IP Library Granted Patent US 7,291,696
Granted Patent B2
US 7,291,696 · App. 11/267,849 · Granted Nov 6, 2007

Composition and associated method

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Quick Facts
Patent No.
US 7,291,696
App. No.
11/267,849
Granted
Nov 6, 2007
Kind
B2
Abstract

Provided is a fluorine substituted oligomeric or polymeric ester including the reaction product of a fluorine substituted acrylate or a fluorine substituted methacrylate; an unsaturated anhydride; and an alkyl acrylate or an alkyl methacrylate. Also provided is a method of making the composition.

Claims (43)

1. A copolymer comprising polyether imide and a composition comprising a terpolymer having the structure of formula (I)

wherein R1 comprises an alkyl radical; R2 comprises of a formula CF 3 (CF 2 )p(CH 2 )q- wherein “p” is an integer in a range of from 1 to about 21, and “q” is an integer in a range of from 1 to about 10; R3 and R4 are separately hydrogen or a short chain alkyl; and

“m” is an integer areater than 1, “n” is an integer greater than about 2 to about 20,000, and “o” is an integer greater than about 2.

2. The copolymer as defined in claim 1 , wherein the polyether imide comprises the structure as shown in formula (II):

3. A copolymer comprising the reaction product of a polysulfone and a composition comprising a terpolymer having the structure of formula (I)

wherein R1 comprises an alkyl radical; R2 comprises of a formula CF 3 (CF 2 )p(CH 2 )q- wherein “p” is an integer in a range of from 1 to about 21, and “q” is an integer in a range of from 1 to about 10; R3 and R4 are separately hydrogen or a short chain alkyl; and

“m” is an integer greater than 1, “n” is an integer greater than about 2 to about 20,000, and “o” is an integer greater than about 2.

4. A cured or cross-linked material formed from the mixture as defined in claim 1 .

5. A fluorine substituted oligomeric or polymeric ester comprising the reaction product of:

a fluorine substituted acrylate or a fluorine substituted methacrylate;

an unsaturated anhydride; and

an alkyl acrylate or an alkyl methacrylate.

6. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 , wherein the unsaturated anhydride itaconic anhydride or maleic anhydride.

7. The fluorine substituted oligomeric or polymeric ester as defined in claim 6 , wherein the itaconic anhydride is present in an amount in a range of greater than about 20 mole percent.

8. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 wherein the itaconic anhydride is present in an amount of about 25 mole percent.

9. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 , wherein the fluorine substituted acrylate comprises 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl acrylate.

10. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 , wherein the fluorine substituted acrylate is present in an amount in a range of greater than about 20 mole percent.

11. The fluorine substituted oligomeric or polymeric ester as defined in claim 10 , wherein the fluorine substituted acrylate is present in an amount of about 25 mole percent.

12. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 , wherein the alkyl acrylate is present in an amount in a range of greater than about 35 mole percent.

13. The fluorine substituted oligomeric or polymeric ester as defined in claim 12 , wherein the alkyl acrylate is present in an amount of about 50 mole percent.

14. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 , wherein the alkyl acrylate comprises butyl acrylate.

15. The fluorine substituted oligomeric or polymeric ester as defined in claim 5 , further comprising residual amounts of an azo-based free radical polymerization initiator.

16. A copolymer comprising the reaction product of polyether imide and the fluorine substituted oligomeric or polymeric ester as defined in claim 5 .

17. A mixture comprising a polyfunctional cross-linking agent and the fluorine substituted oligomeric or polymeric ester as defined in claim 5 .

18. The mixture as defined in claim 17 , wherein the cross-linking agent comprises a polyfunctional amine.

19. The mixture as defined in claim 18 , wherein the polyfunctional amine comprises one or both of 2,2′-(ethylenedioxy) diethylamine or hexamethylenediamine.

20. The mixture as defined in claim 18 , wherein:

the fluorine substituted acrylate consists essentially of 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl acrylate; and

the alkyl acrylate consists essentially of butyl acrylate.

21. An article comprising the cured product of the mixture as defined claim 17 .

22. A method, comprising:

reacting a fluorine substituted acrylate or a fluorine substituted methacrylate; an unsaturated anhydride; an alkyl acrylate or an alkyl methacrylate; and an initiator in a solvent.

23. The method as defined in claim 22 , wherein the solvent comprises tetrahydrofuran.

24. The method as defined in claim 22 , wherein the fluorine substituted acrylate comprises 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl acrylate.

25. The method as defined in claim 22 , wherein the alkyl acrylate comprises butyl acrylate.

26. The method as defined in claim 22 , wherein the initiator comprises an azo-based free radical polymerization initiator.

27. The method as defined in claim 26 , wherein the initiator comprises 2,2′-azobisisobutyronitrile.

28. The method as defined in claim 22 , wherein reacting comprises free radical polymerization to form a terpolymer.

29. The method as defined in claim 28 , further comprising contacting the terpolymer to polyfunctional cross-linking agent.

30. The method as defined in claim 29 , wherein the cross-linking agent comprises one or both of 2,2′-(ethylenedioxy)diethylamine or hexamethylenediamine.

31. The method as defined in claim 29 , further comprising curing the terpolymer to form a cross-linked article.

32. The method as defined in claim 31 , wherein curing comprises applying thermal energy to increase the temperature of the curing agent and the terpolymer to be at a temperature of about 130 degrees Celsius.

33. The method as defined in claim 31 , wherein curing comprises generating a network of hydrophlic functionality such as carboxylic acid groups and inter/intramolecular ammonium-carboxylate ion pairs to enhance hydrophilicity.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2023
From: PARKER INTANGIBLES LLC
To: PARKER-HANNIFIN CORPORATION
Reel/Frame 063461/0669 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2022
From: PARKER-HANNIFIN CORPORATION
To: PARKER INTANGIBLES LLC
Reel/Frame 060440/0130 →
MERGER Recorded May 13, 2022
From: BHA ALTAIR, LLC
To: PARKER-HANNIFIN CORPORATION
Reel/Frame 060062/0932 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 3, 2014
From: GENERAL ELECTRIC COMPANY; BHA GROUP, INC.; ALTAIR FILTER TECHNOLOGY LIMITED
To: BHA ALTAIR, LLC
Reel/Frame 031911/0797 →