IP Library Granted Patent US 7,569,527
Granted Patent B2
US 7,569,527 · App. 11/167,330 · Granted Aug 4, 2009

Fluoro derivative-substituted aryl pnictogens and their oxides

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Quick Facts
Patent No.
US 7,569,527
App. No.
11/167,330
Granted
Aug 4, 2009
Kind
B2
Abstract

Substituted aryl pnictogen derivative compositions having the structure of [R f 1 -(C t R (u+v) )] m E(O) n (C t R 1 (u+v+1) ) (3-m) wherein E is phosphorous, arsenic or antimony; R f 1 is a fluoropolyether chain; C t R (u+v) and C t R 1 (u+v+1) represent aryl groups, n is 0 or 1 and m is greater than about 0.5 to about 3. Such compositions have utility as additives for high temperature lubricants.

Claims (84)

1. A substituted aryl pnictogen composition having the structure of:

[R f 1 -(C t R (u+v) )] m E(O) n (C t R 1 (u+v+1) ) (3-m)

wherein

R f 1 is a fluoropolyether chain having a formula weight ranging from about 400 to about 15,000, comprises repeat units, and is 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 )CF 2 -;

(d) J 3 -O-(CQ 2 -CF 2 CF 2 -O) k -CQ 2 -CF 2 -;

(e) J 3 -O-(CF(CF 3 )CF 2 O) g (CF 2 CF 2 O) h (CFXO) i -CFZ-;

(f) J 4 -O-(CF 2 CF 2 O) r CF 2 -; and

(h) combinations of two or more thereof

wherein

J is a fluoroalkyl group selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, C 3 F 6 Cl, and combinations of two or more thereof;

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

X is F, CF 3 , or combinations thereof;

Z is F, Cl or CF 3 ;

J 1 is a fluoroalkyl group selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , CF 2 Cl, C 2 F 4 Cl, and combinations of two or more thereof;

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

Z 1 is F or Cl;

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 selected from the group consisting of CF 3 , C 2 F 5 , C 3 F 7 , and 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 ratio of i:(g+h) ranges from about 0.1 to about 0.5;

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

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

each R and R 1 is independently H, a C 1 -C 10 alkyl, a halogen, OR 3 , OH, SO 3 M, NR 2 2 , R 3 OH, R 3 SO 3 M, R 3 NR 2 2 , R 3 NO 2 , R 3 CN, C(O)OR 3 , C(O)OM, C(O)R 3 , or C(O)NR 2 2 , or combinations of two or more thereof;

wherein

R 2 is independently H, C 1 -C 10 alkyl, or combinations of two or more thereof;

R 3 is a C 1 -C 10 alkyl; and

M is hydrogen or a metal;

t is equal to (6+u);

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

v is independently either 2 or 4;

n is 0 or 1;

E is P, As, or Sb; and

m is greater than about 0.5 to about 3, provided that, when E=P, m=3.0 and t=6, R cannot be exclusively H or contain F.

2. The composition of claim 1 wherein R f 1 is selected from the group consisting of:

F(C 3 F 6 O) z CF(CF 3 )CF 2 -;

F(C 3 F 6 O) x (CF 2 O) w CF 2 -;

F(C 3 F 6 O) x (C 2 F 4 O) q (CF 2 O) w CF 2 -;

(R f 3 ) 2 CFO(C 3 F 6 O) x CF(CF 3 )CF 2 -; and

combinations of two or more thereof;

wherein

x is a number from 2 to about 100;

z is a number from about 3 to about 50;

q is a number from 2 to about 50;

w is a number from 2 to about 50;

each R f 3 can be the same or different and is independently a monovalent C 1 to C 20 branched or linear fluoroalkane; and

C 3 F 6 O is linear or branched.

3. The composition of claim 2 wherein R f 1 is selected from the group consisting of: F(C 3 F 6 O) z CF(CF 3 )CF 2 -; (R f 3 ) 2 CFO(C 3 F 6 O) x CF(CF 3 )CF 2 -; and combinations thereof.

4. The composition of claim 3 wherein R f 1 is F(CF(CF 3 )CF 2 O) z CF(CF 3 )CF 2 -.

5. The composition of claim 1 wherein n is 0.

6. The composition of claim 1 wherein n is 1.

7. The composition of claim 1 wherein E is P.

8. The composition of claim 1 wherein E is P and m is 1 or 2.

9. The composition of claim 8 wherein m is 1.

10. The composition of claim 8 wherein m is 2.

11. The composition of claim 8 wherein n is 0.

12. The composition of claim 8 wherein n is 1.

13. The composition of claim 2 wherein E is P and m is 1 or 2.

14. The composition of claim 13 wherein m is 1.

15. The composition of claim 13 wherein m is 2.

16. The composition of claim 13 wherein n is 0.

17. The composition of claim 13 wherein n is 1.

18. The composition of claim 3 wherein E is P and m is 1 or 2.

19. The composition of claim 18 wherein m is 1.

20. The composition of claim 18 wherein m is 2.

21. The composition of claim 18 wherein n is 0.

22. The composition of claim 18 wherein n is 1.

23. The composition of claim 4 wherein E is P and m is 1 or 2.

24. The composition of claim 23 wherein m is 1.

25. The composition of claim 23 wherein m is 2.

26. The composition of claim 23 wherein n is 0.

27. The composition of claim 23 wherein n is 1.

28. A perfluoropolyether lubricant comprising the composition of claim 1 wherein the composition is present in an amount of about 0.1 to about 5% by weight based on the weight of the perfluoropolyether lubricant.

29. The lubricant of claim 28 wherein composition is present in an amount of about 1 to about 2% by weight based on the weight of the perfluoropolyether lubricant.

30. A perfluoropolyether lubricant comprising the composition of claim 2 wherein the composition is present in an amount of about 0.1 to about 5% by weight based on the weight of the perfluoropolyether lubricant.

31. The lubricant of claim 30 wherein the composition is present in an amount of about 1 to about 2% by weight based on the weight of the perfluoropolyether lubricant.

32. A perfluoropolyether lubricant comprising the composition of claim 3 wherein the composition is present in an amount of about 0.1 to about 5% by weight based on the weight of the perfluoropolyether lubricant.

33. The lubricant of claim 32 wherein the composition is present in an amount of about 1 to about 2% by weight based on the weight of the perfluoropolyether lubricant.

34. A perfluoropolyether lubricant comprising the composition of claim 4 wherein the composition is present in an amount of about 0.1 to about 5% by weight based on the weight of the perfluoropolyether lubricant.

35. The lubricant of claim 34 wherein the composition is present in an amount of about 1 to about 2% by weight based on the weight of the perfluoropolyether lubricant.

Assignments (5)
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 INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2005
From: HOWELL, JON LEE; HAY, KEVIN ANTHONY
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 016457/0307 →