IP Library Granted Patent US 10,392,409
Granted Patent B2
US 10,392,409 · App. 15/471,740 · Granted Aug 27, 2019

Functionalized F-POSS materials as additives to polymers

Inventors: Cheng Diao (Auburndale, MA); Esra Altinok (Medford, MA); Bong June Zhang (Chestnut Hill, MA); Perry L. Catchings, Sr. (Roxbury, MA)
Assignee: NBD NANOTECHNOLOGIES, INC.
C07F7/1804C07F7/21C08K5/549
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Quick Facts
Patent No.
US 10,392,409
App. No.
15/471,740
Granted
Aug 27, 2019
Kind
B2
Abstract

Functionalized fluoro polyhedral oligomeric silsesquioxane (F-POSS) materials as additives to improve liquid repellence of various polymers, the additive including at least one functionalized F-POSS material, wherein the functional group is at least one material selected from the group consisting of amines, isocyanates, epoxies, carboxylic acids, and esters.

Claims (32)

1. A method for synthesizing a functionalized F-POSS comprising:

a) mixing a fluorinated alkylsilane (FAS) and at least one functionalized silane at a mole ratio of either 7:1, 6:2, 5:3, 4:4, 3:5, 2:6, or 1:7;

b) adding the mixture of step a) into a solvent;

c) adding an aqueous KOH solution as a catalyst to the solvent;

d) stirring the above at room temperature; and,

e) collecting precipitated final product.

2. The method of claim 1 , further comprising step f) washing the precipitated final product with ethanol and then drying.

3. The method of claim 1 , comprising combining the functionalized F-POSS and a polymer in the following amounts:

f) functionalized F-POSS: 0.05 wt %-50 wt % and,

g) polymers: 99.5% wt-50 wt %.

4. The method of claim 1 , wherein the solvent is a combination of an alkane and a mixture of ethanol and isopropyl alcohol.

5. The method of claim 4 , wherein the alkane is selected from the group consisting of heptane, octane, pentane and combinations of at least two of the foregoing.

6. A method of forming a composite, comprising:

h) providing the functionalized F-POSS formed according to the method of claim 1 and a thermoplastic polyurethane; and,

i) compounding the foregoing in a compounder to form pellets.

7. An additive in a polymer formulation used in the manufacture of shoes, the additive being made according to the method of claim 1 .

8. The method of claim 3 , wherein the polymer is at least one polymer selected from the group consisting of polyurethanes, polyamides, polyacrylates, polyolefins, polyesters, polyethers, fluorinated polymers, and polystyrenes.

9. The method of claim 8 , wherein the polymer is a polyurethane.

10. The method of claim 1 , wherein the functionalized silane comprises an amine, an isocyanate, an epoxy, a carboxylic acids, or an ester.

11. The method of claim 10 , comprising combining the functionalized F-POSS and a polymer wherein the polymer is at least one polymer selected from the group consisting of polyurethanes, polyamides, polyacrylates, polyolefins, polyesters, polyethers, fluorinated polymers, and polystyrenes.

12. The method of claim 11 , wherein the polymer is a polyurethane.

13. The method of claim 12 , wherein the functionalized silane comprises an amine.

14. The method of claim 1 , wherein the functionalized silane is of the formula

(CH 3 —(CH 2 ) n —O) 3 —Si—(CH 2 ) m —X

wherein:

n is 0 to 15,

m is 1 to 18; and

X is selected from the group consisting of —NH 2 , —NCO, —COOH, —COO − , epoxy, —OH, —SCN, —(C 6 H 6 ), —N(CH 3 ) 3 + Cl − , halogen, —SH, cyano, alkoxy, aryloxy, N-carbamyl, thiocarbamyl, amido, sulfinyl, sulfonyl, sulfonamido, alkylthio, arylthio, heterocyclic, heteroaryl, heterocycloalkyl, quaternary ammonium, cycloalkyl, carbonyl, oxo, nitro, alkenyl, and alkynyl.

15. The method of claim 14 , wherein X is —NH 2 .

16. The method of claim 1 , wherein the functionalized silane is (3-aminopropyl)triethoxysilane.

17. The method of claim 16 , wherein the FAS is 1H,1H,2H,2H-perfluorooctyltriethoxysilane.

18. The method of claim 17 , wherein the method further comprises compounding the functionalized F-POSS with a thermoplastic polyurethane.

Assignments (3)
CORRECTIVE ASSIGNMENT TO REMOVE U.S. PATENT NOS. 10,525,504 AND U.S. PATENT APPLICATION NO. 14/268,757 PREVIOUSLY RECORDED AT REEL: 065406 FRAME: 0320. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 13, 2025
From: NBD NANOTECHNOLOGIES INC.
To: HENKEL AG & CO. KGAA
Reel/Frame 070510/0967 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2023
From: NBD NANOTECHNOLOGIES INC.
To: HENKEL AG & CO. KGAA
Reel/Frame 065406/0320 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2017
From: DIAO, CHENG; ALTINOK, ESRA; ZHANG, BONG JUNE; CATCHINGS, PERRY L., SR.
To: NBD NANOTECHNOLOGIES, INC.
Reel/Frame 041837/0227 →
Continuity (2)
Provisional Application 62313948 · Mar 28, 2016
Related Publication 20170275437A1 · Sep 28, 2017