Synthetic blend F-POSS compositions formed from multiple feedstock materials

• US 9,409,933 B2
• Filed: 10/07/2015
• Issued: 08/09/2016
• 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 Charles
• Primary Examiner(s): MOORE, MARGARET G
• Application Number:
  US14/876,911
• Publication Number:
  US 20160096853A1
• Time in Patent Office: 307 Days
• US Class Current: 1/1
• 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

Abstract

The present disclosure relates, in exemplary embodiments, to compositions of matter comprising synthetic blends of at least two feedstocks that produce a distribution of fluorinated polyhedral oligomeric silsesquioxane molecule structures. The present disclosure also relates, in exemplary embodiments, to methods of making such synthetic blends.

Claims

1. An F-POSS compound of the formula

2. The F-POSS compound of claim 1, wherein each long-chain fluorinated alkyl is independently from 5 to 12 carbon atoms in the longest continuous chain of carbon atoms.

3. The F-POSS compound of claim 1, wherein each long-chain fluorinated alkyl is independently selected from the group consisting of 4/2 fluorinated alkyl, 3/3 fluorinated alkyl, 6/2 fluorinated alkyl, 4/4 fluorinated alkyl, 8/2 fluorinated alkyl and 6/4 fluorinated alkyl.

4. The F-POSS compound of claim 1, wherein R¹ is 4/2 fluorinated alkyl and R² is 6/2 fluorinated alkyl.

5. An F-POSS composition comprising a mixture of compounds of the formula

6. The F-POSS composition of claim 5, wherein each long-chain fluorinated alkyl is independently from 5 to 12 carbon atoms in the longest continuous chain of carbon atoms.

7. The F-POSS composition of claim 5, wherein each long-chain fluorinated alkyl is independently selected from the group consisting of 4/2 fluorinated alkyl, 3/3 fluorinated alkyl, 6/2 fluorinated alkyl, 4/4 fluorinated alkyl, 8/2 fluorinated alkyl and 6/4 fluorinated alkyl.

8. The F-POSS composition of claim 7, wherein R¹ is 4/2 fluorinated alkyl and R² is 6/2 fluorinated alkyl.

9. The F-POSS composition of claim 5, wherein the mixture of compounds comprises a distribution of compounds having a ratio of R¹ to R² between 0:

8 to 8;

0.

10. The F-POSS composition of claim 9, wherein the distribution is a Gaussian distribution.

11. An F-POSS composition produced by a process comprising:

contacting a first feedstock comprising a first fluorinated trialkoxysilane with a second feedstock comprising a second fluorinated trialkoxysilane, wherein the first fluorinated trialkoxysilane and the second fluorinated trialkoxysilane are different.

12. The F-POSS composition of claim 11, wherein the first fluorinated trialkoxysilane is of the formula R¹Si(OR^A)₃, and the second fluorinated trialkoxysilane is of the formula R²Si(OR^B)₃, wherein each of R¹ and R² are independently a long-chain fluorinated alkyl, each R^A and R^B is independently C₁-C₆ alkyl, provided that R¹ and R² are different.

13. The F-POSS composition of claim 12, wherein each long-chain fluorinated alkyl is independently from 5 to 12 carbon atoms in the longest continuous chain of carbon atoms.

14. The F-POSS composition of claim 13, wherein each long-chain fluorinated alkyl is independently selected from the group consisting of 4/2 fluorinated alkyl, 3/3 fluorinated alkyl, 6/2 fluorinated alkyl, 4/4 fluorinated alkyl, 8/2 fluorinated alkyl and 6/4 fluorinated alkyl.

15. The F-POSS composition of claim 12, wherein R¹ is 4/2 fluorinated alkyl and R² is 6/2 fluorinated alkyl.

16. The F-POSS composition of claim 15, wherein the composition comprises a mixture of compounds in a distribution having a ratio of R¹ to R² between 0:

8 to 8;

0.

17. The F-POSS composition of claim 16, wherein the distribution is a Gaussian distribution.

18. A paint composition, comprising:

a. at least one polymer base paint material; and

b. a polymer synthetic blend composition comprising polymer synthetic blend composition of fluorinated polyhedral oligomeric silsesquioxane (“

F-POSS”

), comprising;

a mixture of feedstock materials comprising

i. a first feedstock comprising a first fluorinated triethoxysilane having a carbon chain length of C₁x, where x is the number of carbons, and,

ii. a second feedstock comprising a second fluorinated triethoxysilane having a carbon chain length of C₂y, where y is the number of carbons, wherein x is greater than y,

whereby the polymer blend composition resulting from the mixing of the first and second feedstocks comprises a distribution of molecules, each molecule comprising a matrix structure having eight apices, each apex having a substituent R, each substituent R having a carbon chain length Cn, such that a portion of the distribution of molecules has all substituents R having the same carbon chain length Cn and a portion of the distribution of molecules has at least one substituent R1 having a carbon chain length C₁x and R2 having a carbon chain length C₂y wherein C1 is greater than C2.

19. The paint composition of claim 18, wherein the polymer base paint material comprises at least one material selected from the group consisting of a polyurethane, polyester, polypropylene, polybutylene, poly(L-lactic acid), polycellulosic, polyhydroxy alkanate, lignose cellulose, polyethylene oxide, epoxy, epoxy resin, alkyd resin, polyether, and mixtures of at least two of the foregoing.

20. The paint composition of claim 18, wherein the paint composition has a water contact angle of at least 110 degrees and a hexadecane contact angle of at least 70 degrees.