IP Library Granted Patent US 8,044,006
Granted Patent B2
US 8,044,006 · App. 12/908,058 · Granted Oct 25, 2011

Composition comprising perfluoropolyether

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Quick Facts
Patent No.
US 8,044,006
App. No.
12/908,058
Granted
Oct 25, 2011
Kind
B2
Abstract

A composition is disclosed which comprises an aryl perfluoropolyether, optionally a halogenated oil, and further optionally a thickening agent. The composition can be used as a lubricant itself or as an additive to an oil or grease lubricant and can withstand temperatures higher than 300° C. without decomposition. The halogenated oil can be a perfluoropolyether, a fluorosilicone, a polytrifluorochloroethylene, or combinations of two or more thereof. The thickening agent can be finely divided silica, boron nitride, clay, soap, poly(tetrafluoroethylene), clay, talc, silica, titanium dioxide, polydimethylsiloxane, polyurea, polyurethane, or combinations of two or more thereof.

Claims (82)

1. A composition comprising an aryl perfluoropolyether which is a monofunctional aryl perfluoropolyether having the formula of R f —(Y) a —(C t R (u+v) )—(O—C t R 1 (u+v) ) b —R wherein

R f has a formula weight of about 400 to about 15,000;

R f comprises repeat units selected from the group consisting of

(a) J-O—(CF(CF 3 )CF 2 O) c (CFXO) d CFZ—,

(b) J 1 -O—(CF 2 CF 2 O) e (CF 2 O) f CFZ 1 —,

(c) J 2 -O—(CF(CF 3 )CF 2 O) j CF(CF 3 )—,

(d) J 3 -O-(CQ 2 -CF 2 CF 2 —O) k -CQ 2 -,

(e) J 3 -O—(CF(CF 3 )CF 2 O) g (CF 2 CF 2 O) h (CFX—O) i —CFZ—,

(f) J 4 -O—(CF 2 CF 2 O) k —CF 2 —, and

(g) combinations of two or more thereof; and

where

the units with formulae CF 3 CF 2 O and CF 2 O are randomly distributed along the chain;

J is CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, C 3 F 6 Cl, or combinations of two or more thereof;

c and d are numbers such that the c/d ratio ranges from about 0.01 to about 0.5;

X is —F, —CF 3 , or combinations thereof;

Z is —F, —Cl or —CF 3 ;

Z 1 is —F or —Cl,

J 1 is CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, or combinations of two or more thereof;

e and f are numbers such that the elf ratio ranges from about 0.3 to about 5;

J 2 is —C 2 F 5 , —C 3 F 7 , or combinations thereof;

j is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

J 3 is CF 3 , C 2 F 5 , C 3 F 7 , or combinations of two or more thereof;

k is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

each Q is independently —F, —Cl, or —H;

g, h and i are numbers such that (g+h) ranges from about 1 to about 50, the i/(g+h) ratio ranges from about 0.1 to about 0.5;

J 4 is CF 3 , C 2 F 5 , or combinations thereof;

k′ is an average number such that the formula weight of R f ranges from about 400 to about 15,000;

each R is independently —H, a halogen, —OH, —SO 3 M, NR 3 2 , —NO 2 , —R 4 OH, —R 4 SO 3 M, —R 4 NR 3 2 , —R 4 NO 2 , —R 4 CN, —C(O)OR 4 , —C(O)OM, —C(O)R 4 , —C(O)NR 3 2 , or combinations of two or more thereof; except that when b=0, R cannot be four hydrogen atoms and —OH, or —Br, or —NH 2 ; or R cannot be solely H or —NO 2 , or combinations thereof;

each R 1 is independently H, —R 4 , —OR 4 , a halogen, —OH, —SO 3 M, —NR 3 2 , —NO 2 , —CN, —R 4 OH, —R 4 SO 3 M, —R 4 NR 3 2 , —R 4 NO 2 , —R 4 CN, —C(O)OR 4 , —C(O)OM, —C(O)R 4 , —C(O)NR 3 2 , or combinations of two or more thereof provided that if b=0, the combination of R and R 2 cannot be four or more hydrogen atoms and —OH, —Br, —NH 2 , or —NO 2 ;

each R 3 is independently H, C 1 -C 10 alkyl, or combinations of two or more thereof;

R 4 is a C 1 -C 10 alkyl;

M is a hydrogen or metal ion;

a is 0 or 1;

b is 0-5;

Y is a divalent radical —CH 2 OCH 2 —, —(CH 2 ) o —O—, —(CF 2 ) n —, —CF 2 O—, —CF 2 OCF 2 —, —C(O)—, —C(S)—, or combinations of two or more thereof;

n is about 1 to about 5;

o is about 2 to about 5;

t is equal to 6+u;

u is any combination of 0, 2, 4, 6, 8, 10, 12, 14, 16; and

v is independently either 2 or 4.

