 containing silicon in a ring
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C09D 7/62 modified by treatment with other compounds

Abstract

Functionalized F-POSS compounds comprising synthetic blends of at least two feedstocks that produce a distribution of fluorinated polyhedral oligomeric silsesquioxane molecule structures and/or functional groups.

Claims

1. A process for preparing a compound having a formula

2. The process of claim 1, wherein R² is C₁-C₈ alkyl, wherein each hydrogen atom in R² is independently optionally substituted by an R³.

3. The process of claim 1, wherein R³ is —

NCO, —

OR⁴, —

OC(O)R⁴, —

C(O)OR⁴, —

C(O)R⁴ or —

OC(O)OR⁴.

4. The process of claim 1, wherein R⁴ is C₁-C₈ alkyl and wherein each hydrogen atom in R⁴ is independently optionally substituted by an R⁶.

5. The process of claim 1, wherein R⁴ is C₂-C₈ alkenyl, wherein each hydrogen atom in R⁴ is independently optionally substituted by an R⁶.

6. The process of claim 1, wherein R⁶ is C₁-C₈ alkyl, —

NCO, —

OR⁷, —

NR⁷R⁸, —

OC(O)R⁷, —

C(O)OR⁷, —

C(O)R⁷ or —

OC(O)OR⁷.

7. The process of claim 1, wherein R⁷ is C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₆-C₁₀ aryl or 5-7 membered heteroaryl, wherein each hydrogen atom in R⁷ is independently optionally substituted by one or more R⁹.

8. The process of claim 1, wherein R⁹ is hydrogen or C₁-C₈ alkyl, and when R⁹ is C₁-C₈ alkyl, R⁹ is optionally substituted by a —

OC(O)R¹⁰.

9. The process of claim 1, wherein R¹⁰ is H or C₁-C₈ alkyl, and when R¹⁰ is C₁-C₈ alkyl, each hydrogen atom in R¹⁰ is independently optionally substituted by a fluorine atom.

10. The process of claim 1, wherein R² is n-propyl, wherein each hydrogen atom in R² is independently optionally substituted by an R³.

11. The process of claim 10, wherein R³ is —

OC(O)R⁴ or —

OC(O)OR⁴.

12. The process of claim 11, wherein R⁴ is methyl.

13. The process of claim 11, wherein R⁴ is —

CH═

CH₂, wherein each hydrogen atom in R⁴ is independently optionally substituted by an R⁶.

14. The process of claim 13, wherein R⁶ is C₁-C₈ alkyl.

15. The process of claim 14, wherein R⁶ is methyl.

16. The process of claim 10, wherein the long chain fluorinated alkyl is 8/2, 6/2 or 4/2.

17. The process of claim 1, wherein the long chain fluorinated alkyl is 8/2, 6/2 or 4/2.

18. The process of claim 1, wherein the base is potassium hydroxide or tetraethylammonium hydroxide.

19. The process of claim 2, wherein R³ is —

NH₂.

20. The process of claim 19, wherein the base is potassium hydroxide or tetraethylammonium hydroxide.