IP Library Granted Patent US 10,696,917
Granted Patent B2
US 10,696,917 · App. 15/073,615 · Granted Jun 30, 2020

Low-friction fluorinated coatings

Inventors: Andrew P. Nowak (Los Angeles, CA); Adam F. Gross (Santa Monica, CA); Elena Sherman (Culver City, CA)
Assignee: HRL Laboratories, LLC
C10M169/041C08G18/3812C08G18/4804C08G18/5015C08G18/6505C08G18/6666C08G18/758C08G65/34C08G81/00C08G81/025C09D175/08C10M107/38C10M107/44C10M147/04C10M149/20C10M2201/062C10M2201/084C10M2201/103C10M2201/105C10M2213/0606C10M2217/0453C10N2220/021C10N2230/04C10N2230/06C10N2250/121
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Quick Facts
Patent No.
US 10,696,917
App. No.
15/073,615
Granted
Jun 30, 2020
Kind
B2
Abstract

Low-friction fluorinated coatings are disclosed herein. A preferred low-friction material contains a low-surface-energy fluoropolymer having a surface energy between about 5 mJ/m 2 to about 50 mJ/m 2 , and a hygroscopic material that is covalently connected to the fluoropolymer in a triblock copolymer, such as PEG-PFPE-PEG. The material forms a lubricating surface layer in the presence of humidity. An exemplary copolymer comprises fluoropolymers with average molecular weight from 500 g/mol to 20,000 g/mol, wherein the fluoropolymers are (α,ω)-hydroxyl-terminated and/or (α,ω)-amine-terminated, and wherein the fluoropolymers are present in the triblock structure T-(CH 2 —CH 2 —O)—CH 2 —CF 2 —O—(CF 2 —CF 2 —O) m (CF 2 —O) n —CF 2 —CH 2 —(O—CH 2 —CH 2 ) p -T where T is a hydroxyl or amine terminal group, p=1 to 50, m=1 to 100, and n=1 to 100. The copolymer also contains isocyanate species and polyol or polyamine chain extenders or crosslinkers possessing a functionality of preferably 3 or greater. These durable, solvent-resistant, and transparent coatings reduce insect debris following impact.

Claims (24)

1. A material comprising:

a substantially continuous matrix containing a first component; and

a plurality of inclusions containing a second component, wherein said inclusions are uniformly and intimately dispersed within said matrix;

wherein one of said first component or said second component is a low-surface-energy fluoropolymer having a surface energy between about 5 mJ/m 2 to about 50 mJ/m 2 , and the other of said first component or said second component is a hygroscopic material that is covalently connected to said fluoropolymer in a triblock copolymer,

wherein said material forms a lubricating surface layer in the presence of humidity, and wherein said material is characterized by a coefficient of friction less than 0.2,

wherein said fluoropolymer is perfluoropolyether,

wherein said hygroscopic material is poly(ethylene glycol), and

wherein said triblock copolymer is

wherein:

X, Y═CH 2 —(O—CH 2 —CH 2 ) p -T, and X and Y are independently selected;

p=6 to 50;

T is a hydroxyl or amine terminal group;

m=1 to 100; and

n=1 to 100.

2. The material of claim 1 , wherein said continuous matrix further contains (i) one or more isocyanate species possessing an average isocyanate functionality of about 2 or greater, or a reacted form thereof; and (ii) one or more polyol or polyamine chain extenders or crosslinkers possessing an average functionality of about 2 or greater, or a reacted form thereof.

3. The material of claim 2 , wherein said isocyanate species are selected from the group consisting of 4,4′-methylenebis(cyclohexyl isocyanate), hexamethylene diisocyanate, cycloalkyl-based diisocyanates, tolylene-2,4-diisocyanate, 4,4′-methylenebis(phenyl isocyanate), isophorone diisocyanate, and combinations or derivatives thereof.

4. The material of claim 2 , wherein said polyol or polyamine chain extenders or crosslinkers are selected from the group consisting of 1,3-butanediol, 1,4-butanediol, 1,3-propanediol, 1,2-ethanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, neopentyl glycol, 1,6-hexanediol, 1,4-cyclohexanedimethanol, ethanol amine, diethanol amine, methyldiethanolamine, phenyldiethanolamine, glycerol, trimethylolpropane, 1,2,6-hexanetriol, triethanolamine, pentaerythritol, ethylenediamine, 1,3-propanediamine, 1,4-butanediamine, diethyltoluenediamine, dimethylthiotoluenediamine, isophoronediamine, diaminocyclohexane, N,N,N′,N′-tetrakis(2-hydroxypropyl) ethylenediamine, and homologues, derivatives, or combinations thereof.

5. The material of claim 2 , wherein said one or more polyol or polyamine chain extenders or crosslinkers possess an average functionality of about 3 or greater.

6. The material of claim 1 , wherein said low-surface-energy polymer or said hygroscopic material is surface-treated.

7. The material of claim 1 , said material further comprising one or more additional components selected from the group consisting of a particulate filler, a pigment, a dye, a plasticizer, a flame retardant, a flattening agent, and a substrate adhesion promoter.

8. The material of claim 7 , wherein said particulate filler is selected from the group consisting of silica, alumina, silicates, talc, aluminosilicates, barium sulfate, mica, diatomite, calcium carbonate, calcium sulfate, carbon, wollastonite, and combinations thereof; and wherein said particulate filler is optionally surface-modified with a compound selected from the group consisting of fatty acids, silanes, alkylsilanes, fluoroalkylsilanes, silicones, alkyl phosphonates, alkyl phosphonic acids, alkyl carboxylates, alkyldisilazanes, and combinations thereof.

9. The material of claim 1 , wherein said material is characterized by a water absorption capacity of at least 10 wt % water based on total weight of said material.

10. The material of claim 1 , wherein said material is characterized by a surface contact angle of water of greater than 90°.

11. The material of claim 1 , wherein said material is optically transparent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2016
From: NOWAK, ANDREW P.; GROSS, ADAM F.; SHERMAN, ELENA
To: HRL LABORATORIES, LLC
Reel/Frame 038019/0796 →
Continuity (6)
Continuation In Part 14829640 · Aug 19, 2015
Continuation In Part 14658188 · Mar 14, 2015
Provisional Application 62271193 · Dec 22, 2015
Provisional Application 62038878 · Aug 19, 2014
Provisional Application 61953093 · Mar 14, 2014
Related Publication 20160201005A1 · Jul 14, 2016