2. A composition according to claim 1 wherein M is H, Li, Na, K, Ca, or combinations of two or more thereof.

3. A composition according to claim 1 wherein b is 0 and R is not four hydrogen atoms and —OH, or —Br, or —NH 2 ; or solely H or —NO 2 groups or combinations thereof.

4. A composition according to claim 1 wherein said aryl perfluoropolyether is CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 Br 3 H 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 F 3 H 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 Cl,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 N(CH 3 ) 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 3 [OC(O)CH 3 ] 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 SO 3 M,

CF 3 (CF 2 ) 2 (OCF(CF 2 ) y OCF(CF 3 )CF 2 C 6 H 3 (OH) 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 OC 6 H 5 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 (C 6 H 4 O) 2 C 6 H 5 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 OC 6 H 4 SO 3 M,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 OC 6 H 4 OC 6 H 4 NO 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 10 H 6 SO 3 M, or combinations of two or more thereof and y is from about 3 to about 100.

5. A composition according to claim 4 wherein said aryl perfluoropolyether is

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 SO 3 M,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 3 (OH) 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 OC 6 H 5 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 (C 6 H 4 O) 2 C 6 H 5 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 OC 6 H 4 SO 3 M,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 OC 6 H 4 OC 6 H 4 NO 2 ,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 10 H 6 SO 3 M, or combinations of two or more thereof.

6. A composition according to claim 5 wherein said aryl perfluoropolyether is

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 SO 3 M,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 OC 6 H 4 SO 3 M,

CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 10 H 6 SO 3 M, or combinations of two or more thereof and M is H, Li, Na, K, Ca, or combinations of two or more thereof.

7. A composition according to claim 6 wherein said aryl perfluoropolyether is CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 SO 3 M.

8. A composition according to claim 6 wherein said aryl perfluoropolyether is CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 6 H 4 OC 6 H 4 SO 3 M.

9. A composition according to claim 6 wherein said aryl perfluoropolyether is CF 3 (CF 2 ) 2 (OCF(CF 3 )CF 2 ) y OCF(CF 3 )CF 2 C 10 H 6 SO 3 M.

10. A composition according to claim 1 wherein said composition is said aryl perfluoropolyether.

11. A composition according to claim 7 wherein said composition is said aryl perfluoropolyether.

12. A composition according to claim 8 wherein said composition is said aryl perfluoropolyether.

13. A composition according to claim 9 wherein said composition is said aryl perfluoropolyether.

14. A composition according to claim 1 or 4 , further comprising a halogenated oil which is a perfluoropolyether.

15. A composition according to claim 14 wherein said aryl perfluoropolyether is present in said composition from about 0.01 to about 99% by weight.

16. A composition according to claim 1 or 4 , further comprising a halogenated oil and a thickening agent, wherein said halogenated oil is a perfluoropolyether, a fluorosilicone, a polytrifluorochloroethylene, or combinations of two or more thereof; and said thickening agent is polytetrafluoroethylene, talc, silica, clay, boron nitride, metal soaps, titanium dioxide, polydimethylsiloxane, polyurea, polyurethane, or combinations of two or more thereof.

17. A composition according to claim 16 further comprising an additive wherein said additive is perfluoroalkyl surfactant, polyoxyperfluoroalkyl surfactant, oil or grease stabilizer, anticorrosive agent, anti-wear agent, or combinations of two or more thereof.

18. A composition according to claim 17 wherein said aryl perfluoropolyether is present in said composition from about 0.1 to about 90% and said thickening agent is present in said composition from about 0.01 to about 60%, both by weight.

19. A grease composition comprising, or produced by combining, a halogenated oil, an aryl perfluoropolyether and a thickening agent, wherein said halogenated oil is a perfluoropolyether, a fluorosilicone, polytrifluorochloroethylene, or combinations of two or more thereof; said aryl perfluoropolyether is the same as recited in claim 1 or 4 , and said thickening agent is polytetrafluoroethylene, talc, silica, clay, boron nitride, metal soaps, titanium dioxide, polydimethylsiloxane, polyurea, polyurethane, or combinations of two or more thereof.

20. A grease composition according to claim 19 further comprising an additive wherein said additive is perfluoroalkyl surfactant, polyoxyperfluoroalkyl surfactant, oil or grease stabilizer, anticorrosive agent, anti-wear agent, or combinations of two or more thereof.

21. A grease composition according to claim 20 wherein said aryl perfluoropolyether is present from about 0.1 to about 90% and said thickening agent is present from about 0.01 to about 50%, both by weight of said grease.

22. A composition comprising, or produced by combining, a perfluoropolyether, an aryl perfluoropolyether and a thickening agent, wherein said aryl perfluoropolyether is the same as recited in claim 5 ; and said thickening agent is polytetrafluoroethylene, talc, silica, day, boron nitride, metal soaps, titanium dioxide, polydimethylsiloxane, polyurea, polyurethane, or combinations of two or more thereof.

Assignments (4)
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →